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Limited Quantity | USD 15-60 |
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CAS No. : | 629-62-9 | MDL No. : | MFCD00008990 |
Formula : | C15H32 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YCOZIPAWZNQLMR-UHFFFAOYSA-N |
M.W : | 212.41 | Pubchem ID : | 12391 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 12 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 74.22 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -2.1 cm/s |
Log Po/w (iLOGP) : | 4.5 |
Log Po/w (XLOGP3) : | 7.74 |
Log Po/w (WLOGP) : | 6.1 |
Log Po/w (MLOGP) : | 6.19 |
Log Po/w (SILICOS-IT) : | 5.77 |
Consensus Log Po/w : | 6.06 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.24 |
Solubility : | 0.00122 mg/ml ; 0.00000574 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -7.58 |
Solubility : | 0.00000555 mg/ml ; 0.0000000261 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.92 |
Solubility : | 0.000254 mg/ml ; 0.00000119 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 2.15 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P501-P273-P210-P280-P370+P378-P391-P331-P301+P310-P403+P235-P405 | UN#: | 3082 |
Hazard Statements: | H227-H304-H411 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; nickel at 250℃; | ||
With nickel kieselguhr; benzene at 262℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With hydrogen In cyclohexane at 300℃; for 6h; | 2.3. Catalytic deoxygenation General procedure: The catalytic deoxygenation of MO, JO and WCO using fresh NiCeAlcatalysts were conducted using a stirred batch reactor [YZPR-100(M),YanZheng Instrument, Shanghai, China] with a maximum operatingpressure of 15 MPa at 400 . In each experiment, after the reactor waspurged with pure N2 at least 3 times at room temperature, 0.1 g catalystand 1 g reactant were introduced into the reactor which then was slowlyheated to reaction temperature (300 ). Then 2.5 MPa H2 was introducedto initiate the catalytic deoxygenation reaction for 6 h. In order toreduce the error and contingency during test, all experiments wererepeated at least three times to ensure the accuracy of the data. Recyclabilitytest and deoxygenation experiments using fresh, spent and regenerated NiCeAl-3.0 were also performed at the same conditiondescribed above |
With nickel Hydrogenation.unter Hochdruck; | ||
With Pd-BaSO4; hydrogen In hexane at 280℃; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With terephthalonitrile; 2,3,3,4,4,5-hexamethyl-2-hexanethiol; phenanthrene In water; acetonitrile at 20℃; for 6h; Irradiation; | |
82.7% | at 300℃; for 4h; Sealed vial; Inert atmosphere; | 1.9 Catalyst Screening: High throughput catalyst screening for thedecarboxylation of free fatty acids was conducted using a high-temperature batch 24-well reactor made by Symyx. The 24 vials were loaded with catalyst and free fatty acid feedstock, in a 2 to 1 weight ratio. The vials were sealed under a nitrogen atmosphere with a Kapton-backed graphite sheet. Once loaded into the high temperature reactor and sealed, the reactor headspace was pressurized with 40 psig nitrogen to discourage leaking of the individual vials. The reactor was placed into a stationary furnace and heated to 300°C for 4 hours. After completion the reactor was removed from the furnace and allowed to cool to room temperature.Analytical work-up of each sample involved BSTFA/pyridine derivatization, which was carried out as follows. The sample was diluted with chloroform containing 1 mg/mL heptadecanoic acid as an internal standard, mixed well, and centrifuged. A 500 μ^ aliquot was removed and added to a 2 mL vial. To this second vial was added 500 μ^ of N,0-bis[trimethylsilyl]trifluoroacetamide(BSTFA) and 500 μ^ of pyridine. The vial was mixed well, capped, and heated to 70°C for 1 hour. GC-FID and GC-MS were utilized for quantification and identification of the product mixture. Analysis was performed using a DB5-HT column (15 m x 250 μιη x 0.10 μιη nominal film thickness). The injector was held at 340°C with a 150: 1 split. With a flow rate of 2 mL/min H2, the column was heated from 80°C to 350°C at 25°C/min and then held at 350°C for 9.2 min. |
66% | With 1-hydroxy-2(1H)-pyridinethione; dmap; chloroform; dicyclohexyl-carbodiimide for 2h; Reflux; Irradiation; |
61% | With photodecarboxylase from Chlorella variabilis NC64A In dimethyl sulfoxide at 37℃; for 24.5h; Irradiation; Sealed tube; Enzymatic reaction; | |
17.6% | With palladium 10% on activated carbon; hydrogen In decane at 260℃; for 2h; Autoclave; | 1 Example 1 (Catalytic Reaction) 51.2 mg of palmitic acid, 42.5 mg of the catalyst 1 and 2 mL of decane were weighed, placed in an autoclave (model TVS-N 2 manufactured by Taiatsu techno corp.), and it was heated with a metal bath (manufactured by Koike precision instruments) while stirring with a magnetic stirrer under a hydrogen atmosphere. The reaction was conducted for 4 hours at a temperature of 260 ° C and a pressure of 1 MPa. (Analysis of Product) After the reaction, an internal standard substance (dodecane) was added to the reaction solution and the conversion (yield) (%) with respect to the raw material was derived by gas chromatographic analysis. The yield with respect to the raw material pentadecane, which is a linear hydrocarbon (B), was 69.3%, and the yield with respect to the raw material hexadecane, which is a linear hydrocarbon (A), was 13.8%. The molar ratio (B / A) was 5.0 |
Irradiation.α-Strahlen; | ||
With 5% platinum on carbon In water at 330℃; for 2.5h; Autoclave; | ||
With 5% Pd/zirconia; hydrogen In dodecane at 20 - 260℃; Autoclave; | ||
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / chloroform / 20 °C / Inert atmosphere 2: 2-mercaptopyridine-1-oxide sodium salt; dmap; chloroform / Irradiation; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / chloroform / 1 h / 20 °C / Inert atmosphere 2: 2-mercaptopyridine-1-oxide sodium salt; dmap; chloroform / 0.25 h / Inert atmosphere; Irradiation; Reflux | ||
With recombinant Chlorella variablis NC64A fatty acid photodecarboxylase from Escherichia coli In glycerol at 25℃; Irradiation; Enzymatic reaction; | 2.2.3 Enzyme kinetic assays Gas chromatography with flame-ionized detection (GC-FID) was used to monitor palmitic acid consumption and pentadecane production by CvFAP. Reactions were conducted by mixing CvFAP with palmitic acid (various concentrations; see below) in 50mM Tris-HCl (pH 8.0), 5% glycerol and 1mM 2-mercaptoethanol at 25°C. Reactions were contained in a quartz cuvette and were initiated using a 455 nm LED. To monitor CvFAP turnover, reactions were quenched at specific time points by placing them in the dark. These samples were mixed with 50% (v/v) ethyl acetate and 0.1% (v/v) sec-butyl benzene. Samples were centrifuged for 1min using a benchtop centrifuge. MgCl2 was added to the supernatant and centrifuged for a further 2min. The supernatant was subsequently removed and analysed by gas chromatography (7890AGC systems, Agilent Technologies). Sec-butyl benzene was used as an internal standard. The retention time of sec-butyl benzene was approx. 8-9 min. Pentadecane produced was monitored as a function of reaction time. Initial velocity data associated with CvFAP catalysis were calculated by linear fitting to concentration determined at different reaction times. Apparent kcat and KM values for CvFAP in steady-state reactions with palmitic acid were determined by fitting in Origin Pro 9.1 to the standard Michaelis-Menten equation: (Eq.1) v=kcat[palmitic acid]/Km+[palmitic acid] | |
With hydrogen In dodecane at 280℃; for 6h; | ||
With hydrogen at 300℃; for 6h; Autoclave; | ||
With fatty acid photo-decarboxylase from Chlorella variabilis NC64A In dimethyl sulfoxide at 30℃; for 20h; Irradiation; Sealed tube; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-methylpropan-2-thiol In toluene at 110℃; for 3h; adding 30 min; Yield given; | ||
With tri-n-butyl-tin hydride In benzene at 80℃; for 0.5h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 83% 2: 150 mg 3: 82% | With 2-methylpropan-2-thiol In benzene for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 83% 2: 82% | With 2-methylpropan-2-thiol In benzene at 80℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In ethanol for 2h; Ambient temperature; | ||
With hydrogen In ethanol for 1.75h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In ethanol for 2h; Ambient temperature; | ||
With hydrogen In ethanol for 1.75h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; antimony triphenylsulphide In chlorobenzene for 2h; Heating; | |
With hydrogenchloride; thiophenol; antimony tris-benzenethiolate Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 92% 2: 90% | With 2-methylpropan-2-thiol In benzene at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 5% 2: 74% 3: 75% | With 2-methylpropan-2-thiol In xylene at 140℃; for 48h; | |
1: 23% 2: 16% 3: 54% | In xylene at 140℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 90% 2: 92% | In benzene at 80℃; for 2h; | |
1: 90% 2: 92% | In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction; Zn-cathode, 15 F/mol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1-Benzyl-1,4-dihydronicotinamide; 2-methylpropan-2-thiol In tetrahydrofuran; water for 0.5h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 17 % Chromat. 2: 70% | With antimony(III) chloride In dichloromethane at 0℃; for 1h; | |
1: 70 % Chromat. 2: 17 % Chromat. | With antimony(III) chloride In dichloromethane at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With acridine In benzene for 2h; Irradiation; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With thiophenol In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 30% 2: 50% | With 1-hydroxy-2(1H)-pyridinethione; dmap; allytriphenyltin In xylene at 142℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogen In 1,2-dimethoxyethane at 150℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 34% 2: 28% 3: 17% | With potassium methanolate In methanol at 40 - 45℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 1.4 F mol-1; cell voltage 11-15 V; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nickel at 255℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air at 1130℃; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air at 1130℃; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With d8-isopropanol; 5% rhodium-on-charcoal; 10% Pt/activated carbon; water-d2 at 120℃; for 24h; Sealed tube; | |
With water-d2 at 250℃; for 16h; | ||
With 5% rhodium-on-charcoal; hydrogen; water-d2 at 160℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.1 mmol | With sodium hydroxide; water In methanol at 250℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dimethyldisulphide; hydrogen;cobalt-molybdenum on alumina; at 363℃; under 75757.6 Torr; for 120h;Product distribution / selectivity; | Experiment 2; The same procedure as Experiment 1 was followed, except that the reactor pressure was maintained at 100 barg (10.1 MPa). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / toluene / 0.17 h / Ambient temperature 2: t-butylthiol / toluene / 3 h / 110 °C / adding 30 min | ||
Multi-step reaction with 2 steps 1: DMAP / benzene / Heating; 10-15 min 2: t-butylthiol / toluene / 3 h / 110 °C / adding 30 min | ||
182 mg | With dmap; chloroform; 2-mercaptopyridine-1-oxide sodium salt Irradiation; Inert atmosphere; |
Stage #1: n-hexadecanoyl chloride With dmap; 2-mercaptopyridine-1-oxide sodium salt In chloroform at 57℃; for 0.416667h; Inert atmosphere; Stage #2: In chloroform for 1.83333h; Inert atmosphere; Irradiation; | ||
182 mg | With dmap; chloroform; 2-mercaptopyridine-1-oxide sodium salt for 0.25h; Inert atmosphere; Irradiation; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 1.) EtMgBr; 2.) CuCl / 1.) THF, 1 h, reflux; 2.) THF, reflux, 4 h 2: 68 percent / H2 / 10percent Pd-C, quinoline / benzene / Ambient temperature 3: 98 percent / d-camphorsulfonic acid, Et3N / methanol / Ambient temperature 4: 94 percent / pyridine, dimethylaminopyridine / 0 degC then 1 h, room temperature 5: 78 percent / NaI, Na2S2O3 / acetone / Ambient temperature 6: acetonitrile / 11 h, room temperature then 36 h, 40 degC 7: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 8: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 8 steps 1: 1.)EtMgBr 2.)CuCl2 / 1.)THF 2.)THF, reflux, 4 h 2: 68 percent / hydrogen / Lindlar-catalyst / benzene / 760 Torr / Ambient temperature 3: 98 percent / d-camphorsulfonic acid / methanol / 0.75 h / Ambient temperature 4: pyridine / 4.5 h / 0 °C 5: NaI / acetone / 12 h / Ambient temperature 6: 92 percent / acetonitrile / 36 h / 40 °C 7: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 8: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 8 steps 1: 1.)EtMgBr 2.)CuCl2 / 1.)THF 2.)THF, reflux, 4 h 2: 68 percent / hydrogen / Lindlar-catalyst / benzene / 760 Torr / Ambient temperature 3: 98 percent / d-camphorsulfonic acid / methanol / 0.75 h / Ambient temperature 4: pyridine / 4.5 h / 0 °C 5: NaI / acetone / 12 h / Ambient temperature 6: 92 percent / acetonitrile / 36 h / 40 °C 7: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 8: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyridine / 0 degC, 6 h then 30 min, room temperature 2: 79 percent / NaI, Na2S2O3 / acetone / Ambient temperature 3: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 4: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 5: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: pyridine / 0 degC, 6 h then 30 min, room temperature 2: 79 percent / NaI, Na2S2O3 / acetone / Ambient temperature 3: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 4: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 5: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 4 steps 1: 1.)TsCl, 2.)NaI / 1.)pyridine, 2.)acetone 2: acetonitrile 3: 1.)n-BuLi 4: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 79 percent / NaI, Na2S2O3 / acetone / Ambient temperature 2: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 3: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 4: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 4 steps 1: 79 percent / NaI, Na2S2O3 / acetone / Ambient temperature 2: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 3: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 4: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 94 percent / pyridine, dimethylaminopyridine / 0 degC then 1 h, room temperature 2: 78 percent / NaI, Na2S2O3 / acetone / Ambient temperature 3: acetonitrile / 11 h, room temperature then 36 h, 40 degC 4: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 5: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: pyridine / 4.5 h / 0 °C 2: NaI / acetone / 12 h / Ambient temperature 3: 92 percent / acetonitrile / 36 h / 40 °C 4: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 5: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: pyridine / 4.5 h / 0 °C 2: NaI / acetone / 12 h / Ambient temperature 3: 92 percent / acetonitrile / 36 h / 40 °C 4: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 5: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetonitrile / 11 h, room temperature then 36 h, 40 degC 2: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 3: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 92 percent / acetonitrile / 36 h / 40 °C 2: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 3: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 92 percent / acetonitrile / 36 h / 40 °C 2: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 3: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 68 percent / H2 / 10percent Pd-C, quinoline / benzene / Ambient temperature 2: 98 percent / d-camphorsulfonic acid, Et3N / methanol / Ambient temperature 3: 94 percent / pyridine, dimethylaminopyridine / 0 degC then 1 h, room temperature 4: 78 percent / NaI, Na2S2O3 / acetone / Ambient temperature 5: acetonitrile / 11 h, room temperature then 36 h, 40 degC 6: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 7: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 68 percent / hydrogen / Lindlar-catalyst / benzene / 760 Torr / Ambient temperature 2: 98 percent / d-camphorsulfonic acid / methanol / 0.75 h / Ambient temperature 3: pyridine / 4.5 h / 0 °C 4: NaI / acetone / 12 h / Ambient temperature 5: 92 percent / acetonitrile / 36 h / 40 °C 6: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 7: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 68 percent / hydrogen / Lindlar-catalyst / benzene / 760 Torr / Ambient temperature 2: 98 percent / d-camphorsulfonic acid / methanol / 0.75 h / Ambient temperature 3: pyridine / 4.5 h / 0 °C 4: NaI / acetone / 12 h / Ambient temperature 5: 92 percent / acetonitrile / 36 h / 40 °C 6: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 7: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 98 percent / d-camphorsulfonic acid, Et3N / methanol / Ambient temperature 2: 94 percent / pyridine, dimethylaminopyridine / 0 degC then 1 h, room temperature 3: 78 percent / NaI, Na2S2O3 / acetone / Ambient temperature 4: acetonitrile / 11 h, room temperature then 36 h, 40 degC 5: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 6: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 6 steps 1: 98 percent / d-camphorsulfonic acid / methanol / 0.75 h / Ambient temperature 2: pyridine / 4.5 h / 0 °C 3: NaI / acetone / 12 h / Ambient temperature 4: 92 percent / acetonitrile / 36 h / 40 °C 5: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 6: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 6 steps 1: 98 percent / d-camphorsulfonic acid / methanol / 0.75 h / Ambient temperature 2: pyridine / 4.5 h / 0 °C 3: NaI / acetone / 12 h / Ambient temperature 4: 92 percent / acetonitrile / 36 h / 40 °C 5: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 6: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 78 percent / NaI, Na2S2O3 / acetone / Ambient temperature 2: acetonitrile / 11 h, room temperature then 36 h, 40 degC 3: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 4: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 4 steps 1: NaI / acetone / 12 h / Ambient temperature 2: 92 percent / acetonitrile / 36 h / 40 °C 3: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 4: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 4 steps 1: NaI / acetone / 12 h / Ambient temperature 2: 92 percent / acetonitrile / 36 h / 40 °C 3: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 4: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 2: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 2: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 1.)n-BuLi 2: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1.5 h then room temperature, 2 h 2: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 2: hydrogen / Pt / ethanol / 2 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 1.)n-BuLi / 1.)THF, HMPT, -78 deg C, 20 min 2.)-78 to 25 deg C, 2 h 2: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps 1: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 2: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 3: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 2: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 3: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: acetonitrile 2: 1.)n-BuLi 3: hydrogen / Pt / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
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95% | In dichloromethane; acetone | 1 4-Methylumbelliferone heptanoate EXAMPLE 1 4-Methylumbelliferone heptanoate 2g of 4-methylumbelliferone, sodium salt, are dissolved in 20 ml of acetone; 4 g of heptanoyl chloride are added dropwise at room temperature and under anhydrous conditions. When, after a short time, the reaction is completed, the solvent is evaporated and the residue taken up in methylene chloride, while repeatedly washing with diluted sodium bicarbonate; the organic phase is separated, dried and the solvent evaporated under vacuum; the title compound, purified by crystallization from methanal/hezane - heptane - octane, is obtained in 95% yield, m.p. 39-41°C. |
Yield | Reaction Conditions | Operation in experiment |
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With water at 260℃; | 4 Example 4Combined Gasification and Fischer-Tropsch in a Single ReactorA carbon supported platinum rhenium catalyst was prepared to contain 5 wt % platinum and an atomic ratio of Pt/Re of 1:2.5. This catalyst was prepared via the incipient wetting of an aqueous solution of dihydrogenhexachloroplatinate (IV) hexahydrate (39.85% Pt) (Alfa Aesar, a wholly-owned subsidiary of Johnson Matthey Company, Ward Hill, Mass.) and perrhenic acid on a hydrogen peroxide functionalized UU 60×120 mesh carbon and dried at 100° C. under vacuum.An amount (9.64 grams) of this catalyst was loaded in a ½ inch stainless steel reactor and reduced in flowing hydrogen before reaction. The stainless steel reactor was heated using an aluminum block heater to maintain isothermal conditions.A 70 wt % glycerol-in-water solution was fed over the catalyst at 260° C. and 600 psig at a WHSV of 2.4 based on the glycerol (2.4 grams of glycerol per gram of catalyst per hour). At these reaction conditions the feed remained in the condensed form over the catalyst bed.Under the stated reaction conditions, 100% of the glycerol was converted. Ninety-three percent (93%) of the carbon was collected in gas-phase products. One percent (1%) of the carbon was collected as an organic layer that was analyzed via GCMS. Analysis of this organic layer showed the presence of C9 through C20 hydrocarbons. See Table 7.While the yields are low, this Example clearly demonstrates that the reaction yields long-chain hydrocarbons. The presence of these long chain hydrocarbons indicates that a Fischer-Tropsch reaction is occurring within the single reactor system. |
Yield | Reaction Conditions | Operation in experiment |
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With oxygen; ozone; In water; | Example B; Degradation of benzo[a]pyrene; This example focuses on an integrated treatment of benzo[a]pyrene involving sequential chemical oxidation and biological degradation. The objectives are to: 1) provide mechanistic details in the ozone-mediated degradation of benzo[a]pyrene in the aqueous phase, 2) test the biodegradability of resultant intermediates, and 3) test the feasibility for the coupled chemical-biological treatment of the 5-ring PAH. Batch and packed column reactors were used to examine the degradation pathways of benzo[a]pyrene subject to ozonation in the aqueous phase. After different ozonation times, samples containing reaction intermediates and byproducts from both reactors were collected, identified for organic contents, and further biologically inoculated to determine their biodegradability. The O3-pretreated samples were incubated for 5, 10, 15, and 20 days; afterward biochemical oxygen demand (BOD), chemical oxygen demand (COD), and E-Coli toxicity tests were conducted along with qualitative and quantitative determinations of benzo[a]pyrene, intermediates, and reaction products by GC/FID and GC/MS methods. Prevalent intermediates identified at different stages included ring-opened aldehydes, phthalic derivatives, and aliphatics. The degradation of benzo[a]pyrene is primarily initiated via O3-mediated ring-opening, followed by O3 and hydroxyl radical fragmentation, and ultimately brought to complete mineralization primarily via hydroxyl radicals. Intermediates formed during chemical oxidation were biodegradable with a measured first-order rate constant (k0) of 0.18 day-1. The integrated chemical-biological system seems feasible for treating recalcitrant compounds, while pretreatment by chemical oxidation appears useful in promoting soluble intermediates from otherwise highly insoluble, biologically inaccessible benzo[a]pyrene.Materials and MethodsDescriptions of sections on Chemicals, Analytical Methods and Equipment, and Reactors and Procedures were identical to Example A. Only deviations from Example A are highlighted here. <strong>[50-32-8]Benzo[a]pyrene</strong> (BaP) (98%, Aldrich Chemical Co.) in place of pyrene was used and purified as described. A typical sample size for analysis is 150 ml and the storage temperature awaiting analysis -12 C. With the same GC/MS system, a split ratio of 5:1, solvent delay at 6 min, and scan range from m/z 15 to m/z 500 at 1.4 scan/s were used. Comparison of parent compound structure and interpretation of mass spectra of the intermediates from ion fragmentation information were performed particularly for the identification of key intermediates 7-propanal-8-methylpyrene, 7-ethyl-8-ethanalpyrene, and 4-methyl-5-hydroxylchrysene. Reactor systems (FIG. 1) were identical to ones previously used except that 0.15 g benzo[a]pyrene was prepared and loaded into the packed column reactor. Samples during batch reaction were taken at 2, 10, 20, 30, and 50 min. Sample BOD and toxicity were determined in triplicates and duplicates, respectively. Previous analytical efforts for pyrene were redirected toward benzo[a]pyrene.; Results and DiscussionThe degradation pathway, biodegradability of intermediates, and oxidant balance during ozonation of BaP will be addressed in turn.Degradation Pathways of Ozonated <strong>[50-32-8]Benzo[a]pyrene</strong>COD measurements were made for three solutions: 1) a saturated aqueous solution of BaP, 2) the solution after ozonation of a batch of excess BaP suspension (0.150 g/10.7 L), and 3) the effluent of a column packed with excess BaP solid (0.149 g) and glass beads (7.5 in. in bed-length). The saturated BaP solution was prepared by allowing excess BaP solid to reach dissolution equilibrium in water overnight followed by removal of the excess solid using a 0.45-mum filter. The ozonated batch solution was obtained after 50 min of ozonation and filtered, while the column effluent was collected from the packed column fed with an ozonated water over a 4-hr period and filtered. Table B-I shows the results COD measurements of all solutions and one BOD5 measurement for the column effluent. The saturated solution of BaP, due to its very limited aqueous solubility, registered a negligible COD value compared to that of the ozonated batch solution or the ozonated column effluent. In both the batch and column solutions, much higher COD values were measured after ozonation, which indicated dissolution of daughter compounds of BaP into the aqueous phase as a result of ozonation. A relativbiochemical oxygen demand ely high BOD5-to-COD ratio of 0.43 was observed for the column effluent, which suggested the intermediates were susceptible to biodegradation, a point of further discussion later.The COD values in the batch solution were relatively stable at about 15 mg/L during the 50-min ozonation period, as shown in FIG. 11. This seemingly steady-state level of COD could be indicative of the relatively constant quantity of intermediates that were continually added to the aqueous phase via oxidati... |
Yield | Reaction Conditions | Operation in experiment |
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With oxygen; ozone; In water; for 0.25 - 2h; | Example A; Degradation of pyrene; This example focuses on an integrated approach for the degradation of pyrene involving chemical oxidation followed by biological treatment. The objectives were to: 1) provide mechanistic details in the degradation of pyrene subject to ozone treatment, 2) test the combined technique of ozone pretreatment followed by biological degradation, and 3) test a pretreatment column to promote efficient use of chemical oxidants and biodegradability. Batch and packed column reactors were used to examine the degradation pathways of pyrene subject to ozonation in the aqueous phase. After different ozonation times, samples containing reaction intermediates and byproducts from both reactors were collected, identified for organic contents, and further biologically inoculated to determine biodegradability. The O3-pretreated samples were incubated for 5, 10, 15, and 20 days, after which biochemical oxygen demand (BOD), chemical oxygen demand (COD), and toxicity tests along with qualitative and quantitative GC/FID and GC/MS analyses of pyrene, intermediates, and products were performed. Intermediates identified at different stages included 4,5-phenanthrenedialdehyde, 2,2',6,6'-biphenyltetraaldehyde, and long-chain aliphatic hydrocarbons, which suggested that the degradation of pyrene was initiated by O3 via ring cleavage at the 4,5- and 9,10-bonds and that further oxidation ensued via reactions with both O3 and OH. until complete mineralization. Intermediates formed during chemical oxidation were biodegradable with a measured first-order rate constant (k0) of 0.243 day-. The integrated chemical-biological system appeared to be feasible for treating recalcitrant compounds, and a chemical pretreatment column was particularly useful in promoting soluble intermediates from otherwise highly insoluble, inaccessible pyrene.Materials and MethodsChemicalsOzone (1% w/w ozone in air) was generated from filtered, dry air by an ozonator (Model T-816, Polymetrics Corp.). Pyrene (99%, Aldrich Chemical Co.) was washed with distilled-deionized (DD) water three times, extracted by dichloromethane (DCM), and the solvent evaporated by a gentle stream of nitrogen gas. Stock and working indigo blue solutions were prepared from potassium indigo trisulfonate (C16H7N2O11S3K3, Aldrich Co.) per Standard Methods (APHA et al., 1992a). Polyseed (Hach Co.) was used in dilution water for biochemical oxygen demand (BOD) measurements per Standard Methods (APHA et al., 1992b). Inoculum for toxicity test was prepared according to a Hach method (HACH, 1988-1995b). COD digestion solutions (0-15,000 mg/L, 0-40 mg/L range, Hach Co.), ToxTrak reagent powder pillows, and ToxTrak accelerator solution (Hach Co.) were purchased and used according to the manufacturer's methods without further processing. Low-organic (<15 ppb as TOC), low-ion (resistivity>18 MOmega-cm), and non-pyrogenic (up to 4-log reduction with reverse osmosis pretreatment) DD water was used in all procedures (4-stage Mill-Q Plus system, Millipore Co.). Dichloromethane (Fisher Scientific) of HPLC grade was used in liquid-liquid extraction procedures. Other chemicals used in this research were of reagent grade.; Results and Discussion; Ozonation of pyrene was carried out in batch and column reactors to study: 1) the effect of reactor on intermediates and products formation, 2) the degradation pathway of pyrene under ozonation, 3) the biodegradability of intermediates, and 4) the feasibility of a combined chemical-biological treatment system for pyrene. Reaction solutions during ozonation and biodegradation processes at different stages were collected and the intermediates and byproducts identified by GC/MS techniques.1. Effects of the Reactor Type on Intermediates and Products FormationTo delineate the influence of reactor configurations on the formation of intermediates and products, ozonation experiments using aqueous and excess pyrene were carried out in batch and packed column reactors. BOD5 and COD were measured for three ozonated, filtered solutions: 1) a saturated aqueous solution of pyrene (0.13 ppm), 2) the solution after ozonation of an excess pyrene suspension (1 g/1.7 L), and 3) the effluent of a column packed with excess pyrene solid (1 g) and glass beads (7.5 in. in bed-length). The saturated pyrene solution was prepared by allowing excess pyrene solid to reach dissolution equilibrium in water overnight followed by removal of the excess solid using a 0.45-mum filter. The ozonated batch solution was obtained after 10 min of ozonation and filtered, while the effluent was collected from the packed column fed with ozonated water over a 4-hr period. Table A-I shows the results of BOD5 and COD measurements. The BOD5 for the saturated pyrene solution approximates over 80% of the COD value, suggesting that pyrene in its dissolved form is amenable to biodegradation, albeit in small quantity. The aqueous phase COD from the ozonated batch reactor increased after ozon... |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen at 325℃; for 5h; | 19 Example 19The process of Example 18 was repeated using the same equipment, pressure, and temperature except the catalyst was Grace-Davidson AT 535 catalyst (5 g) and crude soybean oil from Perdue Farms (50 g) was used. The catalyst was sulfided, as described hereinabove. The reaction products were analyzed by GC-FID to obtain the following linear paraffin distribution by weight: C18+=2.0%, C18=78.0%, C17=8%, C16=10%, C15=1.1%, C14=0.2%, C13=0.2%, C12=0.1%, C11=0.1%, C7-10=0.3%. The C18:C17 ratio is approximately 9.75, and C16:C15 ratio is greater than 9. | |
With hydrogen at 325℃; for 5h; | 20 Example 20The process of Example 19 was repeated using the same equipment, pressure, and temperature except Grace-Davidson AT 792 catalyst (5 g,) was used. The catalyst was sulfided, as described hereinabove. The reaction products were analyzed by GC-FID to obtain the following linear paraffin distribution by weight: C18+=1.8%, C18=82.4%, C17=3.3%, C16=11.2%, C15=0.5%, C14=0.2%, C13=0.1%, C12=0.1%, C11=0.1%, C7-10=0.3%. The C18:C17 ratio is approximately 25, and C16:C15 ratio is greater than 22. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 300℃; | 2 Example 2Soybean oil (50 g) and the catalyst used in Example 1 were placed in a 400 cc agitated pressure reactor. The reaction was run at 300° C. and the catalyst contained USY zeolite powder (0.125 g, type EZ-190, available from Engelhard (now part of BASF), Si/Al=3.05) physically mixed in. The reaction contents were weighed (51 g). The sample was base transesterified. IR showed the sample to be pure hydrocarbon with a trace of ester. A proton NMR analysis showed that the ester impurity was minute (<100 ppm). A GC-FID analysis gave the following linear paraffin (hydrocarbon) product distribution by weight: C18+=1%, C18=2%, C17=78%, C16=3%, C15=11%, C14=1%, C14-=4%. Some branching (<0.5 wt % isoheptadecane, “iso-C17” was observed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 300℃; | 4 Example 4Example 2 was repeated using the same equipment, pressure and temperature conditions. The reactants were the same as in Example 2, but different amounts were used (100 g soybean oil, 5 g Ni 55/5 P catalyst, and 0.5 g of USY zeolite powder, type EZ-190). A GC-FID analysis gave the following product distribution by weight: n-C18 acid (octadecanoic acid)=56%, n-C18=9%, n-C17=29%, iso-C17=1%, n-C16=1%, n-C15=4%. The Example shows that the addition of zeolite catalyst results in isomerized product, with low, 10% zeolite present. | |
With hydrogen at 325℃; for 5h; | 11 Example 11Example 10 was repeated using the same equipment, reaction conditions, procedures and the reactant (50 g), except for different hydrotreating catalyst (5 g, alumina-supported pre-sulfided nickel/molybdenum bi-metallic hydrotreating catalyst, CRI DN-3330, commercially available Criterion Catalysts and Technologies, Houston, Tex.). A GC-FID analysis of the product gave the following linear paraffin (hydrocarbon) product distribution by weight: C18+=1%, C18=73%, C17=12%, C16=10%, C15=1.5%. There was also 2.5% of n-octadecanoic acid in the product. The C18:C17 ratio is over 6 and C16:C15 ratio is over 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 300℃; | 3 Example 3The process of Example 2 was repeated using the same equipment, pressure and temperature conditions, and the reactants except for the catalyst and no zeolite was added. The catalyst used was reduced nickel powder (45 wt % Ni metal, 24 wt % NiO catalyst on zirconia and kieselguhr (E-473P, 2.5 g, available from BASF Catalysts, Houston, Tex., USA). The reaction products were weighed (51 g). An IR spectrum showed no ester in the sample. A GC-FID analysis gave the following linear paraffin (hydrocarbon) distribution by weight: C18+=1%, C18=2%, C17=84%, C16=1%, C15=11%, C14-=1%. Branching was not observed. | |
With hydrogen at 325℃; for 5h; | 10; 12; 13 Example 10 Soybean oil from Sigma-Aldrich, 50 g, and alumina-supported pre-sulfided cobalt/nickel/molybdenum tri-metallic hydrotreating catalyst (5 g, CRI DC2318, commercially available Criterion Catalysts and Technologies, Houston, Tex.) were placed in a 210 cc agitated pressure reactor. The vessel was leaked check with nitrogen. The headspace of the reactor was purged with nitrogen 10 times by pressurizing to 90 psig (722 kPa) and depressurizing to 0 psig (101 kPa). The reactor was then purged with high purity hydrogen (99.9% min., commercially available from Air Products, Allentown, Pa.) five times, and pressurized to 1000 psig (7000 kPa) with hydrogen. The reactor and its contents were agitated and heated to 325° C. (617° F.). The hydrogen pressure was increased to 2000 psig (13,900 kPa), and maintained there for 5 hours. The headspace was filled with fresh hydrogen to 1500-1700 psig (11,800 kPa) if the pressure dropped below 1000 psig (7000 kPa).The reactor contents were then cooled to below 50° C. (122° F.), the headspace was vented, and the contents were discharged to a glass bottle. The contents were weighed (51 g). IR and 1H NMR analysis showed no evidence of mono-, di- and triglycerides. The sample was then analyzed using GC-MS (peak identification) and GC-FID (species quantification) to show that the sample was converted to the following linear paraffins (hydrocarbons) by weight: C18+=1%, C18=81%, C17=6%, C16=11.5%, C15=0.5%. The C18:C17 ratio is greater than 13:1 and C16:C15 ratio is greater than 20:1.; Example 12Catalyst (5 g, CRI DC2318), temperature and pressure conditions were repeated from Example 10 except crude soybean oil (50 g, obtained from Perdue Farms, Salisbury, Md.) was used. The reaction products were analyzed by GC-FID to obtain the following linear paraffin (hydrocarbon) distribution by weight: C18+=0.5%, C18=80%, C17=7%, C16=11.6%, C15=0.9%. The C18:C17 ratio is greater than 11:1 and C16:C15 ratio is greater than 12:1.; Example 13Catalyst (5 g, CRI DC2318), temperature and pressure conditions were repeated from Example 10 using the same equipment, pressure, and temperature, except for a refined, bleached, and deodorized soybean oil sample (50 g, obtained from Perdue Farms, Salisbury, Md.) was used. The reaction products were analyzed by GC-FID to obtain the following linear paraffin (hydrocarbon) distribution by weight: C18+=0.5%, C18=79%, C17=8%, C16=11.3%, C15=1.2%. The C18:C17 ratio is almost 10, and C16:C15 ratio is greater than 9. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen at 325℃; for 5h; | 18 Example 18The process of Example 13 was repeated using the same equipment, pressure, temperature, and catalyst (5 g), except a 50:50 chicken fat to soybean oil mixture (50 g, mixed in-house with chicken fat and soybean oil obtained from Perdue Farms of Salisbury, Md.) was used. The reaction products were analyzed by GC-FID to obtain the following linear paraffin (hydrocarbon) distribution by weight: C18+=2.1%, C18=69.6%, C17=7.2%, C16=18.5%, C15=1.9%, C14=0.5%, C13=0.1% C12=0.1%. The C18:C17 ratio is approximately 9.7, and C16:C15 ratio is greater than 2.5. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen at 325℃; for 5h; | 15 Example 15The process of Example 13 was repeated using the same equipment, pressure, temperature, and catalyst (5 g), except palm oil (50 g, manufactured by T.I. International Ghana Ltd. of Accra, Ghana) was used. The reaction products were analyzed by GC-FID to obtain the following linear paraffin (hydrocarbon) distribution by weight: C18+=0.5%, C18=46.5%, C17=5%, C16=43%, C15=4%, C14=1%. The C18:C17 ratio is greater than 9, and C16:C15 ratio is greater than 10. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen at 325℃; for 5h; | 16 Example 16The process of Example 13 was repeated using the same equipment, pressure, temperature, and catalyst (5 g), except chicken fat (50 g, obtained from Perdue Farms of Salisbury, Md.) was used. The reaction products were analyzed by GC-FID to obtain the following linear paraffin (hydrocarbon) distribution by weight: C18+=1%, C18=60%, C17=7%, C16=28%, C15=3%, C14=1%. The C18:C17 ratio is approximately 9, and C16:C15 ratio is greater than 9. |
Yield | Reaction Conditions | Operation in experiment |
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98% | With N,N,N,N,-tetramethylethylenediamine; cobalt(II) chloride; lithium iodide In tetrahydrofuran at 10℃; for 1h; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With 5% Pd-BaSO4; hydrogen In hexane at 270℃; for 9h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
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95 %Chromat. | Stage #1: pentadec-1-yne With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 20℃; for 0.25h; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane at 80℃; Inert atmosphere; chemoselective reaction; | |
99 %Spectr. | With potassium <i>tert</i>-butylate; hydrogen; C15H20BrMnNO3P In 1,4-dioxane at 100℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
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In deuteromethanol | 2.1.2. Preparation of urea inclusion compounds General procedure: The urea inclusion compounds were prepared by slowly cooling warm solutions of the guest molecules n-decane, n-pentadecane, n-hexadecane, 1-fluorodecane, decanoic acid, dodecanedioic acid, sebacic acid with urea or urea-d4 in methanol or methanol-d1, respectively. The white needles were filtered, washed with 2,2,4- trimethylpentane, and dried. |
Yield | Reaction Conditions | Operation in experiment |
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In methanol | 2.1.2. Preparation of urea inclusion compounds General procedure: The urea inclusion compounds were prepared by slowly cooling warm solutions of the guest molecules n-decane, n-pentadecane, n-hexadecane, 1-fluorodecane, decanoic acid, dodecanedioic acid, sebacic acid with urea or urea-d4 in methanol or methanol-d1, respectively. The white needles were filtered, washed with 2,2,4- trimethylpentane, and dried. |
Yield | Reaction Conditions | Operation in experiment |
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1: 30.9% 2: 10.5% | With MnO2 supported on zirconium(IV) oxide at 340℃; for 3h; | |
1: 26.7% 2: 5.2% | at 300℃; for 4h; Sealed vial; Inert atmosphere; | 1.40 Catalyst Screening: High throughput catalyst screening for thedecarboxylation of free fatty acids was conducted using a high-temperature batch 24-well reactor made by Symyx. The 24 vials were loaded with catalyst and free fatty acid feedstock, in a 2 to 1 weight ratio. The vials were sealed under a nitrogen atmosphere with a Kapton-backed graphite sheet. Once loaded into the high temperature reactor and sealed, the reactor headspace was pressurized with 40 psig nitrogen to discourage leaking of the individual vials. The reactor was placed into a stationary furnace and heated to 300°C for 4 hours. After completion the reactor was removed from the furnace and allowed to cool to room temperature.Analytical work-up of each sample involved BSTFA/pyridine derivatization, which was carried out as follows. The sample was diluted with chloroform containing 1 mg/mL heptadecanoic acid as an internal standard, mixed well, and centrifuged. A 500 μ^ aliquot was removed and added to a 2 mL vial. To this second vial was added 500 μ^ of N,0-bis[trimethylsilyl]trifluoroacetamide(BSTFA) and 500 μ^ of pyridine. The vial was mixed well, capped, and heated to 70°C for 1 hour. GC-FID and GC-MS were utilized for quantification and identification of the product mixture. Analysis was performed using a DB5-HT column (15 m x 250 μιη x 0.10 μιη nominal film thickness). The injector was held at 340°C with a 150: 1 split. With a flow rate of 2 mL/min H2, the column was heated from 80°C to 350°C at 25°C/min and then held at 350°C for 9.2 min. |
Yield | Reaction Conditions | Operation in experiment |
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1: 22% 2: 30% | With Selectfluor In acetone at 120℃; for 2h; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
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65% | With palladium 10% on activated carbon; hydrogen; acetic acid; lanthanum(lll) triflate at 200℃; for 15h; | 11 Example 11: Preparation of n-pentadecane Example 11: Preparation of n-pentadecane[0093] Compound 3 (0.25g) was combined in acetic acid (1 mL) with Pd/C (10 % by wt Pd, 0.250 g), La(OTf)3 (0.200 g) and placed in a sealed vessel under H2 pressure (100 psi). The vessel was heated to 200 °C for 15 hours. At this time the heating source was removed and the vessel allowed to cool to room temperature. The suspension was removed from the vessel and diluted with dichloromethane and 2-propanol and filtered to remove the catalyst. The solvent was removed under vacuum and redissolved in benzene-d6. The pressure was released and reaction mixture extracted from the vessel with methylene chloride (2 x 2 mL) and water (2 x 2 mL). The combined layers were filtered and the organic layer separated, dried over NaS04 and solvent removed in vacuo to yield pentadecane as a colorless oil (65 % isolated yield) as confirmed by GC-MS. XH NMR (400 MHz, CDC13) ? 1.27 (m, 26H), 0.88 (m, 6H). 13C NMR (101 MHz, CDCI3) ? 32.09, 29.87, 29.53, 22.82, 14.15. |
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; acetic acid / 12 h / 100 °C / 760.05 Torr 2: lanthanum(lll) triflate; hydrogen / 14 h / 200 °C / 15514.9 Torr | ||
Multi-step reaction with 2 steps 1: air / 3 h / 100 °C 2: palladium on activated charcoal; hydrogen; dimethylsulfone; lanthanum(lll) triflate / acetic acid / 16 h / 200 °C / 25877.6 Torr / Sonication; Autoclave |
Yield | Reaction Conditions | Operation in experiment |
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65% | With hydrogen; lanthanum(lll) triflate at 200℃; for 14h; | 12 Exam le 12: Stepwise preparation of n-pentadecane Exam le 12: Stepwise preparation of n-pentadecaneUnsaturated C15 precursor (250 mg, 1.00 mmol) was dissolved in glacial acetic acid (15 mL) and added to a round bottom flask containing Pd/C (125 mg of 10 wt % Pd/C, 0.120 mmol Pd, 12 mol % Pd relative to substrate). The mixture was put under 1 atmosphere of ? and heated at 100 °C for 12 hours to yield a pale yellow solution of pentaketone as confirmed by NMR (XH NMR (400 MHz, CDC13) ? 2.73 (m, 16 H), 2.18 (s, 6 H). 13C NMR (101 MHz, CDC13) ? 207.93, 207.88, 207.18, 36.97, 36.1 1, 36.06, 36.02, 29.85).The solution was transferred to a stainless steel pressure reactor with La(OTf)3 (170 mg, 0.290 mmol) pressurized with 300 psi H2 and heated to 200 °C for 14 hours. Upon cooling, the pressure was released and reaction mixture extracted from the vessel with methylene chloride (2 x 2 mL) and water (2 x 2 mL). The combined layers were filtered and the organic layer separated, dried over NaS04 and solvent removed in vacuo to yield pentadecane as a colorless oil (97 mg, 65 %) as confirmed by GC-MS. XH NMR (400 MHz, CDC13) ? 1.27 (m, 26H), 0.88 (m, 6H). 13C NMR (101 MHz, CDC13) ? 32.09, 29.87, 29.53, 22.82, 14.15. |
65% | With dimethylsulfone; palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In acetic acid at 200℃; for 16h; Sonication; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 275℃; under 15001.5 Torr;Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.3%; 13.8% | With hydrogen; In decane; at 260℃; under 7500.75 Torr; for 4h;Autoclave; | 51.2 mg of palmitic acid, 42.5 mg of the catalyst 1 and 2 mL of decane were weighed, placed in an autoclave (model TVS-N 2 manufactured by Taiatsu techno corp.), and it was heated with a metal bath (manufactured by Koike precision instruments) while stirring with a magnetic stirrer under a hydrogen atmosphere. The reaction was conducted for 4 hours at a temperature of 260 C and a pressure of 1 MPa. (Analysis of Product) After the reaction, an internal standard substance (dodecane) was added to the reaction solution and the conversion (yield) (%) with respect to the raw material was derived by gas chromatographic analysis. The yield with respect to the raw material pentadecane, which is a linear hydrocarbon (B), was 69.3%, and the yield with respect to the raw material hexadecane, which is a linear hydrocarbon (A), was 13.8%. The molar ratio (B / A) was 5.0 |
72%Chromat.; 22.3%Chromat. | With hydrogen; In dodecane; at 280℃; under 30003 Torr; for 8h;Autoclave; | General procedure: The conversion of fatty acids was operated in stainless reactors(50 mL) that purchased from Anhui Kemi Machinery Technology Co.,Ltd. For a typical procedure, stearic acid (0.5 mmol), heterogeneous catalyst (100 mg), and alkane solvent (20 mL) were loaded into a quartzlining in the reactor. The reactor was then purged with hydrogen for three times, and then purged with 4 MPa H2 at room temperature. The reaction was set at reaction temperature for 8 h with a stirring speed of800 rpm. After reaction, the gaseous phase was analyzed by gas chromatography (GC). A Shin Carbon ST 80/100 packed column (Restek) and a thermal conductivity detector (TCD) were used to determine the yields of H2, CO, CO2 and CH4. A Plot Q column and a flame ionization detector (FID) were used to determine the yields of gaseous hydrocarbons such as CH4, C2H6, and C3H8. The liquid products were collected, and eicosane (0.5 mmol) was added as internal standard. The products were analyzed using both gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). GC-MS analysis was conducted by an Agilent 7890B Gas Chromatograph equipped with aHP-5MS 30m ×0.25mm×0.25 mum capillary column (Agilent). The GC was directly interfaced to an Agilent 5977 mass selective detector (EI, 70 eV). A typical GC oven temperature program were listed as follows: 210 C hold for 2 min, ramp 20 C min-1 to 300 C and hold for 2 min. Representative GC spectra are shown in supporting information (Figs. S1 and S2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.3%Chromat.; 22.8%Chromat. | With hydrogen; In dodecane; at 280℃; under 30003 Torr; for 8h;Autoclave; | General procedure: The conversion of fatty acids was operated in stainless reactors(50 mL) that purchased from Anhui Kemi Machinery Technology Co.,Ltd. For a typical procedure, stearic acid (0.5 mmol), heterogeneous catalyst (100 mg), and alkane solvent (20 mL) were loaded into a quartzlining in the reactor. The reactor was then purged with hydrogen for three times, and then purged with 4 MPa H2 at room temperature. The reaction was set at reaction temperature for 8 h with a stirring speed of800 rpm. After reaction, the gaseous phase was analyzed by gas chromatography (GC). A Shin Carbon ST 80/100 packed column (Restek) and a thermal conductivity detector (TCD) were used to determine the yields of H2, CO, CO2 and CH4. A Plot Q column and a flame ionization detector (FID) were used to determine the yields of gaseous hydrocarbons such as CH4, C2H6, and C3H8. The liquid products were collected, and eicosane (0.5 mmol) was added as internal standard. The products were analyzed using both gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). GC-MS analysis was conducted by an Agilent 7890B Gas Chromatograph equipped with aHP-5MS 30m ×0.25mm×0.25 mum capillary column (Agilent). The GC was directly interfaced to an Agilent 5977 mass selective detector (EI, 70 eV). A typical GC oven temperature program were listed as follows: 210 C hold for 2 min, ramp 20 C min-1 to 300 C and hold for 2 min. Representative GC spectra are shown in supporting information (Figs. S1 and S2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 400℃; under 750.075 Torr; for 1.0h;Flow reactor; | General procedure: Hydrocarbons were synthesized in a steel flowreactor with an inner diameter of 10 mm. Prior to testing, the FT catalyst as part of the multicomponent bedwas activated in a hydrogen stream supplied at a spacevelocity of 3000 h-1 at 400 and 0.1 MPa for 1 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane Reflux; | 2.d d. Synthesis of (4R,5S)-4-((E)-pentadec-1-en-1-yl)-2-phenyl-1,3-dioxan-5-ol (4R,5S)-2-phenyl-4-vinyl-1,3-dioxan-5-ol (6 g, 29 mmol) and n-pentadecane (9.2 g, 43.8 mmol) was dissolved in 5-100 mL dichloromethane and Grubbs II catalyst (250 mg, 2.9 mmol) was added and heated to reflux until (4R,5S)-2-phenyl-4-vinyl-1,3-dioxan-5-ol disappeared completely and concentrated to give 8.5 g (4R,5S)-4-((E)-pentadec-1-en-1-yl)-2-phenyl-1,3-dioxan-5-ol in 75% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pd-Cu/hydrotalcite at 230℃; for 3h; Sealed tube; | 16 The reaction in this Example using 1-octanol was repeated in accordance with the reaction scheme below to further compare the effects of impregnating HT on carbon support. The following reaction was performed using (i) Pd-Cu/HT, with a 3:1 molar ratio of Mg:Al in the HT; and (ii) Pd-Cu/5% HT/C, with a 4:1 molar ratio of Mg:Al in the HT. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3:1 Pd-Cu/hydrotalcite at 230℃; for 3h; Sealed tube; | 16; 10.4 Reaction with 1-Octanol General procedure: This Example demonstrates the effect of various hydrotalcite catalysts on decarbonylation in the Guerbet reaction of 1-octanol. The reaction was performed according to the procedure described in Example 1 above and in accordance with the conditions in the reaction scheme above, using the following: 1-octanol (3 mmol), the catalyst described in Table 10 below (100 mg). Selectivity was determined by GC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pd/hydrotalcite/C at 230℃; for 3h; Sealed tube; | 16; 10.5 Reaction with 1-Octanol General procedure: This Example demonstrates the effect of various hydrotalcite catalysts on decarbonylation in the Guerbet reaction of 1-octanol. The reaction was performed according to the procedure described in Example 1 above and in accordance with the conditions in the reaction scheme above, using the following: 1-octanol (3 mmol), the catalyst described in Table 10 below (100 mg). Selectivity was determined by GC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In n-heptane at 219.84℃; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In n-heptane at 199.84℃; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In n-heptane at 199.84℃; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Microwave irradiation; | General procedure: The experiments were carried out on the setup detailed in [12, 13] and sketched in Fig. 1. It includes a microwave generator, a circulator, a water attenuator, a directional coupler, a spectrum analyzer, and an oscilloscope. The attenuator males it possible to get a smoothly varying forward power in the range from100 W to 2.5 kW. The discharge section is a waveguide to-coaxial adapter, the center conductor of which serves as an antenna for introducing microwave energy into the discharge section. A movable short plunger was used for matching. The central electrode of the coaxial line is made of copper tubing with an outer diameter of 1.5 mm. Reducing the diameter of the antenna made it possible to organize a discharge with a forward power on the order of 100 W. The discharge was excited at the end of the antenna in a quartz cell (of a 55 mm diameter) placed in a protective screen. The cylindrical quartz cell was partially filled with a hydrocarbon, and it was blown with argon above the surface of the liquid for 2 min. By applying microwave power, the antenna end heats up, the hydrocarbon evaporates, and a discharge is initiated in its vapor inthe liquid volume. No additional energy source required for initiation.The discharge was initiated in the region of the maximum microwave field at the end of the central conductor of the coaxial line (Fig. 2) in various hydrocarbons differing in structure and boiling point (seeTable 1): n-heptane, octane, isooctane, decane, pentadecane,hexadecane, cyclohexane, benzene, toluene,ortho-xylene, and Nefras S2 80/120. The liquids used were not deaerated prior to the experiments. The volume of the liquid in the cell was about 40 mL, ensuring that the end of the internal electrode of the coaxial line (antenna) would be below the liquid surface. No auxiliary gases were supplied through the channel in the central electrode. The pressure above the surface of the liquid was equal to atmospheric pressure.The composition of the main gaseous products (H2, C2H2, CH4, C2H4) of the discharge in liquid hydrocarbons was studied using an LKhM-8 chromatograph with a thermal conductivity detector and aHaySep S-packed chromatographic column. The instrument was equipped with a digital data acquisition and processing system (ADC and the software suite Phoenix). Nitrogen was used as the carrier gas. The absolute calibration of the instrument was carried out using individual components and ready-made calibration gas mixtures. An Agilent syringe was used for sampling in both cases. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nickel 2-ethylhexanoate; TOP; hydrogen In benzene at 350℃; for 6h; Autoclave; | Catalyst synthesis and catalytic activity runs. General procedure: Thecalculated amount of precursors (0.0436 mmol ofcobalt(II) or nickel(II) 2-ethyl hexanoate and0.0872 mmol of trioctylphosphine, respectively), substrate(0.218 mmol of stearic or palmitic acid), solvent(3 g of benzene), and a magnetic stirrer were placed ina 45-cm3 stainless steel autoclave. The autoclave was pressurized, filled with hydrogen to a pressure of5MPa, and placed in an oven. The reaction was carried out under vigorous stirring at 350°C for 3 and 6 h.Temperature was controlled using a thermocouple.Upon completion of the reaction, the autoclave was cooled and the gas was passed through a KMnO4 solution.Afterwards, the autoclave was depressurized. The reaction products were separated from the resulting catalyst via centrifugation and analyzed by gas chromatography methods using a flame ionization detector(GC-FID) and a mass spectrometric detector(GC-MS). The catalyst was washed with n-hexaneand ethanol and dried in a fume hood. After that, the catalyst was analyzed by X-ray powder diffraction(XRD) and X-ray photoelectron spectroscopy (XPS). | |
With hydrogen In dodecane at 280℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With hydrogen at 200℃; for 24h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogen at 200℃; for 24h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water-d2 at 20℃; for 1h; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With C66H84Ni; isoprene In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
105.9 mg | Stage #1: C22H38N2O2S With sodium tetrahydroborate In methanol; dichloromethane at 0 - 20℃; Stage #2: With sodium hydroxide In methanol; dichloromethane; water at 20℃; for 24h; |
Tags: 629-62-9 synthesis path| 629-62-9 SDS| 629-62-9 COA| 629-62-9 purity| 629-62-9 application| 629-62-9 NMR| 629-62-9 COA| 629-62-9 structure
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