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CAS No. : | 629-59-4 | MDL No. : | MFCD00008986 |
Formula : | C14H30 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BGHCVCJVXZWKCC-UHFFFAOYSA-N |
M.W : | 198.39 | Pubchem ID : | 12389 |
Synonyms : |
n-Tetradecane
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 69.41 |
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) : | -2.4 cm/s |
Log Po/w (iLOGP) : | 4.23 |
Log Po/w (XLOGP3) : | 7.2 |
Log Po/w (WLOGP) : | 5.71 |
Log Po/w (MLOGP) : | 5.93 |
Log Po/w (SILICOS-IT) : | 5.33 |
Consensus Log Po/w : | 5.68 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.88 |
Solubility : | 0.00262 mg/ml ; 0.0000132 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -7.02 |
Solubility : | 0.0000188 mg/ml ; 0.0000000949 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.52 |
Solubility : | 0.000605 mg/ml ; 0.00000305 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 2.04 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P285-P301+P310-P342+P311 | UN#: | 2810 |
Hazard Statements: | H304-H315-H319-H334-H335 | 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; methyl cyclohexane at 200℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogen In hexane at 160℃; for 18h; Molecular sieve; chemoselective reaction; | |
89% | With hydrogen In neat (no solvent) at 250℃; for 24h; Autoclave; High pressure; | |
30.14% | With Hexadecane; hydrogen at 50 - 200℃; Sealed tube; Inert atmosphere; | 8 Example 8 Selective Hydrodeoxygenation of Myristic Acid to Tetradecane in a 20-cc Multi-Reactor System [0136] This Example describes the selective hydrodeoxygenation of myristic acid to tetradecane using the alumina-supported tungsten/platinum catalyst prepared in Example 1 (2% W on 5% Pt/alumina). This process was carried out under the conditions described in Example 3. The results of this reaction, which was done in duplicate, are listed in Table 6. [TABLE-US-00006] TABLE 6 Molar Selectivity and Molar Yield of Tetradecane from the Conversion of Myristic Acid Using Pt/W/Alumina Catalysts Myristic Acid Tetradecane Catalyst Conversiona Selectivityb Yield 2% W on 5% Pt 57.51% 52.41% 30.14% on alumina 2% W on 5% Pt 49.28% 53.05% 26.14% on alumina aPercent moles of myristic acid that converted to products. bPercent moles of myristic acid that converted into tetradecane. [0137] The results in Table 6 demonstrate that a hydrodeoxygenation process employing a W/Pt/alumina catalyst under conditions of low temperature and pressure can be used to produce a linear alkane from the C14 oxygenate, myristic acid. Thus, the disclosed process can be used to hydrodeoxygenate oxygenates of various carbon chain lengths. |
With phosphorus; hydrogen iodide | ||
With tris(pentafluorophenyl)borate In cyclohexane at 20℃; for 6h; Schlenk technique; Inert atmosphere; Green chemistry; | ||
99 %Chromat. | With hydrogen In neat (no solvent) at 230℃; for 48h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 5 % Chromat. 2: 29 % Chromat. | With copper In tetrahydrofuran at 25℃; for 0.166667h; | |
1: 29 % Chromat. 2: 5 % Chromat. | With copper In tetrahydrofuran at 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With manganese; copper dichloride In water for 16h; Ambient temperature; | |
60% | With pyridine; manganese; trifluoroacetic acid; cobalt(II) bromide In acetonitrile at 50℃; | |
With CuI*P(Et)3; lithium dihydronaphthylide radical 1. THF/DMF, 0 deg C; 2. 25 deg C; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen In dichloromethane at 65℃; for 18h; same yield with a similar catalyst; Pressure (range begins): 120 <unit not given>; | |
98% | With hydrogen In methanol at 20℃; for 2h; | |
96% | With 3-methyllumiflavin; oxygen; hydrazine hydrate In acetonitrile at 30℃; for 24h; |
93% | With oxygen; copper(l) chloride; hydrazine at 40℃; for 18h; | |
13% | at 310℃; for 3h; Other temperatures and other catalyst (FCHT); | |
With hydrogen at 239.9℃; | ||
73 % Chromat. | With triethylsilane In ethanol at 20℃; for 24h; | |
2 EXAMPLE 2 EXAMPLE 2 The charge similar to that given in example 1 was taken except that 1-tetradecene 10 cm3 (40.0 mmol) was taken instead of 1-octene. The reaction was completed in 26 minutes. The activity of this reaction was found to be 4.83*10-4 mol/s/g. Conversion of this reaction was found to be 99.6% and selectivity of 98.2% towards final product tetradecane. A similar reaction taken in absence of triphenylphosphine took 90 minutes to go to completion, which shows the activity of 2.85*10-4 mol/s/g. | ||
With hydrogen; Methylated β-cyclodextrin In water at 20℃; for 9h; | ||
With [2,2]bipyridinyl; hydrogen; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 2h; | 5 The reactions under atmospheric pressure are carried out at 20° C. 2 ml of colloidal rhodium(O) suspension is introduced into a 25 ml glass flask. The desired quantity of substrate that is to be hydrogenated is added to the reaction mixture (in general, 100 equivalents/metal). The flask is then connected to a 500 ml gas burette. The assembly is filled with hydrogen after having purged the system under vacuum. The unit is placed under vigorous stirring (1,500 min-1). The reaction is controlled by the volume of gas that is consumed and by gas phase chromatography. At the end of the reaction, the catalytic system is dispersed into 10 ml of CH3CN, centrifuged for 10 minutes (15,300 rpm-1; 20° C.). The sample is then analyzed by GPC. The results are grouped in Table 1 for different non-aromatic unsaturated substrates. | |
With hydrogen In water at 20℃; | ||
With C37H42N3O2Ru; hydrogen In chlorobenzene at 130℃; for 5h; Autoclave; | ||
With hydrogen In hexane at 20℃; | ||
With [η6-(2-phenoxyethanol)RuCl(2-(2-pyridyl)benzoxazole)]Cl; hydrogen In methanol at 25℃; for 1h; Autoclave; | Homogeneous experiments General procedure: experiments A typical procedure for the catalytic hydrogenation of alkenes was as follows. A Parr High pressure reactor with an in built cooling, heating and stirring systems was charged with styrene (0.56 mL,5.00 mmol), catalyst (5 mg, 0.01 mmol) and methanol (50 mL) andsealed. It was then evacuated, flushed with H2 three times and the pressure adjusted to 10 bar. The mixture was stirred at 500 rpm under constant hydrogen pressure for the duration of the reaction period. After the reaction time, the autoclave was vented and samples drawn for GC analyses. The samples were filtered using 0.45 m micro filters and the solutions analyzed by Varian CP-3800 GC (ZB-5HT column 30 m × 0.25 mm × 0.10 m). Commercial ethylbenzene was used as an authentic standard to determine the percentage conversion of styrene to ethylbenzene. Percentage conversions were determined by comparing the peak areas of ethylbenzene (product) and styrene substrate. | |
With hydrogen In water at 20℃; for 3h; Autoclave; | ||
With hydrogen In water at 30℃; for 1.5h; Autoclave; | ||
With riboflavin 2’,3’,4’,5’-tetraoctadecanoate; hydrazine hydrate at 30℃; for 4.5h; | ||
With rhodium(III) chloride trihydrate; 3C38H79N3O16*C18H15O9PS3; hydrogen In methanol at 80℃; for 0.25h; Inert atmosphere; Schlenk technique; Autoclave; | ||
With hydrogen In water at 30℃; for 63.3333h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodosylbenzene In benzene at 25℃; for 7h; other catalysts and regioselectivity investigated; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With cyclohexa-1,4-diene; 9-ethyl-N3,N3,N6,N6,-tetramethyl-9H-carbazole-3,6-diamine; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 23℃; for 36h; Inert atmosphere; UV-irradiation; Schlenk technique; | |
42% | With lithium-<cyano(triphenylphosphoranyliden)methyl>trihydroborate In tetrahydrofuran for 48h; Ambient temperature; | |
98 %Chromat. | With [((Me)NN2)NiCl]; diphenylsilane; sodium isopropylate In toluene for 6.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 326.9℃; 1.5E5 Pa; Yield given; | ||
Multi-step reaction with 2 steps 1.1: NaH; imidazole / tetrahydrofuran / 0.5 h / 20 °C 1.2: 95 percent / tetrahydrofuran / 0.5 h / 20 °C 2.1: 100 percent / (Bu4N)2S2O8; HCO2Na / dimethylformamide / 0.5 h / 50 °C | ||
Multi-step reaction with 2 steps 2: 18 percent / n-Bu3SnH, Et3B / benzene; hexane / 0.33 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium formate; (Bu4N)2S2O8 In N,N-dimethyl-formamide at 50℃; for 0.5h; | |
51% | With 2,2'-azobis(isobutyronitrile); tetraphenyldisilane In ethyl acetate for 16h; Heating; | |
18% | With triethyl borane; tri-n-butyl-tin hydride In hexane; benzene at 20℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 30% 2: 18% | With triethyl borane; tri-n-butyl-tin hydride In hexane; benzene at 20℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hydroxide; chloroamine In methanol; diethyl ether Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium tetrahydroborate In various solvent(s) at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In ethyl acetate | ||
With hydrogen In ethyl acetate for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium <i>tert</i>-butylate In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With di-tert-butyl peroxide at 140℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 300℃; for 3.5h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air Formation of xenobiotics; 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 |
---|---|---|
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 |
---|---|---|
80% | With buta-1,3-diene; copper dichloride In tetrahydrofuran at 30℃; for 48h; Schlenk technique; Inert atmosphere; | |
100 % Chromat. | With buta-1,3-diene; nickel dichloride In tetrahydrofuran at 0℃; for 0.5h; | |
98 % Chromat. | With 1-Phenylprop-1-yne; copper dichloride In tetrahydrofuran for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium methylate In methanol at 27℃; Electrochemical reaction; Pt anode; graphite cathode; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 1-methyl-1H-imidazole; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1-methyl-1H-imidazole; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1-methyl-1H-imidazole; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 86% 2: 2% | With silver(I) 4-methylbenzenesulfonate; ethylene dibromide In tetrahydrofuran at 20℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 63% 2: 25% | With benzophenone; potassium carbonate at 170℃; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 26 % Chromat. 2: 9 % Chromat. | In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 92 % Chromat. 2: 2 % Chromat. | In tetrahydrofuran at -30℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 94 % Chromat. 2: 4 % Chromat. | In tetrahydrofuran at -30℃; | |
1: 54 % Chromat. 2: 3 % Chromat. | In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dimethyldisulphide; hydrogen at 363℃; for 120h; | 1 Experiment 1; A liquid feed mixture of 69.74 wt% decalin (C10H18), 0.26wt% dimethyl disulphide (DMDS) and 30wt% tallow oil was prepared. The tallow oil comprised fatty acid chains with 12 to 20 carbon atoms (including the carboxyl carbon), the bulk of the molecules having 16 or 18 carbon atoms in the fatty acid chain (including the carboxyl carbon). The liquid mixture was fed to a reactor as illustrated in Figure 4, operating at 363°C and 30 barg (3.1 MPa) pressure, at a feed-rate of 60mL/hour. A cobalt-molybdenum on alumina catalyst was used. The liquid hourly space velocity (LHSV) of the liquid feed over the catalyst was 4 h-1. A flow of hydrogen was also fed to the reactor, such that the ratio of H2 gas volume to liquid feedstock volume was maintained at a value of 200 Nm3/m3 (gas volume at 15.6°C and 1 atm). Reaction was maintained over a period of 5 days. Liquid samples were collected daily and analysed according to a chromatographic method described in ASTM D2887, and also by GCMS. Gaseous off-gas samples were analysed using gas chromatography. The quantity of liquid product was determined gravimetrically. Off-gas volume was measured using a wet-test flow meter. The mass balance calculated from the quantities of the identified components of the obtained liquid and gaseous products was 99% with 1% standard deviation. The carbon balance was 100% with 1% standard deviation. |
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 |
---|---|---|
1: 51 % Chromat. 2: 31 % Chromat. 3: 10 % Chromat. 4: 2 % Chromat. | Stage #1: 1-bromo-butane With iodine; magnesium In diethyl ether at 60℃; for 1h; Stage #2: 1-bromo dodecane With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In diethyl ether at 20℃; for 0.25h; Further stages. Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64 % Chromat. | Stage #1: 1-bromo-butane With iodine; magnesium In diethyl ether at 60℃; for 1h; Stage #2: 1-bromo dodecane With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In diethyl ether at 20℃; for 0.25h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 32 percent / PPh3, Pd(acac)2 / dioxane / 168 h / Heating 2: H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 760 Torr | ||
Multi-step reaction with 2 steps 1: 32 percent / PPh3 / Pd(acac)2 / dioxane / 70 h / Heating 2: H2 / Pd-C / ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 30 percent / PPh3, Pd(acac)2 / dioxane / 65 h / Heating 2: H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 760 Torr | ||
Multi-step reaction with 2 steps 1: 30 percent / PPh3 / Pd(acac)2 / dioxane / 65 h / Heating 2: H2 / Pd-C / ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 30 percent / PPh3, Pd(acac)2 / dioxane / 65 h / Heating 2: H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 760 Torr | ||
Multi-step reaction with 2 steps 1: 32 percent / PPh3, Pd(acac)2 / dioxane / 168 h / Heating 2: H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 760 Torr | ||
Multi-step reaction with 2 steps 1: 30 percent / PPh3 / Pd(acac)2 / dioxane / 65 h / Heating 2: H2 / Pd-C / ethyl acetate |
Multi-step reaction with 2 steps 1: 32 percent / PPh3 / Pd(acac)2 / dioxane / 70 h / Heating 2: H2 / Pd-C / ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia In silica gel; N,N-dimethyl-formamide | 1 Example 1 Example 1 A 50 ml, round-bottomed flask dried in a dryer at 100° C. was purged with a dry nitrogen treated with molecular sieves 4A, and then 10 ml of N,N-dimethylformamide dried beforehand with molecular sieves 4A4A, 0.10 g of n-tetradecane (an internal standard substance for gas chromatography), and 97.6 mg (0.30 mmol; 3.4 mol % based on oxime) of p-toluenesulfonic anhydride were added thereto, followed by stirring under heating at 110° C. for 10 minutes. Then, a solution of 1.00 g (8.84 mmol) of cyclohexanone oxime dissolved in 10 ml of N,N-dimethylformamide was added thereto and the reaction was carried out at 110° C. for 15 minutes. After completion of the reaction, the reaction solution was treated with a commercial aqueous solution of 28% NH3 to deactivate the catalyst. The reaction solution after the deactivation was analyzed by gas chromatography. The result showed that the yield of ε-caprolactam is 85.9% and the value of TON is 25.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With methanesulfonic acid | 6 EXAMPLE 6 EXAMPLE 6 A mixture of 100 mg (0.34 mmol) of 2'-(2'-hydroxy-4-methylphenyl)-2',4',4',7'-tetramethylchroman, 2.0 mL of m-cresol, 23.9 mg of methanesulfonic acid, and 100.7 mg of tetradecane as an internal standard was heated under sealed conditions at 150° C. for 21.5 hours. Based on the above-described gas chromatographic and workup procedures, there was obtained about a 90% yield of crude 3,6,9,9-tetramethylxanthene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With methanesulfonic acid In acetone | 1 EXAMPLE 1 EXAMPLE 1 A mixture of 2 mL (19.1 mmol) of m-cresol, 172 mg (2.96 mmol) of acetone, and 16.8 mg (0.17 mmol) of methanesulfonic acid was heated under sealed conditions at 150° C. for 21 hours. The mixture was assayed by quantitative gas chromatography using tetradecane as an internal standard. There was obtained 514 mg (73% yield) of 3,6,9,9-tetramethylxanthene and 17 mg of 4,4,4'4'7,7'-hexamethyl-2,2'-spirobichroman. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With CO; KF In ethanol | 6 EXAMPLE 6 STR7 EXAMPLE 6 STR7 Into a 10 ml stainless steel autoclave, 1,8-diiodo-3,3,4,4,5,5,6,6-octafluorooctane (128 mg, 0.25 mmol), Co2(CO)8 (8.5 mg, 0.0025 mmol), KF (58 mg, 1 mmol) and ethanol (1 ml) were charged, and CO (50 atm) was sealed in. The mixture was reacted at 100° C. for 24 hours. As an internal standard, n-tetradecane (20 μl, 0.077 mmol) was added, and the product was quantitatively analyzed by gas chromatography, whereby it was found that diethyl 4,4,5,5,6,6,7,7-octafluoro-1,10-decanedioate was produced in a yield of 64%. The product was isolated and purified by silica gel column chromatography. Anal. Calcd for C14 H18 F8 O4. C: 41.80, H: 4.51. found C: 41.66, H: 4.58. IR (neat) 1738 cm-1 (νC=O). 1 H-NMR (CDCl3,TMS) δ1.26 (t,J=7Hz,6H), 2.1-2.95 (m,8H), 4.18 (q,J=7Hz,4H). 19 F-NMR (CDCl3,CFCl3) δ-113.9 (br,4F), -122.7 (br,4F). Mass m/e (rel. int.) 402 (M+, 6), 357 (60), 329 (31), 284 (5), 55 (53), 45 (16), 29 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | In tetrahydrofuran | 32 Preparation of 3,3-Dimethyloxetane from 2,2-Dimethylpropane-1,3-diol Sodium Monosulfate EXAMPLE 32 Preparation of 3,3-Dimethyloxetane from 2,2-Dimethylpropane-1,3-diol Sodium Monosulfate A 3-neck, 500-mL round bottom flask equipped with a reflux condenser, magnetic stir bar and argon inlet was charged with potassium hydride (2.0 g, 80 mmol), tetrahydrofuran (75 mL) and 2,2-dimethylpropane-1,3-diol sodium monosulfate (9.4 g, 72 mmol). The reaction mixture was heated at reflux for 4 h. Removal of the solvent by distillation gave the alkoxide salt of the monosulfate. Tetradecane (50 mL) was added to the solids, and the slurry was heated at 120° C. The distillate was collected in a Dean-Stark trap to give 3,3-dimethyloxetane (1.0 g, 20% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; carbon monoxide; In chlorobenzene; | EXAMPLE 2 Preparation of p-Chlor-(alpha,alpha,alpha-Trifluoro-o-tolyl) Isocyanate A solution of 0.67 g (0.0039 moles) of palladium dichloride, 0.60 g (0.0076 moles) pyridine, 8.59 g (0.038 moles) of p-chloro-alpha,alpha,alpha-trifluoromethyl-nitrobenzene and 1.0040 g of tetradecane as an internal standard in 75 ml of dry chlorobenzene was placed in a 300 ml Hastelloy C autoclave. After flushing with argon and carbon monoxide, the clave was charged with 2000 psi (13,790 KPa) of carbon monoxide and heated to 200 C. At 200 C., the pressure was increased to 3000 psi (20,684 KPa) carbon monoxide and maintained at this temperature and pressure for four hours. A sample was withdrawn and analyzed by gas chromatography. This analysis showed that the solution contained 0.42 g (95% conversion) of p-chloro-alpha,alpha,alpha-trifluoromethylnitrobenzene and 7.46 (93% selectivity) of p-chloro-alpha,alpha,alpha-trifluoro-o-tolyl isocyanate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sulfuric acid In ethyl acetate; N,N-dimethyl-formamide | 23 EXAMPLE 23 STR27 EXAMPLE 23 STR27 330 mg (1.9 mmols) of a mixture of gernayl chloride, neryl chloride and linalyl chloride (ratios=61:32:7), 24.3 mg (0.25 mmols) of copper(I) chloride, 0.82 g (6.0 mmols) of triethylamine N-oxide (water content of 14%), and 3 ml of N,N-dimethylformamide were mixed and agitated at 45° C. for 2 hours. 15 ml of ethyl acetate and 8 ml of 2% sulfuric acid were added to the mixture and shaked sufficiently to extract an organic matter. The organic phase was collected, to which 145 mg of n-tetradecane was added, followed by subjecting to gas chromatography. As a result, it was found that starting geranyl chloride, neryl chloride and linalyl chloride disappeared with citral being formed at a yield of 67%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With H2 | 8 EXAMPLE 8 EXAMPLE 8 Two grams of catalyst is charged into an autoclave with 35 grams of 7-tetradecene. The reactor is purged 5 times to 300 psig with pure hydrogen and vented back to 0 psig. The autoclave is then heated to 110° C. and pressured to 950 psig H2 at the temperature. After an appropriate period of reaction time analysis of the autoclave contents reveal significant conversion of 7-tetradecene to n-tetradecane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
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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90% | With piperidine; silica gel In methanol; acetonitrile Electrolysis; cooling; | |
95 %Spectr. | With pyridine; potassium hydroxide In methanol; cyclohexane; acetonitrile Electrolysis; | 4.1. Kolbe-couplings with cyclohexane General procedure: Carboxylic acids (2.5 mmol) were added to electrolyte solutions (20 mL) using potassium hydroxide as a supporting electrolyte (saturated) in the presence of the cycloalkanes. The undivided reaction cell was capped with a septum equipped with platinum electrodes (10 mm×20 mm). The electrolysis was then performed at constant current. After completion of the reaction, the cycloalkane phase was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using n-hexane-EtOAc to give products. The products' yields were determined by NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 89% 2: 2.1% | With hydrogen at 240℃; for 12h; | 1 1000 grams of 1-tetradecanol (4.7 mol; Lorol C 14 from Cognis) were introduced into a stirrable pressure vessel with 10 grams of a nickel catalyst (Ni-5249 P from Engelhard; Ni content=63% by weight) and heated to 240° C. Hydrogen was then added over a period of 12 hours under a pressure of 20 bar through a gas dispersion tube and, at the same time, the reaction gases were removed through a valve in the lid of the reactor. The product was then cooled, drained off and filtered. A yield of 845 grams of reaction product was obtained.GC analysis revealed the following composition: 89.0% tridecane, 2.1% tetradecane, 4.1% 1-tetradecanol, 4.2% dimeric reaction products.The reaction product was then fractionated by distillation to pure tridecane and deodorized with nitrogen. A colorless, thinly liquid and substantially odorless product was obtained. |
With hydrogen In n-heptane at 199.84℃; Autoclave; |
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 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 |
---|---|---|
With hydrogen at 325℃; for 5h; | 14 Example 14The process of Example 13 was repeated using the same equipment, pressure, temperature, and catalyst (5 g), except refined coconut oil, (50 g, obtained from Spectrum Chemicals of Gardena, Calif.) was used. The reaction products were analyzed by GC-FID to obtain the following linear paraffin (hydrocarbon) distribution by weight: C18=9%, C17=1%, C16=9%, C15=1%, C14=17.5, C13=2, C12=43.5%, C11=4, C10=5.5, C9=0.5, C8=6.5%, C7=0.5%. The C18:C17 ratio is approximately 9, C16:C15 ratio is 9, C14:C13 ratio is approximately 9, C12:C11 ratio is approximately 11, C10:C9 ratio is 11, and C8:C7 ratio is 13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
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 |
---|---|---|
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 |
---|---|---|
With hydrogen;palladium 10% on activated carbon; In Tridecane; at 40℃; for 3h; | Hydrogenation of the Normal Alpha Olefin and Olefin Reactor Effluent; A sample of the 1-tetradecene/1-hexadecene/1-octadecene olefin feedstock or isomerization reactor effluent (approximately 1 mL) was dissolved in n-tridecane (approximately 10 g). This mixture was then added to of a 10 weight percent palladium on carbon hydrogenation catalyst (approximately 0.1 gram) and contacted with a stream of hydrogen gas at atmospheric pressure and 40 C. for 3 hours. The hydrogenated olefin feedstock or isomerization reactor effluent was then separated from hydrogenation catalyst by filtration. A sample of the filtrate was than analyzed using the following GC analysis procedure. Persons having ordinary skill in the art would recognize that the tridecane solvent may be substituted with another appropriate solvent if it would interfere with the GC analysis of the hydrogenated olefin feedstock or isomerization reactor effluent for other olefin feedstocks and isomerization reactor effluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuryl dichloride | ||
With pyridine; sulfuryl dichloride Photolysis; | ||
With pyridine; sulfuryl dichloride at 25 - 35℃; Inert atmosphere; Irradiation; | Synthesis of n-Alkanesulfonyl Chlorides General procedure: The n-alkanesulfonyl chlorides (RSO2Cl) which are consideredas raw material, were obtained by photosulfochlorination.Thus, 0.172 mol of sulfuryl chloride (Fluka,97 % pure), freshly distilled under a stream of nitrogen until colorless, was added drop by drop to 0.345 mol of nalkane(n-dodecane, n-tetradecane, n-hexadecane, or noctadecane)(Fluka, 99 % pure) in the presence of pyridine(Fluka, 99.8 % pure) as catalyst (10-2 M) under visiblelight irradiation (150 W). The reaction temperature wasmaintained between 25 and 35 C. The reaction mixturewas bubbled with nitrogen before the addition of SO2Cl2and at the end of the reaction. The obtained n-alkanesulfonylchlorides, a mixture of primary and secondary isomers,were separated from the reaction mixture by solventextraction using acetonitrile (Fluka, 97 % pure), which wasthen evaporated leading to a yellow liquid. They were thenpurified on a silica gel column. The resulting n-alkanesulfonylchlorides (n-dodecane, n-tetradecane, n-hexadecane,and n-octadecane) were analyzed by FTIR and GC/MS/IE after their derivatization into the more thermallystable N,N-diethyl n-alkanesulfonamides. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99 %Chromat. | With [((Me)NN2)NiCl]; diphenylsilane; sodium isopropylate In toluene for 6.5h; Inert atmosphere; | |
79 %Chromat. | With tributyl-amine; cyclohexa-1,4-diene; 4-(3,6-dimethoxycarbazol-9-yl)-3-(trifluoromethyl)benzoic acid In N,N-dimethyl-formamide at 26℃; for 4h; Inert atmosphere; Schlenk technique; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 9 %Chromat. 2: 36 %Chromat. | With C12H36Cl2O4RuS4; hydrogen In benzene at 200℃; for 96h; |
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 200℃; 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 tris(pentafluorophenyl)borate In cyclohexane at 20℃; for 6h; Schlenk technique; Inert atmosphere; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tris(pentafluorophenyl)borate In cyclohexane at 20℃; for 6h; Schlenk technique; Inert atmosphere; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen at 550℃; Inert atmosphere; | Light-off tests General procedure: The preliminary study on the impact of Pt loading was performed in the saturator reactor described in ref. [28]. All the other experiments were carried out in a soot oxidation reactor. Two grams of 0.55 wt%Pt/Al2O3 catalyst (50 m) were physically mixed with 0.133 mmol of hydrocarbon. This ratio corresponds, for instance, to 40 mg coronene in 2g of catalyst. Temperature-programmed oxidation of 100 mg of this HC/catalyst mixture (6.65 mol HC) was carried out from ambient temperature to 550 C at 5 C min-1 in a 1%O2/He mixture (gas owrate:20 cm3 min-1). Oxygen concentration was continuously recorded by catharometry (after trapping of CO2, H2O and not reacted HCon Zeolite 13X and KOH), which allows to calculate the integrated amount of O2 consumed between 20 C and TC and the HC con-version at temperature T. It is assumed that the oxidation reaction produces only CO2 and water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triethylaluminum; 1,1-dibromomethane In hexane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 37% 2: 31% 3: 21% | With dibromobis(cyclopentadienyl)titanium(IV); triethylaluminum In hexane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
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With 1-hydroxy-pyrrolidine-2,5-dione; oxygen; manganese (II) acetate tetrahydrate; ozone at 80℃; for 7h; | 1; 3-12 Example 1 A 200-mL four-necked flask was equipped with a thermometer, a gas inlet tube, and a cooling condenser and was charged with tetradecane (supplied by Tokyo Chemical Industry Co., Ltd., 79.36 g, i.e., 104 mL, 400 mmol), N-hydroxysuccinimide (hereinafter also referred to as “NHSI”, supplied by Wako Pure Chemical Industries, Ltd., SP: 33.5 (MPa)1/2, 4 mmol), cobalt acetylacetonate (supplied by Tokyo Chemical Industry Co., Ltd., 0.4 mmol), and manganese acetate tetrahydrate (supplied by Wako Pure Chemical Industries, Ltd., 0.04 mmol). (0138) A gas used was oxygen containing 1.4 percent by volume of ozone gas. The ozone gas was generated using an ozone generator (trade name SG-01-PSA2, supplied by Sumitomo Precision Products Co., Ltd.). The gas was bubbled at a rate of 2 L/min. to fill the reactor with the gas, and the bubbling was then stopped. The temperature was raised up to 80° C., followed by heating with stirring for 7 hours with intermittent flow of the gas in a gas phase. (0139) The conversion from tetradecane, and the yields of oxides (tetradecanone and tetradecanol) were measured by gas chromatography immediately after the temperature reached 80° C. (zero hour), and 1 hour, 3 hours, and 7 hours thereafter. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridine; manganese; trifluoroacetic acid; sodium iodide; cobalt(II) bromide In acetonitrile at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
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91 %Chromat. | at 170℃; for 2h; Inert atmosphere; Schlenk technique; Sealed tube; | 3 General procedure for thermolysis General procedure: Thermolysis reactions were carried out in dry, sealed and evacuated vertical Schlenk tubes of 1-cm o.d. and 10-cm lengths. The platinum complexes were dissolved in DCM and transferred into the tube; the solvent was removed under vacuum and dried at least for 6h before thermolysis. The samples were then immersed in a thermostated oil bath constant at 170±5°C. The tubes were removed at intervals (2h) and quenched by immersion in liquid nitrogen. Decomposition products were extracted by 0.5mL pentane containing 20μL of chlorobenzene as internal standard and analyzed by GC/GCMS. Products were identified by comparison of retention times to those of authentic samples. Product yields were determined by response relative to the internal standard (chlorobenzene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A Schlenk tube was charged with2 (0.0793 g, 0.271 mmol) and toluene (1.0 mL). A solution of HG2 (0.0085 g, 0.0136mmol, 0.05eq) intoluene (1.0 mL) was added. The mixture was stirred for 2 hours at 100C, and then Pd/C (0.008 g) in ethanol (2 mL) was added. A balloon filled with hydrogen was connected to the Schlenk tube. The mixture was stirred overnight at room temperature. Then the brownish suspension was filtered, the filtrate was analyzed by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84 %Chromat. | With sodium tetrahydroborate; di-tert-butyl peroxide; diphenyldisulfane In <i>tert</i>-butyl alcohol at 120℃; for 48h; Inert atmosphere; Sealed tube; |
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 |
---|---|---|
66% | With cyclohexa-1,4-diene; 9-ethyl-N3,N3,N6,N6,-tetramethyl-9H-carbazole-3,6-diamine; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 23℃; for 48h; Inert atmosphere; UV-irradiation; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 86.7 %Chromat. 2: 4.8 %Chromat. | With hydrogen In decane at 320℃; for 8h; Autoclave; chemoselective reaction; | |
1: 62.8%Chromat. 2: 32.3 %Chromat. | With hydrogen In decane at 280℃; for 8h; Autoclave; | 2.4. Experimental procedure 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 μm 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 |
---|---|---|
1: 67.3 %Chromat. 2: 28.2 %Chromat. | With hydrogen In decane at 280℃; for 8h; Autoclave; | 2.4. Experimental procedure 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 μm 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 |
---|---|---|
90% | With hydrogen at 200℃; for 24h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; tetrabutylammonium p-toluenesulfonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; | 12. Ni-catalyzed C(sp2)-C(sp3) cross-coupling (Figure 2B) General procedure: General procedure HIn an argon-filled glovebox, a flame-dried 10 mL sealing tube equipped with a Teflon septumand magnetic stir bar was charged with ZrCp2HCl (258 mg, 1.0 mmol, 2.0 equiv.), the reactionvial was sealed tightly and removed from the glovebox, anhydrous THF (2.5 mL), alkene (1.1mmol, 2.2 equiv.) was added by a syringe under an argon atmosphere. The mixture was stirredfor 30 min until a clear yellow solution was obtained.In an argon-filled glovebox, another flame-dried 10 mL sealing tube equipped with a Teflonseptum and magnetic stir bar was charged with aryl iodide (0.5 mmol, 1.0 equiv.), Ni(dtbbpy)Br2(2.5 mg, 0.005 mmol, 1 mol%), tetrabutylammonium 4-toluenesulfonate (207 mg, 0.5 mmol, 1.0equiv.), the reaction vial was sealed tightly and removed from the glovebox, the previous clearalkyl zirconium reagent was transferred via syringe over 1 min to this reaction vial under anargon atmosphere. The reaction mixture was then stirred and irradiated with blue LEDs with afan placed above for cooling. After 24 h, the reaction mixture was diluted with CH2Cl2, filteredthrough a short pat of silica gel, and concentrated in vacuum. Purification of the crude productby flash chromatography on silica gel afforded the desired product.Hexylbenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With di-tert-butyl peroxide; (1,3-dimethylimidazol-2-ylidene)borane In <i>tert</i>-butyl alcohol at 120℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: tetradecane With glucose dehydrogenase from Bacillus megaterium; cytochrome P450 monooxygenase CYP505E3 from Aspergillus terreus; nicotinamide adenine dinucleotide In aq. phosphate buffer at 25℃; for 24h; Enzymatic reaction; Stage #2: chloro-trimethyl-silane With pyridine; N,O-Bis(trimethylsilyl)trifluoroacetamide at 70℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With platinum on activated charcoal; C24H16N2O4 In ethanol at 50℃; for 18h; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With whole cells of Escherichia coli overexpressed short-length Chlorella variabillis photodecarboxylase In dimethyl sulfoxide at 30℃; for 6h; Sealed tube; Irradiation; Microbiological reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: 5,5'-(hexane-1,1-diyl)bis(2-butylfuran) With palladium 10% on activated carbon; hydrogen; MIL-101-SO<SUB>3</SUB>H at 120℃; for 3h; Autoclave; High pressure; Stage #2: at 200℃; for 10h; Autoclave; |
Tags: 629-59-4 synthesis path| 629-59-4 SDS| 629-59-4 COA| 629-59-4 purity| 629-59-4 application| 629-59-4 NMR| 629-59-4 COA| 629-59-4 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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