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Structure of 1589-47-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Smuga, Jakub ; Pisarska, Anna ; Kucharska, Małgorzata ; Wesołowski, Wiktor ;
Abstract: 2-Methoxypropan-1-ol (2M1P) is a colorless, flammable liquid with an irritating effect. It is a primary alcohol formed as a by-product in the production of propylene glycol monomethyl ether (1-methoxypropan-2-ol). Therefore, exposure to this substance is inextricably connected with exposure to 1-methoxypropan-2-ol which is used as a solvent for paints, varnishes, dyes, etc., and as a component of cleaning preparations and an intermediate for chemical synthesis. In working environment, workers may be exposed to the action of 2-methoxypropan-1-ol by inhalation and dermal route. The aim of this study was to develop and validate a method for determining 2-methoxypropan-1-ol in workplace air. The developed method of 2M1P determination consists in adsorption of vapors of this substance on coconut shell charcoal, extraction with a solution of methanol in carbon disulfide and chromatographic analysis of the obtained solution. The study was performed with gas chromatograph coupled with mass spectrometer (GC-MS), equipped with a polar ZB-WAXplus capillary column (length 60 m, diameter 0.25 mm and the film thickness of the stationary phase 0.5 µm). The developed method is linear in the concentration range of 10.0-400.0 µg/ml, which corresponds to the range of 1.0-40.0 mg/m3 for a 10-L air sample.The analytical method described in this paper makes it possible to determine 2-methoxypropan-1-ol in workplace air in the presence of comorbid substances. This method is precise, accurate and it meets the criteria for procedure for determining chemical agents listed in Standard No. PN-EN 482. The developed method of determination of 2-methoxypropan-1-ol in workplace air has been recorded as an analytical procedure (see Appendix). This article discusses the problems of occupational safety and health, which are covered by health sciences and environmental engineering.
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Keywords: 2-methoxypropan-1-ol ; analytical method ; air at workplaces ; gas chromatographic method with mass spectrometry ; health sciences ; environmental engineering
Show More >
CAS No. : | 1589-47-5 |
Formula : | C4H10O2 |
M.W : | 90.12 |
SMILES Code : | COC(C)CO |
MDL No. : | MFCD00126948 |
InChI Key : | YTTFFPATQICAQN-UHFFFAOYSA-N |
Pubchem ID : | 14846 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225 |
Precautionary Statements: | P210-P403+P235 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
Num. heavy atoms | 6 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 23.59 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.46 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.18 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.04 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.22 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.16 |
Solubility | 62.4 mg/ml ; 0.692 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.01 |
Solubility | 91.5 mg/ml ; 1.02 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.18 |
Solubility | 60.1 mg/ml ; 0.667 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.97 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.36 |
* 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 |
---|---|---|
54.8% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.2% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
12.5% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
5.8% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
23% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
7.8% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.4% | at 130℃; for 8 h; Autoclave; High pressure | General procedure: The one-step synthesis of DMC from carbon dioxide, epoxides and methanol was carried out in a sealed Teflon-lined stainless steel high pressure autoclave with inner volume of 50mL provided with a magnetic stirrer and an electric heater. Typical conditions and procedures are described as follows: a certain amount of methanol, propylene oxide (PO), catalyst and cocatalyst were added into the above autoclave. Alkali halides were used as catalysts, several typical crown ethers (i.e., [2,4],-dibenzo-18-crown-6 (DBC), 18-crown-6, 15-crown-5 and 12-crown-4) were used as cocatalysts, and polyethylene glycol (MW=4000, abbreviated as PEG4000) was used as comparison for the crown ether. Then CO2 (gas, > 99.99percent) was injected up to a certain pressure at room temperature. The autoclave was heated to a certain temperature and the mixture was stirred at that temperature for several hours. After the reaction, the autoclave was cooled to about 10°C with ice-water mixture and then depressurized. The liquid reaction mixture was analyzed by gas chromatograph (GC 2060) equipped with a capillary column (HP-INNOWAX, 30m×0.32mm×0.25μm) and flame ionization detector (FID) using n-butyl alcohol as an internal standard, and further identified by gas chromatography-mass spectrometry (Agilent 7890-5975C) by comparing retention times and fragmentation patterns with authentic samples. The temperature of the GC column was set at 60°C for 3min and then was programmed to rise to 80°C at the rate of 5°Cmin−1, and further reached 220°C at the rate of 30°Cmin−1 and remained at that temperature for 3min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.8 %Chromat. | at 60℃; for 12 h; Autoclave; Supercritical conditions | General procedure: PO synthesis reaction from propylene in presence of ex situ H2O2, as oxidizing agent, were performed in a 3 mL round bottom glass reactor in which the stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of TS-1 catalyst (2.5 mg), methanol (1.2 g), and propylene (9 mmol) were added, followed by the addition of the oxidant, 35percent wt H2O2 in water (0.4 mmol). Then, the mixture was heated at 60°C, and the reaction was monitored for 5 h. The experiments for the direct synthesis of PO with in situ generated H2O2 were carried out in a 15 mL stainless steel reactor which contained a relief valve, for safety. The stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of catalyst (15 mg), acidity inhibitor (ammonium acetate, 0.01 g) and co-solvent (0.2 gof different co-solvents) were added to the reactor, followed by the addition of propylene (2 mmol) and CO2, reaching carbon dioxide vapor pressure (>55 bar). Oxygen and hydrogen were added to the reactor by means of high pressure burettes, and then the reactor was heated up to desired temperature (ranging from room temperature to 80°C, according each experiment). The reaction experiments were carried out for 5 h, unless otherwise stated. At the end of the reaction, the reactor was cooled down and the pressure was slowly released by venting, accumulating the gaseous mixture in an inert gas sampling bag. 3-pentanone was used forrecovering any product that could be retained on the reactor walls. The amount of formed products, i.e., propylene oxide, acetone, propionaldehyde, acrolein, isopropanol, 1-methoxy-2-propanol (MP1), 2-methoxy-1-propanol (MP2), propylene glycol (PG) and propylene carbonate were analyzed using a Shimadzu Gas chro-matograph GC-2010 Plus provided with FID detector and 20 m length, 0.10 mm ID, 0.10 m df. Permabond FFAP column. The amounts of propane and unreacted propylene, oxygen and hydrogen were analyzed using a Bruker 450-GC which contains two different independent channels. The first one is provided with a thermal conductivity detector (TCD) and three different columns: Hayesep N (0.5 m length), Hayesep Q (1.5 m length) and molsieve 13× (1.2 m length), using argon as carrier. The second one is provided with two different flame ionization detectors (FID) and three different columns: capillary column CP-Wax (1 m length and 0.32 mm ID), CP-Porabond Q (25 m length and 0.32 mm ID) and CP-Wax (5 m length and 0.32 mm ID). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.6 %Chromat. | at 60℃; for 7 h; Autoclave; Supercritical conditions | General procedure: PO synthesis reaction from propylene in presence of ex situ H2O2, as oxidizing agent, were performed in a 3 mL round bottom glass reactor in which the stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of TS-1 catalyst (2.5 mg), methanol (1.2 g), and propylene (9 mmol) were added, followed by the addition of the oxidant, 35percent wt H2O2 in water (0.4 mmol). Then, the mixture was heated at 60°C, and the reaction was monitored for 5 h. The experiments for the direct synthesis of PO with in situ generated H2O2 were carried out in a 15 mL stainless steel reactor which contained a relief valve, for safety. The stirring was driven by a Teflon-coated magnetic stirrer. Known amounts of catalyst (15 mg), acidity inhibitor (ammonium acetate, 0.01 g) and co-solvent (0.2 gof different co-solvents) were added to the reactor, followed by the addition of propylene (2 mmol) and CO2, reaching carbon dioxide vapor pressure (>55 bar). Oxygen and hydrogen were added to the reactor by means of high pressure burettes, and then the reactor was heated up to desired temperature (ranging from room temperature to 80°C, according each experiment). The reaction experiments were carried out for 5 h, unless otherwise stated. At the end of the reaction, the reactor was cooled down and the pressure was slowly released by venting, accumulating the gaseous mixture in an inert gas sampling bag. 3-pentanone was used forrecovering any product that could be retained on the reactor walls. The amount of formed products, i.e., propylene oxide, acetone, propionaldehyde, acrolein, isopropanol, 1-methoxy-2-propanol (MP1), 2-methoxy-1-propanol (MP2), propylene glycol (PG) and propylene carbonate were analyzed using a Shimadzu Gas chro-matograph GC-2010 Plus provided with FID detector and 20 m length, 0.10 mm ID, 0.10 m df. Permabond FFAP column. The amounts of propane and unreacted propylene, oxygen and hydrogen were analyzed using a Bruker 450-GC which contains two different independent channels. The first one is provided with a thermal conductivity detector (TCD) and three different columns: Hayesep N (0.5 m length), Hayesep Q (1.5 m length) and molsieve 13× (1.2 m length), using argon as carrier. The second one is provided with two different flame ionization detectors (FID) and three different columns: capillary column CP-Wax (1 m length and 0.32 mm ID), CP-Porabond Q (25 m length and 0.32 mm ID) and CP-Wax (5 m length and 0.32 mm ID). |
A276375 [642-38-6]
(1R,2S,3S,4S,5R,6R)-6-Methoxycyclohexane-1,2,3,4,5-pentaol
Similarity: 0.63