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Chemical Structure| 1589-47-5 Chemical Structure| 1589-47-5

Structure of 1589-47-5

Chemical Structure| 1589-47-5

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Product Citations

Product Citations

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.

Keywords: 2-methoxypropan-1-ol ; analytical method ; air at workplaces ; gas chromatographic method with mass spectrometry ; health sciences ; environmental engineering

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Product Details of [ 1589-47-5 ]

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

Safety of [ 1589-47-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 1589-47-5 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

29.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.46
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.17
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.01
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.18
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.22

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.16
Solubility 62.4 mg/ml ; 0.692 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.01
Solubility 91.5 mg/ml ; 1.02 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.18
Solubility 60.1 mg/ml ; 0.667 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.97 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.36

Application In Synthesis of [ 1589-47-5 ]

* 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.

  • Upstream synthesis route of [ 1589-47-5 ]

[ 1589-47-5 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 187737-37-7 ]
  • [ 57-55-6 ]
  • [ 107-98-2 ]
  • [ 1589-47-5 ]
  • [ 75-56-9 ]
References: [1] Patent: EP1258483, 2002, A1, . Location in patent: Example 1-2.
[2] Patent: EP1258483, 2002, A1, . Location in patent: Page 5.
[3] Patent: EP1247805, 2002, A1, . Location in patent: Example 1-2.
[4] Patent: US6372924, 2002, B1, . Location in patent: Example 1.
[5] Patent: US6372924, 2002, B1, . Location in patent: Example 20.
[6] Patent: US6372924, 2002, B1, . Location in patent: Example 16-19.
  • 2
  • [ 67-56-1 ]
  • [ 124-38-9 ]
  • [ 75-56-9 ]
  • [ 108-32-7 ]
  • [ 107-98-2 ]
  • [ 1589-47-5 ]
YieldReaction ConditionsOperation 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.
References: [1] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
[2] Journal of Chemical Research, 2011, vol. 35, # 11, p. 654 - 656,3.
  • 3
  • [ 67-56-1 ]
  • [ 124-38-9 ]
  • [ 75-56-9 ]
  • [ 108-32-7 ]
  • [ 57-55-6 ]
  • [ 107-98-2 ]
  • [ 1589-47-5 ]
  • [ 616-38-6 ]
YieldReaction ConditionsOperation 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.

References: [1] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
[2] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
[3] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
[4] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
[5] Journal of Chemical Research, 2011, vol. 35, # 11, p. 654 - 656,3.
[6] Journal of Chemical Research, 2011, vol. 35, # 11, p. 654 - 656,3.
[7] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
[8] Frontiers of Chemistry in China, 2011, vol. 6, # 1, p. 21 - 30.
  • 4
  • [ 17639-76-8 ]
  • [ 1589-47-5 ]
References: [1] Canadian Journal of Chemistry, 1964, vol. 42, p. 990 - 1004.
[2] Patent: US2011/86882, 2011, A1, . Location in patent: Page/Page column 22; 23.
  • 5
  • [ 187737-37-7 ]
  • [ 75-56-9 ]
  • [ 57-55-6 ]
  • [ 107-98-2 ]
  • [ 74-98-6 ]
  • [ 1589-47-5 ]
  • [ 67-63-0 ]
  • [ 79-10-7 ]
  • [ 107-02-8 ]
References: [1] Catalysis Today, 2014, vol. 227, p. 87 - 95.
  • 6
  • [ 67-56-1 ]
  • [ 124-38-9 ]
  • [ 75-56-9 ]
  • [ 108-32-7 ]
  • [ 57-55-6 ]
  • [ 107-98-2 ]
  • [ 1589-47-5 ]
YieldReaction ConditionsOperation 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.
References: [1] Journal of Organometallic Chemistry, 2015, vol. 794, p. 231 - 236.
  • 7
  • [ 57-55-6 ]
  • [ 616-38-6 ]
  • [ 107-98-2 ]
  • [ 1589-47-5 ]
  • [ 7778-85-0 ]
References: [1] Patent: WO2016/99789, 2016, A1, . Location in patent: Paragraph 0057; 0058; 0059; 0060.
  • 8
  • [ 67-56-1 ]
  • [ 75-56-9 ]
  • [ 107-98-2 ]
  • [ 1589-47-5 ]
References: [1] Synthetic Communications, 2011, vol. 41, # 6, p. 891 - 897.
[2] Polish Journal of Chemistry, 1986, vol. 60, # 4-6, p. 593 - 598.
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 680.
[4] Zhurnal Obshchei Khimii, 1944, vol. 14, p. 1039,1041[5] Chem.Abstr., 1946, p. 7153.
[6] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 123.
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[8] Zhurnal Obshchei Khimii, 1944, vol. 14, p. 1039,1041[9] Chem.Abstr., 1946, p. 7153.
[10] Bulletin des Societes Chimiques Belges, 1930, vol. 39, p. 399.
[11] Journal of the American Chemical Society, 1950, vol. 72, p. 1251.
[12] Synthesis, 1981, # 4, p. 280 - 282.
[13] Journal of Organic Chemistry, 1988, vol. 53, # 10, p. 2300 - 2303.
[14] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993, # 2, p. 199 - 203.
[15] Journal of the American Chemical Society, 1955, vol. 77, p. 2420,2423.
[16] Journal of the American Chemical Society, 1955, vol. 77, p. 2420,2423.
[17] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2927 - 2929.
[18] Journal of Catalysis, 2008, vol. 258, # 1, p. 14 - 24.
[19] Patent: US2009/187049, 2009, A1, . Location in patent: Page/Page column 3.
[20] Patent: US2009/187049, 2009, A1, . Location in patent: Page/Page column 3.
[21] Patent: WO2009/134630, 2009, A1, . Location in patent: Page/Page column 8-9, 14.
[22] Applied Catalysis A: General, 2010, vol. 377, # 1-2, p. 107 - 113.
[23] New Journal of Chemistry, 2010, vol. 34, # 11, p. 2534 - 2536.
[24] Kinetics and Catalysis, 2011, vol. 52, # 3, p. 386 - 390.
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YieldReaction ConditionsOperation 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).
References: [1] Patent: EP1359148, 2003, A1, . Location in patent: Page/Page column 6-7.
[2] Patent: US7470801, 2008, B1, . Location in patent: Page/Page column 7.
[3] Patent: US7470801, 2008, B1, . Location in patent: Page/Page column 7.
[4] Patent: US7470801, 2008, B1, . Location in patent: Page/Page column 7.
[5] Applied Catalysis A: General, 2016, vol. 523, p. 73 - 84.
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YieldReaction ConditionsOperation 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).
References: [1] Applied Catalysis A: General, 2016, vol. 523, p. 73 - 84.
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