GB655237A - Improvements in the preparation of glycol and glycerol and their esters - Google Patents
Improvements in the preparation of glycol and glycerol and their estersInfo
- Publication number
- GB655237A GB655237A GB31895/48A GB3189548A GB655237A GB 655237 A GB655237 A GB 655237A GB 31895/48 A GB31895/48 A GB 31895/48A GB 3189548 A GB3189548 A GB 3189548A GB 655237 A GB655237 A GB 655237A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- reaction
- atmos
- acetate
- glycerol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title abstract 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title abstract 9
- 150000002148 esters Chemical class 0.000 title abstract 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 235000011054 acetic acid Nutrition 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000004675 formic acid derivatives Chemical class 0.000 abstract 3
- 150000005846 sugar alcohols Polymers 0.000 abstract 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- 229940011182 cobalt acetate Drugs 0.000 abstract 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 glycol formates Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical class CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 abstract 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- CXQXWHWPDDUDPI-UHFFFAOYSA-N [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O Chemical compound [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O CXQXWHWPDDUDPI-UHFFFAOYSA-N 0.000 abstract 1
- WNVXPUKIBYOUIG-UHFFFAOYSA-N [Mn+2].[O-][Cr]([O-])=O Chemical compound [Mn+2].[O-][Cr]([O-])=O WNVXPUKIBYOUIG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 235000013773 glyceryl triacetate Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 229940046892 lead acetate Drugs 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229960002622 triacetin Drugs 0.000 abstract 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/159—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with reducing agents other than hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/1512—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions
- C07C29/1514—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by reaction conditions the solvents being characteristic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
- C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Glycol, glycerol, and their esters are prepared by heating carbon monoxide with hydrogen at above 150 DEG C. and above 1,500 atmos., preferably at 180-300 DEG C. and 2,000-5,000 atmos. Formate esters are generally formed in addition to the free polyhydric alcohols. In the presence of water, ethylene glycol and formates thereof are formed selectively. Acetic acid directs the reaction to the formation of glycerol and glyceryl acetates. Other esterifying reactants may be present to produce esters of the polyhydric alcohol. Reaction may be in vapour or liquid phase. Inert diluents such as hydrocarbons, alcohols, and esters, or reactive solvents such as formic, acetic, propionic, stearic, and benzoic acids, and phthalic, acetic, and benzoic anhydrides may be present. Polyhydric alcohol esters, e.g. glycol formates or acetates, may be used as reaction media. Hydrogenation catalysts, especially those forming carbonyls, may be present: Ni, Cu, Co, Cr, Mn, and Ru, as metals or their compounds, alone or on supports, are specified. Compounds of cobalt, especially those soluble in the reaction mixture, e.g. the acetate, naphthenate, carbonyl, carbonyl hydride or complexes, and inorganic salts are particularly suitable. Amounts may be about 0.001 to 20 per cent by weight of the reaction mixture. The ratio CO : H2 may be from 10 : 1 to 1 : 3, preferably 2 : 1 to 1 : 1. Mixtures of CO2 and H2 or of CO or CO2 and steam may be used, and metal carbonyls may supply the CO. Unreacted gas may be recycled, after separation of products, preferably with make-up reactants. Heat evolved may be absorbed by effecting a simultaneous endothermic reaction. In examples: (1) to (3) CO and H2 are heated at 3,000 atmos. in presence of acetic acid containing cobalt acetate yielding ethylene glycol diacetate and glycerol triacetate with lower boiling esters; (4) to (7) water containing cobalt acetate, manganese naphthenate, copper zinc chromite, tin acetate, lead acetate, zinc oxide, antimony trioxide, manganese chromite or chromium carbonyl is the reaction medium, pressures vary from 1,800 to 3,000 atmos., and the products are mainly ethylene glycol and its formates. Specification 625,909 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US655237XA | 1947-12-23 | 1947-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB655237A true GB655237A (en) | 1951-07-11 |
Family
ID=22063313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31895/48A Expired GB655237A (en) | 1947-12-23 | 1948-12-09 | Improvements in the preparation of glycol and glycerol and their esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB655237A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940432A (en) * | 1973-06-19 | 1976-02-24 | Union Carbide Corporation | Process for making ethylene glycol |
| EP0013008A1 (en) * | 1978-12-21 | 1980-07-09 | Union Carbide Corporation | Process for producing alcohols |
| US4362820A (en) * | 1981-06-29 | 1982-12-07 | Union Carbide Corporation | Process for producing ethylene glycol and methanol |
-
1948
- 1948-12-09 GB GB31895/48A patent/GB655237A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940432A (en) * | 1973-06-19 | 1976-02-24 | Union Carbide Corporation | Process for making ethylene glycol |
| EP0013008A1 (en) * | 1978-12-21 | 1980-07-09 | Union Carbide Corporation | Process for producing alcohols |
| US4362820A (en) * | 1981-06-29 | 1982-12-07 | Union Carbide Corporation | Process for producing ethylene glycol and methanol |
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