GB655237A - Improvements in the preparation of glycol and glycerol and their esters - Google Patents

Improvements in the preparation of glycol and glycerol and their esters

Info

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
Application number
GB31895/48A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB655237A publication Critical patent/GB655237A/en
Expired legal-status Critical Current

Links

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

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.
GB31895/48A 1947-12-23 1948-12-09 Improvements in the preparation of glycol and glycerol and their esters Expired GB655237A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (3)

* Cited by examiner, † Cited by third party
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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