GB587533A - Improvements in or relating to alcoholysis of fatty glycerides - Google Patents

Improvements in or relating to alcoholysis of fatty glycerides

Info

Publication number
GB587533A
GB587533A GB3828/44A GB382844A GB587533A GB 587533 A GB587533 A GB 587533A GB 3828/44 A GB3828/44 A GB 3828/44A GB 382844 A GB382844 A GB 382844A GB 587533 A GB587533 A GB 587533A
Authority
GB
United Kingdom
Prior art keywords
alcoholysis
acid
alcohol
employed
glycerine
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
GB3828/44A
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.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive 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 Colgate Palmolive Co filed Critical Colgate Palmolive Co
Publication of GB587533A publication Critical patent/GB587533A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils

Landscapes

  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

Glycerine and alkyl esters of fatty acids are prepared by heating a fatty glyceride with an aliphatic monohydric alcohol having one to six carbon atoms per molecule in the presence of an alcoholysis catalyst at a temperature above the normal boiling point of the monohydric alcohol and at a pressure sufficient to maintain a liquid monohydric alcohol phase. Suitable fatty glycerides are coconut, palm, olive, cottonseed, corn, tung, whale or fish oils and tallow, while suitable monohydric alcohols are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, tertiary butyl and the amyl alcohols. Alcoholysis catalysts which may be employed are sodium hydroxide, sodium methylate, sodium carbonate, barium oxide, lime, tetramethyl ammonium hydroxide, boron trifluoride, aluminium chloride, hydrochloric acid, trichloracetic acid, phosphoric acid, glycerine mono-acid sulphate, sulphuric acid, organic sulphonic acids and alkyl sulphuric acids. The glyceride employed may be refined but the presence of water or free fatty acid may be tolerated. The alcoholysis process, which may be a batch or a continuous process, may be brought to the degree of completion desired in a single contacting of the reaction materials or, alternatively, the multi-stage process of Specification 587,523 may be employed. If desired, the pressure employed during the alcoholysis may be low enough to permit the volatilization of a portion of the monohydric p alcohol. Following the alcoholysis, any soap formed through the presence of an alkaline alcoholysis catalyst may be decomposed with acid and any unreacted monohydric alcohol may be distilled off. Glycerine and alkyl esters may be recovered by distillation or by allowing the mixture to settle, the glycerine separating as a lower layer. In examples, (a) coconut oil is reacted with ethyl alcohol in presence of caustic soda or sulphuric acid, (b) coconut oil or tallow is reacted with methyl alcohol in presence of sulphuric acid and (c) cottonseed oil or a mixture of coconut oil and tallow is reacted with methyl alcohol in presence of caustic soda. The Specification as open to inspection under Sect. 91 describes the alcoholysis of fatty acid esters of higher alcohols, such as woolfat, and states that aryl-substituted aliphatic alcohols such as benzyl alcohol may be employed. This subject-matter does not appear in the Specification as accepted.ALSO:Glycerine and alkyl esters of fatty acids are prepared by heating a fatty glyceride with an aliphatic monohydric alcohol having 1 to 6 carbon atoms per molecule in the presence of an alcoholysis catalyst at a temperature above the normal boiling point of the monohydric alcohol and at a pressure sufficient to maintain a liquid monohydric alcohol phase. Suitable fatty glycerides are coconut, palm, olive, cottonseed, corn, tung, whale or fish oils and tallow, while suitable monohydric alcohols are methyl, ethyl, propyl, isopropyl, the butyl and the amyl alcohols. Alcoholysis catalysts which may be employed are sodium hydroxide, carbonate or methylate, barium oxide, lime, tetramethyl ammonium hydroxide, boron trifluoride, aluminium chloride, hydrochloric acid, trichloroacetic acid, phosphoric acid, glycerine mono-acid sulphate, sulphuric acid, organic sulphonic acids and alkyl sulphuric acids. The glyceride employed may be refined but the presence of water or free fatty acid may be tolerated. The alcoholysis process, which may be a batch or a continuous process, may be brought to the degree of completion desired in a single contacting of the reaction materials or, alternatively, the multi-stage process of Specification 587,523 may be employed. If desired, the pressure employed during the alcoholysis may be low enough to permit the volatilisation of a portion of the monohydric alcohol. Following the alcoholysis, any soap formed through the presence of an alkaline alcoholysis catalyst may be decomposed with acid and any unreacted monohydric alcohol may be distilled off. Glycerine and alkyl esters may be recovered by distillation or by allowing the mixture to settle, the glycerine separating as a lower layer. In examples: (a) coconut oil is reacted with ethyl alcohol in presence of caustic soda or sulphuric acid; (b) coconut oil or tallow is reacted with methyl alcohol in presence of sulphuric acid and (c) cottonseed oil or a mixture of coconut oil and tallow is reacted with methyl alcohol in presence of caustic soda. The Specification as open to inspection under Sect. 91 describes the alcoholysis of fatty acid esters of higher alcohols, such as wool fat and states that aryl-substituted aliphatic alcohols such as benzyl alcohol may be employed. This subject-matter does not appear in the Specification as accepted.
GB3828/44A 1943-03-30 1944-03-01 Improvements in or relating to alcoholysis of fatty glycerides Expired GB587533A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US587533XA 1943-03-30 1943-03-30

Publications (1)

Publication Number Publication Date
GB587533A true GB587533A (en) 1947-04-29

Family

ID=22018723

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3828/44A Expired GB587533A (en) 1943-03-30 1944-03-01 Improvements in or relating to alcoholysis of fatty glycerides

Country Status (1)

Country Link
GB (1) GB587533A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1044060B (en) * 1952-10-09 1958-11-20 Ici Ltd Process for the production of esters of higher molecular weight fatty acids in addition to glycerine by transesterification of triglycerides
GB2148897A (en) * 1983-11-03 1985-06-05 Inst Penyelidikan Minyak Kelap Catalytic esterification of carboxylic acid/glyceride mixtures
WO1992022631A1 (en) * 1991-06-11 1992-12-23 Beku Environmental Products Ltd. Degreaser composition comprising monounsaturated wax ester

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1044060B (en) * 1952-10-09 1958-11-20 Ici Ltd Process for the production of esters of higher molecular weight fatty acids in addition to glycerine by transesterification of triglycerides
GB2148897A (en) * 1983-11-03 1985-06-05 Inst Penyelidikan Minyak Kelap Catalytic esterification of carboxylic acid/glyceride mixtures
WO1992022631A1 (en) * 1991-06-11 1992-12-23 Beku Environmental Products Ltd. Degreaser composition comprising monounsaturated wax ester

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