GB616190A - Improvements in application of low temperature inter-esterification or alcoholysis to glycerides - Google Patents

Improvements in application of low temperature inter-esterification or alcoholysis to glycerides

Info

Publication number
GB616190A
GB616190A GB24055/46A GB2405546A GB616190A GB 616190 A GB616190 A GB 616190A GB 24055/46 A GB24055/46 A GB 24055/46A GB 2405546 A GB2405546 A GB 2405546A GB 616190 A GB616190 A GB 616190A
Authority
GB
United Kingdom
Prior art keywords
oils
acid
mono
oil
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
GB24055/46A
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble 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 Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of GB616190A publication Critical patent/GB616190A/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
    • C11C3/10Ester interchange
    • 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
    • C11C3/06Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol

Abstract

Fats and fatty oils are converted into mono- and diglycerides by alcoholysis and interesterification in the presence of an interesterification catalyst such as sodium methoxide and an organic hydroxy compound having at least one unesterified alcoholic hydroxyl group not acid enough to inactivate the catalyst, the conversion being carried out at a temperature sufficiently below 180 DEG F. to permit crystallisation of solid mono- and diglycerides as they are formed. The reaction may be conducted in the presence of an inert solvent. After separation of the solid and liquid fractions, the products may be used as such or they may be esterified with fatty or non-fatty mono- or polycarboxylic acids, or they may be split to form fatty acids and glycerol which may be reused in the alcoholysis reaction. The fatty acids may be used in soap making, while the liquid fractions may be used for preparing drying oils by esterifying the unesterified hydroxyl groups in such oils with the fatty acids of drying oils. Among fats and oils specified are palm, cotton seed, linseed, soybean, corn, rapeseed, menhaden, sardine, salmon, and pilchard oils, and tallow. Alcoholic substances referred to include glycerol, methanol, ethanol, propanol, isopropanol, butanols, amyl alcohol, acetone glycerol, allyl alcohol, glycidol, ethylene glycol, polyethylene glycol, di- and polyglycerol, penta-erythritol, sorbitol, mannitol, cyclohexanol, glycol monoethers, glycerol ethers, monoacetin, monobutyrin, lauryl alcohol, cetyl alcohol, benzyl alcohol, ethanolamine, and non-acid alcohol esters and salts of hydroxy carboxylic acids such as diethyl tartrate, potassium tartrate, ethyl lactate, and sodium glycollate. In addition to sodium methoxide, any alkali metal alkoxide from materials less acidic than phenol may be employed as catalysts including ethoxides, propoxides, butoxides, and alkoxides of lauryl alcohol, ethylene glycol, and mono- and diglycerides of the glyceride mixture; also tetramethyl ammonium methoxide, lauryl benzyl ammonium methoxide, and alkali metal organic compounds such as triphenylmethyl sodium, potassium pyrrole, and finely divided metallic suspensions of potassium or sodium in xylene. The catalyst may be added as a dispersion in xylene, toluene or petroleum naphtha. The amount of catalyst to be employed ranges from about 0.05 to 0.5 per cent in the case of sodium methoxide, while the amount of alcoholic body added may vary from about 1 per cent of the oil to amounts over and above those theoretically necessary to convert all the glycerides to fatty acid monoglycerides. At temperatures of 120 DEG F. to 80 DEG F. the greater proportion of the reaction takes place within 24 hours, but at lower temperatures a longer time such as 3 or 4 days may be necessary. If maximum conversion is desired, an even longer time such as 17 days may be occupied and the temperature may be reduced progressively for example from 90 DEG F. to 50 DEG F. as the mono- and diglycerides crystallise out. After the desired interesterification has taken place and before the temperature of the mixture is allowed to rise appreciably, the catalytic material is rendered inactive for example by the addition of hydrochloric acid, phosphoric acid, carbonic acid, glacial acetic acid, or water. In an example, glycerol containing a small amount of sodium hydroxide is added slowly to palm oil at 170 DEG C. with vigorous agitation. The product is cooled to 100 DEG C. and phosphoric acid added to neutralise the alkali. About 0.2 per cent sodium methoxide is then added with vigorous agitation and the mixture kept at 100 DEG F. in an atmosphere of nitrogen for 1 to 3 days. It is finally treated with phosphoric acid to inactivate the catalyst and filtered to give a solid fraction consisting of substantially completely saturated mono-, di- and triglycerides of palm oil fatty acids, and a liquid fraction containing the bulk of the unsaturated constituents. Other examples refer to the treatment of palm oil with methanol and of cottonseed oil with glycerol. The process can be applied to the separation of tallow and similar fats into commercial stearic acid and red oil (principally oleic acid). The mono- and diglycerides from cottonseed oil or soybean oil may be separated from the liquid constituents and the fractions converted into low and high titer soap respectively. Drying oils for paint may also be produced from the liquid fractions prepared according to the invention from linseed oil, semi-drying oils, or fish oils by esterifying unesterified hydroxyl groups in such fractions with fatty acids of drying oils. Specification 574,807 is referred to.ALSO:Fats and fatty oils are converted into mono-and diglycerides by alcoholysis and interesterification in the presence of an interesterification catalyst such as sodium methoxide and an organic hydroxy compound having at least one unesterified alcoholic hydroxyl group not acid enough to inactivate the catalyst, the conversion being carried out at a temperature sufficiently below 180 DEG F. to permit crystallisation of solid mono- and diglycerides as they are formed. The reaction may be conducted in the presence of an inert solvent. After separation of the solid and liquid fractions, the products may be used as such, or they may be esterified with fatty or non-fatty mono- or polycarboxylic acids, or they may be split to form fatty acids and glycerol which may be re-used in the alcoholysis reaction. The fatty acids may be used in soap making, while the liquid fractions may be used for preparing drying oils by esterifying the unesterified hydroxyl groups in such oils with the fatty acids of drying oils. Among fats and oils specified are palm, cotton seed, linseed, soybean, corn, rapeseed, menhaden, sardine, salmon, and pilchard oils, and tallow. Alcoholic substances referred to include glycerol, methanol, ethanol, propanol, isopropanol, butanols, amyl alcohol, acetone glycerol, allyl alcohol, glycidol, ethylene glycol, polyethylene glycol, di- and polyglycerol, penta-erythritol, sorbitol, mannitol, cyclohexanol, glycol monoethers, glycerol ethers, monoacetin, monobutyrin, lauryl alcohol, cetyl alcohol, benzyl alcohol, ethanolamine, and non-acid alcohol esters and salts of hydroxy carboxylic acids such as diethyl tartrate, potassium tartrate, ethyl lactate, and sodium glycollate. In addition to sodium methoxide, any alkali metal alkoxide from materials less acidic than phenol may be employed as catalysts including ethoxides, propoxides, butoxides, and alkoxides of lauryl alcohol, ethylene glycol, and mono- and p diglycerides of the glyceride mixture; also tetramethyl ammonium methoxide, lauryl benzyl ammonium methoxide, and alkali metal organic compounds such as triphenylmethyl sodium, potassium pyrrole, and finely-divided metallic suspensions of potassium or sodium in xylene. The catalyst may be added as a dispersion in xylene, toluene or petroleum naphtha. The amount of catalyst to be employed ranges from about 0.05 to 0.5 per cent in the case of sodium methoxide, while the amount of alcoholic body added may vary from about 1 per cent of the oil to amounts over and above those theoretically necessary to convert all the glycerides to fatty acid monoglycerides. At temperatures of 120 DEG F. to 80 DEG F. the greater proportion of the reaction takes place within 24 hours, but at lower temperatures a longer time such as 3 or 4 days may be necessary. If maximum conversion is desired, an even longer time such as 17 days may be occupied and the temperature may be reduced progressively, for example from 90 DEG F. to 50 DEG F. as the mono- and diglycerides crystallise out. After the desired interesterification has taken place and before the temperature of the mixture is allowed to rise appreciably, the catalytic material is rendered inactive for example by the addition of hydrochloric acid, phosphoric acid, carbonic acid, glacial acetic acid, or water. In an example, glycerol containing a small amount of sodium hydroxide is added slowly to palm oil at 170 DEG C. with vigorous agitation. The product is cooled to 100 DEG C. and phosphoric acid added to neutralise the alkali. About 0.2 per cent sodium methoxide is then added with vigorous agitation and the mixture kept at 100 DEG F. in an atmosphere of nitrogen for 1 to 3 days. It is finally treated with phosphoric acid to inactivate the catalyst and filtered to give a solid fraction consisting of substantially completely saturated monodi- and triglycerides of palm oil fatty acids, and a liquid fraction containing the bulk of the unsaturated constituents. Other examples refer to the treatment of palm oil with methanol and of cottonseed oil with glycerol. The process can be applied to the separation of tallow and similar fats into commercial stearic acid and red oil (principally oleic acid). The mono- and diglycerides from cottonseed oil or soybean oil may be separated from the liquid constituents and the fractions converted into low and high titer soap respectively. Drying oils for paint may also be produced from the liquid fractions prepared according to the invention from linseed oil, semi-drying oils, or fish oils by esterifying unesterified hydroxyl groups in such fractions with fatty acids of drying oils. Specification 574,807, [Group III], is referred to.
GB24055/46A 1945-11-06 1946-08-13 Improvements in application of low temperature inter-esterification or alcoholysis to glycerides Expired GB616190A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US616190XA 1945-11-06 1945-11-06

Publications (1)

Publication Number Publication Date
GB616190A true GB616190A (en) 1949-01-18

Family

ID=22036962

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24055/46A Expired GB616190A (en) 1945-11-06 1946-08-13 Improvements in application of low temperature inter-esterification or alcoholysis to glycerides

Country Status (1)

Country Link
GB (1) GB616190A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2683225A1 (en) * 1991-10-31 1993-05-07 Gattefosse Ets Sa PROCESS FOR IMPROVING A GLYCEROLYZED OIL.
US6258808B1 (en) 1991-06-27 2001-07-10 Novartis Ag Pharmaceutical composition
US6420355B2 (en) 1992-09-25 2002-07-16 Novartis Ag Pharmaceutical compositions containing cyclosporins
US6475519B1 (en) 1997-01-30 2002-11-05 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporin A
US6582718B2 (en) 1992-05-13 2003-06-24 Novartis Ag Cyclosporin compositions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6258808B1 (en) 1991-06-27 2001-07-10 Novartis Ag Pharmaceutical composition
US6844459B2 (en) 1991-06-27 2005-01-18 Novartis Ag Pharmaceutical Composition
FR2683225A1 (en) * 1991-10-31 1993-05-07 Gattefosse Ets Sa PROCESS FOR IMPROVING A GLYCEROLYZED OIL.
WO1993009211A1 (en) * 1991-10-31 1993-05-13 Gattefosse S.A. Method for improving a glycerolyzed oil
US5441738A (en) * 1991-10-31 1995-08-15 Gattefosse Sa Process for improving a glycerolysed oil
US6582718B2 (en) 1992-05-13 2003-06-24 Novartis Ag Cyclosporin compositions
US6262022B1 (en) 1992-06-25 2001-07-17 Novartis Ag Pharmaceutical compositions containing cyclosporin as the active agent
US6420355B2 (en) 1992-09-25 2002-07-16 Novartis Ag Pharmaceutical compositions containing cyclosporins
US6475519B1 (en) 1997-01-30 2002-11-05 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporin A
US6723339B2 (en) 1997-01-30 2004-04-20 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporin A

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