GB587532A - Improvements in or relating to alcoholysis of fatty glycerides - Google Patents

Improvements in or relating to alcoholysis of fatty glycerides

Info

Publication number
GB587532A
GB587532A GB2865/44A GB286544A GB587532A GB 587532 A GB587532 A GB 587532A GB 2865/44 A GB2865/44 A GB 2865/44A GB 286544 A GB286544 A GB 286544A GB 587532 A GB587532 A GB 587532A
Authority
GB
United Kingdom
Prior art keywords
alcohol
reaction mixture
reacted
glycerine
neutralised
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
GB2865/44A
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 GB587532A publication Critical patent/GB587532A/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

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  • 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)

Abstract

A fatty glyceride is reacted with a monohydric or polyhydric alcohol in the presence of an alcoholysis catalyst, then the influence of the catalyst is removed by the addition of a neutralizing agent, unreacted alcohol is removed and glycerine recovered from the reaction products. Suitable glycerides are coconut, palm, olive, cottonseed, soyabean, corn, tung, whale and fish oils and tallow, while alcoholysis catalysts mentioned are sodium hydroxide, sodium methylate, sodium carbonate, barium oxide, lime, tetramethyl ammonium hydroxide, hydrochloric, trichloracetic, phosphoric, sulphuric and organic sulphonic acids, aluminium chloride, boron fluoride, glycerine monoacid sulphate and alkyl sulphuric acids. The alcohol employed may be a saturated alphatic monohydric alcohol containing one to about six carbon atoms in the molecule or a polyhydric alcohol such as ethylene glycol, propylene glycol, trimethylene glycol, the amylene glycols, mannitol, sorbitol and erythritol. Where an alkaline alcoholysis catalyst is employed its influence may be removed by neutralizing or partially neutralizing with acetic, hydrochloric, sulphuric, phosphoric, boric, benzenesulphonic, or higher fatty acid or sulphur dioxide, while an acid catalyst may be neutralized or partially neutralized with caustic soda, soda ash, soap, sodium tetraborate or sodium acetate. Although a refined fatty glyceride may be employed in the alcoholysis, the presence in the glyceride of moisture or free fatty acid may be tolerated. The alcoholysis reaction may be carried to completion in one step or, as described in Specification 587,523, in more than one stage, or the reaction may be carried only so far as the production of fatty acid partial esters of a polyhydric alcohol. Various treatments for recovering glycerine and other reaction products from the reaction mixture are described. In examples, (a) coconut oil is reacted with methyl alcohol in presence of sodium hydroxide and the reaction mixture neutralized with an alcoholic solution of glacial acetic acid, (b) cottonseed oil is reacted with ethyl alcohol in presence of concentrated sulphuric acid and the reaction mixture is neutralized with sodium acetate, (c) tallow, which may contain moisture and free fatty acid, is reacted with methyl alcohol in presence of sodium hydroxide and the reaction mixture neutralized with stearic or glacial acetic acid, (d) coconut oil is reacted with methyl alcohol in presence of concentrated sulphuric acid and the reaction mixture is partially neutralized with an alcoholic solution of sodium hydroxide, neutralization being completed with an alcoholic solution of sodium coconut oil soap. Then, in each of these examples, unreacted alcohol is volatilised off, the residue is distilled and the distillate is allowed to settle into a lower layer of glycerine and an upper layer containing alkyl esters of fatty acids, the layers being then separated. In other examples, (e) sesame oil is reacted with methyl alcohol in presence of sodium hydroxide and the reaction mixture neutralized with dilute sulphuric acid; the neutralized mixture is allowed to settle into a lower layer of glycerine and an upper layer containing alkyl esters of fatty acids, and unreacted alcohol is distilled from the top layer; the residue is again allowed to settle into two layers, methyl esters are distilled from the top layer and the still residue is returned to the alcoholysis vessel for recycle, (f) coconut oil is reacted with ethyl alcohol in presence of sodium hydroxide and the reaction mixture neutralized with sulphur dioxide; the neutralized mixture is allowed to settle into a lower layer of glycerine and an upper layer containing alkyl esters of fatty acids, and the upper layer is distilled first to remove unreacted alcohol and then ethyl esters; the still residue is returned to the alcoholysis vessel for recycle, (g) cottonseed oil is reacted with propylene glycol in presence of concentrated sulphuric acid and the reaction mixture neutralized with sodium hydroxide; fatty acid mono-esters of propylene glycol are distilled from the neutralized mixture. Specifications 578,751, 587,524 and 587,533 also are referred to.ALSO:Esters of fatty acids are prepared by reacting a fatty glyceride with a monohydric or polyhydric alcohol in the presence of an alcoholysis catalyst, then removing the influence of the catalyst by the addition of a neutralising agent, removing unreacted alcohol and finally recovering the reaction products from the mixture. Suitable glycerides are coconut, palm, olive, cottonseed, soyabean, corn, tung, whale and fish oils and tallow, while alcoholysis catalysts mentioned are sodium hydroxide, sodium methylate, sodium carbonate, barium oxide, lime, tetramethyl ammonium hydroxide, hydrochloric, trichloracetic, phosphoric, sulphuric, alkyl sulphuric and organic sulphonic acids, aluminium chloride, boron fluoride and glycerine mono-acid sulphate. The alcohol employed may be a saturated aliphatic monohydric alcohol containing one to about six carbon atoms in the molecule or a polyhydric alcohol such as glycerine, ethylene glycol, propylene glycol, trimethylene glycol, the amylene glycols, mannitol, sorbitol and erythritol. Where an alkaline alcoholysis catalyst is employed its influence may be removed by neutralising or partially neutralising with acetic, hydrochloric, sulphuric, phosphoric, boric, benzenesulphonic or higher fatty acid or sulphur dioxide, while an acid catalyst may be neutralised or partially neutralised with caustic soda, soda ash, soap, sodium tetraborate or sodium acetate. Although a refined fatty glyceride may be employed in the alcoholysis, the presence in the glyceride of moisture or free fatty acid may be tolerated. The alcoholysis reaction may be carried to completion in one step or, as described in Specification 587,523, in more than one stage, or the reaction may be carried only so far as the production of fatty acid partial esters of a polyhydric alcohol. Various treatments for recovering the reaction products from the reaction mixture are described. In examples: (a) coconut oil is reacted with methyl alcohol in presence of sodium hydroxide and the reaction mixture neutralised with an alcoholic solution of glacial acetic acid; (b) cottonseed oil is reacted with ethyl alcohol in presence of concentrated sulphuric acid and the reaction mixture is neutralised with sodium acetate; (c) tallow, which may contain moisture and free fatty acid, is reacted with methyl alcohol in presence of sodium hydroxide and the reaction mixture neutralised with stearic or glacial acetic acid; (d) coconut oil is reacted with methyl alcohol in presence of concentrated sulphuric acid and the reaction mixture is partially neutralised with an alcoholic solution of sodium hydroxide, neutralisation being completed with an alcoholic solution of sodium coconut oil soap. Then in each of these examples, unreacted alcohol is volatilised off, the residue is distilled and the distillate is allowed to settle into a lower layer of glycerine and an upper layer containing alkyl esters of fatty acids, the layers being then separated. In other examples, sesame oil is reacted with methyl alcohol in presence of sodium hydroxide and the reaction mixture neutralised with dilute sulphuric acid; the neutralised mixture is allowed to settle into a lower layer of glycerine and an upper layer containing alkyl esters of fatty acids, and unreacted alcohol is distilled from the top layer; the residue is again allowed to settle into two layers, methyl esters are distilled from the top layer and the still residue is returned to the alcoholysis vessel for recycle; (f) coconut oil is reacted with ethyl alcohol in presence of sodium hydroxide and the reaction mixture neutralised with sulphur dioxide; the neutralised mixture is allowed to settle into a lower layer of glycerine and an upper layer containing alkyl esters of fatty acids, and the upper layer is distilled first to remove unreacted alcohol and then ethyl esters; the still residue is returned to the alcoholysis vessel for recycle; (g) cottonseed oil is reacted with propylene glycol in presence of concentrated sulphuric acid and the reaction mixture neutralised with sodium hydroxide; fatty acid mono-esters of propylene glycol are distilled from the neutralised mixture; (h) tallow is reacted with glycerine in presence of concentrated sulphuric acid and the reaction mixture is neutralised with a solution of sodium hydroxide in glycerine; glycerine is distilled off from the neutralised reaction mixture leaving monoglycerides of fatty acids; (i) tallow is reacted with glycerine in presence of sodium hydroxide and the reaction mixture is allowed to settle into two layers in order to remove part of the glycerine as a lower layer; the upper layer is neutralised with glacial acetic acid and extracted with ether; ether is volatilised from the extract and monoglycerides of fatty acids distilled from the residue. Specifications 578,751, 587,524 and 587,533 also are referred to. The Specification as open to inspection under Sect. 91 refers to the alcoholysis of fatty acid esters in which at least one of the alcohols concerned, i.e. the free or combined alcohol, is a polyhydric alcohol, and mentions benzyl alcohol as a free alcohol and wool fat as a fatty acid ester. In an example, methyl laurate is reacted with propylene glycol in presence of sodium hydroxide and the reaction mixture is neutralized with concentrated sulphuric acid. Lauric acid mono- and di-esters of propylene glycol are distilled from the neutralised reaction mixture. This subject-matter does not appear in the Specification as accepted.
GB2865/44A 1943-03-20 1944-02-16 Improvements in or relating to alcoholysis of fatty glycerides Expired GB587532A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US587532XA 1943-03-20 1943-03-20

Publications (1)

Publication Number Publication Date
GB587532A true GB587532A (en) 1947-04-29

Family

ID=22018721

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2865/44A Expired GB587532A (en) 1943-03-20 1944-02-16 Improvements in or relating to alcoholysis of fatty glycerides

Country Status (1)

Country Link
GB (1) GB587532A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654767A (en) * 1950-03-18 1953-10-06 Sherwin Williams Co Process of alcoholysis
WO2006107407A1 (en) * 2005-04-04 2006-10-12 Renewable Products Development Laboratories, Inc. Process and system for producing biodiesel or fatty acid esters from multiple trigi yceride feedstocks
EP1889899A1 (en) 2006-08-15 2008-02-20 NOVA Biosource Technologies, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
US7806945B2 (en) 2003-01-27 2010-10-05 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US7871448B2 (en) 2003-01-27 2011-01-18 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US9725397B2 (en) 2003-01-27 2017-08-08 REG Seneca, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
US9957464B2 (en) 2013-06-11 2018-05-01 Renewable Energy Group, Inc. Methods and devices for producing biodiesel and products obtained therefrom
CN110087475A (en) * 2016-11-17 2019-08-02 阿比尔技术公司 The composition and preparation method thereof formed by plant extracts
US11767278B2 (en) 2015-12-10 2023-09-26 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US11812758B2 (en) 2015-05-20 2023-11-14 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US11827591B2 (en) 2020-10-30 2023-11-28 Apeel Technology, Inc. Compositions and methods of preparation thereof

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654767A (en) * 1950-03-18 1953-10-06 Sherwin Williams Co Process of alcoholysis
US8088183B2 (en) 2003-01-27 2012-01-03 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US9725397B2 (en) 2003-01-27 2017-08-08 REG Seneca, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
US8728177B2 (en) 2003-01-27 2014-05-20 Seneca Landlord, L.L.C. Production of biodiesel and glycerin from high free fatty acid feedstocks
US7806945B2 (en) 2003-01-27 2010-10-05 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US7871448B2 (en) 2003-01-27 2011-01-18 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
WO2006107407A1 (en) * 2005-04-04 2006-10-12 Renewable Products Development Laboratories, Inc. Process and system for producing biodiesel or fatty acid esters from multiple trigi yceride feedstocks
US7619104B2 (en) 2005-04-04 2009-11-17 Renewable Products Development Laboratories, Inc. Process for producing biodiesel or fatty acid esters from multiple triglyceride feedstocks
CN105647656A (en) * 2006-08-15 2016-06-08 Reg辛尼卡有限责任公司 Production method of biodiesel and glycerin from high free fatty acid feedstocks
AU2007205806B2 (en) * 2006-08-15 2010-03-04 REG Seneca, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
JP2008111098A (en) * 2006-08-15 2008-05-15 Nova Biosource Technologies Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
EP1889899A1 (en) 2006-08-15 2008-02-20 NOVA Biosource Technologies, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
US9957464B2 (en) 2013-06-11 2018-05-01 Renewable Energy Group, Inc. Methods and devices for producing biodiesel and products obtained therefrom
US10450533B2 (en) 2013-06-11 2019-10-22 Renewable Energy Group, Inc. Methods and devices for producing biodiesel and products obtained therefrom
US11812758B2 (en) 2015-05-20 2023-11-14 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US11767278B2 (en) 2015-12-10 2023-09-26 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
CN110087475A (en) * 2016-11-17 2019-08-02 阿比尔技术公司 The composition and preparation method thereof formed by plant extracts
US11319275B2 (en) 2016-11-17 2022-05-03 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
CN110087475B (en) * 2016-11-17 2023-04-11 阿比尔技术公司 Composition comprising plant extracts and its preparation method
US11918003B2 (en) 2016-11-17 2024-03-05 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US11827591B2 (en) 2020-10-30 2023-11-28 Apeel Technology, Inc. Compositions and methods of preparation thereof

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