GB590386A - Acylation of ricinoleic esters - Google Patents
Acylation of ricinoleic estersInfo
- Publication number
- GB590386A GB590386A GB328145A GB328145A GB590386A GB 590386 A GB590386 A GB 590386A GB 328145 A GB328145 A GB 328145A GB 328145 A GB328145 A GB 328145A GB 590386 A GB590386 A GB 590386A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ricinoleate
- alcohol
- butyl
- isopropyl
- butanol
- 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
- 150000002148 esters Chemical class 0.000 title abstract 5
- 238000005917 acylation reaction Methods 0.000 title 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 6
- 150000001298 alcohols Chemical class 0.000 abstract 5
- QWDBCIAVABMJPP-UHFFFAOYSA-N Diisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)C QWDBCIAVABMJPP-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- SDYPTODXHIAHDF-ACQXMXPUSA-N propan-2-yl (Z,12R)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(C)C SDYPTODXHIAHDF-ACQXMXPUSA-N 0.000 abstract 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 2
- 229940066675 Ricinoleate Drugs 0.000 abstract 2
- -1 alkyl ricinoleate Chemical compound 0.000 abstract 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 230000001264 neutralization Effects 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical group CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 abstract 1
- ZIEDMCIGKVGARL-HKCQKRHBSA-N C(C1=CC=CC=C1)(=O)C(C(=O)OCCCC)CCCCCCC=C/C[C@H](O)CCCCCC Chemical compound C(C1=CC=CC=C1)(=O)C(C(=O)OCCCC)CCCCCCC=C/C[C@H](O)CCCCCC ZIEDMCIGKVGARL-HKCQKRHBSA-N 0.000 abstract 1
- IUXCCQIZNDRFRE-UHFFFAOYSA-N C(C1CCCO1)OCC1CCCO1.[K] Chemical compound C(C1CCCO1)OCC1CCCO1.[K] IUXCCQIZNDRFRE-UHFFFAOYSA-N 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N Tetrahydro-2-furanmethanol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 abstract 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N Triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 abstract 1
- 229960002622 Triacetin Drugs 0.000 abstract 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- ILCRHUJGVUEAKX-UHFFFAOYSA-N butan-1-ol;butyl acetate Chemical compound CCCCO.CCCCOC(C)=O ILCRHUJGVUEAKX-UHFFFAOYSA-N 0.000 abstract 1
- BEWFIPLBFJGWSR-AONZOJHOSA-N butyl (Z,12R)-12-acetyloxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](OC(C)=O)C\C=C/CCCCCCCC(=O)OCCCC BEWFIPLBFJGWSR-AONZOJHOSA-N 0.000 abstract 1
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 239000001087 glyceryl triacetate Substances 0.000 abstract 1
- 235000013773 glyceryl triacetate Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 abstract 1
- IJLPNKIVCXEQPA-UHFFFAOYSA-N sodium;butane Chemical compound [Na+].CCC[CH2-] IJLPNKIVCXEQPA-UHFFFAOYSA-N 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Abstract
Ricinoleic esters are acylated by heating with a neutral ester of another carboxylic acid in presence of an alkali metal alcohol oxide such as sodium methoxide or potassium tetrahydrofurfuryloxide. The ricinoleic ester may be any substantially neutral ester of the total fatty acids of castor oil or a concentrate thereof with a saturated aliphatic, unsaturated or cyclic alcohol, e.g. methallyl, benzyl or tetrahydrofurfuryl alcohol or cyclohexanol, or a substituted alcohol such as b -ethoxyethanol. In addition to alcoholysis, interchange of alcohols may occur. The boiling points of the combined alcohols advantageously differ considerably while said alcohols are of low alcoholysing character such as secondary or b g -unsaturated alcohols. Thus, an alkyl-phthalyl alkyl ricinoleate is prepared from isopropyl ricinoleate and diisopropyl phthalate. The other carboxylic acid may be, for example, acetic, propionic, butyric, benzoic, furoic, phthalic, succinic, maleic, adipic, sebacic and tricarballylic. To obtain high conversion, considerable excess of a reagent or volatilisation of a displaced alcohol is necessary. In examples: (1) castor oil, excess of butyl acetate, and sodium in butanol are fractionated with distillation of a butanol-butyl acetate azeotrope giving butyl acetylricinoleate, monoricinolein triacetate and triacetin; (2) isopropyl ricinoleate, diisopropyl phthalate, and sodium in isopropyl alcohol are heated at 130 DEG C. in vacuum, isopropanol being removed and isopropylphthalyl isopropyl ricinoleate formed with, if less than an equimolar proportion of diisopropylphthalate is used, some phthalyl bis-(isopropyl ricinoleate); (3) equimolar amounts of butyl ricinoleate and butyl benzoate with sodium in butanol are heated in vacuum at 100 DEG C. with elimination of butanol and formation of butyl benzoyl-ricinoleate.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB590386A true GB590386A (en) | 1947-07-16 |
Family
ID=1627635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB328145A Expired GB590386A (en) | 1945-02-09 | Acylation of ricinoleic esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB590386A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1132123B (en) * | 1955-06-07 | 1962-06-28 | Inst Francais Du Petrol | Process for the preparation of castor oil fatty acid polyethylene glycol esters suitable as lubricating oils |
| EP1097699A1 (en) * | 1999-11-04 | 2001-05-09 | L'oreal | Cosmetic composition comprising hydroxylated fatty acid ester |
| EP2048219A1 (en) * | 2007-10-10 | 2009-04-15 | Bayer MaterialScience AG | Low viscous ester mixture |
| US20110282084A1 (en) * | 2008-05-14 | 2011-11-17 | Council Of Scientific & Industrial Research | Castor oil fatty acid based estolide esters and their derivatives as potential lubricant base stocks |
-
1945
- 1945-02-09 GB GB328145A patent/GB590386A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1132123B (en) * | 1955-06-07 | 1962-06-28 | Inst Francais Du Petrol | Process for the preparation of castor oil fatty acid polyethylene glycol esters suitable as lubricating oils |
| EP1097699A1 (en) * | 1999-11-04 | 2001-05-09 | L'oreal | Cosmetic composition comprising hydroxylated fatty acid ester |
| FR2800608A1 (en) * | 1999-11-04 | 2001-05-11 | Oreal | COSMETIC COMPOSITION CONTAINING A HYDROXYLATED FATTY ACID ESTER |
| US7250159B1 (en) | 1999-11-04 | 2007-07-31 | L'ORéAL S.A. | Compositions comprising at least one ester of at least one hydroxylated aliphatic compound |
| EP2048219A1 (en) * | 2007-10-10 | 2009-04-15 | Bayer MaterialScience AG | Low viscous ester mixture |
| WO2009049763A1 (en) * | 2007-10-10 | 2009-04-23 | Bayer Materialscience Ag | Low viscosity ester mixtures |
| US20110282084A1 (en) * | 2008-05-14 | 2011-11-17 | Council Of Scientific & Industrial Research | Castor oil fatty acid based estolide esters and their derivatives as potential lubricant base stocks |
| US8742150B2 (en) * | 2008-05-14 | 2014-06-03 | Council Of Scientific & Industrial Research | Castor oil fatty acid based estolide esters and their derivatives as potential lubricant base stocks |
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