CA1147344A - Preparation of glyceride esters - Google Patents
Preparation of glyceride estersInfo
- Publication number
- CA1147344A CA1147344A CA000335669A CA335669A CA1147344A CA 1147344 A CA1147344 A CA 1147344A CA 000335669 A CA000335669 A CA 000335669A CA 335669 A CA335669 A CA 335669A CA 1147344 A CA1147344 A CA 1147344A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- stage
- glycidol
- fatty acid
- carried out
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 125000005456 glyceride group Chemical group 0.000 title abstract description 5
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 18
- 239000000194 fatty acid Substances 0.000 claims abstract description 18
- 229930195729 fatty acid Natural products 0.000 claims abstract description 18
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 18
- -1 glycidol ester Chemical class 0.000 claims abstract description 18
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 230000010933 acylation Effects 0.000 claims abstract description 10
- 238000005917 acylation reaction Methods 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 125000000466 oxiranyl group Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003208 petroleum Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000036647 reaction Effects 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 8
- 235000021588 free fatty acids Nutrition 0.000 abstract description 6
- 239000004593 Epoxy Substances 0.000 abstract description 3
- 239000003925 fat Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- 229940022682 acetone Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NGEZPLCPKXKLQQ-VOTSOKGWSA-N (e)-4-(3-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=CC(\C=C\C(C)=O)=C1 NGEZPLCPKXKLQQ-VOTSOKGWSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VWYIWOYBERNXLX-KTKRTIGZSA-N Glycidyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CO1 VWYIWOYBERNXLX-KTKRTIGZSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical group COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OUQGOXCIUOCDNN-UHFFFAOYSA-N Glycidyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1CO1 OUQGOXCIUOCDNN-UHFFFAOYSA-N 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- OCNZHGHKKQOQCZ-CLFAGFIQSA-N [(z)-octadec-9-enoyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(=O)CCCCCCC\C=C/CCCCCCCC OCNZHGHKKQOQCZ-CLFAGFIQSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37337/78 | 1978-09-19 | ||
| GB7837337 | 1978-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1147344A true CA1147344A (en) | 1983-05-31 |
Family
ID=10499773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000335669A Expired CA1147344A (en) | 1978-09-19 | 1979-09-14 | Preparation of glyceride esters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4234498A (OSRAM) |
| EP (1) | EP0009904B1 (OSRAM) |
| JP (1) | JPS5543091A (OSRAM) |
| AT (1) | ATE3766T1 (OSRAM) |
| AU (1) | AU529924B2 (OSRAM) |
| CA (1) | CA1147344A (OSRAM) |
| DE (2) | DE2965669D1 (OSRAM) |
| DK (1) | DK388779A (OSRAM) |
| FR (1) | FR2436771A1 (OSRAM) |
| GB (1) | GB2031888B (OSRAM) |
| IE (1) | IE48833B1 (OSRAM) |
| NL (1) | NL7906916A (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014308B1 (de) * | 1979-02-03 | 1983-01-26 | Hüls Troisdorf Aktiengesellschaft | Biologisch abbaubare, oxidationsstabile, flüssige Estergemische mit niedrigen Trübungspunkten und deren Herstellung |
| JPS6453407U (OSRAM) * | 1987-09-30 | 1989-04-03 | ||
| DE4018220A1 (de) * | 1990-06-07 | 1991-12-12 | Solvay Werke Gmbh | Verfahren zur herstellung von monofettsaeure- oder hydroxymonofettsaeureestern von isopropylidenderivaten eines polyglycerins |
| US6255262B1 (en) * | 1998-11-09 | 2001-07-03 | Exxon Chemical Patents Inc. | High hydroxyl content glycerol di-esters |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2695915A (en) * | 1954-11-30 | Esters of oxypropylated glycerol | ||
| US2448602A (en) * | 1943-08-21 | 1948-09-07 | Us Agriculture | Glycidyl esters |
| US2523309A (en) * | 1949-01-25 | 1950-09-26 | Ernest B Kester | Preparation of diglycerides |
| US2910490A (en) * | 1956-10-16 | 1959-10-27 | Jefferson Chem Co Inc | Process for preparing glycol monoesters of organic carboxylic acids |
| US3251870A (en) * | 1962-08-07 | 1966-05-17 | Benj T Rauber | Method of forming monoglycerides of carboxylic organic acids |
| US3238184A (en) * | 1963-04-10 | 1966-03-01 | Standard Oil Co | 4-(epoxyalkyl) methyl esters of trimellitic anhydrides and homopolymers thereof |
| US3845087A (en) * | 1970-11-13 | 1974-10-29 | Lever Brothers Ltd | Isomerization of 1,2-diglycerides to 1,3-diglycerides |
| US3796736A (en) * | 1971-07-21 | 1974-03-12 | Ethyl Corp | Ester synthesis for preparation of synthetic fats |
| DE2449847B2 (de) * | 1974-10-19 | 1978-12-21 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von sehr reinen Carbonsäure-1-monoglyceriden |
| US4154749A (en) * | 1977-07-08 | 1979-05-15 | Aarjis Poefabrik A/S | Method for catalytic rearrangement of 1,2-diglycerides into 1,3-diglycerides |
-
1979
- 1979-09-14 CA CA000335669A patent/CA1147344A/en not_active Expired
- 1979-09-14 US US06/075,572 patent/US4234498A/en not_active Expired - Lifetime
- 1979-09-17 JP JP11800579A patent/JPS5543091A/ja active Pending
- 1979-09-17 GB GB7932148A patent/GB2031888B/en not_active Expired
- 1979-09-17 DE DE7979301908T patent/DE2965669D1/de not_active Expired
- 1979-09-17 NL NL7906916A patent/NL7906916A/nl not_active Application Discontinuation
- 1979-09-17 FR FR7923115A patent/FR2436771A1/fr active Granted
- 1979-09-17 AT AT79301908T patent/ATE3766T1/de not_active IP Right Cessation
- 1979-09-17 DE DE19792937516 patent/DE2937516A1/de not_active Withdrawn
- 1979-09-17 EP EP79301908A patent/EP0009904B1/en not_active Expired
- 1979-09-18 IE IE1767/79A patent/IE48833B1/en unknown
- 1979-09-18 DK DK388779A patent/DK388779A/da not_active Application Discontinuation
- 1979-09-19 AU AU50961/79A patent/AU529924B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IE791767L (en) | 1980-03-19 |
| AU5096179A (en) | 1980-03-27 |
| US4234498A (en) | 1980-11-18 |
| JPS5543091A (en) | 1980-03-26 |
| IE48833B1 (en) | 1985-05-29 |
| GB2031888B (en) | 1983-01-19 |
| FR2436771A1 (fr) | 1980-04-18 |
| AU529924B2 (en) | 1983-06-23 |
| DK388779A (da) | 1980-03-20 |
| EP0009904B1 (en) | 1983-06-15 |
| FR2436771B1 (OSRAM) | 1983-07-22 |
| GB2031888A (en) | 1980-04-30 |
| NL7906916A (nl) | 1980-03-21 |
| DE2937516A1 (de) | 1980-03-27 |
| ATE3766T1 (de) | 1983-06-15 |
| EP0009904A1 (en) | 1980-04-16 |
| DE2965669D1 (en) | 1983-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |