JPS63287749A - ヒマワリ脂肪油を用いる脂肪酸モノグリセリドの製法 - Google Patents

ヒマワリ脂肪油を用いる脂肪酸モノグリセリドの製法

Info

Publication number: JPS63287749A
Authority: JP; Japan
Prior art keywords: acid; fatty acid; weight; fatty; glycerol
Prior art date: 1987-05-08
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.): Pending

Application number

JP63113412A

Other languages

English (en)

Japanese (ja)

Inventor

ホルスト・アイヤーダンツ

ハンス・プファイファー

ミヒャエル・フォークト

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.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

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.)

1987-05-08

Filing date

1988-05-09

Publication date

1988-11-24

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6327129&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPS63287749(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-05-09 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1988-11-24 Publication of JPS63287749A publication Critical patent/JPS63287749A/ja

Status Pending legal-status Critical Current

Links

235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 31
229930195729 fatty acid Natural products 0.000 title claims abstract description 31
239000000194 fatty acid Substances 0.000 title claims abstract description 31
150000004665 fatty acids Chemical class 0.000 title claims abstract description 15
241000208818 Helianthus Species 0.000 title claims description 6
235000003222 Helianthus annuus Nutrition 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title description 6
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 title description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 36
-1 fatty acid monoglycerides Chemical class 0.000 claims abstract description 16
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 15
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 12
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 12
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 12
239000005642 Oleic acid Substances 0.000 claims abstract description 12
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 12
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 12
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims abstract description 7
235000020778 linoleic acid Nutrition 0.000 claims abstract description 7
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims abstract description 7
239000010685 fatty oil Substances 0.000 claims description 13
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
235000021355 Stearic acid Nutrition 0.000 claims description 5
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 5
239000008117 stearic acid Substances 0.000 claims description 5
SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 4
BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 claims description 3
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 3
URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 3
235000021314 Palmitic acid Nutrition 0.000 claims description 3
DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 3
235000020661 alpha-linolenic acid Nutrition 0.000 claims description 3
BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 claims description 3
229940108623 eicosenoic acid Drugs 0.000 claims description 3
DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 3
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 3
229960004488 linolenic acid Drugs 0.000 claims description 3
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
235000021319 Palmitoleic acid Nutrition 0.000 claims description 2
SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
230000004130 lipolysis Effects 0.000 claims description 2
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
235000019197 fats Nutrition 0.000 abstract description 5
230000003647 oxidation Effects 0.000 abstract description 5
238000007254 oxidation reaction Methods 0.000 abstract description 5
230000001804 emulsifying effect Effects 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 abstract description 3
238000005809 transesterification reaction Methods 0.000 abstract description 3
230000007717 exclusion Effects 0.000 abstract 1
239000000839 emulsion Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
230000001590 oxidative effect Effects 0.000 description 5
239000003925 fat Substances 0.000 description 4
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 4
239000003760 tallow Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
235000013305 food Nutrition 0.000 description 3
230000006698 induction Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000000034 method Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
230000009967 tasteless effect Effects 0.000 description 2
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 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
235000008429 bread Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
235000013384 milk substitute Nutrition 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 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
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
- 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
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol

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)
Fats And Perfumes (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Edible Oils And Fats (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

JP63113412A 1987-05-08 1988-05-09 ヒマワリ脂肪油を用いる脂肪酸モノグリセリドの製法 Pending JPS63287749A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3715424.9		1987-05-08
DE3715424A DE3715424C2 (de)	1987-05-08	1987-05-08	Verwendung eines fetten Öles aus Helianthus annuus zur Herstellung von Fettsäure-Monoglyceriden

Publications (1)

Publication Number	Publication Date
JPS63287749A true JPS63287749A (ja)	1988-11-24

Family

ID=6327129

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63113412A Pending JPS63287749A (ja)	1987-05-08	1988-05-09	ヒマワリ脂肪油を用いる脂肪酸モノグリセリドの製法

Country Status (6)

Country	Link
EP (1)	EP0289968B1 (fr)
JP (1)	JPS63287749A (fr)
AT (1)	ATE62016T1 (fr)
CA (1)	CA1313381C (fr)
DE (2)	DE3715424C2 (fr)
ES (1)	ES2021786B3 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4236340C2 (de) *	1992-10-28	1994-11-10	Daimler Benz Ag	Anordnung zur induktiven Übertragung von Energie
GB9416846D0 (en) *	1994-08-19	1994-10-12	Croda Int Plc	Lipid supplementation
FR2750159B1 (fr) *	1996-06-24	1998-08-07	Inst Francais Du Petrole	Methode et systeme d'estimation en temps reel d'au moins un parametre lie au comportement d'un outil de fond de puits
FR2752850A1 (fr) *	1996-08-27	1998-03-06	Inst Francais Du Petrole	Compositions d'additifs ameliorant le pouvoir lubrifiant des carburants et carburants les contenant
WO2017085737A1 (fr) *	2015-11-19	2017-05-26	Fine Research & Development Centre Pvt Ltd	Monoglycéride naturel présentant une odeur et un arôme améliorés

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2789119A (en) *	1954-02-09	1957-04-16	Boake Roberts & Co Ltd	Production of fatty acid monoglycerides
DE1099520B (de) *	1957-01-04	1961-02-16	E F Drew & Co Inc	Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen
US2976251A (en) *	1957-04-19	1961-03-21	Eastman Kodak Co	Glycerol fatty acid partial ester gels
US4627192B1 (en) *	1984-11-16	1995-10-17	Sigco Res Inc	Sunflower products and methods for their production

1987
- 1987-05-08 DE DE3715424A patent/DE3715424C2/de not_active Expired - Fee Related
1988
- 1988-04-30 AT AT88106971T patent/ATE62016T1/de not_active IP Right Cessation
- 1988-04-30 DE DE8888106971T patent/DE3862147D1/de not_active Revoked
- 1988-04-30 EP EP88106971A patent/EP0289968B1/fr not_active Expired - Lifetime
- 1988-04-30 ES ES88106971T patent/ES2021786B3/es not_active Expired - Lifetime
- 1988-05-09 CA CA000566299A patent/CA1313381C/fr not_active Expired - Fee Related
- 1988-05-09 JP JP63113412A patent/JPS63287749A/ja active Pending

Also Published As

Publication number	Publication date
DE3715424A1 (de)	1988-11-17
EP0289968B1 (fr)	1991-03-27
ATE62016T1 (de)	1991-04-15
CA1313381C (fr)	1993-02-02
ES2021786B3 (es)	1991-11-16
DE3715424C2 (de)	1995-01-26
EP0289968A1 (fr)	1988-11-09
DE3862147D1 (de)	1991-05-02

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JPS63287749A (ja)	1988-11-24	ヒマワリ脂肪油を用いる脂肪酸モノグリセリドの製法
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Golumbic et al.	1946	Flavor reversion in soybean oil: III. The preparation and flavor characteristics of a simulated soybean oil
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