DE2939663C2 - - Google Patents
Info
- Publication number
- DE2939663C2 DE2939663C2 DE19792939663 DE2939663A DE2939663C2 DE 2939663 C2 DE2939663 C2 DE 2939663C2 DE 19792939663 DE19792939663 DE 19792939663 DE 2939663 A DE2939663 A DE 2939663A DE 2939663 C2 DE2939663 C2 DE 2939663C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mol
- sec
- mixtures
- hydroxyl
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 33
- 150000002148 esters Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 18
- -1 saturated aliphatic monocarboxylic acid Chemical class 0.000 claims description 16
- 230000032050 esterification Effects 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000001384 succinic acid Substances 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 description 21
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 150000004665 fatty acids Chemical class 0.000 description 16
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 12
- 235000013162 Cocos nucifera Nutrition 0.000 description 11
- 244000060011 Cocos nucifera Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000001361 adipic acid Substances 0.000 description 10
- 235000011037 adipic acid Nutrition 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000011261 inert gas Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000009967 tasteless effect Effects 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001536 azelaic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material 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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792939663 DE2939663A1 (de) | 1979-09-29 | 1979-09-29 | Biologisch abbaubare, oxidationsstabile, fluessige estergemische mit niedrigen truebungspunkten und guten visksitaetsindices |
| DE8080100031T DE3061696D1 (en) | 1979-02-03 | 1980-01-04 | Fluid, biodegradable ester mixtures resistant to oxidation, with low cloud points, and their preparation |
| EP80100031A EP0014308B1 (de) | 1979-02-03 | 1980-01-04 | Biologisch abbaubare, oxidationsstabile, flüssige Estergemische mit niedrigen Trübungspunkten und deren Herstellung |
| DD80218686A DD148766A5 (de) | 1979-02-03 | 1980-01-28 | Biologisch abbaubare,oxidationsstabile fluessige estergemische mit niedrigen truebungspunkten und deren herstellung |
| CA000344955A CA1140577A (en) | 1979-02-03 | 1980-02-01 | Biodegradable, oxidation-resistant liquid ester mixtures with low turbidity points |
| SE8000823A SE8000823L (sv) | 1979-02-03 | 1980-02-01 | Biologiskt nedbrytbara oxidationsstabila, flytande esterblandningar med lag grumlingspunkt och forfarande for framstellning derav |
| DK44380A DK44380A (da) | 1979-02-03 | 1980-02-01 | Biologisk fuldstaendigt nedbrydelige toxikologisk uskadelige oxidationsstabile smags og lugteneutrale llare flydende ensartede esterblandinger med lave uklarhedspunkter |
| ES488205A ES488205A0 (es) | 1979-02-03 | 1980-02-01 | Procedimiento para la preparacion de nuevas mezclas de este-res |
| PL22216080A PL222160A1 (en, 2012) | 1979-09-29 | 1980-02-21 | |
| US06/280,028 US4366100A (en) | 1979-02-03 | 1981-07-02 | Biodegradable, oxidation-resistant liquid ester mixtures with low turbidity points |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792939663 DE2939663A1 (de) | 1979-09-29 | 1979-09-29 | Biologisch abbaubare, oxidationsstabile, fluessige estergemische mit niedrigen truebungspunkten und guten visksitaetsindices |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2939663A1 DE2939663A1 (de) | 1981-04-09 |
| DE2939663C2 true DE2939663C2 (en, 2012) | 1988-03-10 |
Family
ID=6082322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792939663 Granted DE2939663A1 (de) | 1979-02-03 | 1979-09-29 | Biologisch abbaubare, oxidationsstabile, fluessige estergemische mit niedrigen truebungspunkten und guten visksitaetsindices |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2939663A1 (en, 2012) |
| PL (1) | PL222160A1 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100496494B1 (ko) * | 1995-08-22 | 2005-06-22 | 코그니스 코포레이션 | 무연 2 사이클 엔진 윤활유 |
-
1979
- 1979-09-29 DE DE19792939663 patent/DE2939663A1/de active Granted
-
1980
- 1980-02-21 PL PL22216080A patent/PL222160A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL222160A1 (en, 2012) | 1981-07-24 |
| DE2939663A1 (de) | 1981-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2904164 Format of ref document f/p: P |
|
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2904164 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS TROISDORF AG, 5210 TROISDORF, DE |
|
| 8363 | Opposition against the patent | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8330 | Complete disclaimer |