DE2009047C2 - Verfahren zur Herstellung von Epoxystearinsäureestern - Google Patents
Verfahren zur Herstellung von EpoxystearinsäureesternInfo
- Publication number
- DE2009047C2 DE2009047C2 DE19702009047 DE2009047A DE2009047C2 DE 2009047 C2 DE2009047 C2 DE 2009047C2 DE 19702009047 DE19702009047 DE 19702009047 DE 2009047 A DE2009047 A DE 2009047A DE 2009047 C2 DE2009047 C2 DE 2009047C2
- Authority
- DE
- Germany
- Prior art keywords
- esters
- mixture
- unsaturated
- lower alkanol
- fatty acids
- 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 claims description 44
- IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 9
- 238000006735 epoxidation reaction Methods 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 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 6
- -1 fatty acid ester Chemical class 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 235000014593 oils and fats Nutrition 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 235000015278 beef Nutrition 0.000 description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000005830 nonesterified fatty acids Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000005374 primary esters Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002383 tung oil Substances 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
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702009047 DE2009047C2 (de) | 1970-02-26 | 1970-02-26 | Verfahren zur Herstellung von Epoxystearinsäureestern |
| CH1869670A CH567009A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-02-26 | 1970-12-17 | |
| NL7100320A NL171705C (nl) | 1970-02-26 | 1971-01-11 | Werkwijze voor het bereiden van epoxystearinezuuresters. |
| BE763422A BE763422A (fr) | 1970-02-26 | 1971-02-24 | Procede pour la preparation d'esters d'acides gras epoxydes |
| AT161871A AT305962B (de) | 1970-02-26 | 1971-02-25 | Verfahren zur Herstellung von Epoxyfettsäureestern |
| FR7106801A FR2079133A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-02-26 | 1971-02-26 | |
| CA106405A CA933938A (en) | 1970-02-26 | 1971-02-26 | Process for producing esters of epoxy fatty acids |
| GB2203571A GB1341623A (en) | 1970-02-26 | 1971-04-19 | Production of esters of epoyidised stearic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702009047 DE2009047C2 (de) | 1970-02-26 | 1970-02-26 | Verfahren zur Herstellung von Epoxystearinsäureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2009047A1 DE2009047A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-02 |
| DE2009047C2 true DE2009047C2 (de) | 1982-04-08 |
Family
ID=5763464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702009047 Expired DE2009047C2 (de) | 1970-02-26 | 1970-02-26 | Verfahren zur Herstellung von Epoxystearinsäureestern |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19542933A1 (de) * | 1995-11-17 | 1997-05-22 | Buna Sow Leuna Olefinverb Gmbh | Glycidester-ester, Verfahren zu ihrer Herstellung und ihre Verwendung |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0215581A (pt) * | 2002-12-06 | 2004-12-21 | Cognis Brasil Ltda | Composições plastificantes para resinas baseadas em nitrocelulose |
| US7700675B2 (en) | 2002-12-06 | 2010-04-20 | Cognis Brazil Ltda | Plasticized poly vinyl chloride compositions |
| CA2715287C (en) | 2008-02-15 | 2016-01-05 | Union Carbide Chemicals & Plastics Technology Llc | A replacement plasticizer system for phthalate-plasticized formulations |
| EP2483341B1 (en) | 2009-09-30 | 2013-07-17 | Dow Global Technologies LLC | Acetylated derivatives of castor oil and their blends with epoxidized fatty acid esters |
| US8552098B2 (en) | 2009-09-30 | 2013-10-08 | Dow Global Technologies Llc | Purified acetylated derivatives of castor oil and compositions including same |
| TWI607048B (zh) | 2009-09-30 | 2017-12-01 | 陶氏全球科技有限責任公司 | 具有經環氧化之脂肪酸酯塑化劑的熱穩定聚合組成物 |
| US9422418B2 (en) | 2009-09-30 | 2016-08-23 | Dow Global Technologies Llc | Acetylated monoglyceride of 12-hydroxystearic acid and blends with epoxidized fatty acid esters |
| CN102762707B (zh) | 2009-12-17 | 2014-09-24 | Npc化工有限公司 | 使植物油改性的方法和用于乙烯基聚合物的主增塑剂 |
| KR101825239B1 (ko) | 2010-05-10 | 2018-02-02 | 다우 글로벌 테크놀로지스 엘엘씨 | 재생가능한 원천으로부터 유래된 가소제로 제조된 유연성 ｐⅴｃ 조성물 |
| TW201209168A (en) | 2010-07-28 | 2012-03-01 | Dow Global Technologies Llc | Plasticizers made from oil extracted from microorganisms and polar polymeric compositions comprising the same |
| US20150005420A1 (en) | 2012-02-08 | 2015-01-01 | Dow Global Technologies Llc | Plasticizer compositions and methods for making plasticizer compositions |
| CA2872522C (en) | 2012-06-22 | 2020-09-01 | Dow Global Technologies Llc | Acetylated polyol hydroxystearate plasticizers and plasticized polymeric compositions |
| BR112014027891B1 (pt) | 2012-06-26 | 2021-03-23 | Dow Global Technologies Llc | Composição de cloreto de vinila polimérica plastificada e condutor revestido |
| MX370205B (es) | 2012-10-18 | 2019-12-05 | Dow Global Technologies Llc | Plastificantes de alquil esteres de acidos grasos epoxidados y metodos para hacer plastificantes de alquil esteres de acidos grasos epoxidados. |
| CN104781328B (zh) | 2012-11-12 | 2017-12-05 | 陶氏环球技术有限公司 | 制造环氧化脂肪酸烷基酯的方法 |
| JP6192733B2 (ja) | 2012-11-12 | 2017-09-06 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ化脂肪酸アルキルエステル可塑剤およびエポキシ化脂肪酸アルキルエステル可塑剤を作製するための方法 |
| CN103319439A (zh) * | 2013-04-12 | 2013-09-25 | 常州南京大学高新技术研究院 | 一种制备环氧脂肪酸环己酯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT518630A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1950-08-23 | |||
| DE1135895B (de) * | 1957-11-13 | 1962-09-06 | Union Carbide Corp | Verfahren zur Herstellung eines 2, 3-Epoxyalkancarbonsaeureesters eines Alkenols |
| US3377304A (en) * | 1959-04-22 | 1968-04-09 | Swift & Co | High oxirane fatty esters |
| NL302305A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-12-20 | 1900-01-01 | British Celanese |
-
1970
- 1970-02-26 DE DE19702009047 patent/DE2009047C2/de not_active Expired
- 1970-12-17 CH CH1869670A patent/CH567009A5/xx not_active IP Right Cessation
-
1971
- 1971-01-11 NL NL7100320A patent/NL171705C/xx not_active IP Right Cessation
- 1971-02-24 BE BE763422A patent/BE763422A/xx not_active IP Right Cessation
- 1971-02-25 AT AT161871A patent/AT305962B/de not_active IP Right Cessation
- 1971-02-26 FR FR7106801A patent/FR2079133A5/fr not_active Expired
- 1971-02-26 CA CA106405A patent/CA933938A/en not_active Expired
- 1971-04-19 GB GB2203571A patent/GB1341623A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19542933A1 (de) * | 1995-11-17 | 1997-05-22 | Buna Sow Leuna Olefinverb Gmbh | Glycidester-ester, Verfahren zu ihrer Herstellung und ihre Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| BE763422A (fr) | 1971-08-24 |
| NL171705B (nl) | 1982-12-01 |
| DE2009047A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-02 |
| NL171705C (nl) | 1983-05-02 |
| AT305962B (de) | 1973-03-26 |
| NL7100320A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-30 |
| GB1341623A (en) | 1973-12-25 |
| CA933938A (en) | 1973-09-18 |
| CH567009A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-30 |
| FR2079133A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8126 | Change of the secondary classification |
Ipc: C07D301/14 |
|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |