DE2123929A1 - Verfahren zur Herstellung von Epoxyfettsäureestern - Google Patents
Verfahren zur Herstellung von EpoxyfettsäureesternInfo
- Publication number
- DE2123929A1 DE2123929A1 DE19712123929 DE2123929A DE2123929A1 DE 2123929 A1 DE2123929 A1 DE 2123929A1 DE 19712123929 DE19712123929 DE 19712123929 DE 2123929 A DE2123929 A DE 2123929A DE 2123929 A1 DE2123929 A1 DE 2123929A1
- Authority
- DE
- Germany
- Prior art keywords
- esters
- mixtures
- fatty acid
- acids
- unsaturated
- 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.)
- Pending
Links
- 239000000194 fatty acid Substances 0.000 title claims description 32
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 31
- 229930195729 fatty acid Natural products 0.000 title claims description 31
- 239000004593 Epoxy Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 20
- -1 fatty acid esters Chemical class 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 25
- 150000007513 acids Chemical class 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 16
- 238000005809 transesterification reaction Methods 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 15
- 238000006735 epoxidation reaction Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 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 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000007700 distillative separation Methods 0.000 claims 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000015278 beef Nutrition 0.000 description 9
- 239000003760 tallow Substances 0.000 description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 235000014593 oils and fats Nutrition 0.000 description 4
- 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 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 description 1
- PUYRISKXBBQECH-UHFFFAOYSA-N 2-ethylhexyl 8-(3-octyloxiran-2-yl)octanoate Chemical compound CCCCCCCCC1OC1CCCCCCCC(=O)OCC(CC)CCCC PUYRISKXBBQECH-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 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
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000015096 spirit 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
- 239000010409 thin film Substances 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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
- C07D303/38—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)
- Fats And Perfumes (AREA)
- Epoxy Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712123929 DE2123929A1 (de) | 1971-05-14 | 1971-05-14 | Verfahren zur Herstellung von Epoxyfettsäureestern |
| NL7204956A NL7204956A (enExample) | 1971-05-14 | 1972-04-13 | |
| GB2055972A GB1382853A (en) | 1971-05-14 | 1972-05-03 | Production of epoxy stearic acid esters |
| FR7216847A FR2139440A5 (enExample) | 1971-05-14 | 1972-05-10 | |
| BE783328A BE783328A (fr) | 1971-05-14 | 1972-05-10 | Procede pour la preparation d'esters d'acides gras epoxydes |
| IT5024172A IT957850B (it) | 1971-05-14 | 1972-05-13 | Procedimento per la produzione di esteri di acidi grassi epossi dati |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712123929 DE2123929A1 (de) | 1971-05-14 | 1971-05-14 | Verfahren zur Herstellung von Epoxyfettsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2123929A1 true DE2123929A1 (de) | 1972-11-23 |
Family
ID=5807846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712123929 Pending DE2123929A1 (de) | 1971-05-14 | 1971-05-14 | Verfahren zur Herstellung von Epoxyfettsäureestern |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE783328A (enExample) |
| DE (1) | DE2123929A1 (enExample) |
| FR (1) | FR2139440A5 (enExample) |
| GB (1) | GB1382853A (enExample) |
| IT (1) | IT957850B (enExample) |
| NL (1) | NL7204956A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110146873A1 (en) | 2009-12-22 | 2011-06-23 | Marc Weydert | Pneumatic tire with rubber component containing epoxidized palm oil |
| JP6189967B2 (ja) * | 2012-11-12 | 2017-08-30 | 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を作製するための方法 |
-
1971
- 1971-05-14 DE DE19712123929 patent/DE2123929A1/de active Pending
-
1972
- 1972-04-13 NL NL7204956A patent/NL7204956A/xx unknown
- 1972-05-03 GB GB2055972A patent/GB1382853A/en not_active Expired
- 1972-05-10 FR FR7216847A patent/FR2139440A5/fr not_active Expired
- 1972-05-10 BE BE783328A patent/BE783328A/xx unknown
- 1972-05-13 IT IT5024172A patent/IT957850B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7204956A (enExample) | 1972-11-16 |
| GB1382853A (en) | 1975-02-05 |
| FR2139440A5 (enExample) | 1973-01-05 |
| IT957850B (it) | 1973-10-20 |
| BE783328A (fr) | 1972-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE4132555C2 (de) | Verfahren zur Herstellung einer Dicarbonsäure | |
| DE4209779C1 (enExample) | ||
| DE69808029T2 (de) | Verfahren zum Herstellen von Fettsäureester | |
| DE2009047C2 (de) | Verfahren zur Herstellung von Epoxystearinsäureestern | |
| DE69429093T2 (de) | Rückgewinnung von tocopherolen | |
| EP0184740B1 (de) | Verfahren zur Herstellung von Fettsäuremethylestern | |
| EP1230206B1 (de) | Verfahren zur herstellung von ameisensäure | |
| EP0790230A1 (de) | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure | |
| DE69005501T2 (de) | Verfahren zum Herstellen von Niedrigalkylfettsäuremonoester. | |
| EP1910267B1 (de) | Verfahren zur herstellung von carbonsäurealkylestern | |
| EP0819116B1 (de) | Verfahren zum gewinnen von carotin aus palmöl | |
| EP1179535B1 (de) | Verfahren zur Gewinnung von Sterinen | |
| EP0000916B1 (de) | Verfahren zur Herstellung von Fettsäurenitrilen und Glycerin aus Glyceriden, insbesondere aus natürlichen Fetten und Oelen | |
| EP0291870B1 (de) | Verfahren zur Herstellung von Triglyceriden | |
| DE3879399T2 (de) | Herstellung von trisubstituierten hydroxyalkylalkanoaten aus aldehyden. | |
| EP1092703B1 (de) | Verfahren zur Herstellung von Fettsäuremethylestern | |
| DE10259157A1 (de) | Verfahren zur Herstellung von konjugierter Linolsäure | |
| DE907171C (de) | Verfahren zur Abtrennung sauerstoffhaltiger Verbindungen aus Produkten der katalytrischen Kohlenoxydhydrierung | |
| EP0080023A1 (de) | Verfahren zum kontinuierlichen Verestern von Methacrylsäure | |
| DE2253930A1 (de) | Verfahren zur herstellung von dicarbonsaeuren | |
| DE2111669A1 (de) | Herstellung von Alkoholen | |
| AT210419B (de) | Verfahren zur Herstellung von Pyridincarbonsäurealkylestern | |
| DE1099520B (de) | Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen | |
| DE1593712C3 (de) | Verfahren zur kontinuierlichen Herstellung von o-Phthalsäureestern | |
| DE2740242A1 (de) | Verfahren zur herstellung von dimethylcarbonat |