DD232913A5 - Verfahren zur herstellung von fettsaeureestern kurzkettige alkohole - Google Patents

Verfahren zur herstellung von fettsaeureestern kurzkettige alkohole Download PDF

Info

Publication number: DD232913A5
Authority: DD; German Democratic Republic
Prior art keywords: fatty acid; alcohol; reaction; glyceride; glycerol
Prior art date: 1984-06-07

Application number

DD85277054A

Other languages

German (de)

English (en)

Inventor

Siegfried Billenstein

Bruno Kukla

Herbert Stuehler

Original Assignee

Hoechst Ag

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.)

1984-06-07

Filing date

1985-06-05

Publication date

1986-02-12

1985-06-05 Application filed by Hoechst Ag filed Critical Hoechst Ag

1986-02-12 Publication of DD232913A5 publication Critical patent/DD232913A5/de

Links

235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 30
239000000194 fatty acid Substances 0.000 title claims abstract description 30
229930195729 fatty acid Natural products 0.000 title claims abstract description 30
-1 FATTY ACID ESTERS Chemical class 0.000 title claims abstract description 25
150000001298 alcohols Chemical class 0.000 title claims abstract description 12
238000004519 manufacturing process Methods 0.000 title description 5
238000006243 chemical reaction Methods 0.000 claims abstract description 50
238000000034 method Methods 0.000 claims abstract description 46
125000005456 glyceride group Chemical group 0.000 claims abstract description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
239000000203 mixture Substances 0.000 claims abstract description 14
238000005809 transesterification reaction Methods 0.000 claims abstract description 12
239000007788 liquid Substances 0.000 claims abstract description 8
238000005191 phase separation Methods 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 5
150000003138 primary alcohols Chemical class 0.000 claims abstract description 4
150000003333 secondary alcohols Chemical class 0.000 claims abstract description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 123
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
239000003054 catalyst Substances 0.000 claims description 15
238000009833 condensation Methods 0.000 claims description 13
230000005494 condensation Effects 0.000 claims description 13
150000004665 fatty acids Chemical class 0.000 claims description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 3
235000011187 glycerol Nutrition 0.000 description 41
239000003925 fat Substances 0.000 description 28
235000019197 fats Nutrition 0.000 description 28
239000002253 acid Substances 0.000 description 17
239000003760 tallow Substances 0.000 description 11
150000007513 acids Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 8
239000003921 oil Substances 0.000 description 7
238000000926 separation method Methods 0.000 description 7
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000007789 gas Substances 0.000 description 6
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
235000021588 free fatty acids Nutrition 0.000 description 5
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 5
239000000344 soap Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229920000715 Mucilage Polymers 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
239000003513 alkali Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
235000019387 fatty acid methyl ester Nutrition 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
BZUNJUAMQZRJIP-UHFFFAOYSA-N 15-hydroxypentadecanoic acid Chemical compound OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 description 2
UGAGPNKCDRTDHP-UHFFFAOYSA-N 16-hydroxyhexadecanoic acid Chemical compound OCCCCCCCCCCCCCCCC(O)=O UGAGPNKCDRTDHP-UHFFFAOYSA-N 0.000 description 2
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical compound CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
235000019484 Rapeseed oil Nutrition 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000019486 Sunflower oil Nutrition 0.000 description 2
UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
235000019864 coconut oil Nutrition 0.000 description 2
238000011109 contamination Methods 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
230000008021 deposition Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
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 2
229910001385 heavy metal Inorganic materials 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
239000004006 olive oil Substances 0.000 description 2
235000008390 olive oil Nutrition 0.000 description 2
229960003656 ricinoleic acid Drugs 0.000 description 2
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
239000002600 sunflower oil Substances 0.000 description 2
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
230000007704 transition Effects 0.000 description 2
VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 2
DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
238000011144 upstream manufacturing Methods 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
UBEIMDKGOYBUKT-FLIQGJDUSA-N 1,2,3-trilinolenoylglycerol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC UBEIMDKGOYBUKT-FLIQGJDUSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
MUMWRBGBCHMKOL-UHFFFAOYSA-N 12-hexyloctadecanoic acid Chemical compound CCCCCCC(CCCCCC)CCCCCCCCCCC(O)=O MUMWRBGBCHMKOL-UHFFFAOYSA-N 0.000 description 1
KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
ONEKODVPFBOORO-UHFFFAOYSA-N 2-methyl lauric acid Chemical class CCCCCCCCCCC(C)C(O)=O ONEKODVPFBOORO-UHFFFAOYSA-N 0.000 description 1
SAOSCTYRONNFTC-UHFFFAOYSA-N 2-methyl-decanoic acid Chemical class CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 1
GBZDALHFANHWOF-UHFFFAOYSA-N 2-methyloctadecanoic acid Chemical class CCCCCCCCCCCCCCCCC(C)C(O)=O GBZDALHFANHWOF-UHFFFAOYSA-N 0.000 description 1
BVUBANAQPIROHS-UHFFFAOYSA-N 3,3-dimethyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(C)(C)CC(O)=O BVUBANAQPIROHS-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
LXKCZUOSRQSRHW-UHFFFAOYSA-N 6-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCC(O)CCCCC(O)=O LXKCZUOSRQSRHW-UHFFFAOYSA-N 0.000 description 1
YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
101100536695 Gallus gallus TENP gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 description 1
239000005639 Lauric acid Substances 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
235000008753 Papaver somniferum Nutrition 0.000 description 1
240000001090 Papaver somniferum Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000005643 Pelargonic acid Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 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
150000001242 acetic acid derivatives Chemical class 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000012491 analyte Substances 0.000 description 1
235000021302 avocado oil Nutrition 0.000 description 1
239000008163 avocado oil Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
MXSHHHVKQWTICU-UHFFFAOYSA-M cesium;dodecanoate Chemical compound [Cs+].CCCCCCCCCCCC([O-])=O MXSHHHVKQWTICU-UHFFFAOYSA-M 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002360 explosive Substances 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
150000002196 fatty nitriles Chemical class 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
229940013317 fish oils Drugs 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
239000008169 grapeseed oil Substances 0.000 description 1
239000004519 grease Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000010460 hemp oil Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
239000011133 lead Chemical class 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229940074096 monoolein Drugs 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003346 palm kernel oil Substances 0.000 description 1
235000019865 palm kernel oil Nutrition 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
150000002942 palmitic acid derivatives Chemical class 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
239000008171 pumpkin seed oil Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
239000010499 rapseed oil Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
210000002374 sebum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000002884 skin cream Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000004753 textile Substances 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
239000010936 titanium Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000000606 toothpaste Substances 0.000 description 1
229940093609 tricaprylin Drugs 0.000 description 1
PHYFQTYBJUILEZ-WUOFIQDXSA-N trielaidin Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C\CCCCCCCC)COC(=O)CCCCCCC\C=C\CCCCCCCC PHYFQTYBJUILEZ-WUOFIQDXSA-N 0.000 description 1
229940113164 trimyristin Drugs 0.000 description 1
VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 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
229940117972 triolein Drugs 0.000 description 1
229960001947 tripalmitin Drugs 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000010698 whale oil Substances 0.000 description 1
239000010497 wheat germ oil Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
229940098697 zinc laurate Drugs 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
NMOHFBPSMIYLGY-UHFFFAOYSA-L zinc;2-dodecylbenzenesulfonate Chemical group [Zn+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O NMOHFBPSMIYLGY-UHFFFAOYSA-L 0.000 description 1
GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical group [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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 Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Fats And Perfumes (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD85277054A 1984-06-07 1985-06-05 Verfahren zur herstellung von fettsaeureestern kurzkettige alkohole DD232913A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843421217 DE3421217A1 (de)	1984-06-07	1984-06-07	Verfahren zur herstellung von fettsaeureestern kurzkettiger alkohole

Publications (1)

Publication Number	Publication Date
DD232913A5 true DD232913A5 (de)	1986-02-12

Family

ID=6237842

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85277054A DD232913A5 (de)	1984-06-07	1985-06-05	Verfahren zur herstellung von fettsaeureestern kurzkettige alkohole

Country Status (21)

Country	Link
US (1)	US4668439A (fr)
EP (1)	EP0164643B1 (fr)
JP (1)	JPS611640A (fr)
KR (1)	KR910008370B1 (fr)
CN (1)	CN85106282A (fr)
AT (1)	ATE46532T1 (fr)
AU (1)	AU569570B2 (fr)
BR (1)	BR8502693A (fr)
CA (1)	CA1247130A (fr)
DD (1)	DD232913A5 (fr)
DE (2)	DE3421217A1 (fr)
DK (1)	DK254685A (fr)
ES (1)	ES8604094A1 (fr)
MX (1)	MX160996A (fr)
MY (1)	MY100687A (fr)
NO (1)	NO852293L (fr)
NZ (1)	NZ212308A (fr)
PH (1)	PH21080A (fr)
PT (1)	PT80603B (fr)
SU (1)	SU1402250A3 (fr)
ZA (1)	ZA854288B (fr)

Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3515403A1 (de) *	1985-04-29	1986-10-30	Henkel KGaA, 4000 Düsseldorf	Verfahren zur katalytischen umesterung von fettsaeureglyceriden mit niederen alkanolen
DE3707563A1 (de) *	1987-03-10	1988-09-22	Klaus Dr Ing Scharmer	Verfahren zur alkoholyse von fettsaeureglyceriden und vorrichtung zum durchfuehren des verfahrens
US5019668A (en) *	1988-06-14	1991-05-28	Palm Oil Research & Development Board	Recovery of carotenoids
BE1006287A3 (fr) *	1992-04-30	1994-07-12	Gheorghiu Mihail	Procede de fabrication d'esters methyliques d'acides gras a partir d'une huile ou graisse naturelle, esters methyliques tels qu'ainsi obtenus et leur utilisation.
FR2698101B1 (fr) *	1992-11-19	1995-01-06	Arceau Huileries	Procédé de transestérification catalytique de corps gras d'origine végétale ou animale et procédé de récupération des produits obtenus.
DE4301686C1 (de) *	1993-01-22	1994-03-31	Chem & Pharm Patent Hold Ltd	Verfahren zur Herstellung von Fettsäureestern niederer Alkohole
EP0654528A1 (fr) *	1993-11-22	1995-05-24	Mihail Gheorghiu	Procédé de fabrication d'esters méthyliques d'acides gras à partir d'une huile ou graisse naturelle, esters méthyliques tels qu'ainsi obtenus et leur utilisation
US5532392A (en) *	1994-01-13	1996-07-02	Gheorghiu; Mihail	Process for the preparation of methyl fatty acid esters starting from natural oil or fat, methyl esters obtained in this way and use thereof
US5491226A (en) *	1994-04-06	1996-02-13	Procter & Gamble Company	Process for preparing polyol polyesters having low levels of triglycerides
US5648483A (en) *	1995-06-07	1997-07-15	The Procter & Gamble Company	Continuous transesterification method for preparing polyol polyesters
US5844111A (en) *	1995-06-07	1998-12-01	The Procter & Gamble Company	Method for purifying an inert gas while preparing lower alkyl esters
DE19537235A1 (de) *	1995-10-06	1997-04-10	Haarmann & Reimer Gmbh	Verfahren zur Herstellung von trans-2,cis-4-Decadiensäureethylester
US5730029A (en) *	1997-02-26	1998-03-24	The Lubrizol Corporation	Esters derived from vegetable oils used as additives for fuels
US6007856A (en) *	1997-08-08	1999-12-28	The Procter & Gamble Company	Oil-in-water dispersions of β-carotene and other carotenoids stable against oxidation prepared from water-dispersible beadlets having high concentrations of carotenoid
DE69830518T2 (de) *	1997-11-10	2006-03-16	The Procter & Gamble Company, Cincinnati	Verfahren zur herstellung von hochreinen fettsäure-niedrigalkylestern
US6965043B1 (en)	1997-11-10	2005-11-15	Procter + Gamble Co.	Process for making high purity fatty acid lower alkyl esters
US6127560A (en) *	1998-12-29	2000-10-03	West Central Cooperative	Method for preparing a lower alkyl ester product from vegetable oil
US6849581B1 (en)	1999-03-30	2005-02-01	Bj Services Company	Gelled hydrocarbon compositions and methods for use thereof
US6407272B1 (en) *	1999-07-14	2002-06-18	Arizona Chemical Company	Secondary alcohol esters of hydroxyacids and uses thereof
US20020035282A1 (en) *	2000-03-06	2002-03-21	Suppes Galen J.	Carbonate catalyzed alcoholysis of triglycerides
WO2001088072A1 (fr) *	2000-05-15	2001-11-22	Dragan Nimcevic	Transesterification de graisses
JP2002241786A (ja) *	2000-12-15	2002-08-28	Sumitomo Chem Co Ltd	植物の種子および／または果実から脂肪酸エステルを製造する方法
US6965044B1 (en)	2001-07-06	2005-11-15	Iowa State University Research Foundation	Method of converting free fatty acids to fatty acid methyl esters with small excess of methanol
WO2003042343A1 (fr) *	2001-11-16	2003-05-22	Gapes Richard J	Esterification d'acides gras dans des huiles
KR100556337B1 (ko) *	2002-02-05	2006-03-03	주식회사 가야에너지	단일단계 연속공정을 통한 고순도 지방산 알킬에스테르의제조방법
WO2003087279A2 (fr) *	2002-04-12	2003-10-23	Cornell Research Foundation, Inc.	Procede de transesterification continue
BR0313748A (pt) *	2002-08-23	2005-06-21	Richard Gapes	Transesterificação e esterificação de ácidos graxos e triglicerìdeos por dispersão, processo de dispersão para a fabricação de ésteres metìlicos de ácidos graxos
US7806945B2 (en) *	2003-01-27	2010-10-05	Seneca Landlord, Llc	Production of biodiesel and glycerin from high free fatty acid feedstocks
US7871448B2 (en) *	2003-01-27	2011-01-18	Seneca Landlord, Llc	Production of biodiesel and glycerin from high free fatty acid feedstocks
US9725397B2 (en)	2003-01-27	2017-08-08	REG Seneca, LLC	Production of biodiesel and glycerin from high free fatty acid feedstocks
US8088183B2 (en) *	2003-01-27	2012-01-03	Seneca Landlord, Llc	Production of biodiesel and glycerin from high free fatty acid feedstocks
AU2003282270B2 (en) *	2003-11-24	2009-08-27	Council Of Scientific And Industrial Research	An improved process for the preparation of bio-diesel
US20050108927A1 (en) *	2003-11-24	2005-05-26	Council Of Scientific And Industrial Research Of Rafi Marg	Process for the preparation of bio-diesel
JP2005206770A (ja) *	2004-01-19	2005-08-04	Ics Kk	脂肪酸エステルの製造方法及び脂肪酸エステルを含む燃料
JP4849387B2 (ja) *	2004-07-12	2012-01-11	アイシーエス株式会社	油脂類を原料とする脂肪酸エステルの製造方法
DE102004044660A1 (de)	2004-09-15	2006-03-30	Siegfried Prof. Dr. Peter	Verfahren zur Umesterung von Fetten und Ölen biologischen Ursprungs mittels Alkoholyse unter Verwendung spezieller Kohlensäuresalze
US7473539B2 (en) *	2004-09-20	2009-01-06	Sunho Biodiesel Corporation	Methods for producing alkyl esters
JP2006249066A (ja) *	2005-02-14	2006-09-21	Ics Kk	気液反応効率の向上方法
JP4963011B2 (ja) *	2005-03-01	2012-06-27	花王株式会社	脂肪酸低級アルキルエステルの製造方法
WO2006121021A1 (fr) *	2005-05-13	2006-11-16	Toray Industries, Inc.	Procédé servant à produire un ester d'acide gras et procédé servant à produire du glycérol
AT502218B1 (de) *	2005-07-25	2010-09-15	Bdi Biodiesel Internat Ag	Verfahren zur herstellung von carbonsäurealkylestern
CN100439474C (zh) *	2005-09-30	2008-12-03	中国科学院山西煤炭化学研究所	高酸值油脂同时酯化酯交换制备生物柴油的方法
US7624878B2 (en) *	2006-02-16	2009-12-01	Nalco Company	Fatty acid by-products and methods of using same
US20070218183A1 (en) *	2006-03-14	2007-09-20	Bunge Oils, Inc.	Oil composition of conjugated linoleic acid
JP2008031400A (ja) *	2006-06-29	2008-02-14	Ics Kk	油脂類を原料とする脂肪酸エステルの製造方法
WO2008071040A1 (fr) *	2006-12-15	2008-06-19	China Petroleum & Chemical Corporation	Procédé de préparation de biodiesel
US8500828B2 (en) *	2006-12-15	2013-08-06	China Petroleum & Chemical Corporation	Process for preparing a bio-diesel
US20080282606A1 (en) *	2007-04-16	2008-11-20	Plaza John P	System and process for producing biodiesel
WO2010098697A1 (fr) *	2009-02-24	2010-09-02	Закрытое Акционерное Общество Научно-Исследовательский Институт "Pocбиo"	Procédé pour produire du carburant biodiesel
US8907113B2 (en) *	2009-07-25	2014-12-09	Aicardo Roa-Espinosa	Enhanced biodiesel process
US20110021807A1 (en) *	2009-07-25	2011-01-27	Soil Net Llc	Enhanced biodiesel process
WO2014190436A1 (fr) *	2013-05-29	2014-12-04	Polyvalor Limited Partnership	Procédé et système de production d'un ester d'alkyle d'acide gras
US9957464B2 (en)	2013-06-11	2018-05-01	Renewable Energy Group, Inc.	Methods and devices for producing biodiesel and products obtained therefrom
US9328054B1 (en)	2013-09-27	2016-05-03	Travis Danner	Method of alcoholisis of fatty acids and fatty acid gyicerides
US9476009B2 (en) *	2015-03-05	2016-10-25	Drexel University	Acidic methanol stripping process that reduces sulfur content of biodiesel from waste greases
KR102062333B1 (ko)	2016-06-02	2020-01-03	유성민	지방산 메틸 또는 에틸 에스테르를 제조하기 위한 고체 촉매 및 이를 이용한 지방산 메틸 또는 에틸 에스테르 제조방법
FR3077299B1 (fr) *	2018-02-01	2020-10-30	Tropical Essence Sdn Bhd	Additif pour huile a base de triglycerides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2177407A (en) *	1936-09-21	1939-10-24	Du Pont	Alcoholysis of glycerides
US2383632A (en) *	1942-10-17	1945-08-28	Colgate Palmolive Peet Co	Process of treating fatty glycerides
US2383614A (en) *	1942-10-17	1945-08-28	Colgate Palmolive Peet Co	Treatment of fatty glycerides
US2378007A (en) *	1942-10-30	1945-06-12	Procter & Gamble	Process of modifying the molecular structure of oils and fats
US2447186A (en) *	1945-01-01	1948-08-17	Photo Technical Corp	Producing lower alkyl esters
GB634411A (en) *	1946-07-16	1950-03-22	Unilever Ltd	Method of treating low-grade fatty stock to form alkyl esters therefrom
US2494366A (en) *	1947-07-15	1950-01-10	Nopco Chem Co	Production of fatty esters

1984
- 1984-06-07 DE DE19843421217 patent/DE3421217A1/de not_active Withdrawn
1985
- 1985-05-29 AT AT85106561T patent/ATE46532T1/de not_active IP Right Cessation
- 1985-05-29 DE DE8585106561T patent/DE3573131D1/de not_active Expired
- 1985-05-29 EP EP85106561A patent/EP0164643B1/fr not_active Expired
- 1985-06-04 SU SU853901006A patent/SU1402250A3/ru active
- 1985-06-05 ES ES543917A patent/ES8604094A1/es not_active Expired
- 1985-06-05 KR KR1019850003920A patent/KR910008370B1/ko not_active Expired
- 1985-06-05 PT PT80603A patent/PT80603B/pt not_active IP Right Cessation
- 1985-06-05 US US06/741,639 patent/US4668439A/en not_active Expired - Fee Related
- 1985-06-05 NZ NZ212308A patent/NZ212308A/en unknown
- 1985-06-05 DD DD85277054A patent/DD232913A5/de not_active IP Right Cessation
- 1985-06-05 PH PH32367A patent/PH21080A/en unknown
- 1985-06-05 BR BR8502693A patent/BR8502693A/pt unknown
- 1985-06-06 MX MX205565A patent/MX160996A/es unknown
- 1985-06-06 AU AU43392/85A patent/AU569570B2/en not_active Ceased
- 1985-06-06 NO NO852293A patent/NO852293L/no unknown
- 1985-06-06 ZA ZA854288A patent/ZA854288B/xx unknown
- 1985-06-06 DK DK254685A patent/DK254685A/da not_active Application Discontinuation
- 1985-06-06 CA CA000483296A patent/CA1247130A/fr not_active Expired
- 1985-06-06 JP JP60121624A patent/JPS611640A/ja active Pending
- 1985-08-20 CN CN198585106282A patent/CN85106282A/zh active Pending
1987
- 1987-09-22 MY MYPI87001853A patent/MY100687A/en unknown

Also Published As

Publication number	Publication date
EP0164643A2 (fr)	1985-12-18
PT80603B (de)	1987-04-23
ATE46532T1 (de)	1989-10-15
BR8502693A (pt)	1986-02-12
KR860000238A (ko)	1986-01-27
US4668439A (en)	1987-05-26
ZA854288B (en)	1986-01-29
PH21080A (en)	1987-07-10
AU569570B2 (en)	1988-02-04
EP0164643B1 (fr)	1989-09-20
JPS611640A (ja)	1986-01-07
KR910008370B1 (ko)	1991-10-12
ES543917A0 (es)	1986-01-16
EP0164643A3 (en)	1987-01-28
CN85106282A (zh)	1987-02-18
PT80603A (de)	1985-07-01
DK254685D0 (da)	1985-06-06
ES8604094A1 (es)	1986-01-16
MY100687A (en)	1991-01-17
DK254685A (da)	1985-12-08
NO852293L (no)	1985-12-09
DE3573131D1 (en)	1989-10-26
DE3421217A1 (de)	1985-09-05
SU1402250A3 (ru)	1988-06-07
CA1247130A (fr)	1988-12-20
AU4339285A (en)	1985-12-12
NZ212308A (en)	1988-05-30
MX160996A (es)	1990-06-29

Legal Events

Date	Code	Title	Description
1994-11-24	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD232913A5 (de)	1986-02-12	Verfahren zur herstellung von fettsaeureestern kurzkettige alkohole
EP0198243B1 (fr)	1988-11-17	Procédé de préparation d'esters alkyliques d'acides carboxyliques en particulier d'esters alkyliques d'acides gras
DE60108184T2 (de)	2006-01-05	Verfahren zur Herstellung von Fettsäureestern
EP1141183B1 (fr)	2004-05-26	Procede de transesterification de corps gras et/ou d'huile d'origine biologique par alcoolyse
DE69808029T2 (de)	2003-02-06	Verfahren zum Herstellen von Fettsäureester
DE4335781C2 (de)	1998-02-19	Fettalkohole auf pflanzlicher Basis und Verfahren zu Ihrer Herstellung
EP0200982B1 (fr)	1989-01-11	Procédé d'interestérification catalytique de glycérides d'acides gras avec des alcanols inférieurs
EP2431352A2 (fr)	2012-03-21	Systèmes de catalyseurs pour la fabrication de biodiesel
EP2548937A1 (fr)	2013-01-23	Glycérates métalliques alcalino-terreux ou alcalins destinés à la désacidification et au séchage d'esters d'acides gras
EP1910267B1 (fr)	2012-01-11	Procede de production d'alkylesters d'acide carboxylique
DE69604545T2 (de)	2000-04-13	Direkte Veresterung von propoxyliertem Glycerin
EP0000916B1 (fr)	1981-05-20	Procédé de production de nitriles d'acides gras et de glycérine à partir de glycérides, en particulier de graisses et/ou huiles naturelles.
EP1319057B1 (fr)	2005-11-23	Procede de fabrication de produits bruts pour l'obtention d'acide linoleique conjugue
EP0273173B1 (fr)	1991-07-03	Procédé pour la préparation de nitriles d'acides gras et de glycérine à partir de glycérides
DE1206881B (de)	1965-12-16	Verfahren zur Herstellung von Fettsaeureglycerid-gemischen mit hohem Monoglyceridgehalt
EP2346972B1 (fr)	2013-01-02	Procede de production d'esters d'acides gras d'alcools monovalents ou plurivalents en utilisant des composes d'ammonium quaternaire speciaux a fonction hydroxy comme catalyseurs
DE69819208T2 (de)	2004-08-12	Auf der glycerolyse von methylester beruhendes verfahren zur herstellung von monoglycerid
WO1995013343A1 (fr)	1995-05-18	Procede de fabrication d'alkylesters inferieurs d'acides gras
EP0055797A1 (fr)	1982-07-14	Procédé de préparation d'acides acétiques substitués et/ou de leurs esters et d'acéto-nitriles substitués respectivement
WO2010037772A1 (fr)	2010-04-08	Procédé de fabrication d'un biodiesel
DE19724018A1 (de)	1998-12-10	Verfahren und Vorrichtung zur Herstellung von Glyzerin-Monofettsäuren
EP0298326B1 (fr)	1992-12-16	Procédé de production de 1-(alcylaminoalkyl)-2-imidazolines substituées en position 2
EP0891963B1 (fr)	2002-10-16	Procédé de préparation d'acides gras
DE3244752A1 (de)	1984-06-07	Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen
WO1989008106A1 (fr)	1989-09-08	Procede pour produire des 1-(acylaminoalkyl)-2-imidazolines substitues en position 2