DD262859A5 - Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden - Google Patents

Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden Download PDF

Info

Publication number: DD262859A5
Authority: DD; German Democratic Republic
Prior art keywords: fatty acid; reaction; nitrile; glyceride; glycerol
Prior art date: 1986-11-21

Application number

DD87309214A

Other languages

German (de)

English (en)

Inventor

Herbert Stuehler

Kurt Fischer

Original Assignee

��@��k��

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.)

1986-11-21

Filing date

1987-11-19

Publication date

1988-12-14

1987-11-19 Application filed by ��@��k�� filed Critical ��@��k��

1988-12-14 Publication of DD262859A5 publication Critical patent/DD262859A5/de

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PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 244
235000011187 glycerol Nutrition 0.000 title claims description 80
238000000034 method Methods 0.000 title claims description 40
238000004519 manufacturing process Methods 0.000 title claims description 4
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 246
229930195729 fatty acid Natural products 0.000 claims abstract description 246
239000000194 fatty acid Substances 0.000 claims abstract description 246
238000006243 chemical reaction Methods 0.000 claims abstract description 223
-1 fatty acid nitrile Chemical class 0.000 claims abstract description 157
150000004665 fatty acids Chemical class 0.000 claims abstract description 120
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 95
125000005456 glyceride group Chemical group 0.000 claims abstract description 77
229910021529 ammonia Inorganic materials 0.000 claims abstract description 48
239000003054 catalyst Substances 0.000 claims abstract description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
239000000203 mixture Substances 0.000 claims abstract description 22
238000004064 recycling Methods 0.000 claims description 13
238000009833 condensation Methods 0.000 claims description 8
230000005494 condensation Effects 0.000 claims description 8
239000012535 impurity Substances 0.000 abstract description 2
239000002253 acid Substances 0.000 description 30
150000007513 acids Chemical class 0.000 description 23
239000012071 phase Substances 0.000 description 21
125000004432 carbon atom Chemical group C* 0.000 description 18
239000003925 fat Substances 0.000 description 12
235000019197 fats Nutrition 0.000 description 12
238000001816 cooling Methods 0.000 description 11
230000035484 reaction time Effects 0.000 description 11
239000003760 tallow Substances 0.000 description 11
238000010438 heat treatment Methods 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
DWBGKZPDTNQNDA-UHFFFAOYSA-N dioctadecyltin Chemical compound CCCCCCCCCCCCCCCCCC[Sn]CCCCCCCCCCCCCCCCCC DWBGKZPDTNQNDA-UHFFFAOYSA-N 0.000 description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
150000005840 aryl radicals Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
239000011701 zinc Substances 0.000 description 5
125000004429 atom Chemical group 0.000 description 4
235000015278 beef Nutrition 0.000 description 4
229910052793 cadmium Inorganic materials 0.000 description 4
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
239000003921 oil Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000007858 starting material Substances 0.000 description 4
150000003626 triacylglycerols Chemical class 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 3
150000002763 monocarboxylic acids Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
235000019198 oils Nutrition 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
150000003871 sulfonates Chemical class 0.000 description 3
150000003460 sulfonic acids Chemical class 0.000 description 3
VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 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
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LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 2
QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-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
VLHZUYUOEGBBJB-UHFFFAOYSA-N 18-hydroxyoctadecanoic acid Chemical compound OCCCCCCCCCCCCCCCCCC(O)=O VLHZUYUOEGBBJB-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
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
235000019482 Palm oil Nutrition 0.000 description 2
235000019484 Rapeseed oil Nutrition 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
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
QKZIVVMOMKTVIK-UHFFFAOYSA-M anilinomethanesulfonate Chemical compound [O-]S(=O)(=O)CNC1=CC=CC=C1 QKZIVVMOMKTVIK-UHFFFAOYSA-M 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
235000005687 corn oil Nutrition 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
238000007872 degassing Methods 0.000 description 2
KUCPUSUXIGWHFB-UHFFFAOYSA-N diphenyltin Chemical compound C=1C=CC=CC=1[Sn]C1=CC=CC=C1 KUCPUSUXIGWHFB-UHFFFAOYSA-N 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
238000005485 electric heating Methods 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 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
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
CACRRXGTWZXOAU-UHFFFAOYSA-N octadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCS(O)(=O)=O CACRRXGTWZXOAU-UHFFFAOYSA-N 0.000 description 2
WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
239000002540 palm oil Substances 0.000 description 2
SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
235000015277 pork Nutrition 0.000 description 2
238000011403 purification operation Methods 0.000 description 2
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 2
229960003656 ricinoleic acid Drugs 0.000 description 2
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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
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239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
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ZKCRKOCVERWCLP-UHFFFAOYSA-N Hiragonic acid Natural products CC=CCCC=CCCC=CCCCCC(O)=O ZKCRKOCVERWCLP-UHFFFAOYSA-N 0.000 description 1
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239000005639 Lauric acid Substances 0.000 description 1
235000021353 Lignoceric acid Nutrition 0.000 description 1
CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
235000021319 Palmitoleic acid Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000005643 Pelargonic acid Substances 0.000 description 1
244000057114 Sapium sebiferum Species 0.000 description 1
235000005128 Sapium sebiferum Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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QXCVIZVUKCQXSO-UHFFFAOYSA-N [Cd].CC1=CC=CC=C1.CC1=CC=CC=C1 Chemical compound [Cd].CC1=CC=CC=C1.CC1=CC=CC=C1 QXCVIZVUKCQXSO-UHFFFAOYSA-N 0.000 description 1
DXLNBCPLBHSCSJ-UHFFFAOYSA-N [Co].C1=CC=C2C(S(=O)(=O)OCCCCCCCCCCCC)=CC=CC2=C1 Chemical compound [Co].C1=CC=C2C(S(=O)(=O)OCCCCCCCCCCCC)=CC=CC2=C1 DXLNBCPLBHSCSJ-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
YDZIJQXINJLRLL-UHFFFAOYSA-N alpha-hydroxydodecanoic acid Natural products CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 0.000 description 1
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 description 1
235000020661 alpha-linolenic acid Nutrition 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
235000021302 avocado oil Nutrition 0.000 description 1
239000008163 avocado oil Substances 0.000 description 1
229940116226 behenic acid Drugs 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
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LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
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JLZNJNVARIYBCH-UHFFFAOYSA-L cadmium(2+);octadecane-1-sulfonate Chemical compound [Cd+2].CCCCCCCCCCCCCCCCCCS([O-])(=O)=O.CCCCCCCCCCCCCCCCCCS([O-])(=O)=O JLZNJNVARIYBCH-UHFFFAOYSA-L 0.000 description 1
RHIQGSVZFDSWSL-UHFFFAOYSA-L cadmium(2+);phenylmethanesulfonate Chemical compound [Cd+2].[O-]S(=O)(=O)CC1=CC=CC=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 RHIQGSVZFDSWSL-UHFFFAOYSA-L 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
IJBFSOLHRKELLR-FPLPWBNLSA-N cis-5-dodecenoic acid Chemical compound CCCCCC\C=C/CCCC(O)=O IJBFSOLHRKELLR-FPLPWBNLSA-N 0.000 description 1
SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
LZBGWFBAPLLXOS-UHFFFAOYSA-L cobalt(2+);2-hydroxydodecane-1-sulfonate Chemical compound [Co+2].CCCCCCCCCCC(O)CS([O-])(=O)=O.CCCCCCCCCCC(O)CS([O-])(=O)=O LZBGWFBAPLLXOS-UHFFFAOYSA-L 0.000 description 1
PINMEGJYPRAZER-UHFFFAOYSA-L cobalt(2+);octane-1-sulfonate Chemical compound [Co+2].CCCCCCCCS([O-])(=O)=O.CCCCCCCCS([O-])(=O)=O PINMEGJYPRAZER-UHFFFAOYSA-L 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000003026 cod liver oil Substances 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
230000008021 deposition Effects 0.000 description 1
WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
RPXYMVMDOAUFGX-UHFFFAOYSA-N dodecyl benzenesulfonate;zinc Chemical compound [Zn].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 RPXYMVMDOAUFGX-UHFFFAOYSA-N 0.000 description 1
DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
150000002196 fatty nitriles Chemical class 0.000 description 1
229940013317 fish oils Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008169 grapeseed oil Substances 0.000 description 1
239000010460 hemp oil Substances 0.000 description 1
SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 description 1
VXKNHLZRGIPBCN-UHFFFAOYSA-N hexyl benzenesulfonate iron Chemical compound [Fe].CCCCCCOS(=O)(=O)C1=CC=CC=C1 VXKNHLZRGIPBCN-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
229960004488 linolenic acid Drugs 0.000 description 1
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 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
235000013310 margarine Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
229940074096 monoolein Drugs 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-M o-toluate Chemical compound CC1=CC=CC=C1C([O-])=O ZWLPBLYKEWSWPD-UHFFFAOYSA-M 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000010491 poppyseed oil Substances 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000008171 pumpkin seed oil Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 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
229910052718 tin Inorganic materials 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
BHAROVLESINHSM-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1 BHAROVLESINHSM-UHFFFAOYSA-N 0.000 description 1
DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 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
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
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000010497 wheat germ oil Substances 0.000 description 1
YQLFJUAFJLSPPF-CVBJKYQLSA-L zinc (Z)-docos-13-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCCCCCC([O-])=O YQLFJUAFJLSPPF-CVBJKYQLSA-L 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
NMOHFBPSMIYLGY-UHFFFAOYSA-L zinc;2-dodecylbenzenesulfonate Chemical compound [Zn+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O NMOHFBPSMIYLGY-UHFFFAOYSA-L 0.000 description 1
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
- C07C31/225—Glycerol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD87309214A 1986-11-21 1987-11-19 Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden DD262859A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863639857 DE3639857A1 (de)	1986-11-21	1986-11-21	Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden

Publications (1)

Publication Number	Publication Date
DD262859A5 true DD262859A5 (de)	1988-12-14

Family

ID=6314491

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87309214A DD262859A5 (de)	1986-11-21	1987-11-19	Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden

Country Status (18)

Country	Link
US (1)	US4801730A (pt)
EP (1)	EP0273173B1 (pt)
JP (1)	JPS63150235A (pt)
CN (1)	CN1014605B (pt)
AU (1)	AU598881B2 (pt)
BR (1)	BR8706262A (pt)
CA (1)	CA1305182C (pt)
DD (1)	DD262859A5 (pt)
DE (2)	DE3639857A1 (pt)
DK (1)	DK610687A (pt)
ES (1)	ES2023396B3 (pt)
IE (1)	IE873145L (pt)
IL (1)	IL84547A (pt)
NO (1)	NO165394C (pt)
PH (1)	PH25220A (pt)
PT (1)	PT86163B (pt)
SU (1)	SU1551243A3 (pt)
ZA (1)	ZA878694B (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001058913A1 (en) *	2000-02-08	2001-08-16	Exxonmobil Chemical Patents Inc.	Method of preparing group 14 bridged biscyclopentadienyl ligands
JP4972387B2 (ja) *	2006-03-08	2012-07-11	花王株式会社	脂肪族ニトリルの製造方法
FR2907781B1 (fr) *	2006-10-27	2010-01-08	Ceca Sa	Procede de synthese de diamines et/ou de triamines primaires de haute purete a partir d'acides dimeres ou trimeres
FR2916445B1 (fr) *	2007-05-24	2009-07-10	Arkema France	Procede de co-production de carbonates cycliques et de nitriles et/ou d'amines gras
GT200700043A (es) *	2007-05-25	2008-03-03		Biocompuestos de funcion nitrilo
FR2979342B1 (fr)	2011-08-26	2013-08-09	Arkema France	Procede de synthese d'esters d'acides omega-amino-alcanoiques en c11 et c12 comportant une etape de metathese
FR3002227B1 (fr)	2013-02-20	2021-10-01	Arkema France	Procede de nitrilation en phase gaz et liquide gaz

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3979432A (en) *	1974-06-21	1976-09-07	Eastman Kodak Company	Preparation of nitriles
ES472553A1 (es) *	1977-08-20	1979-02-16	Hoechst Ag	Procedimiento para la preparacion de nitrilos de acidos gra-sos de la formula r1(r2, r3)-cn y de glicerina
DE3131968A1 (de) *	1981-08-13	1983-02-24	Chemische Werke Hüls AG, 4370 Marl	Verfahren zur herstellung von aliphatischen nitrilen
DE3244752A1 (de) *	1982-12-03	1984-06-07	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen

1986
- 1986-11-21 DE DE19863639857 patent/DE3639857A1/de not_active Withdrawn
1987
- 1987-11-17 EP EP87116921A patent/EP0273173B1/de not_active Expired - Lifetime
- 1987-11-17 ES ES87116921T patent/ES2023396B3/es not_active Expired - Lifetime
- 1987-11-17 DE DE8787116921T patent/DE3771191D1/de not_active Expired - Fee Related
- 1987-11-19 DD DD87309214A patent/DD262859A5/de not_active IP Right Cessation
- 1987-11-19 PH PH36084A patent/PH25220A/en unknown
- 1987-11-19 US US07/122,403 patent/US4801730A/en not_active Expired - Fee Related
- 1987-11-19 PT PT86163A patent/PT86163B/pt not_active IP Right Cessation
- 1987-11-20 IL IL84547A patent/IL84547A/xx unknown
- 1987-11-20 AU AU81449/87A patent/AU598881B2/en not_active Ceased
- 1987-11-20 JP JP62292242A patent/JPS63150235A/ja active Pending
- 1987-11-20 CA CA000552315A patent/CA1305182C/en not_active Expired - Fee Related
- 1987-11-20 SU SU874203696A patent/SU1551243A3/ru active
- 1987-11-20 CN CN87107926A patent/CN1014605B/zh not_active Expired
- 1987-11-20 DK DK610687A patent/DK610687A/da not_active Application Discontinuation
- 1987-11-20 BR BR8706262A patent/BR8706262A/pt unknown
- 1987-11-20 ZA ZA878694A patent/ZA878694B/xx unknown
- 1987-11-20 NO NO874853A patent/NO165394C/no unknown
- 1987-11-20 IE IE873145A patent/IE873145L/xx unknown

Also Published As

Publication number	Publication date
IL84547A (en)	1992-02-16
IL84547A0 (en)	1988-04-29
DK610687A (da)	1988-05-22
JPS63150235A (ja)	1988-06-22
DK610687D0 (da)	1987-11-20
IE873145L (en)	1988-05-21
ZA878694B (en)	1988-08-31
CN87107926A (zh)	1988-06-01
SU1551243A3 (ru)	1990-03-15
EP0273173B1 (de)	1991-07-03
EP0273173A2 (de)	1988-07-06
NO874853D0 (no)	1987-11-20
BR8706262A (pt)	1988-06-28
CA1305182C (en)	1992-07-14
EP0273173A3 (en)	1988-07-20
AU8144987A (en)	1988-05-26
PH25220A (en)	1991-03-27
CN1014605B (zh)	1991-11-06
PT86163A (de)	1987-12-01
NO165394B (no)	1990-10-29
PT86163B (pt)	1990-11-20
AU598881B2 (en)	1990-07-05
NO165394C (no)	1991-02-06
DE3771191D1 (de)	1991-08-08
DE3639857A1 (de)	1988-06-01
US4801730A (en)	1989-01-31
NO874853L (no)	1988-05-24
ES2023396B3 (es)	1992-01-16

Legal Events

Date	Code	Title	Description
1995-10-12	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE60108184T2 (de)	2006-01-05	Verfahren zur Herstellung von Fettsäureestern
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EP0198243B1 (de)	1988-11-17	Verfahren zur Herstellung von Carbonsäurealkylestern, insbesondere Fettsäurealkylestern
DE2946565C2 (pt)	1990-08-09
DE4335781C2 (de)	1998-02-19	Fettalkohole auf pflanzlicher Basis und Verfahren zu Ihrer Herstellung
EP1141183B1 (de)	2004-05-26	Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse
DE2552311C3 (de)	1981-09-17	Verfahren zur Herstellung von Öl- und Fettfraktionen durch Umestern
AT502218B1 (de)	2010-09-15	Verfahren zur herstellung von carbonsäurealkylestern
DE69811676T2 (de)	2003-11-13	Verfahren zur verminderung des gehaltes an langkettigen gesättigten fettsäuren in fettsäurezusammensetzungen
EP0273173B1 (de)	1991-07-03	Verfahren zur Herstellung von Fettsäurenitrilen und Glycerin aus Glyceriden
DE3727981A1 (de)	1988-03-03	Verfahren und vorrichtung zur herstellung eines als kraft- bzw. brennstoff geeigneten fettsaeureestergemisches
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