CH508607A - Verfahren zur Herstellung von schwefelhaltigen Amiden - Google Patents

Verfahren zur Herstellung von schwefelhaltigen Amiden

Info

Publication number: CH508607A
Authority: CH; Switzerland
Prior art keywords: sep; fatty acid; acid; oil; oil fatty
Prior art date: 1966-08-12

Application number

CH1139467A

Other languages

German (de)

English (en)

Inventor

Fukumaru Toshitsugu

Hamma Noritaka

Nakatani Hiroshi

Fukushima Hideaki

Toki Katsuyuki

Original Assignee

Sumitomo Chemical Co

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.)

1966-08-12

Filing date

1967-08-14

Publication date

1971-06-15

1967-08-14 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1971-06-15 Publication of CH508607A publication Critical patent/CH508607A/de

Links

238000000034 method Methods 0.000 title claims description 29
150000001408 amides Chemical class 0.000 title claims description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 4
229910052717 sulfur Inorganic materials 0.000 title claims description 4
239000011593 sulfur Substances 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 3
150000004665 fatty acids Chemical class 0.000 claims description 169
239000000194 fatty acid Substances 0.000 claims description 167
235000014113 dietary fatty acids Nutrition 0.000 claims description 166
229930195729 fatty acid Natural products 0.000 claims description 166
150000001412 amines Chemical class 0.000 claims description 45
239000002904 solvent Substances 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 12
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 11
-1 fatty acid halide Chemical class 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000005456 glyceride group Chemical group 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
150000008065 acid anhydrides Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
125000005907 alkyl ester group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
235000021588 free fatty acids Nutrition 0.000 claims 1
239000003921 oil Substances 0.000 description 103
235000019198 oils Nutrition 0.000 description 103
239000002253 acid Substances 0.000 description 49
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 27
235000020778 linoleic acid Nutrition 0.000 description 27
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 22
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 20
239000000047 product Substances 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
241001125048 Sardina Species 0.000 description 12
241000269821 Scombridae Species 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
235000020640 mackerel Nutrition 0.000 description 12
235000019512 sardine Nutrition 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
235000019485 Safflower oil Nutrition 0.000 description 9
239000003925 fat Substances 0.000 description 9
235000019197 fats Nutrition 0.000 description 9
235000005713 safflower oil Nutrition 0.000 description 9
239000003813 safflower oil Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 8
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000002844 melting Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000008096 xylene Substances 0.000 description 8
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
YKFROQCFVXOUPW-UHFFFAOYSA-N 4-(methylthio) aniline Chemical compound CSC1=CC=C(N)C=C1 YKFROQCFVXOUPW-UHFFFAOYSA-N 0.000 description 7
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
201000001320 Atherosclerosis Diseases 0.000 description 7
239000005642 Oleic acid Substances 0.000 description 7
235000019484 Rapeseed oil Nutrition 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000004702 methyl esters Chemical class 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical class CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 6
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 6
235000020661 alpha-linolenic acid Nutrition 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 6
235000012000 cholesterol Nutrition 0.000 description 6
235000005687 corn oil Nutrition 0.000 description 6
239000002285 corn oil Substances 0.000 description 6
229960004488 linolenic acid Drugs 0.000 description 6
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 6
235000021388 linseed oil Nutrition 0.000 description 6
239000000944 linseed oil Substances 0.000 description 6
KDQIFKKWPMBNOH-UHFFFAOYSA-N methyl 16-methylheptadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCC(C)C KDQIFKKWPMBNOH-UHFFFAOYSA-N 0.000 description 6
235000011803 sesame oil Nutrition 0.000 description 6
239000008159 sesame oil Substances 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
241000269978 Pleuronectiformes Species 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
239000003529 anticholesteremic agent Substances 0.000 description 5
229940127226 anticholesterol agent Drugs 0.000 description 5
239000004202 carbamide Substances 0.000 description 5
150000001718 carbodiimides Chemical class 0.000 description 5
239000004359 castor oil Substances 0.000 description 5
235000019438 castor oil Nutrition 0.000 description 5
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 5
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 5
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 5
210000004185 liver Anatomy 0.000 description 5
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
229910052753 mercury Inorganic materials 0.000 description 5
239000004006 olive oil Substances 0.000 description 5
235000008390 olive oil Nutrition 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
235000011118 potassium hydroxide Nutrition 0.000 description 5
235000012424 soybean oil Nutrition 0.000 description 5
239000003549 soybean oil Substances 0.000 description 5
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
235000019774 Rice Bran oil Nutrition 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
239000004327 boric acid Substances 0.000 description 4
239000012295 chemical reaction liquid Substances 0.000 description 4
235000021323 fish oil Nutrition 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000008165 rice bran oil Substances 0.000 description 4
235000021122 unsaturated fatty acids Nutrition 0.000 description 4
150000004670 unsaturated fatty acids Chemical class 0.000 description 4
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 3
239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 3
WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 3
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 3
241001502129 Mullus Species 0.000 description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
235000019486 Sunflower oil Nutrition 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
238000001816 cooling Methods 0.000 description 3
235000012343 cottonseed oil Nutrition 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
239000002600 sunflower oil Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 2
YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
FBWMYSQUTZRHAT-HZJYTTRNSA-N (9z,12z)-octadeca-9,12-dienoyl chloride Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O FBWMYSQUTZRHAT-HZJYTTRNSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
241000251468 Actinopterygii Species 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
241000283153 Cetacea Species 0.000 description 2
241000252203 Clupea harengus Species 0.000 description 2
244000020551 Helianthus annuus Species 0.000 description 2
235000003222 Helianthus annuus Nutrition 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
235000004443 Ricinus communis Nutrition 0.000 description 2
206010070863 Toxicity to various agents Diseases 0.000 description 2
241001504592 Trachurus trachurus Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
230000000879 anti-atherosclerotic effect Effects 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
230000008021 deposition Effects 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000019688 fish Nutrition 0.000 description 2
235000019514 herring Nutrition 0.000 description 2
XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-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
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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239000000312 peanut oil Substances 0.000 description 2
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QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
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CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000001953 recrystallisation Methods 0.000 description 1
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WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
229960003656 ricinoleic acid Drugs 0.000 description 1
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
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239000008117 stearic acid Substances 0.000 description 1
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239000003760 tallow Substances 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
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239000010508 watermelon seed oil Substances 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)

CH1139467A 1966-08-12 1967-08-14 Verfahren zur Herstellung von schwefelhaltigen Amiden CH508607A (de)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP5317066		1966-08-12
JP67467		1966-12-27
JP67567		1966-12-27
JP56867		1966-12-28
JP4355267		1967-07-05
JP4355167		1967-07-05

Publications (1)

Publication Number	Publication Date
CH508607A true CH508607A (de)	1971-06-15

Family

ID=27547536

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1139467A CH508607A (de)	1966-08-12	1967-08-14	Verfahren zur Herstellung von schwefelhaltigen Amiden

Country Status (8)

Country	Link
US (1)	US3576830A (fr)
BE (1)	BE702623A (fr)
CH (1)	CH508607A (fr)
DE (1)	DE1618935A1 (fr)
FI (1)	FI47882C (fr)
FR (2)	FR7586M (fr)
GB (1)	GB1201631A (fr)
NL (1)	NL6711100A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1268082A (en) *	1969-08-08	1972-03-22	Orsymonde	Improvements in or relating to bis-(carboxy-alkylene-thio)-decanes
DE3064904D1 (en)	1979-06-13	1983-10-27	Nat Res Dev	A process for electrochemical additions to alkenes
JP2894445B2 (ja) *	1997-02-12	1999-05-24	日本たばこ産業株式会社	Ｃｅｔｐ活性阻害剤として有効な化合物
ES2277142T3 (es) *	2002-08-30	2007-07-01	Japan Tobacco Inc.	Compuesto de dibencilamina y su uso medicinal.
PL1603553T3 (pl) *	2003-03-17	2012-04-30	Japan Tobacco Inc	Kompozycje farmaceutyczne inhibitorów CETP
CA2519458A1 (fr) *	2003-03-17	2004-09-30	Japan Tobacco Inc.	Procede pour accroitre la biodisponibilite orale de s- 2-( '1-(2-ethylbutyl)cyclohexyl!carbonyl!amino)phenyl!-2-methylpropanethioate
TWI494102B (zh) *	2003-05-02	2015-08-01	Japan Tobacco Inc	包含ｓ-〔２（〔〔１-（２-乙基丁基）環己基〕羰基〕胺基）苯基〕２-甲基丙烷硫酯及ｈｍｇ輔酶ａ還原酶抑制劑之組合
CN113466396B (zh) *	2021-06-23	2024-09-17	山东省产品质量检验研究院	一种皮肤接触材料中增塑剂迁移量的检测方法
WO2025024685A2 (fr) *	2023-07-27	2025-01-30	Thomas Jefferson University	Inhibiteurs d'interactions de cib1 et procédés d'utilisation

1967
- 1967-08-07 US US658634A patent/US3576830A/en not_active Expired - Lifetime
- 1967-08-11 NL NL6711100A patent/NL6711100A/xx unknown
- 1967-08-11 BE BE702623D patent/BE702623A/xx unknown
- 1967-08-11 FI FI672170A patent/FI47882C/fi active
- 1967-08-11 DE DE19671618935 patent/DE1618935A1/de active Pending
- 1967-08-11 FR FR117771A patent/FR7586M/fr not_active Expired
- 1967-08-14 CH CH1139467A patent/CH508607A/de not_active IP Right Cessation
- 1967-08-14 GB GB37270/67A patent/GB1201631A/en not_active Expired
- 1967-10-04 FR FR1565354D patent/FR1565354A/fr not_active Expired

Also Published As

Publication number	Publication date
NL6711100A (fr)	1968-02-13
FR1565354A (fr)	1969-05-02
FI47882B (fr)	1974-01-02
BE702623A (fr)	1968-02-12
GB1201631A (en)	1970-08-12
FR7586M (fr)	1970-01-12
FI47882C (fi)	1974-04-10
DE1618935A1 (de)	1971-09-16
US3576830A (en)	1971-04-27

Legal Events

Date	Code	Title	Description
1978-03-15	PL	Patent ceased

Publication	Publication Date	Title
DE2228012C3 (de)	1980-01-17	Phthalidester der 6- [D(-)- a Aminophenylacetamido] -penicillansäure und Verfahren zu seiner Herstellung
DE2219710A1 (de)	1972-11-09	Biologisch aktive Verbindungen und Verfahren zu ihrer Herstellung
DE2426304C2 (fr)	1988-03-17
DE2549783A1 (de)	1976-05-20	Triglyceride mit entzuendungshemmender wirkung
CH508607A (de)	1971-06-15	Verfahren zur Herstellung von schwefelhaltigen Amiden
DE1493049B1 (de)	1971-09-30	N-substituierte Amide natuerlicher Fettsaeuregemische und Verfahren zu ihrer Herstellung
DE2446100C3 (de)	1982-01-14	Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel
DE1932389B2 (de)	1974-03-07	Neue 2-Naphthyl-2-methyläthanole und deren Acetate, sie enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE3013502C2 (de)	1985-02-07	[2''-(Trifluormethyl)-phenthiazin-10''-yl-(n-prop-3'''ylpiperazin-4''''-yläth-2'''''-yl)]-ester, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
DE2137538C3 (de)	1980-10-02	oxyamin und seine Salze sowie ein Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
DE2238304C3 (de)	1981-06-19	(Choleretisch wirksame) Ester bzw. Salze von Dehydrocholsäure, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
DE3312425A1 (de)	1984-10-11	Stoffmischungen mit wachstumsfoerdernder und leistungssteigernder wirkung sowie futtermittel und traenkfluessigkeiten, die geringe mengen dieser stoffmischungen enthalten
DE2152743A1 (de)	1972-04-27	Neue Malonsaeurederivate und solche Derivate enthaltende Arzneipraeparate
DE1956844B2 (de)	1978-06-15	ß-(2,4>6-Trijod-3-amidinophenyl)propionsäuren, deren Herstellung und mindestens eine dieser Verbindungen enthaltende Röntgenkontrastmittel
AT244326B (de)	1965-12-27	Verfahren zur Herstellung von neuen Derivaten von α-Hydroxycarbonsäuren
AT203482B (de)	1959-05-25	Verfahren zur Darstellung von neuen N-Alkyl-p-toluolsulfonylaminoessigsäuren
DE1801312A1 (de)	1969-05-08	Verfahren zur Herstellung einer neuen Aryloxyalkansaeure und ihrer Salze
AT280263B (de)	1970-04-10	Verfahren zur herstellung von neuen furazanderivaten
AT371440B (de)	1983-06-27	Verfahren zur herstellung von neuen n-substituierten moranolinderivaten und ihrer saeureadditionssalze
DE1593644C3 (fr)	1974-03-14
DE1670539C3 (de)	1975-10-09	Diacylthiamine und Verfahren zu deren Herstellung
AT206878B (de)	1959-12-28	Verfahren zur Herstellung von neuen Aminothiocarbonsäureestern
AT254391B (de)	1967-05-26	Verfahren zur Herstellung neuer antibiotischer Substanzen der Cephalosporin C-Reihe
AT347456B (de)	1978-12-27	Verfahren zur herstellung von neuen 5-methyl-7- hydroxy-isoflavon-derivaten
DE2302671A1 (de)	1973-07-26	5-acylpyrrole, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln