DE2127776A1 - Verfahren zur Herstellung cyclischer Imidsäureester - Google Patents
Verfahren zur Herstellung cyclischer ImidsäureesterInfo
- Publication number
- DE2127776A1 DE2127776A1 DE19712127776 DE2127776A DE2127776A1 DE 2127776 A1 DE2127776 A1 DE 2127776A1 DE 19712127776 DE19712127776 DE 19712127776 DE 2127776 A DE2127776 A DE 2127776A DE 2127776 A1 DE2127776 A1 DE 2127776A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- acetate
- radical
- zinc
- oxazoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 cyclic imidic acid esters Chemical class 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- 150000001414 amino alcohols Chemical class 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 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 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229940011182 cobalt acetate Drugs 0.000 claims description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- 229940071125 manganese acetate Drugs 0.000 claims description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 2
- 229940078494 nickel acetate Drugs 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 229940102001 zinc bromide Drugs 0.000 claims description 2
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229910052845 zircon Inorganic materials 0.000 claims 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 51
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 238000009835 boiling Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 8
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 7
- 238000004508 fractional distillation Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 3
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VXCUURYYWGCLIH-UHFFFAOYSA-N Dodecanenitrile Chemical compound CCCCCCCCCCCC#N VXCUURYYWGCLIH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VHSKSVCULAEZBU-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1,3-oxazole Chemical compound N1C=COC1C1=CC=CC=C1 VHSKSVCULAEZBU-UHFFFAOYSA-N 0.000 description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002463 imidates Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HBQUOLGAXBYZGR-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 HBQUOLGAXBYZGR-UHFFFAOYSA-N 0.000 description 1
- XUMZVELBFAWULJ-UHFFFAOYSA-N 2-[4-(5,6-dihydro-4h-1,3-oxazin-2-yl)phenyl]-5,6-dihydro-4h-1,3-oxazine Chemical compound C1CCOC(C=2C=CC(=CC=2)C=2OCCCN=2)=N1 XUMZVELBFAWULJ-UHFFFAOYSA-N 0.000 description 1
- KYHSOVKSTASUMY-UHFFFAOYSA-N 2-methyl-5,6-dihydro-4h-1,3-oxazine Chemical compound CC1=NCCCO1 KYHSOVKSTASUMY-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- GUXASSGFGULBAX-UHFFFAOYSA-N 2-phenyl-5,6-dihydro-4h-1,3-oxazine Chemical compound C1CCOC(C=2C=CC=CC=2)=N1 GUXASSGFGULBAX-UHFFFAOYSA-N 0.000 description 1
- WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentane carboxylic acid Natural products OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGXGAUQEMYSVJM-UHFFFAOYSA-N hexadecanenitrile Chemical compound CCCCCCCCCCCCCCCC#N WGXGAUQEMYSVJM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical class OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 description 1
- YJMNOKOLADGBKA-UHFFFAOYSA-N naphthalene-1-carbonitrile Chemical compound C1=CC=C2C(C#N)=CC=CC2=C1 YJMNOKOLADGBKA-UHFFFAOYSA-N 0.000 description 1
- AZKDTTQQTKDXLH-UHFFFAOYSA-N naphthalene-2-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- RHSBIGNQEIPSCT-UHFFFAOYSA-N stearonitrile Chemical compound CCCCCCCCCCCCCCCCCC#N RHSBIGNQEIPSCT-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712127776 DE2127776A1 (de) | 1971-06-04 | 1971-06-04 | Verfahren zur Herstellung cyclischer Imidsäureester |
| DE2158061A DE2158061A1 (de) | 1971-06-04 | 1971-11-24 | Verfahren zur herstellung cyclischer imidsaeureester |
| IT50644/72A IT958179B (it) | 1971-06-04 | 1972-05-31 | Procedimento per produrre esteri acidi di immidi cicliche |
| FR727219657A FR2141718B1 (enExample) | 1971-06-04 | 1972-06-01 | |
| US00259310A US3813378A (en) | 1971-06-04 | 1972-06-02 | Process for the production of cyclic imidic acid esters |
| GB2583572A GB1383106A (en) | 1971-06-04 | 1972-06-02 | Process for the manufacture of cyclic imide-acid esters |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712127776 DE2127776A1 (de) | 1971-06-04 | 1971-06-04 | Verfahren zur Herstellung cyclischer Imidsäureester |
| DE2158061A DE2158061A1 (de) | 1971-06-04 | 1971-11-24 | Verfahren zur herstellung cyclischer imidsaeureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2127776A1 true DE2127776A1 (de) | 1972-12-14 |
Family
ID=25761233
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712127776 Pending DE2127776A1 (de) | 1971-06-04 | 1971-06-04 | Verfahren zur Herstellung cyclischer Imidsäureester |
| DE2158061A Pending DE2158061A1 (de) | 1971-06-04 | 1971-11-24 | Verfahren zur herstellung cyclischer imidsaeureester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2158061A Pending DE2158061A1 (de) | 1971-06-04 | 1971-11-24 | Verfahren zur herstellung cyclischer imidsaeureester |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3813378A (enExample) |
| DE (2) | DE2127776A1 (enExample) |
| FR (1) | FR2141718B1 (enExample) |
| GB (1) | GB1383106A (enExample) |
| IT (1) | IT958179B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3127609A1 (de) * | 1981-07-13 | 1983-01-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von n-vinylamiden |
| DE3224880A1 (de) * | 1982-07-03 | 1984-01-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von reinen, wasserfreien imidsaeureestern durch umsetzung von nitrilen mit aminoalkoholen |
| EP0394850A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3-oxazinen |
| US8344167B2 (en) | 2007-07-10 | 2013-01-01 | Sumitomo Chemical Company, Limited | Method for producing propylene oxide |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2329545C2 (de) * | 1973-06-09 | 1986-06-12 | Bayer Ag, 5090 Leverkusen | 1,2-Bis-oxazolinyl-(2)-cyclobutane und Verfahren zu ihrer Herstellung |
| US4061854A (en) * | 1975-06-12 | 1977-12-06 | Shionogi & Co., Ltd. | Dihydroethanoanthracene derivatives useful as antidepressants |
| US4543414A (en) * | 1978-12-05 | 1985-09-24 | The Dow Chemical Company | Liquid phase preparation of 2-substituted-2-oxazolines with cadmium salt catalysts |
| US4354029A (en) * | 1981-11-30 | 1982-10-12 | The Dow Chemical Company | Preparation of 2-substituted-2-oxazolines with organic zinc salt catalysts |
| DE3310905A1 (de) * | 1983-03-25 | 1984-09-27 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von 2-isopropenyloxazolinen |
| GB2156344A (en) * | 1984-03-26 | 1985-10-09 | Dow Chemical Co | Liquid phase preparation of optionally 2-substituted-2-oxazolines by cyclodehydration |
| US5227494A (en) * | 1988-09-14 | 1993-07-13 | Schering Corporation | Process for preparing oxazoline compounds |
| CA2094810C (en) * | 1990-10-25 | 2002-06-04 | Jon E. Clark | Process for preparing florfenicol, its analogs and oxazoline intermediates thereto |
| US5773629A (en) * | 1996-06-14 | 1998-06-30 | Industrial Technology Research Institute | Synthesis of (4S, 5R) -2, 4-diphenyl-5-carboxy-oxazoline derivative as taxol side-chain precursor |
-
1971
- 1971-06-04 DE DE19712127776 patent/DE2127776A1/de active Pending
- 1971-11-24 DE DE2158061A patent/DE2158061A1/de active Pending
-
1972
- 1972-05-31 IT IT50644/72A patent/IT958179B/it active
- 1972-06-01 FR FR727219657A patent/FR2141718B1/fr not_active Expired
- 1972-06-02 US US00259310A patent/US3813378A/en not_active Expired - Lifetime
- 1972-06-02 GB GB2583572A patent/GB1383106A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3127609A1 (de) * | 1981-07-13 | 1983-01-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von n-vinylamiden |
| DE3224880A1 (de) * | 1982-07-03 | 1984-01-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von reinen, wasserfreien imidsaeureestern durch umsetzung von nitrilen mit aminoalkoholen |
| EP0098356A3 (en) * | 1982-07-03 | 1985-01-23 | Chemische Werke Huls Ag | Process for the preparation of pure anhydrous imido-acid esters by the reaction between nitriles and amino-alcohols |
| EP0394850A1 (de) * | 1989-04-28 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3-oxazinen |
| WO1990013547A1 (de) * | 1989-04-28 | 1990-11-15 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von 5,6-dihydro-4h-1,3-oxazinen |
| US8344167B2 (en) | 2007-07-10 | 2013-01-01 | Sumitomo Chemical Company, Limited | Method for producing propylene oxide |
Also Published As
| Publication number | Publication date |
|---|---|
| US3813378A (en) | 1974-05-28 |
| IT958179B (it) | 1973-10-20 |
| DE2158061A1 (de) | 1973-05-30 |
| FR2141718A1 (enExample) | 1973-01-26 |
| GB1383106A (en) | 1975-02-05 |
| FR2141718B1 (enExample) | 1973-07-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1593277B2 (de) | Verfahren zur herstellung von gemischen aliphatischer nitrile | |
| DE2807849A1 (de) | Verfahren zur wiedergewinnung von katalysatoren | |
| DE2127776A1 (de) | Verfahren zur Herstellung cyclischer Imidsäureester | |
| DE1817797C3 (de) | Verfahren zur Isomerisierung von 2-Methyl-3-butennitril zu 3-Pentennitril | |
| EP0419412B1 (de) | Verfahren zur Herstellung von Benztriazolen | |
| DE2155113A1 (enExample) | ||
| DE1129153B (de) | Verfahren zur Herstellung von ª-Cyan-ª-Alkyl-ª-phenylacrylsaeureestern | |
| EP0144885B1 (de) | Verfahren zur gleichzeitigen Herstellung von Nitrilen und Acrylamid bzw. Methacrylamid | |
| DE3390407T1 (de) | Gegen Auslaugen beständiger Katalysator für die Dimerisierung von Acrylverbindungen | |
| DE2047846C3 (de) | 4-Piperidonenoläther, Verfahren zu deren Herstellung und deren Verwendung zum Stabilisieren von synthetischen Polymeren | |
| DE60007148T2 (de) | Verfahren zur umsetzung von aldehyden zu nitrilen durch reaktion mit ammoniak and wasserstoff-peroxid | |
| DE69825745T2 (de) | Verfahren zur entfernung von schwermetallen | |
| DE2226588A1 (de) | Cyanoäthylierung von Aminophenolen | |
| EP0006140B1 (de) | Verfahren zur Herstellung von alpha-Hydroxycarbonsäureamiden | |
| DE1493965C (de) | Verfahren zum Herstellen von Racema ten optisch aktiver Nitrile | |
| DE1044795B (de) | Verfahren zur Herstellung von Carbonsaeureamiden durch Isomerisierung von Aldoximen | |
| AT220614B (de) | Verfahren zur Herstellung neuer substituierter Amine und ihrer Salze | |
| DE3343674A1 (de) | Verfahren zur herstellung von (alpha) -substituierten acrylsaeureamiden | |
| DE1074047B (de) | Verfahren zur Herstellung von Chinazolmen | |
| DE1493817C (de) | Verfahren zur Herstellung von aromatischen Aminoketonen | |
| EP0015385B1 (de) | Verfahren zur Herstellung von n-Propylcyanessigsäureestern und n-Äthylcyanessigsäureestern | |
| DE1198817B (de) | Verfahren zur Herstellung von Cycloalkyloxyalkylguanidinen | |
| AT208867B (de) | Verfahren zur Herstellung von neuen substituierten heterocyclischen Säurehydraziden | |
| AT204048B (de) | Verfahren zur Herstellung von neuen Phenazinderivaten | |
| DE1620493C (de) | Barbitursaurederivate und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |