SK282253B6 - Spôsob výroby aromatických alebo heteroaromatických hydroxylamínov - Google Patents
Spôsob výroby aromatických alebo heteroaromatických hydroxylamínov Download PDFInfo
- Publication number
- SK282253B6 SK282253B6 SK929-97A SK92997A SK282253B6 SK 282253 B6 SK282253 B6 SK 282253B6 SK 92997 A SK92997 A SK 92997A SK 282253 B6 SK282253 B6 SK 282253B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- process according
- hydrogen
- hydrogenation
- alkoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 34
- -1 heteroaromatic hydroxylamines Chemical class 0.000 title claims abstract description 24
- 230000008569 process Effects 0.000 title claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 150000002828 nitro derivatives Chemical class 0.000 claims abstract description 9
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- 150000003222 pyridines Chemical class 0.000 claims abstract description 4
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims abstract description 3
- 150000003248 quinolines Chemical class 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 10
- LMRKVKPRHROQRR-UHFFFAOYSA-N 4-butylmorpholine Chemical compound CCCCN1CCOCC1 LMRKVKPRHROQRR-UHFFFAOYSA-N 0.000 claims description 3
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- YNWIKPKXZZFVHT-UHFFFAOYSA-N 2,2,4,6,6-pentamethylmorpholine Chemical compound CN1CC(C)(C)OC(C)(C)C1 YNWIKPKXZZFVHT-UHFFFAOYSA-N 0.000 claims description 2
- QKVSMSABRNCNRS-UHFFFAOYSA-N 4-(2-methylpropyl)morpholine Chemical compound CC(C)CN1CCOCC1 QKVSMSABRNCNRS-UHFFFAOYSA-N 0.000 claims description 2
- IERWMZNDJGYCIA-UHFFFAOYSA-N 4-pentylmorpholine Chemical compound CCCCCN1CCOCC1 IERWMZNDJGYCIA-UHFFFAOYSA-N 0.000 claims description 2
- NMILGIZTAZXMTM-UHFFFAOYSA-N 4-propylmorpholine Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052711 selenium Inorganic materials 0.000 abstract description 3
- 239000011669 selenium Substances 0.000 abstract description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 18
- OMYXQGTUTCZGCI-UHFFFAOYSA-N n-(2-methylphenyl)hydroxylamine Chemical compound CC1=CC=CC=C1NO OMYXQGTUTCZGCI-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 5
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical class ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- IARNXGGKYDPYTB-UHFFFAOYSA-N n-(2,3-dichlorophenyl)hydroxylamine Chemical compound ONC1=CC=CC(Cl)=C1Cl IARNXGGKYDPYTB-UHFFFAOYSA-N 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 125000001477 organic nitrogen group Chemical group 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- UPKQTNZSDMAYNO-UHFFFAOYSA-N 1-benzyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CC1=CC=CC=C1 UPKQTNZSDMAYNO-UHFFFAOYSA-N 0.000 description 1
- GXPIVRKDWZKIKZ-UHFFFAOYSA-N 1-fluoro-2-methyl-3-nitrobenzene Chemical compound CC1=C(F)C=CC=C1[N+]([O-])=O GXPIVRKDWZKIKZ-UHFFFAOYSA-N 0.000 description 1
- WRFGMXWDQDQRKO-UHFFFAOYSA-N 2,3,4,5,6-pentamethylmorpholine Chemical compound CC1OC(C)C(C)N(C)C1C WRFGMXWDQDQRKO-UHFFFAOYSA-N 0.000 description 1
- APOJIILNJVLCQE-UHFFFAOYSA-N 2,4,6-trimethylmorpholine Chemical compound CC1CN(C)CC(C)O1 APOJIILNJVLCQE-UHFFFAOYSA-N 0.000 description 1
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 1
- IZNWACYOILBFEG-UHFFFAOYSA-N 2-methyl-1-nitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C(C)=CC=C21 IZNWACYOILBFEG-UHFFFAOYSA-N 0.000 description 1
- UHPGVDHXHDPYQP-UHFFFAOYSA-N 2-methyl-8-nitroquinoline Chemical compound C1=CC=C([N+]([O-])=O)C2=NC(C)=CC=C21 UHPGVDHXHDPYQP-UHFFFAOYSA-N 0.000 description 1
- XLZMWNWNBXSZKF-UHFFFAOYSA-N 4-propan-2-ylmorpholine Chemical compound CC(C)N1CCOCC1 XLZMWNWNBXSZKF-UHFFFAOYSA-N 0.000 description 1
- OILJIEKQCVHNMM-UHFFFAOYSA-N 4-tert-butylmorpholine Chemical compound CC(C)(C)N1CCOCC1 OILJIEKQCVHNMM-UHFFFAOYSA-N 0.000 description 1
- 238000006665 Bamberger reaction Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical class O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/10—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of unsubstituted hydrocarbon radicals or of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/12—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19502700A DE19502700A1 (de) | 1995-01-28 | 1995-01-28 | Verfahren zur Herstellung von N-Aryl- und N-Hetarylhydroxylaminen |
PCT/EP1996/000170 WO1996022967A1 (de) | 1995-01-28 | 1996-01-17 | Verfahren zur herstellung von n-aryl- und n-hetarylhydroxylaminen |
Publications (2)
Publication Number | Publication Date |
---|---|
SK92997A3 SK92997A3 (en) | 1998-05-06 |
SK282253B6 true SK282253B6 (sk) | 2001-12-03 |
Family
ID=7752554
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK929-97A SK282253B6 (sk) | 1995-01-28 | 1996-01-17 | Spôsob výroby aromatických alebo heteroaromatických hydroxylamínov |
Country Status (22)
Country | Link |
---|---|
US (1) | US5831093A (cs) |
EP (1) | EP0805797B1 (cs) |
JP (1) | JP3778567B2 (cs) |
KR (1) | KR100391870B1 (cs) |
CN (1) | CN1073553C (cs) |
AR (1) | AR000813A1 (cs) |
AT (1) | ATE178586T1 (cs) |
AU (1) | AU691390B2 (cs) |
BR (1) | BR9606855A (cs) |
CA (1) | CA2211390A1 (cs) |
CZ (1) | CZ289091B6 (cs) |
DE (2) | DE19502700A1 (cs) |
DK (1) | DK0805797T3 (cs) |
ES (1) | ES2129951T3 (cs) |
GR (1) | GR3029933T3 (cs) |
HU (1) | HU220590B1 (cs) |
IL (1) | IL116924A (cs) |
NZ (1) | NZ300198A (cs) |
SK (1) | SK282253B6 (cs) |
TW (1) | TW330928B (cs) |
WO (1) | WO1996022967A1 (cs) |
ZA (1) | ZA96610B (cs) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6362380B1 (en) * | 1996-03-13 | 2002-03-26 | Basf Aktiengesellschaft | Preparation of nitrobiphenyls |
DE19610571A1 (de) * | 1996-03-18 | 1997-09-25 | Basf Ag | Verfahren und Zwischenprodukte zur Herstellung von Pyridyl-4-Fluoranilinen |
HUP0004063A3 (en) | 1997-09-05 | 2002-11-28 | Basf Ag | Method for producing (hetero)aromatic hydroxylamines |
DE19738864A1 (de) * | 1997-09-05 | 1999-03-11 | Basf Ag | Verfahren zur Herstellung N-acylierter (hetero)aromatischer Hydroxylamine |
DE19753462A1 (de) * | 1997-12-02 | 1999-06-10 | Consortium Elektrochem Ind | Verfahren zur Herstellung organischer Hydroxylamine |
CN1331840C (zh) * | 2004-11-11 | 2007-08-15 | 中国科学院大连化学物理研究所 | 一种催化合成苯胲类化合物的方法 |
US8455690B2 (en) * | 2007-03-27 | 2013-06-04 | Wako Pure Chemical Industries, Ltd. | Method for producing arylhydroxylamine |
AR078156A1 (es) | 2009-09-04 | 2011-10-19 | Basf Se | Proceso para preparar 1-fenilpirazoles |
BR112012021749B1 (pt) | 2010-03-18 | 2018-12-26 | Basf Se | processos para a preparação de um composto e composto benzilamina |
BR112013006230C8 (pt) | 2010-09-21 | 2017-09-19 | Basf Se | processo para a preparação de uma n-fenilhidroxilamina substituída |
CN102430416B (zh) * | 2010-11-16 | 2013-11-06 | 江苏恒祥化工有限责任公司 | 一种用于1,8-二硝基萘催化加氢制备1,8-二氨基萘的催化剂及其制备方法 |
CN103415508B (zh) * | 2011-03-09 | 2016-08-10 | 巴斯夫欧洲公司 | 制备取代的n-苯基羟胺的方法 |
CN107673999A (zh) * | 2017-10-30 | 2018-02-09 | 青岛瀚生生物科技股份有限公司 | 制备吡唑醚菌酯中间体的方法 |
CN108636433B (zh) * | 2018-04-13 | 2021-02-02 | 山西大学 | 一种氮掺杂多孔碳固载的贵金属催化剂及其制备方法和应用 |
EP3587391A1 (en) | 2018-06-22 | 2020-01-01 | Basf Se | Process for preparing nitrobenzyl bromides |
CN109331818B (zh) * | 2018-08-25 | 2021-07-27 | 浙江工业大学 | 一种催化加氢催化剂及其制备和在芳香硝基化合物选择性加氢反应中的应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3393237A (en) * | 1965-09-22 | 1968-07-16 | Abbott Lab | Preparation of cyclohexylhydroxylamine |
FR2252337B1 (cs) * | 1973-11-26 | 1976-10-01 | Rhone Poulenc Ind | |
US5166435A (en) * | 1983-12-06 | 1992-11-24 | Akzo N.V. | Process for the preparation of a hydroxylamine |
DE3468102D1 (en) * | 1983-12-06 | 1988-01-28 | Akzo Nv | Process for the preparation of a hydroxylamine |
CA1340939C (en) * | 1987-02-02 | 2000-03-28 | Ryojiro Akashi | Photochromic compound |
ATE101852T1 (de) * | 1987-12-14 | 1994-03-15 | Grace W R & Co | Hydrierung von nitroalkanen zu hydroxylaminen. |
BE1007835A3 (nl) * | 1993-12-16 | 1995-10-31 | Dsm Nv | Werkwijze voor de bereiding van n-alkyl-n,o-diacetyl-hydroxylamine. |
US5646327A (en) * | 1995-12-08 | 1997-07-08 | Eastman Kodak Company | Method for preparing hydroxylamines using vinylic compounds without base neutralization and reaction mixture produced thereby |
-
1995
- 1995-01-28 DE DE19502700A patent/DE19502700A1/de not_active Withdrawn
-
1996
- 1996-01-17 DE DE59601604T patent/DE59601604D1/de not_active Expired - Lifetime
- 1996-01-17 NZ NZ300198A patent/NZ300198A/xx unknown
- 1996-01-17 KR KR1019970705112A patent/KR100391870B1/ko not_active Expired - Fee Related
- 1996-01-17 CA CA002211390A patent/CA2211390A1/en not_active Abandoned
- 1996-01-17 AT AT96900963T patent/ATE178586T1/de not_active IP Right Cessation
- 1996-01-17 JP JP52259396A patent/JP3778567B2/ja not_active Expired - Fee Related
- 1996-01-17 HU HU9801132A patent/HU220590B1/hu not_active IP Right Cessation
- 1996-01-17 CN CN96191626A patent/CN1073553C/zh not_active Expired - Lifetime
- 1996-01-17 CZ CZ19972270A patent/CZ289091B6/cs unknown
- 1996-01-17 AU AU44869/96A patent/AU691390B2/en not_active Ceased
- 1996-01-17 DK DK96900963T patent/DK0805797T3/da active
- 1996-01-17 ES ES96900963T patent/ES2129951T3/es not_active Expired - Lifetime
- 1996-01-17 SK SK929-97A patent/SK282253B6/sk unknown
- 1996-01-17 WO PCT/EP1996/000170 patent/WO1996022967A1/de active IP Right Grant
- 1996-01-17 US US08/860,671 patent/US5831093A/en not_active Expired - Lifetime
- 1996-01-17 BR BR9606855A patent/BR9606855A/pt not_active IP Right Cessation
- 1996-01-17 EP EP96900963A patent/EP0805797B1/de not_active Expired - Lifetime
- 1996-01-25 TW TW085100855A patent/TW330928B/zh active
- 1996-01-26 IL IL11692496A patent/IL116924A/xx not_active IP Right Cessation
- 1996-01-26 AR ARP960101168A patent/AR000813A1/es active IP Right Grant
- 1996-01-26 ZA ZA96610A patent/ZA96610B/xx unknown
-
1999
- 1999-04-08 GR GR990400975T patent/GR3029933T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
MX9705275A (es) | 1997-10-31 |
AR000813A1 (es) | 1997-08-06 |
JPH10512869A (ja) | 1998-12-08 |
DE59601604D1 (de) | 1999-05-12 |
CZ227097A3 (cs) | 1998-02-18 |
CZ289091B6 (cs) | 2001-10-17 |
GR3029933T3 (en) | 1999-07-30 |
HUP9801132A2 (hu) | 1998-08-28 |
IL116924A (en) | 2001-01-28 |
EP0805797B1 (de) | 1999-04-07 |
TW330928B (en) | 1998-05-01 |
KR19980701716A (ko) | 1998-06-25 |
AU691390B2 (en) | 1998-05-14 |
IL116924A0 (en) | 1996-05-14 |
HUP9801132A3 (en) | 1998-12-28 |
KR100391870B1 (ko) | 2003-10-17 |
EP0805797A1 (de) | 1997-11-12 |
ES2129951T3 (es) | 1999-06-16 |
SK92997A3 (en) | 1998-05-06 |
DE19502700A1 (de) | 1996-08-01 |
DK0805797T3 (da) | 1999-10-18 |
CN1073553C (zh) | 2001-10-24 |
CN1169715A (zh) | 1998-01-07 |
US5831093A (en) | 1998-11-03 |
AU4486996A (en) | 1996-08-14 |
CA2211390A1 (en) | 1996-08-01 |
ATE178586T1 (de) | 1999-04-15 |
ZA96610B (en) | 1997-06-26 |
WO1996022967A1 (de) | 1996-08-01 |
NZ300198A (en) | 1999-02-25 |
BR9606855A (pt) | 1997-11-25 |
HU220590B1 (hu) | 2002-03-28 |
JP3778567B2 (ja) | 2006-05-24 |
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