DE2327412A1 - Verfahren zur herstellung von aromatischen hydroxylaminen - Google Patents
Verfahren zur herstellung von aromatischen hydroxylaminenInfo
- Publication number
- DE2327412A1 DE2327412A1 DE2327412A DE2327412A DE2327412A1 DE 2327412 A1 DE2327412 A1 DE 2327412A1 DE 2327412 A DE2327412 A DE 2327412A DE 2327412 A DE2327412 A DE 2327412A DE 2327412 A1 DE2327412 A1 DE 2327412A1
- Authority
- DE
- Germany
- Prior art keywords
- benzene ring
- organic base
- hydrogenation
- platinum
- radical
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 150000002443 hydroxylamines Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 18
- -1 aromatic hydroxylamines Chemical class 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000007530 organic bases Chemical class 0.000 claims description 10
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 7
- 150000002828 nitro derivatives Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 4
- HBPWZZBSVWZXTN-UHFFFAOYSA-N 1,2,3-trimethyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=C1C HBPWZZBSVWZXTN-UHFFFAOYSA-N 0.000 description 3
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- SCEKDQTVGHRSNS-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrobenzene Chemical compound CC1=CC(C)=C([N+]([O-])=O)C(C)=C1 SCEKDQTVGHRSNS-UHFFFAOYSA-N 0.000 description 2
- JXMYUMNAEKRMIP-UHFFFAOYSA-N 1-nitro-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C([N+]([O-])=O)C=C1 JXMYUMNAEKRMIP-UHFFFAOYSA-N 0.000 description 2
- RLIPQCDHACHPJW-UHFFFAOYSA-N 2,3,4-trimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1C RLIPQCDHACHPJW-UHFFFAOYSA-N 0.000 description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- NDNUANOUGZGEPO-QMMMGPOBSA-N (+)-coniine Chemical compound CCC[C@H]1CCCCN1 NDNUANOUGZGEPO-QMMMGPOBSA-N 0.000 description 1
- INMYTBBXRJWIOA-UHFFFAOYSA-N 1-butyl-3-nitrobenzene Chemical compound CCCCC1=CC=CC([N+]([O-])=O)=C1 INMYTBBXRJWIOA-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- IDSGFSCSMXRJON-UHFFFAOYSA-N N-Carbamyl-L-glutamicacid Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=CC=C1 IDSGFSCSMXRJON-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 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
- 241000872198 Serjania polyphylla Species 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GXCSNALCLRPEAS-CFYXSCKTSA-N azane (Z)-hydroxyimino-oxido-phenylazanium Chemical compound N.O\N=[N+](/[O-])c1ccccc1 GXCSNALCLRPEAS-CFYXSCKTSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940077451 coniine Drugs 0.000 description 1
- 229930016881 coniine Natural products 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical group CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- OJIGVTIAMIAFAO-UHFFFAOYSA-N n-(2,3,4-trimethylphenyl)hydroxylamine Chemical compound CC1=CC=C(NO)C(C)=C1C OJIGVTIAMIAFAO-UHFFFAOYSA-N 0.000 description 1
- OMYXQGTUTCZGCI-UHFFFAOYSA-N n-(2-methylphenyl)hydroxylamine Chemical compound CC1=CC=CC=C1NO OMYXQGTUTCZGCI-UHFFFAOYSA-N 0.000 description 1
- AGJOAIMUXIQLCN-UHFFFAOYSA-N n-(4-methylphenyl)hydroxylamine Chemical compound CC1=CC=C(NO)C=C1 AGJOAIMUXIQLCN-UHFFFAOYSA-N 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- HWLDNSXPUQTBOD-UHFFFAOYSA-N platinum-iridium alloy Chemical compound [Ir].[Pt] HWLDNSXPUQTBOD-UHFFFAOYSA-N 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NDNUANOUGZGEPO-UHFFFAOYSA-N rac-coniine Natural products CCCC1CCCCN1 NDNUANOUGZGEPO-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7219130A FR2186963A5 (enExample) | 1972-05-29 | 1972-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2327412A1 true DE2327412A1 (de) | 1973-12-13 |
Family
ID=9099233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2327412A Pending DE2327412A1 (de) | 1972-05-29 | 1973-05-29 | Verfahren zur herstellung von aromatischen hydroxylaminen |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4961126A (enExample) |
| BE (1) | BE800142A (enExample) |
| CA (1) | CA1001658A (enExample) |
| CH (1) | CH562775A5 (enExample) |
| DE (1) | DE2327412A1 (enExample) |
| FR (1) | FR2186963A5 (enExample) |
| GB (1) | GB1388523A (enExample) |
| IT (1) | IT988764B (enExample) |
| NL (1) | NL7307070A (enExample) |
| SU (1) | SU454734A3 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999028289A1 (de) * | 1997-12-02 | 1999-06-10 | Consortium für elektrochemische Industrie GmbH | Verfahren zur herstellung organischer hydroxylamine |
| US6255489B1 (en) | 1997-09-05 | 2001-07-03 | Basf Aktiengesellschaft | Method for producing (hetero)aromatic hydroxylamines |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA83304B (en) * | 1982-01-29 | 1983-10-26 | Mallinckrodt Inc | Process for the preparation of arylhydroxylamines |
| US4723030A (en) * | 1985-08-05 | 1988-02-02 | General Electric Company | Moderated reduction reactions for producing arylhydroxylamines |
| DE19610571A1 (de) * | 1996-03-18 | 1997-09-25 | Basf Ag | Verfahren und Zwischenprodukte zur Herstellung von Pyridyl-4-Fluoranilinen |
| RU2337092C1 (ru) * | 2007-01-09 | 2008-10-27 | Федеральное государственное унитарное предприятие Государственный научно-исследовательский институт "Кристалл" | Способ получения 4-гидроксиламино-2,6-динитротолуола и 3,5-динитро-1-гидроксиламинобензола |
| WO2011113884A1 (en) | 2010-03-18 | 2011-09-22 | Basf Se | N-carbomethoxy-n-methoxy-(2-chloromethyl)-anilines, their preparation and their use as precursors for preparing 2-(pyrazol-3'-yloxymethylene)-anilides |
| EP3587391A1 (en) | 2018-06-22 | 2020-01-01 | Basf Se | Process for preparing nitrobenzyl bromides |
-
1972
- 1972-05-29 FR FR7219130A patent/FR2186963A5/fr not_active Expired
-
1973
- 1973-05-21 NL NL7307070A patent/NL7307070A/xx unknown
- 1973-05-25 JP JP48058525A patent/JPS4961126A/ja active Pending
- 1973-05-28 CH CH766573A patent/CH562775A5/xx not_active IP Right Cessation
- 1973-05-28 SU SU1919374A patent/SU454734A3/ru active
- 1973-05-28 BE BE131611A patent/BE800142A/xx unknown
- 1973-05-28 CA CA172,476A patent/CA1001658A/fr not_active Expired
- 1973-05-29 GB GB2538973A patent/GB1388523A/en not_active Expired
- 1973-05-29 DE DE2327412A patent/DE2327412A1/de active Pending
- 1973-05-29 IT IT24769/73A patent/IT988764B/it active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255489B1 (en) | 1997-09-05 | 2001-07-03 | Basf Aktiengesellschaft | Method for producing (hetero)aromatic hydroxylamines |
| WO1999028289A1 (de) * | 1997-12-02 | 1999-06-10 | Consortium für elektrochemische Industrie GmbH | Verfahren zur herstellung organischer hydroxylamine |
| US6211410B1 (en) | 1997-12-02 | 2001-04-03 | Consortium für elektrochemische Industrie GmbH | Method for producing organic hydroxylamines |
Also Published As
| Publication number | Publication date |
|---|---|
| SU454734A3 (ru) | 1974-12-25 |
| JPS4961126A (enExample) | 1974-06-13 |
| CH562775A5 (enExample) | 1975-06-13 |
| BE800142A (fr) | 1973-11-28 |
| NL7307070A (enExample) | 1973-12-03 |
| FR2186963A5 (enExample) | 1974-01-11 |
| CA1001658A (fr) | 1976-12-14 |
| IT988764B (it) | 1975-04-30 |
| GB1388523A (en) | 1975-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |