DE2357386A1 - Verfahren zur herstellung aromatischer hydroxylamine ausgehend von den nitrosoderivaten - Google Patents
Verfahren zur herstellung aromatischer hydroxylamine ausgehend von den nitrosoderivatenInfo
- Publication number
- DE2357386A1 DE2357386A1 DE2357386A DE2357386A DE2357386A1 DE 2357386 A1 DE2357386 A1 DE 2357386A1 DE 2357386 A DE2357386 A DE 2357386A DE 2357386 A DE2357386 A DE 2357386A DE 2357386 A1 DE2357386 A1 DE 2357386A1
- Authority
- DE
- Germany
- Prior art keywords
- benzene ring
- radical
- nitroso
- aromatic
- organic base
- 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
- 150000002832 nitroso derivatives Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 2
- -1 aromatic hydroxylamines Chemical class 0.000 claims description 17
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- OQMIHXJMPSZIKC-UHFFFAOYSA-N 1,2,3-trimethyl-4-nitrosobenzene Chemical compound CC1=CC=C(N=O)C(C)=C1C OQMIHXJMPSZIKC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
- OJIGVTIAMIAFAO-UHFFFAOYSA-N n-(2,3,4-trimethylphenyl)hydroxylamine Chemical compound CC1=CC=C(NO)C(C)=C1C OJIGVTIAMIAFAO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical group ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 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
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000000178 monomer Substances 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
- FEKDDEQYKDNKJG-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrosobenzene Chemical compound CC1=CC(C)=C(N=O)C(C)=C1 FEKDDEQYKDNKJG-UHFFFAOYSA-N 0.000 description 1
- TWLBRQVYXPMCFK-UHFFFAOYSA-N 1-methyl-2-nitrosobenzene Chemical compound CC1=CC=CC=C1N=O TWLBRQVYXPMCFK-UHFFFAOYSA-N 0.000 description 1
- NYJYFSGMYHSTNZ-UHFFFAOYSA-N 1-methyl-4-nitrosobenzene Chemical compound CC1=CC=C(N=O)C=C1 NYJYFSGMYHSTNZ-UHFFFAOYSA-N 0.000 description 1
- CPOGBRPDTGTFJQ-UHFFFAOYSA-N 1-nitroso-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(N=O)C=C1 CPOGBRPDTGTFJQ-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
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols 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
- 229960003237 betaine Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940077451 coniine Drugs 0.000 description 1
- 229930016881 coniine Natural products 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 238000003756 stirring 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)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7240702A FR2206757A5 (enrdf_load_stackoverflow) | 1972-11-16 | 1972-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2357386A1 true DE2357386A1 (de) | 1974-05-22 |
Family
ID=9107264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2357386A Pending DE2357386A1 (de) | 1972-11-16 | 1973-11-16 | Verfahren zur herstellung aromatischer hydroxylamine ausgehend von den nitrosoderivaten |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5046632A (enrdf_load_stackoverflow) |
| BE (1) | BE807346A (enrdf_load_stackoverflow) |
| CH (1) | CH577455A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2357386A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2206757A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1429389A (enrdf_load_stackoverflow) |
| IT (1) | IT1001808B (enrdf_load_stackoverflow) |
| NL (1) | NL7315327A (enrdf_load_stackoverflow) |
| SU (1) | SU497763A3 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5319142A (en) * | 1992-10-06 | 1994-06-07 | Hoechst Celanese Corporation | Process for preparing substituted and unsubstituted arylalkylamines |
| 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 |
-
1972
- 1972-11-16 FR FR7240702A patent/FR2206757A5/fr not_active Expired
-
1973
- 1973-11-08 NL NL7315327A patent/NL7315327A/xx unknown
- 1973-11-14 JP JP48128148A patent/JPS5046632A/ja active Pending
- 1973-11-14 BE BE137774A patent/BE807346A/xx unknown
- 1973-11-15 GB GB5309773A patent/GB1429389A/en not_active Expired
- 1973-11-15 SU SU1971531A patent/SU497763A3/ru active
- 1973-11-15 CH CH1606373A patent/CH577455A5/xx not_active IP Right Cessation
- 1973-11-16 IT IT31433/73A patent/IT1001808B/it active
- 1973-11-16 DE DE2357386A patent/DE2357386A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2206757A5 (enrdf_load_stackoverflow) | 1974-06-07 |
| GB1429389A (en) | 1976-03-24 |
| IT1001808B (it) | 1976-04-30 |
| CH577455A5 (enrdf_load_stackoverflow) | 1976-07-15 |
| JPS5046632A (enrdf_load_stackoverflow) | 1975-04-25 |
| NL7315327A (enrdf_load_stackoverflow) | 1974-05-20 |
| BE807346A (fr) | 1974-05-14 |
| SU497763A3 (ru) | 1975-12-30 |
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