SU454734A3 - Способ получени ароматических гидроксиламинов - Google Patents
Способ получени ароматических гидроксиламиновInfo
- Publication number
- SU454734A3 SU454734A3 SU1919374A SU1919374A SU454734A3 SU 454734 A3 SU454734 A3 SU 454734A3 SU 1919374 A SU1919374 A SU 1919374A SU 1919374 A SU1919374 A SU 1919374A SU 454734 A3 SU454734 A3 SU 454734A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogenation
- catalyst
- nitrobenzene
- derivative
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- -1 aromatic hydroxylamines Chemical class 0.000 title description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 241001425930 Latina Species 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 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
- 239000003208 petroleum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 239000007864 aqueous solution Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-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
- XBYFRIKYRIUDDQ-UHFFFAOYSA-N n-(4-propan-2-ylphenyl)hydroxylamine Chemical compound CC(C)C1=CC=C(NO)C=C1 XBYFRIKYRIUDDQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction 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 |
|---|---|
| SU454734A3 true SU454734A3 (ru) | 1974-12-25 |
Family
ID=9099233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1919374A SU454734A3 (ru) | 1972-05-29 | 1973-05-28 | Способ получени ароматических гидроксиламинов |
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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (7)
| 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 |
| DK1012144T3 (da) | 1997-09-05 | 2003-07-14 | Basf Ag | Fremgangsmåde til fremstilling af (hetero)aromatiske hydroxylaminer |
| DE19753462A1 (de) * | 1997-12-02 | 1999-06-10 | Consortium Elektrochem Ind | Verfahren zur Herstellung organischer Hydroxylamine |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4961126A (enExample) | 1974-06-13 |
| CH562775A5 (enExample) | 1975-06-13 |
| BE800142A (fr) | 1973-11-28 |
| NL7307070A (enExample) | 1973-12-03 |
| DE2327412A1 (de) | 1973-12-13 |
| FR2186963A5 (enExample) | 1974-01-11 |
| CA1001658A (fr) | 1976-12-14 |
| IT988764B (it) | 1975-04-30 |
| GB1388523A (en) | 1975-03-26 |
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