DE2609530C2 - Verfahren zur Herstellung von Hydrazobenzolen - Google Patents
Verfahren zur Herstellung von HydrazobenzolenInfo
- Publication number
- DE2609530C2 DE2609530C2 DE2609530A DE2609530A DE2609530C2 DE 2609530 C2 DE2609530 C2 DE 2609530C2 DE 2609530 A DE2609530 A DE 2609530A DE 2609530 A DE2609530 A DE 2609530A DE 2609530 C2 DE2609530 C2 DE 2609530C2
- Authority
- DE
- Germany
- Prior art keywords
- reduction
- hydrogen
- sodium hydroxide
- water
- mixture
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 238000006722 reduction reaction Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000009467 reduction Effects 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000007868 Raney catalyst Substances 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- NKUNBLUACJUHOA-UHFFFAOYSA-N (2-chlorophenyl)-(2-chlorophenyl)imino-oxidoazanium Chemical compound C=1C=CC=C(Cl)C=1[N+]([O-])=NC1=CC=CC=C1Cl NKUNBLUACJUHOA-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- -1 carboxy, sulfo Chemical group 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 230000008707 rearrangement Effects 0.000 description 7
- 238000011946 reduction process Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- IWKMQNKKYZERHI-UHFFFAOYSA-N 1,2-bis(2-chlorophenyl)hydrazine Chemical compound ClC1=CC=CC=C1NNC1=CC=CC=C1Cl IWKMQNKKYZERHI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- SXCDGVDBGGCCLV-UHFFFAOYSA-N (3-chlorophenyl)-(3-chlorophenyl)imino-oxidoazanium Chemical compound C=1C=CC(Cl)=CC=1[N+]([O-])=NC1=CC=CC(Cl)=C1 SXCDGVDBGGCCLV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- KCZFLPPCFOHPNI-UHFFFAOYSA-N alumane;iron Chemical compound [AlH3].[Fe] KCZFLPPCFOHPNI-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2609530A DE2609530C2 (de) | 1976-03-08 | 1976-03-08 | Verfahren zur Herstellung von Hydrazobenzolen |
| IN153/CAL/77A IN155288B (https=) | 1976-03-08 | 1977-02-02 | |
| MX167948A MX144355A (es) | 1976-03-08 | 1977-02-07 | Procedimiento mejorado para la obtencion de hidrazobencenos |
| CH267877A CH629180A5 (de) | 1976-03-08 | 1977-03-03 | Verfahren zur herstellung von hydrazobenzol. |
| US05/774,453 US4550207A (en) | 1976-03-08 | 1977-03-04 | Process for the preparation of benzene compounds |
| JP52022892A JPS5949223B2 (ja) | 1976-03-08 | 1977-03-04 | ベンゼン化合物の製造方法 |
| GB9204/77A GB1509372A (en) | 1976-03-08 | 1977-03-04 | Process for the preparation of benzene compounds |
| IT20962/77A IT1078659B (it) | 1976-03-08 | 1977-03-04 | Processo per la produzione di idrazobenzene |
| BR7701362A BR7701362A (pt) | 1976-03-08 | 1977-03-07 | Processo para a preparacao de hidrazobenzeno |
| BE175520A BE852148A (fr) | 1976-03-08 | 1977-03-07 | Procede de production d'hydrazobenzenes |
| ES456576A ES456576A1 (es) | 1976-03-08 | 1977-03-07 | Procedimiento para la obtencion de hidrazobenceno. |
| FR7706799A FR2343721A1 (fr) | 1976-03-08 | 1977-03-08 | Procede de production d'hydrazobenzenes |
| JP57044752A JPS5823650A (ja) | 1976-03-08 | 1982-03-23 | ４，４′−ジアミノジフエニル誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2609530A DE2609530C2 (de) | 1976-03-08 | 1976-03-08 | Verfahren zur Herstellung von Hydrazobenzolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2609530B1 DE2609530B1 (de) | 1977-08-04 |
| DE2609530C2 true DE2609530C2 (de) | 1983-06-01 |
Family
ID=5971808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2609530A Expired DE2609530C2 (de) | 1976-03-08 | 1976-03-08 | Verfahren zur Herstellung von Hydrazobenzolen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4550207A (https=) |
| JP (2) | JPS5949223B2 (https=) |
| BE (1) | BE852148A (https=) |
| BR (1) | BR7701362A (https=) |
| CH (1) | CH629180A5 (https=) |
| DE (1) | DE2609530C2 (https=) |
| ES (1) | ES456576A1 (https=) |
| FR (1) | FR2343721A1 (https=) |
| GB (1) | GB1509372A (https=) |
| IN (1) | IN155288B (https=) |
| IT (1) | IT1078659B (https=) |
| MX (1) | MX144355A (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7904418A (nl) | 1979-06-05 | 1980-12-09 | Borma Bv | Werkwijze ter bereiding van aromatische hydrazo-of diaminodifenylverbindingen. |
| JPS6240621U (https=) * | 1985-08-30 | 1987-03-11 | ||
| JPS6352230U (https=) * | 1986-09-24 | 1988-04-08 | ||
| US7772436B2 (en) * | 2004-11-05 | 2010-08-10 | Air Water Inc. | Process for producing 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl |
| ES2536706T3 (es) * | 2009-12-18 | 2015-05-27 | Basf Se | Procedimiento en dos etapas para la separación económica de catalizadores homogéneos en la síntesis de MDA |
| CN108976131A (zh) * | 2018-07-13 | 2018-12-11 | 山东隆信药业有限公司 | 一种水替代甲苯生产3,3′-二氯联苯胺盐酸盐的方法 |
| CN115928112A (zh) * | 2022-05-20 | 2023-04-07 | 北京化工大学 | 光电催化芳香胺制备芳香族偶氮化合物的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1589936A (en) * | 1925-11-02 | 1926-06-22 | Newport Co | Process for the reduction of azo compounds to hydrazo compounds |
| US2233128A (en) * | 1939-11-08 | 1941-02-25 | Du Pont | Process for the manufacture of benzidine |
| US2640081A (en) * | 1949-10-04 | 1953-05-26 | Sherwin Williams Co | Process for manufacturing benzidine type compounds |
| US3063980A (en) * | 1957-07-09 | 1962-11-13 | Gen Aniline & Film Corp | Process for reducing aromatic nitrogen compounds |
| US3361819A (en) * | 1964-06-05 | 1968-01-02 | Du Pont | Process for producing chlorinesubstituted aromatic amines |
| FR2302998A1 (fr) * | 1975-03-05 | 1976-10-01 | Colour Chem Ltd | Procede de preparation de derives de l'hydrazobenzene |
| BE832269A (fr) * | 1975-08-08 | 1976-02-09 | Pigments de benzidine et leur fabrication. |
-
1976
- 1976-03-08 DE DE2609530A patent/DE2609530C2/de not_active Expired
-
1977
- 1977-02-02 IN IN153/CAL/77A patent/IN155288B/en unknown
- 1977-02-07 MX MX167948A patent/MX144355A/es unknown
- 1977-03-03 CH CH267877A patent/CH629180A5/de not_active IP Right Cessation
- 1977-03-04 GB GB9204/77A patent/GB1509372A/en not_active Expired
- 1977-03-04 IT IT20962/77A patent/IT1078659B/it active
- 1977-03-04 JP JP52022892A patent/JPS5949223B2/ja not_active Expired
- 1977-03-04 US US05/774,453 patent/US4550207A/en not_active Expired - Lifetime
- 1977-03-07 BE BE175520A patent/BE852148A/xx unknown
- 1977-03-07 BR BR7701362A patent/BR7701362A/pt unknown
- 1977-03-07 ES ES456576A patent/ES456576A1/es not_active Expired
- 1977-03-08 FR FR7706799A patent/FR2343721A1/fr active Granted
-
1982
- 1982-03-23 JP JP57044752A patent/JPS5823650A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1078659B (it) | 1985-05-08 |
| CH629180A5 (de) | 1982-04-15 |
| US4550207A (en) | 1985-10-29 |
| FR2343721A1 (fr) | 1977-10-07 |
| FR2343721B1 (https=) | 1981-02-13 |
| BR7701362A (pt) | 1978-05-02 |
| DE2609530B1 (de) | 1977-08-04 |
| JPS5823650A (ja) | 1983-02-12 |
| MX144355A (es) | 1981-10-05 |
| JPS52108932A (en) | 1977-09-12 |
| ES456576A1 (es) | 1978-02-16 |
| IN155288B (https=) | 1985-01-12 |
| JPS5949223B2 (ja) | 1984-12-01 |
| BE852148A (fr) | 1977-09-07 |
| GB1509372A (en) | 1978-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Publication of the examined application without previous publication of unexamined application | ||
| C2 | Grant after previous publication (2nd publication) |