DE2156051C3 - Verfahren zur Herstellung von 4-Chlor-2,5-dimethoxy-anilin - Google Patents
Verfahren zur Herstellung von 4-Chlor-2,5-dimethoxy-anilinInfo
- Publication number
- DE2156051C3 DE2156051C3 DE2156051A DE2156051A DE2156051C3 DE 2156051 C3 DE2156051 C3 DE 2156051C3 DE 2156051 A DE2156051 A DE 2156051A DE 2156051 A DE2156051 A DE 2156051A DE 2156051 C3 DE2156051 C3 DE 2156051C3
- Authority
- DE
- Germany
- Prior art keywords
- german
- platinum
- nitro
- catalyst
- reduction
- 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 7
- 238000002360 preparation method Methods 0.000 title claims 3
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 238000006722 reduction reaction Methods 0.000 claims description 9
- 150000002828 nitro derivatives Chemical class 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052697 platinum Inorganic materials 0.000 claims 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 206010010774 Constipation Diseases 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- 241000212342 Sium Species 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000004280 Sodium formate Substances 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- -1 amino compound Chemical class 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910021538 borax Inorganic materials 0.000 claims 1
- 150000008422 chlorobenzenes Chemical class 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 238000003825 pressing Methods 0.000 claims 1
- 238000004080 punching Methods 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims 1
- 235000019254 sodium formate Nutrition 0.000 claims 1
- 239000004328 sodium tetraborate Substances 0.000 claims 1
- 235000010339 sodium tetraborate Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003738 xylenes Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- GOBGCUAZYIPRTM-UHFFFAOYSA-N [Na+].[Na+].OB(O)OB([O-])[O-] Chemical compound [Na+].[Na+].OB(O)OB([O-])[O-] GOBGCUAZYIPRTM-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE791300D BE791300A (fr) | 1971-11-11 | Procede de preparation de la chloro-4 dimethoxy-2,5 aniline | |
| DE2156051A DE2156051C3 (de) | 1971-11-11 | 1971-11-11 | Verfahren zur Herstellung von 4-Chlor-2,5-dimethoxy-anilin |
| DD166310A DD99356A5 (OSRAM) | 1971-11-11 | 1972-10-18 | |
| ZA727738A ZA727738B (en) | 1971-11-11 | 1972-11-01 | Process for the preparation of 4-chloro-2-dimethoxy-aniline |
| RO72709A RO62342A (OSRAM) | 1971-11-11 | 1972-11-02 | |
| ES408273A ES408273A1 (es) | 1971-11-11 | 1972-11-04 | Procedimiento para la preparacion de 4-cloro-2,5-dimetoxi-anilina. |
| NL7214964A NL7214964A (OSRAM) | 1971-11-11 | 1972-11-06 | |
| CS7507A CS173610B2 (OSRAM) | 1971-11-11 | 1972-11-07 | |
| AU48583/72A AU474209B2 (en) | 1971-11-11 | 1972-11-07 | Process for the preparation of 4-chloro-2, 5-dimethoxy-aniline |
| IL40777A IL40777A (en) | 1971-11-11 | 1972-11-08 | Process for the preparation of 4-chloro-2,5-dimethoxy-aniline |
| GB5151772A GB1393428A (en) | 1971-11-11 | 1972-11-08 | Process for the preparation of 4-chloro-2,5-dimethoxyaniline |
| SU1843993A SU474135A3 (ru) | 1971-11-11 | 1972-11-09 | Способ получени 4-хлор-2,5-диметоксианилина |
| HUHO1523A HU165205B (OSRAM) | 1971-11-11 | 1972-11-09 | |
| AT952372A AT331210B (de) | 1971-11-11 | 1972-11-09 | Verfahren zur herstellung von 4-chlor-2,5-dimethoxy-anilin |
| IT31481/72A IT970356B (it) | 1971-11-11 | 1972-11-09 | Procedimento per la preparazione di 4 cloro 2 5 dimetossi anilina |
| CH1630472A CH575377A5 (OSRAM) | 1971-11-11 | 1972-11-09 | |
| JP11219772A JPS5644060B2 (OSRAM) | 1971-11-11 | 1972-11-10 | |
| FR7239905A FR2160166A5 (OSRAM) | 1971-11-11 | 1972-11-10 | |
| PL1972158797A PL85137B1 (OSRAM) | 1971-11-11 | 1972-11-10 | |
| CA156,152A CA995248A (en) | 1971-11-11 | 1972-11-10 | Process for the preparation of 4-chloro-2,5-dimethoxy-aniline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156051A DE2156051C3 (de) | 1971-11-11 | 1971-11-11 | Verfahren zur Herstellung von 4-Chlor-2,5-dimethoxy-anilin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2156051A1 DE2156051A1 (de) | 1973-05-17 |
| DE2156051B2 DE2156051B2 (de) | 1974-03-28 |
| DE2156051C3 true DE2156051C3 (de) | 1974-10-31 |
Family
ID=5824830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2156051A Expired DE2156051C3 (de) | 1971-11-11 | 1971-11-11 | Verfahren zur Herstellung von 4-Chlor-2,5-dimethoxy-anilin |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5644060B2 (OSRAM) |
| AT (1) | AT331210B (OSRAM) |
| AU (1) | AU474209B2 (OSRAM) |
| BE (1) | BE791300A (OSRAM) |
| CA (1) | CA995248A (OSRAM) |
| CH (1) | CH575377A5 (OSRAM) |
| CS (1) | CS173610B2 (OSRAM) |
| DD (1) | DD99356A5 (OSRAM) |
| DE (1) | DE2156051C3 (OSRAM) |
| ES (1) | ES408273A1 (OSRAM) |
| FR (1) | FR2160166A5 (OSRAM) |
| GB (1) | GB1393428A (OSRAM) |
| HU (1) | HU165205B (OSRAM) |
| IL (1) | IL40777A (OSRAM) |
| IT (1) | IT970356B (OSRAM) |
| NL (1) | NL7214964A (OSRAM) |
| PL (1) | PL85137B1 (OSRAM) |
| RO (1) | RO62342A (OSRAM) |
| SU (1) | SU474135A3 (OSRAM) |
| ZA (1) | ZA727738B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2455704C3 (de) * | 1974-11-25 | 1978-06-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 4-Chlor-23-dimethoxy anilin |
| CA1148562A (en) * | 1979-02-22 | 1983-06-21 | Alfred J. Bird | Catalyst for the hydrogenation of halogen substituted aromatic nitro compounds |
| JPS58159957U (ja) * | 1982-04-19 | 1983-10-25 | 日本発条株式会社 | ヘツドレスト上，下調節機構 |
| DE3821013A1 (de) * | 1988-06-22 | 1989-12-28 | Hoechst Ag | Verfahren zur herstellung von 4-chlor-2,5-dimethoxyanilin |
-
0
- BE BE791300D patent/BE791300A/xx not_active IP Right Cessation
-
1971
- 1971-11-11 DE DE2156051A patent/DE2156051C3/de not_active Expired
-
1972
- 1972-10-18 DD DD166310A patent/DD99356A5/xx unknown
- 1972-11-01 ZA ZA727738A patent/ZA727738B/xx unknown
- 1972-11-02 RO RO72709A patent/RO62342A/ro unknown
- 1972-11-04 ES ES408273A patent/ES408273A1/es not_active Expired
- 1972-11-06 NL NL7214964A patent/NL7214964A/xx not_active Application Discontinuation
- 1972-11-07 CS CS7507A patent/CS173610B2/cs unknown
- 1972-11-07 AU AU48583/72A patent/AU474209B2/en not_active Expired
- 1972-11-08 IL IL40777A patent/IL40777A/en unknown
- 1972-11-08 GB GB5151772A patent/GB1393428A/en not_active Expired
- 1972-11-09 AT AT952372A patent/AT331210B/de not_active IP Right Cessation
- 1972-11-09 HU HUHO1523A patent/HU165205B/hu unknown
- 1972-11-09 SU SU1843993A patent/SU474135A3/ru active
- 1972-11-09 IT IT31481/72A patent/IT970356B/it active
- 1972-11-09 CH CH1630472A patent/CH575377A5/xx not_active IP Right Cessation
- 1972-11-10 CA CA156,152A patent/CA995248A/en not_active Expired
- 1972-11-10 PL PL1972158797A patent/PL85137B1/pl unknown
- 1972-11-10 FR FR7239905A patent/FR2160166A5/fr not_active Expired
- 1972-11-10 JP JP11219772A patent/JPS5644060B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL40777A (en) | 1976-04-30 |
| DE2156051A1 (de) | 1973-05-17 |
| AU4858372A (en) | 1974-05-09 |
| AU474209B2 (en) | 1976-07-15 |
| ES408273A1 (es) | 1975-11-16 |
| GB1393428A (en) | 1975-05-07 |
| JPS4857938A (OSRAM) | 1973-08-14 |
| IT970356B (it) | 1974-04-10 |
| FR2160166A5 (OSRAM) | 1973-06-22 |
| IL40777A0 (en) | 1973-01-30 |
| BE791300A (fr) | 1973-05-14 |
| CS173610B2 (OSRAM) | 1977-02-28 |
| AT331210B (de) | 1976-08-10 |
| CH575377A5 (OSRAM) | 1976-05-14 |
| RO62342A (OSRAM) | 1977-08-15 |
| SU474135A3 (ru) | 1975-06-14 |
| JPS5644060B2 (OSRAM) | 1981-10-16 |
| DE2156051B2 (de) | 1974-03-28 |
| HU165205B (OSRAM) | 1974-07-27 |
| DD99356A5 (OSRAM) | 1973-08-05 |
| ATA952372A (de) | 1975-11-15 |
| CA995248A (en) | 1976-08-17 |
| NL7214964A (OSRAM) | 1973-05-15 |
| ZA727738B (en) | 1973-09-26 |
| PL85137B1 (OSRAM) | 1976-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |