CA1241664A - Process for the preparation of 1-naphthylamine - Google Patents
Process for the preparation of 1-naphthylamineInfo
- Publication number
- CA1241664A CA1241664A CA000490275A CA490275A CA1241664A CA 1241664 A CA1241664 A CA 1241664A CA 000490275 A CA000490275 A CA 000490275A CA 490275 A CA490275 A CA 490275A CA 1241664 A CA1241664 A CA 1241664A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- nitronaphthalene
- weight
- ppm
- activated charcoal
- 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 abstract description 35
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 4
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 claims abstract description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- ZJYJZEAJZXVAMF-UHFFFAOYSA-N 2-nitronaphthalene Chemical class C1=CC=CC2=CC([N+](=O)[O-])=CC=C21 ZJYJZEAJZXVAMF-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000036647 reaction Effects 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 21
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229940023032 activated charcoal Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- -1 amino com-pounds Chemical class 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229940106265 charcoal Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RCURQHDMKQNLQF-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-amine Chemical compound C1CCCC2C(N)CCCC21 RCURQHDMKQNLQF-UHFFFAOYSA-N 0.000 description 1
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- OEEJLOZQSKNWQQ-UHFFFAOYSA-N 2-nitro-1-benzothiophene Chemical class C1=CC=C2SC([N+](=O)[O-])=CC2=C1 OEEJLOZQSKNWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3433240.5 | 1984-09-11 | ||
| DE19843433240 DE3433240A1 (de) | 1984-09-11 | 1984-09-11 | Verfahren zur herstellung von 1-naphthylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1241664A true CA1241664A (en) | 1988-09-06 |
Family
ID=6245069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000490275A Expired CA1241664A (en) | 1984-09-11 | 1985-09-09 | Process for the preparation of 1-naphthylamine |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0174563B1 (enrdf_load_html_response) |
| JP (1) | JPS6168451A (enrdf_load_html_response) |
| KR (1) | KR920005379B1 (enrdf_load_html_response) |
| CA (1) | CA1241664A (enrdf_load_html_response) |
| DE (2) | DE3433240A1 (enrdf_load_html_response) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5410085A (en) * | 1992-10-27 | 1995-04-25 | Bayer Aktiengesellschaft | Process for the preparation of chlorine-substituted aromatic amines and of catalysts |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1096444C (zh) * | 1996-10-10 | 2002-12-18 | 常州市常宇化工厂 | 一种利用结晶分离法制备甲萘胺的方法 |
| CN1052971C (zh) * | 1998-03-13 | 2000-05-31 | 常州市常宇化工厂 | 工业品高纯度甲萘胺的制备方法 |
| CN100419883C (zh) * | 2003-12-04 | 2008-09-17 | 松下电器产业株式会社 | 光信息重现设备 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB227481A (en) * | 1923-08-27 | 1924-12-29 | Gualtiero Poma | An improved process for the preparation of alphanaphthylamine |
| US3499034A (en) * | 1966-08-01 | 1970-03-03 | Du Pont | Hydrogenation of aromatic nitro compounds |
| DE2036313C3 (de) * | 1970-07-22 | 1982-03-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Halogen-substituiertenaromatischen Aminen |
| DE2452015C2 (de) * | 1974-11-02 | 1984-01-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Diaminonaphthalin |
| DE2456308A1 (de) * | 1974-11-28 | 1976-08-12 | Bayer Ag | Verfahren zur herstellung von aminoverbindungen |
| DE2519838A1 (de) * | 1975-05-03 | 1976-11-11 | Bayer Ag | Verfahren zur herstellung von aminoverbindungen |
-
1984
- 1984-09-11 DE DE19843433240 patent/DE3433240A1/de not_active Withdrawn
-
1985
- 1985-08-30 EP EP85110919A patent/EP0174563B1/de not_active Expired
- 1985-08-30 DE DE8585110919T patent/DE3561057D1/de not_active Expired
- 1985-09-06 JP JP60196110A patent/JPS6168451A/ja active Granted
- 1985-09-09 CA CA000490275A patent/CA1241664A/en not_active Expired
- 1985-09-10 KR KR1019850006604A patent/KR920005379B1/ko not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5410085A (en) * | 1992-10-27 | 1995-04-25 | Bayer Aktiengesellschaft | Process for the preparation of chlorine-substituted aromatic amines and of catalysts |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3561057D1 (en) | 1988-01-07 |
| JPS6168451A (ja) | 1986-04-08 |
| JPH0246022B2 (enrdf_load_html_response) | 1990-10-12 |
| KR860002449A (ko) | 1986-04-26 |
| EP0174563B1 (de) | 1987-11-25 |
| EP0174563A1 (de) | 1986-03-19 |
| DE3433240A1 (de) | 1986-03-20 |
| KR920005379B1 (ko) | 1992-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |