BE897878A - Coproduction d'aniline et de diphenylamine - Google Patents
Coproduction d'aniline et de diphenylamine Download PDFInfo
- Publication number
- BE897878A BE897878A BE0/211617A BE211617A BE897878A BE 897878 A BE897878 A BE 897878A BE 0/211617 A BE0/211617 A BE 0/211617A BE 211617 A BE211617 A BE 211617A BE 897878 A BE897878 A BE 897878A
- Authority
- BE
- Belgium
- Prior art keywords
- aniline
- diphenylamine
- phenol
- mixture
- reaction
- Prior art date
Links
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims abstract description 216
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 55
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 315
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 134
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 95
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 25
- 239000011541 reaction mixture Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 238000004064 recycling Methods 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- 239000013067 intermediate product Substances 0.000 claims description 3
- 150000001448 anilines Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000005755 formation reaction Methods 0.000 claims 8
- 238000009434 installation Methods 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- 230000008901 benefit Effects 0.000 description 7
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- DQLGIONSPPKALA-UHFFFAOYSA-N phenylazanium;phenoxide Chemical compound NC1=CC=CC=C1.OC1=CC=CC=C1 DQLGIONSPPKALA-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- -1 catalyst Chemical compound 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 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
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/431,532 US4404399A (en) | 1982-09-30 | 1982-09-30 | Coproduction of aniline and diphenylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE897878A true BE897878A (fr) | 1984-03-29 |
Family
ID=23712345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/211617A BE897878A (fr) | 1982-09-30 | 1983-09-29 | Coproduction d'aniline et de diphenylamine |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4404399A (h) |
| JP (1) | JPS5984848A (h) |
| BE (1) | BE897878A (h) |
| DE (1) | DE3335693A1 (h) |
| FR (1) | FR2540865B1 (h) |
| GB (1) | GB2128610B (h) |
| IN (1) | IN159751B (h) |
| IT (1) | IT1174783B (h) |
| NL (1) | NL8303356A (h) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4480127A (en) * | 1983-05-20 | 1984-10-30 | The Halcon Sd Group, Inc. | Process for the production of variable amounts of DPA and aniline using only phenol and ammonia as the feedstock |
| US4922024A (en) * | 1988-04-14 | 1990-05-01 | The Dow Chemical Company | Amination process employing group vib metal catalysts |
| DE3819128C2 (de) * | 1988-06-04 | 1995-10-26 | Conducta Endress & Hauser | Gasdetektionssystem |
| US5030740A (en) * | 1988-10-14 | 1991-07-09 | The Dow Chemical Company | Process for preparing linearly-extended polyalkylenepolyamines |
| US6140538A (en) | 1998-05-18 | 2000-10-31 | Flexsys America L.P. | Process for preparing 4-aminodiphenylamines |
| JP5638248B2 (ja) * | 2010-01-05 | 2014-12-10 | 日本曹達株式会社 | 架橋剤 |
| CN119500021B (zh) * | 2025-01-23 | 2025-05-02 | 陕西氢易能源科技有限公司 | 一种联产n-甲基苯胺和n，n-二甲基苯胺的系统 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1980102A (en) * | 1929-02-15 | 1934-11-06 | Goodrich Co B F | Method of manufacturing secondary aromatic amines |
| DE530736C (de) * | 1929-05-25 | 1931-07-31 | Rheinische Kampfer Fabrik G M | Verfahren zur katalytischen Arylierung von Phenolen und aromatischen Aminen |
| US2041782A (en) * | 1933-06-23 | 1936-05-26 | Goodrich Co B F | Preparation of secondary amines |
| US2503712A (en) * | 1947-12-31 | 1950-04-11 | Eastman Kodak Co | Multiple step process for preparing n,n' diphenyl p-phenylene diamine |
| NL296184A (h) * | 1962-08-10 | 1900-01-01 | ||
| US3418373A (en) * | 1965-04-12 | 1968-12-24 | Monsanto Co | Preparation of aromatic diamine mixtures |
| US3682782A (en) * | 1968-07-11 | 1972-08-08 | Halcon International Inc | Reduced pressure distillation process for recovering aniline from phenolaniline mixtures |
| US3578714A (en) * | 1968-10-28 | 1971-05-11 | Halcon International Inc | Process for preparing aniline from phenol |
| US3658906A (en) * | 1970-01-21 | 1972-04-25 | Sherwin Willlams Co The | Multiphase amination process of nitrophenols |
| JPS5413122B2 (h) * | 1973-05-23 | 1979-05-29 | ||
| US4017544A (en) * | 1974-01-23 | 1977-04-12 | Monsanto Company | N-(nitroalkyl)-N'-phenyl-p-phenylenediamines |
| DE2646379C3 (de) * | 1976-10-14 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-Alkylanilinen |
-
1982
- 1982-09-30 US US06/431,532 patent/US4404399A/en not_active Expired - Fee Related
-
1983
- 1983-08-23 IN IN573/DEL/83A patent/IN159751B/en unknown
- 1983-09-29 IT IT49067/83A patent/IT1174783B/it active
- 1983-09-29 BE BE0/211617A patent/BE897878A/fr not_active IP Right Cessation
- 1983-09-29 FR FR8315534A patent/FR2540865B1/fr not_active Expired
- 1983-09-30 DE DE19833335693 patent/DE3335693A1/de not_active Withdrawn
- 1983-09-30 NL NL8303356A patent/NL8303356A/nl not_active Application Discontinuation
- 1983-09-30 GB GB08326324A patent/GB2128610B/en not_active Expired
- 1983-09-30 JP JP58184344A patent/JPS5984848A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2540865A1 (fr) | 1984-08-17 |
| US4404399A (en) | 1983-09-13 |
| JPS5984848A (ja) | 1984-05-16 |
| GB2128610B (en) | 1986-04-23 |
| IN159751B (h) | 1987-06-06 |
| GB8326324D0 (en) | 1983-11-02 |
| IT1174783B (it) | 1987-07-01 |
| GB2128610A (en) | 1984-05-02 |
| DE3335693A1 (de) | 1984-04-05 |
| NL8303356A (nl) | 1984-04-16 |
| FR2540865B1 (fr) | 1985-07-12 |
| IT8349067A0 (it) | 1983-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: THE HALCON SD GROUP INC. Effective date: 19860930 |