CN1165513C - 用于制备芳族胺的连续方法 - Google Patents
用于制备芳族胺的连续方法 Download PDFInfo
- Publication number
- CN1165513C CN1165513C CNB988102986A CN98810298A CN1165513C CN 1165513 C CN1165513 C CN 1165513C CN B988102986 A CNB988102986 A CN B988102986A CN 98810298 A CN98810298 A CN 98810298A CN 1165513 C CN1165513 C CN 1165513C
- Authority
- CN
- China
- Prior art keywords
- aromatics
- compounds
- nitro
- hydrogen
- product stream
- 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 - Fee Related
Links
- 238000011437 continuous method Methods 0.000 title abstract 2
- 150000004982 aromatic amines Chemical class 0.000 title description 3
- 239000000047 product Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000768 polyamine Polymers 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 21
- 150000002828 nitro derivatives Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 13
- -1 dinitro compound Chemical class 0.000 claims description 6
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical group CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- 239000004210 ether based solvent Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 150000004984 aromatic diamines Chemical class 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 1
- INYDMNPNDHRJQJ-UHFFFAOYSA-N 3,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 INYDMNPNDHRJQJ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
Images
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19745465A DE19745465A1 (de) | 1997-10-15 | 1997-10-15 | Kontinuierliches Verfahren zur Herstellung von aromatischen Aminen |
DE19745465.8 | 1997-10-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1276780A CN1276780A (zh) | 2000-12-13 |
CN1165513C true CN1165513C (zh) | 2004-09-08 |
Family
ID=7845567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB988102986A Expired - Fee Related CN1165513C (zh) | 1997-10-15 | 1998-10-02 | 用于制备芳族胺的连续方法 |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP1023261B1 (zh) |
KR (1) | KR100566450B1 (zh) |
CN (1) | CN1165513C (zh) |
AU (1) | AU9748298A (zh) |
BR (1) | BR9813052A (zh) |
CA (1) | CA2306935A1 (zh) |
DE (2) | DE19745465A1 (zh) |
ES (1) | ES2174497T3 (zh) |
HK (1) | HK1033304A1 (zh) |
TW (1) | TW443998B (zh) |
WO (1) | WO1999019292A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1318602B1 (it) * | 2000-06-29 | 2003-08-27 | Enichem Spa | Procedimento per la produzione di ammine aromatiche. |
US6521791B1 (en) | 2001-11-09 | 2003-02-18 | Air Products And Chemicals, Inc. | Process for regenerating a monolith hydrogenation catalytic reactor |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2135155A1 (de) * | 1971-07-14 | 1973-02-22 | Bayer Ag | Katalysator zur reduktion von nitroverbindungen |
DE3315191A1 (de) * | 1983-04-27 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen herstellung von aromatischen diaminen unter gleichzeitiger erzeugung von dampf |
DE4323687A1 (de) * | 1993-07-15 | 1995-01-19 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von aromatischen Aminen |
DE4428017A1 (de) * | 1994-08-08 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von aromatischen Aminen |
FR2741877B1 (fr) * | 1995-12-01 | 1998-02-13 | Rhone Poulenc Chimie | Procede d'hydrogenation de composes nitres aromatiques |
-
1997
- 1997-10-15 DE DE19745465A patent/DE19745465A1/de not_active Withdrawn
-
1998
- 1998-09-25 TW TW087115933A patent/TW443998B/zh not_active IP Right Cessation
- 1998-10-02 CN CNB988102986A patent/CN1165513C/zh not_active Expired - Fee Related
- 1998-10-02 DE DE59803298T patent/DE59803298D1/de not_active Expired - Lifetime
- 1998-10-02 CA CA002306935A patent/CA2306935A1/en not_active Abandoned
- 1998-10-02 BR BR9813052-8A patent/BR9813052A/pt not_active IP Right Cessation
- 1998-10-02 EP EP98951488A patent/EP1023261B1/de not_active Expired - Lifetime
- 1998-10-02 ES ES98951488T patent/ES2174497T3/es not_active Expired - Lifetime
- 1998-10-02 WO PCT/EP1998/006275 patent/WO1999019292A1/de active IP Right Grant
- 1998-10-02 AU AU97482/98A patent/AU9748298A/en not_active Abandoned
- 1998-10-02 KR KR1020007003984A patent/KR100566450B1/ko not_active IP Right Cessation
-
2001
- 2001-06-06 HK HK01103910A patent/HK1033304A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
KR100566450B1 (ko) | 2006-03-31 |
CN1276780A (zh) | 2000-12-13 |
EP1023261A1 (de) | 2000-08-02 |
BR9813052A (pt) | 2000-08-15 |
DE19745465A1 (de) | 1999-04-22 |
AU9748298A (en) | 1999-05-03 |
HK1033304A1 (en) | 2001-08-24 |
WO1999019292A1 (de) | 1999-04-22 |
CA2306935A1 (en) | 1999-04-22 |
DE59803298D1 (de) | 2002-04-11 |
EP1023261B1 (de) | 2002-03-06 |
KR20010015758A (ko) | 2001-02-26 |
TW443998B (en) | 2001-07-01 |
ES2174497T3 (es) | 2002-11-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: CARCOUSTICS TECHCONSULT GMBH Free format text: FORMER OWNER: BAYER AKTIENGESELLSCHAFT Effective date: 20120802 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20120802 Address after: Germany Leverkusen Patentee after: Carcoustics Techconsult GmbH Address before: Germany Leverkusen Patentee before: Bayer Aktiengesellschaft |
|
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20001213 Assignee: Bayer Material Science (China) Co., Ltd. Assignor: Carcoustics Techconsult GmbH Contract record no.: 2012990000854 Denomination of invention: Continuous method for producing aromatic amines Granted publication date: 20040908 License type: Common License Record date: 20121128 |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
C17 | Cessation of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20040908 Termination date: 20131002 |