JP2006508018A - アミンの製造方法 - Google Patents
アミンの製造方法 Download PDFInfo
- Publication number
- JP2006508018A JP2006508018A JP2003567859A JP2003567859A JP2006508018A JP 2006508018 A JP2006508018 A JP 2006508018A JP 2003567859 A JP2003567859 A JP 2003567859A JP 2003567859 A JP2003567859 A JP 2003567859A JP 2006508018 A JP2006508018 A JP 2006508018A
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- aromatic nitro
- hydrogen
- reaction mixture
- nitro compound
- 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.)
- Granted
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 aromatic nitro compounds Chemical class 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000011541 reaction mixture Substances 0.000 claims abstract description 26
- 239000007791 liquid phase Substances 0.000 claims abstract description 13
- 239000007858 starting material Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000005984 hydrogenation reaction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000009826 distribution Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000009849 deactivation Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
- BYFNZOKBMZKTSC-UHFFFAOYSA-N 1,3-dimethyl-5-nitrobenzene Chemical compound CC1=CC(C)=CC([N+]([O-])=O)=C1 BYFNZOKBMZKTSC-UHFFFAOYSA-N 0.000 description 1
- 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
- AVCSMMMOCOTIHF-UHFFFAOYSA-N 1,8-dinitronaphthalene Chemical compound C1=CC([N+]([O-])=O)=C2C([N+](=O)[O-])=CC=CC2=C1 AVCSMMMOCOTIHF-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- GJOVHPKYFFGKCY-UHFFFAOYSA-N 1-nitroethylbenzene Chemical compound [O-][N+](=O)C(C)C1=CC=CC=C1 GJOVHPKYFFGKCY-UHFFFAOYSA-N 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- XCSNRORTQRKCHB-UHFFFAOYSA-N 2-chloro-6-nitrotoluene Chemical compound CC1=C(Cl)C=CC=C1[N+]([O-])=O XCSNRORTQRKCHB-UHFFFAOYSA-N 0.000 description 1
- YADISKICBOYXFS-UHFFFAOYSA-N 2-ethyl-2-nitropropane-1,3-diol Chemical compound CCC(CO)(CO)[N+]([O-])=O YADISKICBOYXFS-UHFFFAOYSA-N 0.000 description 1
- MVGJRISPEUZYAQ-UHFFFAOYSA-N 2-methyl-2-nitropropan-1-ol Chemical compound OCC(C)(C)[N+]([O-])=O MVGJRISPEUZYAQ-UHFFFAOYSA-N 0.000 description 1
- MHIHRIPETCJEMQ-UHFFFAOYSA-N 2-nitrobutan-1-ol Chemical compound CCC(CO)[N+]([O-])=O MHIHRIPETCJEMQ-UHFFFAOYSA-N 0.000 description 1
- JLDYQKGOJLINHL-UHFFFAOYSA-N 2-nitroethenol Chemical compound OC=C[N+]([O-])=O JLDYQKGOJLINHL-UHFFFAOYSA-N 0.000 description 1
- ZJYJZEAJZXVAMF-UHFFFAOYSA-N 2-nitronaphthalene Chemical compound C1=CC=CC2=CC([N+](=O)[O-])=CC=C21 ZJYJZEAJZXVAMF-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- RUIFULUFLANOCI-UHFFFAOYSA-N 3,5-Dinitrotoluene Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 RUIFULUFLANOCI-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VMMLSJNPNVTYMN-UHFFFAOYSA-N dinitromethylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)C1=CC=CC=C1 VMMLSJNPNVTYMN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 150000004998 toluenediamines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
上部領域において下方向に向けられ、これを通じて反応混合物、及び所望により出発物質の一部が導入されるジェットノズルを有し、
反応装置のいずれかの部分に、これを通じて反応混合物が外部循環路で輸送装置によって再びジェットノズルへと輸送される流出口を有し、
下部領域において反転流を有し、そこでは使用される出発物質である水素及び/又は芳香族ニトロ化合物の少なくとも一部が、それらが液相中の上方に運ばれるように反応装置の液相へと供給される垂直反応装置中で、対応する芳香族ニトロ化合物を水素化することによりアミンを製造する。
Description
垂直反応装置の長さはその直径よりも大きく、
上部領域において下方向に向けられ、これを通じて反応混合物、及び所望により出発物質の一部が導入されるジェットノズルを有し、
反応装置のいずれかの部分に、これを通じて反応混合物が外部循環路で輸送装置によって再びジェットノズルへと輸送される流出口を有し、
その下部領域中に反転流を有し、その反転流において、使用される水素及び/又は芳香族ニトロ化合物の出発物質の少なくとも一部が反応装置の液相中へ、液体反応混合物中で上方向へ流れるように供給する方法を提供する。
ポンプ、ノズル、反応装置の下部部分にそらし板、同軸差込管を備えた外部循環路を設けた円筒状反応装置を使用した。反応装置の反応容積は、約12m3であった。反応装置は、350本の平行フィールド管(4)を設けられ、これは約300m2の冷却総面積に対応する。フィールド管に供給される冷却水の量は、250m3/hで有り、フィールド管に供給される冷却水の温度は50℃であった。
Claims (8)
- 当該アミンに対応する芳香族ニトロ化合物を垂直反応装置中で水素化することによりアミンを製造する方法であって、
該垂直反応装置は、
その長さがその直径よりも大きく、
上部領域において下方向に向けられ、これを通じて反応混合物、及び所望により出発物質の一部が導入されるジェットノズルを有し、
反応装置のいずれかの部分に、これを通じて反応混合物が外部循環路で輸送装置によって再びジェットノズルへと輸送される流出口を有し、
下部領域において反転流を有し、そこでは使用される出発物質である水素及び/又は芳香族ニトロ化合物の少なくとも一部が、それらが液相中の上方に運ばれるように反応装置の液相へと供給される、垂直反応装置である方法。 - 芳香族ニトロ化合物が反転流の上方に導入される、請求項1に記載の方法。
- 前記反応装置が、反応装置内の下部部分に反応装置の壁部に対して垂直に配設されたそらし板を有している、請求項1に記載の方法。
- 同軸差込管が、反応装置内に反応装置の壁部に対して平行に設置されている、請求項1又は請求項2に記載の方法。
- 芳香族ニトロ化合物をそらし板と差込管の間で反応装置に供給する、請求項1〜3のいずれかに記載の方法。
- 水素を反応装置の底部と差込管の間に供給する、請求項1〜4のいずれかに記載の方法。
- 使用される水素の一部を、反応装置の外部循環路に供給する、請求項1〜5のいずれかに記載の方法。
- 外部循環路において反応混合物が3〜15質量%の範囲の気体含有量を有するような量で、反応装置の外部循環路に水素を供給する、請求項1〜6のいずれかに記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10206214A DE10206214A1 (de) | 2002-02-15 | 2002-02-15 | Verfahren zur Herstellung von Aminen |
PCT/EP2003/001063 WO2003068724A1 (de) | 2002-02-15 | 2003-02-04 | Verfahren zur herstellung von aminen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006508018A true JP2006508018A (ja) | 2006-03-09 |
JP4146801B2 JP4146801B2 (ja) | 2008-09-10 |
Family
ID=27634960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003567859A Expired - Fee Related JP4146801B2 (ja) | 2002-02-15 | 2003-02-04 | アミンの製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7064237B2 (ja) |
EP (1) | EP1476418B1 (ja) |
JP (1) | JP4146801B2 (ja) |
KR (1) | KR100909409B1 (ja) |
CN (1) | CN1275933C (ja) |
AT (1) | ATE471926T1 (ja) |
AU (1) | AU2003208788A1 (ja) |
DE (2) | DE10206214A1 (ja) |
PT (1) | PT1476418E (ja) |
WO (1) | WO2003068724A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013530140A (ja) * | 2010-05-17 | 2013-07-25 | ビーエーエスエフ ソシエタス・ヨーロピア | ジニトロトルエンの水素化によるトリレンジアミンの製造方法 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7542454B2 (en) * | 2005-01-21 | 2009-06-02 | Intel Corporation | MIMO channel feedback protocols |
US7750188B2 (en) * | 2007-06-27 | 2010-07-06 | H R D Corporation | System and process for the production of aniline and toluenediamine |
US9150493B2 (en) | 2010-01-14 | 2015-10-06 | Bayer Intellectual Property Gmbh | Method for producing aromatic amines in the liquid phase |
US8981155B2 (en) | 2010-12-06 | 2015-03-17 | Basf Se | Process for preparing aromatic amines |
BR112013012865A2 (pt) | 2010-12-06 | 2016-09-06 | Basf Se | processo para preparar aminas aromáticas, método de regular a concentração de nitrocompostos e nitrosocompostos, e aparelho |
US8835688B2 (en) | 2011-03-16 | 2014-09-16 | Basf Se | Optimized introduction of the starting materials for a process for preparing aromatic amines by hydrogenation of nitroaromatics |
CN103534230B (zh) * | 2011-03-16 | 2015-06-03 | 巴斯夫欧洲公司 | 用于通过使硝基芳族化合物氢化来制备芳胺的方法的原料的优化引入 |
WO2012160072A1 (de) | 2011-05-24 | 2012-11-29 | Basf Se | Verfahren zur herstellung von polyisocyanaten aus biomasse |
US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
DE102011082441A1 (de) | 2011-09-09 | 2013-03-14 | Evonik Oxeno Gmbh | Strahlschlaufenreaktor mit Nanofiltration |
US8895783B2 (en) | 2012-02-07 | 2014-11-25 | Basf Se | Monitoring of the stoichiometric ratio in the reaction of nitroaromatics with hydrogen |
CN104302616B (zh) * | 2012-02-07 | 2016-05-11 | 巴斯夫欧洲公司 | 在硝基芳族化合物与氢反应过程中监测化学计量比的方法 |
EP3181220A1 (en) * | 2015-12-16 | 2017-06-21 | Basf Se | A process for removing a heterogeneous catalyst from a reaction product and a process for producing an aromatic amine |
CN109776332A (zh) * | 2019-02-22 | 2019-05-21 | 中海油天津化工研究设计院有限公司 | 一种连续式加氢制备2,4-二甲基苯胺的方法 |
CN114307862A (zh) * | 2021-12-01 | 2022-04-12 | 中海油天津化工研究设计院有限公司 | 一种膜分散加氢制备甲基取代苯胺的方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19844901C1 (de) * | 1998-09-30 | 1999-11-04 | Bayer Ag | Verfahren zur Dosierung von flüssigen Nitroaromaten mit mehr als einer Nitrogruppe in Reaktoren zur Sumpfphasen-Hydrierung |
WO2000035852A1 (de) * | 1998-12-12 | 2000-06-22 | Basf Aktiengesellschaft | Verfahren zur herstellung von aminen |
-
2002
- 2002-02-15 DE DE10206214A patent/DE10206214A1/de not_active Withdrawn
-
2003
- 2003-02-04 EP EP03706422A patent/EP1476418B1/de not_active Expired - Lifetime
- 2003-02-04 PT PT03706422T patent/PT1476418E/pt unknown
- 2003-02-04 DE DE50312829T patent/DE50312829D1/de not_active Expired - Lifetime
- 2003-02-04 US US10/502,779 patent/US7064237B2/en not_active Expired - Lifetime
- 2003-02-04 AT AT03706422T patent/ATE471926T1/de active
- 2003-02-04 JP JP2003567859A patent/JP4146801B2/ja not_active Expired - Fee Related
- 2003-02-04 CN CNB038039494A patent/CN1275933C/zh not_active Expired - Lifetime
- 2003-02-04 AU AU2003208788A patent/AU2003208788A1/en not_active Abandoned
- 2003-02-04 KR KR1020047012263A patent/KR100909409B1/ko not_active IP Right Cessation
- 2003-02-04 WO PCT/EP2003/001063 patent/WO2003068724A1/de active Application Filing
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013530140A (ja) * | 2010-05-17 | 2013-07-25 | ビーエーエスエフ ソシエタス・ヨーロピア | ジニトロトルエンの水素化によるトリレンジアミンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1476418A1 (de) | 2004-11-17 |
DE10206214A1 (de) | 2003-08-28 |
AU2003208788A1 (en) | 2003-09-04 |
KR100909409B1 (ko) | 2009-07-24 |
ATE471926T1 (de) | 2010-07-15 |
CN1275933C (zh) | 2006-09-20 |
CN1633408A (zh) | 2005-06-29 |
EP1476418B1 (de) | 2010-06-23 |
US7064237B2 (en) | 2006-06-20 |
WO2003068724A1 (de) | 2003-08-21 |
JP4146801B2 (ja) | 2008-09-10 |
DE50312829D1 (de) | 2010-08-05 |
KR20040091017A (ko) | 2004-10-27 |
US20050119505A1 (en) | 2005-06-02 |
PT1476418E (pt) | 2010-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100655354B1 (ko) | 아민의 제조 방법 | |
JP4146801B2 (ja) | アミンの製造方法 | |
TWI442971B (zh) | 氫化有機化合物之連續方法及反應器 | |
US9295971B2 (en) | Apparatus and process for the continuous reaction of liquids with gases | |
US9308515B2 (en) | Optimized introduction of the starting materials for a process for preparing aromatic amines by hydrogenation of nitroaromatics | |
US6894193B2 (en) | Method for hydrogenating liquid organic compounds | |
US7091383B2 (en) | Method for the production of amines | |
JP2016510322A (ja) | 液体と気体との連続反応のための装置及び方法 | |
CN106883128B (zh) | 从反应产物中去除非均相催化剂的方法和制备芳族胺的方法 | |
KR20140015473A (ko) | 니트로방향족의 수소화에 의해 방향족 아민을 제조하는 방법을 위한 반응물의 최적 계량 | |
US20140200351A1 (en) | Apparatus and process for the continuous reaction of liquids with gases | |
US9302237B2 (en) | Apparatus and process for the continuous reaction of liquids with gases | |
KR102688386B1 (ko) | 암모니아 첨가에 의한 니트로 화합물의 연속 수소화에서의 촉매 선택도 증가 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080522 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080620 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110627 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120627 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130627 Year of fee payment: 5 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |