ES2106415T3 - Catalizador para fabricar bis-para-aminociclohexilmetano con una pequeña parte de trans-trans-isomero mediante hidrogenacion de dianilina de metileno. - Google Patents
Catalizador para fabricar bis-para-aminociclohexilmetano con una pequeña parte de trans-trans-isomero mediante hidrogenacion de dianilina de metileno.Info
- Publication number
- ES2106415T3 ES2106415T3 ES94109267T ES94109267T ES2106415T3 ES 2106415 T3 ES2106415 T3 ES 2106415T3 ES 94109267 T ES94109267 T ES 94109267T ES 94109267 T ES94109267 T ES 94109267T ES 2106415 T3 ES2106415 T3 ES 2106415T3
- Authority
- ES
- Spain
- Prior art keywords
- trans
- catalyst
- aminociclohexilmethane
- isomero
- para
- 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 - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title abstract 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 title 1
- 238000005984 hydrogenation reaction Methods 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000725 suspension Substances 0.000 abstract 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910001680 bayerite Inorganic materials 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
- C07C209/72—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines by reduction of six-membered aromatic rings
-
- 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
- B01J21/16—Clays or other mineral silicates
-
- 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
- B01J23/46—Ruthenium, rhodium, osmium or iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
LA INVENCION SE REFIERE A CATALIZADORES PARA LA ELABORACION DE BIS ION DE METILENDIANILINA, DONDE SE APLICA RUTENIO O RODIO EN UNA CANTIDAD DESDE 0,05 HASTA 8 % EN PESO, CON PREFERENCIA 0,2 HASTA 3 % EN PESO EN UN ESPESOR DE CAPA DESDE 5 HASTA 150 MICRAS, CON PREFERENCIA DESDE 10 HASTA 80 MICRAS, SOBRE UN SOPORTE, QUE SE COMPONE A PARTIR DE TIERRA ARCILLOSA DE TRANSICION CALCINADA Y REHIDRATADA SUPERFICIALMENTE. ESTA TIERRA ARCILLOSA EN SUSPENSION DE 10 G EN 300 ML DE AGUA EN 25 N. CONSIGUE AL MENOS CON EL MISMO PESO UN VALOR DE PH DE 8,2 Y DESPUES DE LA ADICION DE 10 ML 0,1 N ACIDO DE SAL A ESTA SUSPENSION DESPUES DE 30 MIN. RESULTA AL MENOS UN VALOR DE PH DE 6,0. LOS PORTADORES APROPIADOS ESPECIALES SE COMPONEN DE FORMA PREDOMINANTE A BASE DE HIDRARGILITA O BAYERITA. PARA LA OBTENCION DE LOS VALORES NECESARIOS EL SOPORTE PUEDE ESTAR PREVISTO CON UN RECUBRIMIENTO ADICIONAL. LA INVENCION DESCRIBE ADEMAS UN PROCEDIMIENTO PARA LA ELABORACION DEL CATALIZADOR, ASI COMO SU UTILIZACION.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4328007A DE4328007A1 (de) | 1993-08-20 | 1993-08-20 | Katalysator zur Herstellung von Bis-Para-aminocyclohexylmethan mit niedrigem Anteil an trans-trans-Isomer durch Hydrierung von Methylendiamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2106415T3 true ES2106415T3 (es) | 1997-11-01 |
Family
ID=6495617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES94109267T Expired - Lifetime ES2106415T3 (es) | 1993-08-20 | 1994-06-16 | Catalizador para fabricar bis-para-aminociclohexilmetano con una pequeña parte de trans-trans-isomero mediante hidrogenacion de dianilina de metileno. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5578546A (es) |
| EP (1) | EP0639403B1 (es) |
| JP (1) | JP3483625B2 (es) |
| DE (2) | DE4328007A1 (es) |
| ES (1) | ES2106415T3 (es) |
| ZA (1) | ZA946297B (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6409939B1 (en) * | 2000-05-31 | 2002-06-25 | Uop Llc | Method for producing a hydrogen-rich fuel stream |
| DE10119135A1 (de) | 2001-04-19 | 2002-10-24 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Diaminodicyclohexylmethan |
| ES2322033T3 (es) | 2002-05-31 | 2009-06-16 | Evonik Degussa Gmbh | Catalizador de rutenio soportado y procedimiento para la hidrogenacion de una amina aromatica en presencia de este catalizador. |
| DE10225565A1 (de) * | 2002-06-10 | 2003-12-18 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| DE10231119A1 (de) * | 2002-07-10 | 2004-02-05 | Degussa Ag | Verfahren zur Selektivitätserhöhung der Hydrierung von 4,4'-Diaminodiphenylmethan zu 4,4'-Diaminodicyclohexylmethan in Gegenwart eines N-Alkyl-4,4'-Diaminodiphenylmethans |
| US7038088B2 (en) * | 2004-05-19 | 2006-05-02 | Air Products And Chemicals, Inc. | Hydrogenation of highly contaminated methylenedianiline |
| US7737077B2 (en) * | 2004-11-25 | 2010-06-15 | Cataler Corporation | Catalyst for purifying exhaust gases |
| US7304183B2 (en) * | 2004-12-16 | 2007-12-04 | Huntsman Petrochemical Corporation | Co-production of cyclohexylamine and bis(para-aminocyclohexyl) methane |
| DE102004063673A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur kontinuierlichen katalytischen Hydrierung von hydrierbaren Verbindungen an festen, im Festbett angeordneten Katalysatoren mit einem wasserstoffhaltigen Gas |
| DE102005029200A1 (de) * | 2005-06-22 | 2006-12-28 | Basf Ag | Katalysator und Verfahren zur Hydrierung von hydrierbare Gruppen enthaltenden organischen Verbindungen |
| JP2008200614A (ja) * | 2007-02-21 | 2008-09-04 | Matsushita Electric Ind Co Ltd | 一酸化炭素酸化触媒およびその製造方法、水素生成装置、ならびに燃料電池システム |
| DE102008002002A1 (de) | 2008-05-27 | 2009-12-03 | Evonik Degussa Gmbh | Chlor armes mehrstufiges Verfahren zur Herstellung von cycloaliphatischen Diisocyanaten |
| TWI534131B (zh) | 2014-11-27 | 2016-05-21 | 財團法人工業技術研究院 | 氫化4,4’-二胺基二苯甲烷的觸媒與方法 |
| CN113929584B (zh) * | 2021-11-22 | 2024-12-03 | 江苏清泉化学股份有限公司 | 一种合成4,4,-二氨基二环己基甲烷的方法 |
| EP4685129A1 (de) | 2024-07-26 | 2026-01-28 | Evonik Operations GmbH | Verfahren zur hydrierung von mda |
| EP4685133A1 (de) | 2024-07-26 | 2026-01-28 | Evonik Operations GmbH | Verfahren zur kontinuierlichen, katalytischen hydrierung von mda |
| EP4684871A1 (de) | 2024-07-26 | 2026-01-28 | Evonik Operations GmbH | Verfahren zur kontinuierlichen, katalytischen hydrierung von mda |
| EP4685131A1 (de) | 2024-07-26 | 2026-01-28 | Evonik Operations GmbH | Verfahren zur kontinuierlichen, katalytischen hydrierung von mda |
| EP4685132A1 (de) | 2024-07-26 | 2026-01-28 | Evonik Operations GmbH | Verfahren zur kontinuierlichen, katalytischen hydrierung von mda |
| EP4685130A1 (de) | 2024-07-26 | 2026-01-28 | Evonik Operations GmbH | Verfahren zur herstellung von methylenbis(cyclohexylamin) |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2606928A (en) * | 1947-11-18 | 1952-08-12 | Du Pont | Preparation of amino alicyclic compounds |
| US2511028A (en) * | 1947-12-04 | 1950-06-13 | Du Pont | 4-[(para-aminophenyl) alkyl] cyclo-hexylamine |
| US2606925A (en) * | 1949-12-15 | 1952-08-12 | Du Pont | Ruthenium catalyzed hydrogenation process for obtaining aminocyclohexyl compounds |
| US3347917A (en) * | 1961-12-29 | 1967-10-17 | Du Pont | Process for the preparation of di (paraaminocyclohexyl) methane |
| US3636108A (en) * | 1965-12-23 | 1972-01-18 | Du Pont | Catalytic hydrogenation of aromatic nitrogen containing compounds over alkali moderated ruthenium |
| US3591635A (en) * | 1968-09-25 | 1971-07-06 | Upjohn Co | Catalytic hydrogenation process for preparing di(4 - aminocyclohexyl) methane |
| US3644522A (en) * | 1969-04-04 | 1972-02-22 | Du Pont | Catalytic hydrogenation of nitrogen containing compounds over supported ruthenium catalysts |
| US3697449A (en) * | 1970-12-14 | 1972-10-10 | Du Pont | Alkali moderation of supported ruthenium catalysts |
| US3856862A (en) * | 1973-06-25 | 1974-12-24 | Upjohn Co | Process for hydrogenation of di(4-aminophenyl)methane with a rhodium catalyst |
| US3959374A (en) * | 1974-05-30 | 1976-05-25 | Jefferson Chemical Company, Inc. | Process for the preparation of mixed isomeric methylene-bridged polycyclohexylpolyamines |
| US4051072A (en) * | 1976-04-05 | 1977-09-27 | General Motors Corporation | Method for making pellet type catalyst |
| CA1109856A (en) * | 1976-06-14 | 1981-09-29 | Robert H. Ebel | Hydrodesulfurization catalysts based on supports prepared from rehydratable alumina |
| DE2745172A1 (de) * | 1977-10-07 | 1979-04-12 | Bayer Ag | Ruthenium-traegerkatalysator |
| US4166100A (en) * | 1978-05-26 | 1979-08-28 | Andrushkevich Mikhail M | Method of preparing granulated activated alumina |
| US4394298A (en) * | 1980-01-10 | 1983-07-19 | Phillips Petroleum Company | Hydrogenation catalyst |
| CA1204785A (en) * | 1981-06-01 | 1986-05-20 | Gary F. Allen | Process for the catalytic hydrogenation of di (4- aminophenyl) methane |
| US4380510A (en) * | 1981-11-04 | 1983-04-19 | General Motors Corporation | Method of making layered catalysts |
| US4448995A (en) * | 1982-12-13 | 1984-05-15 | Mobay Chemical Corporation | Catalytic hydrogenation of di(4-aminophenyl)methane |
| EP0121735A1 (en) * | 1983-03-16 | 1984-10-17 | American Cyanamid Company | Reforming catalysts having support prepared from rehydratable alumina |
| US4513101A (en) * | 1983-07-27 | 1985-04-23 | W. R. Grace & Co. | Small bead auto exhaust catalyst |
| US4754070A (en) * | 1986-01-23 | 1988-06-28 | Air Products And Chemicals, Inc. | Hydrogenation of methylenedianiline to produce bis(para-aminocyclohexyl)methane |
| EP0324190B1 (en) * | 1988-01-14 | 1993-05-12 | Hüls Aktiengesellschaft | Process for the production of 4,4'-diamino-dicyclohexylmethane with a low trans-trans isomer content by the catalytic hydrogenation of 4,4'-diaminodiphenylmethane |
| US5026914A (en) * | 1989-04-11 | 1991-06-25 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines using rhodium on titania or zirconia support |
| DE4028270A1 (de) * | 1990-09-06 | 1992-03-12 | Bayer Ag | Verfahren zur herstellung von di-(4-aminocyclohexyl)-methan mit einem anteil an 15 bis 25 gew.-% des trans-trans-isomeren |
| US5360934A (en) * | 1993-06-25 | 1994-11-01 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
-
1993
- 1993-08-20 DE DE4328007A patent/DE4328007A1/de not_active Withdrawn
-
1994
- 1994-06-16 DE DE59403525T patent/DE59403525D1/de not_active Expired - Lifetime
- 1994-06-16 ES ES94109267T patent/ES2106415T3/es not_active Expired - Lifetime
- 1994-06-16 EP EP94109267A patent/EP0639403B1/de not_active Expired - Lifetime
- 1994-08-04 US US08/285,527 patent/US5578546A/en not_active Expired - Lifetime
- 1994-08-18 JP JP19428094A patent/JP3483625B2/ja not_active Expired - Fee Related
- 1994-08-19 ZA ZA946297A patent/ZA946297B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA946297B (en) | 1995-03-23 |
| DE59403525D1 (de) | 1997-09-04 |
| DE4328007A1 (de) | 1995-02-23 |
| EP0639403B1 (de) | 1997-07-30 |
| US5578546A (en) | 1996-11-26 |
| EP0639403A3 (de) | 1995-05-17 |
| JPH0780305A (ja) | 1995-03-28 |
| JP3483625B2 (ja) | 2004-01-06 |
| EP0639403A2 (de) | 1995-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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