Solid Catalyst Utilized Patents (Class 564/332)
  • Patent number: 8822726
    Abstract: The invention relates to a method for producing diaminodiphenyl alkanes, wherein an aromatic amine, which can be substituted or unsubstituted, is reacted with a C1-C3 aldehyde in the presence of a heterogeneous catalyst, said catalyst being a mesoporous acidic ion exchanger based on a divinylbenzene/styrene copolymer and the catalyst having acid centers in a concentration of 2 to 6 eq/kg measured according to DIN 54403 and the average pore diameter of the catalyst particles being 10 to 32 nm measured according to ASTM D 4222, and the content of polynuclear compounds in the reaction mixture being >10 and ˜15% by weight.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: September 2, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Manfred Kreczinski, Gerda Grund
  • Patent number: 8710267
    Abstract: The invention relates to a process for preparing methylenediphenyldiamine (MDA), comprising the following steps a) to c): a) converting formaldehyde and aniline to aminal b) removing water from the aminal obtained in step a) to establish a water content of 0 to 5% by weight based on the aminal, and c) adding an acidic catalyst to the aminal having a water content of 0 to 5% by weight, which comprises using formaldehyde in step a) in the form of highly concentrated formaldehyde with a CH2O content of >50% by weight and preparing the formaldehyde by oxidative dehydrogenation from methanol.
    Type: Grant
    Filed: April 19, 2010
    Date of Patent: April 29, 2014
    Assignee: BASF SE
    Inventors: Eckhard Stroefer, Kai Thiele, Michael Zoellinger, Johnny Moors, Jon S. Speier
  • Patent number: 8558027
    Abstract: The present disclosure relates to compositions, systems, and methods of forming an amine (e.g., methylenedianiline (MDA)) using an acid catalyst including, for example, a metal oxide-silica catalyst calcined at temperature(s) of about ?500° C. to form a solid acid silica-metal oxide catalyst. A metal oxide of a solid acid silica-metal oxide catalyst may comprise alumina. A process for making a solid acid silica-metal oxide catalyst may comprise calcining an amorphous alumina-silica material at temperature(s) of about ?500° C. and/or under an anhydrous and/or inert atmosphere. A rearrangement reaction of the condensation product of aniline and formaldehyde in the presence of a solid acid silica-metal oxide catalyst may yield more MDA and/or more desirable isomer(s) of MDA than reactions performed with a corresponding catalyst calcined at temperature(s) of less than 500° C.
    Type: Grant
    Filed: August 14, 2009
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies Inc.
    Inventors: Heiko Weiner, David C. Molzahn, Robert J. Gulotty, Jr.
  • Patent number: 8389770
    Abstract: The invention relates to a method for producing diaminodiphenyl alkanes, wherein an aromatic amine, which can be substituted or unsubstituted, is reacted with a C1-C3 aldehyde in the presence of a heterogeneous catalyst, said catalyst being a mesoporous acidic ion exchanger based on a divinylbenzene/styrene copolymer and the catalyst having acid centers in a concentration of 4 to 6 eq/kg as measured according to DIN 54 403 and the average pore diameter of the catalyst particles being 10 to 32 nm as measured according to ASTM D 4222 10, and the content of polynuclear compounds in the reaction mixture being ?10% by weight.
    Type: Grant
    Filed: March 26, 2009
    Date of Patent: March 5, 2013
    Assignee: Evonik Degussa GmbH
    Inventors: Gerda Grund, Manfred Kreczinski
  • Publication number: 20110144368
    Abstract: The present disclosure relates to compositions, systems, and methods of forming an amine (e.g., methylenedianiline (MDA)) using an acid catalyst including, for example, a metal oxide-silica catalyst calcined at temperature(s) of about ?500° C. to form a solid acid silica-metal oxide catalyst. A metal oxide of a solid acid silica-metal oxide catalyst may comprise alumina. A process for making a solid acid silica-metal oxide catalyst may comprise calcining an amorphous alumina-silica material at temperature(s) of about ?500° C. and/or under an anhydrous and/or inert atmosphere. A rearrangement reaction of the condensation product of aniline and formaldehyde in the presence of a solid acid silica-metal oxide catalyst may yield more MDA and/or more desirable isomer(s) of MDA than reactions performed with a corresponding catalyst calcined at temperature(s) of less than 500° C.
    Type: Application
    Filed: August 14, 2009
    Publication date: June 16, 2011
    Inventors: Heiko Weiner, David C. Molzahn, Robert J. Gulotty, JR.
  • Patent number: 7893301
    Abstract: The present invention provides a method of preparing polymethylene-polyphenyl-polyamine (briefly referred to as polyamine, DAM), in which a high gravity rotating bed is used as the mixing reactor of formaldehyde and aniline hydrochloride, the mixing solution of aniline hydrochloride and circulation solution and the formaldehyde are fed into the high gravity rotating bed reactor proportionally to carry out mixing and condensation reaction under a condition of a very high gravity; the materials leaving the high gravity rotating bed reactor is introduced into a stirred vessel to proceed with the pre-condensation reaction and obtain a condensation solution; and the process steps of heating, molecular rearrangement, neutralization, water washing and purification, etc. are completed to obtain the refined DAM.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: February 22, 2011
    Assignees: Ningbo Wanhua Polyurethanes Co., Ltd., Beijing University of Chemical Technology
    Inventors: Jiansheng Ding, Jianfeng Chen, Hongke Zhang, Haikui Zou, Weiqi Hua, Pengyuan Zhang, Shuchang Sun, Guangwen Chu, Limin Xu
  • Publication number: 20100317893
    Abstract: The invention relates to a method for producing diaminodiphenyl alkanes, wherein an aromatic amine, which can be substituted or unsubstituted, is reacted with a C1-C3 aldehyde in the presence of a heterogeneous catalyst, said catalyst being a mesoporous acidic ion exchanger based on a divinylbenzene/styrene copolymer and the catalyst having acid centers in a concentration of 2 to 6 eq/kg measured according to DIN 54 403 and the average pore diameter of the catalyst particles being 10 to 32 nm measured according to ASTM D 4222, and the content of polynuclear compounds in the reaction mixture being >10 and ?15% by weight.
    Type: Application
    Filed: March 10, 2009
    Publication date: December 16, 2010
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Manfred Kreczinski, Gerda Grund
  • Publication number: 20100312014
    Abstract: The invention relates to a method for producing diaminodiphenyl alkanes, wherein an aromatic amine, which can be substituted or unsubstituted, is reacted with a C1-C3 aldehyde in the presence of a heterogeneous catalyst, said catalyst being a mesoporous acidic ion exchanger based on a divinylbenzene/styrene copolymer and the catalyst having acid centers in a concentration of 4 to 6 eq/kg as measured according to DIN 54 403 and the average pore diameter of the catalyst particles being 10 to 32 nm as measured according to ASTM D 4222 10, and the content of polynuclear compounds in the reaction mixture being ?10% by weight.
    Type: Application
    Filed: March 26, 2009
    Publication date: December 9, 2010
    Applicant: Evonik Degussa GmbH
    Inventors: Gerda Grund, Manfred Kreczinski
  • Patent number: 7528283
    Abstract: The invention provides an improved process for preparing diamines and polyamines from the diphenylmethane series by reacting aniline and formaldehyde in the presence of an acid catalyst, the improvement involving the aniline containing less than about 3 wt. % of diamines and polyamines from the diphenylmethane series, based on the weight of the aniline.
    Type: Grant
    Filed: January 24, 2007
    Date of Patent: May 5, 2009
    Assignee: Bayer MeterialScience AG
    Inventors: Fritz Pohl, Jeffrey Bolton, Richard Adamson, Heinz-Herbert Muller, Rudolf Uchdorf
  • Patent number: 7435853
    Abstract: Di- and polyamines of the diphenylmethane series are produced by a) converting nitrobenzene and methanol in the presence of a catalyst to aniline, formaldehyde and carbon monoxide, and then b) converting the aniline and formaldehyde produced in step a) in the presence of an acid catalyst to di- and polyamines of the diphenylmethane series, and c) converting the carbon monoxide produced in step a) with chlorine to phosgene.
    Type: Grant
    Filed: February 9, 2006
    Date of Patent: October 14, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Stefan Grabowski, Markus Dugal, Aurel Wolf
  • Patent number: 7408083
    Abstract: A process is described for preparing diaminodiarylmethanes comprising the steps a) reacting an aromatic amine with a methylene-donating agent in the presence of homogeneous acid catalysts, b) removing the homogeneous acid catalyst from the reaction product, c) working up and purifying the reaction product, which comprises removing the homogeneous acid catalyst from the reaction mixture by adsorption to a solid adsorbent.
    Type: Grant
    Filed: June 25, 2004
    Date of Patent: August 5, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Steinbrenner, Eckhard Stroefer, Martin Sohn, Veronika Quaschning, Helmut Moehwald, Kai Thiele, Filip Deberdt, Jan D. Jacobs, Rolf Pinkos
  • Patent number: 7238840
    Abstract: Method of preparing diaminodiphenylmethane and higher homologues thereof from aniline and formaldehyde in the presence of heterogeneous solid acid catalysts selected from (a) delaminated zeolites and/or (b) metal silicate catalysts having an ordered mesoporous pore structure and/or (c) delaminated phyllosilicates.
    Type: Grant
    Filed: September 21, 2004
    Date of Patent: July 3, 2007
    Assignee: Huntsman International LLC
    Inventors: Pablo Botella Asuncion, Joris Karel Peter Bosman, Avelino Corma, Christopher John Mitchell
  • Patent number: 7105700
    Abstract: A process for preparing methane diphenyl diamine (MDA) or a mixture of methane diphenyl diamine (MDA) and its higher homologues with a controlled isomer distribution using a modified zeolite having “shape selectivity”. The mixture contains compounds having the following general formula (I): where R represents a hydrogen atom or a C1 to C8 (iso)alkyl group, a C4 to C10 cycloalkyl group or a C6 to C12 aromatic group and n is a whole number greater than or equal to one so as to give a functionality of 2 to 6.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: September 12, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Alberto De Angelis, Carlo Perego, Otello Farias, Aldo Bosetti
  • Patent number: 6936737
    Abstract: A process for preparing methane diphenyl diamine (MDA) or a mixture of methane diphenyl diamine (MDA) and its higher homologues with a controlled isomer distribution using a silanised zeolite have “shape selectivity”. The mixture contains compounds having the following general formula (I): where R represents a hydrogen atom or a C1 to C8 (iso) alkyl group, a C4 to C10 cycloalkyl group or a C6 to C12 aromatic group and n is a whole number greater than or equal to one so as to give a functionally of 2 to 6.
    Type: Grant
    Filed: September 7, 2001
    Date of Patent: August 30, 2005
    Assignee: Dow Global Technologies Inc.
    Inventors: Alberto De Angelis, Cristina Flego, Otello Farias, Aldo Bosetti
  • Patent number: 6846956
    Abstract: Described is a triarylmethane dye of the formula I where R1 and R2 are independently methyl, ethyl or hydroxyethyl, Q is substituted or unsubstituited phenyl or naphthyl and A? is the equivalent of an anion. It does not detach carcinogenic Michler's ketone.
    Type: Grant
    Filed: August 14, 2001
    Date of Patent: January 25, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Hellmut Kast, Thomas Gessner, Rainer Tresch
  • Patent number: 6818795
    Abstract: Process for the production of methylenedianiline and its higher homologous products which comprises reacting aniline, or one of its derivatives, and formaldehyde, or one of its precursors, in one or two reactors in the presence of a solid acid catalyst selected from a zeolite or a silico-alumina, distilling off the reaction water or the water added with the reagents.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: November 16, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Carlo Perego, Alberto De Angelis, Aldo Bosetti
  • Patent number: 6673970
    Abstract: Disclosed herein is a process for preparing a reaction product containing methylene diphenylamine, comprising reacting aniline and formaldehyde in the presence of an acid catalyst wherein the acid level of the resulting reaction mixture is reduced during digestion of the reaction mixture.
    Type: Grant
    Filed: December 29, 1999
    Date of Patent: January 6, 2004
    Assignee: Bayer Polymers LLC
    Inventors: Louis Renbaum, Mark S. Solomon, William D. Tippins
  • Patent number: 6649798
    Abstract: The present invention concerns a process for the production of methylenedianiline (MDA) having a high monomer content.
    Type: Grant
    Filed: August 7, 2002
    Date of Patent: November 18, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stephan Klein, Dirk Grotjohann, Christine Mendoza-Frohn, Daniel Koch, Heinz-Herbert Müller, Hans-Georg Pirkl, Rudolf Uchdorf, Gerhard Wegener
  • Patent number: 6610888
    Abstract: A method of reacting a solution comprising a mixture of chemical compounds which are in chemical equilibrium with one another with at least one further chemical compound (9) is provided. The method comprises the following steps: fractionation of the solution by means of a separation method to give at least two fractions (5, 6) which are enriched in different chemical compounds of the mixture; and reaction of a fraction (5) with the further chemical compound or compounds (9). The fractionation is advantageously carried out using a film evaporator (1). Unreacted fractions (6) can be recirculated via a residence time vessel (3) back to the fractionation step. The method is particularly suitable for reactions of an aqueous formaldehyde solution in which various components of the solution (formaldehyde, methylene glycol, polyoxymethylene glycols) react in different ways.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: August 26, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Ströfer, Stephan Scholl, Hans Hasse
  • Patent number: 6410789
    Abstract: In a process for preparing aromatic polyamine mixtures which contain compounds of the formula (I), H2N—A—CH2—B—NH2  (I) where A and B are 1,4-phenylene radicals each of which independently of one another can have 1 to 4 substituents selected from C1-20 alkyls and halogens, a compound of the formula (IV) H—A—NH—CH2—HN—B—H  (IV) and/or a compound of the formula (V) H—A—NH—CH2—B—NH2  (V) where A and B are substituted as above, are reacted at from 20° C. to 200° C.
    Type: Grant
    Filed: August 24, 1999
    Date of Patent: June 25, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Karsten Eller, Hans-Werner Langensiepen, Michael Hesse
  • Publication number: 20010056190
    Abstract: The invention relates to immobilized palladium complexes, to a process for their preparation, to their use as catalysts and to a process for the preparation of arylamines using immobilized palladium complexes.
    Type: Application
    Filed: May 21, 2001
    Publication date: December 27, 2001
    Inventors: Lukas Goossen, Martin Hendrix
  • Patent number: 5684180
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5679840
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5679841
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5675035
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5672737
    Abstract: The invention relates to a process for the fractionation and purification of mixtures of aromatic polyamines and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5663424
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648520
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648519
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5286760
    Abstract: Disclosed herein is a process for preparing a reaction product containing methylene diphenylamine comprising reacting aniline with an aldehyde, in the presence of a low level of an acid wherein the acid level is reduced before digesting reaction mixture at a high temperature which is sufficient to effect a rearrangement of the intermediates to produce a reaction product containing methylene diphenylamines and low levels of impurities.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: February 15, 1994
    Assignee: Miles, Inc.
    Inventors: Jeffrey S. Bolton, Robert L. Mayen
  • Patent number: 5241119
    Abstract: Process for the preparation of 4,4'-diaminodiphenylmethane and its derivatives.4,4'-diaminodiphenylmethane and its derivatives are prepared by the condensation of aniline, or its derivative, and aldehyde, or its precursor and/or isomerization of appropriate intermediate products. The reaction proceeds with zeolites acting as catalysts; these catalysts, which are selected in accordance with the reaction to be effected, are preferably zeolites based on Si, Al and B; Si, Al and Ti; Ti and Fe; ZSM-5; or Y zeolites.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: August 31, 1993
    Assignees: Eniricerche S.p.A., Enichem Synthesis S.p.A.
    Inventors: Mario G. Clerici, Giuseppe Bellussi, Ugo Romano
  • Patent number: 5047591
    Abstract: Bis-(amino-nitrophenyl)-methane can be produced in one stage with an approximately quantitative yield by condensing o-nitraniline and formaldehyde in water at a temperature of between 20.degree. and 40.degree. C. in the presence of sulfuric acid, and subsequently rearranging the formed methylene-bis-(o-nitraniline) by treatment of the reaction mixture at a temperature of between 90.degree. and 100.degree. C.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: September 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Werner Stegmann
  • Patent number: 4922019
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or an acyl group in which a non-aromatic hydrocarbon group of 1 to 6 carbon atoms is attached to the CO-group and R.sup.2 is H or NO.sub.2, if R.sup.1 is an acyl group, or is NO.sub.2, if R.sup.1 is hydrogen.
    Type: Grant
    Filed: June 29, 1988
    Date of Patent: May 1, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Lau, Gunter Siegemund
  • Patent number: 4554378
    Abstract: Polyamines are prepared from aromatic amines and aliphatic aldehydes or ketones using cationic or acid ion exchange resins as a catalyst in an essentially oxygen-free atmosphere with the aromatic amines being distilled and protected from the atmosphere.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: November 19, 1985
    Assignee: The Dow Chemical Company
    Inventors: John L. Nafziger, Laura A. Rader, Irwin J. Seward, Jr.
  • Patent number: 4294987
    Abstract: An improvement is described in the process of preparing polymethylene polyphenyl polyamines by condensing aniline and formaldehyde in the presence of an acid catalyst in the initial condensation. The improvement enables the amount of acid which has to be neutralized at the end of the reaction to be substantially reduced or eliminated entirely. This is accomplished without sacrifice of the high level of 4,4'-isomer of di(aminophenyl)methane normally present in the diamine content of the polyamines when a mineral acid catalyst is employed in the condensation.
    Type: Grant
    Filed: December 31, 1979
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventors: Richard A. Prather, Nirad N. Shah
  • Patent number: 4287364
    Abstract: Covers a method of preparing diaminodiphenylmethanes and higher homologues thereof which comprises the step of condensing aniline and formaldehyde in the presence of a molybdenum aluminide catalyst.
    Type: Grant
    Filed: September 24, 1980
    Date of Patent: September 1, 1981
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, Robert M. Gipson, Lewis W. Watts, Jr.
  • Patent number: 4286107
    Abstract: Covers a method of preparing diaminodiphenylmethanes and higher homologues thereof which comprises the step of condensing aniline and formaldehyde in the presence of a silver tungstate catalyst.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: August 25, 1981
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, Lewis W. Watts, Jr.
  • Patent number: 4284815
    Abstract: Covers a method of preparing diaminodiphenylmethanes and higher homologues thereof which comprises the step of condensing aniline and formaldehyde in the presence of a tungsten boride or sulfide catalyst.
    Type: Grant
    Filed: September 22, 1980
    Date of Patent: August 18, 1981
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, Lewis W. Watts, Jr., Robert M. Gipson
  • Patent number: 4284816
    Abstract: Covers a method of preparing diaminodiphenylmethanes and higher homologues thereof which comprises the step of condensing aniline and formaldehyde in the presence of a tungsten silicide catalyst.
    Type: Grant
    Filed: September 17, 1980
    Date of Patent: August 18, 1981
    Assignee: Texaco Inc.
    Inventors: Edward T. Marquis, Lewis W. Watts, Jr.