Processes For Forming The Isocyanate Group Patents (Class 560/338)
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Patent number: 12049437Abstract: The diisocyanate composition according to an embodiment of the present invention comprises, in the composition, a benzyl isocyanate having a methyl group in an amount of 5 ppm to 200 ppm, an aromatic compound having a halogen group in an amount of 5 ppm to 1,000 ppm, a benzyl isocyanate having an ethyl group in an amount of 1 ppm to 1,000 ppm, or a combination thereof. It is possible to improve the optical characteristics by preventing the occurrence of yellowing, striae, and cloudiness and to enhance the mechanical properties such as impact resistance at the same time. Thus, it can be advantageously used to prepare an optical material of high quality.Type: GrantFiled: December 4, 2020Date of Patent: July 30, 2024Assignees: SK PUCORE CO., LTD., WOORI FINE CHEM CO., LTD.Inventors: Jaeyoung Pai, Jeongmoo Kim, Hyuk Hee Han, Jung Hwan Myung, Myung-Ok Kyun, Jooyoung Jung
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Patent number: 9006480Abstract: The invention relates a process for producing isocyanates comprising the steps of a) providing an azolide and optionally a solvent, and b) adding an acid at a temperature below about 40 C. The invention also relates to the isocyanate obtainable by such a process.Type: GrantFiled: April 4, 2011Date of Patent: April 14, 2015Assignee: 3M Innovative Properties CompanyInventors: Wolf Steiger, Peter Bissinger
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Patent number: 8981145Abstract: The invention relates to a process for preparing isocyanates, comprising (a) the reaction of at least one amine with phosgene in the gas phase in a reaction zone and (b) the subsequent cooling of the reaction gases in a cooling zone by means of indirect cooling, the cooling medium which absorbs the heat of the reaction gases being conducted in countercurrent to the product stream at least in the region of the highest temperature in the cooling zone.Type: GrantFiled: March 17, 2011Date of Patent: March 17, 2015Assignee: BASF SEInventors: Vanessa Simone Lehr, Torsten Mattke
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Patent number: 8921594Abstract: A process for phosgenating an amine comprising employing a plug-flow type reactor with internal recycle is disclosed. The process can be continuous, which makes it possible to prepare, in a single stage, a (poly)isocyanate with a good yield, without formation of byproducts and on simplifying the plant in order to carry out the process so as to promote safety.Type: GrantFiled: December 18, 2009Date of Patent: December 30, 2014Assignee: Vencorex FranceInventors: Nicolas Perret, Denis Revelant
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Patent number: 8895774Abstract: An object of the present invention is to provide a process that enables isocyanate to be produced stably over a long period of time and at high yield without encountering problems of the prior art during production of isocyanate without using phosgene.Type: GrantFiled: May 15, 2008Date of Patent: November 25, 2014Assignee: Asahi Kasei Chemicals CorporationInventors: Masaaki Shinohata, Nobuhisa Miyake
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Patent number: 8871969Abstract: The invention provides a multistage process for continuously preparing organic polyisocyanates, preferably diisocyanates, more preferably aliphatic or cycloaliphatic diisocyanates, by reaction of the corresponding organic polyamines with carbonic acid derivatives and alcohols into monomeric polyurethanes of low molecular mass, and the dissociation of said polyurethanes. The invention further provides an associated preparation process in which at certain reaction stages the polyisocyanates prepared and unutilizable residues are removed and reusable by-products and intermediates are recycled to preliminary stages.Type: GrantFiled: May 30, 2012Date of Patent: October 28, 2014Assignee: BASF SEInventors: Torsten Mattke, Matthias Klötzer, Robert Baumann
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Patent number: 8853443Abstract: The present invention relates to a process for preparing an isocyanate, comprising hydrogenating a mixture (Gi) comprising an amine in the presence of a hydrogenation catalyst comprising copper to obtain a mixture (Gii) comprising the amine, and reacting the mixture (Gii) with phosgene to obtain a mixture (Giii) comprising the isocyanate. The present invention further relates to the isocyanate preparable by this process.Type: GrantFiled: November 18, 2009Date of Patent: October 7, 2014Assignee: BASF SEInventors: Daniel Breuninger, Johannes Adam, Heiner Schelling, Eckhard Stroefer, Markus Kraemer, Matthias Eiermann, Kai Thiele, Michael Zoellinger, Rolf Pinkos
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Patent number: 8835673Abstract: Process for preparing aromatic isocyanates by reacting the corresponding formamides with an oxygen-comprising gas over noble metal catalysts at temperatures of from 300 to 600° C. and a contact time of from 1 to 1000 ms, wherein: a. the formamide is vaporized before entering the reaction zone, b. the reaction mixture obtained is quenched with an alcohol-comprising quenching liquid and c. the urethane formed is dissociated into isocyanate and alcohol.Type: GrantFiled: December 3, 2010Date of Patent: September 16, 2014Assignee: BASF SEInventors: Torsten Mattke, Eckhard Stroefer, Julia Leschinski, Radwan Abdallah, Axel Franzke, Michael Bock
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Patent number: 8809574Abstract: The present invention discloses a method for preparing isocyanates by liquid-phase catalytic thermal cracking. In this method, in a reaction-rectification thermal cracking reactor, using a catalyst composition comprising a superfine powder metal oxide catalyst and an ionic liquid, an alkyl or aryl dialkylurethane, or multialkylurethane being a reactant is liquid-phase thermal cracked for a reaction time of 0.5-3 h under a reaction temperature of 160-220° C. and an absolute pressure of 1000-8000 Pa so as to prepare the corresponding isocyanate. The invention has the characteristics of low thermal cracking temperature, high yield of target products, relatively simple reaction apparatus and good universality for substrates (the yields of HDI, MDI, TDI, HMDI, NDI and IPDI or the like are all>85%) and the like.Type: GrantFiled: December 14, 2009Date of Patent: August 19, 2014Assignee: Lanzhou Institute of Chemical Physics, Chinese Academy of SciencesInventors: Youquan Deng, Xiaoguang Guo, Feng Shi, Qinghua Zhang, Xiangyuan Ma, Liujin Lu, Jian Li, Xiong Tian, Yubo Ma, Jianpeng Shang, Xinjiang Cui, Liguo L Wang, Hongzhe Zhang
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Patent number: 8802890Abstract: The present invention relates to a process for manufacturing isocyanates from an amine compound. The process comprises the steps of a) Providing chlorine; b) Providing carbon monoxide; c) Reacting said chlorine and said carbon monoxide for providing phosgene, the carbon monoxide being provided in an adjustable molar excess; d) Providing an amine compound and phosgenating said amine compound using said phosgene thereby providing said isocyanate; the process further comprises adjusting said adjustable molar excess, i.e. the molar excess of carbon monoxide, for adjusting the color of the isocyanate.Type: GrantFiled: November 5, 2009Date of Patent: August 12, 2014Assignee: Huntsman International LLCInventors: Robert Henry Carr, Johannes Lodewijk Koole, Udo Brian Dave Mike Rodger Bruinsma
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Patent number: 8759568Abstract: The invention relates to a process for preparing isocyanates by reacting the corresponding amines with phosgene, optionally in the presence of an inert medium, in which phosgene and amine are first mixed and converted to the isocyanate in a reactor, and in which a reaction gas which comprises isocyanate and hydrogen chloride leaving the reactor is cooled in a quench by adding a liquid quench medium to form a mixture of reaction gas and quench medium as the product stream. The walls of the quench are essentially completely wetted with a liquid.Type: GrantFiled: April 7, 2010Date of Patent: June 24, 2014Assignee: BASF SEInventors: Vanessa Simone Lehr, Carsten Knoesche, Torsten Mattke
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Patent number: 8680323Abstract: The invention relates to a process for preparing isocyanates by thermal dissociation of carbamates and separation by distillation of the reaction mixture from the carbamate dissociation, comprising the corresponding isocyanate and the corresponding alcohol, by distillation in a column (K) having an enrichment section (V) and a stripping section (A), where the carbamate (1) is introduced between the enrichment section (V) and the stripping section (A) and the isocyanate is taken off as a constituent of the bottom stream (2) and the alcohol is taken off as a constituent of the overhead stream (3) from the column (K), in the presence of an inert solvent, wherein an intermediate boiler having a boiling point between the boiling point of the isocyanate and the boiling point of the alcohol under the operating conditions of the carbamate dissociation is used as inert solvent and is fed as external runback (4) in liquid form in a purity of >95% by weight, based on the total weight of the external runback (4), in tType: GrantFiled: January 18, 2011Date of Patent: March 25, 2014Assignee: BASF SEInventors: Michael Bock, Axel Franzke, Robert Baumann, Eckhard Stroefer
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Publication number: 20130303740Abstract: The invention relates to a method for producing urethanes or ureas or mixtures of urethanes and ureas by oxidative carbonylation of organic amines in the presence of carbon monoxide, oxygen and a catalyst, where the catalyst used is a transition metal complex containing the structural feature: [Mn+(O˜N˜O)2?](n-2)+(L)m(Z?)n-2 and the method is carried out under halogen-free reaction conditions. The invention further relates to transition metal complexes containing said structural feature and also to the use of such transition metal complexes as catalysts in the production of urethanes or ureas or mixtures of urethanes and ureas.Type: ApplicationFiled: August 9, 2011Publication date: November 14, 2013Applicant: Bayer Intellectual Property GmbHInventors: Felix Gärtner, Andreas Jacob, Jörg Sundermeyer, Stephan Klein, Stefan Wershofen
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Patent number: 8552217Abstract: The present invention encompasses the finding that improvements can be achieved in manufacture of isocyanates through the use of a substitute for or a precursor of phosgene. Methods and compositions utilized in accordance with the present invention can be useful in situations in which it is difficult to use phosgene, and in particular gaseous phosgene. In some embodiments, a substitute for or a precursor of phosgene used in accordance with the present invention for preparing isocyanates is or comprises diphosgene (ClCO2CCl3).Type: GrantFiled: February 4, 2011Date of Patent: October 8, 2013Assignee: Warsaw Orthopedic, Inc.Inventors: Subha Bhattacharyya, Scott Guelcher, Damodaragounder Gopal, Marco Burello
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Patent number: 8546605Abstract: The invention provides a multistage process for continuously preparing organic, distillable polyisocyanates, preferably diisocyanates, more preferably aliphatic or cycloaliphatic diisocyanates, by reacting the corresponding organic polyamines with carbonic acid derivatives and alcohols to low molecular mass monomeric polyurethanes, and thermally cleaving said polyurethanes, in which at defined reaction stages the polyisocyanates prepared and unusable residues are separated off, and reusable by products and intermediates are recycled to upstream stages.Type: GrantFiled: September 5, 2006Date of Patent: October 1, 2013Assignee: BASF AktiengesellschaftInventors: Matthias Kloetzer, Eckhard Stroefer, Volker Krase, Andreas Schmidt, Peter Scherbel
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Patent number: 8536370Abstract: Low chlorine, multi-staged method for producing cycloaliphatic diisocyanates. The invention relates to a multi-staged method for the continuous low-chlorine production of cycloaliphatic diisocyanates, comprising the synthesis of diaminodipheynl alkanes, the hydration thereof into the corresponding cycloaliphatic diamines and the subsequent conversion of cycloaliphatic diamines to the corresponding cycloalkylene biscarbamates and the thermal cleaving of the latter into the cycloaliphatic diisocyanates and alcohol.Type: GrantFiled: May 18, 2009Date of Patent: September 17, 2013Assignee: Evonik Degussa GmbHInventors: Gerda Grund, Manfred Kreczinski, Stephan Kohlstruk, Christian Lettmann
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Patent number: 8487127Abstract: The invention relates to a process for preparing isocyanates by reacting the corresponding amines with phosgene in the gas phase, in the presence or absence of an inert medium, which comprises the following steps: (a) vaporization of the amine in a vaporizer, (b) superheating of the amine, (c) mixing of the gaseous amine with the phosgene and introduction into a reaction zone, (d) reaction of amine and phosgene to give isocyanate in the reaction zone, with a reaction mixture comprising isocyanate and hydrogen chloride being formed, (e) cooling of the reaction mixture comprising isocyanate and hydrogen chloride, wherein the vaporizer comprises a vessel in which tubes through which a heating medium flows are comprised, where number and diameter of the tubes are designed so that the tubes have a specific heat transfer area based on the volume through which the amine flows of at least 300 m2/m3.Type: GrantFiled: February 25, 2011Date of Patent: July 16, 2013Assignee: BASF SEInventors: Torsten Mattke, Ralf Boehling, Carsten Knoesche, Vanessa Simone Lehr
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Patent number: 8293937Abstract: The invention relates to a new industrial process for producing low-monomer-content organic polyisocyanates by oligomerization of organic diisocyanates in a two-phase system.Type: GrantFiled: December 15, 2008Date of Patent: October 23, 2012Assignee: Bayer MaterialScience AG.Inventors: Martin Brahm, Frank Richter, Thomas Voigt, Reinhard Halpaap
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Publication number: 20120253063Abstract: Process for preparing aromatic isocyanates by reacting the corresponding formamides with an oxygen-comprising gas over noble metal catalysts at temperatures of from 300 to 600° C. and a contact time of from 1 to 1000 ms, wherein: a. the formamide is vaporized before entering the reaction zone, b. the reaction mixture obtained is quenched with an alcohol-comprising quenching liquid and c. the urethane formed is dissociated into isocyanate and alcohol.Type: ApplicationFiled: December 3, 2010Publication date: October 4, 2012Applicant: BASF SEInventors: Torsten Mattke, Eckhard Stroefer, Julia Leschinski, Radwan Abdallah, Axel Franzke, Michael Bock
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Patent number: 8258337Abstract: The present invention relates to a process for preparing isocyanates and an apparatus suitable for this purpose, and also its use. In the process, an amine and phosgene, both in the gas phase, react in the presence of an inert medium. A number, n, of amine streams are reacted with a number, n +1, of phosgene streams in a reactor. The number n is a positive integer of at least 1. All amine and phosgene streams are introduced into the reactor through annular gaps for mixing.Type: GrantFiled: August 23, 2006Date of Patent: September 4, 2012Assignee: BASF AktiengesellschaftInventors: Andreas Woelfert, Carsten Knoesche, Andreas Daiss, Tsung-Chieh Cheng, Torsten Mattke, Eckhard Stroefer
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Publication number: 20120178942Abstract: Processes useful for the preparation of a Compound of Formula I: Formula (I). Intermediates useful for the preparation of the compound of Formula I, and processes useful for preparing said intermediates are disclosed.Type: ApplicationFiled: July 27, 2010Publication date: July 12, 2012Inventors: John Traverse, William M. Leong, Steven P. Miller, Jennifer Albaneze-Walker, Thomas J. Hunter, Lijun Wang, Hongbiao Liao, Ashok Arasappan, Scott T. Trzaska, Randi M. Smith, Azzeddine Lekhal, Stephane L. Bogen, Jianshe Kong, Frank Bennett, F. George Njoroge, Marc Poirier, Shen-Chun Kuo, Yonggang Chen, Kenneth S. Matthews, Patrice Demonchaux, Amadeo Ferreira
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Patent number: 8153838Abstract: An isocyanate is produced by: (a) reacting chlorine with carbon monoxide to form phosgene, (b) reacting the phosgene with an organic amine to form an isocyanate and hydrogen chloride, (c) separating the isocyanate and hydrogen chloride, (d) optionally, purifying the hydrogen chloride, (e) preparing an aqueous solution of the hydrogen chloride, (f) optionally, purifying the aqueous solution of hydrogen chloride, (g) subjecting the aqueous hydrogen chloride solution to electrochemical oxidation to form chlorine, and (h) returning at least a portion of the chlorine produced in (g) to (a).Type: GrantFiled: June 30, 2008Date of Patent: April 10, 2012Assignee: Bayer MaterialScience AGInventors: Andreas Bulan, Rainer Weber, Wolfgang Lorenz, Gerhard Moormann, Friedhelm Kämper, Berthold Keggenhoff
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Publication number: 20120016154Abstract: The invention relates to a process for preparing isocyanates by reacting the corresponding amines with phosgene in the gas phase, if appropriate in the presence of an inert medium, in which the amine and the phosgene are first mixed and converted to the isocyanate in a reactor, and in which a reaction gas which comprises isocyanate and hydrogen chloride and leaves the reactor is cooled in a quench space of a quench by adding a quench medium. The quench medium on addition to the quench space has a temperature above the condensation temperature or the desublimation temperature of the reaction gas.Type: ApplicationFiled: October 8, 2009Publication date: January 19, 2012Applicant: BASF SEInventors: Torsten Mattke, Carsten Knoesche
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Patent number: 8044235Abstract: A monomer is provided which is excellent in reactivity, can give high heat resistance and high refractive index, and has two or more polymerizable functional groups with different polymerization properties and an aromatic ring in the molecule. An industrial advantageous process for producing the monomer is also provided. The monomer is an aromatic isocyanate compound containing a (meth)acryloyl group, and is represented by Formula (I): wherein R1 is a single bond or a linear or branched alkylene group of 1 to 5 carbon atoms, R2 is a hydrogen atom or a methyl group, R3 is a single bond or a linear or branched alkylene group of 1 to 3 carbon atoms, X is independently a halogen atom or an electron-withdrawing group, m is an integer ranging from 0 to 4, n is an integer ranging from 1 to 3, and 1?m+n?5.Type: GrantFiled: March 15, 2006Date of Patent: October 25, 2011Assignee: Showa Denko K.K.Inventors: Kaneo Nozawa, Katsutoshi Ohno, Yotaro Hattori
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Patent number: 8026387Abstract: The present invention relates to a multiple-stage process for the continuous preparation of organic, distillable polyisocyanates, preferably diisocyanates, more preferably aliphatic or cycloaliphatic diisocyanates, by reaction of the corresponding organic poly-amines with ureas to form low-molecular monomeric polyureas, and the thermal decomposition thereof.Type: GrantFiled: January 9, 2007Date of Patent: September 27, 2011Assignee: BASF AktiengesellschaftInventors: Matthias Kloetzer, Eckhard Stroefer, Heinrich-Josef Blankertz
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Patent number: 7977504Abstract: An object of the present invention is to provide a process for producing isocyanates, which are industrially useful compounds, without using phosgene, and to provide a process for chemically recycling waste polycarbonate resin. The present invention discloses a process enabling isocyanate compounds to be produced without using phosgene as a raw material by subjecting a carbamic acid ester compound obtained by a reaction between an aromatic polycarbonate resin and an amine compound to a thermal decomposition reaction, while at the same time disclosing a process enabling chemical recycling of aromatic polycarbonate resin by recovering a divalent aromatic hydroxy compound forming aromatic polycarbonates.Type: GrantFiled: November 14, 2008Date of Patent: July 12, 2011Assignee: Asahi Kasei Chemicals CorporationInventors: Masaaki Shinohata, Nobuhisa Miyake
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Publication number: 20110028755Abstract: Low chlorine, multi-staged method for producing cycloaliphatic diisocyanates. The invention relates to a multi-staged method for the continuous low-chlorine production of cycloaliphatic diisocyanates, comprising the synthesis of diaminodipheynl alkanes, the hydration thereof into the corresponding cycloaliphatic diamines and the subsequent conversion of cycloaliphatic diamines to the corresponding cycloalkylene biscarbamates and the thermal cleaving of the latter into the cycloaliphatic diisocyanates and alcohol.Type: ApplicationFiled: May 18, 2009Publication date: February 3, 2011Applicant: EVONIK DEGUSSA GmbHInventors: Gerda Grund, Manfred Kreczinski, Stephan Kohlstruk, Christian Lettmann
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Publication number: 20110021810Abstract: The present invention discloses a method for preparing isocyanates by liquid-phase catalytic thermal cracking. In this method, in a reaction-rectification thermal cracking reactor, using a catalyst composition comprising a superfine powder metal oxide catalyst and an ionic liquid, an alkyl or aryl dialkylurethane, or multialkylurethane being a reactant is liquid-phase thermal cracked for a reaction time of 0.5-3 h under a reaction temperature of 160-220° C. and an absolute pressure of 1000-8000 Pa so as to prepare the corresponding isocyanate. The invention has the characteristics of low thermal cracking temperature, high yield of target products, relatively simple reaction apparatus and good universality for substrates (the yields of HDI, MDI, TDI, HMDI, NDI and IPDI or the like are all >85%) and the like.Type: ApplicationFiled: December 14, 2009Publication date: January 27, 2011Applicant: LANZHOU INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Youquan DENG, Xiaoguang GUO, Feng SHI, Qinghua ZHANG, Xiangyuan MA, Liujin LU, Jian LI, Xiong TIAN, Yubo MA, Jianpeng SHANG, Xinjiang CUI, Liguo L. WANG, Hongzhe ZHANG
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Publication number: 20100185011Abstract: The present invention relates to a process for preparing mixtures of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates by sequential reaction of benzene to nitrobenzene to aniline to polyphenyl polymethylene polyamines to polyphenyl polymethylene polyisocyanates wherein the benzene used as the starting material contains 500 to 5000 ppm w/w toluene and/or xylenes.Type: ApplicationFiled: April 25, 2008Publication date: July 22, 2010Applicant: Huntsman International LLCInventors: Robert Carr, Nicolaas Van Wiechen
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Publication number: 20100113819Abstract: The present invention provides methods of forming carbamates, ureas, and isocyanates. In certain embodiments these methods include the step of reacting an amine with an ester-substituted diaryl carbonate to form an activated carbamate which can be further derivitized to form non-activated carbamate or a urea. The urea or carbamate can be subjected to a pyrolysis reaction to form isocyanate.Type: ApplicationFiled: December 31, 2008Publication date: May 6, 2010Applicant: SABIC INNOVATIVE PLASTICS IP BVInventors: Hatem Abdallah Belfadhel, Hans-Peter Brack, Ricardo Godoy-Lopez, Dennis James Patrick Maria Willemse
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Publication number: 20100010256Abstract: Processes which include: (a) providing a gas phase comprising hydrogen chloride; (b) oxidizing the hydrogen chloride in a reactor to form a product gas comprising chlorine, unreacted hydrogen chloride and water, the reactor having structural parts with inner surfaces that are contacted during oxidation by one or both of the gas phase and the product gas; (c) cooling the process gas; (d) separating the unreacted hydrogen chloride and water from the product gas; (e) drying the product gas; and (f) separating the chlorine from the product gas; wherein the inner surfaces of the reactor structural parts that are contacted during oxidation by one or both of the gas phase and the product gas are comprised of a nickel material having a nickel content of at least 60 wt. %, are described.Type: ApplicationFiled: July 8, 2009Publication date: January 14, 2010Applicant: Bayer MaterialScience AGInventors: Andreas Bulan, Helmut Diekmann, Gerhard Ruffert, Kaspar Hallenberger
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Patent number: 7579066Abstract: There are provided a novel ethylenically unsaturated group-containing isocyanate compound, a process for producing the same, and a reactive monomer produced from the isocyanate compound, a reactive polymer and its use. The ethylenically unsaturated group-containing isocyanate compound according to the present invention is represented by formula (I).Type: GrantFiled: October 31, 2005Date of Patent: August 25, 2009Assignee: Showa Denko K.K.Inventors: Kaneo Nozawa, Katsutoshi Morinaka, Toru Sasaki, Katsumi Murofushi
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Patent number: 7557242Abstract: Cycloaliphatic diisocyanates can be prepared continuously and phosgene-free by reacting at least one cycloaliphatic diamine with at least one carbonic acid derivative and at least one alcohol to give a cycloaliphatic diurethane; freeing the cycloaliphatic diurethane of a low boiler, a medium boiler and mixtures thereof; thermally cleaving the cycloaliphatic diurethane in a cleavage apparatus to give a cycloaliphatic diisocyanate and a cleavage residue; continuously discharging a portion of the cleavage residue from the cleavage apparatus; removing the high boiler components from the discharge to obtain a purified discharge; reurethanizing the purified discharge with alcohol to obtain a reurethanized discharge; and recycling the reurethanized discharge into the process.Type: GrantFiled: April 7, 2005Date of Patent: July 7, 2009Assignee: Degussa AGInventors: Stephan Kohlstruk, Manfred Kreczinski, Hans-Werner Michalczak
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Publication number: 20090124785Abstract: An isocyanate has been widely used as a starting material for the production of a polyurethane material, a polyisocyanurate material or the like which is suitably applicable to the field of optical materials. Disclosed is a process for producing an isocyanate which includes a step for producing the isocyanate in the form of a hydrochloride with improved productivity. A process for producing a linear or cyclic aliphatic isocyanate comprising the step of reacting a linear or cyclic aliphatic amine with hydrogen chloride to yield a hydrochloride of the linear or cyclic aliphatic amine, the step being performed under a pressure higher by 0.01 MPa or more than the atmospheric pressure.Type: ApplicationFiled: July 20, 2006Publication date: May 14, 2009Applicant: Mitsui Chemicals, Inc.Inventors: Chitoshi Shimakawa, Hiroyuki Morijiri, Hidetoshi Hayashi, Norihiko Fukatsu, Seiichi Kobayashi, Homare Yumoto, Junichi Ishiyama, Shinya Tsuchiyama
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Patent number: 7482481Abstract: In a process for preparing isocyanates by reacting the corresponding primary amines with phosgene in an inert solvent, use is made of from 0.01 to 50 mol % of a phosphine oxide, based on the total amount of primary amine and isocyanate formed in the reaction solution.Type: GrantFiled: October 17, 2002Date of Patent: January 27, 2009Assignee: BASF AktiengesellschaftInventors: Thorsten Rohde, Armin Stamm, Jochem Henkelmann
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Publication number: 20090005589Abstract: A method for producing toluene diisocyanate is disclosed which comprises forming a dispersion comprising phosgene gas bubbles dispersed in toluene diamine liquid phase, wherein said gas bubbles have a mean diameter less than 1 micron; and subjecting the dispersion to phosgenation reaction conditions, whereby at least a portion of the toluene diamine is phosgenated to form toluene diisocyanate. A system for carrying out the phosgenation of toluene diamine is also disclosed.Type: ApplicationFiled: June 18, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
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Patent number: 7368595Abstract: The invention relates to an improved process for the production of isocyanates by the reaction of an amine or a mixture of two or more amines with phosgene, the improvement involving the phosgene containing less than about 100 ppm of sulfur in elemental or bound form. The inventive process yields light-colored isocyanates that are suitable for the production of polyurethanes or their precursors (e.g. prepolymers) without the treatment processes heretofore required.Type: GrantFiled: January 10, 2007Date of Patent: May 6, 2008Assignee: Bayer MaterialScience AGInventors: Stefan Wershofen, Torsten Hagen, Christian Steffens, Jeffrey Bolton
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Patent number: 7238840Abstract: 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: GrantFiled: September 21, 2004Date of Patent: July 3, 2007Assignee: Huntsman International LLCInventors: Pablo Botella Asuncion, Joris Karel Peter Bosman, Avelino Corma, Christopher John Mitchell
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Patent number: 7211689Abstract: In a process for preparing isocyanates by reacting the corresponding primary amines with phosgene in an inert solvent, use is made of from 0.01 to 50 mol % of a sulfonamide, based on the total amount of primary amine and isocyanate formed in the reaction solution.Type: GrantFiled: October 17, 2002Date of Patent: May 1, 2007Assignee: BASF AktiengesellschaftInventors: Thorsten Rohde, Armin Stamm, Jochem Henkelmann
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Patent number: 7122697Abstract: A method for producing carbamates that enables carbamates to be produced at low costs, with high selectivity and high yield, and in a simple manner, and a method for producing isocyanates that enables isocyanates industrially used to be produced by using the carbamates obtained by the carbamates producing method. Nonaromatic amine selected from the group consisting of aliphatic amine, alicyclic amine, and aralkyl amine is allowed to react with alkylaryl carbonate to thereby produce carbamates. Also, the carbamates thus obtained are thermally decomposed to thereby produce isocyanates. When carbamates are produced in this method, alkyl carbamates can be obtained with high selectivity and at high yield by using simple equipment. Also, when isocyanates are produced in this method, polyisocyanates used industrially as the raw material of polyurethane can be produced in a simple manner and with efficiency.Type: GrantFiled: December 24, 2002Date of Patent: October 17, 2006Assignee: Mitsui Takeda Chemicals, Inc.Inventors: Tsutomu Yoshida, Masaaki Sasaki, Satoshi Kuroiwa, Fumiaki Hirata
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Patent number: 7041776Abstract: The invention relates to a method of producing polyisocyanates of the diphenylmethane series including the steps of a) reacting aniline and formaldehyde in the presence of HCl to provide a product mixture containing polyamines of the diphenylmethane series, HCl, aniline and water; b) removing excess aniline and water by distillation to provide a product mixture comprising polyamines of the diphenylmethane series, HCl, no more than 10 wt. % aniline based on the polyamines, and no more than 5 wt. % water based on the polyamines; and c) phosgenating the product mixture in (b).Type: GrantFiled: September 26, 2003Date of Patent: May 9, 2006Assignee: Bayer AktiengesellschaftInventors: Daniel Koch, Hans-Georg Pirkl, Torsten Hagen, Stefan Wershofen
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Patent number: 6916953Abstract: Process for preparing organic isocyanates, which comprises the steps (a) making available a first partial amount of chlorine, with the chlorine of this first partial amount having a content of free and bound bromine and iodine of <400 ppm; (b) making available a second partial amount of chlorine; (c) reacting the first and second partial amounts of chlorine with carbon monoxide to form phosgene; (d) reacting the phosgene from step (c) with one or more primary amines to form the corresponding isocyanates and hydrogen chloride; (e) separating off and, if necessary, purifying the isocyanates formed in step (d); (f) separating off and, if necessary, purifying the hydrogen chloride formed in step (d); (g) catalytically oxidizing at least part of the hydrogen chloride separated off in step (e) by means of oxygen to form chlorine; (h) separating off the chlorine formed in step (g) and using at least a partial amount of the chlorine which has been separated off as second partial amount of chlorine in step (b).Type: GrantFiled: August 27, 2002Date of Patent: July 12, 2005Assignee: BASF AktiengesellschaftInventors: Christian Walsdorff, Martin Fiene, Eckhard Ströfer, Klaus Harth, Jan D. Jacobs, Filip Deberdt
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Patent number: 6913629Abstract: Compounds of the formula 1 OCN—R1—NHCOX—R2—(Y)n??(1), where X is a covalent bond to R2 or is O, S or NR3, Y is a hydrogen atom or a free functional group and n is an integer from 1 to 20, can be used for functionalizing or modifying compounds or solid surfaces which have at least one group which is reactive toward isocyanate.Type: GrantFiled: November 30, 2000Date of Patent: July 5, 2005Assignee: BASF AktiengesellschaftInventors: Bernd Bruchmann, Ulrich Treuling
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Patent number: 6867324Abstract: Starting material streams are mixed in a mixer (13) for the phosgenation of amines by a process in which the reaction product (3) is removed in a closed loop and the starting material streams (1.2) contain organic solvents. The main streams (1.1, 2.1) and/or part-streams (1.2, 2.2) of the starting materials (1, 2) come into contact with one another according to the countercurrent principle.Type: GrantFiled: May 21, 2001Date of Patent: March 15, 2005Assignee: BASF AktiengesellschaftInventors: Andreas Wölfert, Ulrich Penzel
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Patent number: 6833469Abstract: The invention relates to a process for the production of isocyanates by reaction of primary amines with phosgene, in which isocyanate is used as solvent, wherein some or all of isocyanate used as solvent is added to the reaction mixture only after the amine and phosgene have been physically combined.Type: GrantFiled: December 10, 2003Date of Patent: December 21, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Wölfert, Christian Müller, Eckhard Stroefer
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Patent number: 6781010Abstract: A phosgene-free process for producing organic isocyanates reacts an organic fomamide with a diorganocarbonate and thermolyzing the reaction product to obtain the corresponding organic isocyanate. Byproducts may be cycled back to the reaction or recycled to produce additional starting materials. The process product organic isocyanates in high yield.Type: GrantFiled: September 19, 2000Date of Patent: August 24, 2004Assignee: Lyondell Chemical CompanyInventor: Robert W. Mason
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Patent number: 6750367Abstract: The present invention relates to novel aromatic isocyanates obtained by partially hydrogenating naphthalene as well as the processes for preparing the same, and to their use as an isocyanate component in the production of polyurethanes.Type: GrantFiled: May 9, 2002Date of Patent: June 15, 2004Assignee: Bayer Polymers LLCInventors: Rick L. Adkins, Harold R. Parsons
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Patent number: 6664415Abstract: The present invention relates to a process for preparing a low boiling monoisocyanate having a boiling point of between 70 and 320° C. at standard pressure by reacting A) a high boiling isocyanate compound having a boiling point of at least 180° C. at standard pressure and an HC content of at least 50 ppm with B) a monoamine having a primary amino group, at a maximum reaction temperature of 180° C. and a molar ratio of isocyanate groups to amino groups of at least 4:1 to form a compound containing a biuret/urea group, simultaneously thermally decomposing this compound in situ to form a monoisocyanate corresponding to monoamine B) and removing the monoisocyanate by distillation, optionally under vacuum.Type: GrantFiled: April 30, 2001Date of Patent: December 16, 2003Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Lutz Schmalstieg, Ulrich Geron, Hans-Günter Behr, Jörg Morawski
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Patent number: 6613949Abstract: This invention is directed towards an improved process for the selective gas phase oxidation of a organic reactant using a metal oxide redox catalyst, wherein the organic reactant and air feeds are at a substantially continuous level, the improvement comprising adding a fluctuating flow of oxygen at alternating relatively high and relatively low levels. The invention also teaches means by which a gas may be provided to a reaction process on a fluctuating basis.Type: GrantFiled: March 10, 1997Date of Patent: September 2, 2003Assignee: Praxair Technology, Inc.Inventors: Matthew Lincoln Wagner, Donald Walter Welsh Kirkwood, Kazuo Kiyonaga
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Patent number: 6433218Abstract: The pot life of an isocyanate formulation is controlled by including a chain extender having (a) at least two secondary amine groups, (b) no primary amine groups, and (c) a reactivity low enough that the chain extender will not react sufficiently with isocyanate groups present in the isocyanate formulation to increase the viscosity of the isocyanate formulation to more than 2000 mPa·s within 5 seconds in the isocyanate formulation.Type: GrantFiled: November 30, 1999Date of Patent: August 13, 2002Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack, Edward P. Squiller