Preparing Esters From Nitriles Or Amides Patents (Class 560/215)
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Patent number: 10294190Abstract: Fouling of an MMA process is reduced by strategically removing an aqueous slip stream.Type: GrantFiled: October 13, 2015Date of Patent: May 21, 2019Assignee: Rohm and Haas CompanyInventors: Stacy W. Hoy, IV, Joy L. Mendoza, Mingyu Ye, Philippe P. Maillot
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Patent number: 9637574Abstract: The present invention relates to a process for preparing alkyl methacrylates and their conversion products which can be used in a multitude of chemical synthesis processes which can lead to a wide variety of different further processing products, and to an apparatus for performing this process.Type: GrantFiled: August 31, 2007Date of Patent: May 2, 2017Assignee: Evonik Röhm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Patent number: 9000211Abstract: This invention provides a method for producing ?,?-unsaturated carboxylic acid esters in high yield from acetone cyanohydrin and sulfuric acid through the separation and concurrent catalytic conversion of reaction side products to additional ?,?-unsaturated carboxylic acid ester product. The catalyst comprises at least one Group IA element and may include a porous support and/or a promoter element selected from at least one of phosphorous, boron, titanium, zinc, zirconium, tin, bismuth, cerium, and alkaline earth metals.Type: GrantFiled: October 4, 2011Date of Patent: April 7, 2015Inventors: Andrew M. Lemonds, Jinsuo Xu
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Publication number: 20150045577Abstract: The present invention relates to a process for hydrolysis of acetone cyanohydrin (ACH) by means of sulphuric acid within the ACH sulpho process for preparation of methacrylic acid (MAA) or methyl methacrylate (MMA).Type: ApplicationFiled: March 6, 2013Publication date: February 12, 2015Applicant: Evonik Roehm GmbHInventors: Arndt Selbach, Lorenza Sartorelli, Andreas Perl, Joachim Deinken, Stefanie Sohnemann, Norbert Mnich, Matthias Groemping, Udo Gropp, Thomas Mertz
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Publication number: 20140154758Abstract: The invention relates to methyl methacrylate characterized in that at least one portion of the carbons thereof is biologically sourced and, more specifically, in that it contains between 0.2×10?10 and 1.2×10?10 wt.-% of 14C in relation to total carbon weight according to the ASTM D6866 standard. The preparation method comprises the use of acetone cyanohydrin as a raw material, said acetone cyanohydrin being obtained by condensing cyanohydric acid on acetone, and the methyl methacrylate is prepared using a process involving the addition of methanol. According to the invention, at least one from among the acetone, cyanohydric acid and methanol is obtained by means of a reaction or series of reactions involving the biomass.Type: ApplicationFiled: February 7, 2014Publication date: June 5, 2014Inventors: JEAN-LUC DUBOIS, Jean Francois Croizy
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Publication number: 20130338396Abstract: This invention provides a method for producing ?,?-unsaturated carboxylic acid esters in high yield from acetone cyanohydrin and sulfuric acid through the separation and concurrent catalytic conversion of reaction side products to additional ?,?-unsaturated carboxylic acid ester product. The catalyst comprises at least one Group IA element and may include a porous support and/or a promoter element selected from at least one of phosphorous, boron, titanium, zinc, zirconium, tin, bismuth, cerium, and alkaline earth metals.Type: ApplicationFiled: October 4, 2011Publication date: December 19, 2013Applicant: ROHM AND HAAS COMPANYInventors: Andrew M. Lemonds, Jinsuo Xu
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Patent number: 8586779Abstract: The present invention relates in general terms to a process for preparing alkyl methacrylates, comprising as steps: providing an acetone cyanohydrin by a process according to one of the preceding claims; contacting the acetone cyanohydrin with an inorganic acid to obtain a methacrylamide; contacting the methacrylamide with an alcohol in the presence of an inorganic acid in a reactor to obtain an alkyl methacrylate; continuously discharging at least a portion of the alkyl methacrylate from the reactor into a distillation column as a vapor stream; the discharge being effected by feeding a discharge stream comprising steam into the reactor, to an apparatus for preparing alkyl methacrylates, to a process for preparing polymers based at least partly on alkyl methacrylates, to the use of the alkyl methacrylates obtainable by the process according to the invention in chemical products, and to chemical products based on alkyl methacrylates obtainable by the process according to the invention.Type: GrantFiled: August 31, 2007Date of Patent: November 19, 2013Assignee: Evonik Röhm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Patent number: 8334406Abstract: The present invention relates to a process for preparing carboxamides by hydrolysing carbonitriles in the presence of a catalyst comprising manganese dioxide, wherein the reaction mixture added to the catalyst comprising manganese dioxide has a pH in the range of 6.0 to 11.0 and the hydrolysis is performed in the presence of an oxidizing agent. The present invention further relates to a process for preparing alkyl (meth)acrylates, the process having a hydrolysis step according to the process described above.Type: GrantFiled: August 30, 2007Date of Patent: December 18, 2012Assignee: Evonik Roehm GmbHInventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
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Publication number: 20110306784Abstract: The invention relates to a method for producing a carboxylic acid amide from a carbonyl compound and hydrocyanic acid, comprising the steps of A) reacting a carbonyl compound with hydrocyanic acid to produce a hydroxycarboxylic acid nitrile, B) hydrolysis of the hydroxycarboxylic acid nitrile obtained in step A) in the presence of a catalyst comprising manganese dioxide, wherein a molar excess of carbonyl compound is used in relation to the hydrocyanic acid to react the carbonyl compound with hydrocyanic acid according to step A), and the reaction mixture obtained in step A) is not purified by distillation before the hydrolysis according to step B) is carried out. The invention furthermore relates to a method for producing alkyl(meth)acrylates from polymers, moulding compounds and moulded bodies, wherein a method for producing a carboxylic acid amide from a carbonyl compound and hydrocyanic acid is carried out in accordance with the method described above.Type: ApplicationFiled: October 29, 2009Publication date: December 15, 2011Applicant: EVONIK ROEHM GMBHInventors: Alexander May, Martin Koestner, Joerg Becker, Joerg Schallenberg, Hermann Siegert, Bernd Vogel
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Publication number: 20110077424Abstract: The present invention provides a method for extractive recovery and conversion of selected compounds, such as methacrylic acid (MAA) and 2-methacrylamide (MAM), from a stream derived from purification of methyl methacrylate (MMA) or methacrylic acid (MAA) produced via a conventional ACH route process.Type: ApplicationFiled: September 13, 2010Publication date: March 31, 2011Inventors: Andrew M. Lemonds, Jinsuo Xu
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Publication number: 20110060159Abstract: The present invention relates to a process for preparing carboxamides by hydrolysing carbonitriles in the presence of a catalyst comprising manganese dioxide, wherein the reaction mixture added to the catalyst comprising manganese dioxide has a pH in the range of 6.0 to 11.0 and the hydrolysis is performed in the presence of an oxidizing agent. The present invention further relates to a process for preparing alkyl (meth)acrylates, the process having a hydrolysis step according to the process described above.Type: ApplicationFiled: August 30, 2007Publication date: March 10, 2011Applicant: Evonik Roehm GmbHInventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
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Publication number: 20100249449Abstract: The present invention relates to a process for preparing carboxamides by amidating nitriles in the presence of sulphuric acid, wherein the reaction is performed in a Taylor reactor. The process enables a simple and inexpensive preparation of these compounds. The present invention further provides processes for preparing (meth)acrylamides and alkyl(meth)acrylates, which comprise an inventive amidation reaction.Type: ApplicationFiled: August 15, 2008Publication date: September 30, 2010Applicant: Evonik Roehm GmbHInventors: Lorenza Sartorelli, Andreas Perl, Udo Gropp, Arndt Selbach
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Publication number: 20100069662Abstract: The subject-matter of the present invention relates in principle to a process for preparing alkyl esters of methacrylic acid and its conversion products, which can be used in a multitude of chemical synthesis processes which can lead to a wide variety of different further processing products, and to an apparatus for performing this process.Type: ApplicationFiled: August 31, 2007Publication date: March 18, 2010Applicant: Evonik Roehm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Publication number: 20100069594Abstract: The present invention relates in general terms to a process for preparing acetone cyanohydrin, comprising as steps: A. contacting acetone and hydrocyanic acid in a reactor to give a reaction mixture, the reaction mixture being circulated, to obtain acetone cyanohydrin; B. cooling at least some of the reaction mixture; C. discharging at least a portion of the acetone cyanohydrin obtained from the reactor; D. continuously distilling the discharged acetone cyanohydrin obtained to obtain an acetone cyanohydrin bottom product and an acetone top product in a distillation column; E. recycling at least a portion of the acetone top product into step A, the acetone top product being kept at less than 60° C.Type: ApplicationFiled: August 31, 2007Publication date: March 18, 2010Applicant: Evonik Roehm GmbHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Publication number: 20100029881Abstract: The present invention relates in general terms to a process for preparing alkyl methacrylates, comprising as steps: providing an acetone cyanohydrin by a process according to one of the preceding claims; contacting the acetone cyanohydrin with an inorganic acid to obtain a methacrylamide; contacting the methacrylamide with an alcohol in the presence of an inorganic acid in a reactor to obtain an alkyl methacrylate; continuously discharging at least a portion of the alkyl methacrylate from the reactor into a distillation column as a vapour stream; the discharge being effected by feeding a discharge stream comprising steam into the reactor, to an apparatus for preparing alkyl methacrylates, to a process for preparing polymers based at least partly on alkyl methacrylates, to the use of the alkyl methacrylates obtainable by the process according to the invention in chemical products, and to chemical products based on alkyl methacrylates obtainable by the process according to the invention.Type: ApplicationFiled: August 31, 2007Publication date: February 4, 2010Applicant: EVONIK ROEHM GMBHInventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
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Publication number: 20090198014Abstract: A mixture of compounds useful to make a polymer or a prepolymer, the mixture of compounds including compounds having the formula I; wherein R1 is H, acryloyl, methacryloyl or vinyl, wherein R2 is acryloyl, methacryloyl or vinyl, wherein compounds having the formula I consist of a mixture of cis and trans-1,3- and 1,4-substituted cyclohexane and wherein the trans-1,4-substituted cyclohexane content of the compounds having the formula I is less than forty mole percent. A process for producing a mixture of compounds including compounds having the formula II: wherein compounds having the formula II consist of a mixture of cis and trans-1,3- and 1,4-methanol substituted cyclohexane and wherein the trans-1,4-methanol substituted cyclohexane content of the compounds having the formula II is less than twenty five mole percent.Type: ApplicationFiled: December 7, 2006Publication date: August 6, 2009Inventors: Kiran K. Baikerikar, Michael L. Tulchinsky, John N. Argyropoulos
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Patent number: 7375247Abstract: A method for producing MMA-d8 which includes a step of exchanging D in hydroxyl group of methanol-d4 represented by the formula: CD3OD with H to prepare the methanol-d3 represented by the formula CD3OH and simultaneously recovering a deuterium-containing compound, and a step of reacting methanol-d3 with sulfuric acid salt of methacrylic acid amide represented by the formula CD2=(CD3)CO(NH2.H2SO4) to prepare MMA-d8 represented by the formula: CD2=(CD3)COOCD3.Type: GrantFiled: September 1, 2004Date of Patent: May 20, 2008Assignee: Taiyo Nippon Sanso CorporationInventors: Yuichi Sugano, Takafumi Abe, Toshifumi Abe
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Publication number: 20030208093Abstract: Provided herein are improved methods for producing methacrylic acid and methacrylate esters using combined or “integrated” processing steps including integrated hydrolysis, integrated cracking systems, and combinations thereof. In one embodiment, other aspects of an methacrylic acid and methacrylate ester production trains are integrated. Also provided are methods to purify crude methacrylic acid streams to form glacial methacrylic acid that is at least 95% pure.Type: ApplicationFiled: April 22, 2003Publication date: November 6, 2003Inventors: Curtis Ingstad Carlson, Michael Stanley DeCourcy, Jamie Jerrick John Juliette
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Patent number: 6610177Abstract: A high yield process for the production of methyl methacrylate or methacrylic acid and an apparatus for increasing the yield in a process for the production of methyl methacrylate or methacrylic acid are disclosed.Type: GrantFiled: July 29, 2002Date of Patent: August 26, 2003Assignee: Rohm and Haas CompanyInventors: Chorng-Shyuan Tsay, Michael Stanley DeCourcy, I-Hwa Midey Chang-Mateu, Heather Granzin Thompson, Diana Elaine Chase
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Patent number: 6603034Abstract: A process for preparing organozinc halides in solvents, includes reacting a reactive halogen compound with zinc in one or more carboxylic esters. It is also possible to prepare keto, hydroxyl and amino compounds of organozinc halides obtained in a first step from a reactive halogen compound and zinc in one or more carboxylic esters, wherein the organozinc halide obtained is reacted in a second step with an electrophilic reaction partner and the reaction product of the second step is hydrolyzed in a third step.Type: GrantFiled: December 3, 2002Date of Patent: August 5, 2003Assignee: Consortium für Elektrochemische Industrie GmbHInventors: Klas Sorger, Hermann Petersen, Jürgen Stohrer
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Patent number: 6545176Abstract: A high yield process for the production of methyl methacrylate or methacrylic acid and an apparatus for increasing the yield in a process for the production of methyl methacrylate or methacrylic acid are disclosed.Type: GrantFiled: October 28, 1999Date of Patent: April 8, 2003Assignee: Rohm and Haas CompanyInventors: Chorng-Shyuan Tsay, Makarand Dattatraya Phadke, Abraham Benderly, I-Hwa Midey Chang-Mateu, Nicole Rendon Koegel, Heather Granzin Thompson, Diana Elaine Chase
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Publication number: 20020188153Abstract: A high yield process for the production of methyl methacrylate or methacrylic acid and an apparatus for increasing the yield in a process for the production of methyl methacrylate or methacrylic acid are disclosed.Type: ApplicationFiled: July 29, 2002Publication date: December 12, 2002Inventors: Chorng-Shyuan Tsay, Michael Stanley DeCourcy, I-Hwa Midey Chang-Mateu, Heather Granzin Thompson, Diana Elaine Chase
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Patent number: 6437016Abstract: The invention relates to a radiation curable compound being a mono or multi valent carboxylic ester of a compound containing a hydroxyalkylamidegroup and a hydroxygroup in which the carboxylic ester is derived from an &agr;,&bgr;-ethylenically unsaturated carboxylic acid. A coating composition comprising this compound has a high rate of polymerisation and shows the desired chemical and mechanical properties.Type: GrantFiled: January 8, 2001Date of Patent: August 20, 2002Assignee: DSM N.V.Inventors: Johan F. G. A. Jansen, Aylvin J. A. A. Dias, Pascal M. H. P. Tijssen
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Patent number: 6310236Abstract: There is herein disclosed a process for efficiently preparing, from an &agr;-hydroxycarboxylic amide and an alcohol in an industrially advantageous manner, an &agr;-hydroxycarboxylate which is useful as any of raw materials for solvents, food additives, perfumes, various organic medicines and the like. According to the present invention, there is provided a process for preparing an &agr;-hydroxycarboxylate which comprises the step of reacting an &agr;-hydroxycarboxylic amide and an alcohol in the presence of a catalyst in a liquid phase, while an ammonia concentration in a reaction solution is maintained at 0.1% by weight or less by discharging generated ammonia as a gas into a gaseous phase.Type: GrantFiled: March 23, 1999Date of Patent: October 30, 2001Assignee: Mitsubishi Gas Chemical CompanyInventors: Kenichi Nakamura, Futoshi Kawataka, Kazuhiro Yamada, Wataru Ueno
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Patent number: 6245829Abstract: The invention relates to a radiation curable composition comprising a mono or mulit valent carboxylic ester of a &bgr;-hydroxyalkylamide group containing compound, in which the carboxylic ester is derived from an &agr;,&bgr;-ethylenically unsaturated carboxylic acid. A coating composition based on this composition has a high rate of polymerisation and shows the desired chemical and mechanical properties.Type: GrantFiled: July 29, 1999Date of Patent: June 12, 2001Assignee: DSM NVInventors: Theodoor H. Meij, Marten Houweling, Aylvin J. A. A. Dias, Johan F. G. A. Jansen, Rudolfus A. T. M. Van Benthem
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Patent number: 6075162Abstract: A method of producing methyl methacrylate comprises Step 1 of producing acetone cyanhydrin from hydrogen cyanide and acetone; Step 2 of producing .alpha.-hydroxyisobutyramide by hydrating acetone cyanhydrin; Step 3 of producing methyl .alpha.-hydroxyisobutyrate and ammonia by a reaction of .alpha.-hydroxyisobutyramide and methanol; Step 4 of producing methyl methacrylate by dehydrating methyl .alpha.-hydroxyisobutyrate; and Step 5 of producing hydrogen cyanide in vapor phase by reacting methanol and the ammonia obtained in Step 3 over a solid catalyst in the presence of molecular oxygen. By using methanol in the step 3, the conversion ratio of .alpha.-hydroxyisobutyramide into methyl .alpha.-hydroxyisobutyrate can be increased because the equilibrium of the reaction is easily sifted toward the product side by removing ammonia being produced from the reaction system.Type: GrantFiled: March 2, 1999Date of Patent: June 13, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Koichi Kida
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Patent number: 6002010Abstract: A process for preparing carboxylic acid derivatives of the formula I ##STR1## where X is OR.sup.2 or NH.sub.2,R.sup.1 is C.sub.1 -C.sub.20 -alkyl, C.sub.l -C.sub.20 -hydroxyalkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.4 -C.sub.12 -alkylcycloalkyl, C.sub.4 -C.sub.12 -cycloalkylalkyl, C.sub.5 -C.sub.20 -alkylcycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, a heteroaliphatic or heteroaromatic ring with 5 to 8 carbon atoms andR.sup.2 is C.sub.1 -C.sub.20 -alkyl,from carbonitriles of the formula IIR.sup.1 --C.tbd.N (II),where R.sup.1 has the abovementioned meanings, and alcohols of the formula IIIR.sup.2 --OH (III),where R.sup.2 has the abovementioned meanings, at from 50 to 300.degree. C. under from 0.1 to 350 bar in the presence of a heterogeneous catalyst, wherein the reaction is carried out in liquid phase.Type: GrantFiled: November 10, 1997Date of Patent: December 14, 1999Assignee: BASF AktiengesellschaftInventor: Eberhard Fuchs
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Patent number: 5990345Abstract: A process for the preparation of ethylenically unsaturated isocyanates is described, which process comprises silylating an appropriate ethylenically unsaturated urethane precursor at the urethane nitrogen and converting the resulting unsaturated N-silyl-urethane by means of thermolysis at elevated temperature into the desired isocyanate. The unsaturated isocyanates obtainable according to the process are suitable, for example, as monomers or comonomers in the preparation of polymerisates or copolymerisates.Type: GrantFiled: December 2, 1997Date of Patent: November 23, 1999Inventors: Dieter Lohmann, Rudolf Duthaler
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Patent number: 5705602Abstract: A star-like or comb-like branched aliphatic polyamino compound for use as a basic catalyst or a curing agent, as an effective thixotropic agent or viscosity adjusting agent for an aqueous medium, as a component for any one of a coating-forming agent, a sealing agent, a molding material and an adhesive resin, or as a substantially solvent-free coating composition, molding material or adhesive resin. The process for the production of the above compound comprises (a) forming an adduct of ammonia or an aliphatic amino compound having an amino group (compound A) with methyl acrylate, adding an alkylenediamine having 2 to 12 carbon atoms to the adduct to carry out an ester-amide exchange reaction (b), thereby obtaining a polyamino compound (B) having a total of 2 to 100 aliphatic primary amino and secondary amino groups per molecule and having a number average molecular weight of 170 to 10,000, and forming an adduct of the polyamino compound (B) with an acrylic acid ester (C) of the formula (1),CH.sub.2 =CHCOO--R.Type: GrantFiled: February 19, 1997Date of Patent: January 6, 1998Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Miki Kawashima, Takeo Yamaguchi, Toru Kurihashi, Norifumi Watanabe
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Patent number: 5393918Abstract: This invention provides a method for producing .alpha.,.beta.-unsaturated carboxylic acid esters in high yield from acetone cyanohydrin and sulfuric acid through the reduction of reaction side products and the recycling of process intermediates.Type: GrantFiled: December 2, 1993Date of Patent: February 28, 1995Assignee: Rohm and Haas CompanyInventor: John C. Dobson
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Patent number: 5312966Abstract: There is disclosed a process for efficiently producing a carboxylic acid ester and formamide by reacting a carboxylic acid amide with a formic acid ester or with an alcohol and carbon monoxide in the presence of a strongly basic anion-exchange resin. By the use of the strongly basic anion-exchange resin as the catalyst, the process of the present invention enables the efficient production of the carboxylic acid ester as well as formamide from the Carboxylic acid amide and Formic acid ester, etc. with a high selectivity under mild reaction conditions and facilitates the separation of the catalyst from the reaction product, thereby greatly enhancing the industrial significance of itself.Type: GrantFiled: September 14, 1992Date of Patent: May 17, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Yoshiyuki Nishide, Nobuyuki Muro, Hirofumi Higuchi
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Patent number: 5268503Abstract: .alpha.,.beta.-Unsaturated carboxylic acid esters are produced by a catalytic reaction of .alpha.,.beta.-unsaturated carboxylic acids and/or .alpha.,.beta.-unsaturated carboxylic acid amides with aliphatic alcohols in the presence of a solid acid catalyst comprising zirconium oxide, titanium oxide or a composite oxide thereof containing phosphorus.Type: GrantFiled: March 9, 1993Date of Patent: December 7, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Minato Karasawa, Sinji Tokunoh, Masamitsu Inomata, Takeshi Hiraiwa, Hiroharu Kageyama, Kanemitsu Miyama
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Patent number: 5194668Abstract: Carboxylic acid esters and formamide are efficiently obtained by reacting carboxylic acid amides and formic acid esters, or by reacting carboxylic acid amides, alcohols and carbon monoxide in the presence of a dehydrated condensate of carboxylic acid amide with an alkali metal hydroxide or an alkaline earth metal hydroxide catalyst.Type: GrantFiled: June 8, 1990Date of Patent: March 16, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
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Patent number: 5087736Abstract: Disclosed is a process for producing methyl methacrylate which comprises:(I) a step of reacting acetone and prussic acid to form acetonecyanhydrin;(II) a step of hydrating the acetonecyanhydrin obtained in the step (I) to form .alpha.-hydroxyisobutyric acid amide;(III) a step of reacting the .alpha.-hydroxyisobutyric acid amide obtained in the step (II) which methyl formate to form methyl .alpha.-hydroxyisobutyrate and formamide;(IV) a step of dehydrating the methyl .alpha.-hydroxyisobutyrate obtained in the step (III) to form methyl methancrylate; and(V) a step of decomposing the formamide obtained in the step (IV) into ammonia and carbon monoxide.The process can produce methyl methacrylate at high yields without by-production of acidic ammonium sulfate.Type: GrantFiled: May 29, 1990Date of Patent: February 11, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hirofumi Higuchi, Koichi Kida
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Patent number: 5087737Abstract: Disclosed is a process for producing methyl methacrylate which comprises:(I) a step of reacting prussic acid and acetone to form acetonecyanhydrin;(II) a step of hydrating the acetonecyanhydrin obtained in the step (I) to form .alpha.-hydroxyisobutyric acid amide;(III) a step of dehydrating the .alpha.-hydroxyisobutyric acid amide obtained in the step (II) to form methacrylic acid amide;(IV) a step of reacting the methacrylic acid amide obtained in the step (III) and methyl formate to form methyl methacrylate and formamide; and(V) a step of dehydrating formamide separated from the product obtained in the step (IV) to form prussic acid and recycling said prussic acid as a starting material in the step (I).The process produces methyl methacrylate with high selectivity without undesirable by-product such as ammonium sulfate.Type: GrantFiled: May 29, 1990Date of Patent: February 11, 1992Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hirofumi Higuchi, Koichi Kida, Shuji Ebata
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Patent number: 4990651Abstract: Carboxylic acid esters, industrially important compounds, are obtained by reacting carboxylic acid amides and formic acid esters, or carboxylic acid amides, alcohols and carbon monoxide in the presence of metal alcoholate.Type: GrantFiled: April 12, 1989Date of Patent: February 5, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideo Ikarashi, Yoshio Kawai, Seiji Nagasawa, Hiroyuki Hirayama
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Patent number: 4973739Abstract: Carboxylic acid esters, industrially important compounds, are efficiently obtained by reacting carboxylic acid amides with formic acid esters in the presence of an inorganic solid acid catalyst.Type: GrantFiled: April 12, 1989Date of Patent: November 27, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Seiji Nagasawa, Hideo Ikarashi, Yoshio Kawai, Hiroyuki Hirayama
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Patent number: 4950788Abstract: Acrylic acid or other unsaturated carboxylic acid is made by hydrolysing the corresponding nitrile in the presence of excess sulphuric acid to form amide sulphate, adding amide in an amount such that the total amount of amide and nitrile fed to the process is greater than 1 mole per mole sulphuric acid, hydrolysing the amide sulphate and amide to the desired acid and separating the acid from the sulphate by-products.Type: GrantFiled: February 23, 1989Date of Patent: August 21, 1990Assignee: Allied Colloids LimitedInventors: David Farrar, Peter Flesher
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Patent number: 4668818Abstract: In the process for the preparation of methyl methacrylate, the addition of aromatic diamine in an acidic environment reduces yellow color in the polymerized product.Type: GrantFiled: June 18, 1985Date of Patent: May 26, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hayden I. Lipp, Richard H. Squire
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Patent number: 4645856Abstract: Perdeuterated methacrylates of a high degree of deuteration can be obtained by a process for the preparation of perdeuterated methacrylates from hexadeuteroacetone by conversion into the corresponding cyanohydrin, subsequent elimination of water, hydrolysis of the cyano group and esterification with perdeuterated alkanols, the conversion of hexadeuteroacetone into the cyanohydrin being effected by reaction with trimethylsilyl cyanide to give 1,3-hexadeutero-2-(trimethylsiloxy)-2-cyano-propane and subsequent hydrolytic elimination of the trimethylsilyl group.Type: GrantFiled: April 15, 1985Date of Patent: February 24, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventor: Thomas Herold
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Patent number: 4596889Abstract: A process for the preparation of an alkenyl-lactic acid ester by reaction of a cyanohydrin with an alcohol in the presence of hydrogen chloride, followed by hydrolysis. The compounds obtained may be used for the preparation of alkaloids and crop protection agents, and as monomers for copolymerization.Type: GrantFiled: February 22, 1985Date of Patent: June 24, 1986Assignee: BASF AktiengesellschaftInventors: Michael Kroener, Walter Goetze
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Patent number: 4558120Abstract: Dense star polymers having terminal group densities greater than conventional star polymers exhibit greater and more uniform reactivity than their corresponding conventional star polymers. For example, a third generation, amine-terminated polyamidoamine dense star polymer prepared from ammonia, methyl acrylate and ethylenediamine has 1.24.times.10.sup.-4 amine moieties per unit volume (cubic Angstrom units) in contrast to the 1.58.times.10.sup.-6 amine moieties per unit volume contained by a conventional star polymer. Such dense star polymers are useful as demulsifiers for oil/water emulsions, wet strength agents in the manufacture of paper, and agents for modifying viscosity in aqueous formulations such as paints.Type: GrantFiled: December 27, 1983Date of Patent: December 10, 1985Assignee: The Dow Chemical CompanyInventors: Donald A. Tomalia, James R. Dewald
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Patent number: 4529816Abstract: In the process for making alkyl methacrylates from acetone cyanohydrin and H.sub.2 SO.sub.4, it has been found that alkyl 2-hydroxy-2-methyl propionate made during the process can be collected and returned to the process sequence just prior to the esterification step where it can be dehydrated to alkyl methacrylate.Type: GrantFiled: February 13, 1984Date of Patent: July 16, 1985Assignee: E. I. Du Pont De Nemours and CompanyInventors: Raymond L. DeColibus, Jan J. van Heiningen, Thomas F. Veerkamp
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Patent number: 4480116Abstract: The present invention provides an improvement in methods for preparing and processing readily polymerizable acrylate monomers. The improvement comprises employing phenyl-para-benzoquinone, 2,5-di-phenyl-para-benzoquinone, and mixtures thereof as process inhibitors. The process inhibitors are present in a concentration of about 50 to 3000 ppm, preferably about 250 to 2000 ppm, and most preferably about 500 ppm.Type: GrantFiled: March 2, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: Ambrose J. Clonce, Michael Palmer, Samuel L. Gott
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Patent number: 4450112Abstract: Reaction of a nitrile, an alcohol and water in the presence of a catalyst comprising rhodium, iridium or platinum complexed with hydroxo and tertiary phosphine moieties, to produce the corresponding carboxylic ester.Type: GrantFiled: November 25, 1981Date of Patent: May 22, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stanley S. Wreford
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Patent number: 4408067Abstract: In a process for preparing a carboxylic acid ester from a nitrile, water and an alcohol in the vapor phase, wherein the vapor is brought into contact with a catalyst, the improvement which comprises said catalyst being a titanium containing oxide catalyst which is obtained by hydrolyzing or neutralizing a water soluble titanium salt and subsequently calcining the resulting precipitate at a temperature in a range of about 300.degree. to 750.degree. C. and having the empirical formula Ti.sub.a Me.sub.b X.sub.c O.sub.d, wherein Me represents at least one element selected from the group consisting of Cu, Ag, Au, Mg, Zn, Sn, Pb, Zr, V, Bi, Cr, W, Mo, Mn, Fe, Co and Ni and X represents at least one element selected from the group consisting of Si and Sb and the subscripts a, b, c and d designate the atomic ratio and when a is 1, b is 0.01 to 12, c is 0 to 12 and b+c is 0.01 to 12 and d is the oxygen content of the catalyst formed by the combination of the above components.Type: GrantFiled: July 28, 1981Date of Patent: October 4, 1983Assignee: Nitto Chemical Industries, Ltd.Inventors: Tomio Nakamura, Shunichi Doi
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Patent number: 4161609Abstract: A method is provided for converting a carboxylic acid amide to a carboxylic acid ester by reacting a vaporized mixture of the amide and an aliphatic alcohol or a phenol in the presence of a suitable catalyst at temperatures of from 100.degree. C. to 400.degree. C. The process is especially useful for the conversion of methacrylamide to methyl methacrylate.Type: GrantFiled: September 14, 1977Date of Patent: July 17, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard D. Cramer
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Patent number: 4092339Abstract: Homopolymers and copolymers of glycidyl esters are made by reacting the acids to be esterified with the corresponding polymer of tert.-alkyl glycidyl ether under substantially anhydrous conditions and in the presence of a strong acid catalyst, preferably a sulfonic acid. The reaction proceeds satisfactorily at about 100.degree.14 150.degree. C with displacement of the tert.-alkyl group by the acyl group of the acid and evolution of tert.-olefin. By use of the appropriate proportion of reactant acid and/or appropriate reaction time, any desired proportion of the glycidyl groups can be esterified.Type: GrantFiled: November 19, 1975Date of Patent: May 30, 1978Assignee: The Dow Chemical CompanyInventors: Violete L. Stevens, Arthur R. Sexton, Frederick P. Corson