Preparing Esters From Nitriles Or Amides Patents (Class 560/215)
  • Patent number: 10294190
    Abstract: Fouling of an MMA process is reduced by strategically removing an aqueous slip stream.
    Type: Grant
    Filed: October 13, 2015
    Date of Patent: May 21, 2019
    Assignee: Rohm and Haas Company
    Inventors: Stacy W. Hoy, IV, Joy L. Mendoza, Mingyu Ye, Philippe P. Maillot
  • Patent number: 9637574
    Abstract: 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: Grant
    Filed: August 31, 2007
    Date of Patent: May 2, 2017
    Assignee: Evonik Röhm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Patent number: 9000211
    Abstract: 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: Grant
    Filed: October 4, 2011
    Date of Patent: April 7, 2015
    Inventors: Andrew M. Lemonds, Jinsuo Xu
  • Publication number: 20150045577
    Abstract: 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: Application
    Filed: March 6, 2013
    Publication date: February 12, 2015
    Applicant: Evonik Roehm GmbH
    Inventors: Arndt Selbach, Lorenza Sartorelli, Andreas Perl, Joachim Deinken, Stefanie Sohnemann, Norbert Mnich, Matthias Groemping, Udo Gropp, Thomas Mertz
  • Publication number: 20140154758
    Abstract: 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: Application
    Filed: February 7, 2014
    Publication date: June 5, 2014
    Inventors: JEAN-LUC DUBOIS, Jean Francois Croizy
  • Publication number: 20130338396
    Abstract: 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: Application
    Filed: October 4, 2011
    Publication date: December 19, 2013
    Applicant: ROHM AND HAAS COMPANY
    Inventors: Andrew M. Lemonds, Jinsuo Xu
  • Patent number: 8586779
    Abstract: 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: Grant
    Filed: August 31, 2007
    Date of Patent: November 19, 2013
    Assignee: Evonik Röhm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Patent number: 8334406
    Abstract: 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: Grant
    Filed: August 30, 2007
    Date of Patent: December 18, 2012
    Assignee: Evonik Roehm GmbH
    Inventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Publication number: 20110306784
    Abstract: 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: Application
    Filed: October 29, 2009
    Publication date: December 15, 2011
    Applicant: EVONIK ROEHM GMBH
    Inventors: Alexander May, Martin Koestner, Joerg Becker, Joerg Schallenberg, Hermann Siegert, Bernd Vogel
  • Publication number: 20110077424
    Abstract: 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: Application
    Filed: September 13, 2010
    Publication date: March 31, 2011
    Inventors: Andrew M. Lemonds, Jinsuo Xu
  • Publication number: 20110060159
    Abstract: 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: Application
    Filed: August 30, 2007
    Publication date: March 10, 2011
    Applicant: Evonik Roehm GmbH
    Inventors: Alexander May, Jochen Ackermann, Hermann Siegert, Bernd Vogel, Soenke Broecker
  • Publication number: 20100249449
    Abstract: 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: Application
    Filed: August 15, 2008
    Publication date: September 30, 2010
    Applicant: Evonik Roehm GmbH
    Inventors: Lorenza Sartorelli, Andreas Perl, Udo Gropp, Arndt Selbach
  • Publication number: 20100069662
    Abstract: 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: Application
    Filed: August 31, 2007
    Publication date: March 18, 2010
    Applicant: Evonik Roehm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Publication number: 20100069594
    Abstract: 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: Application
    Filed: August 31, 2007
    Publication date: March 18, 2010
    Applicant: Evonik Roehm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Publication number: 20100029881
    Abstract: 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: Application
    Filed: August 31, 2007
    Publication date: February 4, 2010
    Applicant: EVONIK ROEHM GMBH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Publication number: 20090198014
    Abstract: 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: Application
    Filed: December 7, 2006
    Publication date: August 6, 2009
    Inventors: Kiran K. Baikerikar, Michael L. Tulchinsky, John N. Argyropoulos
  • Patent number: 7375247
    Abstract: 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: Grant
    Filed: September 1, 2004
    Date of Patent: May 20, 2008
    Assignee: Taiyo Nippon Sanso Corporation
    Inventors: Yuichi Sugano, Takafumi Abe, Toshifumi Abe
  • Publication number: 20030208093
    Abstract: 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: Application
    Filed: April 22, 2003
    Publication date: November 6, 2003
    Inventors: Curtis Ingstad Carlson, Michael Stanley DeCourcy, Jamie Jerrick John Juliette
  • Patent number: 6610177
    Abstract: 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: Grant
    Filed: July 29, 2002
    Date of Patent: August 26, 2003
    Assignee: Rohm and Haas Company
    Inventors: Chorng-Shyuan Tsay, Michael Stanley DeCourcy, I-Hwa Midey Chang-Mateu, Heather Granzin Thompson, Diana Elaine Chase
  • Patent number: 6603034
    Abstract: 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: Grant
    Filed: December 3, 2002
    Date of Patent: August 5, 2003
    Assignee: Consortium für Elektrochemische Industrie GmbH
    Inventors: Klas Sorger, Hermann Petersen, Jürgen Stohrer
  • Patent number: 6545176
    Abstract: 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: Grant
    Filed: October 28, 1999
    Date of Patent: April 8, 2003
    Assignee: Rohm and Haas Company
    Inventors: Chorng-Shyuan Tsay, Makarand Dattatraya Phadke, Abraham Benderly, I-Hwa Midey Chang-Mateu, Nicole Rendon Koegel, Heather Granzin Thompson, Diana Elaine Chase
  • Publication number: 20020188153
    Abstract: 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: Application
    Filed: July 29, 2002
    Publication date: December 12, 2002
    Inventors: Chorng-Shyuan Tsay, Michael Stanley DeCourcy, I-Hwa Midey Chang-Mateu, Heather Granzin Thompson, Diana Elaine Chase
  • Patent number: 6437016
    Abstract: 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: Grant
    Filed: January 8, 2001
    Date of Patent: August 20, 2002
    Assignee: DSM N.V.
    Inventors: Johan F. G. A. Jansen, Aylvin J. A. A. Dias, Pascal M. H. P. Tijssen
  • Patent number: 6310236
    Abstract: 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: Grant
    Filed: March 23, 1999
    Date of Patent: October 30, 2001
    Assignee: Mitsubishi Gas Chemical Company
    Inventors: Kenichi Nakamura, Futoshi Kawataka, Kazuhiro Yamada, Wataru Ueno
  • Patent number: 6245829
    Abstract: 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: Grant
    Filed: July 29, 1999
    Date of Patent: June 12, 2001
    Assignee: DSM NV
    Inventors: Theodoor H. Meij, Marten Houweling, Aylvin J. A. A. Dias, Johan F. G. A. Jansen, Rudolfus A. T. M. Van Benthem
  • Patent number: 6075162
    Abstract: 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: Grant
    Filed: March 2, 1999
    Date of Patent: June 13, 2000
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Koichi Kida
  • Patent number: 6002010
    Abstract: 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: Grant
    Filed: November 10, 1997
    Date of Patent: December 14, 1999
    Assignee: BASF Aktiengesellschaft
    Inventor: Eberhard Fuchs
  • Patent number: 5990345
    Abstract: 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: Grant
    Filed: December 2, 1997
    Date of Patent: November 23, 1999
    Inventors: Dieter Lohmann, Rudolf Duthaler
  • Patent number: 5705602
    Abstract: 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: Grant
    Filed: February 19, 1997
    Date of Patent: January 6, 1998
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Miki Kawashima, Takeo Yamaguchi, Toru Kurihashi, Norifumi Watanabe
  • Patent number: 5393918
    Abstract: 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: Grant
    Filed: December 2, 1993
    Date of Patent: February 28, 1995
    Assignee: Rohm and Haas Company
    Inventor: John C. Dobson
  • Patent number: 5312966
    Abstract: 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: Grant
    Filed: September 14, 1992
    Date of Patent: May 17, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Abe, Yoshiyuki Nishide, Nobuyuki Muro, Hirofumi Higuchi
  • Patent number: 5268503
    Abstract: .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: Grant
    Filed: March 9, 1993
    Date of Patent: December 7, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Minato Karasawa, Sinji Tokunoh, Masamitsu Inomata, Takeshi Hiraiwa, Hiroharu Kageyama, Kanemitsu Miyama
  • Patent number: 5194668
    Abstract: 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: Grant
    Filed: June 8, 1990
    Date of Patent: March 16, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
  • Patent number: 5087736
    Abstract: 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: Grant
    Filed: May 29, 1990
    Date of Patent: February 11, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hirofumi Higuchi, Koichi Kida
  • Patent number: 5087737
    Abstract: 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: Grant
    Filed: May 29, 1990
    Date of Patent: February 11, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hirofumi Higuchi, Koichi Kida, Shuji Ebata
  • Patent number: 4990651
    Abstract: 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: Grant
    Filed: April 12, 1989
    Date of Patent: February 5, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideo Ikarashi, Yoshio Kawai, Seiji Nagasawa, Hiroyuki Hirayama
  • Patent number: 4973739
    Abstract: 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: Grant
    Filed: April 12, 1989
    Date of Patent: November 27, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Seiji Nagasawa, Hideo Ikarashi, Yoshio Kawai, Hiroyuki Hirayama
  • Patent number: 4950788
    Abstract: 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: Grant
    Filed: February 23, 1989
    Date of Patent: August 21, 1990
    Assignee: Allied Colloids Limited
    Inventors: David Farrar, Peter Flesher
  • Patent number: 4668818
    Abstract: 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: Grant
    Filed: June 18, 1985
    Date of Patent: May 26, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Hayden I. Lipp, Richard H. Squire
  • Patent number: 4645856
    Abstract: 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: Grant
    Filed: April 15, 1985
    Date of Patent: February 24, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventor: Thomas Herold
  • Patent number: 4596889
    Abstract: 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: Grant
    Filed: February 22, 1985
    Date of Patent: June 24, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Kroener, Walter Goetze
  • Patent number: 4558120
    Abstract: 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: Grant
    Filed: December 27, 1983
    Date of Patent: December 10, 1985
    Assignee: The Dow Chemical Company
    Inventors: Donald A. Tomalia, James R. Dewald
  • Patent number: 4529816
    Abstract: 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: Grant
    Filed: February 13, 1984
    Date of Patent: July 16, 1985
    Assignee: E. I. Du Pont De Nemours and Company
    Inventors: Raymond L. DeColibus, Jan J. van Heiningen, Thomas F. Veerkamp
  • Patent number: 4480116
    Abstract: 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: Grant
    Filed: March 2, 1983
    Date of Patent: October 30, 1984
    Assignee: Eastman Kodak Company
    Inventors: Ambrose J. Clonce, Michael Palmer, Samuel L. Gott
  • Patent number: 4450112
    Abstract: 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: Grant
    Filed: November 25, 1981
    Date of Patent: May 22, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Stanley S. Wreford
  • Patent number: 4408067
    Abstract: 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: Grant
    Filed: July 28, 1981
    Date of Patent: October 4, 1983
    Assignee: Nitto Chemical Industries, Ltd.
    Inventors: Tomio Nakamura, Shunichi Doi
  • Patent number: 4161609
    Abstract: 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: Grant
    Filed: September 14, 1977
    Date of Patent: July 17, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard D. Cramer
  • Patent number: 4092339
    Abstract: 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: Grant
    Filed: November 19, 1975
    Date of Patent: May 30, 1978
    Assignee: The Dow Chemical Company
    Inventors: Violete L. Stevens, Arthur R. Sexton, Frederick P. Corson