Process Which Includes Forming The Unsaturation Patents (Class 564/205)
  • Publication number: 20140309451
    Abstract: A process for producing high purity 3-hydroxypropionic acid from a fermentation cell broth is described. The 3-hydroxypropionic acid can be converted to a variety of products, such as acrylamide, 3-hydroxypropionic esters, acrylic esters, and 3-HP amide. This process features a high degree of product flexibility, limited or no solvent recycle, discrete waste streams, an efficient water removal process, and efficient recovery of products and solvents with proven and scalable equipment.
    Type: Application
    Filed: March 12, 2014
    Publication date: October 16, 2014
    Applicant: OPX Biotechnologies, Inc.
    Inventors: Robert TENGLER, David DeCOSTER
  • Publication number: 20130345470
    Abstract: A process for producing high purity 3-hydroxypropionic acid from a fermentation cell broth is described. The 3-hydroxypropionic acid can be converted to a variety of products, such as acrylamide, 3-hydroxypropionic esters, acrylic esters, and 3-HP amide. This process features a high degree of product flexibility, limited or no solvent recycle, discrete waste streams, an efficient water removal process, and efficient recovery of products and solvents with proven and scalable equipment.
    Type: Application
    Filed: June 20, 2012
    Publication date: December 26, 2013
    Applicant: OPX Biotechnologies, Inc.
    Inventors: Robert Tengler, David DeCoster
  • Patent number: 8410305
    Abstract: Highly efficient methods are provided for preparing key intermediates in the synthesis of epothilones and use new alane reagents which are broadly applicable and can provide selected components having a variety of substituents groups.
    Type: Grant
    Filed: November 12, 2008
    Date of Patent: April 2, 2013
    Assignee: Kosan Biosciences Incorporated
    Inventors: Yue Chen, Yong Li
  • Publication number: 20120116116
    Abstract: Provided is an amide ester that is useful as an intermediate manufacturing product for an aroma compound such as spilanthol or the like. Also provided is a spilanthol manufacturing method using said amide ester. High-purity spilanthol can be manufactured by reacting an amide ester represented by general formula (1) with a basic compound. (In the formula, R1 represents a phenyl group that may be substituted with a C1-6 alkyl group and either a C1-4 alkyl group, a C1-4 alkoxy group, or a halogen atom; R2 represents a C1-8 hydrocarbon group; and the wavy lines represent cis configurations, trans configurations, or a mixture of the two configurations.
    Type: Application
    Filed: July 14, 2010
    Publication date: May 10, 2012
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Shigeru Tanaka, Kenya Ishida, Kenji Yagi, Hideo Ujihara
  • Publication number: 20090131657
    Abstract: The present invention relates to a process for preparing N-(1-alkenyl)carboxamides of the formula I, which comprises reacting a carboxamide of the formula II with an alkyne of the formula III in the presence of a catalyst selected from among carbonyl complexes, halides and oxides of rhenium, manganese, tungsten, molybdenum, chromium and iron.
    Type: Application
    Filed: June 4, 2007
    Publication date: May 21, 2009
    Applicant: BASF SE
    Inventors: Wolfgang Staffel, Roland Kessinger, Jochem Henkelmann, Stefan Kashammer
  • Patent number: 7183432
    Abstract: A method of synthesizing diacetylenic amides is described. The key steps of the invention include the reaction of an aldehyde with the monoanion of a diacetylene and the reductive removal of a propargylic alcohol. The invention offers the first known method of synthesizing diacetylenic amides that are naturally isolated from Echinacea through a direct and flexible route.
    Type: Grant
    Filed: March 29, 2005
    Date of Patent: February 27, 2007
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: George A. Kraus, Jaehoon Bae
  • Patent number: 7157603
    Abstract: The method of separating reversibly thermally precipitable oligomeric N-substituted (meth)acrylamides and conjugates thereof from aqueous solution includes thermally precipitating the oligomeric N-substituted (meth)acrylamides and the conjugates thereof from an aqueous solution in the presence of at least one salt and then filtering in the presence of at least one filter aid. The filter aid has a wet density of 0.2–0.3 g/cc and comprises?99% cellulose with fiber lengths<75 ?m (99%) and=?m (65%). The salt can be a potassium, sodium, ammonium, calcium and/or magnesium chloride, acetate and/or sulfate salt and can be present in the aqueous solution in a concentration between 0.01 M and 3 M.
    Type: Grant
    Filed: May 6, 2002
    Date of Patent: January 2, 2007
    Assignee: Polytag Technology SA
    Inventor: Frank Hilbrig
  • Patent number: 6750368
    Abstract: The present invention relates to a process for preparing sulphuric methacrylamide. The process can include adding sulphur trioxide and a second part of acetone cyanohydrin without sulfuric add to a reaction medium, after a first part of acetone cyanohydrin with sulphuric acid free of sulfur trioxide is mixed and dehydrated by heating.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: June 15, 2004
    Assignee: Atofina
    Inventors: Jean-François Croisy, Michel Tosi
  • Patent number: 6562963
    Abstract: The present invention is directed to a process for the preparation of a compound of formula (X-a) or a pharmaceutically acceptable salt form thereof, wherein: R1 is selected from the group consisting of: C1-5 alkyl substituted with 0-5 R1a, —(CH2)r—C3-10 cycloalkyl substituted with 0-5 R1a, and —(CH2)r-aryl substituted with 0-5 R1a. Compounds of Formula (X-a) are macrocyclic molecules containing anti-succinate residues which inhibit metalloproteinases such as aggrecanase, and the production of tumor necrosis factor (TNF). The anti-succinates are formed by an Ireland Claisen rearrangement of a silyl ketene acetal which proceeds with high stereoselectivity.
    Type: Grant
    Filed: July 31, 2001
    Date of Patent: May 13, 2003
    Inventors: Roberta L. Dorow, Silvio Campagna, Pasquale N. Confalone, Fuqiang Jin, Zhe Wang
  • Patent number: 6552226
    Abstract: A novel tandem acyl-Claisen rearrangement reaction is provided. An allylic reactant such as an allylic amine or an allylic thioether, having at least two functional groups that enable the reactant to undergo at least two successive Claisen rearrangement reactions, is reacted with an acid chloride in the presence of a Lewis acid catalyst composition composed of a Lewis acid and a second catalyst component selected from the group consisting of tertiary amines and non-nitrogenous bases. The stereochemistry of the reaction product is readily controlled by the positioning and size of substituents on the allylic reactant. The reaction may be carried out on a solid support, i.e., on the surface of a substrate suitable for conducting solid phase chemical reactions.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: April 22, 2003
    Assignee: The Regents of the University of California
    Inventor: David W. C. MacMillan
  • Patent number: 6506939
    Abstract: A process for the preparation of a mixture comprising a compound of formula (1) and a compound of formula (2) wherein R1 is an optionally substituted C1-20 alkyl, optionally substituted C3-4 alkenyl, optionally substituted C5-7 cycloalkyl or optionally substituted benzyl, R2 is an optionally substituted C1-20 alkyl, optionally substituted C3-4 alkenyl or optionally substituted C5-7 cycloalkyl, A is either S or NR3, R3 is an optionally substituted C1-20 alkyl, optionally substituted C3-4 alkenyl or optionally substituted C5-7 cycloalkyl, or R2 and R3 together form a 5-7 membered ring which can contain an oxygen atom, R4 is hydrogen or methyl, R5 is an optionally substituted C1-20 alkyl, optionally substituted C3-4 alkenyl, optionally substituted C5-7 cycloalkyl or optionally substituted benzyl and, R6 is hydrogen or an optionally substituted C1-20 alkyl, optionally substituted C3-4 alkenyl or optionally substituted C5-7 cycloalkyl, or R5 and R6 together form a 5-7 membered ring which can cont
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: January 14, 2003
    Assignee: Ciba Specialty Chemicals Water Treatments Ltd.
    Inventors: Peter Stuart Littlewood, Michael Singh
  • Patent number: 6166253
    Abstract: A process for producing N-(1-alkoxyethyl)carboxylic amides by reacting alcohols of 1-5 carbon atoms with N-vinylcarboxylic amides in the presence of an acidic catalyst, or by utilizing unreacted starting material, unreacted intermediate or unrecovered product for synthesis of N-(1-alkoxyethyl)carboxylic amides. A process for producing N-(1-alkoxyethyl)carboxylic amides by adding a water-soluble strong acid during reaction between a carboxylic amide and a starting material containing acetaldehyde and alcohol and/or a starting material containing an acetal, in an amount of 2.times.10.sup.-3 to 3.times.10.sup.-1 equivalents to 1 mole of the carboxylic amide in the starting material, and using a strongly acidic ion-exchange resin as the catalyst.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: December 26, 2000
    Assignee: Showa Denko K.K.
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Etsuko Mitarai
  • Patent number: 5852214
    Abstract: A process for producing N-(1-alkoxyethyl)carboxylic amides by reacting alcohols of 1-5 carbon atoms with N-vinylcarboxylic amides in the presence of an acidic catalyst, or by utilizing unreacted starting material, unreacted intermediate or unrecovered product for synthesis of N-(1-alkoxyethyl)carboxylic amides. A process for producing N-(1-alkoxyethyl)carboxylic amides by adding a water-soluble strong acid during reaction between a carboxylic amide and a starting material containing acetaldehyde and alcohol and/or a starting material containing an acetal, in an amount of 2.times.10.sup.-3 to 3.times.10.sup.-1 equivalents to 1 mole of the carboxylic amide in the starting material, and using a strongly acidic ion-exchange resin as the catalyst.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: December 22, 1998
    Assignee: Showa Denko K.K.
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Tetsuo Kudo, Etsuko Mitarai
  • Patent number: 5723665
    Abstract: A process for producing an ethenyl amide compound, which comprises reacting a Schiff base compound having a carbon atom adjacent to a carbon atom constituting an imino group and at least one hydrogen atom on the carbon atom with an acylhalide at a reduced pressure while removing by-produced hydrogen halide by distillation to produce an ethenyl amide compound having an amide bond in the molecule and a double bond between carbons at .alpha.-position and .beta.-position with respect to the nitrogen atom of the amide bond.
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: March 3, 1998
    Assignee: Tokuyama Corporation
    Inventors: Shozo Kato, Shigeo Tamura, Toshio Kitajima, Noriyuki Fukada
  • Patent number: 5587515
    Abstract: A process for producing N-monosubstituted acrylamides in high yields without forming by-products. The process comprises preparing a .beta.-dialkylamino-(methyl)propionic ester by the reaction of a (meth)-acrylic ester with a specified dialkylamine, converting the formed ester into an N-monosubstituted .beta.-dialkylamino(methyl)propionamide by the reaction thereof with a primary amine in the presence of sodium methoxide, and thermally decomposing the amide under a reduced pressure.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: December 24, 1996
    Assignee: Kohjin Co., Ltd.
    Inventors: Yuuichi Takao, Hidetoshi Oogami
  • Patent number: 5567716
    Abstract: Traumatic acid salts, wherein B is a cation selected from:a) a quaternary ammonium,b) a cation of a linear or branched C.sub.1 -C.sub.20 mono-, di- or trialkanolamine,c) a cation of a biologically active primary, secondary or tertiary amine,d) silver or zinc cation,and relative pharmaceutical compositions administrable by topical or parenteral route For the therapeutic treatment of cutaneous pathologies in which it is important to associate an a bacteriostatic, antibiotic, antifungal or an antiviral activity, to the cicatrizant effect, typical of traumatic acid.
    Type: Grant
    Filed: November 19, 1993
    Date of Patent: October 22, 1996
    Assignee: Lifegroup S.p.A.
    Inventors: Francesco Della Valle, Silvana Lorenzi, Gabriele Marcolongo
  • Patent number: 5538998
    Abstract: There are provided with a novel N-substituted-3-halopropiolamide compound, a method of producing the compound, and a composition for controlling noxious organisms containing the compound. The present compound exhibits superior antimicrobial and antifungal effects. Pest control agents containing the compound can advantageously be used for wide applications.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: July 23, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshihiro Sugihara, Toshiro Yamashita, Sachio Shibata, Koichi Matsumura, Yosei Kuwazuru
  • Patent number: 5312984
    Abstract: A continuous process for making N,N-dimethylacrylamide (NNDMA) is disclosed which uses a commodity chemical, namely vinyl chloride (VCl), which is amidated with dimethylamine (DMA) and carbon monoxide in the presence of a supported palladium(O) triorganophosphine catalyst used under conditions where the ratio of P/Pd is critical. The continous process unexpectedly provides the catalyst with long life because the reaction can be carried out in a moving bed of catalyst in the presence of enough acetonitrile solvent to prevent deposition of DMA.HCl, formed during the reaction, in the pores of the catalyst support.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: May 17, 1994
    Assignee: The B. F. Goodrich Company
    Inventor: Paul P. Nicholas
  • Patent number: 5180851
    Abstract: This invention relates to an improved process for the formation of N-(l-alkoxyalkyl)amides with coproduction of alkylidene bisamides. The N-(l-alkoxyalkyl)formamides of this invention are prepared by reacting formamide with an acetal or hemiacetal carboxylate ester represented by the formulas below in the presence of a solid acid ion exchange resin wherein the acid groups have been neutralized with an amine compound having a pKa (as the protonated amine in water) from about 4 to 9. The hemiacetal ester is represented by formula I and the acetal is represented by formula II. ##STR1## In the above formulas, R is C.sub.1 -C.sub.8 alkyl, aralkyl or aryl; R.sub.1 and R.sub.2 are C.sub.1 -C.sub.8 alkyl, or aryl; and R.sub.3 is secondary or tertiary alkyl having from 3-8 carbon atoms.
    Type: Grant
    Filed: March 21, 1991
    Date of Patent: January 19, 1993
    Assignee: Air Products and Chemicals Inc.
    Inventors: Mark L. Listemann, Robert K. Pinschmidt, Jr.
  • Patent number: 5177264
    Abstract: An N-substituted dialkylacetal (meth)acrylamide of formula II: ##STR1## wherein n represents 3 or 4; R.sub.1 represents hydrogen or methyl; and R.sub.2 represents an alkyl of 1 to 3 carbon atoms is prepared by thermally decomposing an aminoacetal derivative represented by Formula I: ##STR2## wherein n, R.sub.1 and R.sub.2 are as defined above, in the presence of a base.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: January 5, 1993
    Assignee: Ajinomoto Co., Inc.
    Inventor: Yasuhiro Kimura
  • Patent number: 5166434
    Abstract: A process is disclosed for preparing aromatic-substituted unsaturated amides. The process comprises treating a compound of the formula ##STR1## where Ar is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.12 linear or branched alkoxy or haloalkyl, the alkyl moiety being C.sub.1 to C.sub.6 linear or branched or the group ##STR2## where Ar' is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.12 alkoxy or haloalkyl, the alkyl moiety being C.sub.1 to C.sub.6 linear or branched; and R and R' are the same or different and are hydrogen or C.sub.1 to C.sub.12 linear or branched alkyl and can also be phenyl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: November 24, 1992
    Assignee: Ethyl Corporation
    Inventor: Kathleen S. Laurenzo
  • Patent number: 5159113
    Abstract: A unique two-step process is disclosed for the surprisingly high rate of amidation of vinyl chloride (VCl) with carbon monoxide and certain amines catalyzed by an effective amount of monodentate tertiary phosphonium complexes of Pd(0). The rate is orders of magnitude faster than that of other monochloroalkenes. When compared with the three chloropropenes, the simplest alkyl-substituted derivatives of VCl, rates differ by a factor of about 40 to 70 with ammonia as the amine. The reaction product with VCl is mainly the Michael adduct of the amine with the acrylamide produced. However, the chloroprenes give the propenamides with retention of configuration in the case of cis- and trans-1-chloropropene, and no adduct formation. The formation of this adduct has an important influence on catalyst stability since it can compete with the addition of the tertiary-phosphonium ligand from the catalyst complex.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: October 27, 1992
    Assignee: The B. F. Goodrich Company
    Inventor: Peter P. Nicholas
  • Patent number: 4933449
    Abstract: The invention provides a process for the preparation of 3,3-diaryl acrylic acid amides of the formula ##STR1## in which A, B and Q are as defined in the specification, characterized by condensing a compound of formula ##STR2## with a compound of formulaZCH.sub.2 --CO--Q (III)in which Z represents a hydrogen or halogen atom, and, if an intermediate compound is formed of formula ##STR3## dehydrating the intermediate compound.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: June 12, 1990
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventor: Jurgen Curtze
  • Patent number: 4898977
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4835312
    Abstract: An N-substituted amide compound is produced with a high yield by initiating a reaction among a starting amide compound such as a saturated or unsaturated, aliphatic or aromatic carboxylic acid amide, a halogen-substituted compound such as an alkyl halide and a strongly basic substance while maintaining the basic substance in a suspended state.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: May 30, 1989
    Assignee: Mitsui Chemicals, Incorporated
    Inventors: Hiroshi Itoh, Toshimi Nakagawa, Atsuhiko Nitta
  • Patent number: 4644083
    Abstract: The present invention relates to a process for the production of N-substituted .alpha.,.beta.-unsaturated carboxylic acid amides, which proceeds from the .alpha.,.beta.-unsaturated carboxylic acid amide that is unsubstituted at the amido nitrogen, which forms the Michael adduct initially by conversion with a polyvalent alcohol having a boiling point of >/=150.degree. C., converts this with a primary or secondary amine with elimination of ammonia to form N-substituted carboxylic acid amide with a protected double bond, the polyvalent alcohol being subsequently eliminated from this product at high temperatures, with formation of the N-substituted .alpha.,.beta.-unsaturated carboxylic acid amide.
    Type: Grant
    Filed: January 25, 1985
    Date of Patent: February 17, 1987
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Kurt Dahmen, Erich Kuster, Richard Mertens, Helmut Brehm
  • Patent number: 4605740
    Abstract: The present invention relates to a process for the production of N-substituted acrylic acid amides by conversion of 2-carboalkoxy-t-oxabicyclo(2,2,1)hept-5-enes with primary or secondary amines to 2-carboxamide-7-oxabicyclo(2,2,1)hept-5-enes and the thermal decomposition of the latter, preferably in the presence of Lewis acids and in a vacuum, to furane and N-substituted acrylic acid amides. The process according to the invention results in high purity N-substituted acrylic acid amides that are, in the main, free of bifunctional monomers which would disrupt the subsequent polymerization of the N-substituted acrylic acid amides by undesired cross-linking.
    Type: Grant
    Filed: September 22, 1983
    Date of Patent: August 12, 1986
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventor: Alfons Landscheidt
  • Patent number: 4570018
    Abstract: A novel chemical, fluorochlorocyclopropane (I) of the following formula: ##STR1## is prepared by the addition of fluorochlorocarbene to the corresponding olefin (II) of the following formula:CH.sub.2 .dbd.CR.sup.1 -R.sup.2The compound is a useful intermediate for synthesizing some chemicals, e.g., some cephalosporins.(wherein R.sup.1 is hydrogen, halogen, 1 to 8C alkylamino, alkoxy, or alkylthio andR.sup.2 is halogen, 1 to 8C alkylamino, alkoxy, or alkylthio).
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: February 11, 1986
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
  • Patent number: 4565889
    Abstract: N-(3-dimethylaminopropyl)methacrylamide is prepared by the non-catalytic pyrolysis of N-(3-dimethylaminopropyl)-3-dimethylaminopropyl-2-methyl propionamide in a closed reactor. The N-(3-dimethylaminopropyl)methacrylamide is not removed from the reaction mixture until the pyrolysis reaction is completed.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: January 21, 1986
    Assignee: Texaco Inc.
    Inventors: David R. Livingston, Edward E. McEntire, Edward C. Nieh
  • Patent number: 4554377
    Abstract: The invention relates to the preparation of N-.alpha.-alkoxyethyl-carboxylic acid amides from dimethyl acetal and a carboxylic acid amide such as acetamide and to the preparation of secondary N-vinyl carboxylic acid amides such as N-vinyl acetamide therefrom.The reaction of dimethyl acetal and the carboxylic acid amide involves an equilibrium disproportionation wherein excess dimethyl acetal is used in sufficient amounts, e.g., in a molar ratio of from about 2 to 60:1 mole ratio, so as to force the equilibrium to the desired N-.alpha.-alkoxyethyl-carboxylic acid amide intermediate product. Equilibrium is reached in about 0.1 to 150 hours at a temperature about 0.degree. to 100.degree. C. The intermediate N-.alpha.-alkoxyethyl-carboxylic acid amide is pyrolyzed in accordance with a known pyrolysis reaction so as to obtain the corresponding N-vinyl acetamide.
    Type: Grant
    Filed: July 16, 1984
    Date of Patent: November 19, 1985
    Assignee: Celanese Corporation
    Inventors: Robert W. Stackman, Richard H. Summerville, deceased, James E. Summerville, Jr., heir
  • Patent number: 4408073
    Abstract: The invention relates to a process for the preparation of .alpha., .beta.-unsaturated N-substituted carboxylic acid amides, novel .alpha., .beta.-unsaturated N-substituted carboxylic acid amides, a process for the polymerization of these novel .alpha., .beta.-unsaturated N-substituted carboxylic acid amides, including the polymers, and the use of these polymers as sedimentation, flocculating, dewatering and retention aids, as additives for mineral oils, and as ion exchangers.The .alpha., .beta.-unsaturated N-substituted carboxylic acid amides are prepared by transamidation of .beta.-hydroxy or .beta.-alkoxy carboxylic acid amides with primary amines and heating of the N-substituted .beta.-hydroxy or .beta.-alkoxy carboxylic acid amides obtained as intermediate products in the vapor phase in the presence of catalysts. Primary amines are preferably used in the conversion which have no hydrogen beta to the amino group.These .alpha.,.beta.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: October 4, 1983
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Bernhard Goossens, Erich Kuster, Kurt Dahmen, Eduard Barthell
  • Patent number: 4347379
    Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4330482
    Abstract: In the process for the production of a halogenoalkene of the formula ##STR1## in which R.sup.1 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl or aryl radical or an optionally substituted heterocyclic radical,R.sup.2 represents a halogen atom, a cyano group, an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkenyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl or aminocarbonyl radical or an optionally substituted heterocyclic radical, andX is a halogen atom,in which an .alpha.-hydroxy-phosphonic acid ester of the formula ##STR2## in which R.sup.3 each independently is an alkyl or phenyl radical, or the two radicals R.sup.3 together are an alkanediyl (alkylene) radical,is reacted with a phosphorus-containing olefinating agent of the formula ##STR3## in which Z.sup.1 is the phosphorus-containing radical ##STR4## R.sup.4 and R.sup.5 each independently is an alkyl, phenyl, alkoxy or phenoxy radical or together are an alkanedioxy radical, andR.
    Type: Grant
    Filed: December 18, 1980
    Date of Patent: May 18, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hellmut Hoffmann
  • Patent number: 4312998
    Abstract: The invention relates to a process for the preparation of N-substituted acrylamides of the general formula ##STR1## wherein Y denotes a bivalent straight - or branched chain radical with 2 to 30, preferably 2 to 18, and particularly 2 to 6 carbon atom-, preferably a group of the formula (Y.sub.1).sub.m -(Y.sub.2).sub.n -(Y.sub.3).sub.t, in whichY.sub.1, Y.sub.2 and Y.sub.3 each stands for an alkylene group or the radical of a cyclic organic ring system with 5 or 6 carbon atoms, and the sum of m, n, and t is 2 or 3, and R.sub.1 denotes hydrogen or the radical of an amine of the formula N(R.sub.2) (R.sub.3),whereinR.sub.2 and R.sub.3 stand for alkyl radicals with 1 to 4 carbon atoms, which method is characterized in that dihydracrylic acid amide of the general formula ##STR2## is transmitted with amines of the general formulaH.sub.2 N--(Y)--R.sub.1 (III)with elimination of ammonia and the resulting N-substituted .beta.
    Type: Grant
    Filed: May 2, 1980
    Date of Patent: January 26, 1982
    Assignee: Chemische Fabrik
    Inventors: Erich Kuster, Bernhard Goossens, Kurt Dahmen, Eduard Barthell
  • Patent number: 4302584
    Abstract: A process for the preparation of 3,3-dimethyl-pent-3-enoic acid amides of the formula I ##STR1## where R.sup.1 and R.sup.2 may be identical or different and each is alkyl of 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together with the nitrogen on which they are present as substituents form a 5-membered or 6-membered saturated ring which may contain a further hetero-atom,wherein an acetamido-acetal or ketene-acetal-aminal is reacted with 3-methyl-but-2-en-1-ol at from 80.degree. to 220.degree. C., in the presence or absence of an inert organic solvent. The products are valuable intermediates for the preparation of insecticidal cyclopropanecarboxylic acid esters.
    Type: Grant
    Filed: August 7, 1980
    Date of Patent: November 24, 1981
    Assignee: BASF Aktiengesellschaft
    Inventor: Klaus Halbritter
  • Patent number: 4287363
    Abstract: A catalytic process for the preparation of N-(alkylaminoalkyl)acrylamides is disclosed which comprises subjecting a corresponding .beta.-aminopropionamide to a temperature of about 100.degree.-250.degree. C. in presence of a catalyst comprising a magnesium, calcium or aluminum salt of a strong acid, and separating the N-(alkylaminoalkyl)acrylamide from the reaction product. The corresponding .beta.-aminopropionamide compounds can be prepared by mixing and reacting at least 2 moles of an alkylaminoalkyl amine with an acrylic acid or ester compound. The inventive process provides the production of the N-(alkylaminoalkyl)acrylamides in high yields with minimal back-addition or polymerization.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: September 1, 1981
    Assignee: Texaco Inc.
    Inventor: Edward E. McEntire
  • Patent number: 4286105
    Abstract: An inexpensive and nonhazardous process for the preparation of an amide wherein an organic acid reacting with an aryl amine to form an intermediate hydroxy aryl amide and then dehydrating the hydroxy aryl amide to form a .alpha., .beta. unsaturated amide.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: August 25, 1981
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker
  • Patent number: 4267372
    Abstract: Reaction of a beta-aminopropionamide with an acrylic acid or its derivative provides an N-substituted acrylamide monomer having cationic substituents attached thereto. The instant reaction occurs under mild processing conditions at a temperature between about 160.degree. C. and 230.degree. C.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: May 12, 1981
    Assignee: American Cyanamid Company
    Inventors: Alan S. Rothenberg, Michael N. Desmond
  • Patent number: RE37555
    Abstract: The invention relates to a method of producing a mixture of a quaternary ammonium compound, fatty acid, fatty acid ester and tertiary amine salt in situ which is a highly functional mixture that is manufactured in a single step reaction whereby quaternization is completed without the aid of solvents, especially flammable solvents. The single step reaction process eliminates separate blending of individual components. The compositions obtained can be used as fabric softeners, in modified clays, as hair treating compounds and as disinfectants.
    Type: Grant
    Filed: June 11, 1999
    Date of Patent: February 19, 2002
    Assignee: Goldschmidt Chemical Company
    Inventors: Jeannene A. Ackerman, Michael Miller, David E. Whittlinger