Patents Examined by P. J. Killos
  • Patent number: 4013714
    Abstract: Compounds represented by the formula ##EQU1## wherein Rx is ##EQU2## AND A is hydrogen, methyl, ethyl, CH.sub.2 OH or RxOH; M being alkali metal, ammonium, alkyl ammonium, or alkanol ammonium and Rz being hydrogen, alkyl, phenyl, phenyl alkyl, alkoxy alkyl, alkoxy phenyl or alkoxy phenyl alkyl are useful as complexing agents and/or detergency builders. The ester and acid forms of these compounds are useful as intermediates for their preparation.
    Type: Grant
    Filed: December 19, 1973
    Date of Patent: March 22, 1977
    Assignee: Monsanto Company
    Inventor: Kent P. Lannert
  • Patent number: 3966802
    Abstract: The present invention relates to a process for preparing acrylic acid by oxidizing acrolein and to an oxidation catalyst.More particularly, the present invention relates to a catalyst and a process for preparing acrylic acid by oxidizing acrolein or a mixed acrolein gas obtained by vapor phase oxidation of propylene with molecular oxygen in the presence of an oxidation catalyst of the empirical formula:Mo.sub.a V.sub.b T.sub.c A.sub.d O.sub.ewherein Mo, V and O represent molybdenum, vanadium and oxygen, respectively, T represents tungsten or antimony, A represents an alkali metal, and a, b, c, d and e represent number of atoms of Mo, V, T, A and O, respectively, and when a is 12, b is 0.5 to 6, c is 0 to 6, d is 0.01 to 1.5, preferably, 0.15 to 1.2 and e is naturally determined by the valence requirements of the other elements present.
    Type: Grant
    Filed: April 19, 1974
    Date of Patent: June 29, 1976
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shigeo Takenaka, Hitoshi Shimizu, Masanobu Ogawa
  • Patent number: 3966797
    Abstract: Dinorbornene compounds, many of them novel, have been found to form polymers having a ladder structure. The dinorbornene compounds and dinorbornene polymers with other polymers such as the polyolefins, vinyl polymers, acrylic polymers, polyesters, polyamides, polyethers, polyureas, polyurethanes, natural polymers, etc., are readily crosslinked by irradiation.
    Type: Grant
    Filed: May 26, 1971
    Date of Patent: June 29, 1976
    Assignee: Union Carbide Corporation
    Inventors: Henry Octave Colomb, Jr., David John Trecker, Thomas Kemper Brotherton
  • Patent number: 3965149
    Abstract: A method for recovering methyl methacrylate from a mixture of polymeric materials containing poly (methyl methacrylate) which comprises contacting the mixture with a boiling C.sub.5 - C.sub.8 alkane, separating an insoluble residue containing poly (methyl methacrylate) from the alkane and its extract, extracting poly (methyl methacrylate) from such insoluble residue with boiling acetone, separating the poly (methyl methacrylate) from the acetone, and recovering the methyl methacrylate monomer from such poly (methyl methacrylate) by pyrolysis. In a preferred embodiment, the poly (methyl methacrylate) containing solid obtained after the acetone extraction is compressed under elevated temperatures and pressures prior to pyrolysis. The method can be stopped prior to the pyrolysis step when it is desired to recover only the poly (methyl methacrylate).
    Type: Grant
    Filed: November 4, 1974
    Date of Patent: June 22, 1976
    Assignee: Ford Motor Company
    Inventor: Lee R. Mahoney
  • Patent number: 3956382
    Abstract: A process for the production of ether polycarboxylic acids comprising reacting alkali metal salts of ether carboxylic acids with carbon dioxide in the presence of (1) an alkaline compound selected from the group of alkali metal carbonates, bicarbonates and hydroxides and (2) optionally, heavy metal catalysts and inert diluents at temperatures of 200.degree.C to 350.degree.C under pressure, acidify the resulting alkali metal salt of an ether polycarboxylic acid and recovering said ether polycarboxylic acid.
    Type: Grant
    Filed: October 21, 1974
    Date of Patent: May 11, 1976
    Assignee: Henkel & Cie G.m.b.H.
    Inventor: Horst-Jurgen Krause
  • Patent number: 3956381
    Abstract: A process for the production of ether polycarboxylic acids comprising reacting alkali metal salts of ether carboxylic acids with carbon dioxide in the presence of (1) an alkali metal alkyl carbonate and (2) optionally, heavy metal catalysts and inert diluents at temperatures of 200.degree.C to 350.degree.C under pressure, acidify the resulting alkali metal salt of an ether polycarboxylic acid and recovering the ether polycarboxylic acid.
    Type: Grant
    Filed: October 21, 1974
    Date of Patent: May 11, 1976
    Assignee: Henkel & Cie G.m.b.H.
    Inventor: Horst-Jurgen Krause
  • Patent number: 3956366
    Abstract: A process for making N-monochloro or bromo monosubstituted urea where a urea RNH--CO--NH.sub.2 is suspended in liquid water at 0.degree.C-60.degree.C and reacted with free chlorine or free bromine, at least 2 g. atoms per mole of urea, preferably in the presence of an acid acceptor such as zinc oxide; R may be alkyl having 3 carbon atoms, cycloalkyl, aralkyl, alkoxycarbonyl, aryloxycarbonyl or acyl.New compounds of the formula R.sub.d --NX--CO--NX'H where X and X' are different and are (1) chloro or bromo and (2) hydrogen and R.sub.d is alkyl or cycloalkyl, 3-15 carbon atoms, or R.sub.1 C(O)--, where R.sub.1 is aliphatic, cycloaliphatic, aryl, alkoxy or aryloxy, each of not more than 10 carbon atoms and when X is H, X' is Cl or Br and R.sub.d is alkyl or cycloalkyl and when X is Cl or Br, X' is H and R.sub.d is R.sub.1 C(O)--.
    Type: Grant
    Filed: June 28, 1973
    Date of Patent: May 11, 1976
    Assignee: Pennwalt Corporation
    Inventors: Chester Stephen Sheppard, Leonard Earnest Korczykowski
  • Patent number: 3954749
    Abstract: Provided as catalysts for the formation of cellular urethane polymers ranging from flexible to rigid foams, are beta-amino carbonyl compounds wherein carbonyl is present as an amido or carboxylic acid ester group and the beta-amino group is present as dialkylamino or an N-morpholino or N,N'-piperazino heterocyclic nucleus. Effective in the catalysis of the water-isocyanate reaction, these beta-amino amides and beta-amino esters are used with particular advantage in the manufacture of water-blown flexible foams, both molded and free-rise, including high-resilience and flame-retarded foam. The beta-amino carbonyl catalysts allow for the formation of foam products essentially free of the odor associated with amines such as N-ethylmorpholine. In view of this highly desirable characteristic and their other beneficial properties, the catalysts of the invention are advantageously employed as direct replacements for N-ethylmorpholine in high-resilience and other foam formulations.
    Type: Grant
    Filed: April 23, 1974
    Date of Patent: May 4, 1976
    Assignee: Union Carbide Corporation
    Inventors: David Charles Priest, Michael Ray Sandner, David John Trecker
  • Patent number: 3953504
    Abstract: An optically active enantiomer of tartaric acid or a salt thereof is racemized by mixing meso-tartaric acid or a salt thereof with a solution of an optically active enantiomer of tartaric acid or a salt thereof in a molar ratio of 0.2 - 0.5 and thereafter heating the mixture.
    Type: Grant
    Filed: March 18, 1975
    Date of Patent: April 27, 1976
    Assignees: Nippon Peroxide Co., Ltd., Showa Chemical Co., Ltd.
    Inventors: Minoru Saotome, Yoshikazu Yamamoto, Nobuo Watani, Ryuichi Kayama
  • Patent number: 3952034
    Abstract: Olefins and acetylenes are carbonylated to a carboxylic acid or ester using a homogenous catalyst system comprising palladium together with iron or a metal of Groups IVA, VA or IIIB, the catalyst being either a polynuclear complex incorporating both metals, or a mixture of a soluble palladium salt and metal halide. Starting with cyclic di-olefins, such as cyclo-octadiene, the product cycloalkenyl carboxylic acid or ester may be cleaved to give acyclic dicarboxylic acids, such as azelaic acid.
    Type: Grant
    Filed: December 3, 1973
    Date of Patent: April 20, 1976
    Assignee: Imperial Chemical Industries Limited
    Inventors: David Thomas Thompson, Reginald Jackson
  • Patent number: 3951969
    Abstract: Plant growth regulating compounds are N-substituted-P-(2-chloroethyl)-phosphonamidic esters of the formula: ##EQU1## wherein R is cycloalkyl, R.sub.1 is hydrogen or cycloalkyl or R and R.sub.1 together form a heterocyclic ring such as morpholine, piperidine or pyrrolidine and R.sub.2 is alkyl or haloalkyl. They are prepared by the reaction of 2-chloroethylphosphonohalidic esters with the appropriate secondary amine.
    Type: Grant
    Filed: February 12, 1974
    Date of Patent: April 20, 1976
    Assignee: GAF Corporation
    Inventors: David I. Randall, Robert W. Wynn
  • Patent number: 3952054
    Abstract: Diglycolic acid is prepared by oxidation of p-dioxanone.
    Type: Grant
    Filed: December 5, 1974
    Date of Patent: April 20, 1976
    Assignee: Monsanto Company
    Inventor: Chung Y. Shen
  • Patent number: 3950332
    Abstract: N-substituted amino-N-nitroso-aminoacetamides, e.g., .alpha.-(N-morpholino-N-nitrosoamino)acetamide, are prepared by hydrolyzing the corresponding 3-N-substituted amino-sydnonimines and have been found to be useful as hypotensive/anti-hypertensive and anti-anginal agents.
    Type: Grant
    Filed: February 14, 1973
    Date of Patent: April 13, 1976
    Assignee: Sandoz, Inc.
    Inventor: Paul L. Anderson
  • Patent number: 3950410
    Abstract: In the oxidation of a liquid alcohol and/ketone with nitric acid to a carboxylic acid, especially of a mixture of cyclohexanol and cyclohexanone to adipic acid, temperature is controlled during the reaction in which gas is evolved by contacting the reaction mixture with a plurality of cooling surfaces vertically spaced from each other in such a way that the turbulence induced by the reaction inhibits the formation of bubbles upon the cooling surfaces. The cooling surfaces may be horizontally disposed banks of tubes through which water is passed.
    Type: Grant
    Filed: March 13, 1974
    Date of Patent: April 13, 1976
    Assignee: Imperial Chemical Industries Limited
    Inventor: Jose Lopez-Merono
  • Patent number: 3950399
    Abstract: A new compound, 1,4-diacyloxy-2,3-butanediol, having the general formula ##EQU1## where R is hydrogen atom or methyl group. The compound can be used above all as a crosslinking agent in the preparation of crosslinked hydrophilic polymeric gels. This compound can be prepared by opening the epoxy ring in such a way, that 1 mole of 1,2-3,4-diepoxybutane is treated with 2 moles of unsaturated acid of the general formula ##EQU2## where R has the aforementioned meaning.
    Type: Grant
    Filed: January 30, 1974
    Date of Patent: April 13, 1976
    Assignee: Ceskoslovenska akademie ved
    Inventors: Jiri Labsky, Josef Exner
  • Patent number: 3950405
    Abstract: A trans isomer of 4-cyanoncyclohexane-1-carboxylic acid or its lower alkyl ester is reduced in a solvent in the presence of a hydrogenating catalyst, and hydrolyzing the produced ester in case the starting trans-isomer is a lower alkyl ester, then the trans-4-aminomethyl-cyclohexane-1-carboxylic acid is recovered from the reaction mixture.
    Type: Grant
    Filed: June 4, 1969
    Date of Patent: April 13, 1976
    Assignee: Mitsubishi Chemical Industries Ltd.
    Inventors: Atsuji Okano, Shizuo Kadoya, Takeo Naito, Takaaki Aoyagi, Masao Shimizu
  • Patent number: 3950388
    Abstract: Organic compounds having a substituent represented by the formula ##EQU1## wherein M is alkali metal or ammonium which are useful complexing agents for metal and/or alkaline earth metal ions are prepared by reaction of a conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol with a bromo or iodo acetate ester and saponifying the resulting product.
    Type: Grant
    Filed: May 24, 1974
    Date of Patent: April 13, 1976
    Assignee: Monsanto Company
    Inventor: Kent P. Lannert
  • Patent number: 3950397
    Abstract: A process is provided for making a triester of citric acid wherein the cyanohydrin of an acetone dicarboxylic acid diester is reacted with 1 to 3 molar equivalents of an aliphatic alcohol having 1 to 4 carbon atoms and at least two molar equivalents of anhydrous hydrogen chloride in an inert halogenated organic solvent for the cyanohydrin diester at not above 50.degree.C. to form an imino ether, removing excess hydrogen chloride, adding water to form a two-phase system, separating the organic and water phases and recovering the resulting triester from the organic phase. The triester may be hydrolyzed into citric acid or a salt of citric acid in an acid or alkaline medium.
    Type: Grant
    Filed: December 6, 1974
    Date of Patent: April 13, 1976
    Assignee: Akzona Incorporated
    Inventor: Jan Gerardus Batelaan
  • Patent number: 3948985
    Abstract: Carboxymethyloxysuccinic acid is prepared by acidifying the calcium salt of carboxymethyloxysuccinic acid with sulfuric acid at a temperature of 40.degree.C to 80.degree.C; filtering off the CaSO.sub.4 .2H.sub.2 O by-product and concentrating the filtrate to give the purified acid. The calcium salt of carboxymethoxysuccinic acid is formed by reacting maleic acid and glycolic acid in aqueous media containing excess calcium hydroxide.
    Type: Grant
    Filed: October 11, 1974
    Date of Patent: April 6, 1976
    Assignee: FMC Corporation
    Inventors: John H. Blumbergs, Michael J. McCarthy, Joseph H. Finley, John M. Polkowski
  • Patent number: 3948986
    Abstract: A process for producing an alpha-hydroxy carboxylic acid which comprises contacting carbon monoxide with a saturated C.sub.2 -C.sub.16 aldehyde, water, and a catalyst comprising hydrogen fluoride in a reaction zone and under conditions effective to form an alpha-hydroxy carboxylic acid, including a temperature between 0.degree.C and 100.degree.C and a carbon monoxide partial pressure between 10 and 4000 psig.An alpha-alkoxy acid can be produced in the above reaction by using an alcohol instead of water.
    Type: Grant
    Filed: January 20, 1975
    Date of Patent: April 6, 1976
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki