Unsaturated Patents (Class 562/598)
  • Patent number: 4370488
    Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.
    Type: Grant
    Filed: June 18, 1981
    Date of Patent: January 25, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4346235
    Abstract: A novel fluorine-containing compound of the formulaR.sub.1 --A--R.sub.2whereinA is ##STR1## R.sub.1 and R.sub.2 are each hydrogen or R.sub.3 OOC--CH.sub.2).sub.n, while R.sub.1 and R.sub.2 may not be hydrogen at the same time; X is hydrogen or halogen; R.sub.3 is hydrogen or a lower alkyl group; m is an integer of 1 to 5; and n is an integer of 4 to 11, and a process for preparing the same.
    Type: Grant
    Filed: June 10, 1980
    Date of Patent: August 24, 1982
    Assignees: Okamura Oil Mill Limited, Daikin Kogyo Co., Ltd.
    Inventors: Noboru Sonoda, Shinji Murai, Kazuhisa Takii
  • Patent number: 4323695
    Abstract: The invention relates to a novel process for making phenyl fluoroacrylate monomer. The monomer is obtained by reaction of a fluoroacrylic salt with an halogenating agent, followed by condensation of the fluoroacryloyl halogenide with phenol and recovery of the phenyl fluoroacrylate. The obtained monomer is applicable to the manufacture of transparent polymers of high thermal stability.
    Type: Grant
    Filed: December 11, 1979
    Date of Patent: April 6, 1982
    Assignee: Office National d'Etudes et de Recherches
    Inventors: Bertrand Bloch, Chantal C. Meyer, Denis Charrier
  • Patent number: 4317926
    Abstract: In a process for producing acrylic acid which comprises contacting with water an acrylic acid-containing reaction product gas which has been obtained by the catalytic vapor phase oxidation of an olefinic compound of a general formula, CH.sub.2 .dbd.CHX, wherein X represents at least one group selected from the group consisting of CH.sub.
    Type: Grant
    Filed: January 15, 1979
    Date of Patent: March 2, 1982
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Takahisa Sato, Masao Baba, Michito Okane
  • Patent number: 4314842
    Abstract: This invention concerns certain substituted 1,3,4-thiadiazol-2-yl-4-hydroxy-1-methyl-2-imidazolidinones having herbicidal activity, their preparation, and the control of weeds therewith.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: February 9, 1982
    Assignee: PPG Industries, Inc.
    Inventor: Jerome M. Lavanish
  • Patent number: 4309357
    Abstract: Dienoic acids are prepared by reaction of salts of 3-butenoic acid and vinyl halides, in the presence of catalysts which are phosphinic complexes of rhodium or nickel.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: January 5, 1982
    Assignee: Montedison S.p.A.
    Inventors: Gian P. Chiusoli, William Giroldini, Giuseppe Salerno
  • Patent number: 4307232
    Abstract: Process for preparing the substituted phosphonoalkanoic acid of the formula ##STR1## wherein: R.sup.1 is alkyl of 1-8 carbon atoms, aralkyl of 7-10 carbon atoms, phenyl, or substituted phenyl of 6-10 carbon atoms;R.sup.2 is H, hydrocarbyl of 1-18 carbon atoms, or substituted hydrocarbyl of 1-18 carbon atoms, wherein in said hydrocarbyl groups the carbon atom attached to the ##STR2## moiety is substituted with two or three hydrogen atoms or is a carbon atom of an aromatic ring; andY is oxygen or sulfur,which process comprises contacting and reacting, at a temperature of about -70.degree. C. to about 125.degree. C., a pressure of about 1-100 atmospheres (0.1-10 MPa), and for a time sufficient to effect reaction, the phosphite ester of the formula ##STR3## wherein R.sup.1 and Y are as defined above, with the .alpha.-halocarboxylic acid of the formula R.sup.2 CHXCO.sub.2 H, wherein X is Cl, Br, or I and R.sup.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: December 22, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David R. Brittelli
  • Patent number: 4301186
    Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
  • Patent number: 4282373
    Abstract: Compounds of the formula (II): ##STR1## wherein X is halogen, hydroxyl or functionalized hydroxyl; Y is halogen, hydroxyl or alkoxy; R.sup.1 is a carboxylic acid group and ester thereof and amide derivative thereof or cyano; and R.sup.2 is hydrogen, a hydrocarbon, a heterocycle, a carboxylic acid group, a carboxylic acid ester, a carboxylic acid amide derivative, acyl, cyano, isocyano or an optionally substituted imine of the formula --CH.dbd.NZ or --N.dbd.CH.sub.2 wherein Z is hydrogen, alkyl, aryl, sulphonyl, --SR.sup.a, sulphoxide --SR.sup.a, or sulphonate --SR.sup.a wherein R.sup.a is alkyl of 1 to 6 carbon atoms or aryl, are useful as intermediates for the ultimate production of penicillins or cephalosporins.
    Type: Grant
    Filed: May 7, 1979
    Date of Patent: August 4, 1981
    Assignee: Beecham Group Limited
    Inventors: Angela W. Guest, Andrew W. Taylor, Robert Ramage
  • Patent number: 4267365
    Abstract: A process for the preparation of an oligomeric acrylic acid of the formulaCH.sub.2 .dbd.CH--COO[CH.sub.2 --CH.sub.2 --COO].sub.n Hwherein n represents a number from 1 to 6 is described wherein acrylic acid is heated in the presence of a polymerization inhibitor to a temperature of about 50.degree. to about 200.degree. C. The process can be carried out at sub-atmospheric pressure, atmospheric pressure or super-atmospheric pressure and in the presence or absence of a solvent.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: May 12, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kurt Findeisen
  • Patent number: 4265819
    Abstract: A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine,R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a cycloaliphatic ring with up to 7 carbon atoms, andR.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: May 5, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4260548
    Abstract: Low molecular weight ethylene homo and copolymer waxes are prepared by using a combination of (1) incremental addition of free radical catalyst (2) at high temperatures up to 150.degree. C. and (3) high pressures up to 3000 psi. Preferably molten aliphatic waxes are used as the solvent.
    Type: Grant
    Filed: June 4, 1979
    Date of Patent: April 7, 1981
    Assignee: Princeton Polymer Laboratories
    Inventors: Donald E. Hudgin, Thomas Zawadzki
  • Patent number: 4249015
    Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.
    Type: Grant
    Filed: January 26, 1979
    Date of Patent: February 3, 1981
    Assignee: Shell Oil Company
    Inventors: John A. Schofield, John E. Hawes
  • Patent number: 4242265
    Abstract: New indolylalkyl esters of mercaptoalkanoic acids, and salts thereof, which have the general formula ##STR1## are useful as hypotensive agents.
    Type: Grant
    Filed: January 10, 1979
    Date of Patent: December 30, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Peter C. Wade, Miguel A. Ondetti
  • Patent number: 4229354
    Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: October 21, 1980
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4218386
    Abstract: A process for hydrolyzing triglyceride having its carboxylic acid moieties containing from 6 to 26 carbon atoms involves reacting with water in the presence of low molecular weight displacing acid catalyst, strong acid catalyst and sufficient water to form water and oil phases, to produce carboxylic acids corresponding to said moieties and glycerine.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: August 19, 1980
    Assignee: The Procter & Gamble Company
    Inventors: Ted J. Logan, David C. Underwood, Tom C. Rheinecker
  • Patent number: 4210493
    Abstract: A method is disclosed for inhibiting the polymerization of acrylic and methacrylic acids at ambient or above ambient temperature, such as during preparation, purification or storage of the acids under substantially anaerobic conditions, by adding thereto a polymerization inhibiting amount of a compound having the formula:R--NOwhere R is alkyl or aryl, and if R is aryl, a hydroxyl group para to the NO group enhances inhibition.
    Type: Grant
    Filed: March 30, 1976
    Date of Patent: July 1, 1980
    Assignee: Rohm and Haas Company
    Inventors: Thomas Stewart, Richard F. Merritt
  • Patent number: 4201725
    Abstract: Methylamine derivatives of the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof, wherein R.sub.1 and R.sub.3 each represent a hydrogen atom or a straight- or branched-chain alkyl, alkenyl or alkynyl radical containing from 1 to 6 carbon atoms, R.sub.2 represents a straight- or branched-chain alkyl, alkenyl or alkynyl radical containing from 2 to 7 carbon atoms with the proviso that when R.sub.2 represents an alkenyl radical of the formula CH.dbd.CH--R.sub.6 or an alkynyl radical of the formula C.tbd.C--R.sub.6, in which R.sub.6 represents a hydrogen atom or a straight- or branched-chain alkyl radical of 1 to 5 carbon atoms, R.sub.1 and R.sub.3 each represent an atom of hydrogen or an alkyl radical, R.sub.4 and R.sub.5, which are the same or different, each respresent a hydrogen atom, a straight- or branched-chain alkyl, alkenyl or alkynyl radical containing from 1 to 5 carbon atoms or an .omega.-hydroxyalkyl radical containing from 2 to 5 carbon atoms or R.sub.4 and R.sub.
    Type: Grant
    Filed: March 20, 1978
    Date of Patent: May 6, 1980
    Assignee: Labaz
    Inventors: Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Jean-Pierre Werbenec, Madeleine C. Epse Broll
  • Patent number: 4201874
    Abstract: Synthesis and intermediates for making insect pheromone useful in the control of red scale, Aonidiella aurantii.
    Type: Grant
    Filed: November 24, 1978
    Date of Patent: May 6, 1980
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4200586
    Abstract: The carbon-carbon double bond isomerization of a substituted or an unsubstituted hydrocarbon compound having olefinic unsaturation in a less stable form to an isomer of said compound having olefinic unsaturation in a more stable form is inhibited by contacting with said compound having the more unstable form with an alkali metal salt of a di-, tri- or tetracarboxylic acid.
    Type: Grant
    Filed: January 10, 1978
    Date of Patent: April 29, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4196300
    Abstract: Glycidates and thioglycidates substituted in the .alpha.-position with a long chain alkyl of from 11 to 16 carbons having hypoglycemic activity.
    Type: Grant
    Filed: August 18, 1978
    Date of Patent: April 1, 1980
    Assignee: McNeilabs, Inc.
    Inventors: Richard J. Mohrbacher, Winston Ho, Gene Tutwiler
  • Patent number: 4185027
    Abstract: A process for hydrolyzing methyl esters having carboxylic acid moieties containing 6 to 22 carbon atoms involves reacting said esters with water in the presence of carboxylic acid and strong acid catalysts to produce acid corresponding to reactant ester and methanol and driving the reaction toward completion by removing the methanol.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: January 22, 1980
    Assignee: The Procter & Gamble Company
    Inventor: Ted J. Logan
  • Patent number: 4180681
    Abstract: A process for the recovery of methacrylic acid formed from an aqueous sodium methacrylate solution derived from the silver catalyzed oxidation reaction of methacrolein and an aqueous solution of sodium hydroxide which comprises contacting the aqueous sodium methacrylate solution at a suitable temperature, in the presence of a high gaseous carbon dioxide pressure, with a water immiscible alkane, cycloalkane, alkyl benzene, or carboxylic acid ester solvent to extract and form a methacrylic acid-containing organic solvent phase, an aqueous phase and a precipitated sodium bicarbonate solid phase and recovering the methacrylic acid from the organic solvent phase. Liquid CO.sub.2 which may be employed with the water immiscible solvent at 800 psig may also be employed alone at its equilibrium vapor pressure as the reactant and extractant medium.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: December 25, 1979
    Assignee: Atlantic Richfield Company
    Inventors: John J. Leonard, Harold Shalit
  • Patent number: 4177216
    Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: September 26, 1978
    Date of Patent: December 4, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4161536
    Abstract: Aliphatic carboxylic acid esters of the formula ##STR1## wherein R.sub.1 represents hydrogen or methyl,X.sub.1 represents halogen,Y represents halogen or methyl, andZ represents cyano or ethynyl, processes for producing them and their use in combating pests.
    Type: Grant
    Filed: November 7, 1977
    Date of Patent: July 17, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Saleem Farooq, Laurenz Gsell, Odd Kristiansen, Willy Meyer
  • Patent number: 4144399
    Abstract: A process for the preparation of acrylic acid or methacrylic acid by the ruthenium and/or osmium catalyzed conversion of peroxide (peroxy) intermediate compounds, derived from the autoxidation of acrolein or methacrolein, to the corresponding .alpha.,.beta.-unsaturated carboxylic acid, particularly the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.
    Type: Grant
    Filed: March 23, 1977
    Date of Patent: March 13, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Ming N. Sheng, Jar-lin Kao
  • Patent number: 4143066
    Abstract: A lower carboxylic acid such as acetic acid is separated and recovered from an aqueous medium by the steps which include contacting, in an extraction zone, the aqueous medium with an extracting agent such as trioctyl phosphine oxide dissolved in an organic solvent such as a mixture of paraffins having a boiling range of about 160.degree. C. to 175.degree. C.
    Type: Grant
    Filed: December 16, 1976
    Date of Patent: March 6, 1979
    Assignee: The Dow Chemical Company
    Inventor: Victor Kalcevic
  • Patent number: 4129510
    Abstract: Sulfur-containing compounds of the formula ##STR1## WHEREIN R is a hydrocarbyl radical; each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently hydrogen or a hydrocarbyl radical; m' is from one to about five; and each A is an alkyl radical containing at least one carboxyl group or functional derivative thereof, are useful as additives in lubricants and fuels.
    Type: Grant
    Filed: April 28, 1976
    Date of Patent: December 12, 1978
    Assignee: The Lubrizol Corporation
    Inventor: Donald M. Smith
  • Patent number: 4124635
    Abstract: A process for the liquid phase oxidation of .alpha.,.beta.-unsaturated aliphatic aldehydes, such as methacrolein and the in situ decomposition or conversion of unsaturated peroxy (peroxide) compounds formed during the oxidation to the corresponding .alpha.,.beta.-unsaturated aliphatic carboxylic acids which comprises passing oxygen or an oxygen-containing gas such as air through an inert solvent solution of the unsaturated aldehyde at a suitable temperature and pressure in the presence of an organic or inorganic zinc salt catalyst.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: November 7, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Jar-lin Kao, John J. Leonard
  • Patent number: 4124633
    Abstract: A process for the preparation of acrylic acid or methacrylic acid which comprises catalytically decomposing or converting in the presence of tellurium the peroxide (peroxy) compounds contained in the oxidate solution derived from the autoxidation of acrolein or methacrolein, particularly, the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.
    Type: Grant
    Filed: August 1, 1977
    Date of Patent: November 7, 1978
    Assignee: Atlantic Richfield Company
    Inventors: John J. Leonard, Jar-lin Kao
  • Patent number: 4115440
    Abstract: A process for the preparation of acrylic acid or methacrylic acid which comprises catalytically decomposing or converting in the presence of selenium the peroxide (peroxy) compounds formed during autoxidation or contained in the oxidate solution derived from the autoxidation of the respective acrolein or methacrolein, particularly, the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.
    Type: Grant
    Filed: April 19, 1977
    Date of Patent: September 19, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Ming Nan Sheng, Jar-lin Kao
  • Patent number: 4113574
    Abstract: The prior art discloses a number of polymerization inhibitors for acrylic acid, acrylates and derivatives thereof, but such polymerization inhibitors have low vapor pressures. Consequently, when acrylic acid is vaporized, it tends to polymerize on cooling surfaces causing undesirable deposits on storage vessels and the like. However, when a polymerization inhibiting amount of 2,4-pentanedione is added to the monomer, the polymerization of acrylic acid on cooling surfaces is inhibited.
    Type: Grant
    Filed: October 22, 1976
    Date of Patent: September 12, 1978
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, James E. White