Diolefin Product Patents (Class 585/601)
  • Patent number: 4992609
    Abstract: Novel phosphonium salts of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each is a hydrogen atom or a hydrocarbon group of 1 to 12 carbon atoms which may optionally be substituted; R.sup.3 is a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms which may optionally be substituted; R.sup.4, R.sup.5 and R.sup.6 each is a hydrocarbon group of 1 to 8 carbon atoms which may optionally be substituted; X is a hydroxyl group, a hydroxycarbonyloxy group or a lower alkylcarbonyloxy group, and processes for production of the salts are described. Telomerization catalysts containing said phosphonium salts and processes for production of straight-chain alkadienyl compounds using the same catalysts are also provided.
    Type: Grant
    Filed: March 13, 1990
    Date of Patent: February 12, 1991
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiko Maeda, Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4943670
    Abstract: A process for the preparation of a compound of general formula ##STR1## in which R.sup.1 represents a hydrogen atom or a methyl group, one of R.sup.2 and R.sup.3 represents a hydrogen atom and the other of R.sup.2 and R.sup.3 is the same as R.sup.1, which comprises reacting a compound of the general formulaR.sup.1 CH.dbd.C.dbd.CH.sub.2 (II)with a salt of formic acid in the presence of a catalyst system comprising a palladium salt and a phosphorus compound of general formulaP(OX).sub.n (X).sub.3-n (III)in which n is 0,1,2 or 3 and each X independently represents an alkyl, alkenyl, aryl, aralkyl, alkaryl or cycloalkyl group, and recovering the desired compound of formula (I).
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: July 24, 1990
    Assignee: Shell Oil Company
    Inventors: Brian L. Goodall, Willem Terlouw, Jacob C. van der Sar
  • Patent number: 4843178
    Abstract: The present invention relates to a process for producing an E,Z-9-alkenyl-1-aldehyde component which comprises:(a) disproportionating cyclooctene and an .alpha.-olefin in the presence of a suitable disproportionation catalyst under disproportionation conditions suitable to form a 1,9-alkadiene;(b) reacting the 1,9-alkadiene obtained in step (a) with a suitable metallating agent under conditions suitable to form a 1-metallo-9-alkene;(c) contacting the 1-metallo-9-alkene obtained in step (b) with oxygen under conditions suitable to form a 1-oxymetallo-9-alkene;(d) hydrolyzing the 1-oxymetallo-9-alkene suit a suitable hydrolyzing agent, under suitable hydrolyzing conditions to form E,Z-9-alkenyl-1-alcohol.(e) oxidizing said E,Z-9-alkenyl-1-alcohol with a suitable oxidizing agent under oxidizing conditions suitable to form E,Z-9-alkenyl-1-aldehyde.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: June 27, 1989
    Inventors: Jim D. Byers, Charles A. Drake
  • Patent number: 4762962
    Abstract: This invention relates to a process for the isomerization of branched dienes which comprises contacting at isomerization conditions a branched diene with a boron phosphate catalyst wherein the initial ratio of phosphorus (P) to boron (B) is less than 1.0 but greater than 0.6. The contacting is conducted at a temperature of from 100.degree. C. to 450.degree. C. and at a pressure from subatmospheric to superatmospheric.
    Type: Grant
    Filed: June 8, 1987
    Date of Patent: August 9, 1988
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Lawson G. Wideman
  • Patent number: 4636573
    Abstract: Compounds of the formulae I and II ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 12 carbon atoms,R.sup.6 and R.sup.7 are independently alkyl having 1 to 30 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 12 carbon atoms;A is a direct bond, a methylene or an ethylene radical,B is an alkanediyl radical of 2 to 10 carbon atoms, the radical of formula --CH.sub.2 CH.sub.2 --S--CH.sub.2 CH.sub.2 -- or of the formula III--CH.sub.2 CH.sub.2 --(O--CH.sub.2 CH.sub.2).sub.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: January 13, 1987
    Inventors: Stephen D. Pastor, John D. Spivack
  • Patent number: 4604480
    Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.
    Type: Grant
    Filed: August 15, 1983
    Date of Patent: August 5, 1986
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Mohammad Aslam
  • Patent number: 4571443
    Abstract: Certain benzylic and allylic compounds are catalytically oxidatively dehydrodimerized wherein the molecular oxygen oxidant is separated from the substrate by a gas impervious catalyst membrane that conducts oxide ions from the surface of the catalyst membrane wall to the opposite surface thereof which is in contact with the substrate.
    Type: Grant
    Filed: July 23, 1985
    Date of Patent: February 18, 1986
    Assignee: The Standard Oil Company
    Inventors: Robert DiCosimo, James D. Burrington, Robert K. Grasselli
  • Patent number: 4554375
    Abstract: A method for preparing 2,7-octadienyl formate by reacting 1,3-butadiene with formic acid in the presence of a platinum(II) catalyst is described. The platinum(II) catalyst is preferably platinum acetylacetonate. A reaction temperature between 50.degree. and 150.degree. C. is preferred, and carbon dioxide and a solvent may also be employed. Tetrahydrofuran and acetone are the preferred aprotic solvents.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: November 19, 1985
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, David C. Alexander
  • Patent number: 4536604
    Abstract: A method for preparing 1,6-octadiene by reacting 1,3-butadiene with formic acid in the presence of a platinum(II) catalyst and a polymeric tertiary amine catalyst is described. The combination of a platinum(II) catalyst such as platinum acetylacetonate with a polymeric tertiary amine promoter such as AMBERLYST.RTM. A21 macroreticular ion-exchange resin gives a high selectivity to 1,6-octadiene as opposed to the 1,7-octadiene form. A reaction temperature between 50.degree. and 150.degree. C. is preferred, and carbon dioxide and a solvent may also be employed.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: August 20, 1985
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, David C. Alexander
  • Patent number: 4434310
    Abstract: A process for the isomerization of isolated double bonds to conjugated double bonds in optionally substituted cyclooctadienes using alkali metal or alkaline earth metal amides, if desired in the presence of a solvent, requires that the alkali metal or alkaline earth metal amide be produced with exclusion of moisture and under a protective gas atmosphere in the presence of the cyclooctadiene to be isomerized; and that the isomerization be conducted at temperatures of 70.degree.-200.degree. C.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: February 28, 1984
    Assignee: Chemische Werke Huels Aktiengesellschaft
    Inventor: Wolfgang Kampf
  • Patent number: 4368141
    Abstract: A novel disproportionation catalyst comprising the product resulting from the combination of elemental sulfur and a disproportionation catalyst consisting essentially of a refractory oxide containing molybdenum oxide or tungsten oxide.
    Type: Grant
    Filed: June 24, 1981
    Date of Patent: January 11, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Semyon Kukes
  • Patent number: 4359568
    Abstract: A process for synthesizing novel polyaromatic amides containing 1,3-butadiene groups along the polymer chain by effecting a reaction between the acid chloride of 1,4-bis-p-carboxyphenyl-1,3-butadiene and an aromatic diamine. These polyamides have been found to be especially useful as laminating resins for a variety of laminating applications.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: November 16, 1982
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Carl S. Marvel, Venkatesa Sankaran
  • Patent number: 4317905
    Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
  • Patent number: 4247723
    Abstract: Dihydromyrcenol (3,7-dimethylocta-1-en-7-ol) and carboxylic acid esters thereof are prepared from dimethylcyclooctene reactant mixtures comprising 1,5-dimethylcyclooctene in admixture with 1,6-dimethylcyclooctene and/or 1,4-dimethylcyclooctene by (a) thermally isomerizing the dimethylcyclooctene reactant mixture to afford a mixed octadiene product comprising 2,6-dimethylocta-1,7-diene in admixture with 2,7-and/or 2,5-dimethylocta-1,7-diene, (b) reacting the mixed octadiene product with a carboxylic acid to selectively form the ester of 3,7-dimethyl-octa-1-en-7-ol and (c) optionally hydrolyzing the ester of 3,7-dimethyl-octa-1-en-7-ol under basic conditions to yield dihydromyrcenol.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: January 27, 1981
    Assignee: Shell Oil Company
    Inventor: Aaldert J. de Jong
  • Patent number: 4243829
    Abstract: A process for preparing 1,7-octadiene by dimerizing butadiene in the presence of a catalytic amount of palladium acetate and a tertiary phosphine, a solvent in an amount sufficient to dissolve the catalyst, a strong base and formic acid, wherein: (a) the molar ratio of the strong base to the formic acid is 1:1-2, (b) the mole ratio of tertiary phosphine to palladium is at least 1, (c) the amount of strong base present is such that the pH of the reaction medium is from 7.5 to 10.5 and (d) the solvent is at least one member selected from the group consisting of aromatic hydrocarbons, lower alkyl substituted aromatic hydrocarbons, halogenated aromatic hydrocarbons, halogenated lower aliphatic hydrocarbons, nitriles, amides, dilower alkyl ethers, lower alkyl phenyl ethers, lower alkyl esters of lower alkanoic acids, ketones and lower alkanols.
    Type: Grant
    Filed: October 4, 1976
    Date of Patent: January 6, 1981
    Assignee: Charles U. Pittman, Jr.
    Inventors: Charles U. Pittman, Jr., Ronald Hanes
  • Patent number: 4180524
    Abstract: Double bond isomerization and disproportionation of olefins is obtained by contact with a catalyst in a single-stage composition containing a support, uranium, and at least one of tungsten, molybdenum, or rhenium.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: December 25, 1979
    Assignee: Phillips Petroleum Company
    Inventors: Robert E. Reusser, William B. Hughes