Acyclic Patents (Class 568/671)
  • Patent number: 5112519
    Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula (C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: May 12, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas J. Giacobbe, George A. Ksenic
  • Patent number: 5113003
    Abstract: The silicon-containing phenoxy ethers are of the formula III: ##STR1## wherein R.sup.1 and R.sup.2 which may be the same or different are selected from H, --R.sup.3 --X, aliphatic hydrocarbyl having 1-6 carbon atoms or aryl, or substituted derivatives thereof, provided that not more than one of R.sup.1 and R.sup.2 is H;R.sup.3 is a divalent C.sub.1 -C.sub.30 aliphatic and/or aromatic hydrocarbyl group which may optionally be substituted, or interrupted, by a hetero atom;R.sup.4 and R.sup.5 which may be the same or different are H, ##STR2## or an ortho para directing activating group for aromatic electrophilic substitution, other than an amine;and X is a reactive functional group capable of undergoing an acid-catalyzed electrophilic aromatic substitution reaction with a phenol, for example an aldehyde group. They can be polymerized to produce silicone-modified polymers of the phenol-aldehyde type without the use of free aldehyde.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: May 12, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, Pauline Coakley
  • Patent number: 5091536
    Abstract: Organic-solvent soluble magnesium hydrides of the formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamide, aralkyl, aryl or diarylamide group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamide, diarylamide or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: February 25, 1992
    Assignee: Studiengesellschaft Kohle mbh
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5087775
    Abstract: A process for the preparation of partially fluorinated alcohols starting from halogen-containing alkenes, and 2,2,3,3,4,4-hexafluorocyclopentanol as a new partially fluorinated alcohol.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: February 11, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Dietmar Bielefeldt, Michael Negele, Heinz Ziemann
  • Patent number: 4982011
    Abstract: Ether/ether-alcohol rich compositions are produced by hydrogenating hydroformylation reaction products, separating an ether/ether-alcohol containing mixture from the hydrogenation product, and catalytically hydrogenating such mixture at 200.degree.-250.degree. C. and 30-100 atmospheres. The crude product is then reflux distilled to separate the ether/ether-alcohol rich compositions from lighter and heavier ends.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: January 1, 1991
    Assignee: Exxon Research and Engineering Co.
    Inventor: Jean A. A. Hanin
  • Patent number: 4792639
    Abstract: An improved process for the production of methyl ethers of the type in which methanol is reacted with a branched monoolefin in the presence of a catalytically effective amount of one or more acid catalyst, said improvements comprising carrying out said reaction in one or two steps in the presence of one or more liquid organic compounds having one or more hydroxy substituents which functions as a carrier for the branched monoolefins. The hydroxy compound also inhibits the polymerization of the branched monoolefins.
    Type: Grant
    Filed: August 27, 1987
    Date of Patent: December 20, 1988
    Assignee: Allied-Signal, Inc.
    Inventors: Divakaran Masilamani, George S. Hammond, Andiappan K. S. Murthy
  • Patent number: 4714788
    Abstract: In a process for separating C.sup.4 to C.sup.7 tertiary mono-olefins(s) present in a C.sup.4 to C.sup.7 hydrocarbon mixture containing diolefins which comprises selectively reacting said tertiary mono-olefin mixture with a primary alcohol in the presence of an acid catalyst to convert it to tertiary ether(s), separating the tertiary ether(s) from the unreacted hydrocarbon mixture and containing said tertiary ether(s) in the presence of a catalyst to decompose it to tertiary olefin(s) and a primary alcohol, the improvement which comprises hydrogenating the tertiary ether(s) after it has been separated from the unreacted hydrocarbon mixture and prior to decomposition to saturate the unsaturated ether(s) formed from the diolefins present in the hydrocarbon mixture.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: December 22, 1987
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert C. Michaelson, Jeffrey S. Plotkin
  • Patent number: 4709101
    Abstract: An improved process for the production of methyl ethers of the type in which methanol is reacted with a branched monoolefin in the presence of a catalytically effective amount of one or more acid catalyst, said improvements comprising carrying out said reaction in one or two steps in the presence of one or more liquid organic compounds having one or more hydroxy substituents which functions as a carrier for the branched monoolefins. The hydroxy compound also inhibits the polymerization of the branched monoolefins.
    Type: Grant
    Filed: September 30, 1985
    Date of Patent: November 24, 1987
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, George S. Hammond, Andiappan K. S. Murthy
  • Patent number: 4707302
    Abstract: 2-Substituted 4,4,7,7-tetramethyl-1,3-dioxacycloheptanes of the general formula I ##STR1## where R.sup.1 is a straight-chain or branched alkyl of 1 to 10 carbon atoms which additionally may contain oxygen in the form of an ether group or is 5- to 8-membered cycloalkyl of up to 10 carbon atoms which may additionally contain oxygen in the form of an ether group, of which particularly interesting representatives are 2,4,4,7,7-pentamethyl-1,3-dioxacycloheptane, 2-tert.-butyl-4,4,7,7-tetramethyl-1,3-dioxacycloheptane and 2-isopropyl-4,4,7,7-tetramethyl-1,3-dioxacycloheptane, are prepared and used as scents.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: November 17, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Hardo Siegel
  • Patent number: 4683343
    Abstract: Heavy organic by-products obtained by hydroformylating olefins and hydrogenating the crude product to obtain higher alcohols, and their steam cracked derivatives, have been found useful as viscosity modifiers and low temperature property improvers in flexible PVC compositions.
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: July 28, 1987
    Assignee: Exxon Research & Engineering Co.
    Inventors: Jean A. Hanin, Pierre E. Verrier
  • Patent number: 4617287
    Abstract: Ruthenium carbonyl-cobalt carbonyl catalyst mixtures effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals, wherein said acetal may be prepared separately or in situ from an aldehyde and an alcohol. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of this ruthenium carbonyl-cobalt carbonyl catalyst to form the monomethyl ether of ethylene glycol.The invention also is directed to the ruthenium carbonyl-promoted cobalt carbonyl catalysts per se, including novel precipitated forms of these ruthenium-cobalt carbonyl catalyst mixtures.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: October 14, 1986
    Assignee: Sun Refining and Marketing Company
    Inventor: James E. Lyons
  • Patent number: 4605796
    Abstract: A process for producing ethanol which comprises reacting methanol, carbon monoxide and hydrogen in the presence of (a) a catalyst comprising cobalt or a cobalt compound and a tertiary phosphine as an effective component and (b) promoter comprising an aromatic carboxylic acid, an ester thereof, or a cobalt salt of aromatic carboxylic acid is disclosed. According to the present invention, formation of by-products becomes less and selectivity to realizable ethanol becomes higher.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: August 12, 1986
    Assignee: Agency of Industrial Science and Technology
    Inventors: Nobuo Isogai, Takashi Okawa, Motoyuki Hosokawa, Toshiyasu Watanabe, Natsuko Wakui
  • Patent number: 4593142
    Abstract: Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: June 3, 1986
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4579980
    Abstract: An ether compound is advantageously produced by an ether exchange reaction of a different ether compound and a hydroxy group containing compound in the presence of a heteropoly acid or an acidic salt thereof as the catalyst. The catalyst is novel and is extremely effective to the present process and brings about less by-products compared to other processes or other catalysts.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: April 1, 1986
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Kiyoshi Kogoma, Norio Sone, Takashi Tobita, Masahiro Shiozaki
  • Patent number: 4523040
    Abstract: This invention relates to solid acidic or metal catalyst-promoted halogenation of methane to produce methyl monohalides in high selectivity. Concurrent or simultaneous hydrolysis provides methyl alcohol and/or dimethyl ether in good yields.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: June 11, 1985
    Inventor: George A. Olah
  • Patent number: 4514336
    Abstract: A process for homologating alcohols and/or acids to a mixture of higher acids by reaction with syngas in the presence of a ruthenium-rhodium-iodide-titanium(IV) catalyst.
    Type: Grant
    Filed: May 28, 1982
    Date of Patent: April 30, 1985
    Assignee: Shell Oil Company
    Inventors: Robert C. Ryan, Lynn H. Slaugh
  • Patent number: 4503275
    Abstract: Butane-1,4-diol is produced by converting allyl alcohol to an allyl t-alkyl or -cycloalkyl ether of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: March 5, 1985
    Assignee: Davy McKee (London) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4484009
    Abstract: A process for the manufacture of the monoether of monoethylene glycol by the hydrogenolysis of a 2-alkyl-1,3-dioxolane, with a co-catalytic system of palladium and an acid of phosphorus or a phosphoric ester of ethylene glycol and in the presence of ethylene glycol.
    Type: Grant
    Filed: April 4, 1983
    Date of Patent: November 20, 1984
    Assignee: Atochem
    Inventors: Elie Ghenassia, Andre Lakodey
  • Patent number: 4479017
    Abstract: In a process for producing an ether compound by the catalytic hydrogenolysis of an acetal compound in the presence of a catalyst, the improvement wherein an acetal compound of the following formula (2) ##STR1## wherein R represents a hydrogen atom or a lower alkoxy group, Y represents an alkylene group having 2 to 12 carbon atoms, n represents a positive number of from 1 to 6, the two groups R(YO).sub.n may, together with the carbon atom to which they are bonded, represent a 1,3-dioxolane ring, and R.sup.1 and R.sup.2, independently from each other, represent a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, provided that at least one of R.sup.1 and R.sup.2 represents a hydrogen atom,is catalytically hydrogenolyzed in the presence of a palladium catalyst on a carbon carrier in the absence of an acid substance added, thereby to form an ether compound of the following formula (1)R(YO).sub.n CHR.sup.1 R.sup.2 (1)whereinR, R.sup.1, R.sup.2, Y and n are as defined.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: October 23, 1984
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Tadashi Ayusawa, Tadamichi Aoki, Yutaka Nomura
  • Patent number: 4404408
    Abstract: Metal or metalloid salts, ansolvo-acids and proton-acids can be so complexed with 1,2,3-triols, glycerol ethers or glycerol thioethers containing at least 6 C atoms in the molecule that they are in the form of compositions which are soluble in organic solvents, especially non-polar, aprotic solvents, such as hydrocarbons. These stable compositions display an outstanding anti-static action and, because of their spectrum of properties, are especially suitable for imparting anti-static characteristics to polymers, lubricants, fuels and also solvents based on hydrocarbons.
    Type: Grant
    Filed: September 7, 1977
    Date of Patent: September 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4393249
    Abstract: A process for removing alkynes from hydrocarbon mixtures, particularly those containing butadiene by reacting the alkynes with hydroxyl group containing organic compounds in the presence of a silver exchanged ion-exchange resin and separating the products formed from the unreacted components of said mixture.
    Type: Grant
    Filed: October 23, 1981
    Date of Patent: July 12, 1983
    Assignee: The Dow Chemical Company
    Inventors: Albert Heuvelsland, Fritz F. F. Jann, Greet de Block-Martens
  • Patent number: 4390734
    Abstract: Propylene glycol monoalkyl ethers are prepared in good yield by reacting acetaldehyde and an alkanol (or by reacting an acetal) with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt-containing compound and a cocatalyst comprising a member of the group consisting of rhodium-containing compounds, ruthenium-containing compounds and nickel-containing compounds, and heating the resulting mixture at moderate temperatures and pressures for sufficient time to produce the desired glycol monoalkyl ether, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: June 28, 1983
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4384148
    Abstract: Alcohols may be obtained by the indirect hydration of olefinic hydrocarbons in which the olefinic hydrocarbon is esterified by treatment with an organic acid such as acetic acid. The organic esters may then be hydrolyzed by treatment with water to form hydrolysis products comprising alcohols and ethers which may be separated from the reconstituted organic acid. The alcohol products are then separated from the ether product, the latter which may then be further treated by thermal cracking, decomposition, or hydrolysis to form an additional amount of the desired alcohol.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: May 17, 1983
    Assignee: UOP Inc.
    Inventor: Robert J. Schmidt
  • Patent number: 4383125
    Abstract: Aldehyde ethers of the general formula ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, and wherein Y represents --CH.sub.2 --CH.sub.2 --C.sub.2 or --CH.sub.2 --CH (CH.sub.3)--, are prepared by hydroformylation of a corresponding compound of formula: ##STR2## by reaction with hydrogen and carbon monoxide in the presence of a hydroformylation catalyst, e.g. a rhodium complex catalyst. Preferred compounds include 4-t-butoxybutyraldehyde and 3-t-butoxy-2-methylpropionaldehyde.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: May 10, 1983
    Assignee: Davy McKee (Oil & Chemicals) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4374286
    Abstract: Alcohols may be obtained by an indirect hydration of olefinic hydrocarbons in which the olefinic hydrocarbon is first esterified by treatment with an inorganic acid to form dialkyl and alkyl hydrogen salts. These salts are then trans-esterified by treatment with an organic acid to form an organic ester. The reconstituted inorganic acid is separated from this mixture by stripping and recycled, while the organic esters are then treated with water in a hydrolysis step to reconstitute the organic acid and form the desired alcohol and ether. The alcohol product is separated from the ether which may then be further treated by thermal decomposition or hydrolysis to form an additional amount of the desired alcohol.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: February 15, 1983
    Assignee: UOP Inc.
    Inventor: Robert J. Schmidt
  • Patent number: 4356126
    Abstract: Process for the carbonylation of alkanols and/or ethers at elevated temperature and pressure in the presence of a Group VIII metal compound and pentachlorobenzenethiol and/or salts thereof, using a pentachlorobenzenethiol compound: Group VIII metal compound molar ratio of not more than 10. The process is of special interest for the production of methyl acetate from methanol using an active, iodine-free catalytic system.
    Type: Grant
    Filed: June 17, 1981
    Date of Patent: October 26, 1982
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4319043
    Abstract: The invention relates to the production of oxygenated organic compounds comprising alcohols, aldehydes, ethers and salts of carboxylic acids. Prior art processes for the production of ethanol in particular involve the use of elevated temperatures and pressures. Milder conditions can be used in the process of the invention in which either a mercury compound of formula (R.sup.1 OCHR.sup.2 CHR.sup.3 Hg).sub.n X (I), wherein X is an organic or inorganic anion, n is an integer equal to the valency of the anion, R.sup.2 and R.sup.3 are independently a hydrogen atom or an alkyl group and R.sup.1 is a hydrogen atom, an alkyl group or the group --(--CHR.sup.2 CHR.sup.3 Hg).sub.n X, or the precursors of the compound (I), with a catalyst comprising a complex containing a metal of Group VIII, particularly rhodium, in the presence of a liquid reagent containing an active acidic hydrogen atom. A particularly suitable rhodium complex is one having the formula:[Rh(C.sub.5 Me.sub.5).sub.2 (OH).sub.3 ]Cl.xH.sub.
    Type: Grant
    Filed: March 26, 1980
    Date of Patent: March 9, 1982
    Assignees: University of Sheffield, BP Chemicals Limited
    Inventors: John Cook, Peter M. Maitlis
  • Patent number: 4319050
    Abstract: A homogeneous catalytic process for the decarbonylating of formate esters to alcohols and carbon monoxide. The process comprises contacting formate esters of the formula HCOOR where R is C.sub.1 -C.sub.10 aliphatic, C.sub.7 -C.sub.14 araliphatic or C.sub.6 -C.sub.10 aryl with a copper complex of the formula Cu(L)X where L is CO, phosphine or phosphite and X is the anion of an acid in an inert atmosphere at temperatures of from about 100.degree. to 300.degree. C.
    Type: Grant
    Filed: February 13, 1981
    Date of Patent: March 9, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventor: Gerald Doyle
  • Patent number: 4261839
    Abstract: A fiber preparation containing or consisting of a tertiary butyl ether of the general formula ##STR1## in which R.sub.1 is a straight-chain or branched C.sub.12 -C.sub.22 -alkyl or alkenyl group.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: April 14, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rolf Kleber, Siegfried Billenstein
  • Patent number: 4262157
    Abstract: Decarboxylation of carboxylic acids using diazabicycloalkenes and, if desired, also a simple copper salt, as the means for decarboxylation.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: April 14, 1981
    Assignee: Abbott Laboratories
    Inventors: Yuji Hori, Yoshiaki Nagano, Hiroshi Taniguchi
  • Patent number: 4239924
    Abstract: A process for selectively producing ethanol which comprises introducing into a reaction zone (1) methanol, (2) hydrogen, (3) carbon monoxide, (4) a cobalt tricarbonyl complex, (5) an iodine compound and (6) a ruthenium compound and then subjecting the contents of said reaction zone to an elevated temperature and an elevated pressure for a time sufficient to convert methanol to ethanol.
    Type: Grant
    Filed: May 25, 1979
    Date of Patent: December 16, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Wayne R. Pretzer, Thaddeus P. Kobylinski, John E. Bozik
  • Patent number: 4239925
    Abstract: A process for selectively producing ethanol which comprises introducing into a reaction zone methanol, hydrogen, carbon monoxide, a cobalt tricarbonyl complex and an iodine promoter and then subjecting the contents of said reaction zone to an elevated temperature and an elevated pressure for a time period sufficient to convert methanol to ethanol.
    Type: Grant
    Filed: May 25, 1979
    Date of Patent: December 16, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Wayne R. Pretzer, Thaddeus P. Kobylinski, John E. Bozik
  • Patent number: 4189441
    Abstract: A process is disclosed for preparing esters having the general formulae:RCOOCH.sub.2 R'andR'COOCH.sub.2 Rwherein R and R' are linear or branched alkyl radicals either like or unlike each other, and containing from 1 to 16 carbon atoms, or considered together, forming a cycloaliphatic ring having up to 7 carbon atoms, wherein carbon monoxide and hydrogen are reacted, at temperatures ranging from 150.degree. to 350.degree. C. and at pressures ranging from 50 to 1000 atmospheres, with an ether of formula R O R' or esters of formula RCOOR' and R'COOR, in which R and R' have the same meanings as specified hereinabove, and in the presence of a catalyst system comprising a ruthenium carbonyl and a promoter selected from the class consisting of hydroiodic acid, carboxylic acid solutions of inorganic or tetraalkylammonium bromides and iodides, and mixtures of these promoters.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: February 19, 1980
    Assignee: Montedison S.p.A.
    Inventors: Giuseppe Braca, Glauco Sbrana, Guglielmo Gregorio
  • Patent number: 4181809
    Abstract: This invention provides a process for producing tertiary-butyl methyl ether which involves contacting a mixture of isobutylene and synthesis gas with a catalyst under modified methanol synthesis processing conditions.
    Type: Grant
    Filed: October 31, 1978
    Date of Patent: January 1, 1980
    Assignee: El Paso Products Company
    Inventor: Norbert F. Cywinski
  • Patent number: 4152351
    Abstract: Aliphatic unsaturated material or compounds are hydrogenated. Specifically, unsaturated dinitrile, e.g., 5-methyl-4-nonenedinitrile, 2,4-dimethyl-4-octenedinitrile, 2,4-dimethyl-3-octenedinitrile, 2,4,6-trimethyl-3-heptenedinitrile, 5-methylenenonanedinitrile, 2-methyl-4-methyleneoctanedinitrile and 2,6-dimethyl-4-methyleneheptanedinitrile, in a mixture resulting from reaction of isobutylene and acrylonitrile are hydrogenated in presence of a palladium hydrogenation catalyst disposed on an active alumina support also having disposed thereon an adjuvant selected from cerium, thorium, manganese, praseodymium, neodymium and samarium. A specific combination of adjuvants namely cerium together with lanthanum was found to improve the hydrogenation at low levels of cerium.Other aliphatic compounds which can be hydrogenated according to the invention include among others ethylene, 1,3-butadiene, cinnamic acid, 5-methyl-4-nonenedicarboxylic acid, diethyl 5-methylene-nonanedicarboxylate, etc.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: May 1, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4146581
    Abstract: A process for the manufacture of higher ketones by reacting an aldehyde with a ketone in the presence of hydrogen over a catalyst system which contains, firstly, oxides or salts of the rare earth metals and, secondly, metals of group VIII of the periodic table of the elements. The process gives numerous higher ketones, required, for example, as solvents for surface coatings, or as scents, with high conversions and good selectivities, and therefore more simply and more economically than conventional methods.
    Type: Grant
    Filed: March 30, 1977
    Date of Patent: March 27, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Nissen, Otto Woerz, Gerd Heilen, Werner Fliege, Arnold Wittwer
  • Patent number: 4134912
    Abstract: A carboxylic acid, such as acetic acid, is prepared from a hydrocarbyl alcohol, such as methanol, in carbonylation processes comprising the use of an iodide, carbon monoxide and a nickel catalyst in the presence of a tin promoter.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: January 16, 1979
    Assignee: Halcon International, Inc.
    Inventors: Anthony N. Naglieri, Nabil Rizkalla
  • Patent number: 4133966
    Abstract: A process for the selective formation of ethanol which comprises contacting methanol, hydrogen and carbon monoxide with a catalyst system comprising cobalt acetylacetonate, a tertiary organo Group V A compound of the periodic Table, a first promoter comprising an iodine compound and a second promoter comprising a ruthenium compound.
    Type: Grant
    Filed: December 23, 1977
    Date of Patent: January 9, 1979
    Assignee: Gulf Research & Development Company
    Inventors: Wayne R. Pretzer, Thaddeus P. Kobylinski, John E. Bozik
  • Patent number: 4124647
    Abstract: A process for the preparation of ethers is described wherein at least one alcohol is contacted in the presence of carbon monoxide with a catalyst system having the general formula:B.sub.x Me[Me'(CO).sub.a (L).sub.b ].sub.2and a cocatalyst comprising halogen containing compounds in a cocatalyst to catalyst molar ratio ranging from about 16 to about 100 wherein B is a Lewis base capable of coordinating with a Group IIA metal; Me is a Group IIA metal, preferably magnesium; Me' is a transition metal selected from the group consisting of metals of Groups VIB, VIIB and VIII of the Periodic Table of the Elements; L is a uni- or polydentate ligand or hydrocarbon capable of coordinating with the transition metal; x is a positive integer ranging from 1 to 4; a is a positive integer ranging from 1 to 5 and b is an integer ranging from 0 to 4, with the proviso that the sum of a and b is 5 or less. A typical preferred catalyst system is represented by the general formula:(C.sub.4 H.sub.8 O).sub.4 Mg[Mn(CO).sub.4 P(C.sub.
    Type: Grant
    Filed: May 23, 1977
    Date of Patent: November 7, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventor: Gary B. McVicker