GB889730A - Polymerization of acetylene and mono-substituted acetylenes and catalysts therefor - Google Patents

Polymerization of acetylene and mono-substituted acetylenes and catalysts therefor

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Publication number
GB889730A
GB889730A GB4078560A GB4078560A GB889730A GB 889730 A GB889730 A GB 889730A GB 4078560 A GB4078560 A GB 4078560A GB 4078560 A GB4078560 A GB 4078560A GB 889730 A GB889730 A GB 889730A
Authority
GB
United Kingdom
Prior art keywords
chloride
nickel
phosphine
cobalt
palladium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4078560A
Inventor
Lionel Benedict Luttinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to GB4078560A priority Critical patent/GB889730A/en
Publication of GB889730A publication Critical patent/GB889730A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/38Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00Polymerisation catalysts
    • C08F4/06Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24Phosphines

Abstract

Catalysts for the polymerization of acetylene and monosubstituted acetylenes comprise mixtures of (1) a complex of formula [M(R3Y)p]mXn where m and n are 1 to 4 or when M is osmium 1 to 6; p is 1 to 6 or when M is osmium 1 to 8; M is nickel, cobalt, palladium, platinum, rhodium, iridium, ruthenium or osmium; R represents hydrogen or alkyl, aryl, alkaryl, aralkyl, alkanoyloxy, alkoxy, aryloxy or cyanoalkyl radicals; Y represents phosphorus, arsenic, nitrogen, antimony or bismuth; and X is an anion; and (2) a compound of an element of Group I, II, III or IV of the Periodic System having at least one hydridic hydrogen bond. Many suitable catalyst components are specified and examples describe the use of (1) complexes of tributyl phosphine with nickel chloride, nickel nitrate, cobalt bromide, cobalt thiocyanate, palladium chloride, palladium nitrate and rhodium chloride; tricyanoethyl phosphine with nickel chloride, nickel bromide, nickel sulphate, nickel phosphate, nickel ferrocyanide and cobalt chloride; triphenyl phosphine with nickel chloride and nickel thiocyanate; triethyl phosphine with platinum chloride and ruthenium chloride; dibutyl phosphine with nickel chloride; butyl phosphine with nickel nitrate; triethyl arsine with nickel chloride, cobalt nitrate, palladium sulphate and rhodium phosphate; triphenyl arsine with platinum sulphate; triethyl stibine with cobalt phosphate; tributylamine with nickel chloride and iridium chloride; ammonia with cobalt chloride; diethyl arsine and ethyl stibine with palladium bromide; and triethyl arsine and triethyl phosphine with osmium chloride; and (2) lithium hydride, calcium hydride, diborane, monosilane, lithium, sodium, potassium calcium and aluminium borohydrides, ethyl sodium borohydride and dimethyl aluminium hydride. U.S.A. Specification 2,880,058 is referred to.ALSO:Acetylene and monosubstituted acetylenes are polymerized by contacting under polymerizing conditions with a catalyst comprising a mixture of (1) a complex of formula [M(R3Y)p]mXn wher m and n are 1 to 4 or when M is osmium 1 to 6; p is 1 to 6 or when M is osmium 1 to 8; M is nickel, cobalt, palladium, platinum, rhodium, iridium, ruthenium or osmium; R represents hydrogen, alkyl, aryl, alkaryl, aralkyl, alkanoyloxy, alkoxy, aryloxy or cyanoalkyl radicals; Y represents phosphorus, arsenic, nitrogen, antimony or bismuth; and X is an anion; and (2) a compound of an element of Group I, II, III or IV of the Periodic System having at least one hydridic hydrogen bond. Many groups by which acetylene may be substituted are listed and examples describe the polymerization of acetylene, propyne, pentyne-1, heptyne-1, heptadiyne-1,6, octadiyne-1,7, phenyl acetylene, propargyl alcohol, propargyl chloride, 3-diethylaminopropyne-1 and ethyl propiolate; and the copolymerization of heptyne-1 and pentyne, and propyne and acetylene. Many suitable catalyst components are specified and examples describe the use of (1) complexes of tributyl phosphine with nickel chloride, nickel nitrate, cobalt bromide, cobalt thiocyanate, palladium chloride, palladium nitrate and rhodium chloride; tricyanoethyl phosphine with nickel chloride, nickel bromide, nickel sulphate, nickel phosphate, nickel ferrocyanide and cobalt chloride; triphenyl phosphine with nickel chloride and nickel thiocyanate; triethyl phosphine with platinum chloride and ruthenium chloride; dibutyl phosphine with nickel chloride; butyl phosphine with nickel nitrate; triethyl arsine with nickel chloride, cobalt nitrate, palladium sulphate and rhodium phosphate; triphenyl arsine with platinum sulphate; triethyl stibine with cobalt phosphate; tributylamine with nickel chloride and iridium chloride; ammonia with cobalt chloride; diethyl arsine and ethyl stibine with palladium bromide; and triethyl arsine and triethyl phosphine with osmium chloride; and (2) lithium hydride, calcium hydride, diborane, monosilane, lithium, sodium, potassium, calcium and aluminium borohydrides, ethyl sodium borohydride and dimethyl aluminium hydride. Polymerization may be effected in liquid media, e.g. water, ethanol, dibetamethoxyethyl ether, acetonitrile, benzene and tetrahydrofuran. The products may be extracted with benzene petroleum ether, acetone and water, and comprise liquid polymers which may be used as drying oils in coating compositions, and solid, high molecular weight, linear polymers. The polymerization of butadiene and acrylonitrile is also referred to. U.S.A. Specification 2,880,058 is referred to.ALSO:Acetylene and monosubstituted acetylenes are polymerized by contacting under polymerizing conditions with a catalyst comprising a mixture of (1) a complex of formula [M(R3Y)p]mXn where m and n are 1 to 4 or when M is osmium 1 to 6; p is 1 to 6 or when M is osmium 1 to 8; M is nickel, cobalt, palladium, platinum, rhodium, iridium, ruthenium or osmium; R represents hydrogen or an alkyl, aryl, alkaryl, aralkyl, alkanoyloxy, alkoxy, aryloxy or cyanoalkyl radical; Y represents phosphorus, arsenic, nitrogen, antimony or bismuth; and X is an anion; and (2) a compound of an element of Group I, II, III or IV of the Periodic System having at least one hydridic hydrogen bond. Many groups by which acetylene may be substituted are listed and examples describe the polymerization of acetylene, propyne, pentyne-1, heptyne-1, heptadiyne-1,6, octadiyne-1,7, phenyl acetylene, propargyl alcohol, propargyl chloride, 3-diethylamino-propyne-1 and ethyl propiolate; and the copolymerization of heptyne-1 and pentyne, and propyne and acetylene. The polymers may be linear or aromatic, those described being linear except for those prepared from propargyl alcohol and phenyl acetylene which yield a mixture of aromatic and linear polymers. Many suitable catalyst components are specified and examples describe the use of (1) complexes of tributyl phosphine with nickel chloride, nickel nitrate, cobalt bromide, cobalt thiocyanate, palladium chloride, palladium nitrate and rhodium chloride; tricyanoethyl phosphine with nickel chloride, nickel bromide, nickel sulphate, nickel phosphate, nickel ferrocyanide and cobalt chloride; triphenyl phosphine with nickel chloride and nickel thiocyanate; triethyl phosphine with platinum chloride and ruthenium chloride; dibutyl phosphine with nickel chloride and butyl phosphine with nickel nitrate; triethyl arsine with nickel chloride, cobalt nitrate, palladium sulphate and rhodium phosphate; triphenyl arsine with platinum sulphate; triethyl stibine with cobalt phosphate; tributylamine with nickel chloride and iridium chloride; ammonia with cobalt chloride; diethyl arsine and ethyl stibine with palladium bromide; and triethyl arsine and triethyl phosphine with osmium chloride; and (2) lithium hydride, calcium hydride, diborane, monosilane, lithium, sodium, potassium, calcium and aluminium borohydrides, ethyl sodium borohydride and dimethyl aluminium hydride. Polymerization may be effected in liquid media, e.g. water, ethanol, dibetamethoxyethyl ether, acetonitrile, benzene and tetrahydrofuran. Phosphorus-containing complexes of the above formula may be prepared by mixing phosphines with metal salts in polar solvents such as ketones and alcohols from which the complexes crystallise on standing. In examples (1) tricyanoethyl phosphine is mixed with nickel bromide in acetone to give [P(CH2CH2CN)3]2NiBr2 (2) tricyanoethyl phosphine is mixed with nickel chloride in acetone to give [P(CH2CH2CN)3]2NiCl2; (3) triphenylphosphine is mixed with nickel chloride in acetic acid to give (#F3P)2NiCl2; (4 tributyl phosphine is mixed with nickel chloride in ethanol to give [(nC4H9)3P]2NiCl2 and (5) tributyl phosphine is mixed with palladium chloride in air-free water to give [(nC4H9)3P]2PdCl2.
GB4078560A 1960-11-28 1960-11-28 Polymerization of acetylene and mono-substituted acetylenes and catalysts therefor Expired GB889730A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4078560A GB889730A (en) 1960-11-28 1960-11-28 Polymerization of acetylene and mono-substituted acetylenes and catalysts therefor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4078560A GB889730A (en) 1960-11-28 1960-11-28 Polymerization of acetylene and mono-substituted acetylenes and catalysts therefor

Publications (1)

Publication Number Publication Date
GB889730A true GB889730A (en) 1962-02-21

Family

ID=10416595

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4078560A Expired GB889730A (en) 1960-11-28 1960-11-28 Polymerization of acetylene and mono-substituted acetylenes and catalysts therefor

Country Status (1)

Country Link
GB (1) GB889730A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110950382A (en) * 2018-09-26 2020-04-03 东泰高科装备科技有限公司 Process for the preparation of arsine
RU2754530C1 (en) * 2020-11-30 2021-09-03 Федеральное государственное бюджетное образовательное учреждение высшего образования "Иркутский государственный университет" (ФГБОУ ВО "ИГУ") Method for obtaining phenylacetylene oligomers (variants)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110950382A (en) * 2018-09-26 2020-04-03 东泰高科装备科技有限公司 Process for the preparation of arsine
CN110950382B (en) * 2018-09-26 2022-03-15 紫石能源有限公司 Process for the preparation of arsine
RU2754530C1 (en) * 2020-11-30 2021-09-03 Федеральное государственное бюджетное образовательное учреждение высшего образования "Иркутский государственный университет" (ФГБОУ ВО "ИГУ") Method for obtaining phenylacetylene oligomers (variants)

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