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    Production of 1,5 cyclo-octadiene from butadiene and catalysts for use therein
    1.
    发明专利
    Production of 1,5 cyclo-octadiene from butadiene and catalysts for use therein 未知

    公开(公告)号：GB943697A

    公开(公告)日：1963-12-04

    申请号：GB2442961

    申请日：1961-07-06

    Applicant: BASF AG

    Inventor： KUTEPOW NIKOLAUS VON ,  SEIBT HUBERTUS ,  MEIER FRITZ

    IPC: B01J31/18 ,  B01J31/20 ,  C07C2/46 ,  C07F15/04

    Abstract: The invention comprises a compound of the general formula: in which R is an alkyl or aromatic radical, Z is an a , b -unsaturated aldehyde or an a ,b -unsaturated nitrile, x is 2 or 3 and y is O or 1, the sum of x and y being les than or equal to 3. Such compounds and similar phosphite-containing nickel complexes with less than four ligands may be obtained by reacting an organic nickel complex containing O-valent nickel and which is free from carbon monoxide groups with a triester of phosphorous acid in an inert solvent or diluent with substantial exclusion of oxygen. Suitable nickel complexes for use in the process are nickel (O)-bis-acrylonitrile, nickel(O)-bis-cinnamonitrile, nickel(O)-bis-fumaronitrile, and nickel(O)-bis-acrolein. The group R in the phosphite may be the radical of a C1-C12 alkano or of a phenol or naphthol which may be substituted by alkyl or aryl radicals, alkoxy groups or halogen atoms, e.g. chlorine. The reaction is suitably carried out at from 20 DEG to 120 DEG C. at normal pressure but higher or lower pressures may be used. Suitable solvents are hydrocarbons, ethers, and nitriles of lower fatty acids e.g. acetonitrile or propionitrile. Examples are given for the production of the following complexes: tris-(tri-m-tolyl-phosphite)-nickel, and complexes obtained from nickel(O)-bis-acrylonitrile and tri-(a -naphthyl)-phosphite, tri-(2,4-dimethylphenyl)-phosphite, and tri-(p-tertiary-butylphenyl)-phosphite respectively. The products are useful as catalysts for the dimerisation of butidiene to form cyclooctadiene-1,5 (see Division C5).ALSO:Cyclooctadiene-(1,5) is obtained by dimerization of butadiene at an elevated temperature of at least 50 DEG C. in the presence of a catalyst consisting of a nickel complex with less than four ligands which has been obtained by reaction of an organic nickel complex compound free from carbon monoxide groups and containing O-valent nickel with a triester of phosphorous acid in an inert solvent or diluent with substantial exclusion of oxygen (see Division C2). Particularly suitable catalysts are the complexes obtained from a triester of phosphorous acid and nickel (O) complexes with a ,b -unsaturated aldehydes or a ,b -unsaturated nitriles, e.g. acrolein, g -bromocrotonaldehyde, acrylonitrile, cinnamonitrile, and fumaronitrile. The triester of phosphorous acid may be derived from a C1-C12 alkanol or from a phenol or naphthol which may be substituted by an alkyl, aryl or alkoxy group or by a halogen atom, e.g. chlorine. The dimerization of the butadiene is preferably carried out in the presence of a solvent or diluent, e.g. a hyrocarbon, a liquid carboxylic acid amide, a cyclic ether, a nitrile or a ketone and a polymerization inhibitor, e.g. hydroquinone may be present. Suitable dimerization temperatures are from 50 DEG to 250 DEG C. and it is preferred to operate at an elevated pressure, e.g. 3 to 20 atmospheres. Higher pressures may also be used by forcing in an inert gas such as nitrogen, rare gases, saturated or mono-olefinic gaseous hydrocarbons or carbon dioxide. The process may also be carried out at normal pressure, e.g. by blowing butadiene in gaseous form into a solution of the catalyst in a suitable solvent. The butadiene may be used pure or in admixture with other hydrocarbons, e.g. those obtained in the cracking of higher hydrocarbons. The process may be carried out batchwise, continuously, or semi-continuously. Small amounts of 4-vinyl-cyclohexene-(1) may be obtained as by-product. Examples are given in which the following complexes are used as catalysts: tris-(tri m-tolyl phosphite nickel, nickel (O)-bis-(p-tertiarybutylphenyl)-phosphite, tris-(tri-phenyl phosphite) nickel and the complexes obtained from nickel (O)-bis-acrylonitrile and tri-2,4-dimethylphenyl phosphite tri-(a -naphthyl) phosphite and tri-4-isooctyl phenyl phosphite respectively.

    Production of oligomers of butadiene (1,3)
    3.
    发明专利
    Production of oligomers of butadiene (1,3) 未知

    公开(公告)号：GB1009017A

    公开(公告)日：1965-11-03

    申请号：GB3142462

    申请日：1962-08-16

    Applicant: BASF AG

    Inventor： WITTENBERG DIETMAR ,  LAUTENSCHLAGER HANS ,  KUTEPOW NIKOLAUS VON ,  MEIER FRITZ ,  SEIBT HUBERTUS

    IPC: C07C2/46 ,  C07C2/52 ,  C07F9/02 ,  C07F9/145 ,  C07F9/6574

    Abstract: Cyclic olefins are obtained by the polymerization of butadiene in the presence of a catalyst prepared from (a) a compound of iron, cobalt or nickel; (b) a hydride or organo-compound of an element of Group Ia, IIa, IIb or IIIa (i.e. non-transitional elements of Group III) and (c) a phosphite having an aryl radical with a substituent ortho to the phosphite group or a condensed 6-membered ring ortho and meta to the phosphite group. The constituent (a) is preferably an inorganic or organic salt or a chelate compound of nickel or cobalt. The ortho substituent in the aryl phosphite, which may be derived from benzene, naphthalene or diphenyl, may be an alkyl, alkoxy, halogen or aryloxy or together with the aryl group may form a fused, six-membered, carbocyclic ring. The other two phosphite substituents may be the same or different. The mol ratio of (a) : (b) : (c) may be 1 : 0.5-20: 1-4, the amount by weight of (a) being 0.001-0.1 times that of butadiene. A hydrocarbon or ether solvent, including reaction products, may be present and the temperature may be 0-250 DEG C. with sufficient pressure to maintain liquid phase. Octadiene-1,5 is the principal product. Specification 917,103 is referred to.

    Production of carboxylic acids
    4.
    发明专利
    Production of carboxylic acids 未知

    公开(公告)号：GB1137163A

    公开(公告)日：1968-12-18

    申请号：GB1655966

    申请日：1966-04-15

    Applicant: BASF AG

    Inventor： KUTEPOW NIKOLAUS VON ,  BITTLER KNUT ,  MEIER FRITZ ,  NEUBAUER DIETER

    IPC: C07C51/145

    Abstract: 1,137,163. Carboxylic acids. BADISCHE ANILIN- & SODA-FABRIK A.G. 15 April, 1966 [17 April, 1965], No. 16559/66. Heading C2C. Carboxylic acids are prepared from olefinically unsaturated compounds, carbon monoxide, and water at elevated temperature in the presence of palladium and/or a palladium compound and an oxidizing agent with an oxidation potential of more than 0À1 volt, at from 30‹ to 210‹ C. Unsaturated compounds may be ethylene, vinyl chloride, propene, butene-(2), hexene-(3), dodecene-(1), 2-ethylhexene-(1), propenylbenzene, vinylcyclohexene-(3), cyclohexene, cyclooctene, cyclododecene, butadiene-(1,3), isoprene, piperylene, cyclooctadiene-(1,5), octatriene- (2,4,6), methylheptatriene, cycloheptatriene- (1,3,5), cyclododecatriene - (1,5,9), 1 - chlorocyclododecadiene - (5,9), cyclooctatetraene, ethyl acrylate, acrylonitrile, acrylamide, allyl alcohol, allyl chloride, oleic acid, ricinoleic acid, undecylenic acid, methyl allyl ether, cyclohexadienes and acrolein. The oxidizing agent may be iodine, peroxides, persulphates, lead dioxide, manganese dioxide, copper (II) chloride, potassium permanganate, potassium dichromate, benzoquinone, oxygen, or the oxidation may be by electro-chemical means with an anode at the appropriate potential. Examples describe the preparation of propionic acid, cyclododecadiene- (5,9)-monocarboxylic acid-(1) which may be hydrogenated to cyclododecane monocarboxylic acid, and butene-(2) carboxylic acid-(1).

    Esterification of ª‡,ª‰-unsaturated carboxylic acids with alkylene oxides
    10.
    发明专利
    Esterification of ª‡,ª‰-unsaturated carboxylic acids with alkylene oxides 未知

    公开(公告)号：GB997959A

    公开(公告)日：1965-07-14

    申请号：GB4864963

    申请日：1963-12-10

    Applicant: BASF AG

    Inventor： MEIER FRITZ ,  KUTEPOW NIKOLAUS VON

    IPC: B01J31/02 ,  C07C67/26

    Abstract: Hydroxy esters of the general formula wherein R is hydrogen or alkyl, R1 is hydrogen or alkyl and R11 is hydrogen, alkyl or chloromethyl are made by reacting, preferably at 70 DEG to 120 DEG C., and with advantage in the presence of a solvent, the carboxylic acid of the general formula especially acrylic, methacrylic or crotonic, with an alkylene oxide of the general formula especially 1,2-propylene oxide, 1,2-butylene oxide or epichlorohydrin, in the presence of, as esterification catalyst, a carboxylic amide, a urea, or a lactam or amide of a heterocyclic base. Named catalysts are N-methyl formamide, dimethyl formamide, dibutyl formamide, dimethylacetamide, N,N1 - dimethyl urea, N - formyl pyrrolidine, N-formyl morpholine, N-formyl piperazine, pyrrolidone, e -caprolactam. In the examples the following are prepared using as catalyst: glycol monoacrylate (dimethyl formamide = D.M.F.), 2-hydroxypropyl acrylate (D.M.F.), 3 - chloro - 2 - hydroxy - propyl acrylate (D.M.F.) and (formamide), 2-hydroxypropyl crotonate (D.M.F.), 2-hydroxypropyl methacrylate (dimethyl acetamide), 2-hydroxypropyl acrylate (dimethyl acetamide).

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