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    Production of axerophthyl phosphonium salts
    13.
    发明专利
    Production of axerophthyl phosphonium salts 未知

    公开(公告)号：GB969180A

    公开(公告)日：1964-09-09

    申请号：GB1965863

    申请日：1963-05-17

    Applicant: BASF AG

    Inventor： SARNECKI WILHELM ,  NUERRENBACH AXEL ,  REIF WERNER

    IPC: C07F9/54

    Abstract: Quaternary axerophthyl phosphonium salts are prepared by reacting an ester of vitamin A alcohol (axerophthol) with a tertiary phosphine and an acid or with acid addition salts of tertiary phosphines A solvent may be used. Preferred temperatures are from 0-80 DEG C., but -20 to +120 DEG C. may be used. The initial material may be a waste liquor containing a vitamin A ester obtained in the production and purification of vitamin A esters. Specified phosphines are triphenyl, tri-p-tolyl and trianisyl phosphines. Suitable acids include sulphuric acid, organic sulphonic acids and fluorboric acid. Specified vitamin A esters are the acetate, propionate and palmitate. The vitamin A esters may be in the cis- or trans-form. Specification 812,522 is referred to.

    Improvements in the production of compounds of the beta-cyclogeranylidene series
    14.
    发明专利
    Improvements in the production of compounds of the beta-cyclogeranylidene series 未知

    公开(公告)号：GB877351A

    公开(公告)日：1961-09-13

    申请号：GB873559

    申请日：1959-03-13

    Applicant: BASF AG

    Inventor： POMMER HORST ,  SARNECKI WILHELM

    IPC: A23L1/275 ,  C07C403/00

    Abstract: Compounds containing the beta - cyclogeranylidene compound e.g. vitamin A acid and esters, b -ionylidene ethanol, b -ionylidene acetic acid ethyl ester, axerophthene, homoisopreno-vitamin A acid, dehydro-b -carotene and vitamin A acetate are prepared by replacing the oxygen of an oxo group in an oxo compound by the group wherein n is 0, 1, 2, 3 or 4 and R is H or CH3 by combining the alcohol with a triarylphosphine and a proton donor, for example by adding the hydrogen acid salt of the triaryl phosphine R3PH.X wherein R is an aromatic radical and X is an anion, and after adding a proton acceptor such as an inorganic or organic base or an organo-metallic compound, condensing with the oxo compound. The oxo compound may suitably be an aldehyde or dialdehyde, a ketone, or a formic acid ester, many being specified. The reaction is preferably carried out in a polar solvent such as dimethyl formamide, acetonitrile, methanol, an acetic ester or nitrobenzene and at a temperature of -20 DEG C. to 30 DEG C. Trans-b -formylcrotonic acid used as an oxo reactant in the above processes is made by alkaline saponification of the diethylacetal of formyl-crotonic acid ethyl ester and deacetalisation of the product. Specifications 784,628 and 822,865 are referred to.

    Ylenals and process for their production
    16.
    发明专利
    Ylenals and process for their production 未知

    公开(公告)号：GB1079216A

    公开(公告)日：1967-08-16

    申请号：GB4822664

    申请日：1964-11-27

    Applicant: BASF AG

    Inventor： FREYSCHLAG HERWIG ,  REIF WERNER ,  NUERRENBACH AXEL ,  SARNECKI WILHELM

    IPC: A01N57/22 ,  C07F9/535

    Abstract: The invention comprises ylenals, (i.e. compounds which in the same molecule contain a phosphorylene group and an aldehyde group in conjunction) of the formula where Ar is an aryl radical which may be substituted by alkyl or alkoxy groups; R1, R2 and R3 are H or alkyl groups and n is an integer from 1 to 6. They may be obtained by reacting a proton acceptor in liquid phase with a quaternary phosphonium salt of the formula where X(-) is a monovalent anion. Suitable proton acceptors are bases having a pK value below or about 9 such as alcoholates, ammonia, amines, e.g. alkylamines or heterocyclic amines, or aqueous alkali. Suitable solvents are water, dimethyl-formamide or sulphoxide, acetonitrile, alcohol, hydrocarbons, halogenated hydrocarbons or mixtures thereof. Specified products are triphenylphosphine-2-formylpropen-1-yl-1-methylene, triphenylphosphine-3-formylpropen-(2)-yl-2-methylene, triphenylphosphine-2 - methyl - 4 - formylbutadien - (1,3) - yl - 1 - methylene, triphenylphosphine-1-methyl-4-formylbutadiene - (1,3) - yl - 1 - methylene, and triphenylphosphine - 2,6 - dimethyl - 6 - formylhexatrien - (1,3,5) - yl - 1 - methylene. Examples are given for the preparation of triphenylphosphine - 2 - formylpropen - 1 - yl-methylene. The products are intermediates for the synthesis of dyes, pharmaceuticals, plant protection agents, food dyes and carolenoids. The phosphonium salts of Formula I may be obtained by reacting a suitable halogen compound with a triarylphosphine in an organic solvent.

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