Process for the production of nitrate esters of alpha-hydroxy-carboxylic acids from alpha-olefins
    5.
    发明授权
    Process for the production of nitrate esters of alpha-hydroxy-carboxylic acids from alpha-olefins 失效
    从α-烯烃生产α-羟基羧酸的硝酸酯的方法

    公开(公告)号:US3324168A

    公开(公告)日:1967-06-06

    申请号:US52883066

    申请日:1966-02-21

    Applicant: CHEMIE LINZ AG

    CPC classification number: C07C203/04 C07C201/02

    Abstract: The invention comprises nitrates of the formula wherein R1 is C4- 12 straight chain alkyl and X is hydrogen or straight-chain alkyl group and a more general method of preparation of compounds of the formula where R is a straight chain alkyl group of at least 3 carbon atoms comprising introducing a mixture of one or more straight chain a -olefins, having at least 5 carbon atoms, and molecular oxygen into liquid dinitrogen tetroxide at - 10 DEG to +40 DEG C., removing excess nitrous fumes at a temperature not exceeding 60 DEG C. and, if desired, esterifying the carboxyl group in a known manner. The oxygen and dinitrogen tetraoxide are used in at least equimolar amounts, based on olefin. The reaction may be effected in the presence of an oxidation catalyst, e.g. SeO2 or V2O5. The starting olefin may be used in the form of a commercial mixture containing saturated hydrocarbons which act as a diluent. The excess nitrous fumes are conveniently removed from the product using a thin film evaporator. Examples relate to the nitrate esters of methyl-a -hydroxyvalerate, methyl - a - hydroxyoenanthate, a -hydroxycaprylic acid, a -hydroxycapric acid, a -hydroxylauric acid, a -hydroxymyristic acid, a -hydroxypelargonic acid, a -hydroxystearic acid, a -hydroxyarachidic acid and a -hydroxy-nonadecane carboxylic acid.

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