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    Process for the production of nitrate esters of alpha-hydroxy-carboxylic acids from alpha-olefins
    61.
    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

    Inventor： WALTER MULLER ,  FERDINAND WEINROTTER

    IPC: C07C51/275 ,  C07C203/04

    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.

    Esterification of polyvalent alkanols with nitric acid in liquid sulphur dioxide
    62.
    发明授权
    Esterification of polyvalent alkanols with nitric acid in liquid sulphur dioxide 失效
    用硝酸在液态二氧化硫中酯化多元链烷醇

    公开(公告)号：US3316289A

    公开(公告)日：1967-04-25

    申请号：US58174066

    申请日：1966-09-26

    Applicant: STAMICARBON

    Inventor： DOESBURG JOHAN T SEMEYNS DE VR ,  DEUMENS JOHANNES J M

    IPC: C07C201/02

    CPC classification number: C07C201/02 ,  C07C203/04

    Abstract: 1,138,360. Nitric esters of polyalkanols. STAMICARBON N.V. 26 Sept., 1966 [1 Oct., 1965], No. 42957/66. Heading C2C. Polyhydric alkanols are esterified with nitric acid by reacting with a nitrating acid in a liquid sulphur dioxide medium. Glycerol di- and trinitrates, ethylene glycol dinitrate and diethylene glycol dinitrate are specified and the nitrating acid is a mixture of nitric and sulphuric acid or anhydride with a preferred nitric acid content of 38-43 mol. per cent. The autogenous oxidation of liquid sulphur dioxide removes the heat generated during esterification.

    Manufacture of nitric acid esters
    67.
    发明授权
    Manufacture of nitric acid esters 失效
    硝酸酯的制造

    公开(公告)号：US2294849A

    公开(公告)日：1942-09-01

    申请号：US22590838

    申请日：1938-08-20

    Applicant: SHARPLES CHEMICALS INC

    Inventor： OLIN JOHN F ,  FRITSCH FREDERICK P ,  SCHAEFER JOSEPH J

    IPC: C07C201/02

    CPC classification number: C07C201/02 ,  C07C203/04 ,  C07C203/08 ,  C07C2601/14

    Abstract: 540,050. Alkyl nitrates. STEVENS, A. H. (Sharples Solvents Corporation). March 29, 1940, No. 5722. Drawings to Specification. [Class 2 (iii)] Alkyl nitrates are produced by reacting in alcohol with nitric acid of 35-68 per cent. strength under a pressure of 20-650 mm., the nitrate being removed by azeotropicdistillation, water (or in the case of ethyl or methyl nitrate, the ester) being returned from the distillate or otherwise to the reaction vessel to prevent accumulation of ester or water. The invention is applicable to the esterification of dihydric alcohols. Urea is preferably added during the process, and the water to be returned may be added in the form of solvent or diluent of the nitric acid, urea or alcohol. Examples 1-11 describe the esterification of n-butyl, 2-chlorethyl, mixed amyl, secondary amyl, iso-amyl, n-amyl, n-hexyl, secondary hexyl, 2-ethoxyethyl, cyclohexyl, and octyl nitrates, using the reagents in the liquid phase. The alcohol may be supplied in the liquid or vapour phase. Another example describes the production of isopropyl nitrate, the alcohol being supplied in the form of vapour above the surface of the nitric acid. Specification 379,312 is referred to.

    Production of secondary aliphatic nitrates
    69.
    发明授权
    Production of secondary aliphatic nitrates 失效
    二次脂肪族硝酸盐的生产

    公开(公告)号：US2225893A

    公开(公告)日：1940-12-24

    申请号：US26497939

    申请日：1939-03-30

    Applicant: STANDARD OIL DEV CO

    Inventor： VANDERBILT BYRON M

    IPC: C07C201/02 ,  C10L1/23

    CPC classification number: C10L1/231 ,  C07C201/02 ,  C07C203/04

    Abstract: 538,446. Ethereal nitrates. STANDARD OIL DEVELOPMENT CO. Feb. 8, 1940, No. 2476. Convention date, March 30, 1939. [Class 2 (iii)] Secondary aliphatic nitrates are produced by nitrating compounds containing a secondary alcohol group at a temperature not above -10‹C. using a nitration mixture containing at least 50 per cent. excess of nitric acid and also sulphuric acid and water, the molecular ratio of water to sulphuric acid being not greater than 1.6 + .004 (E-50) where E is the percentage excess of nitric acid. A part of the sulphuric acid may be replaced by an acid of phosphorus or a water-soluble fatty acid, such as phosphoric or acteic acid, in which case the lower limit of nitric acid may be used ; otherwise the excess of nitric acid should be at least 100 per cent. Examples describe the production of the nitrate of secondary amyl alcohol, and it is stated that other alcohols that may be used are substituted and unsubstituted mono- and polyhydric alcohols such as isopropyl alcohol, 2 hydroxyhexane, 2-3 dihydroxybutane, 2-3 dihydroxypentane, 2-methyl-2-nitro-1:3-dihydroxybutane, 3-chloro-2-hydroxybutane, the secondary alcohols prepared by hydration of olefines containing up to 12 or 14 carbon atoms (from the cracking of paraffin wax) and 1-12-dihydroxyoctadecane.

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