Alkane sulphonic acid esters substituted in ª -position by ether groups and their production

    公开(公告)号:GB923766A

    公开(公告)日:1963-04-18

    申请号:GB3197461

    申请日:1961-09-06

    Applicant: BASF AG

    Abstract: The invention comprises compounds of formula R1-O-CR2R3-CHR4-SO2-O-R5 which contain at least nine carbon atoms, where R1 is a C1-C20 alkyl group, a C3-C20 alkenyl group, a cycloalkyl group with 5 to 12 carbon atoms in the ring, a C2-C12 hydroxy alkyl group, a C3-C12 alkoxyalkyl group, a C4-C23 dialkylaminoalkyl group or an alkylarylaminoalkyl group with up to 23 carbon atoms; R2-R4 are hydrogen atoms or C1-C3 alkyl groups; R5 is a C1-C18 alkyl group, a C6-C15 aryl group, a C7-C13 alkoxyaryl group, a C6-C12 halogenaryl group or a C7 thiocyanoaryl group. The invention also includes a process for making compounds of the above formula, without the restriction to 9 upon the total number of carbon atoms in their molecules, by treating the corresponding vinyl sulphonic acid ester with an excess of alcohol in the presence of 0.02-0.1 equivalent per mol. of ester of an alkali or alkaline earth metal alcoholate, a dry alkali hydroxide or a quaternary ammonium base of the formula [R1R11NR111R1111]+ OH-wherein R1, R11 and R111 are C1-C3 alkyl groups and R1111 is a C6-C10 aryl group, a C7-C9 aralkyl group or a cycloalkyl group having 5 to 12 carbon atoms in the ring. Inert solvents may be present. The temperature may be in the range -10 to 100 DEG C. but preferably the reactants are mixed at a lower temperature and slowly heated. The alcohol may be present in 1.3 times the stoichiometrical amount but is generally used in considerable excess, e.g. 2 to 8 times the stoichiometrical amount. The esters may be hydrolysed to form the free acids or salts thereof which have surface-active properties when R1 has at least 6 carbon atoms. Preferred starting esters are derived from vinylsulphonic acid, a -methylvinylsulphonic acid and 1-propene sulphonic acid and from phenols and naphthols which may contain one to three inert groups such as alkyl, alkoxy, halogen and thiocyanate groups. Typical of specified alcohols are propanol, 2-ethylhexanol, allyl alcohol, palmityl alcohol, butane-1,4-diol, dodecane-1, 12-diol, glycol monomethyl ether, triglycol, methylstearylaminoethanol, cyclopentanol, cyclooctanol, benzyl alcohol and phenylmethyl carbinol. Esters containing aryl residues in the ester group and 4-20 carbon atoms in the ether group are plasticisers for polyvinyl chloride. Examples given include the preparation of b -allyloxy-ethane sulphonic acid cresyl ester, b -nonyloxy-ethanesulphonic acid methyl ester, b (NN-dimethyl-2-aminoethoxy)-ethane sulphonic acid cresyl ester, b -cyclohexyloxyethanesulphonic acid-a -naphthyl ester, b -allyloxy-ethanesulphonic acid-2-chlorophenyl ester, and also the use of vinylsulphonic acid o-bromophenyl ester, vinylsulphonic acid p-iodophenyl ester, vinylsulphonic acid p-fluorophenyl ester and vinylsulphonic acid p-thiocyanophenyl ester.

    Improvements in the production of cyanuric acid and alkali metal cyanurates

    公开(公告)号:GB865294A

    公开(公告)日:1961-04-12

    申请号:GB3247759

    申请日:1959-09-24

    Applicant: BASF AG

    Abstract: In a process for the production of cyanuric acid by heating urea in a water immiscible organic liquid which does not dissolve or attack the urea or cyanuric acid, after the urea has been reacted, the reaction mixture contained in the reaction vessel is treated with a solution of potassium or sodium hydroxide, acetate, carbonate, or formate in water or a water/alcohol mixture and the resulting cyanurate solution is separated from the water immiscible organic liquid. The use of aqueous solutions of sodium or potassium hydroxide containing less than 25% wt. of the sodium or potassium hydroxide is preferred. The reaction mixture is preferably treated with an amount of solution sufficient to cause the cyanuric acid to be substantially converted into the corresponding trialkali metal cyanurate. The resulting solution of cyanurate after isolation from the water immiscible organic liquid which may subsequently be returned to the reaction vessel, may be reacted with chlorine to yield tri or dichloro cyanuric acid or be acidified with mineral acids to recover the cyanuric acid. Alcohols specified for use in the water/alcohol mixtures are methanol, ethanol, or isopropanol, the alcohol being present in amount sufficient only to ensure complete solution of the sodium or potassium compounds therein.

    Continuous production of 1,4,5,6,7,7-hexachlorobicyclo-[2,2,1]-5-heptene-2,3-dicarboxylic acid

    公开(公告)号:GB1139311A

    公开(公告)日:1969-01-08

    申请号:GB2125566

    申请日:1966-05-13

    Applicant: BASF AG

    Abstract: 1,139,311. Chlorendic acid. BADISCHE ANILIN- & SODA-FABRIK A.G. 13 May, 1966 [14 May, 1965], No. 21255/66. Heading C2C. In the manufacture of chlorendic acid [1,4,5, 6,7,7 - hexachlorobicyclo - (2,2,1) - 5 - heptene- 2,3-dicarboxylic acid] by reacting hexachlorocyclopentadiene with maleic anhydride at atmospheric, reduced or raised pressure and hydrolysing the product, the reagents are fed continuously into a reactor kept at a temperature of 120-200‹ C. in which they remain for 2-7 hours, whereafter the product is allowed to flow into water at a temperature of at least 70‹ C., the solution is treated first with superheated steam, to remove chlorohydrocarbons, and then with a fatty acid of 1-3 carbon atoms, or a chloro-derivative of such an acid, and finally, the solution is cooled to crystallize the product. No solvent need be used. Examples are given, and apparatus is described.

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