Preparation of unsaturated compounds by hydrolysis of xanthate-lewis acid complexes

申请号 US3666738D 申请日 1969-09-10 公开(公告)号 US3666738A 公开(公告)日 1972-05-30
申请人 TEE PAK INC; 发明人 BURKE NOEL I; BRIDGEFORD DOUGLAS J; TURBAK ALBIN F;
摘要 Simple and complex unsaturated compounds are prepared by decomposition of certain xanthate ester - Lewis acid complexes. Xanthate esters of the form: WHERE R is an alkyl function having at least one H in a position alpha to the R - O bond, (C)n is a linear alkyl function either substituted or unsubstituted, with n 1 - 3, X has a basicity greater than the FUNCTION AND COMPRISES A C or S containing functional group having at least one double or triple bond to a hetero atom, the functional group being connected to (C)n through C or S; are reacted with Lewis acids, either neat or in non-protonic nonaqueous solvents, to yield a Lewis acid complex of the esters. The Lewis acid - xanthate ester complex is decomposed by admixture with water or a protonic non-aqueous solvent, e.g. methanol, ethanol, etc., glycol, cellosolve, liquid ammonia, lower alkyl primary or secondary amines, aniline, etc., to yield an unsaturated derivative of R.
权利要求
  • 2. A method in accordance with claim 1 in which R is alkyl or cycloalkyl, either unsubstituted or containing inert substituents.
  • 3. A method in accordance with claim 1 in which R is polymeric.
  • 4. A method in accordance with claim 1 in which R is cellulose, starch, amylose, or polyvinyl alcohol.
  • 5. A method in accordance with claim 1 in wHich the xanthate ester is a diester or polyester.
  • 6. A method in accordance with claim 1 in which X is
  • 7. A method in accordance with claim 1 in which R is polyvinyl alcohol and the unsaturated product is polyacetylene or a copolymer of acetylene and vinyl alcohol.
  • 8. A method in accordance with claim 1 in which R is a copolymer of vinyl alcohol and acetylene and the unsaturated product is polyacetylene or a copolymer of vinyl alcohol and acetylene having a higher acetylene content than the initial reactant.
  • 9. A method in accordance with claim 1 in which the xanthate ester complex is prepared by reacting a Lewis acid with a xanthate ester of the formula neat or in a non-aqueous solvent.
  • 10. A method in accordance with claim 9 in which the Lewis acid is of a strength sufficient to complex preferentially with X and does not form a complex with the solvent which is as strong as the X:A complex.
  • 11. A method in accordance with claim 1 in which R is cellulose, starch, amylose, or polyvinyl alcohol, (C)n is
  • 12. A method in accordance with claim 11 in which R is cellulose.
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