Method for preparing organotin compounds

• US 4,104,292 A
• Filed: 11/02/1976
• Issued: 08/01/1978
• Est. Priority Date: 11/02/1976
• Status: Expired due to Term

• Current Assignee: Elf Atochem North America, Inc. (Totalenergies Se)
• Original Assignee: M&T Chemicals Incorporated
• Inventors: Ejk, Adam J., Dworkin, Robert D.
• Primary Examiner(s): Sneed, Helen M. S.
• Application Number:
  US05/738,183
• Time in Patent Office: 637 Days
• Field of Search: 260/429.7, 260/410, 260/410.6, 260/399
• US Class Current: 556/93
• CPC Class Codes: C07F 7/226 Compounds with one or more Sn-S linkages

Abstract

Organotin derivatives of mercaptoalcohol esters corresponding to the general formula ##STR1## WHEREIN R and R'"'"' are hydrocarbon, m is 2 or 3 and q is 1 or 2 are prepared by reacting a mercaptoalcohol of the formula HS(CH₂)_m OH with a diorganotin oxide, organostannoic acid or an anhydride of said acid in an aqueous medium and subsequently esterifying the reaction product with the desired carboxylic acid, R'"'"'COOH, or an ester thereof. The present method offers advantages over the prior art, which teaches reacting an esterified mercaptoalcohol with an organotin compound. Compounds wherein R'"'"' is n-heptyl are unique in that they do not exhibit the disagreeable odors that characterize this class of compounds.

Claims

1. A method for preparing an organotin compound of the general formula ##STR3## wherein R and R'"'"' are individually selected from the group consisting of alkyl containing from 1 to 20 atoms, cycloalkyl, aryl, alkaryl and aralkyl, m represents the integer 2 or 3 and q represents the integer 1 or 2, said method consisting essentially of the following sequence of steps:

(1) combining 4-q moles of 2-mercaptoethanol or 3-mercaptopropanol for every one mole of an organostannoic acid, RSnOOH, when q is 1 or a diorganotin oxide, R₂ SnO, when q is 2, and heating the resultant mixture at a temperature of from 40°

to 100°

C and for a period of time sufficient to substantially complete the reaction;

(2) combining the resultant product with a stoichiometric quantity of a carboxylic acid R'"'"'COOH, or an ester thereof, R'"'"'COOR", wherein R" is alkyl and contains from 1 to 20 carbon atoms, and subsequently removing the aqueous phase of the reaction mixture;

(3) heating the organic phase of said reaction mixture to a temperature of from 100°

to about 180°

C and simultaneously removing any by-product water or any alcohol boiling at or below the temperature of the reaction mixture;

(4) removing the resultant organotin compound, ##STR4## from the reaction vessel.

2. A method as set forth in claim 1 wherein R and R'"'"' are individually selected from the group consisting of radicals containing from 1 to 20 carbon atoms.

3. A method as set forth in claim 2 wherein R is butyl.

4. A method as set forth in claim 1 wherein said carboxylic acid is caprylic acid or pelargonic acid.

5. A method as set forth in claim 1 wherein m is 2.

6. A method as set forth in claim 1 wherein R" contains from 1 to 4 carbon atoms.

7. A method as set forth in claim 1 wherein the reaction between the mercaptoalcohol and the organotin compound is conducted in an aqueous medium.

8. A method as set forth in claim 1 wherein the product of step 1 is reacted with an ester of the formula R'"'"'COOR" wherein R" contains from 1 to 10 carbon atoms and the resultant alcohol R"OH is removed by distillation prior to isolating said organotin compound.

9. A method as set forth in claim 1 wherein the product of step 1 is reacted with an ester of the formula R'"'"'COOR" wherein R" contains from 10 to 20 carbon atoms and the resultant alcohol R"OH is isolated as a mixture with said organotin compound.

10. A method for preparing an organotin compound of the general formula ##STR5## wherein R and R'"'"' are individually selected from the group consisting of alkyl containing from 1 to 20 carbon atoms, cycloalkyl, aryl, alkaryl and aralkyl, m is the integer 2 or 3 and q is the integer 1 or 2, said method consisting essentially of the following sequence of steps:

(1) reacting an organotin halide of the formula R_q SnX_4-q wherein X is chlorine, bromine or iodine with (a) an aqueous solution of an inorganic base at ambient temperature, such that the number of equivalent weights of said base is at least equal to the number of moles of X atoms present in the reaction mixture;

(2) combining the resultant product with 4-q moles of 2-mercaptoethanol or 3-mercaptopropanol, and heating the mixture to a temperature of from 40°

to 100°

C and for a period of time sufficient to substantially complete said reaction;

(3) combining the resultant product with a stoichiometric quantity of a carboxylic acid R'"'"'COOH, or an ester thereof, R'"'"'COOR", wherein R" is alkyl and contains from 1 to 20 carbon atoms, and subsequently removing the aqueous phase of the reaction mixture;

(4) heating the organic phase of said reaction mixture to a temperature of from 100°

to about 180°

C and simultaneously removing any by-product water or any alcohol boiling at or below the temperature of the reaction mixture;

(5) removing the resultant organotin compound, ##STR6## from the reaction vessel.

11. A method as set forth in claim 10 wherein R and R'"'"' are individually selected from the group consisting of alkyl radicals containing from 1 to 20 carbon atoms.

12. A method as set forth in claim 11 wherein R is butyl.

13. A method as set forth in claim 10 wherein said carboxylic acid is caprylic acid or pelargonic acid.

14. A method as set forth in claim 10 wherein m is 2.

15. A method as set forth in claim 10 wherein X is chlorine.

16. A method as set forth in claim 10 wherein the base reacted with the organotin halide is ammonium hydroxide.

17. A method as set forth in claim 10 wherein R" contains from 1 to 4 carbon atoms.