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US4104292A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for preparing organotin compounds

Assignee: Arkema Inc
•
Filing: 1976-11-02
•
Granted: 1978-08-01
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Expires: 1996-11-02
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Abstract

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(CH 2 ) 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.

Inventors

  • 👤 Robert D. Dworkin
  • 👤 Adam J. Ejk

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 13:26
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/22; C07F7/226

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 209 words
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, R 2 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.
Claim 2
Independent Claim 209 words
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, R 2 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.
Claim 3
Dependent Claim 28 words
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.
Claim 4
Dependent Claim 12 words
A method as set forth in claim 2 wherein R is butyl.
Claim 5
Dependent Claim 18 words
A method as set forth in claim 1 wherein said carboxylic acid is caprylic acid or pelargonic acid.
Claim 6
Dependent Claim 12 words
A method as set forth in claim 1 wherein m is 2.
Claim 7
Dependent Claim 17 words
A method as set forth in claim 1 wherein R" contains from 1 to 4 carbon atoms.
Claim 8
Dependent Claim 24 words
A method as set forth in claim 1 wherein the reaction between the mercaptoalcohol and the organotin compound is conducted in an aqueous medium.
Claim 9
Dependent Claim 47 words
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.
Claim 10
Dependent Claim 46 words
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.
Claim 11
Independent Claim 247 words
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.
Claim 12
Independent Claim 247 words
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.
Claim 13
Dependent Claim 29 words
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.
Claim 14
Dependent Claim 12 words
A method as set forth in claim 11 wherein R is butyl.
Claim 15
Dependent Claim 18 words
A method as set forth in claim 10 wherein said carboxylic acid is caprylic acid or pelargonic acid.
Claim 16
Dependent Claim 12 words
A method as set forth in claim 10 wherein m is 2.
Claim 17
Dependent Claim 12 words
A method as set forth in claim 10 wherein X is chlorine.
Claim 18
Dependent Claim 19 words
A method as set forth in claim 10 wherein the base reacted with the organotin halide is ammonium hydroxide.
Claim 19
Dependent Claim 17 words
A method as set forth in claim 10 wherein R" contains from 1 to 4 carbon atoms.

References Cited (Backward Citations)

US2832750A Cited
US2870182A Cited
US2885415A Cited
US3931263A Cited
US3979359A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-07-31 1982-01-30 1982-08-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-07-31 1986-01-30 1986-08-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-07-31 1990-01-30 1990-08-01 $7700.00 Window Closed / Lapsed

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