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Process for the production of sulfenamides
| Details |
Inventors: Cobb, Alec S.; Williams, David J.;
Assignee: Monsanto Europe S.A. (Brussels, BE)
Primary Examiner: Daus; Donald G.
Assistant Examiner: Springer; D. B.
Attorney, Agent or Firm: Seward; Gordon B.
Benzothiazole-2-sulfenamides are prepared by reacting a 2-mercaptobenzothiazole and a primary or secondary amine with oxygen in the presence of a catalyst, for example a metal phthalocyanine, in a reaction medium consisting of (i) a mixture of the amine and water in which the amount of water at the outset of the reaction is from 0.2 to 20% by weight of the mixture, or (ii) a mixture as defined in (i) diluted with an inert organic solvent miscible with the mixture, in a proportion of up to two parts by weight of the inert organic solvent per part by weight of the mixture. |
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DETAILED DESCRIPTION The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows: 1.
In a process for the production of a sulfenamide, in which a 2-mercaptobenzothiazole of the formula ##STR6## where each of R.
sup.
1, R.
sup.
2, R.
sup.
3, and R.
sup.
4 is independently hydrogen, C.
sub.
1-6 alkyl, C.
sub.
1-6 alkoxy, chloro- or other inert substituent, and an amine which is a primary alkylamine or cycloalkylamine, or a secondary amine having the formula ##STR7## where each of R.
sup.
5 and R.
sup.
6 is hydrogen or an alkyl or cycloalkyl group or where R.
sup.
5 and R.
sup.
6 are linked such that the amine has a saturated ring structure optionally containing a heteroatom in addition to the nitrogen atom shown in the formula, are reacted with oxygen in the presence of a water-insoluble catalyst selected from metal complexes of porphyrazine and its derivatives in a reaction medium consisting essentially of water and a stoichiometric excess of the amine relative to the 2-mercaptobenzothiazole, the improvement which comprises using as the reaction medium a mixture of the amine and water in which the amount of water at the outset of the reaction is from 0.
5 to 5% of the weight of the mixture.
2.
A process according to claim 1 wherein the amount of amine is from 2 to 20 moles per mole of the 2-mercaptobenzothiazole.
3.
A process according to claim 2 wherein the catalyst is a cobalt phthalocyanine.
4.
A process according to claim 2 wherein the catalyst is a manganese phthalocyanine.
5.
A process according to claim 1 wherein the catalyst is adsorbed on a water-insoluble support.
6.
A process according to claim 5 wherein the support is an activated carbon.
7.
A process according to claim 1 wherein each of R.
sup.
1, R.
sup.
2, R.
sup.
3, and R.
sup.
4 in the formula of the 2-mercaptobenzothiazole is hydrogen and the amine is tert-butylamine, isopropylamine, morpholine, cyclohexylamine or diethylamine.
Description:
This invention relates to a process for the production of sulfenamides which are useful as accelerators in the vulcanization of rubber
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