Preparation of bismuth dithiocarbamates
AssigneeR.T. Vanderbilt Company, Inc.
InventorsThomas J. Karol, Steven G. Donnelly
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Abstract
A novel method is disclosed for preparation of bismuth dithiocarbamates by an exchange reaction between a bismuth carboxylate and a metal dithiocarbamate. The metal dithiocarbamate can be added to the reaction or prepared in situ by reacting a secondary amine and carbon disulfide in the presence of metal oxide, metal hydroxide or a tertiary amine. The reaction products are useful as extreme pressure additives when incorporated in lubricants.
Claims8
A method for preparation of reaction mixtures by exchange reaction and comprising bismuth dithiocarbamates of the formula ##STR9## wherein R and R.sup.1 are hydrocarbyl groups selected independently from alkyl, alkenyl, cycloalkyl, aryl, alkaryl and arylalkyl groups and metal carboxylates of the formula ##STR10## wherein M represents a metal selected from alkali metals, group IIA and group IIB metals, n is 1 or 2, and R.sup.2 is an alkyl or alkenyl group, naphthetic radical, or fatty radical having 8 to 22 carbon atoms comprising the steps of
- (1) reacting a secondary amine of the formula ##STR11## wherein R and R.sup.1 represent groups defined above, with carbon disulfide and monovalent or divalent metal hydroxide or oxide to form the corresponding metal dithiocarbamate intermediate,
- (2) adding bismuth carboxylate of the formula ##STR12## wherein R.sup.2 represents the groups defined above, (3) heating at 25.degree. to 120.degree. C. to produce said reaction mixture, wherein the mole ratio of the bismuth dithiocarbamate to the metal carboxylate is about 1:1 to 1.5:1.
A method for preparation of reaction mixtures by an exchange reaction and comprising bismuth dithiocarbamates of the formula ##STR13## wherein R and R.sup.1 are hydrocarbyl groups selected independently from alkyl, alkenyl, cycloalkyl, aryl, alkaryl and arylalkyl groups and compounds of the formulae ##STR14## wherein R.sup.2 is an alkyl or alkenyl group, naphthetic radical, or fatty radical having 8 to 22 carbon atoms comprising the steps of
- (1) reacting a secondary amine of the formula R.sup.1 -NH-R wherein R and R.sup.1 represent groups defined above, with carbon disulfide in a mole ratio of about 2:1 to form the corresponding dithiocarbamate amine salt intermediate,
- (2) adding bismuth carboxylate of the formula ##STR15## wherein R.sup.2 represents the groups as defined above, (3) heating at 25.degree. to 1200.degree. C. to produce a reaction mixture wherein the mole ratio of the bismuth dithiocarbamate of formula (I) and the amine salt of carboxylic acid of formula (II) is about 1:1 to 1.5:1,
- (4) adding one mole of carbon disulfide and one-third mole of bismuth carboxylate of formula IV,
- (5) heating at 25.degree. to 1200.degree. C. to produce a reaction mixture wherein the mole ratio of the bismuth dithiocarbamate of formula (I) and carboxylic acid of formula (II) is about 2:1 to 2.5:1.
A method for preparation of reaction mixtures by an exchange reaction and comprising bismuth dithiocarbamates of the formula ##STR16## wherein R and R.sup.1 are hydrocarbyl groups selected independently from alkyl, alkenyl, cycloalkyl, aryl, alkaryl and arylalkyl groups and amine salts of carboxylates of the formula ##STR17## wherein R.sup.3 represents hydrogen, R or R.sup.1 as defined above, R.sup.4 is alkyl, alkenyl or fatty residue having 8 to 22 carbon atoms, comprising the steps of
- (1) reacting a secondary amine of the formula ##STR18## wherein R and R.sup.1 represent groups defined above, with carbon disulfide and an amine of the formula VII or VIII ##STR19## wherein R, R.sup.1, R.sup.3 and R.sup.4 represent groups defined above, to form the corresponding amine dithiocarbamate intermediate,
- (2) adding bismuth carboxylate of the formula ##STR20## wherein R.sup.2 represents the groups defined above, (3) heating at 25.degree. to 120.degree. C. to produce said reaction mixture wherein the mole ratio of the bismuth dithiocarbamate to the amine carboxylate is about 1:1 to 1.5:1.
Dependencies are inferred from the claim text.