Stauffer Chemical Company

Ici Americas, Inc.

Akzo America Inc.

Peter E Timony

Andrea Leone-Bay

Elliott Bay

Edward D Weil

John Tomko

Theodore A Marolewski

George Berens

Frank L Padovani

Laurel Glaser

A process for chlorinating compounds containing a carbon atom bonded to a hetero-atom selected from the group consisting of oxygen, nitrogen and sulfur; said process comprises contacting the carbon hetero-atom containing compound with a chloro phosphorus complex of the formula

Processes using a phosphorus complex

N-succinimidyl haloacetyl aminobenzoates are formed by: (a) reacting an aminobenzoic acid with haloacetylhalide to form a haloacetylaminobenzoic acid; (b) optionally converting the haloacetylaminobenzoic acid from (a) to the ultimately desired halo intermediate compound; (c) reacting the compound from (b) with oxalyl halide to form the corresponding benzoyl compound; and (d) coupling the benzoyl compound from (c) with an N-hydroxysuccinimide to form the ultimately desired N-succinimidyl haloacetyl aminobenzoate.

Synthesis of N-succinimidyl haloacetyl aminobenzoates

A process for selectively substituting an aromatic nitro group of a nitrophthalic anhydride with a halo group which comprises contacting the nitroaromatic-containing compound with a phosphorus halide of formula:

Preparation of halophthalic anhydrides

A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C. to about 150.degree. C. for from about 1 hour to about 24 hours is preferred.

Process for converting organo-hydroxyl compounds to halides

A process for selectively substituting an aromatic nitro group with a halo group which comprises contacting the nitroaromatic compound with a phosphorushalide of formula: R.sub.n PX.sub.5-n wherein n is selected from 0, 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of: straight and branched chain alkyl, alkoxy, and haloalkyl; halogen, sulfonate and mixtures thereof; and X is a halogen in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphosphorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture to maintain a temperature of from about 100.degree. C. to about 175.degree. C. for from about 1 hour to about 24 hours.

Preparation of aryl halides

Liquid para-toluenesulfonyl chloride is reacted with chlorine gas at elevated temperatures in the presence of a catalytic amount of a Lewis acid catalyst, preferably antimony trichloride. Sulfuric acid is added then the reaction mixture is heated and subsequently cooled to about room temperature. Ammonium hydroxide is added then the reaction mixture is distilled to yield a substantially pure 2,6-dichlorotoluene.

Process for preparing 2,6-dichlorotoluene

Herbicidal compounds having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl; C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms; and Y is benzyl or mono-substituted benzyl wherein the substituent is halogen, amino, nitro or C.sub.1 -C.sub.4 haloalkyl.

Herbicidal esters of 2-bromo-4-methylimidazole-5-carboxylic acid

An herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl; C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms, C.sub.2 -C.sub.10 alkenyl, C.sub.5 -C.sub.8 cycloalkenyl; benzyl or mono- or di-substituted benzyl wherein the substituents are C.sub.1 -C.sub.4 alkyl, halogen, nitro or C.sub.1 -C.sub.4 haloalkyl and Y is substituted or unsubstituted pyridyl or benzimidazoyl.

An herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl; C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms, C.sub.2 -C.sub.10 alkenyl, C.sub.5 -C.sub.8 cycloalkenyl; benzyl or mono- or di-substituted benzyl wherein the substituents are C.sub.1 -C.sub.4 alkyl, halogen, nitro or C.sub.1 -C.sub.4 haloalkyl and Y is substituted or unsubstituted phenyl.

A herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl and Y is C.sub.1 -C.sub.10 alkyl optionally substituted with halogen or N-(R').sub.2 where R' is C.sub.1 -C.sub.10 alkyl.

Herbicidal esters of N-substituted

A herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl; X is oxygen, sulfur, sulfoxide or sulfone; and Y is C.sub.1 -C.sub.6 alkyl, phenyl or substituted phenyl.

A herbicidal compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.10 alkyl; C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms, C.sub.2 -C.sub.10 alkenyl, C.sub.5 -C.sub.8 cycloalkenyl; benzyl or mono- or di-substituted benzyl wherein the substituents are C.sub.1 -C.sub.4 alkyl, halogen, nitro or C.sub.1 -C.sub.4 haloalkyl and Y is substituted or unsubstituted C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkylthio, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 alkenylthio, aryloxy (thio) arylalkoxy.

A herbicidal compound having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms, C.sub.3 -C.sub.10 alkenyl, C.sub.5 -C.sub.8 cycloalkenyl; benzyl or mono- or di-substituted benzyl wherein the substituents are C.sub.1 -C.sub.4 alkyl, halogen, nitro or C.sub.1 -C.sub.4 haloalkyl; R.sup.1 and R.sup.2 independently are C.sub.1 -C.sub.6 alkyl or aryl, or R.sup.1 and R.sup.2 together form a ring with the nitrogen to which they are attached having 3-8 carbon atoms, optionally substituted with one or two methyl groups.

A herbicidal compound having the structural formula ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted phenyl; substituted or unsubstituted benzyl, preferably hydrogen or methyl; and R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, preferably hydrogen or methyl.

Herbicidal hydroxyamides of 2-bromo-4-methylimidazole-5-carboxylic acid

An electric contact lubricant is disclosed which comprises a partially crosslinked polyol ester formed by esterification of an aliphatic monocarboxylic acid with an aliphatic polyol in the presence of a dibasic acid crosslinker, a phosphate ester fluid, and one or more corrosion and oxidation inhibitor compounds.

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Valley Cottage, NY, United States of America

Peter E Timony