Stauffer Chemical Company

Kyung S Shim

Edward N Walsh

Milton L Honig

Mervin E Brokke

Arthur D Toy

Fred Jaffe

James B Heather

Adam E Skrzec

Polychlorinated polyphenyl materials are reacted with sulfur in the presence of an effective amount of a sulfur chloride compound to result in a product having a lowered residue of chlorinated polyphenyl as compared to a reaction practiced without the use of the compound.

Reaction of sulfur with polychlorinated polyphenyls

There is disclosed a method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting the aromatic or N-heteroaromatic compound with a phenylphosphonous dichloride, phosphorus trichloride and chlorine.

Method for converting carboxylic acid groups to trichloromethyl groups

Lubricating sealants which are resistant to aprotic solvents such as chloroform and carbon disulfide are prepared by forming a grease comprising glycerine, fumed silica, polyethylene glycol and a minor amount of water.

Lubricating sealants

A novel process for the preparation of insoluble sulfur product comprises the steps of vaporizing sulfur, mixing the vaporized sulfur with from about 1.times.10.sup.-6 % to about 5% hydrogen sulfide, in the essential absence of hydrocarbon oil, quenching the vaporized sulfur in a quenching medium and separating the insoluble sulfur product from the quenching medium.

Process for the production of insoluble sulfur

Novel phosphoramides of the formula: ##STR1## wherein: n is 3 to 8;

Novel phosphoramides, lubricating compositions and method of improving

A process for the production of a mono-halothiophenol, e.g. para-chlorothiophenol, and thiophenol. The process comprises reacting a reactant mixture of benzene and dihalobenzene, e.g. para-dichlorobenzene, with hydrogen sulfide in the presence of an absorptive catalyst, such as activated carbon, calcined petroleum coke, etc.

Process for the production of mono-halothiophenols and thiophenols

Thiophenols are produced by reacting the corresponding benzene compound with hydrogen sulfide in contact with an absorptive catalyst, such as activated carbon, calcined petroleum coke, etc. Temperatures in the range of from about 500.degree. to 900.degree. C. are employed.

Process for preparing thiophenols

Phenyl phosphonous dihalide is oxidized according to the following reaction: ##STR1## wherein X is Cl or Br. The reaction is conducted at a temperature from about 0.degree. C. to about 200.degree. C. Charcoal is added to the reaction mixture when impure phenyl phosphonous dihalide is used as a starting material. The product has high purity and is stable at high temperatures. It can be used as an intermediate to prepare flame retardants, insecticides, pesticides and plasticisers.

Oxidation of phenyl phosphonous dihalide

Polyalkylene glycol alkyl or haloalkyl polyphosphonates having the idealized formula: ##STR1## wherein R is a polyalkylene glycol residue, R' is alkyl or haloalkyl and n is 1-100, are prepared by transesterifying a tertiary phosphite with a polyalkylene glycol and rearranging the resultant polyalkylene glycol alkyl or haloalkyl polyphosphite to a polyalkylene glycol alkyl or haloalkyl phosphonate by the action of heat and an Arbuzov rearrangement catalyst.

Process for preparing polyalkylene glycol alkyl or haloalkyl

Mixed polyalkylene glycol polyphosphorus compounds containing both phosphite and vinyl phosphate linkages are prepared by reacting certain polyalkylene glycol polyphosphites with less than a stoichiometric amount of a halogenated carbonyl compound.

Polyurethane foams prepared from mixed polyalkylene glycol

The neutralization of products which are phosphorus containing oligomers having ##STR1## linkages between phosphorus atoms and which are obtained by the self-condensation of .beta.-halo-alkyl esters of pentavalent phosphorus acids or by the condensation of these esters with an alkyl ester of a pentavalent phosphorus acid is accomplished by reaction with an alkylene oxide, either alone or in combination with water or an alcohol having the formula ROH where R is a C.sub.1 -C.sub.20 alkyl group, and is enhanced by heating the products with a Lewis acid to promote alcoholysis reactions between labile groups contained therein and structures formed by alkylene oxide neutralization of free acid groups. The stabilized product formed by this process gives a better cure when incorporated in a polyurethane foam.

Method of preparing stable condensation products using a Lewis acid

Polyalkylene glycol vinyl phosphates having the formula: ##EQU1## WHERE R is a polyalkylene glycol residue, n is an integer from 1 to about 100, R' is either hydrogen, alkyl or haloalkyl, and Z and Y are each either halogen, hydrogen or alkyl are produced by transesterifying a tertiary phosphite with a polyalkylene glycol and reacting the product thereof with a carbonyl compound.

Polyalkylene glycol vinyl phosphates

Polyalkylene glycol alkyl or haloalkyl polyphosphonates having the idealized formula: ##EQU1## WHEREIN R is a polyalkylene glycol residue, R' is alkyl or haloalkyl and n is 1-100, are prepared by transesterifying a tertiary phosphite with a polyalkylene glycol and rearranging the resultant polyalkylene glycol alkyl or haloalkyl polyphosphite to a polyalkylene glycol alkyl or haloalkyl phosphonate by the action of heat and an Arbuzov rearrangement catalyst.

Polyalkylene glycol alkyl or haloalkyl polyphosphonates used as flame

Di-polyoxyalkylene hydroxymethylphosphonate is prepared by contacting phosphorous acid and formaldehyde, or a formaldehyde polymer such as trioxane or paraformaldehyde, preferably in an aqueous medium, to yield a hydroxymethylphosphonic acid intermediate. The intermediate is then contacted wiyth an alkylene oxide selected from ethylene oxide, propylene oxide or butylene oxide to yield di-polyoxyalkylene hydroxymethylphosphonate having the structureal formula: ##EQU1## wherein R is CH.sub.2, ##EQU2## n + m = 2-10. Di-polyoxyalkylene hydroxymethylphosphonate is utilized as a flame retardant, a stabilizer for polyester film and as a plasticizer for cellulose acetate and polyvinyl acetate, among others.

Process of synthesizing di-polyoxylalkylene hydroxymethylphosphonate

Novel cyclic phosphorus esters are disclosed having the formula: ##EQU1## where R.sub.9 and R.sub.10 can be the same or different and are selected from the group consisting of hydrogen, lower alkyl, lower hydroxyalkyl, lower haloalkyl and hydroxy with the proviso that no more than one of R.sub.9 and R.sub.10 can be hydroxy. These compounds are useful for the preparation of flame retardant textile finishes as well as for use as polyols for preparing flame retardant polyurethane foams.

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Irvington, NY, United States of America

Kyung S Shim