E.i. Dupont De Nemours and Company

Paul R Resnick

Ming-Hong Hung

David C England

Leo E Manzer

Charles J Molnar

Walther G Grot

Steven Henry Swearingen

Burton C Anderson

Scott Christopher Jackson

Raimund H Silva

Roger A Smith

Carl G Krespan

William H Manogue

James L Webster

Jan J Lerou

Douglas W Bruhnke

Elrey L McCann

Keith W Palmer

Edward H Price

Allen Capron Sievert

Viacheslav Alexandrovich Petrov

Andrew Edward Feiring

Robert Clayton Wheland

William Brown Farnham

Douglas Robert Anton

Weiming Qiu

Bruce E Smart

Ronald James McKinney

Richard E Fernandez

Swiatoslaw Trofimenko

James Arthur Trainham

Thomas C Bissot

Theodore Arthur Treat

Victor Filippovich Cherstkov

Cristobal Bonifaz

Terry M Copeland

Nina Ivanovna Delyagina

Walter G Grot

A process is disclosed for producing 1,1,1,3,3,3-hexafluoropropane and/or 1,1,1,3,3-pentafluoropropene from (CF.sub.3).sub.2 CHCOOH and/or its water soluble salts. The process involves providing a mixture containing water and such carboxy compound(s) which has a pH of less than about 4, and reacting the mixture at a temperature of at least about 75.degree. C. Certain ether compounds may be included in the mixture along with (CF.sub.3)2 CHCOOH and/or its water soluble salts. The reaction of the carboxy (and optionally ether) compound(s) with water may be employed in connection with a process for producing tetrafluoroethylene and/or hexafluoropropylene by pyrolysis, where by-product perfluoroisobutylene is reacted with water (and optionally an alkanol) to produce (CF.sub.3).sub.2 CHCOOH (and optionally one or more ether compounds).

Producing CF.sub.3 CH.sub.2 CF.sub.3 and/or CF.sub.3 CH.dbd.CF.sub.2 by

A process is disclosed for producing a 2,2-bis-substituted-trans-4,5-dichloro-4,5-difluorodioxolane of the formula ##STR1## wherein R.sub.f is selected from the group consisting of --R.sup.2.sub.f, --F, --C(O)F, --C(O)OR and R.sup.3.sub.f Q, and wherein R.sup.1.sub.f is selected from the group consisting of --F and --R.sup.2.sub.f ; wherein R.sup.2.sub.f is a perfluorinated linear or branched alkyl group having 1 to 14 carbon atoms, optionally containing ether oxygen, which is terminally substituted with --F, --Cl, --Br, --OR, --OC.sub.6 F.sub.5, --SO.sub.2 F, --N.sub.3, --CN, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --SO.sub.2 Cl, --C(O)Cl or --C(O)F, wherein R is selected from the group consisting of --CH.sub.3, --C.sub.2 H.sub.5 and --CH.sub.2 CF.sub.3, wherein R.sup.3.sub.f is a single bond or a perfluoroalkylene group having from 1 to 4 carbon atoms optionally containing ether oxygen, and wherein Q is ##STR2## by isomerizing a 2,2-bis-substituted-cis-4,5-dichloro-4,5-difluorodioxolane of the same formula in the presence of a catalyst of the formula AlZ.sub.3, where Z is F, Cl, and/or Br, provided that AlZ.sub.3 is not entirely AlF.sub.3. Also disclosed is a process for producing an olefinic monomer by dechlorinating the trans-isomer products produced by said isomerization.

Monomer precursor isomerization

A process is disclosed for producing CF.sub.3 CH.sub.2 CF.sub.3 and/or CF.sub.3 CH.dbd.CF.sub.2 from at least one ether compound selected from the group consisting of compounds having the formula (CF.sub.3).sub.2 CHCF.sub.2 OR and compounds having the formula (CF.sub.3).sub.2 C.dbd.CFOR (wherein R is an alkyl group of the formula C.sub.n H.sub.2n+1 and n is an integer from 1 to 6) by contacting the ether compound(s) with water at an elevated temperature of at least about 75.degree. C. The reaction of ether compound(s) with water may be employed in connection with a process for producing tetrafluoroethylene and/or hexafluoropropylene by pyrolysis, where by-product perfluoroisobutylene is reacted with an alkanol to produce the ether compound(s).

Producing CF.sub.3 CH.sub.2 CF.sub.3 and/or CF.sub.3 CH=CF.sub.2 by the

Aryl halide, such as idodobenzene, is reacted with perfluoromethoxycarboxylate, such as CF.sub.3 OCF.sub.2 CO.sub.2 K, in the presence of CuI and an inert aprotic polar solvent to obtain trifluoromethylaryl.

Trifluoromethylation process

A process is disclosed for producing CF.sub.3 CH.sub.2 CF.sub.3 and/or CF.sub.3 CH.dbd.CF.sub.2 from at least one ether compound selected from the group consisting of compounds having the formula (CF.sub.3).sub.2 CHCF.sub.2 OR and compounds having the formula (CF.sub.3).sub.2 C.dbd.CFOR (wherein R is an alkyl group of the formula C.sub.n H.sub.2n+1 and n is an integer from 1 to 6) by contacting the ether compound(s) with water at an elevated temperature of at least about 75.degree. C. The reaction of ether compound(s) with water may be employed in connection with a process for producing tetrafluoroethylene and/or hexafluoropropylene by pyrolysis, where by-product perfluoroisobutylene is reacted with an alkanol to produce the ether compound (s).

Production CF.sub.3 CH.sub.2 CF.sub.3 and/or CF.sub.3 CH.dbd.CF.sub.2 by

A process for the manufacture of pentafluorodimethyl ether is disclosed which involves contacting at least one starting compound selected from the group consisting of compounds having a formula (CF.sub.3 OCF.sub.2 CO.sub.2)A and compounds having he formula (CF.sub.3 OCF.sub.2 CO.sub.2).sub.2 A' wherein A is selected from the group consisting of hydrogen, ammonium, alkali metals (e.g., sodium or potassium) and R (wherein R is a C.sub.1 to C.sub.4 alkyl group) and A' is an selected from the group consisting of alkaline-earth metals (e.g., magnesium or calcium), with at least one hydroxylic compound selected from the group consisting of water, mono-alcohols of the formula R'OH (wherein R' is a C.sub.1 to C.sub.12 straight or branched chain alkyl group) and alkanediols of the formula R' (OH).sub.2 (wherein R' is a C.sub.2 to C.sub.8 alkylene group) at temperature of about 120.degree. C. to 170.degree. C.

Process for the production of pentaflourodimethyl ether

The comonomers are perfluorocyclic unsaturated compounds, copolymerized to form amorphous copolymer. Such copolymer forms optically clear tough coating and films.

Copolymers of perhalo-2,2-di-loweralkyl-1,3-dioxole, and

Repeat units having pendant functional groups increase the solubility of polymers containing repeat units of perfluoro-2,2-dimethyl-1,3-dioxole.

Functional fluoropolymers

An optical fiber cladding made of copolymers of perfluoro( 1,3 -dimethyl-2,2-dioxole) with perfluoro(butenyl vinyl ether) and, optionally, with a third comonmer are amorphous in all monomer proportions, and soluble in perfluoro(2-butyl tetrahydrofuran). Dipolymers of the present invention have lower glass transition temperatures than dipolymers of perfluoro(1,3-dimethyl-2,2-dioxole) with tetrafluoroethylene having the same monomer proportions.

Optical fiber comprising a cladding made of amorphous copolymers of two

Copolymers of perfluoro(1,3-dimethyl-2,2-dioxole) with perfluoro(butenyl vinyl ether) and, optionally, with a third comonomer are amorphous in all monomer proportions, and soluble in perfluoro(2-butyl tetrahydrofuran). These copolymers are suitable in many high technology applications, especially where solubility is important, e.g., in applying coatings to substrates or articles for protection against mechanical, chemical, or environmental hazards. Dipolymers of the present invention have lower glass transition temperatures than dipolymers of perfluoro(1,3-dimethyl-2,2-dioxole) with tetrafluoroethylene having the same monomer proportions.

Amorphous copolymers of two fluorinated ring monomers

This invention is directed to halodihydrodioxins, their preparation and their polymers, which provide amorphous homopolymers that are resistant to ring opening side reactions. The resulting polymers can be used for films and thermally stable molded objects, coatings for substrates such as wood, glass, paper and metal and for protective packaging. This invention also concerns the preparation of polyhalogenated dioxoles.

Polyhalodihydrodioxins and polyhalodioxoles

Copolymers of perfluoro(1,3-dimethyl-2,2-dioxole) with perfluoro(butenyl vinyl ether) and, optionally, with a third comonmer are amorphous in all monomer proportions, and soluble in perfluoro(2-butyl tetrahydrofuran). These copolymers are suitable in many high technology applications, especially where solubility is important, e.g., in applying coatings to substrates or articles for protection against mechanical, chemical, or environmental hazards. Dipolymers of the present invention have lower glass transition temperatures than dipolymers of perfluoro(1,3-dimethyl-2,2-dioxole) with tetrafluoroethylene having the same monomer proportions.

Partially fluorinated compounds of specified formulas that are useful as chemical intermediates and monomers are disclosed. Partially fluorinated polymers prepared from one of these compounds are also disclosed. Fluoro-2,2-dimethyldioxolanes and copolymers thereof are further disclosed.

Growing community of inventors

Wilmington, DE, United States of America

Paul R Resnick