E.i. Dupont De Nemours and Company

Frank J Weigert

V N Rao

Carl G Krespan

Leo E Manzer

Douglas Robert Anton

William H Manogue

Carl S Kellner

Allen Capron Sievert

Leo Ernest Manzer

V N Mallikarjuna Rao

Shlomo Rozen

Thomas W Del Pesco

Jan J Lerou

William C Seidel

Douglas W Bruhnke

A method is disclosed for increasing in a composition the mole fraction of a compound selected from the group CF CHCl , CF CHF and CF CHClF relative to the total mole fraction of the other two compounds of the group. The method comprises (a) providing a gaseous composition comprising at least one compound of said group provided that (i) if the selected compound is either CF CHCl or CF CHF , said gaseous composition comprises CF CHFCl and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 50&deg; C., and (ii) if the selected compound is CF CHFCl, said gaseous composition comprises both CF CHCl and CF CHF and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 500&deg; C.; (b) contacting said gaseous composition with a catalyst selected from the group of catalysts consisting of catalysts comprising chromium as an oxide, as a halide or as a halided oxide, in a valence state of three to six, and supported catalysts containing at least one metal selected from cobalt, copper, iron, manganese, nickel and zinc for a time sufficient to provide substantial equilibrium between the three compounds having said formula; and (c) providing during said catalyst contact a temperature within the range of about 50&deg; C. to 500&deg; C. at which the mole fraction of the selected compound relative to the other two compounds increases.

Catalytic equilibration to increase the relative mole fraction of CF3CHCI, CF3CHCI2 or CF3CF2H in a composition

Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions

Gas phase and liquid phase processes are disclosed which use interconversion of CF.sub.3 CHFCl and CF.sub.2 HCF.sub.2 Cl in contact with catalyst consisting essentially of halided aluminum oxide and/or aluminum halide at elevated temperatures to increase the mole ratio of one of said compounds in a composition relative to the other. Also disclosed is use of said interconversion along with hydrogenolysis in processes for producing mixtures of CF.sub.3 CH.sub.2 F and CF.sub.2 HCF.sub.2 H from certain compositions comprising CF.sub.2 HCF.sub.2 Cl such that the mole ratio of CF.sub.3 CH.sub.2 F to CF.sub.2 HCF.sub.2 H in the product mixtures produced from said compositions may be increased or decreased.

Catalytic equilibration to improve the relative yield of selected

A catalyic process is disclosed for producing CF.sub.3 CHClF from CF.sub.3 CH.sub.2 F by chlorination at elevated temperature. Suitable catalysts for the process include carbon catalysts and catalysts wherein halides of certain metals (La, Zn, Cu, Cr, Ru, Rh, and/or Pt) are supported on carbon.

Catalytic process for producing CF.sub.3 CHClF

A catalyic process is disclosed for producing fluorine-substituted hydrocarbon products of the formulae RCH.sub.2 CF.sub.2 R and RFC.dbd.CHR at an elevated temperature, from compounds of the formula RCHFCHFR, where each R is independently selected from the group consisting of --CF.sub.3, --CF.sub.2 CF.sub.3 and --CF.sub.2 CF.sub.2 CF.sub.3 or where both R groups of a formula together are --(CF.sub.2).sub.2 --, --(CF.sub.2).sub.3 -- or --(CF.sub.2).sub.4 --. Suitable catalysts include carbon catalysts and catalysts containing at least one compound of a selected metal (e.g., Na, K, Rb, Cs, Y, La, Ce, Pr, Nd, Sm, Cr, Fe, Co, Rh, Ni, Cu, and/or Zn) supported on carbon. The saturated gem-dihydro- products may also be produced by hydrofluorinating the corresponding olefinic product over such catalysts at an elevated temperature, and can be combined with various other miscible solvents to form compositions useful for cleaning. Compounds such as CF.sub.3 CF.sub.2 CH.sub.2 CF.sub.2 CF.sub.3, CF.sub.3 CF.sub.2 CH.sub.2 (CF.sub.2).sub.2 CF.sub.3, CF.sub.3 CH.dbd.CF(CF.sub.2).sub.2 CF.sub.3, CF.sub.3 CF=CH(CF.sub.2).sub.2 CF.sub.3, CF.sub.3 CF.sub.2 CH.sub.2 (CF.sub.2).sub.3 CF.sub.3, CF.sub.3 (CF.sub.2).sub.2 CH.sub.2 (CF.sub.2).sub.2 CF.sub.3, CF.sub.3 CH.dbd.CF(CF.sub.2).sub.3 CF.sub.3, CF.sub.3 CF.dbd.CH(CF.sub.2).sub.3 CF.sub.3, CF.sub.3 (CF.sub.2).sub.2 CH.sub.2 (CF.sub.2).sub.3 CF.sub.3, CF.sub.3 CF.sub.2 CH.sub.2 (CF.sub.2).sub.4 CF.sub.3, CF.sub.3 CH.dbd.CF(CF.sub.2).sub.4 CF.sub.3, CF.sub.3 CF=CH(CF.sub.2).sub.4 CF.sub.3, CF.sub.3 CF.sub.2 CH.dbd.CF(CF.sub.2).sub.3 CF.sub.3, CF.sub.3 CF.sub.2 CF=CH(CF.sub.2).sub. 3 CF.sub.3 and ##STR1## and azeotropic compositions such as azeotropes of CF.sub.3 CH.sub.2 CF.sub.2 CF.sub.2 CF.sub.3 and/or CF.sub.3 CF.sub.2 CH.sub.2 CF.sub.2 CF.sub.3 with methanol, ethanol, or isopropanol are disclosed.

Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes

The compound, 1,1,1,2,2,3,3,4,4,5,6-undecafluorohexane, and mixtures thereof with alcohols, ethers, esters, ketones, nitromethane, and halogenated hydrocarbons are disclosed; as is the use thereof for cleaning a solid surface by treating the surface with said compound or said mixtures.

1,1,1,2,2,3,3,4,4,5,6-undecafluorohexane and use thereof in compositions

A process for transfer hydrogenation of nitriles and amines wherein the amines are the hydrogen donors is disclosed.

Transfer hydrogenation of nitriles using amine donors

Mixtures of the compound 1,1,1,2,2,5,5,5-octafluoro-4-trifluoromethylpentane with alcohols, ethers, esters, ketones, nitrogen-containing organic compounds, and halogenated hydrocarbons are disclosed; as is a process for cleaning a solid surface which comprises treating the surface with said mixtures. Binary mixtures of 1,1,1,2,2,5,5,5-octafluoro-4-trifluoromethylpentane with about 5 to 13 weight percent methanol, with about 2 to 10 weight percent ethanol, with about 3 to 11 weight percent isopropanol, with about 50 to 58 weight percent dichloromethane, and with about 1 to 9 weight percent acetonitrile, are disclosed as azeotrope or azeotrope-like compositions and are particularly suited for use where solvent recovery and reuse is practiced.

Compositions of 1,1,1,2,2,5,5,5,-octafluoro-4-trifluoromethylpentane and

The catalytic pyrolysis of bis(hexamethylene)-triamine in a slurry or fixed bed reaction yields hexamethyleneimine, hexamethylenediamine and N-(6-aminohexyl)hexamethyleneimine.

Process for the catalytic pyrolysis of bis(hexamethylene)triamine

A vapor phase process is disclosed for producing HCFC-225s, HCFC-235s, HCFC-226s, HFC-236s, and HFC-227s by reacting certain three-carbon reactants containing at least one less fluorine than, and at least as many hydrogen substituents as the desired product (e.g. propane propylene, allene or methylacetylene) with Cl.sub.2 and HF in the presence of a catalyst consisting essentially of chromium oxide or of chromium oxide which is combined with a refractory oxide, fluorinated and/or modified with manganese, iron, cobalt, nickel, copper and/or zinc. The temperature and contact time for the reaction are chosen to provide a product having the desired fluorine and hydrogen content.

Process for the manufacture of halogen-substituted propanes containing

A process is disclosed for the preparation of methyl- and ethyl-substituted anilines by contacting anilines of specified formula at about 250.degree.-525.degree. C. and about 10 kPa-10 MPa of pressure in the of presence of a nonbasic metal oxide catalyst which when it is a zeolite has pore dimensions of at least about 0.52 nm and has cages with dimensions greater than about 0.75 nm.

Process for preparing methyl- and ethyl-substituted primary anilines

A process for the preparation of chlorofluoropropanes of the formula C.sub.3 HCl.sub.2 F.sub.5 by contacting monofluorodichloromethane with tetrafluoroethylene in the presence of a modified aluminum chloride catalyst at a temperature of 0.degree. to 150.degree. C. The novel compound CF.sub.3 CCl.sub.2 CHF.sub.2 is also disclosed.

Process for chlorofluoropropanes

A process for the hydrogenolysis and/or dehydrohalogenation of fluorohalocarbons and/or fluorohalohydrocarbons by reacting the fluorohalocarbons and/or fluorohalohydrocarbons with a source of hydrogen in the presence of a catalyst, the improvement comprising utilizing a rhenium-containing catalyst, which may, optionally, contain at least one Group VIII metal and may, optionally, be supported.

Hydrogenolysis/dehydrohalogenation process

A catalyic process is disclosed for producing CCl.sub.3 CF.sub.3 from CHCl.sub.2 CF.sub.3, CH.sub.2 ClCF.sub.3 and/or CH.sub.3 CF.sub.3 by chlorination at elevated temperature. Suitable catalysts for the process include carbon catalysts and catalysts wherein halides of certain metals (Zn, Cu, Cr, Ru, Rh, and/or Pt) are supported on carbon.

Growing community of inventors

Wilmington, DE, United States of America

Frank J Weigert