The Chemours Company Fc, LLC

E.i. Dupont De Nemours and Company

Compact Membrane Systems, Inc.

Other

Robert Daniel Lousenberg

Mario Joseph Nappa

Konstantinos Kontomaris

Andrew Jackson

Joan Ellen Bartelt

Viacheslav Alexandrovich Petrov

Sudipto Majumdar

Kenneth Evan Loprete

Andrew Edward Feiring

Sheng Peng

Molly S Shoichet

Ning Shangguan

Jonathan Pearce Stehman

Joseph P Stehman

An alkoxyvinyl ether is disclosed having the chemical structure RC(OR)═CHR', wherein Ris an at least partially fluorinated functional group having at least one carbon atom, R′ is an at least partially fluorinated functional group having at least two carbon atoms, and R is a functional group. A method for preparing an alkoxyvinyl ether is disclosed, comprising RCFHCFHR′+KOH/ROH→RC(OR)═CHR′, wherein Ris a perfluoro functional group, R′ is a perfluoro functional group, and R is an alkyl functional group. Another method for preparing an alkoxyvinyl ether is disclosed, comprising RCF═CHR′+KOH/ROH→RC(OR)═CHR′, wherein Ris a perfluoro functional group, R′ is a perfluoro functional group, and R is an alkyl functional group.

Fluorinated alkoxyvinyl ethers and methods for preparing fluorinated alkoxyvinyl ethers

Novel copolymers that are fluoropolymers including a first repeat unit that is fluorinated and cyclic and a second repeat unit from a trifluorovinyl methylene ether monomer having sulfur or sulfone functionality in the pendant group are disclosed. The copolymers have relatively high gas permeability as a result of a cyclic repeat unit in the copolymer backbone and ionomers from oxidation of the sulfur containing functionality are particularity useful in the cathode structure of a proton exchange membrane fuel cell.

Gas permeable fluoropolymers and ionomers

Disclosed herein is a process comprising contacting a haloalkane reactant with an olefin in the presence of a catalyst system that consists of metallic iron and a phosphine to produce a haloalkane insertion product, wherein said haloalkane reactant is an alkane substituted with at least one halogen selected from the group consisting of F, Cl, and combinations thereof. Also disclosed herein is a process comprising contacting CFCClwith CH&#x2550;CHX in the presence of a catalyst system that consists of metallic iron and a phosphine to make CFCClCHCHClX, wherein X&#x2550;F or Cl. Also disclosed are further reactions in a sequence to produce HFO-1336ze and HCFO-1335zd. Also disclosed herein is a new composition comprising the compound CFCFCH&#x2550;CHCl.

Process for producing halogenated olefins

An alkoxyvinyl ether is disclosed having the chemical structure RC(OR)&#x2550;CHR', wherein Ris an at least partially fluorinated functional group having at least one carbon atom, R&#x2032; is an at least partially fluorinated functional group having at least two carbon atoms, and R is a functional group. A method for preparing an alkoxyvinyl ether is disclosed, comprising RCFHCFHR&#x2032;+KOH/ROH&#x2192;RC(OR)&#x2550;CHR&#x2032;, wherein Ris a perfluoro functional group, R&#x2032; is a perfluoro functional group, and R is an alkyl functional group. Another method for preparing an alkoxyvinyl ether is disclosed, comprising RCF&#x2550;CHR&#x2032;+KOH/ROH&#x2192;RC(OR)&#x2550;CHR&#x2032;, wherein Ris a perfluoro functional group, R&#x2032; is a perfluoro functional group, and R is an alkyl functional group.

This invention discloses a method for separation of an aromatic compound from a mixture comprising an alkane using an improved thin-film composite membrane. The membrane is particularly useful for separation of benzene from cyclohexane, which have similar boiling points. The membrane comprises a more mechanically durable and defect-free separation layer as a result of its fabrication from an ionomer solution that is substantially free of dissolved ionic species not associated with the ionomer.

Processes for separation of aromatic compounds using a thin film composite membrane

Separation of linear and branched alkane isomers via selective permeation through a composite membrane is disclosed. The separation layer in the composite membrane is fabricated from a blend of at least two different fluoropolymer compositions, A and B, in which composition A has a normal-alkane isomer permeability that is greater than composition B. Composition B has a normal alkane to branched-alkane isomer selectivity that is equal or greater than composition A. The separation layer in the composite membrane has a normal-alkane permeability that is greater than composition B and a normal-alkane to branched alkane isomer selectivity that is greater than composition A.

Isomer separation with highly fluorinated polymer membranes

A method is provided for converting heat from a heat source to mechanical energy. The method comprises heating a working fluid using heat supplied from the heat source; and expanding the heated working fluid to lower pressure of the working fluid and generating mechanical energy as the pressure of the working fluid is lowered. The method is characterized by using a working fluid comprising (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene (HFO-153-10mzzy). Also provided is a power cycle apparatus. The apparatus is characterized by containing a working fluid comprising HFO-153-10mzzy.

Use of (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene in power cycles

A method for producing heating in a high temperature heat pump having a heat exchanger is provided. The method comprises extracting heat from a working fluid, thereby producing a cooled working fluid wherein said working fluid comprises (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene ('HFO-153-10mzzy'). Also, a high temperature heat pump apparatus is provided containing a working fluid comprising HFO-153-10mzzy. Also a composition is provided comprising (i) a working fluid consisting essentially of HFO-153-10mzzy; and (ii) a stabilizer to prevent degradation at temperatures of 55&#xb0; C. or above, or (iii) a lubricant suitable for use at 55&#xb0; C. or above, or both (ii) and (iii).

Use of (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl) pent-2-ene in high temperature heat pumps

This invention discloses an improved thin-film composite membrane and processes that use the membrane for the separation of gaseous mixtures that include an alkene. The membrane is particularly useful for separation of alkenes from alkanes or the separation of alkenes from other non-hydrocarbon gases. The membrane has a more mechanically durable and defect-free gas-separation layer that is fabricated from an ionomer solution that is substantially free of dissolved ionic species not associated with the ionomer and the mean helium permeability of the thin-film composite membrane is less than two times greater than the intrinsic helium permeability of the gas-separation layer.

Thin-film composite membrane and processes for the separation of alkenes from a gaseous feed mixture

Use of (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene in high temperature heat pumps

Disclosed herein is a method for producing heating in a high temperature heat pump having a heat exchanger. The method comprises extracting heat from a working fluid, thereby producing a cooled working fluid wherein said working fluid comprises at least one alkyl perfluoroalkene ether. Also disclosed is a method of raising the maximum feasible condenser operating temperature in a high temperature heat pump apparatus. The method comprises charging the high temperature heat pump with a working fluid comprising at least one alkyl perfluoroalkene ether. Also disclosed is a high temperature heat pump apparatus. The apparatus contains a working fluid comprising at least one alkyl perfluoroalkene ether. Also disclosed is a composition comprising at least one alkyl perfluoroalkene ether, and specialized additives or lubricants for use in a high temperature heat pump.

Use of alkyl perfluoroalkene ethers and mixtures thereof in high temperature heat pumps

Disclosed are processes for reacting a perfluorinated olefin with an alcohol, an alkali metal hydroxide, and water in the presence of a phase transfer catalyst to form a reaction product mixture that separates into an aqueous phase and an organic phase. Alcohol may be present in an effective amount sufficient to form a third phase comprising at least 50% of the phase transfer catalyst. The third phase can be separated from the organic phase. Also disclosed are methods for recovering and recycling the phase transfer catalyst used in the reaction.

Processes for separating components in alkyl perfluoroalkene ether production

Disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising contacting 1,1,1,3,tetrachloropropane in the vapor phase in a reaction zone with a catalyst comprising iron, to produce a product mixture comprising 1,1,3-trichloro-1-propene; and recovering said 1,1,3-trichloro-1-propene from the product mixture produced. Also disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising heating 1,1,1,3-tetrachloropropane in the liquid phase to produce a mixture comprising 1,1,3-trichloro-1-propene, cooling said mixture, separating hydrogen chloride from said mixture and recovering 1,1,3-trichloro-1-propene.

Synthesis of 1,1,3-trichloro-1-propene

Disclosed are methods of transferring heat comprising providing a device, using a heat-transfer fluid to transfer heat to or from the device, wherein the heat-transfer fluid compositions comprise at least one unsaturated fluoroether having the formula CF(CF)CF&#x2550;CFCF(OR)(CF)CF, CF(CF)C(OR)&#x2550;CFCF(CF)CF, CFCF&#x2550;CFCF(OR)(CF)(CF)CF, CF(CF)CF&#x2550;C(OR)CF(CF)CF, or mixtures thereof, wherein R can be either CH, CHor mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3.

Growing community of inventors

Wilmington, DE, United States of America

Robert Daniel Lousenberg