Abstract: This invention relates to a process for producing 1,1,1,2-tetrafluoroethane (HFC-134a). The process reacts, 1,1,1-trifluoro-2-chloroethane (HCFC-133a) and hydrogen fluoride in a first reactor. The product resulting from the first reaction step is brought to a second reactor together with trichloroethylene and hydrogen fluoride. The second reaction is conducted at a higher temperature than the first reactor. Optionally, HCl is removed prior to removal of the crude HFC-134a product. Unreacted HCFC-133a, trichloroethylene and hydrogen fluoride may be recycled back to the first reactor.
Type:
Grant
Filed:
August 18, 1995
Date of Patent:
August 5, 1997
Assignee:
AlliedSignal Inc.
Inventors:
Hsueh Sung Tung, Paul Gene Clemmer, Gustavo Cerri, Yuon Chiu, Stanley Michael Jaskot, Nemesio Rogelio Viso, Addison Miles Smith, Jeffrey Warren McKown, Jay Philip Friedenson
Abstract: A process for the continuous production of telomers CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.n Cl where n=1-3 (Formula I) by the continuous reaction of CCl.sub.4 and vinylidene chloride in the presence of a solvent and a catalyst. The reaction to form CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl proceeds at a reaction rate constant k.sub.1. If n=1, CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl is continuously removed from the reactor. If n=2, the removed CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl reacts similarly with CCl.sub.4 and CH.sub.2 .dbd.CCl.sub.2 in a second reactor to form and remove CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.2 Cl under conditions to have a reaction rate constant k.sub.2, wherein the ratio of the molar amounts of CCl.sub.4 to CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl reacted is greater than the ratio k.sub.2 /k.sub.1. If n=3, the removed CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.2 Cl similarly reacts in a third reactor with CCl.sub.4 and CH.sub.2 .dbd.CCl.sub.2 to form CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.
Type:
Grant
Filed:
August 8, 1995
Date of Patent:
May 27, 1997
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, Timothy R. Demmin, David E. Bradley
Abstract: A process for producing 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts having the formula ##STR1## wherein the Z substituent is OH, OR, OC(O)R, SO.sub.3, SO.sub.2 R, NO.sub.2, NO, or PO(OR).sub.2, wherein R is an aryl or C.sub.1 -C.sub.8 alkyl group; n is 0, 1 or 2; each of R.sub.1, R.sub.2, R.sub.3, P.sub.4 and R.sub.5 independently represent hydrogen, C.sub.1 to C.sub.8 alkyl, or aryl 1-substituted-1,4-diazoniabicyclo[2.2.2]octane or 1,4-diazoniabicyclo[2.2.2]octane mono-N-oxide is reacted to attach the Z group and then the result is reacted with molecular fluorine in the presence of a solvent that substantially does not react with fluorine and a fluoride scavenger that results in an X counter ion. These compounds are useful as fluorinating agents for the introduction of fluorine into organic compounds.
Type:
Grant
Filed:
May 6, 1996
Date of Patent:
May 20, 1997
Assignee:
AlliedSignal Inc.
Inventors:
Andrew J. Poss, George A. Shia, Dennis M. Lavery
Abstract: A vapor phase process for the preparation of fluorinated ketones, such as 1,1,1,3,3,3-hexafluoro-2-propanone via oxidation of hydrofluorocarbons, such as 1,1,1,3,3,3-hexafluoropropane, with an oxidizing agent and elemental fluorine at temperatures ranging from 50.degree. C. to 300.degree. C. and residence times ranging from 2 to 60 seconds.
Type:
Grant
Filed:
July 26, 1996
Date of Patent:
May 13, 1997
Assignee:
AlliedSignal Inc.
Inventors:
Alagappan Thenappan, Michael Van Der Puv, Richard Eibeck
Abstract: A vapor phase process for producing a fluorinated alcohol, such as 2,2,2-trifluoroethanol via oxidation of an hydrofluorocarbon, such as 1,1,1-trifluoroethane, with an oxidizing agent and elemental fluorine.
Type:
Grant
Filed:
July 26, 1996
Date of Patent:
May 13, 1997
Assignee:
AlliedSignal Inc.
Inventors:
Alagappan Thenappan, Michael Van Der Puy, Richard Eibeck
Abstract: Stable azeotrope-like compositions consisting essentially of dichloropentafluoropropane and a hydrocarbon containing six carbon atoms which are useful in a variety of industrial cleaning applications including cold cleaning and defluxing of printed circuit boards.
Type:
Grant
Filed:
February 11, 1992
Date of Patent:
April 8, 1997
Assignee:
AlliedSignal Inc.
Inventors:
Hillel Magid, David P. Wilson, Dennis M. Lavery, Richard M. Hollister, Richard E. Eibeck, Michael Vanderpuy
Abstract: The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.
Abstract: This invention is related to the preparation of hydrofluorocarbons (HFCs). Specifically, it relates to the fluorination of a compound of the formula:CF.sub.y Cl.sub.3-y CH.sub.2 CHF.sub.w Cl.sub.2-wwherein w=0 or 1, and y=0-3, with hydrogen fluoride in the presence of a fluorination catalyst under conditions sufficient to produce a compound of the formula CF.sub.3 CH.sub.2 CF.sub.2 H.CF.sub.3 CH.sub.2 CF.sub.2 H or HFC 245fa may be used as a blowing agent, a propellant, and a heat transfer agent.
Abstract: The present invention relates to foam compositions which are expanded with hydrohalocarbon blowing agents in the presence of catalysts which are capable of decreasing the amount of decomposition of the hydrohalocarbon blowing agents to haloalkenes during the polymerization. Thus, the present invention provides compositions comprising polyisocyanate, polyol, hydrohalocarbon blowing agent, surfactant, and catalyst for polymerization of the polyisocyanate and polyol wherein the catalyst is capable of decreasing the amount of decomposition of the hydrohalocarbon blowing agents to haloalkenes during polymerization of the polyisocyanate and the polyol.
Type:
Grant
Filed:
November 23, 1994
Date of Patent:
October 1, 1996
Assignee:
AlliedSignal, Inc.
Inventors:
Timothy R. Demmin, Robert C. Parker, Richard E. Eibeck, Gary M. Knopeck, Donna M. Ruszaj
Abstract: (8S)-8-fluoroerythromycins are prepared by reacting 8,9-anhydroerythromycin 6,9-hemiacetals or an N-oxide thereof with a carboxylic acid and an N-F fluorinating agent. The anhydro starting material may be prepared in situ from erythromycins or an N-oxide derivative thereof. The (8S)-8-fluoroerythromycin products are useful antibacterial agents.
Abstract: A process for the preparation of one or more of CHClFCF.sub.3 (HCFC-124), CHF.sub.2 CClF.sub.2 (HCFC-124a) and CHF.sub.2 CF.sub.3 (HFC-125) by reaction of perchloroethylene with hydrogen fluoride in a single stage reaction vessel in the presence of a fluorination catalyst. These compounds are useful in a variety of industrial applications including blowing agents, refrigerants, sterilant gases and solvent applications. Distilling the reaction product produces a distillate comprising HCl, CHClFCF.sub.3, CHF.sub.2 CClF.sub.2 and CHF.sub.2 CF.sub.3 and a minor amount of HF which distillate is scrubbed to remove the acids. The bottoms product comprises perchloroethylene, hydrogen fluoride and organic by-products which is phase separated to sequester the hydrogen fluoride from the mixture of perchloroethylene and organic by-products. The hydrogen fluoride and mixture of perchloroethylene with organic by-products are then preferably re-mixed at a controlled rate and recycled to the reaction vessel.
Type:
Grant
Filed:
May 25, 1994
Date of Patent:
August 13, 1996
Assignee:
AlliedSignal Inc.
Inventors:
Hsueh S. Tung, Addison M. Smith, Charles F. Swain
Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH.dbd.CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2x+1. The invention is also directed to a practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.
Type:
Grant
Filed:
September 15, 1995
Date of Patent:
July 2, 1996
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
Abstract: A method for converting Explosive D, i.e., ammonium picrate to oxygenated products, particularly hydroquinone or cyclohexanediol and ammonia by hydrogenation over a supported Group VIII metal catalyst. Preferably, the ammonium picrate is dissolved in a suitable solvent and then hydrogenated at a temperature of about 25.degree. to 250.degree. C., and a pressure of about 10 to 1000 psig (69 to 6900 kPa gauge) followed by separation of the commercially valuable products and ammonia.
Type:
Grant
Filed:
December 22, 1994
Date of Patent:
June 25, 1996
Assignee:
AlliedSignal Inc.
Inventors:
Russell W. Johnson, Robert H. Sedath, Mark B. Koch
Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH=CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2.times.+1. The invention is also directed to a lo practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.
Type:
Grant
Filed:
March 28, 1995
Date of Patent:
January 2, 1996
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.
Abstract: SUBSTITUTED-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS AND THEIR APPLICATION AS FLUORINATING AGENTS The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.
Abstract: The present invention provides a process for recovering arsenic acid from a starting mixture comprising sulfuric and arsenic acids and water. In step (a), the starting mixture is treated with a sulfur (IV) compound which will reduce the arsenic acid to arsenic (III) compound under conditions sufficient to substantially convert the arsenic acid to arsenic (III) wherein the resulting mixture comprises arsenic (III) compound, the sulfur (IV) compound, sulfuric acid, and water. In step (b), the resulting mixture is purged with gas to substantially remove the sulfur (IV) compound from the mixture wherein the purged mixture comprises the arsenic (III) compounds, sulfuric acid, and water. In step (c), the purged mixture is treated under conditions sufficient to substantially separate the arsenic (III) compounds from the purged mixture.
Type:
Grant
Filed:
August 26, 1994
Date of Patent:
September 12, 1995
Assignee:
AlliedSignal Inc.
Inventors:
Charles L. Redmon, Somanahalli N. Subbanna, Robert A. Smith
Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH=CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2x+1. The invention is also directed to a practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.
Type:
Grant
Filed:
May 16, 1994
Date of Patent:
August 29, 1995
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
Abstract: A process for the preparation of compounds of the formula, F(CF.sub.2).sub.a CC1.sub.2 CC1.sub.2 (CF.sub.2).sub.b F where a and b are the same or different and are each an integer .gtoreq.1 (including the novel compound CF.sub.3 CF.sub.2 CC1.sub.2 CC1.sub.2 CF.sub.2 CF.sub.3), which comprises chlorination in the presence of irradiation, of at least one compound of the formula, F(CF.sub.2).sub.n CH.sub.x C1.sub.3-x where n is an integer .gtoreq.1 and x is an integer .ltoreq.3. There is also disclosed a process for utilizing the F(CF.sub.2).sub.a CC1.sub.2 CC1.sub.2 (CF.sub.2).sub.b F compounds to produce F(CF.sub.2).sub.a CH.sub.2 CH.sub.2 (CF.sub.2).sub.b F.sub.3 compounds which comprises contacting hydrogen and the F(CF.sub.2).sub.a CC1.sub.2 CC1.sub.2 (CF.sub.2).sub.b F compounds in the presence of a catalysis which includes at least one Group VIII transition metal. A further aspect of the invention is a novel group of compounds, F(CF.sub.2).sub.a CC1.sub.2 CC1.sub.2 (CF.sub.2).sub.
Type:
Grant
Filed:
September 3, 1993
Date of Patent:
June 6, 1995
Assignee:
AlliedSignal Inc.
Inventors:
Michael Van Der Puy, Alagappan Thenappan, G. V. Bindu Madhavan