Halocarbonate Esters (i.e., Compounds Having The Halo-c(=o)o- Group Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 558/280)
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Publication number: 20130303783Abstract: A continuous process for generation of phosgene from CO and Cl2 and consumption of the phosgene thus generated in a liquid-phase reaction so as to form organic products P. The process is implemented in two successive reactors R1 and R2, the first reactor R1 being a reactor for catalytic synthesis of phosgene from CO and Cl2 gas, and the second reactor R2 being a piston reactor, the second reactor R2 being equipped with a mechanical axial agitation device.Type: ApplicationFiled: September 28, 2011Publication date: November 14, 2013Applicant: AET GROUPInventors: Raimondo Pilia, Alexandre Trani, Sabrina Marie, Fabrice De Panthou
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Patent number: 7696371Abstract: A method for preparing an aliphatic chloroformate comprising, introducing a mixture of at least one aliphatic hydroxyl compound, phosgene, at least one solvent, and optionally at least one organic base into a flow reactor to obtain a unidirectional flowing reaction mixture. The at least one aliphatic hydroxyl compound comprises at least one aliphatic hydroxyl group. The unidirectional flowing reaction mixture is maintained at a temperature between about 0° C. and about 60° C. to produce a single product stream comprising an aliphatic chloroformate.Type: GrantFiled: October 19, 2004Date of Patent: April 13, 2010Assignee: SABIC Innovative Plastics IP B.V.Inventors: Gary Charles Davis, Joshua James Stone, James Manio Silva, James Alan Mahood, David Michel Dardaris
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Patent number: 7126022Abstract: The specification describes a continuous process for the preparation of monofunctional aromatic chloroformates (MAC) having the structure (I) wherein n is an integer from 1 to 5, and R1 represents hydrogen, a branched or unbranched alkyl group having from 1–15 carbon atoms, an aryl group which may be substituted or unsubstituted, a cycloaliphatic group which may be substituted or unsubstituted, or an arylalkyl group which may be substituted or unsubstituted.Type: GrantFiled: May 8, 2002Date of Patent: October 24, 2006Assignee: General Electric CompanyInventors: James Manio Silva, David Michel Dardaris, Peter David Phelps
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Patent number: 6919471Abstract: Alky/aryl chloroformates are prepared directly from alcohols and triphosgene. This method is simple, mild and efficient avoids use of hazardous phosgene. It can be used for the preparation of various aryl as well as alkyl chloroformates in excellent yields.Type: GrantFiled: September 22, 2003Date of Patent: July 19, 2005Assignee: Council of Scientific and Industrial ResearchInventors: Abdul Rakeeb Abdul Subhan Deshmukh, Vikas Kalyanrao Gumaste
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Patent number: 6878840Abstract: The dialkyl peroxydicarbonates with short alkyl chains, preferably diethyl and diisopropyl peroxydicarbonates, are used for the aqueous suspension polymerization of vinyl chloride, in the form of a solution in a dialkyl alkanedicarboxylate which is liquid and insoluble in water. The preferred solvents are hexanedicarboxylates (adipates) derived from adipic acid and from C6-C10alkanols. The peroxydicarbonate concentration of the said solutions is generally 15-40% by weight. The process according to the invention produces vinyl chloride polymers of improved quality resulting in shaped articles exhibiting markedly fewer fisheyes. The invention also relates to a two-stage process for the manufacture of a solution of dialkyl peroxydicarbonates with short alkyl chains which is particularly suited for the aqueous suspension polymerization of vinyl chloride.Type: GrantFiled: September 8, 2003Date of Patent: April 12, 2005Assignee: Solvay (Societe Anonyme)Inventor: Vincent Bodart
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Patent number: 6846888Abstract: Thermally stabilized initiator compositions comprising: (a) at least one dialkyl peroxydicarbonate, and (b) a stabilizing effective amount of a compound of Structure I: wherein R1 and R2 are as defined in the summary of the invention section, processes for their preparation and use are disclosed.Type: GrantFiled: March 21, 2002Date of Patent: January 25, 2005Assignee: ATOFINA Chemicals, Inc.Inventors: Barbara L. Stainbrook, Michael S. Mendolia, Terry N. Myers, Peter A. Callais, Joseph M. Brennan
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Publication number: 20040152911Abstract: Describes a method for obtaining substantially pure chloromethyl chloroformate from a chloroformate mixture comprising chloromethyl chloroformate and methyl chloroformate by heating the chloroformate mixture in a reaction zone at temperatures ranging from at least 50° C. to the reflux temperature of the chloroformate mixture in the reaction zone while simultaneously removing volatile gaseous decomposition products from the reaction zone. Dichloromethyl chloroformate may also be present in the chloroformate mixture.Type: ApplicationFiled: February 5, 2003Publication date: August 5, 2004Inventors: Mark P. Bowman, Charles B. Kreutzberger
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Patent number: 6696590Abstract: The disclosure relates to a process for the synthesis of substituted or unsubstituted aliphatic, cycloaliphatic or araliphatic chloroformates by reaction of the corresponding alcohol with phosgene, diphosgene and/or triphosgene. The reaction is carried out under a pressure of between 15×103 Pa and 85×103 Pa and at a temperature of between −30° C. and +50° C. The process is particularly well suited to the preparation of menthyl chloroformate and benzyl chloroformate.Type: GrantFiled: December 18, 2001Date of Patent: February 24, 2004Assignee: SNPEInventors: Hubert Bonnard, Laurence Ferruccio, Patricia Gauthier, Jean-Pierre Senet
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Publication number: 20030236428Abstract: A method of preparing a dialkyl carbonate includes reacting an alkanol, oxygen, carbon monoxide, and a catalyst to form a mixture that includes a dialkyl carbonate and an alkyl chloroformate. The mixture is separated into a liquid fraction and a gaseous fraction, and alkyl chloroformate is removed from the gaseous fraction. Also described is an apparatus for carrying out the method. The method is particularly useful for preventing corrosion in a cold wash unit that removes further organic impurities from the gaseous fraction.Type: ApplicationFiled: June 2, 2003Publication date: December 25, 2003Applicant: GENERAL ELECTRIC COMPANYInventors: Jan van de Broek, Stephan Bouwens, Maarten Campman, Daniel Favre, Cornelis Adrianus Maria van Gool, Leon Kalle, George P. Moloney
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Patent number: 6667341Abstract: Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, sulfur or nitrogen attached to a methylene group, to which is further attached a sulfur, nitrogen or CH2 group. Methods of treating illnesses and conditions, such as cancer, hemological disorders, inherited metabolic disorders and others, using these compounds are also disclosed.Type: GrantFiled: May 17, 2001Date of Patent: December 23, 2003Assignee: Beacon Laboratories, Inc.Inventors: Hsuan-Yin Lan-Hargest, Norbert L. Wiech
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Publication number: 20030120103Abstract: A process for the preparation of fluoroformates of the formula 1Type: ApplicationFiled: December 18, 2002Publication date: June 26, 2003Inventors: Alphonse Alarcon-Lorca, Thierry Malfroot, Jean-Pierre Senet
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Publication number: 20030078449Abstract: The specification describes a continuous process for the preparation of monofunctional aromatic chloroformates (MAC) having the structure (I) 1Type: ApplicationFiled: May 8, 2002Publication date: April 24, 2003Applicant: General Electric Co.Inventors: James Manio Silva, David Michel Dardaris, Peter David Phelps
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Patent number: 6479690Abstract: The invention concerns a method for phosgenation of monohydroxy alcohol's and/or polyols characterised in that it consists of treating alcohol and or polyol, whether in the presence of solvent or not, with a molar excess of phosgene, preferably 2 to 30 times more phosgene than the hydroxyl groups, at temperatures ranging between 0 and 200° C. and at pressure levels ranging between 2 and 60 bar, preferably in the absence of any catalyst. The method is further characterised in that pressure is further used to facilitate the separation of hydrochloric acid from phosgene, in a column external to the reactor.Type: GrantFiled: March 6, 2000Date of Patent: November 12, 2002Assignee: Societe Nationale des Poudres et ExplosifsInventors: Laurent Garel, François Metz
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Patent number: 6392079Abstract: A continuous process for the preparation of monofunctional aromatic chloroformates (MAC) having the structure (I) wherein n is an integer from 1 to 5, and R1 represents hydrogen, a branched or unbranched alkyl group having from 1-15 carbon atoms, an aryl group which may be substituted or unsubstituted, a cycloaliphatic group which may be substituted or unsubstituted, or an arylalkyl group which may be substituted or unsubstituted, the method comprising the steps of a) introducing 1) an aqueous caustic solution; 2) a carbonyl chloride; 3) at least one monofunctional hydroxyaromatic compound; and 4) at least one inert organic solvent into a continuous reaction system; and b) effecting contact between 1), 2), 3) and 4) for a time and at conditions sufficient to produce a MAC of structure (I).Type: GrantFiled: March 30, 1999Date of Patent: May 21, 2002Assignee: General Electric CompanyInventors: James Manio Silva, David Michel Dardaris, Peter David Phelps
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Patent number: 6258906Abstract: The dialkyl peroxydicarbonates with short alkyl chains, are used for the aqueous suspension polymerization of vinyl chloride, in the form of a solution in a dialkyl alkanedicarboxylate. The preferred solvents are hexanedicarboxylates (adipates) derived from adipic acid and C6-C10 alkanols. The peroxydicarbonate concentration of the said solutions is generally 15-40% by weight. The process according to the invention produces vinyl chloride polymers of improved quality resulting in shaped articles exhibiting markedly fewer fisheyes. The invention also relates to a two-stage process for the manufacture of a solution of dialkyl peroxydicarbonates with short alkyl chains which is particularly suited for the aqueous suspension polymerization of vinyl chloride. According to this process an inorganic salt is used in the stage of manufacture of the peroxydicarbonate (first stage) and the latter is subsequently isolated by extraction by means of a water-insoluble solvent (second stage).Type: GrantFiled: April 23, 1999Date of Patent: July 10, 2001Assignee: SolvayInventor: Vincent Bodart
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Patent number: 6175017Abstract: A process for the preparation of carbonates containing aromatic ester groups is disclosed. The process entails reacting aromatic monohydroxy componds with phosgene or with chlorocarbonic acid esters of aromatic monohydroxy compounds at a temperature of 50 to 350° C. and in the presence of active carbon as catalyst.Type: GrantFiled: August 18, 1993Date of Patent: January 16, 2001Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Norbert Schön, G{umlaut over (u)}nther Jeromin
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Patent number: 5892091Abstract: A catalyst composed of an organic phosphorus compound having a trivalent or pentavalent phosphorus atom and at least one carbon-phosphorus bonding or a combination of the organic phosphorus compound and a halogen atom-containing compound is effective for decarbonylation, that is, for releasing carbon monoxide from a compound containing a moiety of --CO--CO--O-- in its molecular structure.Type: GrantFiled: July 8, 1997Date of Patent: April 6, 1999Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Yoichi Imbe, Keigo Nishihira, Shuji Tanaka, Satoru Fujitsu, Ryoji Sugise, Koichi Kashiwagi, Toshihiko Sumida, Takashi Doi, Masayuki Nishio
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Patent number: 5869729Abstract: An ester compound, for example, carbonic acid ester or succinic acid ester, is produced by catalytically reacting, in gas phase, carbon monoxide with a nitrous acid ester and optionally an olefin in the presence of a catalyst and in the presence of a chlorine-containing substance, bringing the reaction product-containing mixed gas into contact with a solid catalyst such as activated carbon or inorganic oxide to reduce the content of the chlorine-containing substance, cool-condensing the resultant mixed gas, and collecting the target ester compound from the condensed liquid.Type: GrantFiled: June 27, 1996Date of Patent: February 9, 1999Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Shuji Tanaka, Yuki Nishida, Noriaki Manada, Toshio Kurafuji, Masato Murakami
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Patent number: 5637719Abstract: The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.Type: GrantFiled: June 6, 1995Date of Patent: June 10, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Michael Philbin
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Patent number: 5401868Abstract: The present invention relates to hitherto unknown intermediate of formula, in which R.sub.1 stands for hydrogen or a straight or branched aliphatic C.sub.1 -C.sub.20 carbon chain or an aryl or aralkyl group, aryl and "ar" meaning an aromatic or heterocyclic, 5- or 6-membered ring substituent containing 1 or 2 hetero atoms selected among O, S and N, R.sup.1 optionally being further substituted, and its chain being interrupted by hetero atoms like oxygen, or by carbonyl group(s); and R.sup.3 stands for hydrogen or C.sub.1 -C.sub.3 alkyl. The present intermediates can be used in a one step method for producing prodrugs of formula, where D-H =drug itself.Type: GrantFiled: February 26, 1992Date of Patent: March 28, 1995Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)Inventor: Frantz J. Lund
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Patent number: 5221754Abstract: This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group;R.sub.1 is H or COZ;X.sub.1 and X.sub.2 are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; andZ is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.Type: GrantFiled: September 14, 1992Date of Patent: June 22, 1993Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Michael Philbin
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Patent number: 4814420Abstract: A method is provided for determining the stoichiometric end point of phosgenation reactions which produce polycarbonates and chloroformates, respectively, by monitoring the rate of heat generated by the reaction mixture per unit of phosgene utilized.Type: GrantFiled: November 25, 1987Date of Patent: March 21, 1989Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon, Philip G. Kosky, Paul W. Buckley, James M. Silva
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Patent number: 4810813Abstract: A method is provided for making reaction products of phosgene and dihydric phenol under interfacial reaction conditions. The dihydric phenol such as BPA is introduced into the reactor in the form of a stable suspension which reduces phosgene hydrolysis, minimizes phosgene escape and effects improved BPA metering into the reactor.Type: GrantFiled: July 24, 1987Date of Patent: March 7, 1989Assignee: General Electric CompanyInventors: Philip G. Kosky, James M. Silva, Thomas J. Fyvie
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Patent number: 4808743Abstract: Vinyl chloroformates are described of formula ##STR1## in which: R.sub.1 .dbd.R.sub.2 .dbd.Cl, Br or a saturated 1-4 carbon atom alkyl or together they form a cycloaliphatic ring of 4-8 carbon atoms;R.sub.3 .dbd.H when R.sup.1 or R.sup.2 .dbd.alkyl; saturated alkyl of 1-4 carbon atoms or aryl; ##STR2## in which R.sub.4 .dbd.R.sub.5 .dbd.alkyl of 1-4 carbon atoms or R.sub.3 forms with R.sub.2 a C.sub.5 -C.sub.8 ring which may have attached oxygen atoms. The process of preparation consists of reacting phosgene with the corresponding compounds containing alpha halogen and a carbonyl group. The products are very useful to obtain vinyl carbonates and carbamates.Type: GrantFiled: February 13, 1987Date of Patent: February 28, 1989Assignee: Societe Nationale des Poudres et ExplosifsInventors: Mark Bowman, Roy Olofson, Thierry Malfroot, Jean-Pierre Senet
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Patent number: 4786745Abstract: Novel 2,2-dihalovinyl haloformates are described of general formula: ##STR1## in which: X is a chlorine or bromine atom;X.sub.1 and X.sub.2 are the same or different and are chlorine or bromine.The compounds are prepared by reaction of a 1,2,2,2-tetrahaloethyl haloformate of formula: ##STR2## in which: X.sub.1, X.sub.2 and X are as described hereinabove;X.sub.3 is chlorine or bromine and is always bromine when X.sub.1 and/or X.sub.2 is bromine andX.sub.4 is chlorine or bromine, with a metal such as zinc or magnesium in a solvent.The novel compounds are very useful for the preparation of 2,2-dihalovinyl carbonates and carbamates which may be used as insecticides or as comonomers.Type: GrantFiled: August 13, 1986Date of Patent: November 22, 1988Assignee: Societe Nationale des Poudres et ExplosifsInventors: Mark P. Bowman, Roy A. Olofson, Thierry Malfroot, Jean-Pierre Senet
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Patent number: 4722995Abstract: A method is provided for determining the stoichiometric end point of phosgenation reactions which produce polycarbonates and chloroformates, respectively, by monitoring the rate of heat generated by the reaction mixture per unit of phosgene utilized.Type: GrantFiled: April 25, 1986Date of Patent: February 2, 1988Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon, Philip G. Kosky, Paul W. Buckley, James M. Silva
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Patent number: 4701544Abstract: A method is provided for making reaction products of phosgene and dihydric phenol, such as bischloroformates and polycarbonates utilizing a reactor with an overhead condenser. Reduced phosgene blow-by is achieved by using an absorber for phosgene which is connected in series to the overhead condenser.Type: GrantFiled: August 4, 1986Date of Patent: October 20, 1987Assignee: General Electric CompanyInventor: James M. Silva
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Patent number: 4638077Abstract: Chloroformate compositions, particularly bischloroformate compositions, are prepared by the reaction of phosgene with a hydroxy compound, preferably a dihydroxy compound such as bisphenol A, in a heterogeneous mixture, while adding a hydrogen chloride scavenger comprising aqueous base as necessary and maintaining a pH of 0.5-8 during the phosgene addition. When a polyhydroxy compound is employed and the temperature is above 30.degree. C., the phosgene addition rate is maintained at a level high enough to effect rapid and complete reaction with dissolved hydroxy compound. This method uses substantially less phosgene than methods involving a higher pH.Type: GrantFiled: October 24, 1985Date of Patent: January 20, 1987Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas G. Shannon, Niles R. Rosenquist
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Patent number: 4612143Abstract: A process for the preparation of fluoroformates of formula: ##STR1## in which R.sup.1 is a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical, or substituted or unsubstituted araliphatic radical or an aromatic radical, which consists of reacting a carbonate of formula: ##STR2## in which R.sup.1 has the same meaning as hereinabove and R.sup.2 is hydrogen, alkyl of 1-12 carbon atoms, cycloalkyl of 5-12 carbon atoms, saturated or unsaturated, unsubstituted or substituted by one or more halogen atoms or R.sup.2 is aryl, unsubstituted or substituted by one or more halogen atoms, with an alkali or alkaline earth fluoride, ammonium fluoride or a quaternary ammonium fluoride, of formula FNR.sup.3 R.sup.4 R.sup.5 R.sup.6, wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6 are the same or different and are hydrogen, alkyl or aralkyl of 1-12 carbon atoms or a fluoride which is KHF.sub.2, NH.sub.4 HF.sub.2 or KSO.sub.2 F.Type: GrantFiled: September 17, 1984Date of Patent: September 16, 1986Assignee: Societe Nationale des Poudres et ExplosifsInventors: Marc Piteau, Jean-Pierre Senet, Patrick Wolf, Roy A. Olofson, Vu A. Dang
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Patent number: 4584142Abstract: Organic peroxydicarbonates represented by the following graphic formula are described. ##STR1## In the formula, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently selected from an alkyl group containing from 1 to 4 carbon atoms. R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 can participate in a cycloalkyl group having from 3 to 6 carbon atoms. The peroxydicarbonates are useful as initiators for the polymerization or copolymerization of ethylenically unsaturated monomers or the cross-linking of unsaturated polyester resins. The organic peroxydicarbonates can be used in combination with commercially available peroxydicarbonates, particularly those having a longer half-life, or with peresters, diacylperoxides and azo compounds.Type: GrantFiled: November 3, 1983Date of Patent: April 22, 1986Assignee: PPG Industries, Inc.Inventors: Robert H. Tang, James A. Barter