Patents Represented by Attorney J. Frederick Thomsen
  • Patent number: 5466759
    Abstract: Disclosed are novel saturated polyether compounds comprised of n units of residue (1) and m units of residue (2), wherein (i) residues (1) and (2) have the structures: ##STR1## (ii) the total value of n+m is 2 to 70 and m/(n+m) is 0.05 to 0.98; (ii) at least 98 percent of the terminal hydroxyl groups of the polyether have the structure: ##STR2## The polyethers are obtained by first polymerizing 3,4-epoxy-1-butene to produce unsaturated polyether precursors comprising residues (1A) and (2A) having the structures: ##STR3## and then hydrogenating the unsaturated polyether precursors. The hydrogenation advantageously is performed in the presence of a nickel hydrogenation catalyst.
    Type: Grant
    Filed: October 24, 1994
    Date of Patent: November 14, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Stephen N. Falling
  • Patent number: 5446106
    Abstract: Copolymers are produced when a 4-vinyl-1,3 dioxolane monomer is copolymerized with an imidized maleic anhydride (for example, maleimide) monomer in the presence of a free radical initiator. Alternatively, a maleamic acid or maleimide functionality may be introduced into a copolymer containing a 4-vinyl-1,3 dioxolane and maleic anhydride by introducing a primary amine into the reaction mixture. Also, the dioxolane reactant may be introduced into the polymer by reacting 3,4-epoxy-1-butene in a ketone reaction solvent. The structure and composition of the product copolymer are controlled by both the sequence and conditions of the reaction. Products of the present invention can be cast as clear films and can also be used as reactive polymers.
    Type: Grant
    Filed: January 3, 1995
    Date of Patent: August 29, 1995
    Assignee: Eastman Chemical Company
    Inventors: Richard W. Blevins, S. Richard Turner
  • Patent number: 5445963
    Abstract: A process is disclosed for the separation of an enantiomerically enriched 1-tosyloxy-2-acyloxy-3-butene and an enantiomerically enriched 1-tosyloxy-2-hydroxy-3-butene from a first mixture containing both compounds. The process includes the steps of:(a) forming a solution of the mixture in an organic solvent;(b) bringing the solution formed in (a) to a temperature wherein most of the enantiomerically enriched 1-tosyloxy-2-hydroxy-3-butene precipates, leaving in solution most of the enantiomerically enriched 1-tosyloxy-2-acyloxy-3-butene; and(c) separating the precipitate formed in (b) from the solution.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: August 29, 1995
    Assignee: Eastman Chemical Company
    Inventor: Neil W. Boaz
  • Patent number: 5434271
    Abstract: Disclosed are a novel class of 1-hydroxy-6-organosulphonylindoles and a process for the preparation thereof.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: July 18, 1995
    Assignee: Eastman Chemical Company
    Inventor: Raymond Fisher
  • Patent number: 5434314
    Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of an acidic catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, n/(n+m) is a value in the range of 0.70 to 0.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: July 18, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Stephen N. Falling
  • Patent number: 5418294
    Abstract: Copolymers are produced when a 4-vinyl-1,3 dioxolane monomer is copolymerized with an imidized maleic anhydride (for example, maleimide) monomer in the presence of a free radical initiator. Alternatively, a maleamic acid or maleimide functionality may be introduced into a copolymer containing a 4-vinyl-1,3 dioxolane and maleic anhydride by introducing a primary amine into the reaction mixture. Also, the dioxolane reactant may be introduced into the polymer by reacting 3,4-epoxy-1-butene in a ketone reaction solvent. The structure and composition of the product copolymer are controlled by both the sequence and conditions of the reaction. Products of the present invention can be cast as clear films and can also be used as reactive polymers.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: May 23, 1995
    Assignee: Eastman Chemical Company
    Inventors: Richard W. Blevins, S. Richard Turner
  • Patent number: 5414159
    Abstract: A process is described for the production of cyclohexanedimethanol by hydrogenation of a dialkyl cyclohexanedicarboxylate which comprises the steps of:(a) providing a hydrogenation zone containing a charge of a granular reduced manganese promoted copper catalyst;(b) forming a vaporous feed stream of a hydrogenatable material comprising a dialkyl cyclohexanedicarboxylate and from about 0.1 wt % up to about 15 wt % of an acidic material at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure which is in the range of from about 150 psia (about 10.34 bar) up to about 2000 psia (about 137.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: May 9, 1995
    Assignee: Eastman Chemical Company
    Inventors: Paul Appleton, Michael A. Wood
  • Patent number: 5406004
    Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof, at an inlet temperature which is above the dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) recovering from the hydrogenation zone a two phase product stream containing a hydroxylic compou
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventors: Philip H. D. Eastland, John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5406007
    Abstract: Disclosed is a process for the conversion of conjugated epoxyalkenes to unsaturated alcohols wherein a conjugated epoxyalkene is catalytically hydrogenated in the presence of a sulfur-modified or sulfided nickel catalyst whereby the epoxide ring is hydrogenolyzed without concomitant hydrogenation of the olefinic unsaturation thereby producing allylic and/or homoallylic alcohols.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventor: Stephen N. Falling
  • Patent number: 5399752
    Abstract: Disclosed is a process for the purification of carboxyl streams such as product streams comprising one or more carboxyl compounds selected from carboxylic acids, carboxylic anhydrides and alkylidene dicarboxylates. The process provides a means for the reduction of the iodine content of carboxyl compound product streams which are contaminated with one or more iodine compounds.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: March 21, 1995
    Assignee: Eastman Chemical Company
    Inventors: Stanley J. Okrasinski, Regina M. Moncier, Patricia N. Mercer, Dewey W. Fuller, Jr., Steven L. Cook
  • Patent number: 5399742
    Abstract: Disclosed is a process for the manufacture of dialkyl cyclohexanedicarboxylates by the low pressure, catalytic hydrogenation of the corresponding dialkyl benzenedicarboxylate wherein the formation/accumulation of carbon monoxide is suppressed to maintain the activity of the precious metal catalyst.
    Type: Grant
    Filed: April 11, 1994
    Date of Patent: March 21, 1995
    Assignee: Eastman Chemical Company
    Inventors: Brent A. Tennant, Mark D. Williams, Bruce L. Gustafson
  • Patent number: 5395987
    Abstract: A continuous process is described for the production of 1,4-cyclohexanedimethanol (CHDM) having a desired or predetermined trans-:cis- isomer ratio by catalytic hydrogenation of a dialkyl 1,4-cyclohexanedicarboxylate in the presence of an ester hydrogenation catalyst. The process is capable of being operated for an extended period of time during which the hydrogenation catalyst declines in catalytic activity and comprises feeding a vaporous mixture of the dialkyl 1,4-cyclohexanedicarboxylate and hydrogen to a hydrogenation zone containing the hydrogenation catalyst and recovering CHDM product. The degree of conversion of the dialkyl 1,4-cyclohexanedicarboxylate at a particular combination of temperature and pressure is related to the trans-:cis- isomer ratio of the CHDM product and may be varied by adjusting at least one feed condition selected from (i) the dialkyl 1,4-cyclohexanedicarboxylate feed rate and (ii) the hydrogen-containing gas:dialkyl 1,4-cyclohexanedicarboxylate molar ratio.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: Colin Rathmell, Richard C. Spratt, Michael W. M. Tuck
  • Patent number: 5395991
    Abstract: A hydrogenation process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding unsaturated organic compound selected from esters, diesters and lactones which involves use of two hydrogenation zones (11, 36), each containing a charge of a hydrogenation catalyst (12, 37). In a first phase of operation one of the hydrogenation zones (36 or 11) is in standby condition and a stream of hot hydrogen-containing gas is passed therethrough. Meanwhile a vaporous feed stream comprising a hydrogen-containing gas and the unsaturated organic compound to be hydrogenated, e.g. dimethyl 1,4-cyclohexanedicarboxylate, is fed to the active zone (11 or 36). This feed stream can include the gas stream from the first mentioned hydrogenation zone (36 or 11).
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5395986
    Abstract: A process is described for the production of cyclohexanedimethanol having a trans-:cis-isomer ratio greater than about 1:1 by hydrogenation of a dialkyl (e.g. dimethyl) cyclohexanedicarboxylate having a trans-:cis-isomer ratio less than about 1:1 which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenarable material comprising a dialkyl cyclohexanedicarboxylate at an inlet temperature which is above its dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) passing the vaporous feed stream through the hydrogenation zone; and(e) recovering from the hydrogenation zone a product stream containing cyclohexanedimethanol having a trans-:cis-isomer ratio greater than 1:1.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael A. Wood
  • Patent number: 5395990
    Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, aldehydes, olefinically unsaturated aldehydes, and mixtures of two or more thereof, which process comprises the steps of:(a) providing a hydrogenation zone containing a charge of a granular hydrogenation catalyst which has a total surface area of at least about 15 m.sup.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventor: John Scarlett
  • Patent number: 5393867
    Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of a palladium(O) catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, m/(n+m) is greater than 0.30 and up to 0.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: February 28, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Falling: Stephen N.
  • Patent number: 5391773
    Abstract: Disclosed is a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycycloalkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and .gamma.,.delta.-epoxycycloalkenes, to the corresponding epoxyalkanes and epoxycycloalkanes using a solution of a complex rhodium catalyst whereby the olefinic unsaturation is hydrogenated without significant hydrogenolysis of the conjugated epoxy group.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: February 21, 1995
    Assignee: Eastman Chemical Company
    Inventor: Thomas A. Puckette
  • Patent number: 5387753
    Abstract: A process is described for reactivating an at least partially deactivated copper-containing ester hydrogenation catalyst which has undergone deactivation through use in hydrogenation of an unsaturated organic compound selected from esters of C.sub.8 to C.sub.22 monocarboxylic acids, diesters of dicarboxylic acids, and lactones, to yield a corresponding hydroxylic compound selected from alcohols and diols which comprises contacting the at least partially deactivated copper-containing catalyst at an effective reactivation temperature and for an effective period of time with a stream of hydrogen-containing gas which is substantially free from the unsaturated organic compound thereby to reactivate the at least partially deactivated copper-containing catalyst.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: February 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5387752
    Abstract: A process is described for the production of cyclohexanedimethanol by hydrogenation of a dialkyl cyclohexanedicarboxylate which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) forming a vaporous feed stream of a hydrogen-containing gas,and a hydrogenatable material comprising a dialkyl cyclohexanedicarboxylate at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure in the range of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: February 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael A. Wood, Colin Rathmell
  • Patent number: 5370938
    Abstract: Disclosed are polyester adhesive compositions which exhibit increased melt viscosity and improved adhesion comprised of residues of terephthalic acid, ethylene glycol and diethylene glycol and having reacted therewith or copolymerized therein the residue of a phosphite ester compound and optionally containing a phenolic antioxidant. Also disclosed are articles coated with the polyester compositions and bonded laminate articles based on the compositions.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: December 6, 1994
    Assignee: Eastman Chemical Company
    Inventors: Alan W. White, Barry G. Pearcy, Marc A. Strand, Joey C. Carico