Patents Represented by Attorney, Agent or Law Firm Michael J. Blake
  • Patent number: 6100431
    Abstract: The preparation of aromatic ketones substituted with a thioether group at the ortho position is accomplished by the initial reaction of an aromatic nucleus substituted with a halide and an ortho nitro group with a nitroalkane in the presence of a hydroxide base. The resulting ortho-nitroalkyl nitroarene compound is converted to the corresponding ortho-nitroaryl ketone by an oxidative Nef reaction. The aromatic nitro group of the ortho-nitroaryl ketone is replaced with a thioether group by reaction with a thiolate anion, most preferably under phase-transfer conditions. Aromatic ketones may be used to prepare various pharmaceutical and herbicidal compounds.
    Type: Grant
    Filed: June 2, 1998
    Date of Patent: August 8, 2000
    Assignee: Eastman Chemical Company
    Inventor: Neil W. Boaz
  • Patent number: 6096929
    Abstract: The preparation of aromatic ketones substituted with a thioether group at the ortho position is accomplished by the initial reaction of an aromatic nucleus substituted with a halide and an ortho nitro group with a nitroalkane in the presence of a hydroxide base. The resulting ortho-nitroalkyl nitroarene compound is converted to the corresponding ortho-nitroaryl ketone by an oxidative Nef reaction. The aromatic nitro group of the ortho-nitroaryl ketone is replaced with a thioether group by reaction with a thiolate anion, most preferably under phase-transfer conditions. Aromatic ketones may be used to prepare various pharmaceutical and herbicidal compounds.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: August 1, 2000
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 6090982
    Abstract: Disclosed is a process for the preparation of cyclopropylglycine by a 5-step process wherein cyclopropanecarboxaldehyde is reacted with an .alpha.-aminoalkylaromatic compound to obtain an imine which is reacted with a cyanide to produce an aminonitrile compound; the aminonitrile compound is hydrolyzed to the corresponding aminocarboxylic acid and finally the arylalkyl residue is removed from the amino group by hydrogenolysis.
    Type: Grant
    Filed: November 16, 1999
    Date of Patent: July 18, 2000
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Gruman, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
  • Patent number: 6077981
    Abstract: Disclosed is a process for the production of cyclopropylmethyl halides (CPMX) such as cyclopropylmethyl chloride (CPMCl) and cyclopropylmethyl bromide (CPMBr) wherein cyclopropanemethanol (CPMO) is contacted with an aqueous solution of a hydrogen halide (HX) at a temperature in the range of -30.degree. C. to 35.degree. C. Also disclosed is a three-step process wherein CPMO is converted to a CPMX, the CPMX is separated as a liquid organic phase from the aqueous hydrogen halide by decantation and then is subjected to fractional distillation to provide CPMX in high purity. Finally, a process for the co-production of a CPMX and a cyclobutyl halide (CBX) is disclosed.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: June 20, 2000
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Colin Henry Ridyard, Daniel Latham Terrill, Clyde Neil Clubb
  • Patent number: 6072079
    Abstract: Disclosed is a continuous process for the production of 3,4-diacetoxy-1-butene (DAcB) by the reaction of 3,4-epoxy-1-butene (EpB) with acetic anhydride (Ac.sub.2 O) in the presence of potassium acetate (KOAc) wherein the KOAc is formed in situ by contacting EpB, acetic anhydride and a potassium salt selected from potassium carbonate, potassium bicarbonate, potassium hydroxide or a mixture of any two or more thereof at elevated temperatures.
    Type: Grant
    Filed: March 3, 1999
    Date of Patent: June 6, 2000
    Assignee: Eastman Chemical Company
    Inventor: Steven Leroy Cook
  • Patent number: 6057438
    Abstract: Disclosed is a process for upgrading paper-grade wood pulp to dissolving grade pulp which is suitable for use in the preparation of viscose rayon, cellulose ethers and cellulose esters such as cellulose acetate. The process utilizes a sequence of caustic extraction, xylanase treatment and caustic extraction to remove most of the xylan, which may be recovered for use in the production of xylose, xylitol, and furans.
    Type: Grant
    Filed: October 2, 1997
    Date of Patent: May 2, 2000
    Assignee: Eastman Chemical Company
    Inventors: John Anthony Hyatt, Richard William Fengl, Kevin Joseph Edgar, Maria Teresa Alvarez-Wright
  • Patent number: 6033447
    Abstract: Coal gasifiers using technology developed by Texaco Development Corporation, use coal slurry and oxygen as feed stocks. During start-ups, the raw gas produced in the gasifier must be flared until the downstream clean-up and recovery plants can be started. In order to reduce emissions through the flare during start-up, a technique was developed to start the gasifiers and downstream plants on a sulfur free, liquid, organic fuel. Once downstream plants are on-line, the fuel feed is switched to coal slurry on the same burner. The switch is accomplished while maintaining pressure and without interrupting to the fuel feed.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: March 7, 2000
    Assignee: Eastman Chemical Company
    Inventors: Nathan West Moock, William Lewis Trapp
  • Patent number: 6034276
    Abstract: Disclosed is an improved process for preparing 1-chloro-2,4-diaminobenzene by the selective hydrogenation of 1-chloro-2,4-dinitro-benzene wherein the hydrogenation is carried out in the presence of a modified Raney nickel catalyst containing about 70 to 95 weight percent nickel, about 4 to 10 weight percent aluminum, about 0.1 to 4 weight percent molybdenum, and from 0 to about 20 weight percent cobalt. The 1-chloro-2,4-diaminobenzene is useful as an intermediate for disperse dyes and for color photography.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: March 7, 2000
    Assignee: Eastman Chemical Company
    Inventors: Robert Joseph Maleski, Edward Tipton Mullins
  • Patent number: 6028213
    Abstract: Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters of >90% enantiomeric excess (ee) and methods of preparing the monoesters are described. One method contacts a cis-1,3-cyclohexanedicarboxylic acid diester with a lipase under aqueous conditions to enantioselectively produce the optically active cis-1,3-cyclohexanedicarboxylic acid monoester. Another method reacts a mixture of cis- and trans-1,3-cyclohexanedicarboxylic acids under conditions sufficient to form a cis-cyclic anhydride, esterifies the cis-cyclic anhydride to produce a cis-1,3-cyclohexanedicarboxylic acid diester and then contacts under aqueous conditions the diester with a lipase to enantioselectively produce the optically active cis-1,3-cyclohexanedicarboxylic acid monoester.
    Type: Grant
    Filed: April 16, 1998
    Date of Patent: February 22, 2000
    Assignee: Eastman Chemical Company
    Inventor: Neil W. Boaz
  • Patent number: 5990313
    Abstract: Disclosed is a process for the preparation of 3-alkyltetrahydrofurans by a two-step process wherein 2,3-dihydrofuran is reacted with an acetal to form an intermediate compound which may be converted to a 3-alkyltetrahydrofuran by contacting the intermediate with hydrogen in the presence of a catalytic amount of a Group VIII noble metal or rhenium, water and a strong acid.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: November 23, 1999
    Assignee: Eastman Chemical Company
    Inventor: William Anthony Beavers
  • Patent number: 5990323
    Abstract: Disclosed is a process for the preparation of an amine by contacting in a reaction zone a water-soluble aldehyde, water, ammonia and hydrogen in the presence of a supported ruthenium catalyst at elevated temperature and pressure. The process is particularly useful for the preparation of 3-(aminomethyl)tetrahydrofuran by contacting an aqueous solution of 3-formyltetrahydrofuran with ammonia and hydrogen at elevated temperature and pressure in the presence of a supported ruthenium catalyst. The use of a supported ruthenium catalyst has been found to avoid the problem of catalyst leaching encountered when a nickel catalyst is used.
    Type: Grant
    Filed: October 23, 1998
    Date of Patent: November 23, 1999
    Assignee: Eastman Chemical Company
    Inventor: Clyde Neal Clubb
  • Patent number: 5986141
    Abstract: Disclosed is a process for the preparation of cyclopropanemethylamine (CPMA) from cyclopropanecarboxaldehyde (CPCA), ammonia and hydrogen by a two-step process wherein CPCA is contacted with ammonia to form an imine followed by the hydrogenation of the imine in the presence of a nickel or cobalt catalyst to obtain CPMA in high yields and high selectivity.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: November 16, 1999
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 5977407
    Abstract: Disclosed is a process for the preparation of an aliphatic carbonyl derivative compound having a normal:iso ratio of at least 3, and preferably 4, selected from aliphatic carboxylic acids, alkylesters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by the hydrocarboxylation of terminal linear olefins in the presence of a catalyst system comprising (1) a rhodium containing compound, (2) a halide promoter selected from iodine, bromine and compounds thereof and (3) a trisubstituted organic compound of a group-15 element, preferably a phosphine or arsine. This process constitutes an improvement over known processes since it provides a one-step, lower pressure, higher reaction rate method of producing carboxylic acid derivatives having an increased normal:iso ratio in the absence of potentially hazardous chlorinated hydrocarbons and aromatic hydrocarbons.
    Type: Grant
    Filed: August 10, 1998
    Date of Patent: November 2, 1999
    Assignee: Eastman Chemical Company
    Inventor: Joseph Robert Zoeller
  • Patent number: 5945549
    Abstract: Disclosed is a process for the recovery of formyltetrahydrofurans (FTHF's) produced by the rhodium-catalyzed hydroformylation of 2,5-dihydrofuran (2,5-DHF) wherein the FTHF's are recovered as an equilibrium mixture of 2- & 3-FTHF and their hydrates, 2- and 3-?di(hydroxy)methyl!tetrahydrofuran from a hydroformylation product solution comprising a rhodium catalyst, 2- and 3-FTHF and an organic hydroformylation solvent obtained as a liquid product take-off from a hydroformylation process wherein 3-FTHF is produced by the hydro-formylation of 2,5-DHF 3-FTHF is a valuable organic intermediate useful, for example, in the preparation of 3-methyltetrahydrofuran and 3-amino-methyltetrahydorfuran.
    Type: Grant
    Filed: January 22, 1999
    Date of Patent: August 31, 1999
    Assignee: Eastman Chemical Company
    Inventor: William Anthony Beavers
  • Patent number: 5936117
    Abstract: Disclosed is a process for the preparation of aliphatic carbonyl compounds selected from aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by the carbonylation of olefins in the presence of a catalyst system comprising (1) a primary component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a secondary component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic. The process constitutes and improvement over known processes since it can be carried out at moderate carbonylation conditions without the necessity of using an expensive noble metal catalyst, volatile, toxic materials such as nickel tetracarbonyl, formic acid or a formate ester.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: August 10, 1999
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Elizabeth MacGowan West, Horace Lawrence Browning, Jr., George Geiger Mayfield
  • Patent number: 5912364
    Abstract: Disclosed is a process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) which comprises contacting 3-formyltetrahydrofuran with hydrogen in the presence of a catalyst system comprising a Group VIII noble metal or rhenium and a strong acid under hydrogenolysis conditions of temperature and pressure to produce 3-MeTHF. The 3-MeTHF produced in accordance with the present invention is useful as an industrial solvent and, more importantly, as a monomer in the manufacture of polymers such as elastomers.
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: June 15, 1999
    Assignee: Eastman Chemical Company
    Inventor: William Anthony Beavers
  • Patent number: 5908942
    Abstract: Disclosed is a process for the selective epoxidation of olefins, including diolefins, having more than 2 carbon atoms by the catalytic oxidation of such an olefin in the presence of a supported, fluorine-promoted, silver catalyst.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: June 1, 1999
    Assignee: Eastman Chemical Company
    Inventors: George Leslie Oltean, John Robert Monnier
  • Patent number: 5905176
    Abstract: Disclosed is a process for the production of cyclobutyl halides such as cyclobutyl chloride and cyclobutyl bromide wherein cyclopropanemethanol is contacted with an aqueous solution of a hydrogen halide at a temperature in the range of greater than 35.degree. C. up to 120.degree. C.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: May 18, 1999
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 5900505
    Abstract: Disclosed is a process wherein a mixture of methanol or a methanol source, a halide and carbon monoxide are contacted in the vapor phase with a supported catalyst comprising iridium and at least one second metal selected from ruthenium, molybdenum, tungsten, palladium, platinum and rhenium deposited on a catalyst support material.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: May 4, 1999
    Assignee: Eastman Chemical Company
    Inventors: Gerald Charles Tustin, Joseph Robert Zoeller, Horace Lawrence Browning, Jr., Andy Hugh Singleton
  • Patent number: 5900504
    Abstract: Disclosed is an improved liquid phase process for the preparation of an acetyl product comprising acetic acid, by the carbonylation of a carbonylatable reactant material comprising methanol, methyl acetate, dimethyl ether or a mixture thereof in the presence of a catalyst system comprising a nickel component and an iodide component. In the separation of the crude acetyl product mixture from a liquid containing the non-volatile catalyst components, precipitation of metals and other catalyst components is avoided or minimized by maintaining a hydrogen pressure of at least 0.34 bar absolute within the flash evaporator zone wherein the separation occurs.
    Type: Grant
    Filed: February 20, 1996
    Date of Patent: May 4, 1999
    Assignee: Eastman Chemical Company
    Inventors: Jeffrey Scott Kanel, Stanley John Okrasinski