Abstract: Polyether polymers obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of an onium iodide compound such as an ammonium or phosphonium iodide, an organotin compound such as a trihydrocarbyltin iodide, and a nucleophilic hydroxyl initiator compound. The polyether polymers 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 0.75 and up to 0.
Type:
Grant
Filed:
September 22, 1995
Date of Patent:
March 4, 1997
Assignee:
Eastman Chemical Company
Inventors:
Stephen N. Falling, Stephen A. Godleski, Patricia Lopez-Maldonado, Peter B. MacKenzie, Laughlin G. McCullough, James C. Matayabas, Jr.
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-l-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:
August 28, 1995
Date of Patent:
March 4, 1997
Assignee:
Eastman Chemical Company
Inventors:
James C. Matayabas, Jr., Stephen N. Falling
Abstract: Disclosed is a process for the preparation of 2,5-dihydrofuran compounds by contacting an olefinically-substituted ethylene carbonate compound with a catalyst comprising an acidic component and a halogen component. The process is especially useful for the preparation of 2,5-dihydrofuran from vinyl ethylene carbonate (4-ethenyl-1,3-dioxolane-2-one) which is readily available from 3,4-epoxy-1-butene.
Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of tetrahydrofuran, an acidic catalyst and a nucleophilic initiator compound. The polyether compounds comprise m units of residue (1), n units of residue (2), and p units of residue (3) wherein (i) residues (1), (2) and (3) have the structures: ##STR1## (ii) the total value of m+n+p is 5 to 70; (iii) the value of n/(m+n+p) is in the range of 0.2 to 0.4, i.e.
Type:
Grant
Filed:
November 13, 1995
Date of Patent:
July 16, 1996
Assignee:
Eastman Chemical Company
Inventors:
James C. Matayabas, Jr., Peter B. MacKenzie, John A. Hyatt
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:
March 3, 1995
Date of Patent:
July 16, 1996
Assignee:
Eastman Chemical Company
Inventors:
James C. Matayabas, Jr., Stephen N. Falling
Abstract: Disclosed is a process for the preparation of 2,3-dihydrofurans from the corresponding isomeric 2,5-dihydrofurans wherein a feed mixture comprising a 2,5-dihydrofuran compound and an aldehyde selected from alkanals containing 2 to 5 carbon atoms and alkenals containing 3 or 4 carbon atoms, an epoxide selected from 1,2-epoxyalkanes containing 2 to 5 carbon atoms and 3,4-epoxy-1-butene, or a mixture of 2 or more of such aldehydes or epoxides and, optionally, carbon monoxide is contacted with a supported, palladium or platinum catalyst to effect the isomerization of 2,5-dihyrofurans to 2,3-dihydrofurans.
Abstract: Disclosed is an improved process for the preparation of 1,4-butenediol by the hydrolysis of 3,4-epoxy-1-butene (EpB) wherein a mixture of EpB and water is contacted with a catalyst comprising a catalyst support material an copper in a positive valence state.
Abstract: Disclosed is a method for treating asbestos to minimize the formation of airborne particulate of asbestos by applying to the asbestos an aqueous composition containing certain water-dispersible polymers. The method is especially useful when used in conjunction with the removal of asbestos from asbestos-coated objects.
Abstract: Disclosed is a process for the preparation of cyclopropanecarboxylic acid by the non-catalytic, oxidation of cyclopropanecarboxaldehyde using molecular oxygen as the oxidant. Also disclosed are processes for the preparation of amides, esters and acid chlorides from cyclopropanecarboxylic acid.
Abstract: Disclosed is an improved process for the preparation of alpha-tocopherol by the hydroxymethylation followed by the hydrogenation of non-.alpha.-tocopherols comprising .beta.-, .gamma.-, and .delta.-tocopherols using a particular palladium on alumina catalyst wherein (1) the dispersion and depth of deposition of the palladium metal are within certain ranges, and (2) the alumina is of a particular crystalline phase.
Type:
Grant
Filed:
August 17, 1995
Date of Patent:
April 2, 1996
Assignee:
Eastman Chemical Company
Inventors:
Yeong J. Kuo, Gary W. Hartley, Bruce L. Gustafson, David J. Allen
Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of tetrahydrofuran, an acidic catalyst and a nucleophilic initiator compound. The polyether compounds comprise m units of residue (1), n units of residue (2), and p units of residue (3) wherein (i) residues (1), (2) and (3) have the structures: ##STR1## (ii) the total value of m+n+p is 5 to 70; (iii) the value of n/(m+n+p) is in the range of 0.2 to 0.4, i.e.
Type:
Grant
Filed:
November 25, 1994
Date of Patent:
March 26, 1996
Assignee:
Eastman Chemical Company
Inventors:
James C. Matayabas, Jr., Peter B. MacKenzie, John A. Hyatt
Abstract: Disclosed is a process for the removal of iodine, including I.sub.2, I.sup.- and iodine-containing organic compounds, from acetic acid or anhydride wherein an acetyl product stream comprising (i) acetic acid or acetic anhydride and (ii) iodine, one or more iodine-containing compounds or a mixture thereof is subjected to distillation in the presence of a packing material comprising iron, nickel, copper, or an alloy thereof.
Type:
Grant
Filed:
May 31, 1994
Date of Patent:
March 26, 1996
Assignee:
Eastman Chemical Company
Inventors:
Carl F. Fillers, Jerry A. Barron, Eric D. Middlemas
Abstract: Disclosed is a process for the preparation of cyclopropanecarboxaldehyde by the thermal isomerization of 2,3-dihydrofuran under superatmospheric pressure, e.g., at a temperature of about 300.degree. to 600.degree. C. and a pressure of about 3 to 345 bars absolute.
Type:
Grant
Filed:
February 21, 1995
Date of Patent:
March 26, 1996
Assignee:
Eastman Chemical Company
Inventors:
Shaowo Liang, Timothy W. Price, Timothy R. Nolen, Daniel B. Compton, David C. Attride
Abstract: Disclosed is a novel process for the preparation and separation of cyclopropanecarbonitrile (CPCN) from cyclopropropanecarboxaldehyde (CPCA) using a combination of three process steps. The process involves the steps of (1) reacting (CPCA) with hydroxylamine base in the presence of water to obtain CPCA oxime, (2) contacting the CPCA oxime of step (1) with formic acid to obtain CPCN, and (3) contacting the mixture comprising CPCN formed in step (2) with a base to obtain a mixture comprising an organic phase containing CPCN and an aqueous phase. The reactants and intermediates involved in each step are used within certain defined ratios.
Abstract: Disclosed in a process for the homogeneous, catalytic hydrogenation of epoxyalkenes and epoxycyclo-alkenes, especially conjugated .gamma.,.delta.-epoxyalkenes and 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.
Abstract: Disclosed is a process for the preparation of cyclopropylmethanol(hydroxymethylcyclopropane) by the hydrogenation of cyclopropanecarboxaldehyde in the presence of a cobalt or nickel catalyst.
Abstract: Disclosed is a process for the preparation of 4,4'-stilbenedicarboxylate esters by a 4-step process starting with an alkyl p-formylbenzoate and utilizing intermediate phosphite and phosphonate compounds. The steps comprise(1) preparing an alkyl p-(hydroxymethyl)benzoate by hydrogenating an alkyl p-formylbenzoate;(2) contacting the alkyl p-(hydroxymethyl)benzoate of step (1) with a trialkyl phosphite to obtain a phosphite ester compound having the formula: ##STR1## (3) contacting the phosphite ester of step (2) with a catalytic amount of iodine to rearrange the phosphite ester to the corresponding phosphonate ester;and(4) contacting the phosphonate ester compound of step (3) with an alkyl p-formylbenzoate in the presence of an alkali metal alkoxide and an inert solvent to obtain the dialkyl 4,4'-stilbenedicarboxylate.
Type:
Grant
Filed:
March 6, 1995
Date of Patent:
December 5, 1995
Assignee:
Eastman Chemical Company
Inventors:
Richard H. S. Wang, Carl A. Bryan, Jr., Bill A. Eller
Abstract: Disclosed is a process for the preparation of 4,4'-stilbenedicarboxylate esters by a 3-step process utilizing p-toluic acid, an alkyl p-formylbenzoate and a trialkyl phosphite. The steps comprise(1) preparing p-(chloromethyl)benzoic acid by chlorinating p-toluic acid with sulfuryl chloride in the presence of a free radical initiator and chlorobenzene or dichlorobenzene;(2) contacting the p-(chloromethyl)benzoic acid of step (1) with a trialkyl phosphite to obtain a phosphonate compound; and(3) contacting the phosphonate ester compound of step (2) with an alkyl p-formylbenzoate in the presence of an alkali metal alkoxide and an inert solvent to obtain the dialkyl 4,4'-stilbenedicarboxylate.
Abstract: Disclosed is a process for the removal of crotonaldehyde impurity from cyclopropanecarboxaldehyde by the selective, catalytic hydrogenation of crotonaldehyde to butyraldehyde followed by distillation of the butyraldehyde from the cyclopropanecarboxaldehyde.
Abstract: Disclosed is a process for the preparation of 2,5-dihydrofurans by the homogeneous, liquid phase isomerization of .gamma.,.delta.-epoxyalkene compounds wherein a .gamma.,.delta.-epoxyalkene compound is isomerized in an inert, organic solvent containing a catalytic amount of a soluble copper salt. The process is particularly useful for the conversion of 3,4-epoxy-1-butene to 2,5-dihydrofuran.