Eastman Chemical Company

Other

Shaowo Liang

Timothy W Price

John Robert Monnier

Daniel Latham Terrill

David Carl Attride

Stanley John Okrasinski

Yao-Ching Liu

Timothy Richard Nolen

Daniel Burts Compton

Colin Henry Ridyard

Clyde Neil Clubb

This invention pertains to a process for the preparation of 2,5-dihydrofurans by the isomerization of &ggr;,&dgr;-epoxyalkenes in the presence of a catalyst system comprising an organotin compound and an alkali metal iodide.

Process for the production of 2,5-dihydrofuran

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.

Processes for the preparation of cyclopropanecarboxylic acid and derivatives thereof

Disclosed is a process for the production of cyclopropanecarbonitrile (CPCN) by feeding concurently cyclopropanecarboxaldehyde (CPCA) and hydroxylamine aqueous solution to a reaction zone which contains formic acid. The process avoids the formation and accumulation of large amounts CPCA oxime intermediates which exhibit a very high energy release upon thermal decomposition. Additional embodiments of the invention comprise the steps of (1) synthesizing CPCN by feeding concurrently CPCA and hydroxylamine aqueous solution to a reaction zone containing formic acid to form a reaction product mixture comprising CPCN and (2) isolating and recovering the CPCN by contacting the reaction product mixture with a base to obtain a mixture comprising an organic phase containing CPCN and an aqueous phase. The removal of an azeotrope vapor comprising CPCN, water and a minor amount of formic acid from the reaction product mixture reduces the amount of formic acid consumed in the process as well as the amount of formate salts generated by the process.

Process for the manufacture of cyclopropanecarbonitrile

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.

Process for the production of cyclopropylmethyl halides

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.

Process for the production of cyclopropanemethylamine

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.

Process for the production of cyclobutyl halides

Processes for the preparation of cyclopropanecarboxylic acid and

Disclosed is a process for the conversion of off-color cyclopropanecarboxylic acid (CPC-Acid) to CPC-Acid having a color value (platinum-cobalt scale) of less than about 10 by the steps of (1) heating off-color CPC-Acid produced by the oxidation of cyclopropanecarboxaldehyde with molecular oxygen with a strong acid; and (2) distilling the mixture of step (1) to obtain CPC-Acid having a color value of less than about 10 as the distillate product.

Process for decolorizing cyclopropanecarboxylic acid

Disclosed is a process for the preparation of cyclopropanecarboxaldehyde by the isomerization of 2,3-dihydrofuran wherein 2,3-dihydrofuran is contacted with a catalyst selected from alumina, silica-alumina, silica, zirconia, titania and mixtures thereof having a nitrogen BET surface area of about 10 to 350 square meters per gram at elevated temperature.

Process for the conversion of 2,3-dihydrofuran to

Disclosed is a process for the removal of organic chlorides from furan and hydrogenated furans by contacting a crude product stream comprising (i) furan, 2,3-DHF, 2,5-DHF, THF or a mixture thereof and (ii) one or more organic chlorides with a copper-containing scavenger material.

Process for the removal of organic chlorides from furan and hydrogenated

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.

Process for the preparation and separation of cyclopropanecarbonitrile

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.

Process for the production of cyclopropanecarboxaldehyde

Disclosed is a process for the preparation of cyclopropylmethanol(hydroxymethylcyclopropane) by the hydrogenation of cyclopropanecarboxaldehyde in the presence of a cobalt or nickel catalyst.

Process for the preparatoin of cyclopropylmethanol

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.

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Kingsport, TN, United States of America

Shaowo Liang