Chemical Research & Licensing Company

Catalytic Distillation Technologies

Petro-tex Chemical Corporation

Other

Denka Chemical Corporation

Robert P Arganbright

Lawrence A Smith, Jr

Dennis Hearn

Edward M Jones, Jr

John R Adams

Gary R Gildert

William G Bowman

James D Henery

Stone D Cooley

Bradley S Hearn

A process for the isomerization of mono-olefins in aliphatic hydrocarbon streams is carried out at 40 to 300&deg; F. under low hydrogen partial pressure in the range of about 0.1 psi to less than 70 psi at 0 to 350 psig in a distillation column reactor containing a hydrogenation catalyst which serves as a component of a distillation structure, such as supported PdO encased in tubular wire mesh. Essentially no hydrogenation of the mono-olefins occurs.

Olefin isomerization process

A process for the selective hydrogenation of the diolefins and acetylenic compounds in a olefin rich aliphatic hydrocarbon streams is disclosed wherein the selective hydrogenation is carried out at 40 to 300&deg; F. under low hydrogen partial pressure in the range of about 0.1 psi to less than 70 psia at 0 to 350 psig in a distillation column reactor containing a hydrogenation catalyst which serves as a component of a distillation structure, such as supported PdO encased in tubular wire mesh. Essentially no hydrogenation of the olefins occurs.

Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams

Acetals are produced from the reaction of aldehydes and alcohols, e.g. methylal by the reaction of methanol and formaldehyde, by the reaction in a reaction distillation column of the alcohol and aldehyde in the presence of a catalyst and the concurrent fractional distillation of the reaction mixture to separate the reaction products, water and acetal.

Process for making acetals

A process for the alkylation of benzene contained in a mixed refinery stream is disclosed wherein the refinery stream is first subjected to hydrogenation of higher olefins prior to alkylation of the benzene with selected types and quantities of lower olefins. Streams containing sulfur compounds may be pretreated by hydrodesulfurization. All of the process steps are advantageously carried out in distillation column reactors to take advantage of that mode of operation.

Process for the alkylation of benzene

Process for alkylation of benzene

An alkene skeletal isomerization process is employed in an integrated process for the production of tertiary ether, e.g., tertiary amyl methyl ether (TAME) from the reaction of isoamylenes (iC.sub.5.sup.= 's) with methanol in the presence of an acid cation exchange resin. A light naphtha from a fluid catalytic cracking unit is used as the source of the iC.sub.5.sup.= 's in a process which separates the C.sub.5 containing fraction from the light naphtha, selectively hydrogenates the di-olefins contained in the C.sub.5 containing fraction, reacts the iC.sub.5.sup.= 's contained in the C.sub.5 containing fraction with methanol to form TAME, separates the TAME from the unreacted materials as a product, separates methanol from the unreacted materials, isomerizes a portion of the nC.sub.5.sup.= 's to iC.sub.5.sup.= 's , for example using a zeolite or an alumina treated with methanol, and use of the isomerization product as feed for a TAME reactor.

Integrated process for the production of tame

Ethyl benzene is produced in a catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 50.degree. C. to 300.degree. C., using as the catalyst a mole sieve characterized as acidic by feeding ethylene to the catalyst bed while benzene is conveniently added through the reflux to result in a molar excess present in the reactor to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene and diethyl benzene in the bottoms. The bottoms are fractionated, the ethyl benzene recovered and the bottoms are contacted with benzene in the liquid phase in a fixed bed straight pass reactor under conditions to transalkylate the benzene thereby converting most of the diethyl benzene to ethyl benzene which is again separated and recovered.

Process for the preparation of ethyl benzene

The present invention is a method for removing nitrile contaminants from C.sub.5 streams. In particular, a C.sub.5 stream is washed in a countercurrent fashion with a mixture comprising 50% methanol and 50% water to extract the nitriles from the C.sub.5 hydrocarbons into the water-methanol mixture. Propionitrile removal is enhanced by the presence of the methanol in the solvent. An further embodiments include (1) a method for recovering methanol from the extract stream by hydrogenating the nitriles to form amines, converting the amines to ammonium salts by acid treatment and distilling out the methanol and (2) distilling out methanol/nitriles from the extract stream, admixing the methanol/nitriles with an alkane/alkene/ether stream then distilling the methanol out in a azeotrope with the alkane/alkenes while leaving the nitriles in the ether.

Method for removing contaminants from hydrocarbon streams

Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

Alkylation of organic aromatic compounds

Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.

An integrated two stage process for the production of isoolefin by the dehydration of isoalcohol and the synthesis of a corresponding ether, for example the production of methyl tertiary butyl ether by (a) feeding tertiary butyl alcohol to a first distillation column reactor into a feed zone; (b) concurrently in said first distillation column reactor (i) contacting said TBA with an acid ion exchange resin catalyst as a component of a distillation structure, at a temperature in the range of 165.degree. to 200.degree. F. to dissociate said tertiary butyl alcohol to the isobutene and water, characterized in that sufficient water is maintained in said distillation reaction zone to inhibit the reaction of the isobutene with itself to form dimers and (ii) separating isobutene and water by fractional distillation; (c) withdrawing isobutene as overheads; (d) withdrawing water and undehydrated isoalcohol as bottoms, and in the second stage feeding the recovered isobutene to a second distillation column reactor with methanol and concurrently reacting methanol and isobutene at the appropriate dilution to form a reaction mixture containing methyl tertiary butyl ether.

Two stage production of ether from tertiary alcohol

Aromatic compounds are alkylated in a combination reactor/distillation column comprising a vessel suitable for operating between 70.degree. C. and 500.degree. C. and from 0.5 to 20 atmospheres pressure; an inert distillation packing in the lower one-third of said vessel; solid acidic catalytic material such as zeolites or an acidic cation exchange resin supported in the middle one-third of said vessel; and inert distillation packing in the upper one-third of said vessel. A benzene inlet is located near the upper end of the vessel; an olefin inlet is juxtaposed with said solid acidic catalytic material; a bottoms outlet is positioned near the bottom of said vessel for removing said cumene and ethyl benzene; and an overhead outlet is placed at the top of said vessel for removing any unreacted benzene and olefin.

A process for the isomerization of butenes in a mixed hydrocarbon stream containing butene-1, butene-2 and small amounts of butadiene in which the mixed hydrocarbon stream is fed to distillation column reactor containing an alumina supported palladium oxide catalyst as a distillation structure. As butene-1 is produced it is distilled off upsetting the equilibrium and allowing for a greater than equilibrium amount of butene-1 to be produced. Additionally, any butadiene in the feed is hydrogenated to butenes. The bottoms, which is rich in butene-2 may be recycled to the reactor column for more complete conversion of butene-2 to butene-1. Alternatively, a portion or essentially all of the bottoms, substantially free of butadiene, may be used for feed to an HF alkylation unit.

Hydroisomerization process

Cumene is produced in a catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 50.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic by feeding propylene to the catalyst bed while benzene is conveniently added through the reflux to result in a molar excess present in the reactor to that required to react with propylene, thereby reacting substantially all of the propylene and recovering benzene as the principal overhead and cumene and diisopropyl benzene in the bottoms. The bottoms are fractionated, the cumene recovered and the bottoms are contacted with benzene in the liquid phase in a fixed bed straight pass reactor under conditions to transalkylate the benzene thereby converting most of the diisopropyl benzene to cumene which is again separated and recovered.

Process for the preparation of cumene

A process for the production of tertiary alcohols by the reaction of the corresponding isoolefin and water is disclosed. In particular the production of tertiary butyl alcohol and tertiary amyl alcohol is disclosed. The isoolefin and water are contacted over an acid cation exchange resin catalyst in a distillation column reactor where the products and reactants are separated by fractional distillation. In one embodiment a liquid level is maintained in the catalyst bed.

Growing community of inventors

Seabrook, TX, United States of America

Robert P Arganbright