Uop Lcc

Boreskov Institute of Catalysis

Battelle Memorial Institute

Lanzatech, Inc.

Chinese Academy of Sciences

Dalian Institute of Chemical Physics

Joseph A Kocal

John Qianjun Chen

Kurt M Vanden Bussche

Alakananda A Bhattacharyya

Tamotsu Imai

Paul T Barger

Maureen L Bricker

Matthew Lippmann

Tom N Kalnes

Timothy A Brandvold

Stanley Joseph Frey

Peter K Coughlin

Vasant P Thakkar

James A Johnson

Michael J McCall

Joel T Walenga

Paul J Kuchar

Nina I Kuznetsova

Bair S Bal'zhinimaev

Nikolay Y Adonin

Anil Rajaram Oroskar

Manuela Serban

David C Martindale

Stanley A Gembicki

Christopher P Nicholas

Christopher D Gosling

Beckay J Mezza

Richard Russell Rosin

Richard E Marinangeli

Karthikeyan Kallupalayam Ramasamy

Mond Guo

Warren K Bennion

Terry L Marker

Jennifer S Holmgren

Tao Zhang

Tai-Hsiang Chao

Harold U Hammershaimb

Aiqin Wang

Mingyuan Zheng

Michael W Schoonover

Masami Kojima

Jifeng Pang

Irina Galperin, Legal Representative

Changzhi Li

Michael J Mccall

Deng-Yang Jan

Santi Kulprathipanja

Gregory John Lewis

Gavin Paul Towler

Robert R Frame

Paula L Bogdan

Jeffery C Bricker

Laurence O Stine

Gregory A Funk

Leonid B Galperin

Francis Stephen Lupton

Lisa M King

Simon H Hobbs

Feng Xu

Amarendra Anumakonda

James F Himes

Jeffrey C Bricker

Donald J Korous

Robert J Cornish

Disclosed herein are embodiments of a method and system for converting ethanol to para-xylene. The method also provides a pathway to produce terephthalic acid from biomass-based feedstocks. In some embodiments, the disclosed method produces p-xylene with high selectivity over other aromatics typically produced in the conversion of ethanol to xylenes, such as m-xylene, ethyl benzene, benzene, toluene, and the like. And, in some embodiments, the method facilitates the ability to use ortho/para mixtures of methylbenzyaldehyde for preparing ortho/para xylene product mixtures that are amendable to fractionation to separate the para- and ortho-xylene products thereby providing a pure feedstock of para-xylene that can be used to form terephthalic anhydride and a pure feedstock of ortho-xylene that can be used for other purposes, such as phthalic anhydride.

Method and system embodiments for converting ethanol to para-xylene and ortho-xylene

A solid terephthalic acid composition and a process for producing terephthalic acid from para-xylene. The process comprises forming a mixture comprising the para-xylene, a solvent, a bromine source, and a catalyst; and oxidizing the para-xylene by contacting the mixture with an oxidizing agent at oxidizing conditions to produce a solid oxidation product comprising terephthalic acid, para-toluic acid, 4-carboxybenzaldehyde. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms and an dialkyl imidazolium ionic liquid; and the catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium. The solid terephthalic acid composition comprises, less than about 4,000 ppm-wt 4-carboxybenzaldehyde content, and more than about 2,000 ppm-wt a para-toluic acid.

Process for producing terephthalic acid

A process for transalkylating a coal tar stream is described. A coal tar stream is provided, and is fractionated to provide at least one hydrocarbon stream having polycyclic aromatics. The hydrocarbon stream is hydrotreated in a hydrotreating zone, and then hydrocracked in a hydrocracking zone. A light aromatics stream is added to the hydrocracking zone. The light aromatics stream comprises one or more light aromatics having a ratio of methyl/aromatic available position that is lower than a ratio of methyl/aromatic available position for the hydrotreated stream. The hydrocracked stream is transalkylated in the hydrocracking zone.

Hydrocracking process for a hydrocarbon stream

A process for providing aromatics from a coal tar stream. A coal tar stream is provided, and the coal tar stream is fractionated into at least a naphtha range stream. The naphtha range stream is hydrotreated, and the hydrotreated naphtha range stream is separated to provide at least a naphthene rich stream. The naphthene rich stream is reformed or dehydrogenated to convert the naphthene. The dehydrogenated naphthene rich stream may be combined with a portion of a reformed crude oil hydrocarbon stream.

Process for providing aromatics from coal tar

A process for selectively dealkylating aromatic compounds includes providing a coal tar stream comprising aromatic compounds and hydrotreating the coal tar stream to reduce a concentration of one or more of organic sulfur, nitrogen, and oxygen in the coal tar stream, and to hydrogenate at least a portion of the aromatic compounds in the coal tar stream. The process further includes hydrocracking the hydrotreated coal tar stream to further hydrogenate the aromatic compounds and to crack at least one ring of multi-ring aromatic compounds to form single-ring aromatic compounds. The single-ring aromatic compounds present in the hydrocracked stream are then dealkylated to remove alkyl groups containing two or more carbon atoms.

Process for selectively dealkylating aromatic compounds

A process for pyrolyzing a coal feed is described. A coal feed is pyrolyzed into a coal tar stream and a coke stream in a pyrolysis zone. The coal tar stream is separated into at least a pitch stream comprising aromatic hydrocarbons. The pitch stream is reacted in a reaction zone to add at least one functional group to an aromatic ring of the aromatic hydrocarbons in the pitch stream. The functionalized pitch stream is recycled to the pyrolysis zone.

Process for pyrolysis of a coal feed

A process for producing alkylated aromatic compounds includes pyrolyzing a coal feed to produce a coke stream and a coal tar stream. The coal tar stream is hydrotreated and the resulting hydrotreated coal tar stream is cracked. A portion of the cracked coal tar stream is separated to obtain a fraction having an initial boiling point in the range of about 60&#xb0; C. to about 180&#xb0; C., and an aromatics-rich hydrocarbon stream is extracted by contacting the fraction with one or more solvents. The aromatics-rich hydrocarbon stream is contacted with an alkylating agent to produce an alkylated aromatic stream, or the aromatics-rich hydrocarbon stream is reacted with an aliphatic compound or methanol in the presence of a catalyst to produce a methylated aromatic stream. The alkylated aromatic stream, the methylated aromatic stream, or both are separated into at least a benzene stream, a toluene stream, and a xylenes stream.

Process for producing alkylated aromatic compounds

A process and a mixture for oxidizing an alkyl-aromatic compound comprises forming a mixture comprising the alkyl-aromatic compound, a solvent, a bromine source, and a catalyst; and contacting the mixture with an oxidizing agent at oxidizing conditions to produce an oxidation product comprising at least one of an aromatic aldehyde, an aromatic alcohol, an aromatic ketone, and an aromatic carboxylic acid. The solvent comprises a carboxylic acid having from 1 to 7 carbon atoms and an ionic liquid selected from the group consisting of an imidazolium ionic liquid, a pyridinium ionic liquid, a phosphonium ionic liquid, a tetra alkyl ammonium ionic liquid, and combinations thereof. The catalyst comprises at least one of cobalt, titanium, manganese, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, and zirconium.

Mixtures used in oxidizing alkyl aromatic compounds

Processes for producing reduced acid lignocellulosic-derived pyrolysis oil are provided. In a process, lignocellulosic material is fed to a heating zone. A basic solid catalyst is delivered to the heating zone. The lignocellulosic material is pyrolyzed in the presence of the basic solid catalyst in the heating zone to create pyrolysis gases. The oxygen in the pyrolysis gases is catalytically converted to separable species in the heating zone. The pyrolysis gases are removed from the heating zone and are liquefied to form the reduced acid lignocellulosic-derived pyrolysis oil.

Processes for converting lignocellulosics to reduced acid pyrolysis oil

Process for oxidizing alkyl aromatic compounds

Growing community of inventors

Gurnee, IL, United States of America

Joseph A Kocal