Exxonmobil Chemical Patents Inc.

Georgia Tech Research Corporation

Exxonmobil Research and Engineering Company

Virginia Tech Intellectual Properties Inc.

Michael Salciccioli

Jihad Mohammed Dakka

Neeraj Sangar

Michael W Weber

Scott Jeffrey Weigel

Alan Anthony Galuska

Lorenzo C DeCaul

Ali A Kheir

Gaurav Agrawal

Doron Levin

Hari Nair

Dana Lynn Pilliod

Michel Molinier

Kapil Kandel

Stephen Todd Cohn

Monica D Lotz

Meha Rungta

Emiel De Smit

Ranjita Ghose

Aaron B Pavlish

Paul F Keusenkothen

Gary David Mohr

Terry Eugene Helton

Stephen Zushma

Tan-Jen Chen

Chuansheng Bai

John Roger Porter

Bryan A Patel

Victor DeFlorio

Michael P Lanci

Javier Guzman

Glenn C Wood

Yoshiaki Kawajiri

Edward E Paschke

Joshua W Allen

S Richard Turner

Siwei Guo

Jason Bentley

Jarid M Metz

Gregory J De Martin

Hans Eliot Edling

Keith Holroyd Kuechler

James Harding Beech, Jr

Christine Nicole Elia

Crisita Carmen H Atienza

John Frances Brody

Sumathy Raman

Timothy Paul Bender

Mosha H Zhao

Nikolaos Soultanidis

Catherine M Dorsi

Mary T Van Nostrand

James J Tanke

Bifuran-modified polyester, polyethylene-terephthalate-co (2,2′-bifuran-5,5′-dicarboxylate), prepared by esterifying or transesterifying a diacid component comprising from 2 to 10 mole percent 2,2′-bifuran-5,5′-dicarboxylate and a diol component with a catalyst compound comprising metal present in an amount of from about 10 to about 450 ppm and polycondensation to form the polyester wherein the polyester has an inherent viscosity of at least 0.5 g/dL, a glass transition temperature (Tg) of 82° C. or more, a semicrystalline melting peak (Tm) with ΔHf equal to or greater than 5 J/g on the second heating ramp, and melting temperature (T) between 229° C. and 246° C. Reinforced compositions and shaped articles comprising bifuran-modified polyethylene terephthalate and methods of their production are also disclosed.

Bifuran-modified polyesters

A 5,5′-Di-(protected)-2,2′-bifuran: wherein each Ris independently an unsubstituted or substituted 5- or 6-member 1,3-dioxo-2-yl ring radical. Processes for making the bifuran include coupling 2-(protected)-furfural. Processes for using the bifuran include deprotection, functionalization, and/or polymerization to form a polyester. The polyester can be a renewable, high-performing polyester offering a combination of low cost of production, high sustainability, and excellent performance.

Functionalized bifuran and synthesis thereof

Semicrystalline polyethylene-2,2′-bifuran-5,5′-dicarboxylate (PEBF) homopolyester or copolyester with up to 5 mole percent isophthalate or up to 2.7 mole percent terephthalate, based on the diacid component, or up to 2.5 mole percent 1,4-cyclohexanedimethanol (CHDM), based on the diol component, prepared by esterifying or transesterifying the diacid and the diol components with a catalyst including about 10 to about 50 ppm wt metal, and polycondensation, wherein the bifuran polyester has an intrinsic viscosity of at least 0.4 g/dL and a semicrystalline melting peak (Tm) with ΔHf equal to or greater than 5 J/g on the second heating ramp.

Bifuran polyesters

A process and related system for producing para-xylene (PX). In an embodiment, the process includes (a) separating a feed stream comprising Caromatic hydrocarbons into a toluene containing stream and a Chydrocarbon containing stream and (b) contacting at least part of the toluene containing stream with a methylating agent in a methylation unit to convert toluene to xylenes and produce a methylated effluent stream. In addition, the process includes (c) recovering PX from the methylated effluent stream in (b) to produce a PX depleted stream and (d) transalkylating the PX depleted stream to produce a transalkylation effluent stream. The transalkylation effluent stream includes a higher concentration of toluene than the PX depleted stream. Further, the process includes (e) converting at least some ethylbenzene (EB) within the Chydrocarbon containing stream into toluene and (f) flowing the toluene converted in (e) to the contacting in (b).

Xylene production processes and systems

Alkyl-demethylation of C2+-hydrocarbyl substituted aromatic hydrocarbons can be utilized to treat one or more of a heavy naphtha reformate stream, a hydrotreated SCN stream, a C8 aromatic hydrocarbon isomerization feed stream, a C9+ aromatic hydrocarbon transalkylation feed stream, and similar hydrocarbon streams to produce additional quantity of xylene products.

Processes for converting aromatic hydrocarbons via alkyl-demethylation

Transalkylation processes for converting aromatic hydrocarbons comprising alkyl-demethylation

A process for producing phenylstyrene comprises contacting benzene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation product comprising cyclohexylbenzene. At least part of the cyclohexylbenzene is then contacted with ethylbenzene in the presence of a transalkylation catalyst under conditions effective to produce a transalkylation product comprising cyclohexylethylbenzene and/or with ethylene in the presence of an alkylation catalyst under conditions effective to produce an alkylation product comprising cyclohexylethylbenzene. At least part of the cyclohexylethylbenzene is then contacted with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation product comprising phenylstyrene.

Preparation and use of phenylstyrene

The process involves the use of two rotary valves to implement Varicol operation of a simulated moving bed apparatus to separate a product from at least one multicomponent feed. In a particular embodiment, paraxylene is separated from a mixture of C8 aromatic hydrocarbons. The use of the Varicol process further enhances the separation of the desired product and provides flexibility with a simulated moving bed apparatus using dual rotary valves.

Simulated moving bed separation process

Systems and methods are provided for forming para-xylene from aromatics-containing streams having reduced or minimized amounts of Cside chains. Reduced or minimized amounts of Cside chains can provide benefits for improving and/or allowing modification of transalkylation conditions, xylene isomerization conditions, or a combination thereof. Such aromatics-containing streams can be formed, for example, by conversion of methyl halide, methanol, syngas, and/or dimethyl ether to aromatics by an aromatic conversion process. The methyl halide, methanol, syngas, and/or dimethyl ether can be formed by conversion of methane.

Process for converting alkanes to para-xylene

A process to separate paraxylene from a mixture of paraxylene, metaxylene, orthoxylene, and ethylbenzene in a commercial simulated moving bed apparatus in a reduced number of beds is provided, allowing an additional separation to be conducted in the remaining beds. This additional separation may separate another xylene isomer, ethylbenzene, or a non-aromatic Chydrocarbon from the raffinate stream produced by the first separation. A PowerFeed process is used to recover paraxylene in a first adsorption zone containing 8-16 beds of a conventional 24-bed simulated moving bed adsorption apparatus, and then a second separation may be conducted in a second adsorption zone containing the remaining beds.

Xylene separation process

Disclosed is a process for recovering paraxylene in which a first simulated moving bed adsorption unit is used to produce two extract streams&#x2014;one rich in paraxylene and a paraxylene-rich extract stream that is lean in ethylbenzene and an ethylbenzene-rich extract stream that is lean in paraxylene- and a paraxylene-depleted raffinate stream. A significant amount of the ethylbenzene is removed in the ethylbenzene-rich extract stream (at least enough to limit buildup in the isomerization loop), so the paraxylene-depleted raffinate stream may be isomerized in the liquid phase. Avoiding vapor phase isomerization saves energy and capital, as liquid phase isomerization requires less energy and capital than the vapor phase isomerization process due to the requirement of vaporizing the paraxylene-depleted stream and the use of hydrogen, which requires an energy and capital intensive hydrogen recycle loop.

Processes for recovering paraxylene

A process for selective oxidation of dimethyl-1,1'-biphenyl to form methyl-1,1&#x2032;-biphenyl mono-carboxylic acid(s), comprising contacting a solution of dimethyl-1,1&#x2032;-biphenyl in acetic acid solvent in the presence of a Co(II) acetate catalyst and air, and optionally adding a co-solvent, or adding sodium or potassium acetate, and oxidizing the dimethyl-1,1&#x2032;-biphenyl under time and temperature conditions sufficient to form one or more methyl-1,1&#x2032;-biphenyl mono-carboxylic acid(s). The mono-carboxylic acids are advantageously isolated and esterified to form biphenyl mono-esters for use as plasticizers.

Selective aerobic oxidation of dimethylbiphenyls

A process for selective oxidation of dimethyl-1,1'-biphenyl(s) to form methyl-1,1&#x2032;-biphenyl mono-carboxylic acid(s), which can be esterified to form plasticizers, comprising contacting a solution of dimethyl-1,1&#x2032;-biphenyl(s) in acetic acid in the presence of an oxidation catalyst and air under time and temperature conditions sufficient to oxidize the dimethyl-1,1&#x2032;-biphenyl(s) into one or more methyl-1,1&#x2032;-biphenyl mono-carboxylic acid(s) products, conducting at least one of (i) adding an antisolvent, or (ii) optimizing a total conversion of dimethyl-1,1&#x2032;-biphenyl(s) by oxidation based upon a molar ratio of dimethyl-1,1&#x2032;-biphenyl isomers, or (iii) precipitating the methyl-1,1&#x2032;-biphenyl mono-carboxylic acid(s) products by lowering the temperature, or (iv) decreasing the oxidation reaction temperature to enhance conversion of aldehydes over methyl functional groups, so as to limit over-oxidation of the dimethyl-1,1&#x2032;-biphenyl(s), wherein the oxidation reaction is conducted in the absence of bromide-containing catalysts.

Systems and methods are provided for converting alkane while generating improved yields of desirable aromatics and/or improved selectivity for forming desired aromatics, such as para-xylene (p-xylene). Aromatics generated during the aromatic formation process can be alkylated to form xylenes with improved yield and/or improved selectivity.

Conversion of non-aromatic hydrocarbon

Processes for selectively alkylating and/or dealkylating one ring of cyclohexylbenzyl and/or biphenyl compounds are provided. Such selective alkylation and/or dealkylation takes place through a transalkylation reaction between the cyclohexylbenzyl compound and a substituted or unsubstituted benzene, which replaces the phenyl moiety of the cyclohexylbenzyl compound. The transalkylated cyclohexylbenzyl may be dehydrogenated to give a corresponding biphenyl compound. The same reaction steps can be utilized with respect to biphenyl compounds by first partially hydrogenating one phenyl ring of the biphenyl compound, thereby obtaining a corresponding cyclohexylbenzyl compound, which may undergo the transalkylation and, optionally, subsequent dehydrogenation. Combinations of any two or more of partial hydrogenation, transalkylation, and dehydrogenation enable targeted substitution (or de-substitution) of only one ring of cyclohexylbenzyl and/or biphenyl compounds, thereby providing superior control in designing the synthesis of these compounds.

Transalkylated cyclohexylbenzyl and biphenyl compounds

Growing community of inventors

Houston, TX, United States of America

Michael Salciccioli