Exxonmobil Chemical Patents Inc.

Charles Morris Yarbrough

Jane C Cheng

Ramzi Yanni Saleh

Raphael Frans Caers

David Wayne Turner

Dennis Jay Davoren

Carolyn B Duncan

Stephen Harold Brown

Doron Levin

Vijay Swarup

John Stephen Godsmark

Eddy Theophile Van Driessche

Hubertus Joseph Beckers

Arie Van Vliet

Carl Robert Beck

James L Propp

Yeo-Meng Lim

Jean-Jacques G Muls

James C Vartuli

Jon E Stanat

Allen David Godwin

Shifang Luke Luo

Georges M K Mathys

Seth McConkie Washburn

Dane Clark Grenoble

Georges Marie Karel Mathys

Stephen Wayne Beadle

Hans Georg Korsten

Michael Alan Better

Roger Eijkhoudt

Michael Walter Bedell

Patrick Joseph Maher

Kenneth Joseph Buturla

Ernest E Green

Albert Y Hu

Paul E Burton

Brian William Roberts

Cesar M Cheng Guajardo

George Marie Karel Mathys

John P Motlow

Timothy P Dean

Ky I Tanner

Carl Stotz Katzenstein

The invention is directed to improvements in the indirect hydration process for the production of alcohols that enable high alcohol yield by increasing ether recycle in an olefin hydration process, such as the hydration process to produce isopropyl alcohol (IPA) from propylene or the hydration process to produce sec-butyl alcohol (SBA) from butylene.

Olefin hydration process

A process for the oligomerization of olefins includes treating, e.g., water washing, an olefin-containing hydrocarbon stream to lower the concentration of an organic nitrogen-containing Lewis base contained therein until the treated hydrocarbon stream is substantially free of the Lewis base; and subsequently contacting the treated hydrocarbon stream with a molecular sieve catalyst to produce a product including at least one oligomer.

Lowering nitrogen-containing Lewis bases in molecular sieve oligomerisation

Embodiments of the invention disclosed herein relate to a process for the production of a C-Calcohol mixture comprising the steps of: hydroformylating an olefin mixture comprising a branched C-Colefin to form a hydroformylation product comprising aldehydes and formate esters, whereby the hydroformylation product has a net cold sap number from 15 to 38 mg KOH/g, and converting the aldehydes and formate esters to alcohols in a hydrogenation step comprising at least one first hydrogenation reactor comprising a fixed bed of a heterogeneous sulphided bimetallic catalyst.

Plasticiser alcohol and production improvement

An alkylaromatic hydrocarbon composition prepared by the process which comprises oligomerizing an olefin selected from the group consisting of propylene, n-butene and mixtures thereof over an oligomerization catalyst, to form a oligomerization product comprising at least 95% by weight of mono-olefin oligomers of the empirical formula:CHwherein n is greater than or equal to 10, the mono-olefin oligomers comprise at least 20% by weight of olefins having at least 12 carbon atoms, and the olefins having at least 12 carbon atoms having an average of from 0.8 to 2.0 C-Calkyl branches per carbon chain. Sulfonation of the alkylaromatic hydrocarbon product produces an alkylaryl sulfonate mixture that exhibits advantageous properties, such as biodegradability and hard and cold water performance.

Preparation of alkylaromatic hydrocarbons and alkylaryl sulfonates

Oxo-alcohols in the plasticizer range typically contain small amounts of methyl esters having the same alkyl chain as the alcohol itself. These methyl esters are causing product quality problems and environmental problems because of transesterification in the esterification process where the plasticizer ester derivatives are produced. A process using controlled oxonation and hydrogenation conditions is disclosed for the production of alcohols containing low amounts of methyl esters. Plasticizer esters with low amounts of aliphatic di-alkyl esters are also disclosed.

Nitrogen-containing Lewis bases act as poisons for molecular sieve catalysts used in oligomerisation reactions. A lowering of their presence in the feed prior to the contacting thereof with the molecular sieve brings a significant extension of catalyst life. Excessive elimination of these poisons may be disadvantageous. Lowering the levels of these catalyst poisons to more manageable concentrations is therefore preferred.

This invention relates to a method of making an olefin from a dialkyl ether comprising (a) introducing an ether having a formula CHCHinto a thermal or catalytic cracking unit processing a hydrocarbon feedstock; and (b) decomposing at least a portion of the ether to form an olefin having a formula CHand/or CHand an alcohol having a formula CHand/or CHOH, wherein x and y independently range from about 1 to about 30. This invention also relates to a method of reducing coking in a thermal or catalytic cracking unit comprising (a) introducing an ether, having a formula CHOCH, into the cracking unit processing a hydrocarbon feedstock in an amount effective to reduce coke formation relative to processing the hydrocarbon feedstock in the absence of the ether, wherein x and y independently range from about 1 to about 30.

Method for decomposition of ethers

In a process for preparing an alkylaromatic hydrocarbon composition an olefinic hydrocarbon mixture and an aromatic compound are contacted under alkylation conditions with an aromatic alkylation catalyst selected from a homogeneous acid catalyst and heterogeneous acid catalyst comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4&#xb1;0.25, 6.9&#xb1;0.15, 3.57&#xb1;0.07 and 3.42&#xb1;0.07 Angstroms. The olefinic hydrocarbon mixture comprises at least 5 wt % by weight of mono-olefin oligomers of the empirical formula:CHwherein n is greater than or equal to 10, the mono-olefin oligomers comprising at least 20 percent by weight of olefins having at least 12 carbon atoms, and the olefins having at least 12 carbon atoms having an average of from 0.8 to 2.0 C-Calkyl branches per carbon chain. Sulfonation of the alkylaromatic hydrocarbon product produces an alkylaryl sulfonate mixture that exhibits advantageous properties, such as biodegradability and hard and cold water performance.

A selectivated molecular sieve, e.g., ZSM-22 or ZSM-23, is used as olefin oligomerization catalyst to provide product, e.g., octenes and dodecenes from butene, having a low degree of branching and hindered double bonds.

Oligomerization of olefins

This invention relates to a process for the production of an alcohol, the process comprising (a) reacting an olefin and water in the presence of a catalyst under conditions sufficient to form a crude alcohol stream comprising alcohol, and a dialkyl ether; (b) separating at least a portion of the crude alcohol stream into an alcohol-containing stream and a dialkyl ether stream; (c) contacting at least a portion of the dialkyl ether stream with an ether decomposition catalyst, the ether decomposition catalyst comprising a mixed metal oxide having the following composition XYZOwhere X is at least one metal selected from Group 4 of the Periodic Table of Elements, Y is at least one metal selected from Group 3 (including the Lanthanides and Actinides) and Group 6 of the Periodic Table of Elements and Z is at least one metal selected from Groups 7, 8, and 11 of the Periodic Table of Elements; m, n, p, and q are the atomic ratios of their respective components and, when m is 1, n is from about 0.01 to about 0.75, p is from 0 to about 0.1, and q is the number of oxygen atoms necessary to satisfy the valence of the other components, to form a crude dialkyl ether decomposition stream comprising alcohol and olefin; (d) recovering at least a portion of the olefin from the crude dialkyl ether decomposition stream; and (e) recycling at least a portion of the olefin recovered in step (d) to step (a).

Process for alcohol production by selective ether decomposition

A process for selectively converting a dialkyl ether to the corresponding alkene and alkanol comprises contacting a feed containing at least one dialkyl ether with a catalyst comprising a mixed metal oxide which comprises at least one metal selected from Group 4 of the Periodic Table of Elements and at least one metal selected from Group 3 (including the Lanthanides and Actinides) and Group 6 of the Periodic Table of Elements.

Selective decomposition of ethers

A process is disclosed for forming a vinyl ester from a carboxylic acid and acetylene in the presence of a zinc carboxylate catalyst, wherein a mixture of carboxylic acid and zinc carboxylate catalyst is formed and the water content of the mixture is reduced to between about 0.02 wt. % and about 0.3 wt. %, prior to introduction of the acetylene into the reactor. Optionally, water is introduced into the reactor during the reaction to hydrate any anhydride by-product of the reaction present in the reactor to carboxylic acid reactant. Water is added during the reaction in an amount that is sufficient to convert the anhydride by-product to carboxylic acid reactant, but does not raise the amount of water in the reaction mixture to a level that will reduce the reactivity of the catalyst or reduce the rate of the vinylation reaction.

Process for forming vinyl ester from carboxylic acid with water treatment of the reaction mixture

A process for producing high purity isopropyl alcohol. In one embodiment, the process includes the steps of: (a) feeding a feed stream comprising at least about 99.9 wt. % isopropyl alcohol into a separation column; (b) separating the isopropyl alcohol into an overhead stream taken overhead from the separation column and a bottoms stream taken as bottoms from the separation column; and (c) removing the high purity isopropyl alcohol at a point: (i) below where the feed stream enters the separation column but above the bottoms stream, or (ii) above where the feed stream enters the separation column but below the overhead stream. The high purity isopropyl alcohol has a metals content of less than about 1 ppb and a water content of less than about 100 ppm. Optionally, the process includes the step of passing the high purity isopropyl alcohol through an ion exchange resin after removing the high purity isopropyl alcohol from the separation column, thereby forming an ultra-high purity isopropyl alcohol that contains less than 100 ppt of any metal impurity.

Process for producing ultra-high purity isopropanol

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Baton Rouge, LA, United States of America

Charles Morris Yarbrough