Exxonmobil Chemical Patents Inc.

Exxonmobil Research and Engineering Company

Jörg F W Weber

Christopher Lynn Becker

Jason D Davis

Ashley J Malik

Kendele S Galvan

Kirk C Nadler

Ashley J Poucher

Jihad Mohammed Dakka

Heinrich R Braun

Behrouz Engheta

Tobias Klande

Keith Holroyd Kuechler

Tan-Jen Chen

Andrew Edmund Taggi

Shuji Luo

Helge Jaensch

Kevin John Kelly

Seth McConkie Washburn

Jose M Vargas

Gary Christensen

Jonathan J Watts

Andrew R Witt

Amy B Batton

Wenyih Frank Lai

Stephen Zushma

Neeraj Sangar

Kyle G Lewis

Patrick C Chen

Jennifer L Rapp

Anatoly Ilich Kramer

Babak LotfizadehDehkordi

Renyuan Yu

Mika L Shiramizu

James Oliver Meredith

Medrado M Leal

Methyl paraffins formed by hydrogenating one or more LAO dimers comprising a vinylidene moiety or a trisubstituted olefin moiety may have advantageous heat transfer properties, particularly when incorporated within an electric vehicle. For example, methyl paraffins produced upon hydrogenating LAO dimers formed from one or more C-CLAOS, particularly in the presence of a Hf metallocene catalyst system, may contain 12-24 carbon atoms, and collectively have a flash point of about 130° C. or above, a pour point of about −42° C. or lower, a thermal conductivity at 80° C. of about 0.165 W/m·K or higher, and a Mouromtseff number ranging from about 17,000 to about 27,000 kg/(s·m·K) at 80° C. Heat transfer fluids comprising such methyl paraffins may be placed in contact with a heat-generating component, such as a battery and/or motor of an electric vehicle, or within a similar type of battery system, including immersive configurations for a battery.

Heat transfer fluids comprising methyl paraffins derived from linear alpha olefin dimers and use thereof

Methylparaffins having limited methyl branching may be prepared by contacting at least one linear olefin with hydrogen in the presence of a dual-function supported catalyst comprising a solid acid component and a hydrogenation component under conditions sufficient to catalytically isomerize the at least one linear olefin into an intermediate product comprising one or more branched olefins, and hydrogenating the one or more branched olefins to form an isoparaffin product comprising one or more methylparaffins. Heat transfer fluids comprising such methylparaffins may be used in various thermal management systems, such as within various systems of electric vehicles, server farms, or other locales in need of efficient heat transfer.

Methylparaffins obtained through isomerization of linear olefins and use thereof in thermal management

Disclosed are novel processes for the production of cyclic imide compounds such as N-hydroxyphthalimide (NHPI). The processes may be particularly well-suited for commercial-scale production of cyclic imides such as NHPI. Such cyclic imide compounds are suitable for use as oxidation catalysts, and specifically may be used to oxidize cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide. Such an oxidation may be particularly useful in a process for the production of phenol and/or cyclohexanone from benzene via a process comprising hydroalkylation of benzene to cyclohexylbenzene, oxidation of the cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide, and cleavage of the cyclohexyl-1-phenyl-1-hydroperoxide to phenol and cyclohexanone. The cyclic imide production process may advantageously include water washing and reactant recovery steps to maximize purity and yield.

Production of cyclic imides suitable for oxidation catalysis

This disclosure relates to heat transfer fluids for use in heat transfer systems. The heat transfer fluids comprise at least one non-aqueous dielectric heat transfer fluid. The non-aqueous dielectric heat transfer fluid has density (&#x3c1;), specific heat (c), and dynamic viscosity (&#x3bc;) properties. The heat transfer fluids have a normalized effectiveness factor (NEF) as determined by the following equation: wherein DEFis a dimensional effectiveness factor for the heat transfer fluid that is determined based on an equation designated in Table 1 below for a selected pump and a selected heat transfer circuit dominant flow regime; wherein DEFis a dimensional effectiveness factor for a reference fluid that is determined using the same equation designated in Table 1 for DEFabove for the same selected pump and the same selected heat transfer circuit dominant flow regime; and wherein the heat transfer fluid has a NEFvalue equal to or greater than 1.0. This disclosure also provides a method for improving performance of a heat transfer system, a method for improving performance of an apparatus, and a method for selecting a heat transfer fluid for use in a heat transfer system. The heat transfer fluids and methods of this disclosure are applicable in situations where the heat transfer system is dominated by heat conveyance.

Heat transfer fluids and methods of use

Disclosed are a process for abating 3-cyclohexenone from a feed mixture comprising 3-cylclohexenone and cyclohexanone, comprising a hydrogenation step of contacting the feed mixture with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions to obtain a hydrogenated mixture, cyclohexanone-containing products comprising 3-cyclohexenone and/or 2-cyclohexenone at low concentrations, and compositions of matter useful for making such cyclohexanone-containing products, particularly by using such processes.

Cyclohexanone-containing products and processes for making the same

Disclosed are processes for abating 3-cyclohexenone from a feed mixture comprising cyclohexylbenzene, cyclohexanone, phenol, and 3-cyclohexenone and cyclohexanone, comprising feeding the feed mixture to a first distillation column and a hydrogenating a fraction from in the presence of a hydrogenation catalyst under hydrogenation conditions. Hydrogenation can be carried out in a hydrogenation reactor separate from the first distillation column or in a hydrogenation zone disposed inside the first distillation column.

Processes for making cyclohexanone

Disclosed are processes for making cyclohexanone from a feed mixture comprising cyclohexylbenzene, cyclohexanone, phenol, 3-cylclohexenone and optionally 2-cyclohexenone, comprising feeding the feed mixture to a first distillation column and hydrogenating a fraction from the first distillation column in a hydrogenation reactor separate from the first distillation in the presence of a hydrogenation catalyst under hydrogenation conditions. A cyclohexanone-rich upper effluent comprising 3-cyclohexenone and 2-cyclohexenone at low concentrations can be obtained from the first distillation column.

This disclosure relates to heat transfer fluids for use in heat transfer systems. The heat transfer fluids comprise at least one non-aqueous dielectric heat transfer fluid. The non-aqueous dielectric heat transfer fluid has density (&#x3c1;), specific heat (c), and dynamic viscosity (&#x3bc;) properties. The heat transfer fluids have a normalized effectiveness factor (NEF) as determined by the following equation:  wherein DEFis a dimensional effectiveness factor for the heat transfer fluid that is determined based on an equation designated in Table 1 below for a selected pump and a selected heat transfer circuit dominant flow regime; wherein DEFis a dimensional effectiveness factor for a reference fluid that is determined using the same equation designated in Table 1 for DEFabove for the same selected pump and the same selected heat transfer circuit dominant flow regime; and wherein the heat transfer fluid has a NEFvalue equal to or greater than 1.0. This disclosure also provides a method for improving performance of a heat transfer system, a method for improving performance of an apparatus, and a method for selecting a heat transfer fluid for use in a heat transfer system. The heat transfer fluids and methods of this disclosure are applicable in situations where the heat transfer system is dominated by heat conveyance.

Disclosed are processes for making such cyclohexanone compositions from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene. Such cyclohexanone compositions comprise at least 99 wt % cyclohexanone, at most 0.15 wt % water, and at most 500 wppm combined of certain cyclohexanone impurities selected from the group consisting of: benzene, cyclohexene, pentanal, cyclopentanol, cyclohexanol, and phenol.

Cyclohexanone compositions and processes for making such compositions

This disclosure relates to methods for producing purified aromatic esters useful as plasticizers, to the purified aromatic esters, and to polymer compositions containing the purified esters. The purified aromatic esters can be produced by esterifying carboxylic acid with methyl or ethyl alcohol, separating the resulting methyl or ethyl esters from the carboxylic acid and any byproduct impurities, and then transesterifying the methyl or ethyl esters with Cto Calcohol to produce the purified aromatic esters. Additionally, precipitation, filtration, and wash steps can be employed to purify the carboxylic acid, the methyl or ethyl alcohol, and/or the aromatic esters.

Purified plasticizers, production and use

In a process for separating a mixture comprising cyclohexanone and phenol, a solid-phase basic material, such as basic ion-exchange resin, is used to remove acid and/or sulfur from the mixture prior to separation. The process results in reduced amount of contamination such as cyclic ethers in the cyclohexanone and/or phenol products.

Process for making cyclohexanone and/or phenol

Disclosed is (i) a process of making phenol and/or cyclohexanone from cyclohexylbenzene including a step of removing methylcyclopentylbenzene from (a) the cyclohexylbenzene feed supplied to the oxidation step and/or (b) the crude phenol product (ii) a phenol composition and (iii) a cyclohexylbenzene composition that can be made using the process.

Cyclohexylbenzene composition

Disclosed are novel processes for making cyclohexanone compositions, from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene. The process includes hydrogenation of a feed stream comprising phenol, cyclohexanone, and cyclohexylbenzene. The feed stream may be subjected to one or more pre-hydrogenation treatments, such as passing through one or more sorbents, addition of basic chemical agents, and/or addition of water, so as to improve catalyst activity, minimize undesired side reactions, and/or remove catalyst poisons from the feed stream. The feed stream may be provided to a hydrogenation reaction zone in the vapor phase, with periodic alterations to hydrogenation reaction conditions such that the feed is provided in mixed liquid and vapor phase in order to carry out liquid washing of a hydrogenation catalyst bed within the hydrogenation reaction zone.

Growing community of inventors

Houston, TX, United States of America

Jörg F W Weber