GB1116037A - Preparation of mesityl oxide and/or methyl isobutyl ketone - Google Patents

Preparation of mesityl oxide and/or methyl isobutyl ketone

Info

Publication number
GB1116037A
GB1116037A GB2851366A GB2851366A GB1116037A GB 1116037 A GB1116037 A GB 1116037A GB 2851366 A GB2851366 A GB 2851366A GB 2851366 A GB2851366 A GB 2851366A GB 1116037 A GB1116037 A GB 1116037A
Authority
GB
United Kingdom
Prior art keywords
mesityl oxide
fraction
feed
acetone
mol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2851366A
Inventor
Lionel James Sirois
Frank Joseph Herrmann
Morey Edmond Oldweiler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to GB2851366A priority Critical patent/GB1116037A/en
Publication of GB1116037A publication Critical patent/GB1116037A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Mesityl oxide is prepared by continuously contacting an oxygenated hydrocarbon feed, which contains acetone, in the gas phase in a condensation zone with a catalyst consisting mainly of zinc oxide at a temperature of about 400 DEG to 800 DEG F., continuously withdrawing a product stream containing mesityl oxide from the condensation zone, cooling the product stream below 120 DEG F., separating a vaporous fraction containing substantial amounts of hydrogen, propylene and acetone and minor amounts of isopropanol, water, methylisobutyl ketone and mesityl oxide from a liquid fraction containing the remainder of the unreacted feed and reaction products, distilling this liquid fraction to recover a fraction rich in unreacted feed and a mesityl oxide-rich fraction, and recycling part of the vaporous fraction and unreacted-feed fraction to the condensation zone in such amounts that the recycled mesityl oxide does not exceed 0.5 mol. per cent of the total feed to the condensation zone. A preferred embodiment involves contacting the mesityl oxide-rich fraction with hydrogen in the presence of a hydrogenation catalyst, suitably nickel, to convert mesityl oxide to methyl isobutyl ketone, fractionating the effluent from the hydrogenation zone to separate methyl isobutyl carbinol, and recycling the methyl isobutyl carbinol and part of the vaporous fraction and unreacted feed fraction to the condensation zone under the same conditions with respect to molar percentage of mesityl oxide recycled. Products can be withdrawn at various stages of the process and can consist essentially of mesityl oxide, methyl isobutyl ketone or methyl isobutyl carbinol. The catalyst for the main reaction in the condensation zone is preferably 70-99% by weight of zinc oxide with 1-30% of a promoter which can be cerium, thorium or zirconium oxide. Preferred conditions in the condensation involve contacting acetone with the catalyst at a space velocity of 0.25 to 2 volumes of total feed per volume of catalyst per hour, in admixture with 0.01 to 1 mol. (or better, 0.01-0.04 mol.) of hydrogen per mol. of acetone at a temperature between 500 DEG and 800 DEG F. and pressure of 5 to 75 p.s.i.g. such that the conversion level of acetone to mesityl oxide is between 7 and 12%, wherein the vaporous fraction of the feed contains less than 0.3 mol. per cent of recycled mesityl oxide and the acetone-rich fraction not more than 0.2 mol. per cent of mesityl oxide.
GB2851366A 1966-06-24 1966-06-24 Preparation of mesityl oxide and/or methyl isobutyl ketone Expired GB1116037A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2851366A GB1116037A (en) 1966-06-24 1966-06-24 Preparation of mesityl oxide and/or methyl isobutyl ketone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2851366A GB1116037A (en) 1966-06-24 1966-06-24 Preparation of mesityl oxide and/or methyl isobutyl ketone

Publications (1)

Publication Number Publication Date
GB1116037A true GB1116037A (en) 1968-06-06

Family

ID=10276831

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2851366A Expired GB1116037A (en) 1966-06-24 1966-06-24 Preparation of mesityl oxide and/or methyl isobutyl ketone

Country Status (1)

Country Link
GB (1) GB1116037A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5925796A (en) * 1997-09-16 1999-07-20 Union Carbide Chemicals & Plastics Technology Corporation Method to de-couple methyl isobutyl ketone and diisobutyl ketone co-produced from acetone and/or isopropyl alcohol
EP1103538A1 (en) * 1999-11-24 2001-05-30 Oxeno Olefinchemie GmbH Process for carrying out aldolcondensations
CN111001432A (en) * 2018-10-08 2020-04-14 中国石油化工股份有限公司 Catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and preparation method and application thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5925796A (en) * 1997-09-16 1999-07-20 Union Carbide Chemicals & Plastics Technology Corporation Method to de-couple methyl isobutyl ketone and diisobutyl ketone co-produced from acetone and/or isopropyl alcohol
EP1103538A1 (en) * 1999-11-24 2001-05-30 Oxeno Olefinchemie GmbH Process for carrying out aldolcondensations
SG90201A1 (en) * 1999-11-24 2002-07-23 Oxeno Olefinchemie Gmbh Process for carrying out aldol condensations
KR100622288B1 (en) * 1999-11-24 2006-09-11 옥세노 올레핀케미 게엠베하 Process for carrying out aldol condensations
CN111001432A (en) * 2018-10-08 2020-04-14 中国石油化工股份有限公司 Catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and preparation method and application thereof

Similar Documents

Publication Publication Date Title
US2587753A (en) Method for purifying alcohols
US3170000A (en) Tertiary olefin separation via etherification with small surface area catalysts
US3121124A (en) Tertiary olefin separation via etherification
US4665237A (en) Process for producing methyl tertiary butyl ether
US3665048A (en) Process to produce high purity isobutylene
Hibbert USE OF IODINE AS A DEHYDRATING AND CONDENSING AGENT.
GB1148907A (en) Purification of phenol
US4484013A (en) Process for coproduction of isopropanol and tertiary butyl alcohol
US3013954A (en) Separation of organic mixtures
US2238016A (en) Purification of ketones
GB1116037A (en) Preparation of mesityl oxide and/or methyl isobutyl ketone
EP0265030A1 (en) Recovery of propylene glycol mono t-butoxy ether
US3442963A (en) Dehydration of alpha methylbenzyl alcohol to styrene
US3993701A (en) Methylation of α-naphthol to 2-methyl-1-naphthol
US2881227A (en) Production of dhsopropyl benzenes
US2229652A (en) Process for producing butadiene
US3449219A (en) Process for fractionating propylene from propylene oxide in the presence of hydrocarbon flux
GB1021417A (en) Process for preparing epichlorohydrin
US2692277A (en) Manufacture of cyclohexanols and esters thereof, from isopropyl alcohol or secondary butyl alcohol
US2615051A (en) Etherification of hydroquinone
US2568841A (en) Method of synthesizing gasoline hydrocarbons
US3445538A (en) Preparation of olefins
US2855430A (en) Process for the preparation of diisopropylbenzene
US2647861A (en) Purification of ketones by distillation
US3449436A (en) Purification of ketones