GB1097132A - Manufacture of epoxy compounds and araliphatic compounds - Google Patents

Manufacture of epoxy compounds and araliphatic compounds

Info

Publication number
GB1097132A
GB1097132A GB87/65A GB8765A GB1097132A GB 1097132 A GB1097132 A GB 1097132A GB 87/65 A GB87/65 A GB 87/65A GB 8765 A GB8765 A GB 8765A GB 1097132 A GB1097132 A GB 1097132A
Authority
GB
United Kingdom
Prior art keywords
aralkyl
compounds
epoxidation
dehydration
hydroperoxides
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
GB87/65A
Inventor
John Kollar
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.)
Halcon International Inc
Original Assignee
Halcon International Inc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26990064&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=GB1097132(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Halcon International Inc filed Critical Halcon International Inc
Publication of GB1097132A publication Critical patent/GB1097132A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/32—Manganese, technetium or rhenium
    • B01J23/36—Rhenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/057—Selenium or tellurium; Compounds thereof
    • B01J27/0573—Selenium; Compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/057—Selenium or tellurium; Compounds thereof
    • B01J27/0576—Tellurium; Compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C07C15/46—Styrene; Ring-alkylated styrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Abstract

Alkenylaromatic and alkylaromatic hydrocarbons are made by dehydration or hydrogenation, respectively, of aralkyl alcohols obtained as by-products in the epoxidation of olefinic compounds using aralkyl hydroperoxides. Prefered aralkyl hydroperoxides are those derived from alkylaromatic compounds having at least one hydrogen atom on the carbon adjacent to the aromatic ring; reduction to the corresponding aralkyl alcohol and subsequent dehydration yields styrene type hydrocarbons, the preferred hydroperoxides of ethylbenzene and cumene yielding styrene and a -methylstyrene. Dehydration may be effected in the vapour phase at 180-280 DEG C. over a dehydration catalyst, e.g. silica, alumina or, particularly, titania. Hydrogenation of the aralkyl alcohol to the corresponding alkylaromatic hydrocarbon is carried out in a known manner.ALSO:Olefinically unsaturated compounds are epoxidized by reaction in the liquid phase with an aralkyl hydroperoxide in the presence of a metal epoxidation catalyst which contains at least one metal other than alkali metals or alkaline earth metals. The epoxidation proceeds with reduction of the hydroperoxide to the corresponding aralkyl alcohol which is subsequently dehydrated or hydrogenated to the corresponding aralkenyl or aralkyl compounds (see Division C5). Specified unsaturated compounds include C2- 30 aliphatic and alicyclic olefins, esters, alcohols, ketones, ethers, mercaptans and alkenyl chlorides. Preferred hydroperoxides are those derived from alkyl-aromatic compounds having at least one hydrogen atom on a carbon adjacent to the ring, particularly cumene and ethylbenzene. Specified catalysts are those containing compounds of Mo, W or V. It is preferred to add the catalyst in the form of a compound which is at least partially soluble in the reaction medium, e.g. as a carboxylate or carbonyl. The epoxidation may be effected at -20 DEG to +200 DEG C., preferably in the presence of a solvent. Examples describe the epoxidation of propylene, 4-vinyl cyclohexene, octene-1, dodecene-1 or hexadecene-1.
GB87/65A 1964-01-07 1965-01-01 Manufacture of epoxy compounds and araliphatic compounds Expired GB1097132A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33615064A 1964-01-07 1964-01-07
US41457564A 1964-11-30 1964-11-30

Publications (1)

Publication Number Publication Date
GB1097132A true GB1097132A (en) 1967-12-29

Family

ID=26990064

Family Applications (2)

Application Number Title Priority Date Filing Date
GB87/65A Expired GB1097132A (en) 1964-01-07 1965-01-01 Manufacture of epoxy compounds and araliphatic compounds
GB49907/65A Expired GB1133313A (en) 1964-01-07 1965-11-24 Production of styrenes and of oxirane compounds

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB49907/65A Expired GB1133313A (en) 1964-01-07 1965-11-24 Production of styrenes and of oxirane compounds

Country Status (11)

Country Link
JP (2) JPS495323B1 (en)
BE (2) BE657838A (en)
BR (1) BR6575123D0 (en)
CH (2) CH438251A (en)
DE (2) DE1518967C3 (en)
DK (1) DK129922B (en)
GB (2) GB1097132A (en)
IL (1) IL22736A (en)
LU (2) LU47712A1 (en)
NL (2) NL150450B (en)
SE (2) SE334150B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1209155A1 (en) * 2000-11-20 2002-05-29 Degussa AG Process for the preparation of propylene oxide free of coupling products

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3439001A (en) * 1965-10-01 1969-04-15 Halcon International Inc Epoxidation using ethylbenzene hydroperoxide with alkali or adsorbent treatment of recycle ethylbenzene
US4480113A (en) * 1982-09-28 1984-10-30 The Halcon Sd Group, Inc. Epoxidation catalyst and process
JPS61293936A (en) * 1985-06-21 1986-12-24 Kureha Chem Ind Co Ltd Liquid-phase dehydration of alcohol having aromatic side-chain at alpha-site
JP3552306B2 (en) * 1994-11-04 2004-08-11 住友化学工業株式会社 Method for producing propylene oxide and styrene monomer
US6984761B2 (en) * 2002-12-16 2006-01-10 Exxonmobil Chemical Patents Inc. Co-production of phenol, acetone, α-methylstyrene and propylene oxide, and catalyst therefor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2399395A (en) * 1943-09-23 1946-04-30 Carbide & Carbon Chem Corp Process for making styrene from methyl phenyl carbinol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1209155A1 (en) * 2000-11-20 2002-05-29 Degussa AG Process for the preparation of propylene oxide free of coupling products

Also Published As

Publication number Publication date
BE672438A (en) 1966-05-17
DK129922C (en) 1975-05-12
BE657838A (en) 1965-06-30
CH459166A (en) 1968-07-15
LU49867A1 (en) 1967-05-18
DE1518967A1 (en) 1969-09-04
DK129922B (en) 1974-12-02
LU47712A1 (en) 1966-07-04
CH438251A (en) 1967-06-30
NL150450B (en) 1976-08-16
DE1543032B2 (en) 1981-07-23
JPS495323B1 (en) 1974-02-06
GB1133313A (en) 1968-11-13
DE1543032A1 (en) 1969-10-09
BR6575123D0 (en) 1973-09-11
SE343855B (en) 1972-03-20
NL6515037A (en) 1966-05-31
DE1518967B2 (en) 1980-09-18
NL147430B (en) 1975-10-15
IL22736A (en) 1969-01-29
DE1543032C3 (en) 1982-05-13
DE1518967C3 (en) 1981-10-08
JPS5331848B1 (en) 1978-09-05
NL6500118A (en) 1965-07-08
SE334150B (en) 1971-04-19

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