GB615571A - Production of unsaturated alcohols - Google Patents

Production of unsaturated alcohols

Info

Publication number
GB615571A
GB615571A GB17477/46A GB1747746A GB615571A GB 615571 A GB615571 A GB 615571A GB 17477/46 A GB17477/46 A GB 17477/46A GB 1747746 A GB1747746 A GB 1747746A GB 615571 A GB615571 A GB 615571A
Authority
GB
United Kingdom
Prior art keywords
ether
sulphate
catalyst
methallyl
allyl
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
GB17477/46A
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.)
Shell Development Co
Original Assignee
Shell Development 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 Shell Development Co filed Critical Shell Development Co
Publication of GB615571A publication Critical patent/GB615571A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02Acyclic alcohols with carbon-to-carbon double bonds
    • C07C33/025Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
    • C07C33/03Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/584Recycling of catalysts

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

Abstract

A supported copper sulphate catalyst which may be used as a hydration catalyst in the production of an unsaturated alcohol by reacting water with an unsaturated ether, in the vapour phase (see Group IV (b)) may be prepared by dissolving copper sulphate in water to make a volume of solution just sufficient to wet the granular carrier thoroughly, mixing the carrier with the solution and drying in air at about 200 DEG C. Sodium sulphate or potassium sulphate may be added as promoters and the catalyst may be acid-treated or caustic alkali-treated, e.g. by soaking the dried supported catalyst in sodium hydroxide solution. An unsupported copper sulphate catalyst of neutral reaction is prepared by adding sodium hydroxide solution to copper sulphate solution, drying and granulating. A copper sulphate on activated alumina catalyst may be regenerated by oxidation with air at about 475 DEG to 550 DEG C. In an example, an alumina catalyst is prepared by boiling activated alumina in sodium hydroxide solution and then digesting in concentrated aluminium sulphate solution. U.S.A. Specifications 1,868,869, 1,949,344 and 2,015,593 are referred to.ALSO:An unsaturated alcohol is produced from an unsaturated ether thereof by reacting water with an unsaturated ether containing an unsaturated linkage between two carbon atoms of aliphatic character, one of which is directly linked to a saturated carbon atom which in turn is directly linked to the ether oxygen atom, the reaction being effective in the vapour phase in the presence of a hydration catalyst. Specified unsaturated ethers are allyl methyl ether, methallyl ethyl ether, crotyl methyl ether, allyl vinyl ether, methallyl isopropyl ether, tiglyl phenyl ether, cinnamyl butyl ether, allyl cyclohexyl ether, 3-chloro-2-propenyl ethyl ether, propargyl methyl ethel, and their homologues; allyl 3-butenyl ether, methallyl 3-pentenyl ether, crotyl 4-cyclohexenyl ether, allyl methallyl ether, allyl cinnamyl ether, methallyl tiglyl ether, allyl crotyl ether, 3-chloro-2-propenyl methallyl ether, allyl propargyl ether and their homologues; diallyl ether, di-(methallyl) or dicrotyl, ditiglyl, dicinnamyl, di-(3-chloro-2-butenyl), di-(ethallyl), di-(2-cyclopentenyl), di-(3-chloro-2-propenyl), di - (2 - methyl - 2 - hexenyl), di - (2 - methyl - 2 - pentenyl) and di-(2-cyclohexenyl) ethers and their homologues. The reaction temperature is preferably between 180 DEG and 300 DEG C. and atmospheric, reduced or elevated pressures may be employed. Solid hydration catalysts which may be employed include copper sulphate, aluminium sulphate, ferrous sulphate, cobaltous sulphate, nickelous sulphate, aluminium phosphate, cadmium metaphosphate and activated alumina or mixtures thereof. The catalyst may be supported on a carrier, e.g. alumina, thoria, diatomaceous earth, porous carborundum, silicon carbide porous aggregates or silica gel and particularly adsorptive or activated aluminas including alumina alpha trihydrate known as gibbsite or hydrargillite, the alumina beta trihydrate bayerite and the alumina alpha monohydrate bochmite, gamma alumina, gelatinous aluminium hydroxide, bauxite, and the adsorptive alumina prepared by dehydration of alumina trihydrate crystallised from alkali aluminate solutions. A substance such as sodium sulphate or potassium sulphate may be added to help promote the catalyst which may be acid treated or caustic alkali-treated. It is preferred to employ a space velocity of between 0.1 and 10.0 liquid volumes of ether per volume of catalyst per hour. Examples describe the production of allyl alcohol by reacting diallyl ether and steam in the presence, respectively, of the following hydration catalysts: copper sulphate on activated alumina; copper sulphate and diatomaceous earth; copper sulphate treated with sodium hydroxide solution and then dried and granulated; activated alumina; a catalyst prepared by boiling activated alumina in sodium hydroxide solution and then digesting in concentrated aluminium sulphate solution; pelleted aluminium phosphate prepared as in U.S.A. Specification 1,949,344 by adding an aqueous solution of ammonium acid phosphate to an aqueous solution of aluminium nitrate, making the solution alkaline with ammonia and drying and pelleting the precipitated aluminium phosphate with a minor amount of the material "Hyflo Supercel" (Registered Trade Mark) added; other examples describe the production of methallyl alcohol from di-(methallyl) ether and steam using copper sulphate on activated alumina; crotyl alcohol from dicrotyl ether and steam using the same catalyst, and allyl alcohol and methallyl alcohol by reacting allyl methallyl ether and steam over copper sulphate. U.S.A. Specifications 1,868,869 and 2,015,593 also are referred to. The Specification as open to inspection under Sect. 91 also specifies the following unsaturated ethers as starting materials: 3-butenyl methyl ether, 3-pentenyl propyl ether, 3-hexenyl amyl ether, 4-hexenyl ethyl ether, 3-cyclohexenyl vinyl ether, 5-hexenyl isopropenyl ether, di-(3-butenyl) ether, di-(3-pentenyl) p ether, di-(4-hexenyl) ether and di-(4-cyclohexenyl) ether and an example is given for the production of 1-buten-4-ol by the reaction of di-(3-butenyl) ether and steam in the presence of copper sulphate treated with sodium hydroxide solution and then dried and pelleted. This subject-matter does not appear in the Specification as accepted.
GB17477/46A 1945-11-13 1946-06-11 Production of unsaturated alcohols Expired GB615571A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US615571XA 1945-11-13 1945-11-13

Publications (1)

Publication Number Publication Date
GB615571A true GB615571A (en) 1949-01-07

Family

ID=22036532

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17477/46A Expired GB615571A (en) 1945-11-13 1946-06-11 Production of unsaturated alcohols

Country Status (1)

Country Link
GB (1) GB615571A (en)

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