GB970371A - Preparation of acetals of alkenals - Google Patents

Preparation of acetals of alkenals

Info

Publication number
GB970371A
GB970371A GB2226/62A GB222662A GB970371A GB 970371 A GB970371 A GB 970371A GB 2226/62 A GB2226/62 A GB 2226/62A GB 222662 A GB222662 A GB 222662A GB 970371 A GB970371 A GB 970371A
Authority
GB
United Kingdom
Prior art keywords
alkenals
organic
acetal
phase
alcohol
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
GB2226/62A
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 Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB970371A publication Critical patent/GB970371A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings

Abstract

Acetals of alkenals are obtained by reacting an alkenal which is an aliphatic aldehyde consisting of a hydrocarbon portion having at least one olefinic double bond on an otherwise saturated chain and a formyl group attached to a chain carbon atom with an acyclic alcohol comprising an alkyl or alkenyl group having a hydroxyl group attached to one of the carbon atoms at a temperature below 25 DEG C. in the presence of an inert substantially water-immiscible liquid organic solvent so as to form an aqueous and an organic liquid phase, separating the aqueous phase from the organic phase and recovering the acetal from the organic phase. Specified alkenals are methacrolein, alpha-ethylacrolein, alpha-hexylacrolein, beta-pentylacrolein, crotonaldehyde and tiglaldehyde. The alcohols may be methanol, ethane, propanol, isopropanol, butanol, sec. butanol, pentanols, hexanols, isooctanol, allylalcohol, methallyl alcohol and oleyl alcohol. Specified organic solvents are hexane, heptane, octane, nonane, decane, undecane, dodecane, benzene, toluene, xylenes, ethyl benzene, ethylene dichloride, methylene dichloride and carbon tetrachloride. The reaction is preferably carried out in the presence of an acidic catalyst such as sulphuric, hydrochloric, hydrofluoric, p.toluene, sulphonic, chloracetic, or trichloracetic acids. Examples describe the preparation of acrolein dimethyl acetal and acrolein diethyl acetal. Specification 713,088 is referred to.
GB2226/62A 1961-01-24 1962-01-22 Preparation of acetals of alkenals Expired GB970371A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US8448461A 1961-01-24 1961-01-24

Publications (1)

Publication Number Publication Date
GB970371A true GB970371A (en) 1964-09-23

Family

ID=22185247

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2226/62A Expired GB970371A (en) 1961-01-24 1962-01-22 Preparation of acetals of alkenals

Country Status (2)

Country Link
BE (1) BE612928A (en)
GB (1) GB970371A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0150280A2 (en) * 1984-02-01 1985-08-07 Degussa Aktiengesellschaft Process for the preparation of acetals
CN114933514A (en) * 2022-06-20 2022-08-23 万华化学集团股份有限公司 Preparation method of bio-based isooctyl alcohol

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0150280A2 (en) * 1984-02-01 1985-08-07 Degussa Aktiengesellschaft Process for the preparation of acetals
EP0150280A3 (en) * 1984-02-01 1986-07-30 Degussa Aktiengesellschaft Process for the preparation of acetals
CN114933514A (en) * 2022-06-20 2022-08-23 万华化学集团股份有限公司 Preparation method of bio-based isooctyl alcohol
CN114933514B (en) * 2022-06-20 2023-05-30 万华化学集团股份有限公司 Preparation method of bio-based isooctyl alcohol

Also Published As

Publication number Publication date
BE612928A (en) 1962-07-23

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