GB977281A - Surface-active sulphates of alkyl ether alcohols and a process for their preparation - Google Patents

Surface-active sulphates of alkyl ether alcohols and a process for their preparation

Info

Publication number
GB977281A
GB977281A GB4080362A GB4080362A GB977281A GB 977281 A GB977281 A GB 977281A GB 4080362 A GB4080362 A GB 4080362A GB 4080362 A GB4080362 A GB 4080362A GB 977281 A GB977281 A GB 977281A
Authority
GB
United Kingdom
Prior art keywords
reaction
ether
olefins
ethylene glycol
water
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
GB4080362A
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 GB977281A publication Critical patent/GB977281A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids

Landscapes

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

Abstract

The invention comprises surface active sulphates of alkyl ether alcohols of the formula R1R2R3C.O.CH2CH2OH in which R1 and R2 are alkyl groups, R3 is hydrogen or an alkyl group, and R1, R2 and R3 together contain at least 7, and preferably not more than 19, C atoms, and alkali metal, ammonium or amine salts thereof. R1 preferably contains 10-14 C atoms, R2 is preferably -CH3 and R3, H or CH3. The ether-alcohol may be made by (a) the reaction of olefins with ethylene glycol, (b) the reaction of olefins withethylene halohydrins, followed by hydrolysis of the halogen-containing products, or (c) the reaction of secondary or tertiary alcohols with ethylene oxide. Reactions (a) and (b) require acid catalysts, preferably BF3 or H2SO4, and temperatures of 50-200 DEG C., and a polar solvent, preferably nitromethane, is desirable for (a). Efficiency is improved by the addition to BF3 of 0.3-1.1 moles of water, and a hydrocarbon liquid, e.g. pentane, may be used to extract the reaction mixture. The sulphation is carried out using known agents (listed), preferably a slight excess of chlorosulphonic acid at 0-10 DEG C. Examples I-IV describe the preparation of 1-methyl-undecyl ethylene glycol ether from dodecene-1 and ethylene glycol in nitromethane, using a BF3-water catalyst. Examples V and VI describe the reaction of C13-15 olefins, and of dodecene-1, with 2-chloroethanol, using BF3-water and H2SO4 catalysts respectively, and the hydrolysis of the former product directly to the ether alcohol, using NaOH, and of the latter via the acetate, formed by reaction with potassium acetate, followed by saponification to the ether alcohol. The products are all sulphated with chlorosulphonic acid.
GB4080362A 1961-10-30 1962-10-29 Surface-active sulphates of alkyl ether alcohols and a process for their preparation Expired GB977281A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL270811 1961-10-30

Publications (1)

Publication Number Publication Date
GB977281A true GB977281A (en) 1964-12-02

Family

ID=19753372

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4080362A Expired GB977281A (en) 1961-10-30 1962-10-29 Surface-active sulphates of alkyl ether alcohols and a process for their preparation

Country Status (1)

Country Link
GB (1) GB977281A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4217296A (en) * 1978-07-24 1980-08-12 Fmc Corporation Alkyl glyceryl ether sulfate salts and process for their preparation
US4269786A (en) * 1978-11-13 1981-05-26 Fmc Corporation Alkyl glyceryl ether sulfate salts and process for their preparation
WO2023172859A1 (en) 2022-03-07 2023-09-14 The Procter & Gamble Company Processes for making concentrated surfactant blends

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4217296A (en) * 1978-07-24 1980-08-12 Fmc Corporation Alkyl glyceryl ether sulfate salts and process for their preparation
US4269786A (en) * 1978-11-13 1981-05-26 Fmc Corporation Alkyl glyceryl ether sulfate salts and process for their preparation
WO2023172859A1 (en) 2022-03-07 2023-09-14 The Procter & Gamble Company Processes for making concentrated surfactant blends

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