GB696125A - Manufacture of hydroxy ethers - Google Patents

Manufacture of hydroxy ethers

Info

Publication number
GB696125A
GB696125A GB31463/49A GB3146349A GB696125A GB 696125 A GB696125 A GB 696125A GB 31463/49 A GB31463/49 A GB 31463/49A GB 3146349 A GB3146349 A GB 3146349A GB 696125 A GB696125 A GB 696125A
Authority
GB
United Kingdom
Prior art keywords
sodium hydroxide
boron trifluoride
ethanol
ethers
formula
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
GB31463/49A
Inventor
Donald Peter Young
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
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 Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB31463/49A priority Critical patent/GB696125A/en
Publication of GB696125A publication Critical patent/GB696125A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy 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
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/10—Saturated ethers of polyhydroxy compounds
    • C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups

Landscapes

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

Abstract

The invention comprises ethers of formula (a) <FORM:0696125/IV (b)/1> wherein R is an alkyl radicle derived from a primary aliphatic alcohol or a mono- or polyhydroxylated alkyl radicle and ethers of formula (b) <FORM:0696125/IV (b)/2> wherein R is an alkyl radicle, a mono- or polyhydroxylated alkyl radicle, a mono- or dinuclear aryl group or an alkylated derivative thereof. Ethers of formula (a) are made by reacting 1,2-epoxy-2,4,4-trimethyl pentane with a monohydric primary or polyhydric alcohol, e.g. ethylene glycol, propane-1,3-diol, 2-methyl-pentane-2,4-diol and glycerols, in the presence of sulphuric or phosphoric acids or boron trifluoride. Advantageously the alcohol is in large excess. The temperature should not rise substantially above 50 DEG C. except when phosphoric acid is used. Ethers of formula (b) are made by reacting the above epoxide with hydroxy-compounds such as primary fatty alcohols, phenols, cresols, a - or b -naphthol and polyhydric alcohols in the presence of a basic catalyst. Catalysts specified are hydroxides, alkoxides, phenoxides or naphthoxides of alkali metals, e.g. sodium or potassium, and alkali metal salts of lower fatty acids. The temperature is 60-250 DEG C., preferably 100-150 DEG C., with an excess of hydroxy-compound. The ethers may be recovered by extraction with ether or by fractional distillation. In examples the above epoxide is reacted with (1) ethanol, methanol or n-butanol containing sulphuric acid, (2) and (3) methanol containing a boron trifluoride-diethyl ether complex, (4) ethanol and phosphoric acid, (5) ethanol containing sodium, (6) ethanol or isopropanol and sodium ethoxide, (7) ethanol and sodium hydroxide, (8) n-butanol and sodium hydroxide, (9) phenol and ethanol containing sodium hydroxide, (10) lauryl alcohol and sodium hydroxide, (11) b -naphthol and aqueous sodium hydroxide, (12) ethylene glycol and boron trifluoride etherate, (13) ethylene glycol and sodium hydroxide, (14) propane-1,3-diol and boron trifluoride etherate, (15) 2 - methylpentan - 2,4 - diol and boron trifluoride etherate, and (16) glycerol and boron trifluoride etherate to give the required products corresponding to formula (a) or (b). 2(21 - Hydroxyethoxy) - 2,4,4 - trimethylpentan-1-ol formed in (12) is converted to bis-a ,g ,g -trimethyl valerate and a bis-3,5-dinitrobenzoate; 2 - (21,31 - dihydroxy - n-propoxy) - 2,4,4 - trimethylpentan - 1 - ol formed in (16) is converted to a tri-n-nitrobenzoate and 2-(21-hydroxy-n-propoxy)-2,4,4-trimethylpentan-1-ol formed in (14) is converted to the di-n-nitrobenzoate.
GB31463/49A 1949-12-08 1949-12-08 Manufacture of hydroxy ethers Expired GB696125A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB31463/49A GB696125A (en) 1949-12-08 1949-12-08 Manufacture of hydroxy ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31463/49A GB696125A (en) 1949-12-08 1949-12-08 Manufacture of hydroxy ethers

Publications (1)

Publication Number Publication Date
GB696125A true GB696125A (en) 1953-08-26

Family

ID=10323455

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31463/49A Expired GB696125A (en) 1949-12-08 1949-12-08 Manufacture of hydroxy ethers

Country Status (1)

Country Link
GB (1) GB696125A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1279671B (en) * 1964-12-17 1968-10-10 British Petroleum Co Process for the production of mono-alkoxy-diols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1279671B (en) * 1964-12-17 1968-10-10 British Petroleum Co Process for the production of mono-alkoxy-diols

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