GB618189A - Improvements in or relating to dehydrohalogenation processes - Google Patents

Improvements in or relating to dehydrohalogenation processes

Info

Publication number
GB618189A
GB618189A GB3235346A GB3235346A GB618189A GB 618189 A GB618189 A GB 618189A GB 3235346 A GB3235346 A GB 3235346A GB 3235346 A GB3235346 A GB 3235346A GB 618189 A GB618189 A GB 618189A
Authority
GB
United Kingdom
Prior art keywords
mono
ethylene glycol
alcoholate
heating
ethyl ether
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
GB3235346A
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 Refining and Marketing Co Ltd
Original Assignee
Shell Refining and Marketing 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 Shell Refining and Marketing Co Ltd filed Critical Shell Refining and Marketing Co Ltd
Priority to GB3235346A priority Critical patent/GB618189A/en
Publication of GB618189A publication Critical patent/GB618189A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule

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

Abstract

Alkynes containing at least four carbon atoms in the molecule are produced by heating dihalogen-alkanes and monohalogen-alkenes with an excess of an alkali metal alcoholate of an alcohol boiling above 100 DEG C. dissolved in alcohol boiling above 100 DEG C. and monohalogen-alkenes by heating dihalogen-alkanes with an equimolar quantity of the same although not necessarily anhydrous reagent. The dihalogen-alkanes and monohalogen-alkenes contain at least four carbon atoms, in the former halogen is attached to the same or adjacent carbon atoms and in the latter to an unsaturated carbon atom. Chlorine and bromine as halogens and sodium and potassium alcoholates are preferred. Preferred alcohols both as solvents and for alcoholate production are mono-alkyl ethers of glycols, e.g. mono-methyl and mono-ethyl ethers of ethylene and diethylene glycols others specified being amyl, isoamyl, hexyl and isohexyl alcohols, ethylene and propylene glycols and mono- and di-methyl or ethyl ethers of glycerol. The reaction with dihalogen-alkanes takes place in two stages, the first stage resulting in the elimination of one molecule of hydrogen halide to give a mixture of isomeric mono-halogen-alkenes which are then converted under preferably anhydrous conditions to alkynes by the removal of another molecule of hydrogen halide. Thus, in the first stage a mixture containing 2-chloroalkenes-1 and cis-and trans-1-chloroalkenes-1 is obtained from 1,2-dichloroalkanes. It is stated that butyne-1 is obtained from 1,1-dichlorobutane, 1,2-dibromobutane or 1 - bromobutene - 1; pentyne - 2 from 2,3-dibromopentane or 3-chloropentene-2; hexyne-2 from 2,3-dichlorohexane or 3-bromohexene-2; heptyne-3 from 3,4-dibromoheptane or 4-bromoheptane-3; heptyne-1 from 1,2-dibromoheptane, 1,1-dichloroheptane, 1 - bromo - heptene - 1 or 2 - chloroheptene - 1; hexyne - 1 from 1,2-dibromohexane or 1-bromohexene-1 and bromohexene-1 from 1,2-dibromohexane. The anhydrous alcoholate is prepared by dissolving an alkali metal hydroxide in an alcohol, heating and removing water by an azeotropic distillation with, e.g. benzene, toluene or xylene, or by dissolving the free metal in the alcohol. In each example, ethylene glycol mono-ethyl ether is used as a solvent and hexynes, hexyne-1 preponderating, are produced in (1) and (3) by treating mixed 1- and 2-chlorohexene-1 (obtained by heating 1,2-dichlorohexane with potassium hydroxide dissolved in ethylene glycol monoethyl ether) or dry 2-chlorohexene-1 with anhydrous sodium or potassium alcoholates of ethylene glycol mono-ethyl ether and in (2) from dry 1,2-dichlorohexane and the anhydrous potassium alcoholate of ethylene glycol mono-ethyl ether, in (4) heptynes, heptyne-1 is mentioned, are obtained by treating mixed monochloroheptenes, obtained by heating 1,2-dichloroheptane with sodium hydroxide dissolved in ethylene glycol mono-ethyl ether, with the sodium alcoholate of ethylene glycol mono-ethyl ether.
GB3235346A 1946-10-31 1946-10-31 Improvements in or relating to dehydrohalogenation processes Expired GB618189A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3235346A GB618189A (en) 1946-10-31 1946-10-31 Improvements in or relating to dehydrohalogenation processes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3235346A GB618189A (en) 1946-10-31 1946-10-31 Improvements in or relating to dehydrohalogenation processes

Publications (1)

Publication Number Publication Date
GB618189A true GB618189A (en) 1949-02-17

Family

ID=10337310

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3235346A Expired GB618189A (en) 1946-10-31 1946-10-31 Improvements in or relating to dehydrohalogenation processes

Country Status (1)

Country Link
GB (1) GB618189A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623077A (en) * 1950-12-13 1952-12-23 Rohm & Haas Preparation of alkali metal vinylacetylides
WO1982003025A1 (en) * 1981-03-05 1982-09-16 Franklin Institute Improved method for decomposition of halogenated organic compounds
US4460797A (en) * 1981-03-05 1984-07-17 The Franklin Institute Method for decomposition of halogenated organic compounds
US4471143A (en) * 1980-04-21 1984-09-11 The Franklin Institute Composition for decomposing halogenated organic compounds
US4602994A (en) * 1982-09-30 1986-07-29 The Franklin Institute Removal of PCBs and other halogenated organic compounds from organic fluids
US5093011A (en) * 1990-12-12 1992-03-03 Chemical Waste Management, Inc. Process for dehalogenation of contaminated waste materials

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623077A (en) * 1950-12-13 1952-12-23 Rohm & Haas Preparation of alkali metal vinylacetylides
US4471143A (en) * 1980-04-21 1984-09-11 The Franklin Institute Composition for decomposing halogenated organic compounds
WO1982003025A1 (en) * 1981-03-05 1982-09-16 Franklin Institute Improved method for decomposition of halogenated organic compounds
US4460797A (en) * 1981-03-05 1984-07-17 The Franklin Institute Method for decomposition of halogenated organic compounds
US4602994A (en) * 1982-09-30 1986-07-29 The Franklin Institute Removal of PCBs and other halogenated organic compounds from organic fluids
US5093011A (en) * 1990-12-12 1992-03-03 Chemical Waste Management, Inc. Process for dehalogenation of contaminated waste materials

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