GB460143A - Improvements in the manufacture and production of alkyl halides and of unsaturated organic compounds - Google Patents

Improvements in the manufacture and production of alkyl halides and of unsaturated organic compounds

Info

Publication number
GB460143A
GB460143A GB2019035A GB2019035A GB460143A GB 460143 A GB460143 A GB 460143A GB 2019035 A GB2019035 A GB 2019035A GB 2019035 A GB2019035 A GB 2019035A GB 460143 A GB460143 A GB 460143A
Authority
GB
United Kingdom
Prior art keywords
methyl
chloride
methanol
ether
aliphatic
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
GB2019035A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB460143A publication Critical patent/GB460143A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina

Landscapes

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

Abstract

Alkyl halides and unsaturated organic compounds are produced by reacting an aliphatic alcohol or ether with a compound containing a halogen atom and a hydrogen atom attached to two adjacent carbon atoms, in the presence of a dehydrating catalyst consisting of or containing an oxide or salt. The halogen compound may be aliphatic, alicyclic, aromatic-aliphatic, or heterocyclic, the halogen being on an aliphatic carbon atom. Suitable halogen compounds are propyl, isopropyl and bornyl chlorides, isopropyl iodide, isobutyl bromide, a and b -chlorpropionic acids and their esters, chlorpropionic nitrile, and chlorcyclohexane; di-, tri-, tetra- and pentachlorethanes, and 1-2-dibromcyclohexane. Suitable alcohols and ethers are lower monohydric aliphatic alcohols, benzyl alcohol, glycols, and the corresponding ethers; also alcohols such as vinyl alcohol which are not stable in the free state. In some cases, as when employing ethylene chloride as starting material, the products include oxygen-containing compounds such as acetaldehyde in addition to the unsaturated compound such as vinyl chloride. In the examples there are obtained (1) and (2) propylene and methyl chloride or bromide from isopropyl chloride or bromide and methyl ether; (3) propylene and methyl iodide from isopropyl iodide and methanol; (4) methyl chloride and an olefine from a monochlorinated aliphatic hydrocarbon of 12--14 carbon atoms and methanol; (5), (6) and (8) vinyl and methyl chlorides from 1-2-dichlor-ethane and methanol or methyl ether; (7) vinyl and methyl fluorides from 1-1-difluor-ethane and methanol; (9) cis- and trans-dichlorethylene, asymmetric dichlorethylene and methyl chloride from 1.2.2-trichlor-ethane and methanol; (11) to (14) trichlorethylene and alkyl chloride from 1.1.2.2-tetrachlorethane and methanol, ethanol or dimethyl ether; (15) tribromethylene and methyl bromide from 1.1.2.2-tetrabromethane and methanol; (16) tetrachlorethylene and methyl chloride from pentachlorethane and methanol; (17) and (18) cyclohexene and methyl or ethyl chloride from monochlorcyclohexane and methanol or ethanol; (19) cyclohexene and vinyl chloride from monochlorcyclohexane and methyl ether; (20) camphene and alkyl chloride from bornyl or isobornyl chloride and alkyl alcohol or ether; (21) dihydrobenzene and methyl chloride or bromide from dichlor- or dibrom-cyclohexane and methanol; (22) to (24) acrylic acid or its methyl ester or nitrile and methyl chloride from b -chlor-propionic acid or its ester or nitrile and methanol or methyl ether.
GB2019035A 1935-06-09 1935-07-15 Improvements in the manufacture and production of alkyl halides and of unsaturated organic compounds Expired GB460143A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI52534D DE704759C (en) 1935-06-09 1935-06-09 Process for the simultaneous preparation of alkyl halides and unsaturated compounds

Publications (1)

Publication Number Publication Date
GB460143A true GB460143A (en) 1937-01-15

Family

ID=10141893

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2019035A Expired GB460143A (en) 1935-06-09 1935-07-15 Improvements in the manufacture and production of alkyl halides and of unsaturated organic compounds

Country Status (3)

Country Link
DE (1) DE704759C (en)
FR (1) FR805563A (en)
GB (1) GB460143A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2481157A (en) * 1944-10-27 1949-09-06 Universal Oil Prod Co Treatment of halo-hydrocarbons

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2755310A (en) * 1951-11-28 1956-07-17 Olin Mathieson Production of organic chlorides by reaction of organic compound with ammonium chloride
US2755311A (en) * 1951-12-29 1956-07-17 Olin Mathieson Production of organic chlorides by reaction of organic compound with ammonium chloride
US2755316A (en) * 1951-12-29 1956-07-17 Olin Mathieson Reaction of organic compounds with ammonium chloride
US2755312A (en) * 1951-12-29 1956-07-17 Olin Mathieson Production of organic chlorides by reaction of organic compound with ammonium chloride
DE964043C (en) * 1954-01-26 1957-05-16 Bayer Ag Process for the preparation of halogen-substituted olefins
JPS6043051B2 (en) * 1979-05-31 1985-09-26 東ソー株式会社 Method for brominating the side chain of m-phenoxytoluene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2481157A (en) * 1944-10-27 1949-09-06 Universal Oil Prod Co Treatment of halo-hydrocarbons

Also Published As

Publication number Publication date
DE704759C (en) 1941-04-07
FR805563A (en) 1936-11-24

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