CA2510093A1 - Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones - Google Patents

Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones Download PDF

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Publication number
CA2510093A1
CA2510093A1 CA002510093A CA2510093A CA2510093A1 CA 2510093 A1 CA2510093 A1 CA 2510093A1 CA 002510093 A CA002510093 A CA 002510093A CA 2510093 A CA2510093 A CA 2510093A CA 2510093 A1 CA2510093 A1 CA 2510093A1
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Canada
Prior art keywords
alpha
dichloro
ketones
chlorovinyl
acetylenes
Prior art date
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Granted
Application number
CA002510093A
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French (fr)
Other versions
CA2510093C (en
Inventor
Allan W. Rey
K.S. Keshava Murthy
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Apotex Pharmachem Inc
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Apotex Pharmachem Inc
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Priority to CA002510093A priority Critical patent/CA2510093C/en
Publication of CA2510093A1 publication Critical patent/CA2510093A1/en
Application granted granted Critical
Publication of CA2510093C publication Critical patent/CA2510093C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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    • 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
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/22—Aliphatic unsaturated hydrocarbons containing carbon-to-carbon triple bonds
    • 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
    • C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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

Abstract

A process for the conversion of ketones of general formula (1) to .alpha.- vinylchlorides (2) and .alpha.,.alpha.-dichloro (3) compounds using phosphorus oxychloride together with a trialkylamine base and catalyst wherein R is a cyclic or acyclic C1 to C6 alkyl, aryl, or C7 to C10 aralkyl and R' is hydrogen, cyclic or acyclic C1 to C6 alkyl, aryl, or C7 to C10 aralkyl. The .alpha.-vinylchloride (2) and .alpha.,.alpha.-dichloro (3) compounds can then be converted to their corresponding acetylene (4) upon treatment with an alkyl sufoxide or sulfone solvent in the presence of a strong base and extracting of the acetylene (4) by using an organic solvent.
CA002510093A 2005-06-16 2005-06-16 Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones Expired - Fee Related CA2510093C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002510093A CA2510093C (en) 2005-06-16 2005-06-16 Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA002510093A CA2510093C (en) 2005-06-16 2005-06-16 Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones

Publications (2)

Publication Number Publication Date
CA2510093A1 true CA2510093A1 (en) 2006-12-16
CA2510093C CA2510093C (en) 2009-09-29

Family

ID=37545764

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002510093A Expired - Fee Related CA2510093C (en) 2005-06-16 2005-06-16 Novel process for the preparation of.alpha.-chlorovinyl, .alpha.,.alpha.-dichloro, and acetylenes from ketones

Country Status (1)

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CA (1) CA2510093C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104193689A (en) * 2014-07-23 2014-12-10 大连理工大学 Method for synthesizing erlotinib hydrochloride
WO2024146006A1 (en) * 2023-01-03 2024-07-11 凯莱英生命科学技术(天津)有限公司 Preparation method and purification method for 2,2-dichloropropane

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* Cited by examiner, † Cited by third party
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US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
CA2532367C (en) 2003-07-15 2013-04-23 Grt, Inc. Hydrocarbon synthesis
US20050171393A1 (en) 2003-07-15 2005-08-04 Lorkovic Ivan M. Hydrocarbon synthesis
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US20060100469A1 (en) 2004-04-16 2006-05-11 Waycuilis John J Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7244867B2 (en) 2004-04-16 2007-07-17 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US20080275284A1 (en) 2004-04-16 2008-11-06 Marathon Oil Company Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
KR101433781B1 (en) 2006-02-03 2014-08-25 리액션 35, 엘엘씨 System and method for forming hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
AU2008256606A1 (en) 2007-05-24 2008-12-04 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104193689A (en) * 2014-07-23 2014-12-10 大连理工大学 Method for synthesizing erlotinib hydrochloride
CN104193689B (en) * 2014-07-23 2017-02-08 大连理工大学 Method for synthesizing erlotinib hydrochloride
WO2024146006A1 (en) * 2023-01-03 2024-07-11 凯莱英生命科学技术(天津)有限公司 Preparation method and purification method for 2,2-dichloropropane

Also Published As

Publication number Publication date
CA2510093C (en) 2009-09-29

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