Method for preparing halogenated hydrocarbons from strong acidic ionic liquid

An ionic liquid and strong acidic technology, which is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, organic chemistry, etc., can solve the problems of difficult protonation of alcoholic hydroxyl groups, long reaction time, high reaction temperature, etc., and achieve high product yield, The effect of fast reaction rate and easy separation

Inactive Publication Date: 2010-07-07
ZHENGZHOU UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0033] Tang Jie, Sun Jing and others used the acid-type ionic liquid [Hmim] + x - (X=Cl, Br, the method [CN: 1440958A, 2003.9.10] that primary alcohol or cyclohexanol in I) is converted into haloalkane to prepare halohydrocarbon, the characteristics of this method have highlighted the advantage of ionic liquid, after the reaction, ionic liquid can be Recycling, but it is directly neutralized with imidazole and hydrohalic acid to obtain ionic liquid [Hmim]X, its acid strength is very low, and it is very difficult to protonate the alcoholic hydroxyl group, so when using this type of ionic liquid for halogenation reaction, its The reaction temperature is high, the reaction time is long, and the product yield is also low

Method used

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  • Method for preparing halogenated hydrocarbons from strong acidic ionic liquid
  • Method for preparing halogenated hydrocarbons from strong acidic ionic liquid
  • Method for preparing halogenated hydrocarbons from strong acidic ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] In the reaction system, add 0.2 mol of 1,7-heptanediol, 0.5 mol of 1-ethyl 3-methylimidazolium bromide [emim] Br, 0.5 mol of 1-ethyl-3-methylimidazolium bisulfate [emim] HSO 4 0.5mol, reaction temperature 60~100℃, react for 60min, after the reaction is completed, add a certain amount of water, extract the reaction solution with cyclohexane, wash and dry the organic phase with water, spin off the solvent to obtain the product 1,7-dibromo Heptane, the product yield is 93%. Add 0.5 mol of sodium bromide to the aqueous phase, stir evenly, remove water, add methanol for ion exchange, react for 24 hours, filter out unreacted sodium bromide and sodium sulfate, and spin evaporate the solvent to obtain the ionic liquid [ emim]Br is recycled.

Embodiment 2

[0059] In the reaction system, add 0.1 mol of n-octanol, 0.1 mol of 1-propyl 3-methylimidazolium chloride [pmim]Cl, 0.1 mol of 1-propyl-3-methylimidazolium bisulfate [pmim] HSO 4 0.1mol, reaction temperature 60~100℃, reaction 120min, after the reaction is completed, add a certain amount of water, extract the reaction solution with cyclohexane, wash and dry the organic phase with water, spin off the solvent to obtain 1-chlorooctane, the product yield The rate is 82%. Add 0.2mol of sodium chloride to the water phase, and the others are the same as in Example 1.

Embodiment 3

[0061] In the reaction system, add 1,7-heptanediol 0.2mol, 1-isopropyl 3-methylimidazolium iodide [ipmim]I 0.4mol, 1-isopropyl-3-methylimidazolium bisulfate [ipmim] ] HSO 4 0.4mol, nitrogen protection, reaction temperature 60 ~ 100 ℃, reaction 30min, after the reaction, add a certain amount of water, extract the reaction solution with cyclohexane, wash and dry the organic phase, spin off the solvent to obtain 1,7 -Diiodoheptane, the product yield is 90%. Add 0.5mol of sodium iodide to the aqueous phase, and the others are the same as in Example 1.

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Abstract

The invention discloses a new method for preparing halogenated hydrocarbons, which belongs to the technical field of fine chemical synthesis. In the method, strong acidic ionic liquid is used as a halogenated agent, a catalyst and a solvent and reacts for 30 to 120 minutes at the temperature of between 60 and 100 DEG C to generate the halogenated hydrocarbons. Compared with the current methods, the method has the advantages of green preparation process, high product yield, short technological flow, mild reaction conditions, simple process, easy isolation of the product from the ionic liquid, easy recovery of the ionic liquid from a reaction system, recycling and the like, is favorable for saving energy resources, lowering investment, reducing environmental pollution and the like, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemicals, and relates to a method for synthesizing halogenated hydrocarbon compounds, in particular to a method for preparing medium and long carbon chain halogenated hydrocarbons from strongly acidic ionic liquids. Background technique [0002] At present, the following methods are mainly used for the synthesis of halogenated hydrocarbons by the replacement of alcoholic hydroxyl groups: [0003] 1. Using the thionyl chloride method [0004] [0005] Zhang Zhuyong [Fine Organic Synthesis Unit Reaction M. Shanghai: East China University of Science and Technology Press, 2003.] The space configuration of halogenated products obtained by this method can be maintained, and product classification is easy because only products and sulfur dioxide are produced after the reaction. However, thionyl chloride is very active and unstable, and is usually only used for the chlorination reaction of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C19/01C07C19/07C07C19/075C07C17/16
Inventor 李华朱江章亚东胡国勤赵蕾
Owner ZHENGZHOU UNIV
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