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Process for synthesizing halogenated compounds by oxygenizing and halogenating reaction

A synthesis method and compound technology, applied in organic chemistry methods, chemical instruments and methods, organic halogenation, etc., to achieve the effect of improving atom economy and efficiency

Inactive Publication Date: 2008-11-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Ca[V(HIDPA) by Pombeiro et al. 2 ] is the catalyst HBr-H 2 o 2 Oxidation of cyclohexane bromide, but only about 10% yield [Reis P.M.; Silva J.L.; Fraústo da Silva J.J.R.; Pombeiro A.J.L., Chem.Commun., 2000, 1845-1846.]

Method used

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  • Process for synthesizing halogenated compounds by oxygenizing and halogenating reaction
  • Process for synthesizing halogenated compounds by oxygenizing and halogenating reaction
  • Process for synthesizing halogenated compounds by oxygenizing and halogenating reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 20g of n-hexane, 9.4g of 40% hydrogen bromide and 1.0g of catalyst MnO 2 , stirred and heated to reflux, then slowly added 70g of 5% NaClO with a peristaltic pump, and reacted for 15 hours until the color of bromine in the reaction liquid basically faded, and the reaction was stopped. The organic layer was separated, washed with sodium bisulfite solution, sodium bicarbonate solution and saturated brine respectively, dried over anhydrous magnesium sulfate, and n-hexane was distilled off under reduced pressure to obtain 2-bromo and 3-bromo-n-hexane Product (colorless liquid). The yield was 76%, and the ratio of 2-bromo and 3-bromo was determined to be 3:2 by 500 M NMR.

Embodiment 2

[0050] 20g of isooctane, 9.4g of 40% hydrogen iodide and 0.5g of catalyst bentonite, stirred and heated at 120°C for reaction, then slowly added 7g of KMnO with a peristaltic pump 4 , and reacted for 5 hours until the color of bromine in the reaction solution basically faded away, and the reaction was stopped. The organic layer was separated, washed with sodium bisulfite solution, sodium bicarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain 2-bromoisooctane product (colorless liquid). The yield is 54%.

Embodiment 3

[0052] 20g of cyclohexane, 9.4g of 40% hydrogen bromide and 1.5g of catalyst diatomaceous earth, stirred and heated at 70°C, then slowly added 1.5 equivalents of 30% hydrogen peroxide with a peristaltic pump, and reacted for 10 hours until the reaction liquid The color of the bromine basically fades away and the reaction stops. The organic layer was separated, washed with sodium bisulfite solution, sodium bicarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain n-hexane bromide (colorless liquid). The boiling point is 166°C, and the yield is 97%.

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Abstract

The invention discloses a method for synthesizing halogenated compound through oxidation-halogenating reaction. The method is as follows: in the presence of an oxidizing agent and catalyst, compound SH and halide MXn as shown in formula (II) are fully reacted at a temperature of between 10 DEG C below zero and 180 DEG C in the presence of excessive compound SH or added organic solvent, and the reaction liquid undergoes post treatment so as to obtain halogenated compound SX; the halide (II) is added in the form of an aqueous solution; the compound SH is straight-chain or branched-chain alkane with the carbon number of between C1 and C30, polymethylene with the carbon number of between C3 and C30, alkyl substituted polymethylene with the carbon number of between C1 and C10, alkyl substituted arene with the carbon number of between C1 and C10, heterocyclic compound with the carbon number of between C2 and C30 or alkyl substituted heterocyclic compound with the carbon number of between C1 and C10; and the X in the halide MXn is Cl, Br or I, while the M is H, Na, K, Ca or Mg. The method has simple making steps, no three-waste pollution and as high as more than 90 percent of yield.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing a halogenated compound by halogenating a compound represented by formula (I). (2) Background technology [0002] Halogenated alkanes are a very important class of synthetic intermediates in the chemical industry. Although there are various methods for the synthesis of haloalkanes, the direct halogenation of alkanes to haloalkanes is obviously the ideal route. People have developed many methods for the halogenation of alkanes, such as halogenation with halogens, N-X compounds, polyhalogenated alkanes and so on. However, due to the low reactivity of alkanes, there are not many efficient bromination methods for alkanes. [0003] Li C-Z reported that under the action of manganese dioxide, elemental bromine can achieve the monobromination reaction of cyclohexane well (the yield is as high as 99%). Catalyst MnO 2 Can be easily recovered and reused without further activation. [0004] [0005] The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B39/00C07C17/093C07D333/28C07D307/56
Inventor 李郁锦高建荣贾建洪韩亮盛卫坚居洁
Owner ZHEJIANG UNIV OF TECH