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Halogen compound oxo reaction method

A carbonylation reaction and halide technology, which is applied in the field of halide carbonylation, can solve the problems of poor water solubility of long-chain alkyl quaternary ammonium salts, low recycling utilization rate, large loss of main catalyst, etc., and achieves good water solubility. , The effect of improved adsorption performance and excellent biodegradability

Active Publication Date: 2008-03-12
陕西高安绿能生物化工有限公司
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Problems solved by technology

The use of these phase transfer catalysts has a large amount of use, and the recovery and recycling rate is low, resulting in a large loss of the main catalyst. At the same time, these quaternary ammonium salts have varying degrees of toxicity, and environmental protection is difficult. Some long-chain alkyl quaternary ammonium salts have poor solubility. Defects such as easy decomposition and failure in strong alkaline reaction system

Method used

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Examples

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Embodiment 1

[0028] 2-undecyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride is used as a phase transfer catalyst, and benzyl chlorocarbonylation reaction is used to synthesize phenylacetic acid (refer to literature for the synthesis method of phase transfer catalyst: Shi Zhen, Yang Weiguo . Synthesis of Dihydroxyethylimidazoline Cationic Surfactant. Chemical World, 1994, 1: 14-15).

[0029] Catalyst Carbonyl cobalt salt Co(CO) 4 - Synthesis of: Add 0.286g (0.0012mol) CoCl to a 100mL three-neck flask 2 ·6H 2 O, 15mL tetrahydrofuran, pass into CO, add 0.095g (0.0025mol) NaBH in batches 4 , continue to react for 2 hours under the reaction condition of 0-5°C, at this time, the reaction solution is a blue clear solution (cobalt carbonyl salt with better catalytic performance is a green clear solution, without black precipitate).

[0030] Add 1.2 mmol of 2-undecyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride phase transfer catalyst and 10 mL of 30% NaOH aqueous solution to the prepared cobalt...

Embodiment 2

[0032] 2-nonyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride is used as a phase transfer catalyst, and benzyl chlorocarbonylation reaction is used to synthesize phenylacetic acid:

[0033] Add 1.2 mmol of 2-nonyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride phase transfer catalyst and 10 mL of 30% NaOH aqueous solution to the prepared cobalt carbonyl salt, and react at room temperature for 5 min. A solution of 40 mmol benzyl chloride in tetrahydrofuran (30 mL) was added dropwise, and the solution was completed in about 15 minutes, and reacted at 50° C. for 2.5 hours. The organic phase was removed, the aqueous phase was adjusted to acidity with 10% hydrochloric acid solution, and the solution became a pink clear solution. Extract with ether (15mL×3), combine ether extracts, anhydrous MgSO 4 Dry, and recover the phase transfer catalyst solution in the aqueous phase. After filtration and concentration under reduced pressure, phenylacetic acid was precipitated. The product was wh...

Embodiment 3

[0035] 2-nonyl-1-bis(2-hydroxyethyl)-2-imidazoline chloride is used as a phase transfer catalyst, and benzyl chlorocarbonylation reaction is used to synthesize phenylacetic acid:

[0036] Similar to Example 2, except that: the phase transfer catalyst solution recovered in Example 2 and 5 mL of 30% NaOH aqueous solution were added to the prepared cobalt carbonyl salt, and the rest of the reaction conditions were the same. The yield of phenylacetic acid was 52%, and the purity was 99%. The NMR, mass spectrometry, infrared and elemental analysis data were consistent with those reported in the literature.

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Abstract

The present invention discloses a method of the halide carbonylation reaction. The key point of the technology is that the reaction uses a novel phase transfer catalyst 2-alkyl-1- 2 (2- hydroxyethyl)-2-chlorine imidazoline; the catalyst has the good catalytic performance for the carbonylation of the benzyl halogen, alpha-alkyl benzyl halogen and so on through the NaCo(CO)4; the phase transfer catalyst has the advantages of the good water-soluble performance, the good biodegradable performance, the low toxicity, the high efficiency of being recycled and reused, and so on.

Description

technical field [0001] The invention relates to a method for the carbonylation reaction of halides. A novel phase transfer catalyst is used in the carbonylation reaction of halides. This type of phase transfer catalyst can be effectively used for the carbonylation reaction of producing corresponding carboxylic acids from halides, which belongs to organic chemistry. technology field. Background technique [0002] Carbon monoxide is the main air pollutant in the atmosphere. Extensive emissions of carbon monoxide from vehicle exhaust and coke oven gas have seriously threatened the harmony of nature. The use of carbonylation reaction to introduce carbon monoxide into organic compound molecules is a hot spot in chemical industry application research, and it is also one of the most effective methods in organic synthetic chemistry to replace natural forces to transform inorganic substances into organic substances. The synthesized products can be widely used. Aldehydes, ketones, es...

Claims

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Application Information

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IPC IPC(8): C07C51/10C07C57/32C07C57/58C07D307/54C07B41/08B01J31/02
Inventor 李剑利郭媛史真
Owner 陕西高安绿能生物化工有限公司
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