Method for efficiently preparing styrene and deuterated styrene compounds

A styrene-based and styrene-substituted technology, applied in the chemical field, can solve the problems of high reaction temperature, harsh reaction conditions, and low efficiency, and achieve the effects of high synthesis efficiency, mild reaction conditions, and broad application prospects

Pending Publication Date: 2020-09-01
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, scholars at home and abroad have also developed a series of methods for preparing styrene and styrene-substituted compounds from different raw materials (CN 88103864.4, CN 85104804, CN 1244854, WO 2020028399, CN 110813337). These methods have high reaction temperature and high efficiency. Low, not environmentally friendly and many other issues
Such as the Chinese patent application, using waste polystyrene and styrene tar to produce styrene (CN 88103864.4), which adopts the method of cracking to produce styrene monomer, and the cracking temperature needs to be strictly controlled between 360 and 380°C during the preparation process. , the reaction is violent and difficult to control
Another example is the Chinese patent application, the method for preparing styrene (CN 1244854), which discloses a method for selectively preparing styrene, which is carried out by the reaction of acetophenone and hydrogen in the presence of a catalyst, and the reaction temperature is 200-600 ℃, using hydrogen to convert acetophenone into styrene, the method has a higher reaction temperature and harsher reaction conditions

Method used

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  • Method for efficiently preparing styrene and deuterated styrene compounds
  • Method for efficiently preparing styrene and deuterated styrene compounds
  • Method for efficiently preparing styrene and deuterated styrene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] Zn(OTf) 2 (0.002mmol), Zn (0.6mmol) and phenylacetylene (0.2mmol) were sequentially added to a 10mL reaction tube, then 2ml THF (tetrahydrofuran) was added, and heavy water (0.2mmol) was added and sent out of the glove box. Reaction in an oil bath at 60°C, monitored by TLC and I 2 The reaction process is detected by color development. After the reaction is completed, concentrate and pass through the column with silica gel to obtain the deuterated styrene compound, a colorless liquid, with a yield of 91%, 85% (α), 83% (β) deuterium incorporation rate (according to 1 H NMR spectrum to calculate the deuterium incorporation rate of the compound).

[0039] 1 H NMR (400MHz, CDCl 3 ):δ7.42-7.40(m,2H),7.34-7.30(m,2H),7.26-7.23(m,1H),6.75-6.68(m,0.15H),5.79-5.75(m,1H), 5.25-5.22(m,0.17H).

Embodiment 2

[0041]

[0042] Zn(OTf) 2 (0.02mmol), Mn (1.0mmol) and 4-methylphenylacetylene (0.2mmol) were sequentially added to a 10mL reaction tube, then 2ml of 1,4-Dioxane, (dioxane) was added, and heavy water (0.5 mmol) were sent out of the glove box. Reaction in an oil bath at 110°C, monitored by TLC and I 2 The reaction process is detected by color development. After the reaction is completed, concentrate and pass through the column with silica gel to obtain the deuterated styrene compound, a colorless liquid, with a yield of 85%, 90% (α), 89% (β) deuterium incorporation rate .

[0043] 1 H NMR (400MHz, CDCl3 ):δ7.37-7.35(m,2H),7.19-7.17(m,2H),6.77-6.70(m,0.10H),5.77–5.72(m,1H),5.27-5.22(m,0.11H) ,2.39(s,3H).

Embodiment 3

[0045]

[0046] In a water-free and oxygen-free glove box under an argon atmosphere, the ZnI 2 (0.2mmol), In (0.1mmol) and 4-chlorophenylacetylene (0.2mmol) were sequentially added to a 10mL reaction tube, then 2ml of tetrahydropyran was added, and heavy water (1.0mmol) was added and sent out of the glove box. Reaction in 70°C oil bath, monitored by TLC and I 2 The reaction process is detected by color development. After the reaction is completed, concentrate and pass through the column with silica gel to obtain the desired product deuterated styrene compound, a colorless liquid, and the yield is 91%, 92% (α), 90% (β) deuterium Incorporation rate.

[0047] 1 H NMR (400MHz, CDCl 3 ):δ7.35-7.28(m,4H),6.71-6.64(m,0.08H),5.78-5.73(m,1H),5.32-5.25(m,0.10H).

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Abstract

The invention discloses a method for efficiently preparing a styrene compound and a deuterated styrene compound. A phenylacetylene compound and water or heavy water are used as reaction raw materials;lewis acid is used as a catalyst; reacting and synthesizing in an organic solvent under a reducing agent are carried out to obtain a target product styrene compound or deuterated styrene compound; the reaction general formula is disclosed in the invention; the invention provides a method for preparing the styrene compound and the deuterated styrene compound, which is simple, mild, efficient and green to operate; water or heavy water is taken as a hydrogen source and a deuterium source respectively, and the process is green and environment-friendly; in addition, the method is simple and easy to operate, mild in reaction condition and high in synthesis efficiency, the yield of styrene reaches up to 99%, the yield of deuterated styrene reaches up to 99%, the deuterium doping rate reaches upto 98% (alpha) and 96% (beta), and wide application prospects are achieved.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a method for efficiently preparing styrene and deuterated styrene compounds by using water as a hydrogen source and heavy water as a deuterium source. Background technique [0002] Styrene is an important industrial raw material that plays an important role in human production and life. It is mainly used in the manufacture of resins, plastics, and synthetic rubber. According to statistics, from 2013 to 2016, the global styrene production capacity increased by 5.9%. / a, accounting for 17.42%), Western Europe (5.165 million t / a, accounting for 15.19%). It is predicted that by 2020, the global styrene production capacity will exceed 37 million t / a, and China, as the world's largest producer of styrene, will play a major role in it (Tao Xiaoyu, Gong Chao, Li Quan, etc. Styrene market Analysis and Outlook [J]. Chemical Industry, 2018, 36(1): 38-42.). It can be conclud...

Claims

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Application Information

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IPC IPC(8): C07C5/09C07C15/46C07C17/354C07C25/28C07C15/58C07C15/50C07D213/127C07D213/06C07C41/20C07C43/215C07C201/12C07C205/06C07C253/30C07C255/50C07C22/08C07C15/60C07C67/303C07C69/78C07C45/62C07C49/794C07B59/00
CPCC07C5/09C07C17/354C07D213/127C07D213/06C07C41/20C07C201/12C07C253/30C07C67/303C07C45/62C07B59/001C07B59/002C07C2603/24C07C2603/26C07B2200/05C07C15/46C07C25/28C07C15/58C07C15/60C07C15/50C07C22/08C07C43/215C07C205/06C07C255/50C07C69/78C07C49/794
Inventor 周永云樊保敏陈景超和振秀樊瑞峰孙蔚青沈国礼
Owner YUNNAN MINZU UNIV
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