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A novel synthetic method of 5-bromo-1-pentene
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A technology for pentene and chemical synthesis, applied in chemical instruments and methods, preparation of halogenated hydrocarbons, preparation of dehydrohalogenation, etc., can solve the problem that 4-pentene-1-ol raw materials are not easily available, high price, and no production scale-up. significance and other issues, to achieve the effect of low price, easy operation and simplified post-processing
Active Publication Date: 2020-06-12
浦拉司科技(上海)有限责任公司
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Problems solved by technology
[0016] But in this synthesis method, the raw material of 4-penten-1-ol is not easy to obtain, it needs custom synthesis, and the price is very high, so the production scale-up is meaningless
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Embodiment 1
[0032] 100KG of 1,5-dibromopentane, 200KG of N,N-dimethylformamide, stirred and mixed, then heated in an oil bath at 150°C for 6h, distilled at atmospheric pressure to collect fractions, washed twice with 100KG saturated brine, and the upper layer The organic liquid was rectified to obtain 32.6KG, yield 50.2%, content: 99%.
[0033] The product was tested and confirmed to be 5-bromo-1-pentene with a purity of 99% (GC). Among them, the product's 1H NMR (400MHz, CDCl3) δ: 1.96 (m, 2H) 2.22 (m, 2H), 3.43 (t,2H), 5.02~5.12(m,2H), 5.80(m,1H).
Embodiment 2
[0035] 100KG of 1,5-dibromopentane, 100KG of N,N-dimethylformamide, and 6.2KG of hexamethylphosphoric triamide were stirred and mixed, then heated in an oil bath at 140°C for 4 hours, and distilled at atmospheric pressure to collect fractions. Washed twice with 100KG brine, the organic liquid in the upper layer was rectified to obtain 52.0KG, yield 80.1%, content: 99%.
[0036] The product was tested and confirmed to be 5-bromo-1-pentene with a purity of 99% (GC). Among them, the product's 1H NMR (400MHz, CDCl3) δ: 1.96 (m, 2H) 2.22 (m, 2H), 3.43 (t,2H), 5.02~5.12(m,2H), 5.80(m,1H).
Embodiment 3
[0038] 1,5-dibromopentane 100KG, N,N-dimethylformamide 200KG, hexamethylphosphoric triamide 3.1KG were stirred and mixed, then heated in an oil bath at 150°C for 4h, distilled at atmospheric pressure to collect fractions, the collected fractions Washed twice with 100KG brine, the organic liquid in the upper layer was rectified to obtain 46.7KG, yield 71.9%, content: 99%.
[0039] The product was tested and confirmed to be 5-bromo-1-pentene with a purity of 99% (GC). Among them, the product's 1H NMR (400MHz, CDCl3) δ: 1.96 (m, 2H) 2.22 (m, 2H), 3.43 (t,2H), 5.02~5.12(m,2H), 5.80(m,1H).
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Abstract
The invention relates to the technical field of an organic synthetic method, particularly to a new chemical synthetic method of 5-bromo-1-pentene. According to the method, 1,5-dibromopentate is takenas an initial raw material, N,N-dimethyl formamide is taken as a solvent, and heating is performed; hexamethylphosphoramide is used as a catalyst, a reaction is carried out, and normal pressure distillation is carried out to obtain a coarse 5-bromo-1-pentene product; and the coarse product is washed with brine for two times, and rectification is performed to obtain high-purity 5-bromo-1-pentene. Compared with a method in the prior art, the method is simplified in synthetic process and post-treatment. The reaction yield is increased, the production stability is improved, and the production costis reduced.
Description
technical field [0001] The invention relates to the technical field of organic synthesis methods, in particular to a novel chemical synthesis method of 5-bromo-1-pentene. Background technique [0002] 5-bromo-1-pentene (5-bromo-1-penten), molecular formula C5H9Br, molecular weight is 149.03, colorless transparent liquid, molecular structural formula is: [0003] [0004] The molecular structure contains both double bonds and bromine atoms, so it has the properties of olefins and halogenated hydrocarbons. It is the starting material for the synthesis of DL-histrionicotoxin and benzophenone-containing fatty acids. It is a basic chemical industry. Pharmaceutical intermediates are widely used in the fields of medicine, pesticides and material chemistry. [0005] At present, the commonly used synthetic methods of 5-bromo-1-pentene mainly contain the following: [0006] 1) U.S. Patent US5563230 uses 1,5-dibromopentane as a raw material, heats it with hexamethylphosphoric tria...
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