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A kind of preparation method of 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative

A technology of tetrafluorobutane and its derivatives, which is applied in the field of preparation of fluorine-containing compounds, can solve the problems of large amount of catalysts and many wastes in the reaction, and achieve the effect of less wastes

Active Publication Date: 2017-04-12
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The telomerization method using dichlorofreon as a raw material is an important means of preparing fluorine-containing cyclopropane derivatives. The document Org.Lett.2012,14(24), 6214-6217 reported that styrene (2mmol) and CF 3 CHCl 2 (4mL) in Cu (3mmol) and Et 2 Under the catalysis of NH (10mmol), carry out purification and synthesis with column chromatography to obtain 2,4-dichloro-trifluorobutylbenzene. This method has a large amount of catalyst and many reaction wastes

Method used

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  • A kind of preparation method of 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative
  • A kind of preparation method of 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative
  • A kind of preparation method of 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative

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Effect test

Embodiment 1

[0019] Add 2.8 grams of copper chloride and 6.4 grams of 2,2-bipyridine to a 500 mL titanium alloy belt stirred autoclave, dissolve them in 50 mL of acetonitrile, replace the air in the kettle with nitrogen, and inject 340 grams of CF with nitrogen gas 3 CFCl 2 and 52 grams of styrene, the reaction temperature is 120°C, and the reaction time is 10 hours. After the reaction, the crude product is removed by atmospheric distillation. 2 ClCF 2 Cl and acetonitrile were recycled and continued to be distilled under reduced pressure to collect 1,1,1,2-tetrafluoro-2,4-dichloro-4-butylbenzene, with a conversion rate of 78.3% and a selectivity of 90.2%.

Embodiment 2～7

[0021] Examples 2-7 Prepare 1,1,1,2-tetrafluoro-2,4-dichloro-4-butylbenzene according to the same preparation method as in Example 1, except that the reaction catalyst in Example 1 It is cupric chloride, and copper element, cupric chloride, cuprous chloride, cupric bromide or cuprous iodide are respectively in embodiment 2~7. The reaction results of Examples 2-7 are shown in Table 1.

[0022] Table 1 Effects of catalysts and catalytic promoters

[0023]

Embodiment 8～13

[0025] Examples 8-13 Prepare 2,4-dichloro-1,1,1,2-tetrafluorobutane derivatives according to the same preparation method as in Example 1, except that styrene is used as a raw material in Example 1 , while the raw materials used in Examples 8-13 are respectively naphthalene ethylene, methyl styrene, n-hexene, isooctene, vinyl chloride and propenyl alcohol. The reaction results of Examples 8-13 are shown in Table 2.

[0026] Table 2 The reaction results of different kinds of alkenes

[0027] Example Olefin Reaction temperature °C solvent Conversion rates selectivity 8 n-hexene 100 Acetonitrile 80.2 96.7 9 naphthalene vinyl 100 Acetonitrile 75.6 95.3 10 methyl styrene 76 Acetonitrile 73.3 94.8 11 Isooctene 85 Acetonitrile 79.5 90.5 12 vinyl chloride 130 Dimethyl sulfoxide 50.2 69.1

[0028] 13 Acryl alcohol 120 Methanol 45.7％ 81.4％

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Abstract

The invention discloses a preparation method of a 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative. According to the invention, 2,2-dichloro-1,1,1,2-tetrafluoroethane (CF3CFCl2) or 1,2-dichloro-1,1,2,2-tetrafluoroethane (CF2ClCF2Cl) and CH2=CHR are adopted as raw materials; and under the existence of a telomerization catalyst, a catalyst additive and a solvent, the 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative is prepared. The telomerization catalyst is copper chloride or cuprous chloride. The catalyst additive is 2,2-bipyridine, pentamethyl diethylene triamine, tris(2-pyridylmethyl)amine or tris(2-dimethylaminoethyl)amine. The solvent is acetonitrile, methanol or dimethyl sulfoxide. The invention provides the novel synthesis route with less three-waste generation and high catalytic efficiency. The method is mainly used for preparing the 2,4-dichloro-1,1,1,2-tetrafluorobutane derivative.

Description

technical field [0001] The invention relates to a preparation method of fluorine-containing compounds, in particular to a preparation method of 2,4-dichloro-1,1,1,2-tetrafluorobutane derivatives. Background technique [0002] In the past few decades, the research on the synthesis of fluorine-containing compounds has been a hot area of ​​concern for chemists. As the element with the strongest electron-attracting ability, fluorine atom can form a strong C-F bond with carbon atom, and its atomic radius is similar to that of hydrogen atom. After the atom is introduced into organic matter, it can significantly change the physical and chemical properties of the compound. active. [0003] Fluorine-containing organic substances have been widely used in chemical drugs, pesticides, photoelectric materials and other fields, but most of the existing organic fluorine-containing substances do not exist in nature and need to be synthesized artificially. Therefore, for the research on the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/275C07C19/10C07C22/08C07C29/44C07C31/34
Inventor 吕剑赵波陆居有曾纪珺马辉韩升唐晓博郝志军毛伟张伟王博李凤仙
Owner XIAN MODERN CHEM RES INST