Preparation method of pentafluoropentanol

A technology of pentafluoropentanol and pentanol, which is applied in the field of preparation of synthetic intermediates, can solve problems such as difficulty in realizing industrialization, small pentafluoropentanol, and difficult control of the reaction process, and achieve high reaction yield and easy industrial production Effect

Inactive Publication Date: 2017-12-22
天津长芦华信化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the disadvantage of this process route is that the reaction process is not easy to control, and it is difficult to realize industrializati

Method used

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  • Preparation method of pentafluoropentanol
  • Preparation method of pentafluoropentanol

Examples

Experimental program
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Embodiment 1

[0044] (i) Add 110g of allyl alcohol and 500g of pentafluoroiodoethane into the autoclave, add 15g of azobisisobutyronitrile, add 800ml of water, control the temperature at 30°C~40°C, and stir for 4h~8h. After the reaction was completed, the lower organic phase was separated by standing. The organic phase was washed with water and dried to obtain 600 g of 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol with a purity of 90%.

[0045] (ii) Add 50g of azobisisobutyronitrile to 500g of 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol, slowly add 40g of platinum oxide catalyst, and control the reaction temperature to 60°C ~70℃, react for 3h-4h. After the reaction was completed, the upper organic phase was left standing to separate to obtain the pentafluoropentanol product with a quality of 260 g. The product was purified by rectification to obtain a pentafluoropentanol product with a purity greater than 99%.

Embodiment 2

[0047] (i) Add 110g propenyl alcohol and 600g pentafluoroiodoethane into the autoclave, add 20g cumene hydroperoxide, add 700ml water, 100ml acetonitrile, control the temperature at 40°C~50°C, and stir for 4h~8h. After the reaction, the lower organic phase was separated by standing. The organic phase was washed with water and dried to obtain 610 g of 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol with a purity of 89%.

[0048] (ii) Add 40g of azobisisoheptanonitrile to 500g of 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol, slowly add 40g of 5% palladium-carbon catalyst to control the reaction The temperature is 60°C~70°C, and the reaction time is 3h-4h. After the reaction was completed, the pentafluoropentanol product was obtained by filtration, with a quality of 260 g. The product was purified by distillation to obtain a pentafluoropentanol product with a purity greater than 99%.

Embodiment 3

[0050] (i) Add 110g of allyl alcohol and 400g of pentafluoroiodoethane into the autoclave, add 50g of ammonium persulfate, 25g of sodium bisulfite, add 900ml of water, control the temperature at 50°C~70°C, and stir for 4h~8h. After the reaction was completed, the lower organic phase was separated by standing. The organic phase was washed with water and dried to obtain 600 g of 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol.

[0051](ii) Add 30g of azobisisobutyronitrile to 500g of 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol, slowly add 50g of palladium acetate, and control the reaction temperature to 60℃~ 70°C, react for 3h-4h. After the reaction was completed, the pentafluoropentanol product was obtained by filtration, with a quality of 260 g. The product was purified by distillation to obtain a pentafluoropentanol product with a purity greater than 99%.

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Abstract

The invention discloses a preparation method of pentafluoropentanol. The preparation method comprises the following steps: firstly, synthetic reaction: carrying out a reaction between propenol and pentafluoroethyliodide under the action of a free radical initiator to generate 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol; secondly, hydrogenated dehalogenation reaction: carrying out the hydrogenated dehalogenation reaction under the action of the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol to generate a pentafluoropentanol product. The invention provides the preparation method of the pentafluoropentanol. The pentafluoroethyliodide and the propenol serving the raw material undergo free radical reaction to generate the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol, and the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol undergoes dehalogenation reaction under the action of a reducing agent to generate the pentafluoropentanol. The method is high in reaction yield and easy for industrial production; in addition, the purity of the product is higher than 99 percent.

Description

technical field [0001] The invention belongs to a preparation method of a synthetic intermediate, in particular to a preparation method of pentafluoropentanol. Background technique [0002] Pentafluoropentanol, the molecular formula is C 5 h 7 f 5 O, the main use is anti-tumor drug intermediates, and the downstream products are the production of pentafluoropentanol. In recent years, pentafluoropentanol has been used in the intermediates of new high-efficiency drug synthesis and the preparation of some drugs. It is also a surfactant, functional material, Inert liquids and synthetic intermediates in the dye industry, with a wide range of uses. [0003] There are three main preparation techniques for pentafluoropentanol reported in the literature, two of which are based on pentafluoroiodoethane and propenyl alcohol as raw materials. The first process route uses sodium dithionite / sodium bicarbonate mixture as a free radical initiator to generate 4,4,5,5,5-pentafluoro-2-iodo-...

Claims

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Application Information

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IPC IPC(8): C07C29/58C07C31/38
CPCC07C29/58C07C29/62C07C31/38C07C31/36
Inventor 陈俭月仝庆崔学文龚振礼张彬彬
Owner 天津长芦华信化工股份有限公司
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