Production method of fluoroalkyl iodide

A technology of fluoroalkyl iodide and alkyl, which is applied in the field of preparation of fluoroalkyl iodide, and can solve the problems of high cost, low cost, and difficult availability of raw materials

Active Publication Date: 2020-02-07
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a method for the preparation of fluoroalkyl iodides. The raw materials used in this method are easy to obtain and relatively cheap

Method used

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  • Production method of fluoroalkyl iodide
  • Production method of fluoroalkyl iodide
  • Production method of fluoroalkyl iodide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087]

[0088] Add 100mL of THF solution to a 250mL open beaker containing a stirring bar, weigh 1.14g (0.03mol) of sodium borohydride and add it; adjust the rotor speed to about 800 rpm (too low to produce foam that affects the reaction effect), Load 15g (0.03mol) of the sulfonyl fluoride raw material represented by the formula (IV-1) weighed on the automatic injection pump of the 10mL syringe; After the addition was completed, the reaction was carried out at room temperature for 2 h. After the fluorine spectrum detection reaction is complete, add SO 2 Cl 2 (0.06mol) was reacted at room temperature for 30 minutes, and the reaction was complete by fluorine spectrum detection. Add water 50mL to wash subsequently, add 5g KI reaction again, heat to 80 ℃ reflux 2h, get the perfluorooctyl iodide shown in formula (I-1) after distilling off solvent tetrahydrofuran, total yield is 75%, purity>92 %.

Embodiment 2

[0090] (1)

[0091]

[0092] Add 2Kg (3.34mol) of the substrate represented by formula (IV-2) and 4.5Kg of acetonitrile into a 20L four-necked reaction flask. Heat up while stirring, control the internal temperature to 70°C, add 279g (7.34mol) NaBH in batches 4 , observe the change of internal temperature, control the internal temperature not to exceed 75°C, react at room temperature for 3 hours, detect the reaction by fluorine spectrum, after the reaction is completed, add 108g of water dropwise to quench the excess NaBH 4 . After the reaction, filter with suction, wash the filter cake with DCM, and dry at 40°C to obtain the sodium salt of sulfinic acid represented by formula (III-2), with a yield of about 90%.

[0093] (2)

[0094]

[0095]Add 3000mL of sulfuryl chloride into the 10L reaction flask, cool down to about 10°C in a dry ice bath, add 1960g (3.23mol) of sulfinic acid sodium salt shown in formula (III-2) in batches while stirring, a large amount of gas is ...

Embodiment 3

[0100] (1)

[0101]

[0102] Add 89.2g (0.2mol) of the sulfonyl fluoride raw material represented by formula (IV-3) and 200mL of ethanol into a 500mL three-neck flask, cool down in an ice-water bath, and when the internal temperature is lower than 5°C, add NaBH in batches 4 , Control the internal temperature not to exceed 10°C. Add 7.56g (0.2mol) NaBH 4 Then take a sample for F-spectrum detection, add 0.76g (0.02mol) corresponding amount of NaBH 4 Complete reaction of raw materials while avoiding NaBH 4 excess. Ethanol was distilled off under reduced pressure. The product represented by formula (III-3) was obtained with a fluorine spectrum yield of 97%.

[0103] (2)

[0104]

[0105] Add 200mL dichloromethane and 32mL (0.4mol) SO 2 Cl 2 , fully stirred to make the reaction system into a uniform white emulsion, react at room temperature for 2 hours, and take samples to check whether the reaction of the raw materials is complete. After all the raw materials have b...

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Abstract

The invention discloses a production method of a fluoroalkyl iodide, and particularly discloses a production method of a fluoroalkyl iodide as shown in a formula (I) as shown in the specification. Theproduction method of the fluoroalkyl iodide as shown in the formula (I) as shown in the specification comprises the following step: in a first solvent, subjecting a compound as shown in a formula (II) as shown in the specification and an iodide to an iodination reaction as shown in the specification. The raw materials used in the method are easy to obtain, and prices are low; and the method is high in conversion rate and yield, and the tolerability to functional groups is high.

Description

technical field [0001] The present invention relates to the preparation method of fluoroalkyl iodide. Background technique [0002] Fluorine-containing iodoalkanes are an important class of organic fluorine-containing intermediates, and are the main raw materials for the production of fluorine-containing surfactants, fluoroether rubbers, fluorine-containing fabric finishing agents and other fluorine-containing fine chemicals. Fluorine-containing compounds have high surface It has the characteristics of activity, high weather resistance, high chemical stability and water and oil repellency, and is widely used in chemical industry, materials, electronics, military industry, aerospace and other industries. [0003] Since 3M launched fluorine-containing surfactants in 1956, companies in the United States, Europe, and Japan have also launched a wide variety of products, mainly including 3M and DuPont in the United States, Hoechst and Bayer in Germany, and Neos in Japan. The abov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/093C07C19/16C07C303/02C07C309/82C07C309/80C07C41/26C07C43/12C07C315/00C07C317/18C07C317/04
CPCC07C17/093C07C19/16C07C303/02C07C309/82C07C309/80C07C41/26C07C43/12C07C315/00C07C317/18C07C317/04
Inventor 肖吉昌杜若冰
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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