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Synthesis of 2,2,2-trifluoroethanethiol

a technology of trifluoroethanethiol and synthesis process, which is applied in the field of synthesis of 2,2,2-trifluoroethanethiol, can solve the problems that the commercially viable process for synthesizing 2,2,2-trifluoroethanethiol using readily available starting materials has not been described or developed

Inactive Publication Date: 2017-07-27
ARKEMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a method for making CF3CH2SH by reacting CF3CH2X with an alkali metal MSH in an organic solvent. This reaction can be carried out in the presence of a phase transfer catalyst and / or a hydrogen sulfide. The yield of the reaction product mixture includes CF3CH2SH and by-products such as (CF3CH2)2S2 and (CF3CH2)2S. The by-products can be further reacted with a hydrogenating agent to form CF3CH2SH. The technical effect of this invention is a more efficient and improved method for making CF3CH2SH.

Problems solved by technology

However, to date a commercially viable process for synthesizing 2,2,2-trifluoroethanethiol using readily available starting materials has not been described or developed.

Method used

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  • Synthesis of 2,2,2-trifluoroethanethiol
  • Synthesis of 2,2,2-trifluoroethanethiol
  • Synthesis of 2,2,2-trifluoroethanethiol

Examples

Experimental program
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example 1

[0044]This example demonstrates the reaction of 2,2,2-trifluoro-1-chloroethane (HCFC-133a) with NaSH to obtain 2,2,2-trifluoroethanethiol, according to equation 1 below:

[0045]A number of experiments were run in NMP (N-methylpyrrolidone) solvent with varying amounts of NaSH. These experiments were run in a 150 ml Chemglass glass pressure reactor containing a magnetic stir bar and equipped with a pressure gauge and a pressure relief valve. The reactions were heated and stirred using an oil bath on top of an IKA digital hot plate / stirrer. The CF3CH2Cl was bubbled into the reaction mixture sub-surface as a gas. Reactions were typically done on a 3-5 gram (HCFC-133a) scale and conversion was determined by measurement of the 1H NMR signal of HCFC-133a (SM in Table 1) and comparing to the 1H NMR signal of the solvent. The product distribution was determined by comparison of the unique 19F NMR signals for the desired thiol product, CF3CH2SH (I) and the by-products bis-sulfide (CF3CH2)2S (II...

example 2

[0047]Using similar methodology as described in Example 1, the nucleophilic displacement of the tosylate (OTs=p-toluenesulfonate) group from CF3CH2OTs using the nucleophile SH− (supplied from NaSH) was investigated as a route to prepare the target compound (I), CF3CH2SH, according to equation 2 below:

Experiments were run in NMP solvent and the results are summarized in Table 2 below.

TABLE 2Summary of Results of Reactions of CF3CH2OTswith NaSH in NMP (N-methylpyrrolidone) Solvent1H NMRProduct Distribution (Mol %)NaHSMax.Max.Time%from 19F NMRExpt.Equiv.Temp.psig(hours)Conv.SMIIIIII2a18043951925562b4900310005347

example 3

[0048]Using similar methodology as described in Example 1, the nucleophilic displacement of the chlorine atom from HCFC-133a, CF3CH2Cl, using the nucleophile SH− (supplied from NaSH) was investigated in a variety of polar solvents. All reactions were run in a 150 ml Chemglass reactor with magnetic stirring and heated at 90° C. for three hours. HCFC-133a was introduced sub-surface to the solvent. A one mol excess of NaSH-H2O was used for all experiments. The results are summarized in Table 3 below. Product distribution is expressed in mol % and was determined by 19F NMR spectroscopy.

TABLE 3Summary of Results of Reactions of HCFC-133a with NaSH in differentsolventsProduct Distribution (Mol %)from 19F NMRExpt.SolventThiolbis-sulfidebis-disulfide3aDMSO1958233bDMSO*2844273cDimethylacetamide504463dNMP445153eDMF47476

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Abstract

A method of making CF3CH2SH, comprising a step of reacting CF3CH2X, wherein X is halide or tosylate, with MSH, where M is an alkali metal such as Na or K, to yield CF3CH2SH. More specifically, a method of making CF3CH2SH, a step of reacting CF3CH2CI with a molar excess of NaSH in a reaction medium of one or more polar organic solvents at a temperature of from about 70 C to about 110 C for a time of from about 1 to about 5 hours.

Description

FIELD OF THE INVENTION[0001]The invention relates to methods for synthesizing 2,2,2-trifluoroethanethiol (CF3CH2SH), which is a useful etchant for electronics applications.DISCUSSION OF THE RELATED ART[0002]The fluorothiol compound 2,2,2-trifluoroethanethiol, which has the chemical structure CF3CH2SH, has utility as an etchant in the manufacture of various electronic products and as an intermediate in the synthesis of various organic compounds. It is also useful in creating self-assembled monolayers on electrode surfaces and the like. However, to date a commercially viable process for synthesizing 2,2,2-trifluoroethanethiol using readily available starting materials has not been described or developed.BRIEF SUMMARY OF THE INVENTION[0003]One aspect of the present invention provides a method of making CF3CH2SH, comprising a step of reacting CF3CH2X, wherein X is a leaving group selected from the group consisting of halide and tosylate, with MSH, wherein M is an alkali metal. For examp...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C319/02
CPCC07C319/02C07C323/03C07C319/26
Inventor SYVRET, ROBERT GEORGEPOLSZ, CRAIG ALANSWAN, DANA LEESRINIVAS, VIJAY R.
Owner ARKEMA INC
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