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Perfluoroether type sulfuryl fluoride and sulfonate compounds and synthesis methods thereof

A technology of sulfonate-like compounds and sulfonyl fluoride compounds is applied in the field of perfluoroether sulfonyl fluoride and sulfonate compounds and their synthesis, which can solve the problem of high bioaccumulation and toxicity, low ether bond energy, and application range Limitation and other issues, to achieve the effect of low biological toxicity, low surface tension, and good application value

Pending Publication Date: 2019-07-23
JIANGHAN UNIVERSITY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of product is an ether compound with a carbon chain of (6+2). After it enters the environment as waste, since the ether bond is lower than the bond energy of a carbon-carbon single bond, it is more likely to degrade and break, forming a C 6 - structure of perfluorinated compounds, but with high bioaccumulation and toxicity, the scope of application of such compounds is also subject to certain restrictions

Method used

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  • Perfluoroether type sulfuryl fluoride and sulfonate compounds and synthesis methods thereof
  • Perfluoroether type sulfuryl fluoride and sulfonate compounds and synthesis methods thereof
  • Perfluoroether type sulfuryl fluoride and sulfonate compounds and synthesis methods thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0050] S1: Weigh 80g of n-butanol into a round bottom flask, add 250g (mass fraction: 22%) sodium hydroxide aqueous solution, heat up to 60°C, then add 150g of 1,4-butane sultone, and then heat up to 100 ℃, stirring the reaction for 6h. After the reaction, the volatile components were removed by distillation under reduced pressure, and the residue was dried to obtain the target product as a light yellow solid.

[0051] The target compound is detected by nuclear magnetic resonance, and the detected spectrum is as attached figure 2 As shown, the corresponding test result data is as follows: 1 H NMR (400MHz, CD 3 OD) δ3.46(t, J=12Hz, 2H), 3.44(t, J=12, 4.7Hz, 2H), 2.85(d, J=8.0Hz, 2H), 1.86(m, J=12Hz, 2H ), 1.71(m, J=6.6Hz, 2H), 1.68(m, J=8.4Hz, 2H), 1.40(m, J=4.8Hz, 2H), 0.95(t, J=4.8Hz, 3H). 13 C NMR (400MHz, CD 3 OD) δ71.2, 62.3, 52.2, 32.7, 29.6, 22.8, 20.2, 14.0.C 8 h 17 NaO 4 S, [M-Na] - The theoretically calculated value of 209.08475, high resolution mass spectro...

Embodiment 2

[0065] On the basis of Example 1, the 4-butoxyl-1-butylsulfonyl fluoride prepared in Example 1 is used to further prepare perfluoroether sulfonyl fluoride compounds. The specific steps are as follows:

[0066] S5: 5g of 4-perfluorobutoxy-1-perfluorobutylsulfonyl fluoride, 2g of potassium hydroxide and 2g of calcium oxide were added to 50mL of ethanol, and the temperature was raised to 50°C for 4 hours. After filtration, the obtained residue was precipitated under reduced pressure to obtain 4.8 g of the target compound as a white solid with a conversion rate of 90%.

[0067] The target compound is detected by nuclear magnetic resonance, and the detected spectrum is as attached Figure 7-8 As shown, the corresponding test result data is as follows: 13 C NMR (400MHz, CD 3 OD) δ119.1~118.5, 116.9~116.2, 115.8~114.0, 113.7~113.0, 111.8~111.1, 110.7~109.1, 108.8~107.4, 106.8~105.0.C 8 f 17 KO 4 S, [M-K] - The theoretical calculation value is 514.92458, and the high resolution ...

Embodiment 3

[0069] S1: Weigh 80g of n-butanol into a round bottom flask, add 250g (mass fraction: 22%) sodium hydroxide aqueous solution, heat up to 50°C, then add 150g of 1,4-butane sultone, and then heat up to 120°C ℃, stirring the reaction for 6h. After the reaction, the volatile components were removed by distillation under reduced pressure, and the residue was dried to obtain the target product as a light yellow solid.

[0070] The target compound was detected by nuclear magnetic resonance, and the corresponding detection result data are as follows: 1 H NMR (400MHz, CD 3 OD) δ3.48(t, J=12Hz, 2H), 3.45(t, J=12, 4.7Hz, 2H), 2.86(d, J=8.0Hz, 2H), 1.88(m, J=12Hz, 2H ), 1.73(m, J=6.6Hz, 2H), 1.69(m, J=8.4Hz, 2H), 1.42(m, J=4.8Hz, 2H), 0.96(t, J=4.8Hz, 3H). 13 C NMR (400MHz, CD 3 OD)δ71.3, 62.3, 52.3, 32.7, 29.7, 22.8, 20.2, 14.1.

[0071] S2: Weigh 100g of sodium 4-butoxy-1-butylsulfonate into a round-bottomed flask, add 1L of chlorobenzene, raise the temperature to 40°C, add 322g of...

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Abstract

The invention provides perfluoroether type sulfuryl fluoride and sulfonate compounds and synthesis methods thereof. The synthesis method of the perfluoroether type sulfuryl fluoride compound comprisesthe following steps: starting from alkyl alcohol and alkyl sultone, and reacting under the action of inorganic alkali to obtain corresponding alkyl ether type sodium sulfonate; taking the alkyl ethertype sodium sulfonate and a chlorination reagent to react, so as to obtain an alkyl ether type sulfuryl chloride compound; preparing the alkyl ether type sulfuryl chloride compound into an alkyl ether type sulfuryl fluoride compound under the action of a nucleophilic fluorinating reagent; taking hydrogen fluoride as a fluoro reagent under certain temperature, current and voltage to prepare the alkyl ether type sulfuryl fluoride compound into the perfluoroether type sulfuryl fluoride compound. A perfluoroether type potassium sulfonate compound can be prepared under certain temperature under the action of perfluoroether type sulfuryl fluoride and electrophilic potassium salt. The perfluoroether type compounds prepared by the synthesis methods provided by the invention have relatively low toxicity and certain degradation capability; degraded substances have relatively low bioaccumulation, so that the compound has relatively low risk on environmental hazards.

Description

technical field [0001] The invention belongs to the technical field of synthesis methods, and in particular relates to a perfluoroether sulfonyl fluoride and sulfonate compound and a synthesis method thereof. Background technique [0002] Perfluorinated (or Polyfluoroalkyl substances, PFASs) is a class of artificially synthesized organic compounds, which are widely used in various fields of industrial production and daily life due to their unique physical and chemical properties, including surface Activating agents, foam fire extinguishing agents, coatings and pesticides, etc. Since the fourth meeting of the Stockholm Convention in 2009, perfluorooctanesulfonic acid (PFOS) and its salts, and perfluorooctanesulfonyl fluoride (PFOSF) have been included in the list of persistent organic pollutants (POPs), The application of PFASs is limited, and its precursor compounds and substitute products have broad application prospects and are widely concerned. Studies have shown that s...

Claims

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Application Information

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IPC IPC(8): C07C309/82C07C303/02C07C303/22C07C309/10C07C303/32
CPCC07C303/02C07C303/22C07C303/32C07C309/10C07C309/82
Inventor 梁勇王亚郭锐周珍李书涛
Owner JIANGHAN UNIVERSITY
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