CN101747239B - Method for separating and refining trifluoro-methanesulfonyl fluoride CF3SO2 - Google Patents

Method for separating and refining trifluoro-methanesulfonyl fluoride CF3SO2 Download PDF

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CN101747239B
CN101747239B CN200810243626XA CN200810243626A CN101747239B CN 101747239 B CN101747239 B CN 101747239B CN 200810243626X A CN200810243626X A CN 200810243626XA CN 200810243626 A CN200810243626 A CN 200810243626A CN 101747239 B CN101747239 B CN 101747239B
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gas
fluoride
sulfonic acid
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CN101747239A (en
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李建中
许文林
陶荣辉
王雅琼
徐晓强
沙红霞
陈晓荣
吴彬
蒋德生
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JIANGSU GUOTAI SUPER POWER NEW MATERIALS CO., LTD.
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Yangzhou University
Zhangjiagang Guotai Huarong New Chemical Materials Co Ltd
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Abstract

The invention relates to a method for separating and refining trifluoro-methanesulfonyl fluoride CF3SO2. In the method, a methanesulfonyl fluoride CF3SO2 electrochemical fluorination reaction gas-phase product is taken as raw materials. The method comprises the following steps: firstly, cooling and condensing the methanesulfonyl fluoride CF3SO2 electrochemical fluorination reaction gas-phase product, so that hydrogen fluoride HF in gas phase is condensed into liquid phase; secondly, carrying out gas-liquid separation; thirdly, washing gas-phase materials obtained from the previous step in sodium carbonate water solution; fourthly, carrying out vapor-liquid separation; fifthly, adding dehydrating agents in gas-phase materials obtained from the previous step to dewater and dry; sixthly, carrying out gas-liquid separation; seventhly, carrying out next step to gas-phase materials obtained from the previous step after being deeply; and eighthly, carrying out gas-liquid separation to materials obtained from the previous step and ensuring that the liquid phase is the obtained trifluoro-methanesulfonyl fluoride CF3SO2 obtained by being separated and refined. The invention has the advantages of simple process, less power consumption, low cost and good product quality.

Description

Trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification
Technical field
The present invention relates to a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is particularly with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is raw material separation and purification trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F belongs to the fine chemical technology field.
Background technology
Trifluoromethyl sulfonic acid fluoride CF 3SO 2F is the important foundation raw material of the novel Chemicals of complex functionality type in the field of fine chemical, is the important source material of synthetic ionic liquid, fluorine surfactant and lithium-ion electrolyte etc., is with a wide range of applications development and preparation trifluoromethyl sulfonic acid fluoride CF 3SO 2The new process of F and gordian technique are to construct the important research and development field of functional type, meticulous type, the meticulous fluorine chemical product of high-level efficiency.
Trifluoromethyl sulfonic acid fluoride, molecular formula are CF 3SO 2F, normal temperature for brown gas, about BP:-21 ℃, is slightly soluble in water down, is dissolved in the organic solvent, and the reactivity ratio is higher.
Methanesulfonyl fluoride CH 3SO 2The F electrochemical fluorination gas-phase product is meant with CH 3SO 2F is a raw material, in HF solution, carries out the electrochemical fluorination reaction, generates principal product trifluoromethyl sulfonic acid fluoride CF at anode 3SO 2F generates by product hydrogen H at negative electrode 2, and because the boiling point lower (19.5 ℃) of HF and with CF 3SO 2F and H 2Leave the gas phase mixture of electrochemical fluorination reactor drum together with gas form, mainly contain CF 3SO 2F, H 2And HF, because water H is arranged 2O and CH 3SO 2Bond rupture and the trace impurity that produce of F in the electrochemical fluorination process is like oxygen difluoride OF 2, tetrafluoro-methane CF 4Wait the impurity of the difficult liquefaction of some lower boilings.
Summary of the invention
The purpose of this invention is to provide that a kind of process method is simple, less energy consumption, quality is good, cost is low trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification.
The technical scheme that realizes above-mentioned purpose is: a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, and said method steps is following:
(1) cooling condensation: with methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: will go up material that step cooling condensation obtains and carry out solution-air and separate, liquid-phase fluorination hydrogen HF goes further to handle the back and recycles, and gas phase gets into next step;
(3) washing: will go up the gaseous phase materials that obtains of step and carry out the carbonate aqueous solution washing, the material after the washing gets into next step;
(4) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, liquid phase is gone further processing, and gas phase gets into next step;
(5) dehydrate: will go up in the gaseous phase materials that obtains of step and add dewatering agent, and dehydrate;
(6) gas-solid separation: the material that will go up after a step dewaters carries out gas-solid separation, and solid phase is gone further processing, and gas phase gets into next step;
(7) deep cooling but: will go up material that a step obtains gas phase and carry out deep cooling and but get into next step in the back;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
Further, the service temperature of the first step cooling condensation is-20 ℃～0 ℃, and the operation absolute pressure is 0.1MPa～1.0MPa.
Further, the described washing lotion of the 3rd step washing is Na 2CO 3, NaHCO 3, K 2CO 3Or KHCO 3In the aqueous solution any one.
Further, to dehydrate described dewatering agent be Na the 5th step 2SO 4, P 2O 5, in activated carbon, zeyssatite or the molecular sieve any one.
Further, the 7th step, deep cooled service temperature was-80 ℃～-40 ℃, and working pressure is 0.1MPa～1.0MPa.
Trifluoromethyl sulfonic acid fluoride CF of the present invention 3SO 2The principle of F separation and purification is: (1) utilizes trifluoromethyl sulfonic acid fluoride CF 3SO 2The difference of the boiling point (19 ℃) of F boiling point (21 ℃) and hydrogen fluoride HF through the refrigerative method, makes hydrogen fluoride HF liquefaction, separates through solution-air then, and product is separated with hydrogen fluoride, turns back to the electrochemical fluorination systemic circulation through liquefaction hydrogen fluoride HF and uses; (2) the indissoluble liquid that utilizes the trifluoromethyl sulfonic acid fluoride is in water, and difficult hydrolysis, the difference that hydrogen fluoride HF dissolves easily in water, and the operation through washing separates with a spot of hydrogen fluoride HF product with other water miscible impurity; (3) utilize trifluoromethyl sulfonic acid fluoride CF 3SO 2F is prone to liquefaction (boiling point-21 ℃), hydrogen H 2The characteristics of difficult liquefaction through deep cooled method, make trifluoromethyl sulfonic acid fluoride CF 3SO 2F liquefaction is refining.
Realize that the main technique equipment that the present invention needs is: cooling apparatus, straining installation etc.
Adopt the benefit of technique scheme to be: (1), make full use of the singularity of product, operational path is short, and technology is simple, consuming little energy, production cost is low, has improved the security of technological process; (2), realized cleaning production, be convenient to suitability for industrialized production, the no three wastes produce, cleaning, environmental protection, various by products can be recycled, this has practiced thrift cost greatly; (3), adopt the product methyl fluoride sulfonic acid fluoride CF of process method separation and purification of the present invention 3SO 2The F quality is good, yield is high.
Description of drawings
Accompanying drawing is a process flow sheet of the present invention.
Embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is done further detailed explanation.
Main technique equipment is: cooling apparatus and straining installation etc.
Embodiment one
As shown in the figure, a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, and said method steps is following:
(1) cooling condensation: in indirect cooling heat exchanger, will mainly contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F, hydrogen fluoride HF and hydrogen H 2Methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product, the operation absolute pressure is 0.8MPa, is cooled to-9 ℃, makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: in gas-liquid separator, HF removes to turn back to CH with liquid-phase fluorination hydrogen 3SO 2Recycle in the reaction of F electrochemical fluorination, contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Gas phase get into next step;
(3) washing: will go up the gaseous phase materials that obtains of step through in the bubbling absorption unit, through the yellow soda ash Na of 0.1mol/L 2CO 3The aqueous solution, washing are removed the hydrogen fluoride HF and other impurity of gaseous phase materials trace, and the material after the washing gets into next step;
(4) solution-air is separated: in gas-liquid separator, HF removes to turn back to CH with liquid-phase fluorination hydrogen 3SO 2Recycle in the reaction of F electrochemical fluorination, contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Gas phase get into next step;
(5) dehydrate: will go up the gaseous phase materials that obtains of step is the dewatering drying device of filler through the 4A molecular sieve, sloughs the water in the gaseous phase materials;
(6) gas-solid separation: the gaseous phase materials gas phase through dehydrating gets into next step;
(7) deep cooling but: in indirect cooling heat exchanger, with trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Carry out deep cooling but, the operation absolute pressure is 1.0MPa, is cooled to-40 ℃, makes the trifluoromethyl sulfonic acid fluoride CF in the gas phase 3SO 2F is cooled to liquid phase;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
Embodiment two
As shown in the figure, a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, and said method steps is following:
(1) cooling condensation: in indirect cooling heat exchanger, will mainly contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F, hydrogen fluoride HF and hydrogen H 2Methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product, the operation absolute pressure is 0.5MPa, is cooled to-15 ℃, makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: in gas-liquid separator, HF removes to turn back to CH with liquid-phase fluorination hydrogen 3SO 2Recycle in the reaction of F electrochemical fluorination, contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Gas phase get into next step;
(3) washing: will go up the gaseous phase materials that obtains of step through in the filler absorption unit, through the sodium hydrogencarbonate NaHCO of 0.2mol/L 3The aqueous solution, washing are removed the hydrogen fluoride HF and other impurity of gaseous phase materials trace, and the material after the washing gets into next step;
(4) solution-air is separated: the gas material of removing the micro-hydrogen fluoride HF of gaseous phase materials and other impurity through washing gets into next step, and liquid phase is gone further processing, and gas phase gets into next step;
(5) dehydrate: will go up the gaseous phase materials that obtains of step is that the activated carbon of 1mm is the dewatering drying device of filler through equivalent diameter, sloughs the water in the gaseous phase materials;
(6) gas-solid separation: the gaseous phase materials gas phase through dehydrating gets into next step;
(7) deep cooling but: in indirect cooling heat exchanger, with trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Carry out deep cooling but, the operation absolute pressure is 0.5MPa, is cooled to-60 ℃, makes the trifluoromethyl sulfonic acid fluoride CF in the gas phase 3SO 2F is cooled to liquid phase;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
Embodiment three
As shown in the figure, a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, and said method steps is following:
(1) cooling condensation: in indirect cooling heat exchanger, will mainly contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F, hydrogen fluoride HF and hydrogen H 2Methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product, the operation absolute pressure is 0.1MPa, is cooled to-20 ℃, makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: in gas-liquid separator, HF removes to turn back to CH with liquid-phase fluorination hydrogen 3SO 2Recycle in the reaction of F electrochemical fluorination, contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Gas phase get into next step;
(3) washing: will go up the gaseous phase materials that obtains of step through the bubbling absorption unit, process is carried out the salt of wormwood K of 0.1mol/L 2CO 3The aqueous solution, washing are removed the hydrogen fluoride HF and other impurity of gaseous phase materials trace, and the material after the washing gets into next step;
(4) solution-air is separated: the gas material of removing the micro-hydrogen fluoride HF of gaseous phase materials and other impurity through washing gets into next step, and liquid phase is gone further processing, and gas phase gets into next step;
(5) dehydrate: will go up the gaseous phase materials that obtains of step is that the zeyssatite of 1mm is the dewatering drying device of filler through equivalent diameter, sloughs the water in the gaseous phase materials;
(6) gas-solid separation: the gaseous phase materials gas phase through dehydrating gets into next step;
(7) deep cooling but: in indirect cooling heat exchanger, with trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Carry out deep cooling but, the operation absolute pressure is 0.2MPa, is cooled to-70 ℃, makes the trifluoromethyl sulfonic acid fluoride CF in the gas phase 3SO 2F is cooled to liquid phase;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
Embodiment four
As shown in the figure, a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, and said method steps is following:
(1) cooling condensation: in indirect cooling heat exchanger, will mainly contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F, hydrogen fluoride HF and hydrogen H 2Methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product, the operation absolute pressure is 0.1MPa, is cooled to-20 ℃, makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: in gas-liquid separator, HF removes to turn back to CH with liquid-phase fluorination hydrogen 3SO 2Recycle in the reaction of F electrochemical fluorination, contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Gas phase get into next step;
(3) washing: will go up the gaseous phase materials that obtains of step through the filler absorption unit, through the saleratus KHCO of 0.2mol/L 3The aqueous solution, washing are removed the hydrogen fluoride HF and other impurity of gaseous phase materials trace, and the material after the washing gets into next step;
(4) solution-air is separated: the gas material of removing the micro-hydrogen fluoride HF of gaseous phase materials and other impurity through washing gets into next step, and liquid phase is gone further processing, and gas phase gets into next step;
(5) dehydrate: will go up the gaseous phase materials that obtains of step is the Na of 1mm through equivalent diameter 2SO 4Be the dewatering drying device of filler, slough the water in the gaseous phase materials;
(6) gas-solid separation: the gaseous phase materials gas phase through dehydrating gets into next step;
(7) deep cooling but: in indirect cooling heat exchanger, with trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Carry out deep cooling but, the operation absolute pressure is 0.1MPa, is cooled to-80 ℃, makes the trifluoromethyl sulfonic acid fluoride CF in the gas phase 3SO 2F is cooled to liquid phase;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
Embodiment five
As shown in the figure, a kind of trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, and said method steps is following:
(1) cooling condensation: in indirect cooling heat exchanger, will mainly contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F, hydrogen fluoride HF and hydrogen H 2Methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product, the operation absolute pressure is 1.0MPa, is cooled to 0 ℃, makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: in gas-liquid separator, HF removes to turn back to CH with liquid-phase fluorination hydrogen 3SO 2Recycle in the reaction of F electrochemical fluorination, contain trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Gas phase get into next step;
(3) washing: will go up the gaseous phase materials that obtains of step through the filler absorption unit, through the saleratus KHCO of 0.2mol/L 3The aqueous solution, washing are removed the hydrogen fluoride HF and other impurity of gaseous phase materials trace, and the material after the washing gets into next step;
(4) solution-air is separated: the gas material of removing the micro-hydrogen fluoride HF of gaseous phase materials and other impurity through washing gets into next step, and liquid phase is gone further processing, and gas phase gets into next step;
(5) dehydrate: will go up the gaseous phase materials that obtains of step is the P of 1mm through equivalent diameter 2O 5Be the dewatering drying device of filler, slough the water in the gaseous phase materials;
(6) gas-solid separation: the gaseous phase materials gas phase through dehydrating gets into next step;
(7) deep cooling but: in indirect cooling heat exchanger, with trifluoromethyl sulfonic acid fluoride CF 3SO 2F and hydrogen H 2Carry out deep cooling but, the operation absolute pressure is 0.8MPa, is cooled to-50 ℃, makes the trifluoromethyl sulfonic acid fluoride CF in the gas phase 3SO 2F is cooled to liquid phase;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
Remove the various embodiments described above, embodiment of the present invention also have a lot, and the technical scheme that all employings are equal to or equivalence is replaced is all within protection scope of the present invention.

Claims (3)

1. trifluoromethyl sulfonic acid fluoride CF 3SO 2The method of F separation and purification is with methanesulfonyl fluoride CH 3SO 2F electrochemical fluorination reaction gas-phase product is a raw material, it is characterized in that said method steps is following:
(1) cooling condensation: with methanesulfonyl fluoride CH 3SO 2The condensation of lowering the temperature of F electrochemical fluorination gas-phase product makes the hydrogen fluoride HF in the gas phase be condensed into liquid phase;
(2) solution-air is separated: will go up material that step cooling condensation obtains and carry out solution-air and separate, liquid-phase fluorination hydrogen HF goes further to handle the back and recycles, and gas phase gets into next step;
(3) washing: will go up the gaseous phase materials that obtains of step and carry out the carbonate aqueous solution washing, the material after the washing gets into next step;
(4) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, liquid phase is gone further processing, and gas phase gets into next step;
(5) dehydrate: will go up in the gaseous phase materials that obtains of step and add dewatering agent, and dehydrate;
(6) gas-solid separation: the material that will go up after a step dewaters carries out gas-solid separation, and solid phase is gone further processing, and gas phase gets into next step;
(7) deep cooling but: will go up material that a step obtains gas phase and carry out deep cooling and but get into next step in the back, this goes on foot deep cooled service temperature is-80 ℃～-40 ℃, and working pressure is 0.1MPa～1.0MPa;
(8) solution-air is separated: will go up material that a step obtains and carry out solution-air and separate, gas phase is hydrogen H 2Go further processing, liquid phase is the product trifluoromethyl sulfonic acid fluoride CF that separation and purification obtains 3SO 2F.
2. trifluoromethyl sulfonic acid fluoride CF according to claim 1 3SO 2The method of F separation and purification is characterized in that: the service temperature of the first step cooling condensation is-20 ℃～0 ℃, and the operation absolute pressure is 0.1MPa～1.0MPa.
3. trifluoromethyl sulfonic acid fluoride CF according to claim 1 3SO 2The method of F separation and purification is characterized in that: it is Na that the 5th step dehydrated described dewatering agent 2SO 4, P 2O 5, in gac, zeyssatite or the molecular sieve any one.
CN200810243626XA 2008-12-11 2008-12-11 Method for separating and refining trifluoro-methanesulfonyl fluoride CF3SO2 Active CN101747239B (en)

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CN112760672B (en) * 2020-12-15 2022-04-08 中船(邯郸)派瑞特种气体股份有限公司 Method for electrochemically preparing trifluoromethyl sulfonyl fluoride from methyl sulfonyl chloride
CN115340459B (en) * 2021-05-13 2023-12-26 中昊晨光化工研究院有限公司 Industrial method for removing impurities in trifluoromethyl fluoacid ester

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003206272A (en) * 2001-12-28 2003-07-22 Kanto Denka Kogyo Co Ltd Method of production for fluorine containing alkanesulfonylfluoride
WO2008111418A1 (en) * 2007-03-09 2008-09-18 Central Glass Company, Limited Method for producing trifluoromethanesulfonyl fluoride

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003206272A (en) * 2001-12-28 2003-07-22 Kanto Denka Kogyo Co Ltd Method of production for fluorine containing alkanesulfonylfluoride
WO2008111418A1 (en) * 2007-03-09 2008-09-18 Central Glass Company, Limited Method for producing trifluoromethanesulfonyl fluoride

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