CN117023520A - Method for preparing sulfuryl fluoride by taking sulfuryl chloride as raw material - Google Patents
Method for preparing sulfuryl fluoride by taking sulfuryl chloride as raw material Download PDFInfo
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- CN117023520A CN117023520A CN202311100795.9A CN202311100795A CN117023520A CN 117023520 A CN117023520 A CN 117023520A CN 202311100795 A CN202311100795 A CN 202311100795A CN 117023520 A CN117023520 A CN 117023520A
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- sulfuryl
- sulfuryl chloride
- fluoride
- raw material
- preparing
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 239000005935 Sulfuryl fluoride Substances 0.000 title claims abstract description 31
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000002994 raw material Substances 0.000 title claims abstract description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 35
- 239000007789 gas Substances 0.000 claims abstract description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000002309 gasification Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000010574 gas phase reaction Methods 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 27
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 13
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 8
- 238000007670 refining Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000003682 fluorination reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 description 1
- 241000204035 Kalotermitidae Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000012840 feeding operation Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IXYXXQNFKSEXJM-UHFFFAOYSA-N n,n-dimethylmethanamine;hydron;fluoride Chemical compound F.CN(C)C IXYXXQNFKSEXJM-UHFFFAOYSA-N 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/45—Compounds containing sulfur and halogen, with or without oxygen
- C01B17/4561—Compounds containing sulfur, halogen and oxygen only
- C01B17/4576—Sulfuryl fluoride (SO2F2)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material, wherein the sulfuryl chloride is gasified and then reacts with amine complex of hydrogen fluoride in a pipeline reactor in a gas phase to obtain the sulfuryl chloride; the pipeline reactors are connected in series, the first stage heating temperature is 100-350 ℃, and the second stage heating temperature is 150-450 ℃. The method can effectively improve the conversion rate and the yield of the product, and is easy for industrial production.
Description
Technical Field
The invention relates to a preparation method of sulfuryl fluoride, in particular to a method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material.
Background
The sulfuryl fluoride is a fumigation gas used for controlling various pests, is non-flammable, non-corrosive and free from generating taste, has strong penetrability, can quickly penetrate into various materials, effectively kills various social pests such as dry wood termites, and can quickly dissipate during gas dispersion. Compared with bromomethane, the method has the advantages of faster, more effective and more economical killing of various pests, no ozone layer damage and environment protection.
The existing preparation method of sulfuryl fluoride comprises 1) preparing trifluoroacetyl chloride from sulfur trioxide, and then preparing sulfuryl fluoride by fluorination; 2) Sulfuryl chloride is used as a raw material, and sulfuryl fluoride is prepared through catalytic fluorination; 3) Sulfur dioxide is used as raw material, and is reacted with chlorine and hydrogen fluoride in a fixed bed reactor with catalyst to prepare the catalyst. The environmental pollution of preparing trifluoroacetyl chloride by using sulfur trioxide is large, and the post-treatment of the product is complex; sulfur dioxide, chlorine and hydrogen fluoride are used for chlorofluorination reaction, and the transportation of the sulfur dioxide, the chlorine and the hydrogen fluoride is limited, so that the chlorine is used as a raw material to often influence the production progress especially in the domestic major activities or special time periods such as holidays. In addition, sulfur dioxide, chlorine and hydrogen fluoride are reactions which are carried out under the catalysis of activated carbon and potassium hydrogen fluoride, carbon dioxide is generated in the catalytic reaction process and needs to be treated, the catalyst also often fails to agglomerate, and the environment is influenced and the operation is difficult when the catalyst is replaced. Therefore, the preparation of sulfuryl fluoride by catalytic fluorination using sulfuryl chloride as a raw material is one development direction. However, sulfuryl chloride and hydrogen fluoride are directly subjected to catalytic fluorination, so that the reaction is severe, when the operation is careless, the reaction is easy to explode, the danger is high, and the method is not suitable for industrial production. And the intermittent liquid phase reaction is adopted, so that the efficiency is low, and the product separation is difficult.
Sulfuryl chloride is called sulfonyl chloride, and the molecular formula of the English name sulfuryl chloride is SO 2 Cl 2 The molecular weight 134.97 is colorless or pale yellow liquid, the boiling point is 68-70 ℃, and the liquid is mainly used as a chlorinating agent or chlorosulfonating agent for the chlorination of aromatic compounds, the chlorination of carboxylic acids and the chlorination of other various organic and inorganic compounds; it is also used for preparing pharmaceuticals, dyes, surfactants, etc.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for preparing sulfuryl fluoride by utilizing amine complex of sulfuryl chloride and hydrogen fluoride to carry out gas-phase fluorination. The method can effectively improve the yield and conversion rate of the product, and is suitable for large-scale production.
In order to solve the technical problems, the invention discloses a method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material, wherein the sulfuryl chloride is gasified and then reacts with amine complex of hydrogen fluoride in a pipeline reactor in a gas phase to obtain the sulfuryl chloride;
the pipeline reactors are connected in series, the first stage heating temperature is 100-350 ℃, and the second stage heating temperature is 150-450 ℃.
Further, the sulfuryl chloride has a gasification temperature of 80 to 150 ℃.
Further, the sulfuryl chloride gasification temperature is 80-100 ℃.
Further, the pipeline reactor is a rotary pipeline reactor.
Further, the amine complex of hydrogen fluoride contains one or more than two kinds, each composed of a plurality of hydrogen fluoride molecules and one carbon C 1～6 Is provided withComplexing organic amine molecules.
Further, the feed molar ratio of the amine complex of sulfuryl chloride and hydrogen fluoride is 1: 2 to 5, the molar quantity of the amine complex of hydrogen fluoride to be fed is calculated by hydrogen fluoride.
Further, the feed amount of the sulfuryl chloride gas was 1.35kg/s.
The invention prepares the sulfuryl fluoride by utilizing the amine complex of sulfuryl chloride and hydrogen fluoride through gas phase fluorination, solves the problems of limited transportation and sources of sulfur dioxide, chlorine and hydrogen fluoride, and environmental protection pressure of the sulfur dioxide, the chlorine and the hydrogen fluoride, and is a production technology with energy conservation, emission reduction, sustainable development, circular economy and environmental protection. Compared with the prior art, the technical scheme adopted by the invention has the advantages that the product quality is good, and the technical indexes respectively reach that the mass fraction of sulfuryl fluoride is more than or equal to 99.8%; the water content is less than or equal to 0.1 percent; the pH is more than or equal to 3.5 (meeting the standard requirements of enterprise standard Q/LMH001-2014 sulfuryl fluoride and national standard GB/T38211-2019 sulfuryl fluoride), and the yield is more than or equal to 99.9 percent. The reaction raw materials are easy to store and transport, the feeding operation is convenient, the raw material conversion rate is more than or equal to 99.9%, the invalid catalyst is not required to be treated in the production process, the industrial production is easy, and the environment is not polluted.
In addition, the invention adopts continuous gas phase reaction, products are well separated, high purity of the products is ensured, and the invention is more suitable for large-scale production. The reaction maintains higher conversion rate by controlling the heating temperature of the two sections of the reactor. The sulfuryl fluoride generated in the reaction enters a gas holder for further refining. The byproduct hydrogen chloride is absorbed by graphite pipeline water to become byproduct hydrochloric acid. The sulfuryl chloride which does not participate in the reaction and the amine hydrofluoride complex are compressed and recycled for reuse.
Description of the embodiments
The invention is further explained below with reference to examples. The following examples are only illustrative of the present invention and are not intended to limit the scope of the invention.
Example 1
After sulfuryl chloride is gasified at 80 ℃ in a gas holder, the feeding amount is introduced into a rotary pipeline reactor containing 4kg (0.2 mole based on hydrogen fluoride) of a hydrogen fluoride complex of triethylamine at a flow rate of 13.5kg/s (0.1 mole), the sulfuryl chloride is heated to 200 ℃ to react in a primary rotary pipeline reactor, the heating temperature of the serially connected secondary reactors is controlled to be 350 ℃, sulfuryl fluoride generated in the reaction enters the gas holder for refining, and the purity of the sulfuryl chloride is 99.88%, the conversion rate is 99.92% and the product yield is 99.93% through gas chromatography analysis.
Example 2
After sulfuryl chloride is gasified in a gas holder at 100 ℃, the feeding amount is introduced into a rotary pipeline reactor containing 6kg (0.3 mole based on hydrogen fluoride) of a hydrogen fluoride complex of triethylamine at a flow rate of 13.5kg/s (0.1 mole), the sulfuryl chloride is heated to be reacted in a primary rotary pipeline reactor at the temperature of 100 ℃, the heating temperature of the serially connected secondary reactors is controlled to be 250 ℃, sulfuryl fluoride generated in the reaction enters into the gas holder for refining, and the purity of the sulfuryl chloride is 99.90%, the conversion rate is 99.92% and the product yield is 99.92% by gas chromatography analysis.
Example 3
After sulfuryl chloride is gasified in a gas holder at 150 ℃, the feeding amount is introduced into a rotary pipeline reactor filled with 6kg (0.3 mol calculated by hydrogen fluoride) of hydrogen fluoride complex of tri-n-butylamine at a flow rate of 13.5kg/s (0.1 mol), the sulfuryl chloride is reacted in a primary rotary pipeline reactor at a temperature of 350 ℃, the heating temperature of the secondary reactors connected in series is controlled to be 450 ℃, sulfuryl fluoride generated in the reaction enters the gas holder for refining, and the purity of the sulfuryl chloride is 99.82%, the conversion rate is 99.91% and the product yield is 99.91% through gas chromatography analysis.
Example 4
After sulfuryl chloride is gasified in a gas holder at 150 ℃, the feeding amount is fed into a rotary pipeline reactor containing 10kg (0.5 mol calculated by hydrogen fluoride) of hydrogen fluoride complex of cyclohexylamine at a flow rate of 13.5kg/s (0.1 mol), the sulfuryl chloride is heated to 300 ℃ to react in a primary rotary pipeline reactor, the heating temperature of the two reactors connected in series is controlled to be 450 ℃, sulfuryl fluoride generated in the reaction enters the gas holder for refining, and the purity of the sulfuryl chloride is 99.85%, the conversion rate is 99.90% and the product yield is 99.91% through gas chromatography analysis.
Example 5
After sulfuryl chloride is gasified in a gas holder at 100 ℃, the feeding amount is fed into a rotating pipeline reactor filled with 6kg (0.3 mole) of trimethylamine hydrogen fluoride complex (calculated by hydrogen fluoride) at the flow rate of 13.5kg/s (0.1 mole), the sulfuryl chloride is heated to be reacted in a primary rotating pipeline reactor at the temperature of 100 ℃, the heating temperature of the serially connected secondary reactors is controlled to be 250 ℃, sulfuryl fluoride generated in the reaction enters the gas holder for refining, and the purity of the sulfuryl chloride is 99.92%, the conversion rate is 99.93% and the product yield is 99.92% through gas chromatography analysis.
Example 6
After sulfuryl chloride is gasified in a gas holder at 100 ℃, the feeding amount is introduced into a rotary pipeline reactor filled with 6kg (0.3 mole) of hydrogen fluoride complex of triethylamine and cyclohexylamine (calculated by hydrogen fluoride) at the flow rate of 13.5kg/s (0.1 mole), the mixture is heated to 100 ℃ to react in a primary rotary pipeline reactor, the heating temperature of the serially connected secondary reactors is controlled to be 250 ℃, sulfuryl fluoride obtained in the reaction enters the gas holder for refining, and the purity of the sulfuryl chloride is 99.93%, the conversion rate is 99.92% and the product yield is 99.91% by gas chromatography analysis.
Example 7
After sulfuryl chloride is gasified in a gas holder at 150 ℃, the feeding amount is introduced into a rotary pipeline reactor filled with 10kg (0.5 mol) of hydrogen fluoride complex of triethylamine and cyclohexanediamine (calculated as hydrogen fluoride) at a flow rate of 13.5kg/s (0.1 mol), the mixture is heated to 300 ℃ to react in a primary rotary pipeline reactor, the heating temperature of the serially connected secondary reactors is controlled to be 350 ℃, sulfuryl fluoride generated in the reaction enters the gas holder for refining, and the purity of the sulfuryl chloride is 99.86%, the conversion rate is 99.91% and the product yield is 99.92% by gas chromatography analysis.
Claims (7)
1. A method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material is characterized by comprising the following steps: gasifying sulfuryl chloride, and then carrying out gas-phase reaction on the gasified sulfuryl chloride and an amine complex of hydrogen fluoride in a pipeline reactor to obtain sulfuryl chloride;
the pipeline reactors are connected in series, the first stage heating temperature is 100-350 ℃, and the second stage heating temperature is 150-450 ℃.
2. The method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material according to claim 1, wherein the method comprises the following steps: the sulfuryl chloride has a gasification temperature of 80-150 ℃.
3. The method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material according to claim 2, wherein the method comprises the following steps: the sulfuryl chloride has a gasification temperature of 80-100 ℃.
4. The method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material according to claim 1, wherein the method comprises the following steps: the pipeline reactor is a rotary pipeline reactor.
5. The method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material according to claim 1, wherein the method comprises the following steps: the amine complex of hydrogen fluoride contains one or more than two kinds, each of which consists of a plurality of hydrogen fluoride molecules and a carbon C 1～6 Is formed by complexing organic amine molecules.
6. The method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material according to claim 1, wherein the method comprises the following steps: the feeding mole ratio of the sulfuryl chloride to the amine complex of the hydrogen fluoride is 1: 2 to 5, the molar quantity of the amine complex of hydrogen fluoride to be fed is calculated by hydrogen fluoride.
7. The method for preparing sulfuryl fluoride by taking sulfuryl chloride as a raw material according to claim 1, wherein the method comprises the following steps: the feed amount of the sulfuryl chloride gas was 1.35kg/s.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311100795.9A CN117023520A (en) | 2023-08-30 | 2023-08-30 | Method for preparing sulfuryl fluoride by taking sulfuryl chloride as raw material |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311100795.9A CN117023520A (en) | 2023-08-30 | 2023-08-30 | Method for preparing sulfuryl fluoride by taking sulfuryl chloride as raw material |
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| CN117023520A true CN117023520A (en) | 2023-11-10 |
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| CN202311100795.9A Pending CN117023520A (en) | 2023-08-30 | 2023-08-30 | Method for preparing sulfuryl fluoride by taking sulfuryl chloride as raw material |
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- 2023-08-30 CN CN202311100795.9A patent/CN117023520A/en active Pending
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