CN114478207B - Hexafluorobutenyl dimethyl ether and preparation method and application thereof - Google Patents
Hexafluorobutenyl dimethyl ether and preparation method and application thereof Download PDFInfo
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- CN114478207B CN114478207B CN202210265685.7A CN202210265685A CN114478207B CN 114478207 B CN114478207 B CN 114478207B CN 202210265685 A CN202210265685 A CN 202210265685A CN 114478207 B CN114478207 B CN 114478207B
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- Prior art keywords
- hexafluorobutenyl
- dimethyl ether
- dichlorohexafluorobutene
- methanol
- preparation
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- -1 Hexafluorobutenyl dimethyl ether Chemical compound 0.000 title claims abstract description 23
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 45
- OZAWCRZCYBVMBW-UHFFFAOYSA-N 4,4-dichloro-1,1,2,3,3,4-hexafluorobut-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(Cl)Cl OZAWCRZCYBVMBW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002808 molecular sieve Substances 0.000 claims description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 6
- 239000007788 liquid Substances 0.000 abstract description 14
- 238000004334 fluoridation Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002440 industrial waste Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 239000000110 cooling liquid Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/10—Vacuum distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/08—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles
- B01J8/10—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles moved by stirrers or by rotary drums or rotary receptacles or endless belts
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses hexafluorobutenyl dimethyl ether and a preparation method and application thereof. The preparation method of hexafluorobutenyl dimethyl ether comprises the following steps: at the reaction temperature of-100 to 50 ℃, firstly, mixing and stirring evenly dichlorohexafluorobutene and methanol, then adding a catalyst, continuously stirring for reaction, and then distilling under reduced pressure to obtain hexafluorobutenyl dimethyl ether. The invention has cheap raw materials and convenient sources; the product is simple to separate and purify; is easy for industrialized production; the three industrial wastes are less, and the electronic fluoridation liquid has better application prospect.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to hexafluorobutenyl dimethyl ether and a preparation method and application thereof.
Background
Under the background of the development of the cloud computing industry, more and more data centers are built, and a server is used as the most core equipment of the data center, so that the high performance, the high availability and the high cost performance of the server become important indexes for measuring the quality of the server. Because of the limited volume of the server, whether a plurality of high-power electronic components run for a long time and under high load can timely transfer the heat generated by the electronic components to the outside is directly related to the running stability of the server. Therefore, the problem of cooling the server becomes a big obstacle to the development of the server. The cooling technology of the server at present mainly comprises the following steps: air cooling technology, liquid cooling technology, heat transfer and intelligent control.
The key to the liquid cooling technology is the cooling liquid, which must be able to absorb heat quickly, conduct heat efficiently both during vaporization and liquefaction, and have the excellent properties of insulation and non-corrosiveness. The main cooling liquid at present is as follows: the first is deionized purified water, which is a good heat dissipation medium, low in price and environment-friendly, however, deionized water is easy to pollute and difficult to keep in an insulating state, and the deionized water can only be applied to non-direct contact type liquid cooling technology, and once leakage occurs, fatal damage can be caused to IT equipment; the second is mineral oil, which is commonly found in many mechanical devices, is inexpensive and insulating, but is highly viscous and easily decomposed, with a risk of combustion under specific conditions; the third is the fluorinated liquid, which is the most widely used immersion type cooling liquid at present. Compared with the former two types of cooling liquids, the fluoridation liquid is the most suitable material for the cooling liquid because of the superior insulating and nonflammable inert characteristics, non-corrosiveness, low viscosity and other physical characteristics, but the fluoridation liquid is the most expensive in three types of cooling liquids.
Disclosure of Invention
Aiming at overcoming the defects of the prior art, the invention aims to provide hexafluorobutenyl dimethyl ether and a preparation method and application thereof. The hexafluorobutenyl dimethyl ether has the advantages of low cost and easy acquisition of raw materials, and can be used as an electronic fluoridation liquid.
The aim of the invention is achieved by the following technical scheme:
A hexafluorobutenyl dimethyl ether having the structure:
the preparation method of the hexafluorobutenyl dimethyl ether comprises the following steps: at the reaction temperature of-100 to 50 ℃, firstly, mixing and stirring evenly dichlorohexafluorobutene and methanol, then adding a catalyst, continuously stirring for reaction, and then distilling under reduced pressure to obtain hexafluorobutenyl dimethyl ether.
Preferably, the molar ratio of the dichlorohexafluorobutene to the methanol is 1:2.5 to 10.
Preferably, the dichlorohexafluorobutene and methanol are mixed and stirred at a rate of 300-400 r/min for 2 hours.
Preferably, the catalyst is at least one of NaOH, KOH and Ba (OH) 2.
Preferably, the reaction temperature is-20 to 30 ℃.
Preferably, the stirring reaction time is 5-40 h.
Preferably, the dichlorohexafluorobutene and methanol are dried using molecular sieves until the water content is below 10ppm before use.
Preferably, the addition molar amount of the catalyst is 5-50% of the molar amount of the dichlorohexafluorobutene.
Application of hexafluorobutenyl dimethyl ether in preparing electronic fluorinated liquid is provided.
The chemical reaction formula of the invention is as follows:
Compared with the prior art, the invention has the beneficial effects that: the invention has cheap raw materials and convenient sources; the product is simple to separate and purify; is easy for industrialized production; the three industrial wastes are less.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The dichlorohexafluorobutene described in the examples was purchased from SynQuest Laboratories Inc.
Example 1
The dichlorohexafluorobutene and methanol were dried using molecular sieves until the water content was below 10ppm. A150 ml three-necked flask was charged with 23.3g of dichlorohexafluorobutene and 9.6g of methanol. The reaction temperature was controlled at-20℃by using an ethanol liquid nitrogen mixture, the rotation speed of a magnetic stirrer was 300r/min, and after stirring for 2 hours, 5.6g of potassium hydroxide was introduced thereinto, and after stirring for 5 hours, the mixture was distilled under reduced pressure, and a total of 28.0g of organic matters were collected. GC analysis showed 65% of which were hexafluorobutenyl dimethyl ether.
Example 2
The dichlorohexafluorobutene and methanol were dried using molecular sieves until the water content was below 10ppm. A150 ml three-necked flask was charged with 23.3g of dichlorohexafluorobutene and 16.0g of methanol. The reaction temperature was controlled to 30℃by using an ethanol liquid nitrogen mixture, the rotation speed of a magnetic stirrer was 400r/min, and after stirring for 2 hours, 5.6g of potassium hydroxide was introduced thereinto, and after stirring for 10 hours, the mixture was distilled under reduced pressure, and 34.2g of organic matters were collected in total. GC analysis shows that 56% of them are hexafluorobutenyl dimethyl ether.
Example 3
The dichlorohexafluorobutene and methanol were dried using molecular sieves until the water content was below 10ppm. A150 ml three-necked flask was charged with 23.3g of dichlorohexafluorobutene and 9.6g of methanol. The reaction temperature was controlled to 20℃by using an ethanol liquid nitrogen mixture, the rotation speed of a magnetic stirrer was 300r/min, and after stirring for 2 hours, 5.6g of potassium hydroxide and 4.0g of sodium hydroxide were introduced thereinto, and after stirring for 12 hours, the mixture was distilled under reduced pressure, and 28.0g of organic matters were collected in total. GC analysis shows that 71% of them are hexafluorobutenyl dimethyl ether.
The above-described embodiments of the present invention do not limit the scope of the present invention. Any other corresponding changes and modifications made in accordance with the technical idea of the present invention shall be included in the scope of the claims of the present invention.
Claims (6)
1. A method for preparing hexafluorobutenyl dimethyl ether, wherein the hexafluorobutenyl dimethyl ether has the following structure: the method is characterized by comprising the following steps of: at the reaction temperature of-100-50 ℃, firstly mixing and stirring uniformly dichlorohexafluorobutene and methanol, then adding a catalyst, continuously stirring for reaction, and then distilling under reduced pressure to obtain hexafluorobutenyl dimethyl ether;
The catalyst is at least one of NaOH, KOH and Ba (OH) 2;
The mol ratio of the dichlorohexafluorobutene to the methanol is 1: 2.5-10.
2. The method for preparing hexafluorobutenyl dimethyl ether according to claim 1, wherein the dichlorohexafluorobutene and methanol are mixed and stirred for 2 hours at a speed of 300-400 r/min.
3. The method for preparing hexafluorobutenyl dimethyl ether according to claim 1, wherein the reaction temperature is-20-30 ℃.
4. The method for preparing hexafluorobutenyl dimethyl ether according to claim 1, wherein the stirring reaction time is 5-40 h.
5. The method for preparing hexafluorobutenyl dimethyl ether according to claim 1, wherein the dichlorohexafluorobutene and methanol are dried by molecular sieve until the water content is lower than 10 ppm.
6. The preparation method of hexafluorobutenyl dimethyl ether according to claim 1, wherein the added molar amount of the catalyst is 5-50% of the molar amount of dichlorohexafluorobutene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210265685.7A CN114478207B (en) | 2022-03-17 | 2022-03-17 | Hexafluorobutenyl dimethyl ether and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210265685.7A CN114478207B (en) | 2022-03-17 | 2022-03-17 | Hexafluorobutenyl dimethyl ether and preparation method and application thereof |
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| Publication Number | Publication Date |
|---|---|
| CN114478207A CN114478207A (en) | 2022-05-13 |
| CN114478207B true CN114478207B (en) | 2024-05-24 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104829415A (en) * | 2015-04-03 | 2015-08-12 | 北京宇极科技发展有限公司 | Method for synthesizing hexafluoro-1,3-butadiene |
| CN111792985A (en) * | 2019-07-17 | 2020-10-20 | 北京宇极科技发展有限公司 | Fluorine-containing heat transfer fluid and preparation method and application thereof |
| CN111995502A (en) * | 2020-07-14 | 2020-11-27 | 中国矿业大学(北京) | Method for synthesizing perfluorobutyl methyl ether |
-
2022
- 2022-03-17 CN CN202210265685.7A patent/CN114478207B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104829415A (en) * | 2015-04-03 | 2015-08-12 | 北京宇极科技发展有限公司 | Method for synthesizing hexafluoro-1,3-butadiene |
| CN111792985A (en) * | 2019-07-17 | 2020-10-20 | 北京宇极科技发展有限公司 | Fluorine-containing heat transfer fluid and preparation method and application thereof |
| CN111995502A (en) * | 2020-07-14 | 2020-11-27 | 中国矿业大学(北京) | Method for synthesizing perfluorobutyl methyl ether |
Non-Patent Citations (1)
| Title |
|---|
| Electrophilic elimination of alkyl fluorides from alkyl fluoroalkenyl ethers. New synthesis of perfluoromethacrylic acid derivatives;Knunyants等;Tetrahedron;第29卷(第4期);595-601 * |
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| CN114478207A (en) | 2022-05-13 |
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