CN114634397B - Method for preparing hexafluoropropylene dimer by gas phase method - Google Patents
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- CN114634397B CN114634397B CN202210323547.XA CN202210323547A CN114634397B CN 114634397 B CN114634397 B CN 114634397B CN 202210323547 A CN202210323547 A CN 202210323547A CN 114634397 B CN114634397 B CN 114634397B
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- 238000000034 method Methods 0.000 title claims abstract description 29
- PBVZTJDHQVIHFR-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)F.FC(F)=C(F)C(F)(F)F PBVZTJDHQVIHFR-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 67
- 239000007789 gas Substances 0.000 claims abstract description 34
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims abstract description 27
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 10
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 10
- 239000000539 dimer Substances 0.000 description 9
- 239000012495 reaction gas Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- ZVVSSOQAYNYNPP-UHFFFAOYSA-N olaflur Chemical compound F.F.CCCCCCCCCCCCCCCCCCN(CCO)CCCN(CCO)CCO ZVVSSOQAYNYNPP-UHFFFAOYSA-N 0.000 description 1
- 229960001245 olaflur Drugs 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
- C07C17/281—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons of only one compound
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing hexafluoropropylene dimer by a gas phase method, which comprises the steps of introducing hexafluoropropylene gas and hydrogen fluoride gas into a coil reaction vessel in closed circulation for continuous oligomerization, cooling and rectifying product gas generated by the reaction to prepare hexafluoropropylene dimer product, wherein the oligomerization temperature is 25-60 ℃. The invention avoids the use of catalysts or solvents for polymerization in the traditional process; the preparation process is simple, the requirement on equipment is low, and the reaction condition is mild; the method has low production cost, is suitable for large-scale production, and can continuously participate in the reaction after the unreacted reactants are recycled, thereby being a green and environment-friendly synthesis method with zero emission.
Description
Technical Field
The invention relates to a preparation method of hexafluoropropylene dimer, in particular to a method for preparing hexafluoropropylene dimer by a gas phase method, and belongs to the technical field of fluorine chemical industry.
Background
Hexafluoropropylene dimer is prepared by oligomerization of hexafluoropropylene. Hexafluoropropylene dimer is a compound having a perfluorosix carbon and one double bond structure. The compound has three isomers, a pair of cis-trans isomers D1, stable property and low toxicity, and can be directly used as a solvent, a cleaning agent and a foaming agent; a dimer D2 with a branched chain structure has certain toxicity, but has larger double bond activity, and can perform various chemical reactions to prepare various fluorine-containing derivatives. The fluorine-containing derivatives can be used as medicine, pesticide intermediates, fluorine surfactants, water-resistant and oil-resistant assistants, solvents, inert liquids and the like. The hexafluoropropylene oligomerization reaction is utilized to prepare the dimer, which is easy for industrial production. The product has stable property, and is convenient for transportation and long-term storage. So that it can play a great role in the industrial fields of petroleum, textile, plastics, paint, detergent, leather, pigment, etc.
The production process of hexafluoropropylene dimer can be broadly classified into a liquid phase process and a vapor phase process. The liquid phase method is to dissolve the catalyst and its additive in aprotic polar solvent, then to introduce hexafluoropropylene for reaction, and the reaction process can be batch reaction or continuous reaction. The reaction product is insoluble in the solvent, and separation is easy after the reaction is finished, but a small amount of solvent and catalyst are carried in the product phase, washing is needed before rectification to remove the solvent and the catalyst, post-treatment is troublesome, and the solvent and the catalyst removed by washing are difficult to recover. The catalyst is mainly fluoride, but the selection range is wider, and metal fluoride, metal fluorohydride, organic amine fluoride, quaternary ammonium salt, quaternary phosphonium salt, aromatic chromium complex, cyanide, cyanate, thiocyanate and the like can be used, or crown ether with very high price is adopted as a cocatalyst.
The gas phase process is a solvent-free oligomerization process. The catalyst is usually packed in a tubular reactor and hexafluoropropylene gas is continuously reacted through the catalyst layer. The reaction temperature is required to be above 250 ℃ because the materials in the system are ensured to be in a gaseous state. The post-treatment of the reaction is to directly rectify the condensed reaction gas. The catalyst used in the gas phase method is fluoride of alkali metal, which is mainly prepared by using CsF or KF adsorbed on active carbon or nickel oxide as catalyst or directly using active carbon as catalyst, and passing hexafluoropropylene gas through a tubular reactor filled with active carbon granules at 410-420 ℃.
Both gas phase and liquid phase processes are of great interest.
In the whole, the liquid phase method has higher primary conversion rate and yield, better selectivity is realized by adjusting the technological parameters, the requirement on reaction control is lower than that of the gas phase method, but the requirements on the reaction conditions such as raw materials, catalysts, solvents and the like are high, the reaction is carried out under the airtight anhydrous condition, and the post-treatment is complicated. The gas phase method has high automation degree, convenient post-treatment, suitability for large-scale production, low single pass conversion rate and large equipment investment.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for preparing hexafluoropropylene dimer by a gas phase method so as to improve the single pass conversion rate and reduce the equipment investment.
In order to solve the technical problems, the invention discloses a method for preparing hexafluoropropylene dimer by a gas phase method, which comprises the steps of introducing hexafluoropropylene gas and hydrogen fluoride gas into a coil reaction vessel in closed circulation for continuous oligomerization, cooling and rectifying product gas generated by the reaction to prepare hexafluoropropylene dimer products.
Further, the oligomerization temperature is 25-60 ℃.
Further, the hexafluoropropylene is introduced into the coil reaction vessel at a flow rate of 1.5-15 kg/h, and the amount of the hydrogen fluoride is 5-15% of the hexafluoropropylene, namely the flow rate of the hydrogen fluoride introduced into the reaction vessel is 5-15% of the hexafluoropropylene introduction flow rate.
Further, the coil radius of the coil reaction vessel is 0.5-5 cm, and the coil length is 20-108 m.
Compared with the prior art, the method has the following beneficial effects:
1) The invention avoids the use of catalysts or solvents for polymerization in the traditional process;
2) The preparation process is simple, has low requirements on equipment, and has mild reaction conditions;
3) The invention has low production cost, is suitable for large-scale production, and the unreacted substances can be recycled to participate in the reaction, thus being a green and environment-friendly synthesis method with zero emission.
The conversion rate of the invention is more than or equal to 94%, and the hexafluoropropylene dimer content of the product analyzed by gas chromatography is more than or equal to 99%.
Detailed Description
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
Hexafluoropropylene gas is introduced into coil reaction vessels with the radius of 0.5 cm and the length of 20 m respectively at the speed of 1.5kg/h and 75g/h, the reaction is carried out at the reaction temperature of 25 ℃, after the reaction is finished, the reaction gas is cooled and enters a separation tower for rectification, 0.71kg/h of hexafluoropropylene dimer product is separated, the conversion rate is 94%, and the dimer content of the hexafluoropropylene is 99.5% after gas chromatography analysis.
Example 2
Hexafluoropropylene gas is introduced into coil reaction vessels with the radius of 5 cm and the length of 108 m respectively at 15kg/h and 2.25kg/h of hydrogen fluoride gas, the reaction is carried out at the reaction temperature of 60 ℃, after the reaction is finished, the reaction gas is cooled and enters a separation tower for rectification, 7.28kg/h of hexafluoropropylene dimer product is separated, the conversion rate is 97%, and the dimer content of the hexafluoropropylene is 99.6% after gas chromatography analysis.
Example 3
Hexafluoropropylene gas is introduced into coil reaction vessels with the radius of 3 cm and the length of 68 m at the speed of 10kg/h and 1kg/h of hydrogen fluoride gas respectively, the reaction is carried out at the reaction temperature of 30 ℃, after the reaction is finished, the reaction gas is cooled and enters a separation tower for rectification, 4.75kg/h of hexafluoropropylene dimer products are separated, the conversion rate is 95%, and the dimer content of the hexafluoropropylene reaches 99.1% after gas chromatography analysis.
Example 4
Hexafluoropropylene gas is introduced into coil reaction vessels with the radius of 3 cm and the length of 80 m respectively at the speed of 2kg/h and 0.2kg/h, the reaction is carried out at the reaction temperature of 30 ℃, after the reaction is finished, the reaction gas is cooled and enters a separation tower for rectification, 3.17kg/h of hexafluoropropylene dimer products are separated, the conversion rate is 95%, and the dimer content of the hexafluoropropylene is 99.1% after gas chromatography analysis.
Example 5
And (3) introducing 15kg/h of hexafluoropropylene gas and 1.8kg/h of hydrogen fluoride gas into coil reaction vessels with the radius of 1 cm and the length of 64 m respectively, reacting at the reaction temperature of 40 ℃, cooling the reaction gas after the reaction is finished, and rectifying in a separation tower to separate 7.2kg/h of hexafluoropropylene dimer product, wherein the conversion rate is 96%, and the dimer content of the hexafluoropropylene reaches 99% in gas chromatography analysis.
Example 6
And (3) introducing hexafluoropropylene gas into coil reaction vessels with the radius of 1 cm and the length of 36 m at the speed of 1.5kg/h and 150g/h of hydrogen fluoride gas respectively, reacting at the reaction temperature of 50 ℃, cooling the reaction gas after the reaction is finished, and rectifying in a separation tower to separate hexafluoropropylene dimer products with the conversion rate of 95 percent and the dimer content of the hexafluoropropylene reaching 99.7 percent.
EXAMPLE 7 preparation of hexafluoropropylene dimer
Hexafluoropropylene gas is introduced into coil reaction vessels with the radius of 1 cm and the length of 36 m respectively at the speed of 5kg/h and the speed of 0.6kg/h, the reaction is carried out at the reaction temperature of 30 ℃, after the reaction is finished, the reaction gas is cooled and enters a separation tower for rectification, the hexafluoropropylene dimer product is separated at the speed of 2.4kg/h, the conversion rate is 96%, and the dimer content of the hexafluoropropylene is 99.7% after gas chromatography analysis.
In each example, the product from the coil reaction vessel is cooled (preferably to 25 ℃) and condensed, and enters the separation tower, and unreacted reaction gas is returned to participate in the reaction, so that the reaction is sufficient.
Claims (2)
1. A method for preparing hexafluoropropylene dimer by a gas phase method, which is characterized in that: introducing hexafluoropropylene gas and hydrogen fluoride gas into a coil reaction vessel with closed circulation for continuous oligomerization, cooling and rectifying the product gas generated by the reaction to obtain hexafluoropropylene dimer product; the oligomerization reaction temperature is 25-60 ℃; the hexafluoropropylene is introduced into the coil reaction vessel at a flow rate of 1.5-15 kg/h, and the flow rate of hydrogen fluoride introduced into the reaction vessel is 5-15% of the flow rate of hexafluoropropylene.
2. The method for producing hexafluoropropylene dimer by the gas phase process according to claim 1, wherein: the radius of the coil pipe reaction vessel is 0.5-5 cm, and the length of the coil pipe is 20-108 m.
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| CN202210323547.XA CN114634397B (en) | 2022-03-30 | 2022-03-30 | Method for preparing hexafluoropropylene dimer by gas phase method |
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| CN114634397B true CN114634397B (en) | 2024-04-19 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917724A (en) * | 1973-02-09 | 1975-11-04 | Hoechst Ag | Process for preparing oligomers of hexafluoropropene |
| JPS5738727A (en) * | 1980-08-18 | 1982-03-03 | Nippon Petrochem Co Ltd | Dimerization of n-olefin |
| US4451689A (en) * | 1982-07-27 | 1984-05-29 | Chevron Research Company | Co-dimerization of olefins |
| CN109651075A (en) * | 2018-11-30 | 2019-04-19 | 天津市长芦化工新材料有限公司 | The controllable polymerization method and device of hexafluoropropylene dimmer |
| CN110841667A (en) * | 2019-10-30 | 2020-02-28 | 浙江利化新材料科技有限公司 | Catalyst and application thereof in preparation of heptafluoropropane |
| CN112500259A (en) * | 2020-12-14 | 2021-03-16 | 常熟三爱富中昊化工新材料有限公司 | Preparation method of heptafluoropropane |
-
2022
- 2022-03-30 CN CN202210323547.XA patent/CN114634397B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917724A (en) * | 1973-02-09 | 1975-11-04 | Hoechst Ag | Process for preparing oligomers of hexafluoropropene |
| JPS5738727A (en) * | 1980-08-18 | 1982-03-03 | Nippon Petrochem Co Ltd | Dimerization of n-olefin |
| US4451689A (en) * | 1982-07-27 | 1984-05-29 | Chevron Research Company | Co-dimerization of olefins |
| CN109651075A (en) * | 2018-11-30 | 2019-04-19 | 天津市长芦化工新材料有限公司 | The controllable polymerization method and device of hexafluoropropylene dimmer |
| CN110841667A (en) * | 2019-10-30 | 2020-02-28 | 浙江利化新材料科技有限公司 | Catalyst and application thereof in preparation of heptafluoropropane |
| CN112500259A (en) * | 2020-12-14 | 2021-03-16 | 常熟三爱富中昊化工新材料有限公司 | Preparation method of heptafluoropropane |
Non-Patent Citations (2)
| Title |
|---|
| 六氟丙烯齐聚反应的研究;武宏科, 史鸿鑫, 项斌, 项菊萍, 姜一飞, 周海安;浙江工业大学学报;33(第02期);第162-164、169页 * |
| 曾毓华.《氟碳表面活性剂》.化学工业出版社,2001,(第第1版版),第51-55页. * |
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