CN116478020A - High-purity hydrofluoroether compound and preparation method thereof - Google Patents
High-purity hydrofluoroether compound and preparation method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 73
- 238000002360 preparation method Methods 0.000 title abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 20
- 239000006227 byproduct Substances 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 19
- 238000004821 distillation Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 38
- 239000003999 initiator Substances 0.000 claims description 37
- 238000001556 precipitation Methods 0.000 claims description 31
- 239000000047 product Substances 0.000 claims description 24
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 15
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- 229920000858 Cyclodextrin Polymers 0.000 claims description 12
- 239000001116 FEMA 4028 Substances 0.000 claims description 12
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 12
- 229960004853 betadex Drugs 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 229910001220 stainless steel Inorganic materials 0.000 claims description 9
- 239000010935 stainless steel Substances 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 claims description 6
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000001577 simple distillation Methods 0.000 claims description 6
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 5
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229960004063 propylene glycol Drugs 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 3
- 238000011085 pressure filtration Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 abstract description 16
- 238000004140 cleaning Methods 0.000 abstract description 13
- 230000007613 environmental effect Effects 0.000 abstract description 9
- 238000007259 addition reaction Methods 0.000 abstract description 5
- 231100000956 nontoxicity Toxicity 0.000 abstract description 5
- 150000002500 ions Chemical class 0.000 abstract description 4
- 239000003989 dielectric material Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- -1 heteroatom compound Chemical class 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000031068 symbiosis, encompassing mutualism through parasitism Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a high-purity hydrofluoroether compound and a preparation method thereof. The addition reaction of the alcohol and the fluoroolefin is simple to operate, and the reaction condition is mild; the ions, high boiling point solvent and the like in the hydrofluoroether can be removed by distillation to obtain the hydrofluoroether containing by-products of unsaturated bonds, and the distillation temperature can be selected to be higher than the boiling point of the produced hydrofluoroether and lower than the temperature between the boiling points of the solvent; the method has the advantages of high efficiency, low comprehensive cost, simple treatment, no toxicity, more environmental protection, high purity of the hydrofluoroether compound, and low content of unsaturated bond compounds of less than 100ppm, and can be used in the fields of cleaning liquid, heat exchange materials, dielectric materials and the like.
Description
Technical Field
The invention belongs to the technical field of new material preparation, and particularly relates to a high-purity hydrofluoroether compound and a preparation method thereof.
Background
CFCs (chlorofluorocarbons) are the first chemically stable substances to be used in the refrigeration and cleaning industries, but cause greenhouse effect and global warming, directly result in increased ultraviolet radiation into the atmosphere, and are a considerable hazard to human society. The hydrofluoroether type substance is an ideal substance in the modern industry because it does not contain ozone-depleting elements such as chlorine and bromine, is a heteroatom compound composed of C, H, F, O and has the advantages of no toxicity, incombustibility, stability, very low ODP value and GWP value. In recent years, global symbiosis and green industry are achieved at home and abroad, so that hydrofluoroether compounds are hot-burning high-end compound materials in the fields of cleaning liquid, heat exchange materials and medium materials.
Hydrofluoroethers have a variety of synthetic routes: 1) Fluorination of ether fluorine gas or high-valence metal fluorine compound; 2) Electrochemical fluorination of ethers; 3) Substitution reaction of alcohols with halogenated hydrocarbons; 4) And methods such as addition reaction of alcohols and fluoroolefins. The first fluorination method has the highest F2 activity but the worst selectivity, and the metal fluoride has high fluorination yield but high cost, and limits the use; although the electrochemical method can synthesize the isolated hydrofluoroether, the power consumption is high, a large amount of anhydrous hydrogen fluoride is generally needed in the process, and the product contains a large amount of isomer, has similar properties, can not be separated effectively, and is not suitable for industrial application; the substitution reaction of the third alcohol and the halohydrocarbon is more severe, such as high temperature and high pressure, and has low yield and long period, which is basically eliminated.
For example, patent CN 101263103A discloses a hydrofluoroether compound and methods for preparing and using the same, which is a method of adding fluoroolefin or vinyl ether to hetero alcohol or fluoroalcohol, and can be used in the fields of fire extinguishing agents, foam plastics, vapor phase welding, heat transfer and the like, and also discloses purifying reaction products by distillation and removing olefin reaction byproducts by a reagent which preferentially reacts with olefin double bonds, such as anhydrous hydrogen fluoride, potassium difluorohydrogen solvent which is a aprotic solvent, potassium permanganate in acetone, bromine and the like, which can remove a considerable part of unsaturated impurity compounds, however, the selected reagent has a higher danger and more byproducts are easy to produce, so that purification and waste disposal are more difficult.
Patent CN 114456046A discloses a high-purity hydrofluoroether and a purification method thereof, wherein a catalyst and an auxiliary oxidant are added into a crude product containing unsaturated bond impurities to perform oxidation reaction, and then the high-purity hydrofluoroether is obtained by rectification. The method has mild reaction conditions, is convenient and environment-friendly to operate, but still needs rectification to improve the removal efficiency, adopts a mode of using various catalysts and cocatalysts to produce the catalyst in a layered mode, and the intermediate complexing layer is removed to reduce the yield greatly, so that the water washing subsequent water removal cost is high, the production period is long, and the subsequent environmental protection treatment problem of the supernatant is also increased. Similar problems exist with patent CN 114456045a as well, and relatively expensive catalysts such as hydrogen peroxide, periodate, heavy metals are used.
Patent CN 112341319A discloses a comprehensive utilization method of fluorovinyl ether by-products in the production process of hydrofluoroether, which adopts a treatment mode of adding sulfuric acid, and the sulfuric acid has strong corrosiveness to equipment, and the method is eliminated in the prior art.
The hydrofluoroether product contains unsaturated compounds such as an olefine ether compound, the boiling point of the unsaturated compounds is similar to that of the hydrofluoroether of the target product, the separation of the hydrofluoroether product is difficult by a conventional process method, the residual unsaturated compounds can cause the product to react with equipment materials in scene application, such as high-end electron heat transfer material application, the equipment is corroded, the irrecoverable loss is caused, and the storage life is also influenced; and as a reaction solvent, may cause reaction failure, etc.
Therefore, the method for preparing the high-purity hydrofluoroether in the prior art has the problems of low efficiency, environmental protection, toxicity or corrosiveness, reduced yield, limited improvement capability of purity and residual three-waste treatment, and is not suitable for the trend of green and environment-friendly development of the modern industry.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide the high-purity hydrofluoroether compound and the preparation method thereof, wherein the unsaturated compound has low content, high efficiency and purity, and less residual three wastes, meets the environmental protection requirement, and can save cost input.
The technical scheme adopted by the invention is as follows:
a high-purity hydrofluoroether compound is prepared from the crude mixture of hydrofluoroether through distilling, addition depositing, filtering and rectifying.
Further, the crude hydrofluoroether is prepared by mixing fluoroolefin or fluoroolefin ether with alcohol or phenol, adding alkaline substances and solvents, and carrying out catalytic etherification reaction.
Further, the GC% content of unsaturated byproducts in the crude hydrofluoroether product is less than or equal to 25%.
Further, the fluoroolefin is tetrafluoroethylene or hexafluoropropylene.
Still further, the fluorovinyl ether is cmf2m+1-O-cf=cf2, wherein m is an integer from 1 to 6.
Still further, the alcohol is methanol, ethanol, isopropanol, 1-butanol, 2-butanol, 1, 2-propanediol, 1, 3-propanediol, or a fluoroalcohol.
Still further, the phenol is phenol or a fluorophenol.
The invention also relates to a preparation method of the high-purity hydrofluoroether compound, which is used for preparing the high-purity hydrofluoroether compound and is characterized in that: the method comprises the following steps:
s01, distillation: the synthesized crude mixture of the hydrofluoroether is subjected to simple distillation to obtain a crude hydrofluoroether;
s02, adding and precipitating: removing water and deoxidizing the high-pressure airtight stainless steel reaction kettle to the oxygen content below 20 ppm; adding 0.05-2 parts of multifunctional branching initiator and 40-80 parts of crude hydrofluoroether into a high-pressure airtight stainless steel reaction kettle according to parts by weight; stirring and heating to 40-95 ℃, reacting for 2-8 h, and cooling and discharging to obtain a reaction material;
s03, filtering: pressurizing and filtering the reaction material by a 150-350nm filter screen, and conveying the filtered liquid to a rectifying tower;
s04, rectifying: and (3) absorbing the filtered liquid mixture through two-stage rectification to obtain rectified liquid.
Still further, the multifunctional branching initiator in the step S028 is a beta-cyclodextrin-derived peroxy-type multifunctional branching initiator, and the structural formula thereof can be expressed as follows:
wherein beta-CD represents a beta-cyclodextrin group, and n is an integer of 1 to 7.
Finally, the pressure of the pressure filtration in the step S03 is 0.1-2.0 Mpa.
The beneficial effects of the invention are as follows:
a high-purity hydrofluoroether compound is prepared through mixing fluoroolefin or fluorovinyl ether with alcohol or phenol, catalytic reaction to obtain coarse product, reaction to obtain small amount of by-product vinyl ether, and conventional distillation to obtain high-purity hydrofluoroether compound. The addition reaction of the alcohol and the fluoroolefin is simple to operate, and the reaction condition is mild; the ions, high boiling point solvent and the like in the hydrofluoroether can be removed by distillation to obtain the hydrofluoroether containing by-products of unsaturated bonds, and the distillation temperature can be selected to be higher than the boiling point of the produced hydrofluoroether and lower than the temperature between the boiling points of the solvent; the purity of the prepared hydrofluoroether compound is high, the purity of the hydrofluoroether compound is more than or equal to 99.85 percent, and especially the content of the unsaturated bond compound is lower than 100ppm; the method has the advantages of high efficiency, low comprehensive cost, simple and easily controlled process steps, no toxicity, more environmental protection and the like, does not harm equipment, human bodies and the like, and meets the requirements of a modern high-quality green industrial system; the residual three wastes are less, the environmental protection requirement is met, and the cost investment can be saved; the cleaning agent can be used for cleaning microscopic instruments and equipment, can be used as a heat conduction medium and the like, and can be popularized and applied to the fields of cleaning liquid, heat exchange materials, medium materials and the like.
Drawings
FIG. 1 is a schematic diagram showing the reaction process of reacting beta-cyclodextrin with 1,3, 5-triacylchlorobenzene and then with t-butyl hydroperoxide by a polyfunctional branched initiator in the preparation method of the high-purity hydrofluoroether compound of example one of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art without the inventive effort, are intended to be within the scope of the present invention.
The invention provides a high-purity hydrofluoroether compound and a preparation method thereof, and the whole planning scheme is as follows: firstly, a high-purity hydrofluoroether compound is conceived, and is obtained by distillation, addition precipitation, filtration and rectification of a hydrofluoroether crude product mixture.
Further, the crude hydrofluoroether is prepared by mixing fluoroolefin or fluoroolefin ether with alcohol or phenol, adding alkaline substances and solvents, and carrying out catalytic etherification reaction.
Further, the GC% content of unsaturated byproducts in the crude hydrofluoroether product is less than or equal to 25%.
Further, the fluoroolefin is tetrafluoroethylene or hexafluoropropylene.
Still further, the fluorovinyl ether is cmf2m+1-O-cf=cf2, wherein m is an integer of 1 to 6.
Still further, the alcohol is methanol, ethanol, isopropanol, 1-butanol, 2-butanol, 1, 2-propanediol, 1, 3-propanediol, or a fluoroalcohol.
Still further, the phenol is phenol or a fluorophenol.
The technical scheme of the invention is mainly to remove impurities and purify the hydrofluoroether by a chemical method. The preparation process of the hydrofluoroether product comprises the following steps: firstly, catalytic synthesis is carried out, and then post-treatment is carried out, namely, the preparation process of the high-purity hydrofluoroether in the invention. The synthesis generally comprises the steps of carrying out catalytic etherification reaction on fluoroolefin, ether, alcohol and phenol in the presence of alkaline substances and solvents, wherein side reaction or rearrangement reaction can be generated in the process, and the generated byproducts are complex, generally vinyl ether liquid impurities containing double bonds, have serious adverse effects on the stability in the application fields of cleaning, heat exchange media and the like which are especially used in the invention, are close to the boiling point of a target product (without double bonds), and are difficult to remove cleanly through rectification;
the byproducts are unsaturated byproducts containing unsaturated bonds, namely various structural byproducts of double bonds, the products are only different from target products in double bonds, the boiling points are similar, the general purification method is not easy to remove, the structural types are various and can not be determined, and the products can only be detected through GC content; the unsaturated compound content is less than or equal to 25 percent, namely the hydrofluoroether content is more than or equal to 75 percent. Both crude and purified products and the impurities therein are liquid, and as such, ordinary physical separations such as rectification cannot be removed without the boiling point being close.
The invention focuses on the use of a novel initiator with an initiating effect to polymerize and adsorb, and is incompatible with a liquid phase to precipitate out so as to achieve the aim of impurity removal. The key technical scheme of the invention is that an initiator compound with a novel structure and a synergistic function is used, and the prior literature is not recorded with the compound; and rectifying to remove trace amount of solvent and other matters remained in the synthesis step, thereby obtaining the hydrofluoroether compound with ultrahigh purity.
The invention also relates to a preparation method of the high-purity hydrofluoroether compound, which is used for preparing the high-purity hydrofluoroether compound and specifically comprises the following steps of:
s01, distillation: the synthesized crude mixture of the hydrofluoroether is subjected to simple distillation to obtain a crude hydrofluoroether;
s02, adding and precipitating: removing water and deoxidizing the high-pressure airtight stainless steel reaction kettle to the oxygen content below 20 ppm; adding 0.05-2 parts of multifunctional branching initiator and 40-80 parts of crude hydrofluoroether into a high-pressure closed stainless steel reaction kettle according to parts by weight; stirring and heating to 40-95 ℃, reacting for 2-8 h, and cooling and discharging to obtain a reaction material;
the common glass kettle or enamel kettle cannot bear pressure, so the invention selects a high-pressure airtight stainless steel reaction kettle;
the multifunctional branching initiator adopts peroxy multifunctional branching initiator derived from beta-cyclodextrin, and the structural formula can be expressed as follows:
wherein β -CD represents a β -cyclodextrin group, n is an integer from 1 to 7;
s03, filtering: pressurizing and filtering the reaction material by a 150-350nm filter screen, and conveying the filtered liquid to a rectifying tower;
in the pressurizing and filtering process, only positive pressure is needed to be maintained or the conventional filtering effect can be achieved, namely, the pressurizing parameters are preferably in the pressure range of 0.1-2.0 MPa;
s04, rectifying: and (3) absorbing the filtered liquid mixture through two-stage rectification to obtain rectified liquid.
Finally, in step S02
According to the high-purity hydrofluoroether compound and the preparation method thereof, fluoroolefin or fluoroolefin ether and alcohol or phenol are mixed and then subjected to catalytic reaction to obtain a crude hydrofluoroether compound, a small amount of byproduct vinyl ether in the crude hydrofluoroether compound is subjected to reaction precipitation to separate out, and then conventional distillation and purification operations are carried out to obtain the high-purity hydrofluoroether compound. The addition reaction of the alcohol and the fluoroolefin is simple to operate, and the reaction condition is mild; the ions, high boiling point solvent and the like in the hydrofluoroether can be removed by distillation to obtain the hydrofluoroether containing by-products of unsaturated bonds, and the distillation temperature can be selected to be higher than the boiling point of the produced hydrofluoroether and lower than the temperature between the boiling points of the solvent; the method has the advantages of high efficiency, low comprehensive cost, simple treatment, no toxicity and environmental protection, and the prepared hydrofluoroether compound has high purity, especially the content of unsaturated bond compound is lower than 100ppm, can be used for cleaning microscopic instrument equipment and used as heat conduction medium and the like, and can be popularized and applied to the fields of cleaning liquid, heat exchange material, medium material and the like.
The method has the advantages of high efficiency, low comprehensive cost, simple treatment process, no toxicity, more environmental protection and the like, has less residual three wastes, meets the environmental protection requirement, and can save cost input; the cleaning agent can be used for cleaning microscopic instruments and equipment, can be used as a heat conduction medium and the like, and can be popularized and applied to the fields of cleaning liquid, heat exchange materials, medium materials and the like.
The specific operation content is as follows:
the method for obtaining the high-purity hydrofluoroether compound comprises the steps of distillation, addition precipitation, filtration and rectification of a hydrofluoroether crude product mixture;
the crude hydrofluoroether is obtained by catalytic reaction of fluoroolefin or fluoroolefin ether and alcohol or phenol, wherein the GC percent content of unsaturated byproducts is less than or equal to 25 percent;
the fluorovinyl ether is cmf2m+1-O-cf=cf2, wherein m is an integer of 1 to 6;
the alcohol is one of methanol, ethanol, isopropanol, 1-butanol, 2-butanol, 1, 2-propylene glycol, 1, 3-propylene glycol and fluoro alcohol; the phenol is one of phenol and fluorophenol;
the method comprises the following specific steps: according to the weight portions,
1) And (3) distilling: the synthesized mixture is subjected to simple distillation to obtain a crude hydrofluoroether product, and the crude hydrofluoroether product is sent to a high-pressure reaction kettle;
2) Adding and precipitating: removing water and deoxidizing in a high-pressure airtight stainless steel reaction kettle to the oxygen content below 20ppm, adding 0.05-2 parts of novel multifunctional branching initiator, 40-80 parts of the crude hydrofluoroether product in 1), stirring and heating to 40-95 ℃, reacting for 2-8 hours, and cooling and discharging;
3) And (3) filtering: pressurizing and filtering the materials obtained in the step 2) through a 150-350nm filter screen, and filtering out liquid and removing the liquid from a rectifying tower;
4) And (3) rectifying: 3) The liquid mixture is subjected to two-stage rectification and absorption to obtain the high-purity hydrofluoroether composition;
the functional multi-branched initiator is a beta-cyclodextrin derived peroxygen multi-functional branched initiator, which can be represented by the structural formula:
wherein beta-CD represents a beta-cyclodextrin group, and n is an integer of 1 to 7;
the method for obtaining the high-purity hydrofluoroether compound comprises the steps of reacting fluoroolefin or fluoroolefin ether with alcohol or phenol to obtain a crude hydrofluoroether mixture, carrying out polymerization precipitation on the crude hydrofluoroether obtained after simple distillation to remove unsaturated compounds in the crude hydrofluoroether, filtering to remove solids, and carrying out two-stage rectification to obtain the high-purity hydrofluoroether compound. Wherein the fluoroolefin is one of tetrafluoroethylene and hexafluoropropylene, the fluoroolefin ether is CmF2m+1-O-CF=CF2, and m is an integer of 1-6; the alcohol is one of methanol, ethanol, isopropanol, 1-butanol, 2-butanol, 1, 2-propylene glycol, 1, 3-propylene glycol and fluoro alcohol; the phenol is one of phenol and fluorophenol. The reaction product generally contains metal ions, solvents, crude hydrofluoroether and other components, the catalytic addition reaction has higher selectivity, the GC percent content of unsaturated byproducts can be controlled to be less than or equal to 25 percent in the synthesis stage, the ions, high-boiling point solvents and the like in the unsaturated byproducts can be removed through distillation, the hydrofluoroether of the byproducts containing unsaturated bonds is obtained, and the distillation temperature can be selected to be higher than the boiling point of the produced hydrofluoroether and lower than the temperature between the boiling points of the solvents.
The unsaturated compound is removed from the crude hydrofluoroether product through a polymerization precipitation process, wherein the removal process is that the unsaturated compound such as vinyl ether is subjected to addition polymerization under a novel multifunctional branching initiator to form free radical polyaddition, and then the obtained polymer containing a terminal initiator is precipitated to realize separation from the hydrofluoroether product. The technological process is as follows: removing water and deoxidizing in a high-pressure airtight stainless steel reaction kettle to the oxygen content below 20ppm, adding 0.05-2 parts of novel multifunctional branched initiator, 40-80 parts of distilled crude hydrofluoroether, starting stirring and heating to 40-95 ℃, and cooling and discharging after reacting for 2-8 hours, wherein the novel multifunctional branched initiator is a beta-cyclodextrin-derived peroxy multifunctional branched initiator, and the structural formula of the novel multifunctional branched initiator can be expressed as follows:
wherein beta-CD represents a beta-cyclodextrin group, and n is an integer of 1 to 7. Which is a multi-branched organic initiating compound derived from beta-cyclodextrin. Beta-cyclodextrin is a cone-barrel-shaped substance with narrow upper part and wide lower part, the wide lower part has larger steric hindrance, the active hydroxyl groups which react are fewer, the hydroxyl groups of the narrow upper part have higher activity due to the small steric hindrance, partial and complete derivatization reactions can be realized, and umbrella-like multi-branched products can be formed by utilizing the difference of the activities. The novel multifunctional branching initiator is produced by reacting beta-cyclodextrin with 1,3, 5-triacylchlorobenzene and then with tert-butyl hydroperoxide, and the reaction process is shown in figure 1.
The novel multifunctional branching initiator has good fluidity, and has super-large specific surface area by means of the cavity cooperation of beta-cyclodextrin, so that the unsaturated bonds capable of reacting are more effectively captured, the hydrofluoroether containing the unblanked compound is used as a solvent in the reaction, and the polymerization efficiency and the heat transfer stability are improved by the liquid-phase reaction, so that the reaction is easier to control and stabilize; the fluorine-containing part of the end initiator polymer generated by polymerization is dissolved and swelled to expose more initiator endpoints, the polymer chain is insoluble in the hydrofluoroether after being enlarged and the precipitation is finished, and the multi-branched initiation endpoints have quite important function of capturing trace unsaturated bonds;
the polymer precipitated by the invention is a granular substance with a shell-core-like structure, can be completely removed by pressure filtration through a filter screen with the diameter of 150-350nm, can not cause the blockage of the filter screen, and can be reused only by simple cleaning and purging. In order to ensure the purity, the filtered product is subjected to two-stage rectification to obtain the high-purity hydrofluoroether compound.
The invention also discloses a high-purity hydrofluoroether compound, which is prepared by the method, has the unsaturated compound content of less than 100ppm, and can be used in the fields of cleaning of precise micro-instruments and equipment, heat conduction media and the like.
The following reaction etherification is carried out according to six raw material combination modes in table 1 to prepare a crude hydrofluoroether mixture, and the comparison of examples one to nine and comparative examples 1 to 2 proves that the high-purity hydrofluoroether compound of the invention and the preparation method thereof.
Table 1:
embodiment one:
according to the operation steps of the steps S01 to S04, adopting a crude mixture of FE-1 hydrofluoroether, wherein the addition amount is 40 parts; the addition amount of the novel multifunctional branching initiator is 0.02 part, n=4; the addition and precipitation temperature is 80 ℃, the addition and precipitation time is 4 hours, and the fineness of the filter screen is 350nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.90%, and the content of unsaturated compounds is 80ppm.
Embodiment two:
according to the operation steps of the steps S01 to S04, a crude mixture of FE-2 hydrofluoroether is adopted, and the addition amount is 60 parts; the addition amount of the novel multifunctional branching initiator is 1 part, and n=6; the addition and precipitation temperature is 70 ℃, the addition and precipitation time is 4 hours, and the fineness of the filter screen is 220nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.95%, and the content of unsaturated compounds is 50ppm.
Embodiment III: according to the operation steps of the steps S01 to S04, a crude mixture of FE-3 hydrofluoroether is adopted, and the addition amount is 60 parts; the addition amount of the novel multifunctional branching initiator is 2 parts, and n=1; the addition and precipitation temperature is 70 ℃, the addition and precipitation time is 2 hours, and the fineness of the filter screen is 220nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.85%, and the content of unsaturated compounds is 100ppm.
Embodiment four: according to the operation steps of the steps S01 to S04, an FE-2 hydrofluoroether crude product mixture is adopted, and the addition amount is 80 parts; the addition amount of the novel multifunctional branching initiator is 0.8 part, n=3; the addition and precipitation temperature is 60 ℃, the addition and precipitation time is 6 hours, and the fineness of the filter screen is 100nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.88%, and the content of unsaturated compounds is 80ppm.
Fifth embodiment: according to the operation steps of the steps S01 to S04, a crude mixture of FE-3 hydrofluoroether is adopted, and the addition amount is 50 parts; the addition amount of the novel multifunctional branching initiator is 1.5 parts, n=7; the addition and precipitation temperature is 95 ℃, the addition and precipitation time is 8 hours, and the fineness of the filter screen is 300nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.89%, and the content of unsaturated compounds is 90ppm.
Example six: according to the operation steps of the steps S01 to S04, a crude mixture of FE-4 hydrofluoroether is adopted, and the addition amount is 60 parts; the addition amount of the novel multifunctional branching initiator is 0.5 part, n=6; the addition and precipitation temperature is 80 ℃, the addition and precipitation time is 6 hours, and the fineness of the filter screen is 300nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.88%, and the content of unsaturated compounds is 95ppm.
Embodiment seven: according to the operation steps of the steps S01 to S04, an FE-5 hydrofluoroether crude product mixture is adopted, and the addition amount is 80 parts; the addition amount of the novel multifunctional branching initiator is 1.5 parts, n=5; the addition and precipitation temperature is 40 ℃, the addition and precipitation time is 4 hours, and the fineness of the filter screen is 220nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.98 percent, and the content of unsaturated compounds is 50ppm.
Example eight: according to the operation steps of the steps S01 to S04, a crude mixture of FE-4 hydrofluoroether is adopted, and the addition amount is 60 parts; the addition amount of the novel multifunctional branching initiator is 0.3 part, n=6; the addition and precipitation temperature is 80 ℃, the addition and precipitation time is 6 hours, and the fineness of the filter screen is 150nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.95%, and the content of unsaturated compounds is 80ppm.
Example nine: according to the operation steps of the steps S01 to S04, adopting a crude mixture of FE-6 hydrofluoroether, wherein the addition amount is 40 parts; the addition amount of the novel multifunctional branching initiator is 0.1 part, n=4; the addition and precipitation temperature is 60 ℃, the addition and precipitation time is 4 hours, and the fineness of the filter screen is 150nm.
The preparation process is normal and can be easily controlled, the purity of the finally prepared high-purity hydrofluoroether composition is 99.93 percent, and the content of unsaturated compounds is 90ppm.
Comparative example 1: the procedure of the foregoing S01 to S04 was followed, but the same crude FE-2 hydrofluoroether mixture as in example 2 was used without the addition precipitation step, and the resulting high-purity hydrofluoroether composition had an unsaturated compound content of 20%, but it was difficult to filter the mixture at a later stage in the production process and to clean the filter screen.
Comparative example 2: according to the operation steps of the above steps S01-S04, adopting FE-2 hydrofluoroether crude product mixture, adopting tert-butyl triperoxide as addition precipitation initiator, while the beta-cyclodextrin is not combined with the invention, the adding amount of the tert-butyl triperoxide of the tribenzoic acid is 6 parts, and n=6; the addition and precipitation temperature is 70 ℃, the addition and precipitation time is 4 hours, and the fineness of the filter screen is 220nm.
Although the content of the unsaturated compound in the finally produced high-purity hydrofluoroether composition is 0.5%, minute particles appear after rectification during the production thereof.
Comparative example 1 is a chemical purification method without addition precipitation according to the present invention, and the advantages and necessity of addition precipitation are highlighted only by means of simple distillation, filtration, rectification, etc. in the present invention.
The comparative example 2 uses a chemical method to purify the impurities, but only through one part of the branched initiator of the invention (t-butyl trimellitate, which is the initiating group part), without the beta-cyclodextrin binding, thus highlighting the advantages and synergy of the novel initiator two part combination; the comparison result is: the two comparative examples are quite different from the examples of the present invention in terms of purity and unsaturated impurity content, thereby highlighting the advantages of the chemical impurity removal and purification of the present invention.
Comparative verification results for examples one to nine and comparative examples 1 to 2 are shown in table 2:
table 2:
compared with the prior art, the high-purity hydrofluoroether compound and the preparation method thereof have the following technical characteristics:
1. the purity of the product is high, the purity of the hydrofluoroether is more than or equal to 99.85 percent, and the content of unsaturated compounds is lower than 100ppm;
2. the efficiency is high, the comprehensive cost is low, the process steps are simple and easy to control, no harm is produced to equipment, human bodies and the like, and the requirements of a modern high-quality green industrial system are met;
3. the product has wide application range, and can be applied to the cleaning of higher-end precise micro-instrument equipment and used as a heat conduction medium.
The invention is not limited to the above-described alternative embodiments, and any person who may derive other various forms of products in the light of the present invention, however, any changes in shape or structure thereof, all falling within the technical solutions defined in the scope of the claims of the present invention, fall within the scope of protection of the present invention.
Claims (10)
1. A high purity hydrofluoroether compound characterized by: the method is characterized in that the hydrofluoroether crude product mixture is obtained through the steps of distillation, addition precipitation, filtration and rectification.
2. The high purity hydrofluoroether compound of claim 1, wherein: the crude hydrofluoroether is prepared by mixing fluoroolefin or fluoroolefin ether with alcohol or phenol, adding alkaline substances and solvents, and carrying out catalytic etherification reaction.
3. The high purity hydrofluoroether compound of claim 2, wherein: the GC percentage content of unsaturated byproducts in the crude hydrofluoroether product is less than or equal to 25 percent.
4. The high purity hydrofluoroether compound of claim 2, wherein: the fluoroolefin is tetrafluoroethylene or hexafluoropropylene.
5. The high purity hydrofluoroether compound of claim 2, wherein: the fluorovinyl ether is cmf2m+1-O-cf=cf2, wherein m is an integer of 1 to 6.
6. The high purity hydrofluoroether compound of claim 2, wherein: the alcohol is methanol, ethanol, isopropanol, 1-butanol, 2-butanol, 1, 2-propylene glycol, 1, 3-propylene glycol or fluoro alcohol.
7. The high purity hydrofluoroether compound of claim 2, wherein: the phenol is phenol or fluorophenol.
8. A process for producing a high-purity hydrofluoroether compound of any one of claims 1 to 8, characterized by comprising: the method comprises the following steps:
s01, distillation: the synthesized crude mixture of the hydrofluoroether is subjected to simple distillation to obtain a crude hydrofluoroether;
s02, adding and precipitating: removing water and deoxidizing the high-pressure airtight stainless steel reaction kettle to the oxygen content below 20 ppm; adding 0.05-2 parts of multifunctional branching initiator and 40-80 parts of crude hydrofluoroether into a high-pressure airtight stainless steel reaction kettle according to parts by weight; stirring and heating to 40-95 ℃, reacting for 2-8 h, and cooling and discharging to obtain a reaction material;
s03, filtering: pressurizing and filtering the reaction material by a 150-350nm filter screen, and conveying the filtered liquid to a rectifying tower;
s04, rectifying: and (3) absorbing the filtered liquid mixture through two-stage rectification to obtain rectified liquid.
9. The process for producing a highly pure hydrofluoroether compound of claim 8, wherein: the multifunctional branching initiator in the step S02 is a peroxy multifunctional branching initiator derived from beta-cyclodextrin, and the structural formula is as follows:
wherein beta-CD represents a beta-cyclodextrin group, and n is an integer of 1 to 7.
10. The process for producing a highly pure hydrofluoroether compound of claim 8, wherein: the pressure of the pressure filtration in the step S03 is 0.1 to 2.0MPa.
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