CN109592655B - Method for efficiently preparing bis (fluorosulfonyl) imide through catalytic fluorination - Google Patents
Method for efficiently preparing bis (fluorosulfonyl) imide through catalytic fluorination Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for efficiently preparing bis (fluorosulfonyl) imide by catalytic fluorination. A method for efficiently preparing bis (fluorosulfonyl) imide through catalytic fluorination comprises the step of reacting bis (fluorosulfonyl) imide with hydrogen fluoride under the action of an organic alcohol compound catalyst to obtain bis (fluorosulfonyl) imide. The catalyst organic alcohol compound can catalyze the reaction of the bis-chlorosulfonyl imine and the hydrogen fluoride to obtain the bis-fluorosulfonyl imine. The simple organic matter has low cost, no introduction of other metal ion and high yield and purity.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for efficiently preparing bis (fluorosulfonyl) imide by catalytic fluorination.
Background
Fluorine-containing compounds generally show unique properties due to introduction of fluorine elements, and have important applications in the fields of polymer materials, liquid crystals, medicines and batteries, while fluorination technology is an important way to obtain such substances (t.ritter et al, org.process res.dev.,2014,18, 474; j.huet al, chem.rev.,2015,115(2), 765; t.ritter, Nature,2011,473,470.) bis-fluorosulfonyl imide (HFSI) is a fluorine-containing inorganic strong acid compound, and is mainly used as a key intermediate for preparing lithium bis-fluorosulfonyl imide (L FSI) (d.v. rajerner, coord.chem.rev.,1997(158), 413.; j.p.gurertin, incorg.syn, 1968 (138.), (m.berranal, z.anorg.631, alc.631., 631. h.p.gure., HFSI), and has significant advantages in terms of electrolyte synthesis, lithium batteries, HFSI, and electrolyte synthesis processes, such as compared with conventional lithium batteries.
The preparation of HFSI has been extensively studied by a large number of researchers. The first direct HFSI synthesis method using fluorosulfonic acid and urea was reported by Eisenhauer et al (g.eisenhauer et al, chem.ber.,1962,95,246.) as early as 1962, but has significant drawbacks: the yield is low and is only 61 percent at most; fluorosulfonic acid is expensive and highly corrosive; the boiling point of fluorosulfonic acid is too close to HFSI to be easily separated even by distillation. Therefore, the practical value of the method is not high.
On the other hand, starting from bischlorosulfonimide (HCSI), the preparation of HFSI by fluorination techniques has been studied more extensively. Such routes can be classified according to the fluorination reagents: a metal fluorinating agent; a hydrogen fluoride complex; anhydrous hydrogen fluoride alone. Ruff et al reported AsF in 19673Method of fluorination, US 8377406(B1) reports the use of BiF3As fluorinating agent, CN 101747242A was also reported to use SbF3As fluorinating agentsThe method of (1). However, these metal fluorinating agents are extremely toxic and expensive, and by-products such as SbCl are produced3Easy sublimation causes the disadvantage of difficult separation, and the like, so the industrial application value of the method is also limited (J.K. Ruff, Inorg.chem.,1967(6), 2108.). The specific reaction formula is as follows:
to avoid the use of expensive metal fluorinating reagents, inexpensive hydrogen fluoride is a good choice. CA2527802A1 reported the preparation of HFSI by reacting HCSI with anhydrous hydrogen fluoride gas, but the reaction took place after heating to 60 ℃ and only 55% yield was obtained even at 120-130 ℃ for 12 hours, thus the efficiency of single hydrofluoride fluorination was low. On the basis of this, CN 106219503a reports a method using hydrogen fluoride and an ether complex as a fluorinating agent, which is based on the principle that ether is used as a proton acceptor to complex with hydrogen fluoride to enhance the nucleophilicity of fluorine ions, and can significantly increase the yield of the reaction to 94-98% without high temperature. However, the disadvantage is that HFSI as a strong proton donor is also unstable due to solvation with the ether and decomposes.
CN 101654229A reports that Lewis acid of halide (F, Cl) of Ti, Sb, Ta, B and the like or compatibility with acyl fluoride compounds catalyzes the solvent-free reaction of hydrogen fluoride and HCSI in an autoclave, while CN 104925765A reports that the reaction is catalyzed by Lewis acid of chloride of Ti, Sb, Sn, Mo and the like, the catalyst dosage only needs 1 per thousand, the yield of 83% is obtained after short steaming and purification, the conclusion is concluded that the reaction efficiency is really and obviously improved under relatively mild conditions, the metal Lewis acid catalyst has certain industrial application value, but the metal catalyst and the byproduct thereof have the defects of easy sublimation and the like, the yield of HFSI is reduced by the additional treatment of double metal sulfimide, and the yield of HFSI is reduced by the method of environmentally friendly double metal sulfimide, namely the yield of HFSI is reduced by FSI and the risk of metal fluoride is reduced by the method of environmentally friendly double sulfimide, namely, the metal fluoride containing three wastes is reduced.
Therefore, based on the analysis of the existing HFSI synthesis technical route, it is significant to develop a non-metallic green catalyst for the reaction of HCSI and hydrogen fluoride, and to solve the defects of the technical route. However, no relevant catalyst has been developed so far.
Disclosure of Invention
In order to solve the technical problems, the first aspect of the invention provides a method for efficiently preparing bis (fluorosulfonyl) imide by catalytic fluorination, which comprises reacting bis (chlorosulfonyl) imide with hydrogen fluoride under the action of an organic alcohol compound catalyst to obtain bis (fluorosulfonyl) imide.
In a preferred embodiment, the organic alcohol compound is at least one selected from monohydric alcohols and polyhydric alcohols.
In a preferred embodiment, the organic alcohol compound is at least one selected from primary alcohols, secondary alcohols, tertiary alcohols, and heteroatom-substituted alcohols.
As a preferred technical scheme, the organic alcohol compound is primary alcohol.
In a preferable embodiment, the organic alcohol compound is a compound having 1 to 10 carbon atoms.
As a preferable technical scheme, the mole percentage of the catalyst organic alcohol compound to the bis-chlorosulfonyl imide is 0.1-20%, and preferably 0.5-5%.
As a preferable technical scheme, the molar ratio of the hydrogen fluoride to the bischlorosulfonimide is (1-50): 1, preferably (2-6): 1.
as a preferred technical scheme, the reaction temperature is 20-200 ℃, and preferably 60-120 ℃.
As a preferred embodiment, the reaction is carried out under normal pressure or under increased pressure, preferably under normal pressure.
As a preferred embodiment, the reaction is carried out in the absence of a solvent or an organic solvent, preferably in the absence of a solvent.
Has the advantages that: the catalyst organic alcohol compound can catalyze the reaction of the bis-chlorosulfonyl imine and the hydrogen fluoride to obtain the bis-fluorosulfonyl imine. The simple organic matter has low cost, no introduction of other metal ion and high yield and purity.
Detailed Description
For purposes of the following detailed description, it is to be understood that the invention may assume various alternative variations and step sequences, except where expressly specified to the contrary. Moreover, other than in any operating examples, or where otherwise indicated, all numbers expressing, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties to be obtained by the present invention. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements.
When a range of values is disclosed herein, the range is considered to be continuous and includes both the minimum and maximum values of the range, as well as each value between such minimum and maximum values. Further, when a range refers to an integer, each integer between the minimum and maximum values of the range is included. Further, when multiple range-describing features or characteristics are provided, the ranges may be combined. In other words, unless otherwise indicated, all ranges disclosed herein are to be understood to encompass any and all subranges subsumed therein. For example, a stated range from "1 to 10" should be considered to include any and all subranges between the minimum value of 1 and the maximum value of 10. Exemplary subranges of the range 1 to 10 include, but are not limited to, 1 to 6.1, 3.5 to 7.8, 5.5 to 10, and the like.
In order to solve the problems, the invention provides a method for efficiently preparing bis (fluorosulfonyl) imide by catalytic fluorination, which comprises the step of reacting bis (fluorosulfonyl) imide with hydrogen fluoride under the action of an organic alcohol compound catalyst to obtain bis (fluorosulfonyl) imide.
The catalytic fluorination reaction formula (1) is:
the chemical formula of the bis-fluorosulfonyl imide is HN (SO)2F)2HFSI for short, has a boiling point of 170 ℃ and a melting point of 17 ℃ and a CAS number of 14984-73-7.
Organic alcohol compound
In a preferred embodiment, the organic alcohol compound is at least one selected from the group consisting of monohydric alcohols and polyhydric alcohols.
Examples of polyols include, but are not limited to, ethylene glycol, propylene glycol, 1, 4-butanediol, 1, 6-hexanediol, glycerol, pentaerythritol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol.
As a preferred embodiment, the organic alcohol compound is at least one selected from primary alcohols, secondary alcohols, tertiary alcohols, and heteroatom-substituted alcohols.
Wherein, the term "heteroatom-substituted alcohol" refers to alcohol compounds substituted with heteroatoms such as nitrogen, sulfur, halogen, etc.
Examples of primary alcohols include, but are not limited to, methanol, ethanol, n-propanol, n-butanol, 2-methylpropanol, n-pentanol, n-hexanol, benzyl alcohol, phenethyl alcohol.
Examples of secondary alcohols include, but are not limited to, isopropanol, cyclopentanol, cyclohexanol, benzhydrol.
Examples of tertiary alcohols include, but are not limited to, t-butanol, t-amyl alcohol.
Examples of heteroatom-substituted alcohols include, but are not limited to, chloroethanol, fluoroethanol, trifluoroethanol, methoxyethanol, 2-dimethylaminoethanol, diacetone alcohol, 2-mercaptoethanol.
As a preferred embodiment, the organic alcohol compound is a primary alcohol.
In a preferred embodiment, the organic alcohol compound has 1 to 10 carbon atoms.
Examples of the organic alcohol compound include compounds having 1 to 10 carbon atoms, including but not limited to methanol, ethanol, chloroethanol, trifluoroethanol, ethylene glycol, propanol, butanol, and methoxyethanol.
In a preferred embodiment, the organic alcohol compound is a polyol compound having 1 to 10 carbon atoms.
In a preferred embodiment, the mole percentage of the organic alcohol compound and the bis-chlorosulfonyl imide in the catalyst is 0.1 to 20%, preferably 0.5 to 5%.
The applicant has found that the mole percentage of the organic alcohol compound to the bischlorosulfonimide of the catalyst is less than 0.1% or more than 20%, which reduces the catalytic efficiency or results in a reduction in the product yield.
In a preferred embodiment, the molar ratio of hydrogen fluoride to bischlorosulfonimide is (1 to 50): 1, preferably (2-6): 1.
as a preferred embodiment, the hydrogen fluoride is selected from at least one of gaseous hydrogen fluoride, liquid hydrogen fluoride, and hydrogen fluoride solution.
The hydrogen fluoride solution is not particularly limited, and hydrogen fluoride can be dissolved without impairing the object of the present invention. There may be exemplified acetonitrile solution, acetamide solution, tetrahydrofuran solution, ether solution, ethyl acetate solution and the like.
In a preferred embodiment, the reaction temperature is 20 to 200 ℃, preferably 60 to 120 ℃.
As a preferred embodiment, the reaction is carried out at atmospheric pressure or under pressure, preferably under atmospheric pressure.
The applicants have found that the hydrogen fluoride loss under pressurised conditions is lower, but the equipment requirements are high.
As a preferred embodiment, the reaction is carried out in the absence of a solvent or an organic solvent, preferably in the absence of a solvent.
In a preferred embodiment, the organic solvent is at least one selected from the group consisting of an aliphatic solvent, an aliphatic halide solvent, an ester solvent, a nitrile solvent, an aromatic solvent, an ether solvent, an amide solvent, a ketone solvent, a urea solvent, and water.
Examples of the aliphatic solvent include pentane, hexane, heptane, cyclohexane, petroleum ether, and the like.
Examples of the aliphatic halide solvent include dichloromethane, dichloroethane, chloroform, fluorotrichloromethane, 1,1, 2-trichloroethane, 2-chloro-1, 2-dibromo-1, 1, 2-trichloroethane, 1, 2-dibromohexafluoropropane, 1, 2-dibromotetrafluoroethane, 1, 1-difluorotetrachloroethane, 1, 2-difluorotetrachloroethane, heptafluoro-2, 3, 3-trichlorobutane, 1,1,1, 3-tetrachlorotetrafluoropropane, nitromethane, 1,1, 1-trichloropentafluoropropane, 1,1, 1-trichlorotrifluoroethane, and polychlorotrifluoroethylene.
Examples of the ester solvent include methyl formate, ethyl formate, methyl acetate, ethyl acetate, propyl acetate, methyl propionate, isopropyl acetate, γ -butyrolactone, and propylene carbonate.
Examples of the nitrile solvent include acetonitrile and propionitrile.
Examples of the aromatic solvent include benzene, toluene, ethylbenzene, propylbenzene, xylene, chlorobenzene, dichlorobenzene, fluorobenzene, trifluorotoluene, p-chlorotrifluoromethylbenzene, bromobenzene, nitrobenzene and the like.
Examples of the ether solvent include diethyl ether, dipropyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether.
Examples of the amide-based solvent include N, N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N-diethylformamide, hexamethyl-ortho-amide (HMPA), and the like.
Examples of the ketone solvent include 1-methyl-2-pyrrolidone, 1, 3-dimethyl-2-imidazolidinone, and the like.
Examples of the urea solvent include tetramethylurea and 1, 3-dimethylpropyleneurea.
The present invention will be specifically described below by way of examples. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and that the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above disclosure are still within the scope of the present invention.
In addition, the starting materials used are all commercially available, unless otherwise specified.
Examples
In examples 1 to 6, the acid value was measured by weighing 0.1g of a sample in a triangular flask, adding 50ml of water, and titrating with 0.1 mol/L KOH aqueous solution to obtain a KOH-consumed volume VKOH. The acid number is calculated as:
acid value (mg KOH/g) ═ 56.11 × 0.1 × VKOH)/m。
Wherein m is the sample mass, g; vKOHTo consume the volume of KOH, m L.
Example 1
A process for preparing a bischlorosulfonimide comprising the steps of: 825g of sulfamic acid and 1200g of chlorosulfonic acid were added to a 2000ml four-necked flask and the temperature was raised to 108 ℃. Beginning to drop 2730g of thionyl chloride, dropping for 12 hours, continuing to keep the temperature for 8 hours, and absorbing tail gas by water and liquid alkali. After the reaction is finished, water pump decompression is carried out to remove excessive thionyl chloride, then oil pump decompression rectification is carried out, 110 ℃/8.6mbar fractions are collected, 1386g of middle fractions are obtained, the acid value is 1076mgKOH/g, and the yield is 77%.
Example 2
A method for preparing bis (fluorosulfonyl) imide includes such steps as adding 1600g of bis (chlorosulfonyl) imide to 1000m L of PTFE reactor, stirring, adding 16g of methanol, heating to 100 deg.C, introducing 500g of anhydrous hydrogen fluoride at constant speed, reacting at 100 +/-5 deg.C for 16 hr, stopping reaction until the acid value is lowered to 340mgKOH/g or below, introducing nitrogen gas to purge for 4 hr to remove hydrogen fluoride, rectifying to obtain 60-62 deg.C/25 mbar fraction, collecting 1150g of middle fraction, acid value of 350mgKOH/g and yield of 85.0%.
1H-NMR(CDCl3)：7.81，s，1H。19F-NMR(CDCl3)：58.9。
Example 3
A method for preparing bis (fluorosulfonyl) imide includes such steps as adding 1200g of bis (chlorosulfonyl) imide to 1000m L of PTFE reactor, stirring, adding 11.2g of trifluoroethanol, heating to 105 deg.C, introducing 400g of anhydrous hydrogen fluoride gas at constant speed, maintaining the reaction temperature at 105 +/-5 deg.C for 12 hr, stopping reaction until the acid value is lowered to 340mgKOH/g or below, introducing nitrogen to purge for 4 hr to remove hydrogen fluoride, rectifying the crude product, collecting 60-62 deg.C/25 mbar fraction to obtain 898g of middle fraction with acid value of 332mgKOH/g, and obtaining 898g of product with 88.5% yield.
Example 4
A method for preparing bis (fluorosulfonyl) imide includes such steps as adding 1200g of bis (chlorosulfonyl) imide to 1000m L of PTFE reactor, stirring, adding 7g of ethanediol, heating to 110 deg.C, introducing 400g of anhydrous hydrogen fluoride at constant speed, reacting at 110 +/-5 deg.C for 12 hr, stopping reaction until the acid value is lower than 340mgKOH/g, introducing nitrogen to purge for 4 hr to remove hydrogen fluoride, rectifying, collecting 60-62 deg.C/25 mbar fraction to obtain 793g of middle fraction with acid value of 340mgKOH/g and yield of 78.2%.
Example 5
A method for preparing bis (fluorosulfonyl) imide includes such steps as adding 1200g of bis (chlorosulfonyl) imide to a 1000m L-autoclave, adding 10g of alcohol, adding 400g of liquid hydrogen fluoride, heating to 80 deg.C, holding the temp for 2 hr, releasing pressure, introducing nitrogen gas to purge it for 4 hr, rectifying, collecting 60-62 deg.C/25 mbar fraction to obtain 858g middle fraction, acid number 336mgKOH/g and yield 84.5%.
Example 6
A method for preparing bis (fluorosulfonyl) imide comprises the steps of adding 400g of bis (chlorosulfonyl) imide into a PTFE reactor with the volume of 1000m L, starting stirring, adding 3.3g of 2-dimethylaminoethanol, dropwise adding 310g of acetonitrile solution containing 30% hydrogen fluoride, heating to 60 ℃, reacting for 12 hours, carefully distilling off residual hydrogen fluoride and acetonitrile under reduced pressure, collecting fractions at the temperature of 60-62 ℃/25mbar to obtain 255g of middle fraction, wherein the acid value is 348mgKOH/g, and the yield is 75.3%.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in other forms, and any person skilled in the art may modify or change the technical content of the above disclosure into equivalent embodiments with equivalent changes, but all those simple modifications, equivalent changes and modifications made to the above embodiments according to the technical spirit of the present invention still belong to the protection scope of the present invention.
Claims (8)
1. A method for preparing bis (fluorosulfonyl) imide by catalytic fluorination at high efficiency is characterized by comprising the steps of reacting bis (fluorosulfonyl) imide with hydrogen fluoride under the action of an organic alcohol compound catalyst to obtain bis (fluorosulfonyl) imide;
the organic alcohol compound is selected from at least one of primary alcohol, secondary alcohol, tertiary alcohol and heteroatom substituted alcohol;
the mole percentage of the catalyst organic alcohol compound to the bis-chlorosulfonyl imide is 0.1-20%;
the molar ratio of the hydrogen fluoride to the bischlorosulfonimide is (1-50): 1;
the reaction temperature is 60-120 ℃.
2. The method according to claim 1, wherein the organic alcohol compound is at least one selected from the group consisting of monohydric alcohols and polyhydric alcohols.
3. The method of claim 1, wherein the organic alcohol compound is a primary alcohol.
4. The method according to claim 3, wherein the organic alcohol compound is a compound having 1 to 10 carbon atoms.
5. The method of claim 1, wherein the mole percentage of the catalyst organic alcohol compound to the bis-chlorosulfonyl imide is 0.5 to 5%.
6. The method of claim 1, wherein the molar ratio of hydrogen fluoride to bis-chlorosulfonyl imide is (2-6): 1.
7. the process of claim 1, wherein the reaction is carried out at atmospheric pressure or under elevated pressure.
8. The process of claim 1, wherein the reaction is carried out in the absence of a solvent or in an organic solvent.
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| US11591218B2 (en) | 2019-12-17 | 2023-02-28 | Honeywell International Inc. | Integrated processes for producing bis(fluorosulfonyl) imide |
| CN111410179B (en) * | 2020-03-31 | 2021-03-30 | 如鲲(山东)新材料科技有限公司 | Method for preparing bis (fluorosulfonyl) imide |
| US11772967B2 (en) | 2021-01-07 | 2023-10-03 | Honeywell International Inc. | Integrated processes for treatment of an ammonium fluorosulfate byproduct of the production of bis (fluorosulfonyl) imide |
| CN113104823A (en) * | 2021-03-26 | 2021-07-13 | 广州理文科技有限公司 | Synthesis method of bis (fluorosulfonyl) imide |
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