Process for preparing fluorinated alcohols

Abstract

To provide a method for preparing a partially fluorinated alcohol (fluorohydrin) from a fluorinated epoxide, and a method for preparing a fluorinated carbonate from a fluorohydrin.SOLUTION: Methods for preparing partially fluorinated alcohols (fluorohydrins) include, for example, preparing a fluorohydrin by reacting a fluorinated epoxide with a fluorinating agent (Olah's reagent) to effect ring opening, as in the following equation: Further, by reacting the obtained fluorohydrin with phosgene, it is possible to prepare the corresponding carbonic acid ester.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a process for preparing partially fluorinated alcohols (fluorohydrins) from fluorinated epoxides, and to a process for preparing fluorinated carbonates from fluorohydrins. [Background technology]

[0002] Fluorohydrins are useful as solvents and as synthetic building blocks from which a variety of species, such as esters, ethers, ketones, aldehydes, and acids, can be prepared. Of particular interest is their utility in the preparation of fluorinated carbonates, an important class of materials with significant commercial value. Fluorinated carbonates are commonly used without modification as synthetic intermediates and as solvents in electronic devices such as batteries (e.g., lithium-ion batteries), and to manufacture products such as lubricants, sealants, and coatings.

[0003] The production of fluorohydrins from epoxides is known in the art.For example, Olah describes a general method for preparing fluorohydrins by ring-opening epoxides with a nucleophilic source of fluoride (GA Olah et al, Israel Jr. Chem., 17 (1978), 148-149).However, Olah did not extend this work to the preparation of fluorohydrins from fluorinated epoxides.

[0004] The ring-opening of the fluorinated epoxide, 2,3-epoxy 1,1,1-trifluoropropane (TFPO), with various nucleophiles to form fluorohydrins was reviewed in a discussion of the chemical reactions of TFPO by Uneyama Jr. in Fluorine Chem., 105 (2000) 285-293. However, this discussion did not address the possibility or potential results of attempting the ring-opening of TFPO, or indeed any other fluorinated epoxide, with the nucleophilic fluorinating agents taught by Olah.

[0005] General methods for producing carbonate esters from alcohols and carboxylating agents are known in the art, see, for example, "March's Advanced Organic Chemistry," M.B. Smith and J. March, 6 th See, e.g., Vol. 1, No. 1, pp. 1276. However, the formation of a fluorinated carbonate from a fluorohydrin and a carboxylating agent as a product of such a reaction is unknown. DISCLOSURE OF THE INVENTION

[0006] According to a first aspect of the present invention, there is provided a process for preparing a partially fluorinated alcohol, comprising: [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl) with a fluorinating agent.

[0007] Preferably, R 1 ~R 4 At least one of comprises F, CF3, or fluoroalkyl.

[0008] Preferably, the fluorinating agent comprises a nucleophilic fluorinating agent, examples of which include HF and complexes of HF with nitrogen-containing species such as Oller's reagent (HF:pyridine complex), complexes of HF with urea, or complexes of HF with tertiary amines.

[0009] The method can include reacting the epoxide of 3,3,3-trifluoropropene (1243zf) with HF and / or Oller's reagent to form CF3CH(OH)CH2F. [ka]

[0010] The method can include reacting the epoxide of 1,3,3,3-tetrafluoropropene (1234ze) with HF and / or Oller's reagent to form CF3CH(OH)CHF2. [ka]

[0011] The method can include reacting the epoxide of 1,1,1,4,4,4-hexafluoro-2-butene (1336mzz) with HF and / or Oller's reagent to form CF3CH(OH)CHF(CF3). [ka]

[0012] The method can include reacting the epoxide of 1,1,3,3,3-pentafluoropropene (1225zc) with HF and / or Oller's reagent to form CF3CH(OH)CF3. [ka]

[0013] Compounds and compositions of the present invention According to a second aspect of the present invention, a structure [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl), with the proviso that the compound is not 1,1,1,3-tetrafluoropropan-2-ol.

[0014] The compounds of the second aspect of the invention may be used in the preparation of carbonate esters.

[0015] According to a third aspect of the present invention, there is provided a process for preparing a partially fluorinated carbonate ester having the structure: [ka] Fluorohydrin [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group comprising H, F, Cl, Br, I, CF, alkyl, fluoroalkyl, haloalkyl) with COX2, where X is selected from the group comprising —F, —Cl, —OCH3, —OCCl3, imidazole, succinimidyl.

[0016] Preferably, 2 equivalents of fluorohydrin are used per equivalent of COX2 (on a molar basis).

[0017] Alternatively, one equivalent of a fluorohydrin of the present invention can be used with one equivalent of an alcohol species (branched or linear monohydric / polyhydric alcohol) to prepare an asymmetric carbonate ester.

[0018] Compounds produced by the method according to the third aspect of the invention are covered by the fourth aspect of the invention. According to the fourth aspect of the invention, [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 are independently selected from the group including H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl.

[0019] The compounds of the fourth aspect of the present invention can also be used as battery solvent components (e.g., in lithium-ion batteries). The compounds herein have been found to be beneficial as a result of their physical properties, electrochemical stability, compatibility with battery components such as battery electrodes (cathode and anode) including carbon- and silicon-containing electrodes, lithium-containing electrolyte salts, separators, binders, and current collectors, and low flammability.

[0020] The compounds of the fourth aspect of the invention may also be used with other solvents and additives, such as other linear and cyclic carbonates.

[0021] Preferably, when used as a solvent, the composition comprises an electrolyte salt, preferred examples of which include lithium-based electrolytes such as those selected from the group including lithium hexafluorophosphate (LiPF), lithium triflate (LiSOCF), lithium bis(fluorosulfonyl)imide (Li(FSO)N), and lithium bis(trifluoromethanesulfonyl)imide (Li(CFSO)N).

[0022] The compounds of the second aspect of the present invention can be used to prepare (higher) fluorinated derivatives. One or more of the R groups may be substituted with fluorine. The R groups modified by fluorination in this process are preferably selected from the group including H, Cl, Br, and I.

[0023] The preparation process for fluorinated derivatives may include a multi-step process, preferably a two-step process, depending on the nature of the R group to be modified. In a preferred two-step process, the first step is to modify the target R group to a (different) halogen group, preferably a chlorine group (using a suitable chlorinating agent such as chlorine), and the second step is to modify the chlorine group to a fluorine group (using a suitable fluorinating agent such as HF, or a metal fluoride salt such as NaF or KF). It will be understood that if the target R group already contains a halogen other than fluorine, the two-step process of replacing the halogen with chlorine may not be necessary.

[0024] Therefore, the compound [ka] (In the formula, R 1 ~R 4 at least two of which independently contain H, Cl, Br, I) can be converted to (more highly) fluorinated derivatives.

[0025] R in fluorinated derivatives 1 ~R 4 Preferably, at least two, more preferably at least three of R independently comprise F, CF, or fluoroalkyl. 1 ~R 4 and more preferably at least one of R 1 ~R 4 and one of R independently contains H. Most preferably, 1 ~R 4 One of the groups contains CF3 and R 1 ~R 4 Two of them contain F and R 1 ~R 4 One of the groups comprises H. Most preferably, the fluorinated derivative comprises hexfluroroisopropanol.

[0026] compound [ka] (The preferred alternative is ·R 1 is -CF3 and R 2 is H and R 3 and R 4 Both are H. ·R 1 is -CF3 and R 2 is H and R 3 and R 4 One of the is H and R 3 and R 4One of the reactions is F) resulting in a favorable reaction pathway.

[0027] This preferred route is shown below. [ka] X is either F or Cl.

[0028] Epoxides useful in the first aspect of the present invention can be prepared from fluorinated alkenes. According to a fifth aspect of the present invention, there is provided a process for preparing partially fluorinated epoxides, comprising: [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group including H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl) with an oxidizing agent.

[0029] Preferably, R 1 ~R 4 At least one of comprises F, CF3, or fluoroalkyl.

[0030] Preferred examples of oxidizing agents include air, oxygen, and oxygen-containing compounds such as peroxides, persalts, and compounds of oxygen with other elements such as hypohalites. Preferably, the oxidizing agent comprises a hypohalite such as chlorite.

[0031] Preferably, the compound reacted with the oxidizing agent is tetrafluoropropene. Most preferably, R 1 and R 2 One of the groups is -CF3, and R 3 and R 4One of the groups is -F. Thus, the tetrafluoropropene is 1,3,3,3-tetrafluoropropene (1234ze) or 2,3,3,3-tetrafluoropropene (1234yf).

[0032] According to a sixth aspect of the present invention, there is provided a method for preparing a fluorohydrin comprising the fifth and first aspects of the present invention.

[0033] According to a seventh aspect of the present invention, there is provided a process for preparing a partially fluorinated ether having the structure: [ka] structure [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group including H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl.

[0034] According to an eighth aspect of the present invention, a structure [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 are independently selected from the group including H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl.

[0035] According to a ninth aspect of the present invention, there is provided a composition comprising a compound of the eighth aspect of the present invention.

[0036] The compound of the eighth aspect of the invention or the composition according to the ninth aspect of the invention may be used as a solvent, for example in battery applications.

[0037] The compound of the eighth aspect of the invention or the composition according to the ninth aspect of the invention may be used as a coolant, for example an immersion coolant.

[0038] Also provided is a method for preparing a partially fluorinated ether having the structure: [ka] structure [ka] (In the formula, R 1 , R 2 , R 3 , R 4 are independently selected from the group consisting of H, F, Cl, Br, I, CF, alkyl, fluoroalkyl, and haloalkyl; R 5 is independently selected from the group CF3, alkyl, fluoroalkyl, perfluoroalkyl, haloalkyl, perfluorohaloalkyl.

[0039] Preferably, ether synthesis occurs via the acid-catalyzed dehydration of a fluorohydrin.

[0040] Alternatively, ether synthesis occurs via one or more of the following techniques: i. Alkoxydehalogenation - reaction of alkyl halides with fluorohydrins, preferably under basic conditions; ii. Alkoxydesulfonyloxy substitution - reaction of a fluorohydrin sulfate with an alkoxide or a fluorohydrin alkoxide; iii. Hydro, alkoxy dediazodisubstitution - reaction of fluorohydrins with diazo compounds; iv. Alkoxy dehydroxylation - dehydration of two alcohols to give an ether, for example using concentrated sulfuric acid; v. Hydroxy or alkoxy dealkoxylation - Transesterification of (fluorohydrin) ethers with alcohols or fluorohydrins, and / or vi. Alkoxydehydroxylation - reaction of alcohols or fluorohydrins with oxonium compounds.

[0041] Additionally provided is a compound having the structure: [ka]

[0042] Also provided is a composition comprising a compound having the structure: [ka] The compound or composition may be used, for example, as a solvent in battery applications.

[0043] The compound or composition may be used as a coolant, for example, an immersion coolant.

[0044] The invention will now be described with reference to the following non-limiting examples. [Example]

[0045] Example 1 - Ring opening of epoxides using Oller's reagent The following steps were followed: The reactor was charged with Oller's reagent (70% HF:pyridine, 5 ml) and cooled with an ice batch while stirring. Then, 2,3-epoxy 1,1,1-trifluoropropane (TFPO) (3.4 g) was added dropwise. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirring was continued for 48 hours. After 48 hours, the reaction mixture was quenched with ice. Salt was added, and the product was extracted with diethyl ether (3 x 5 ml). The diethyl ether extracts were combined, washed with saturated potassium bicarbonate solution and water, and then dried over anhydrous sodium sulfate. The diethyl ether was removed in vacuo to give the desired product as a clear, colorless liquid with a boiling point of 91-93°C. The identity of this product was confirmed by NMR spectroscopy.

[0046] Example 2 - Ring opening of 2,3-epoxy-1,1,1,3-tetrafluoropropane using Oller's reagent [ka] The following procedure was used to ring open 2,3-epoxy-1,1,1,3-tetrafluoropropane. A 100 ml Hastalloy C pressure reactor was charged with Oller's reagent (70% HF:pyridine, 25 g). After sealing, the contents of the reactor were cooled to 20°C while stirring. Then 2,3-epoxy-1,1,1,3-tetrafluoropropane (11 g) was added. After the addition was complete, the reaction mixture was heated to 50°C and stirred for 168 hours. After 168 hours, the reaction mixture was quenched with ice and saturated sodium chloride solution (22 ml) was added. The product was extracted from this mixture using diethyl ether. The diethyl ether extracts were combined, washed with saturated potassium bicarbonate solution and then with water, and then dried over anhydrous sodium sulfate. The identity of the product was confirmed by NMR spectroscopy.

[0047] Example 2a - Ring opening of 2,3-epoxy-1,1,1,3-tetrafluoropropane using Oller's reagent [ka] The following procedure was used to ring open 2,3-epoxy-1,1,1,3-tetrafluoropropane. A 100 ml Hastalloy C pressure reactor was charged with Oller's reagent (70% HF:pyridine, 25 g). After sealing, the contents of the reactor were cooled to 20°C while stirring. Then 2,3-epoxy-1,1,1,3-tetrafluoropropane (10.6 g) was added. After the addition was complete, the reaction mixture was heated to 80°C and stirred for 43 hours. After 43 hours, a sample of the reaction mixture was analyzed by GCMS and it was found that all the feed epoxide had reacted. After cooling, the reaction mixture was quenched with ice and saturated sodium chloride solution (22 ml) was added. The product was extracted from this mixture using diethyl ether. The diethyl ether extracts were combined, washed with saturated potassium bicarbonate solution and then with water, and then dried over anhydrous sodium sulfate. The identity of the product was confirmed by NMR spectroscopy.

[0048] Example 3 - Ring opening of 2,3-epoxy-1,1,1-trifluoro-2-(trifluoromethyl)propane using Oller's reagent [ka] The following procedure was used to ring open 2,3-epoxy-1,1,1-trifluoro-2-(trifluoromethyl)propane. A 100 ml Hastalloy C pressure reactor was charged with Oller's reagent (70% HF:pyridine, 16.5 g). After sealing, the contents of the reactor were cooled to 20°C while stirring. Then, 2,3-epoxy-1,1,1-trifluoro-2-(trifluoromethyl)propane (10 g) was added. After the addition was complete, the reaction mixture was heated to 50°C and stirred for 160 hours. After 160 hours, the reaction mixture was quenched with ice and saturated sodium chloride solution (22 ml) was added. The product was extracted from this mixture using diethyl ether. The diethyl ether extracts were combined, washed with saturated potassium bicarbonate solution and then with water, and then dried over anhydrous sodium sulfate. The identity of the product was confirmed by NMR spectroscopy.

[0049] Example 4 - Preparation of di-(1,1,1,3-tetrafluoropropyl)carbonate using phosgene Di-(1,1,1,3-tetrafluoropropyl)carbonate was synthesized using the following procedure. Under an inert atmosphere, a three-necked round-bottom flask was cooled to 0°C. Phosgene solution (15 wt% in toluene, 50 mL of solution) was added and stirred. A mixture of 1,1,1,3-tetrafluoropropan-2-ol (18.42 g) and pyridine (11.02 g) was added dropwise to the solution, monitoring to ensure that the temperature of the solution did not rise above 10°C. The solution was warmed to room temperature and stirred for 48 hours. The product was filtered to remove the pyridinium salt and the solvent was removed in vacuo to give the crude product. The crude product was distilled under atmospheric pressure to give di-(1,1,1,3-tetrafluoropropyl)carbonate as a yellow oil (7.08 g, 35% yield). [Brief explanation of the drawings]

[0050] The figures show the results of various spectroscopic techniques performed on some of the reaction products from the examples.

[0051] [Figure 1] 1 shows the F NMR spectrum of the reaction product of 2,3-epoxy 1,1,1-trifluoropropane (TFPO) and Oller's reagent. [Figure 2] 1 shows the 19F NMR spectrum of the reaction product of 2,3-epoxy-1,1,1,3-trifluoropropane ring-opened with Oller's reagent. [Figure 2a-1]1 shows the proton-coupled 19F NMR spectrum of the reaction product of 2,3-epoxy-1,1,1,3-tetrafluoropropane ring-opened with Oller's reagent. [Figure 2a-2] 1 shows the proton-decoupled 19F NMR spectrum of the reaction product of 2,3-epoxy-1,1,1,3-tetrafluoropropane ring-opened with Oller's reagent. [Figure 3] Figure 1 shows the F NMR spectrum of the reaction product of 2,3-epoxy-1,1,1-trifluoro-2-(trifluoromethyl)propane ring-opened with Oller's reagent. [Figure 4] 1 shows the 19F NMR spectrum of the reaction product of 1,1,1,3-tetrafluoropropan-2-ol with phosgene, which matches the spectrum of the product di-(1,1,1,3-tetrafluoropropyl)carbonate.

[0052] The present invention includes the following aspects. [Aspect 1] 1. A process for preparing a partially fluorinated alcohol, comprising: [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl) with a fluorinating agent. [Aspect 2] The method of embodiment 1, wherein the fluorinating agent comprises a nucleophilic fluorinating agent. [Aspect 3] 3. The method of claim 1 or 2, wherein the fluorinating agent is selected from HF and a complex of HF with a nitrogen-containing species, such as Oller's reagent (HF:pyridine complex), a complex of HF with urea, or a complex of HF with a tertiary amine. [Aspect 4] The method of embodiment 3, wherein the ratio of HF to pyridine is 7:3 by weight. [Aspect 5] R 1 ~R 4 One of the groups is -CF3, and R 1 ~R 4 One of the is -F and R 1 ~R 4 Two of R are -H, preferably 1 is -F and R 3 is -CF3 and R 2 and R 4 is —H or preferably R 1 is -F and R 2 is -CF3 and R 3 and R 4 A method according to any one of aspects 1 to 4, wherein is —H. [Aspect 6] R 1 ~R 4 Two of the groups are -CF3 and R 1 ~R 4 Two of R are -H, preferably 1 is -CF3 and R 3 is -CF3 and R 2 But -H and R 4 A method according to any one of aspects 1 to 4, wherein is —H. [Aspect 7] R 1 ~R 4 One of the groups is -CF3, and R 1 ~R 4 three of R are -H, preferably 1 But -CF3, R 2 , R 3 , and R 4 A method according to any one of aspects 1 to 4, wherein is —H. [Aspect 8] R 1 ~R 4 One of the groups is -CF3, and R 1 ~R 4 one of R is -Cl; 1 ~R 4Two of R are -H, preferably 1 is -Cl, and R 3 is -CF3 and R 2 and R 4 is —H or preferably R 1 is -Cl, and R 2 is -CF3 and R 3 and R 4 A method according to any one of aspects 1 to 4, wherein is —H. [Aspect 9] structure [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl), provided that said compound is not 1,1,1,3-tetrafluoropropan-2-ol. [Aspect 10] A compound according to embodiment 9, formed by a process according to any one of embodiments 1 to 8. [Aspect 11] 1. A process for preparing a partially fluorinated carbonate ester having the structure: [ka] structure [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl) with COX2, where X is selected from the group consisting of -F, -Cl, -OCH3, -OCCl3, imidazole, succinimidyl. [Aspect 12] A compound having the following structure: [ka] [Aspect 13] A composition comprising a compound having the structure: [ka] [Aspect 14] Use of a compound according to embodiment 12 or a composition according to embodiment 13 as a solvent, for example in battery applications. [Aspect 15] A solvent composition comprising a compound according to embodiment 12 or a composition according to embodiment 13. [Aspect 16] 16. The solvent composition of embodiment 15, wherein the composition comprises an electrolyte comprising a lithium salt selected from the group comprising lithium hexafluorophosphate (LiPF), lithium triflate (LiSOCF), lithium bis(fluorosulfonyl)imide (Li(FSO)N), and lithium bis(trifluoromethanesulfonyl)imide (Li(CFSO)N). [Aspect 17] 1. A method for preparing a fluorinated compound, comprising the steps of: [ka] (In the formula, R 1 ~R 4 wherein at least two of the groups independently comprise H, Cl, Br, I) with a fluorinating agent. [Aspect 18] R in the fluorinated compound 1 ~R 4 wherein at least two of independently comprise F, CF3, or fluoroalkyl. [Aspect 19] R in the fluorinated compound 1 ~R 4 19. The method of embodiment 17 or 18, wherein at least one of [Aspect 20] 20. The method of embodiment 17, 18, or 19, wherein the fluorinated compound comprises hexfluroroisopropanol. [Aspect 21] 1. A process for preparing a partially fluorinated epoxide, comprising: [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl) with an oxidizing agent. [Aspect 22] 22. The method of embodiment 21, wherein the oxidizing agent is selected from the group comprising air, oxygen, and oxygen-containing compounds such as peroxides, persalts, and compounds of oxygen with other elements such as hypohalites. [Aspect 23] 23. The method of claim 21 or 22, wherein the oxidizing agent comprises a hypohalite, such as chlorite. [Aspect 23] 23. The method of embodiment 20, 21, or 22, wherein the alkene comprises a tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (1234ze) or 2,3,3,3-tetrafluoropropene (1234yf), or a pentafluoropropene, such as 1,1,3,3,3-pentafluoropropene (1225zc). [Aspect 24] A process for preparing a partially fluorinated alcohol, comprising: a process for preparing a partially fluorinated epoxide according to any one of aspects 20 to 23; and a process comprising reacting an epoxide according to any one of aspects 1 to 7. [Aspect 25] A process for preparing a partially fluorinated alcohol, comprising: a process for preparing a partially fluorinated epoxide according to any one of aspects 20 to 23; a process comprising reacting an epoxide according to any one of aspects 1 to 7; and a process for preparing a fluorinated compound according to any one of aspects 16 to 19. [Aspect 26] 1. A process for preparing a partially fluorinated ether having the structure: [ka] structure [ka] (In the formula, R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of H, F, Cl, Br, I, CF3, alkyl, fluoroalkyl, haloalkyl. [Aspect 27] A compound having the following structure: [ka] [Aspect 28] A composition comprising a compound having the structure: [ka] [Aspect 29] 29. Use of a compound according to embodiment 27 or a composition according to embodiment 28 as a solvent, for example in battery applications. [Aspect 30] Use of a compound according to embodiment 27 or a composition according to embodiment 28 as a coolant, for example as an immersion coolant. [Aspect 31] 1. A process for preparing a partially fluorinated ether having the structure: [ka] structure [ka] (In the formula, R 1 , R 2 , R 3 , R 4 are independently selected from the group consisting of H, F, Cl, Br, I, CF, alkyl, fluoroalkyl, and haloalkyl; R 5 is independently selected from the group CF3, alkyl, fluoroalkyl, perfluoroalkyl, haloalkyl, perfluorohaloalkyl. [Aspect 32] A compound having the following structure: [ka] [Aspect 33] A composition comprising a compound having the structure: [ka] [Aspect 34] 34. Use of a compound according to embodiment 32 or a composition according to embodiment 33 as a solvent, for example in battery applications. [Aspect 35] Use of a compound according to embodiment 32 or a composition according to embodiment 33 as a coolant, for example as an immersion coolant.

Claims

1. The following structure: 【Chemistry 1】 (In the formula, R １ , R ２ , R ３ , R ４ is independently selected from the group consisting of H, F, Cl, Br, I, alkyl and haloalkyl; R ５ is selected from the group comprising alkyl and haloalkyl.

2. R １ , R ２ , R ３ , R ４ is independently selected from the group consisting of H, F, Cl, Br, I, alkyl and fluoroalkyl.

3. R １ , R ２ , R ３ , R ４ is H, F, Cl, Br, I, alkyl and CF ３ 2. The compound of claim 1, independently selected from the group comprising:

4. R ５ The compound of any one of claims 1 to 3, wherein is selected from the group comprising alkyl and fluoroalkyl.

5. R ５ The compound of claim 4 , wherein is selected from the group consisting of alkyl, perfluoroalkyl, and perfluorohaloalkyl.

6. R ５ is alkyl, perfluorohaloalkyl and CF ３ 6. The compound of claim 5, selected from the group comprising:

7. A composition comprising a compound according to any one of claims 1 to 6.

8. The composition of claim 7 further comprising an electrolyte salt.

9. 9. The composition of claim 8, wherein the electrolyte salt is selected from the group comprising lithium-based electrolytes.

10. The lithium-based electrolyte is lithium hexafluorophosphate (LiPF ６ ), lithium triflate (LiSO ３ CF ３ ), lithium bis(fluorosulfonyl)imide (Li(FSO ２ ) ２ N), and lithium bis(trifluoromethanesulfonyl)imide (Li(CF ３ SO ２ ) ２ 10. The composition of claim 9, wherein the compound is selected from the group consisting of:

11. The composition of claim 7 further comprising at least one solvent or additive.

12. 12. The composition of claim 11, wherein the at least one solvent or additive is selected from the group consisting of linear and cyclic carbonates.

13. Use of a compound according to any one of claims 1 to 6 or a composition according to any one of claims 7 to 12 as a solvent.

14. 14. Use of the compound or composition of claim 13 as a solvent in battery applications.

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