[0001 ] The present application claims priority to Canadian patent application

No 2,959,745 filed on February 28, 2017. This document is hereby incorporated by reference in its entirety.

FIELD OF THE DISCLOSURE

[0002] Lithium ion batteries and lithium polymer (LMP) batteries have superior properties compared to all other batteries. Such as a very high energy density, low self-discharge combined with negligible memory effect.

[0003] An ionic liquid or a salt molten at ambient temperature is a series of polar solvents having a very low viscosity, a very high ionic conductivity, and a high thermal and electrochemical stability. These salts are very sought after as electrolytes in electrochemical devices.

[0004] The different combinations of anions and cations give unlimited variations of salt and enable the generation of solvents having tailor-made physico- chemical properties.

[0005] In addition, these ionic liquids are:

• Non-volatile and

• Highly flame-resistant.

[0006] All these properties make said ionic liquids very attractive as replacements for the usual organic solvents in lithium ion batteries which are considered to be insufficiently safe.

[0007] The exothermic reaction generated in the first step of decomposition of the organic electrolytes in the lithium batteries involves a rapid decomposition of the electrolyte, which is catalyzed by the materials of electrodes of the battery and accelerated with heat. In addition, these electrolytes contain highly volatile organic solvents such as PC and DMC; the internal pressure of the battery can increase at any time and cause the battery to explode. If the battery is open to the air, these solvents function as a fuel, and, even if the battery remains closed, the materials of electrolytes catalyze a decomposition reaction with the electrolyte if the temperature reaches 200 °C following a short circuit or a collision.

[0008] Consequently, it is very urgent to replace the volatile and flammable organic electrolytes with another, safer system.

The Ionic Liquid Electrolytes (IL's)

1 - IL with the chloroaluminate anion

[0009] This is the first family of molten salt that has been studied for use in lithium ion batteries. Nevertheless, these salts are very sensitive to air, highly corrosive, and their use remains very problematic due to their cathodic instability with respect to the electrode lithium.

2- IL of alkylimidazolium and fluorosulfonimides.

[0010] Several ionic liquids with fluorinated anions are at the same time liquid at ambient temperature and have a good anodic stability and very low sensitivity to humidity, combined with a very low viscosity (e.g., EMI TFSI). Ideal properties for uses in lithium ion batteries. However, these salts undergo cathodic decomposition in the region of positive potential with respect to Li/Li ⁺ . In addition, an irreversible intercalation reaction of the carbocations inside the graphite layers at approximately 0.5 V vs. Li/Li ⁺ . This is the essential reason why researchers never have been able to manufacture lithium ion batteries with pure ionic liquids and without volatile and corrosive organic additives.

3- Why electrolytes based on FSI (bis(fluorosulfonyl)imide)?

[001 1 ] Ishikawa et al. (Journal of Power Sources 162 (2006) 658-662) have clearly demonstrated that the FSI-based ionic liquids, patent held by Hydro-Quebec, are the only known molten salts enabling the manufacture of lithium ion batteries with pure ionic liquids with very good results. [0012] This anion is the precursor of the very stable, highly conductive, liquid salts with very low viscosity. In addition, the FSI anion forms a passivation layer on the electrodes and prevents the undesirable reaction of the conventional ionic liquids (irreversible intercalation of the carbocations inside the electrodes).

[0013] FIG. 1 shows the complete absence of the common intercalation reaction of the conventional molten salts.

Known Methods for Synthesizing the FSI anion

[0014] The FSI anion has been very sought after for several years. Nevertheless, its preparation is very difficult and no known method allows its industrial production.

The action of the FS0 ₃ H acid on urea (Chem. Ber., 1962, 95, 246-248.)

o

FS0 ₃ H + H ₂ N-U-NH ₂ HFSI b _P 166 °C : _H ^N ₂ 0 ^4S ° ^3F bp l70 °C

-C O2

[0015] One difficulty is encountered, i.e., the fluorosulfonic acid is highly corrosive, very expensive and not readily available and it has practically the same boiling point as HFSI, which makes the purification of the latter impossible.

Protonation of N-sulfonyl trichlorophosphazene (Inorganic Chemistry

Communications, 1999, 2(6), 261 -264)

AsF ₃

FSO3H + CI0 ₂ S-N=PCI ₃ HFSI

-POCI3

Difficulties:

Use of fluorosulfonic acid.

Complicated and very expensive synthesis of trichlorophosph Use of extremely toxic arsenic fluoride Low yield Reaction of amidosulfuric with chlorosulfuric acid (Z. Anorg. Allg. Chem. 2005, 631, 55-59)

1 ) CIS0 ₃ H

2) 6KF

H2N-SO3H + SOCI ₂ KFSI

- 2HCI, -SO2, -HF

Difficulties:

• Corrosive and expensive reagents.

• Long time and high temperature (several days, from 80 to 180 °C)

• Heterogeneous reaction (insoluble reagent)

• Very low yield

• It is very difficult to transform KFSI into LiFSI

[0016] Therefore, it would be desirable to obtain a synthesis method and/or a novel chemical reagent that would make it possible to avoid and/or reduce at least one disadvantage of the prior art.

SUMMARY OF THE DISCLOSURE

[0017] The present disclosure relates to a compound of formula

The present disclosure also relates to the use of the compound having the above formula in the preparation of a compound comprising a fluorosulfonyl group: The present disclosure further relates to a method for preparing the compound of formula:

comprising reacting SO2F2 with imidazole, in the presence of a strong base.

The present disclosure also relates to a method for preparing the compound of formula:

O O comprising reacting L1NH2 with

[0021 ] The present disclosure also relates to a method for preparing the compound of formula:

+

i

comprising reacting

H ₂ N ≡N

with

[0022] The present disclosure also relates to a method for preparing the compound of formula:

comprising reacting

CH ₂ (CN) ₂ with

The present disclosure also relates to a method for preparing the compound of formula: comprising reacting

CF ₃ S0 ₂ NH ₂ with

The present disclosure also relates to a method for preparing the compound of formula:

comprising reacting

The present disclosure also relates to a method for preparing the compound of formula:

comprising reacting

[0026] The present disclosure also relates to a compound of formula:

or

[0027] The present disclosure also relates to the use a compound of formula:

or

in the manufacture of a polymer.

[0028] The present disclosure also relates to a compound of formula:

wherein n is an integer having a value 1 to 100.

[0029] The present disclosure also relates to a compound of formula:

wherein n is an integer having a value 1 to 100. BRIEF DESCRIPTION OF THE FIGURES

[0030] FIG. 1 (PRIOR ART) represents a cyclic voltammetry of the natural graphite in different ionic liquid electrolytes between 0 and 1 .2 V at a scan rate of 0.1 mVs ^"1 : (a) 0.8 M LiTFSI/EMI-TFSI; (b) 0.8 M LiTFSI/EMI-FSI; (c) 0.8 M UTFSI/P13-FSI.

DETAILED DESCRIPTION OF THE DISCLOSURE

[0031 ] The following examples are mentioned in a non-limiting manner.

[0032] For example, the compound comprising a fluorosulfonyl group can be chosen from:



and

For example, in the method for preparing the compound of formula:

in which the SO ₂ F ₂ is reacted with imidazole in the presence of a strong base, the strong base can be, for example, a base chosen from HMDS, LiHMDS, (tBu) ₃ N, triethylamine, methyllithium, buthyllithium, lithium diisopropylamide (LDA), LDEA, LiC03, pempidine, and the bases phosphazene bases (P1 -t-Bu, P2-Et, P2-F). [0034] For example, n can be an integer having a value 2, 3, 4, 5, 6, 7, 8, 9 or 10. [0035] For example, n can be an integer having a value 2, 3, 4 or 5. [0036] For example, n can be an integer having a value 2, 3 or 4. [0037] For example, n can be an integer having a value 2 or 3.

Precursor synthesis - novel reagent enabling the introduction of a SF02- group

[0038] N-fluorosulfonimide imidazole (2), (hereinafter "NFSI (2)" ), can be prepared from sulfuryl fluoride (1 ) marketed almost exclusively in North America by the company Dow Chemical under the commercial name Vikane™.

[0039] The process involves a reaction of imidazole with sulfuryl fluoride in the presence of a strong base in order to prepare the NFSI (2) according to the following Scheme 1 :

Scheme 1 :

(1 ) (2)

[0040] The NFSI (2) is purified by a simple distillation and can then be used as inexpensive and easy to handle, chlorine-free precursor.

Synthesis of the FSI anion

[0041 ] The reaction of NFSI (2) with a half-equivalent of LiNH ₂ followed by an acidification of the reaction medium would give, by direct synthesis, the desired LiFSI free of chlorine and of potassium.

Scheme 2:

(2) (3)

Synthesis of the anions stabilized with one or two nitrile groups

A. Synthesis of the anion FS0 ₂ NCN (4)

[0042] Also, the reaction of cyanamide with NFSI (2) by an addition-elimination reaction. The derealization of the negative charge on the molecule thus obtained, due to the CN and FSO2 group, would give it an increased electrochemical stability and thus improve the stability of the batteries with one less fluorine atom (more ecological).

Scheme 3:

O n ^Li+

H ₂ N ≡N

F— S— N » F— S N ^" __≡N

O O

(2) (4)

B. Synthesis of the FS0 ₂ CH(CN) ₂ anion

[0043] Another possibility would be to react the NFSI with malonitrile. In the interest of ecoresponsibility, this makes it possible to have an anion that is as effective as FSI but with less fluorine. Still with the purpose of obtaining extensive derealization of the negative charge, which gives an increased chemical and electrochemical stability to the anion.

Scheme 4:

(2) (5) . Synthesis of the FS0 ₂ NS0 ₂ CF ₃ anion

In addition, the NFSI (2) would make it possible to provide a novel, rapid and effective route of synthesis without chlorine (corrosive for the batteries) of the lithium N-(fluorosulfuryl)sulfonamide salt (6) from trifluoromethanesulfonamide (Aldrich).

Scheme 5:

(2) (6) rnthesis of novel monomers

[0045] The nucleophilic attack of the Grignard reagent on the product (2) would give the monomer (7).

Scheme 6:

[0046] Also, the allylamine can also react with (2) in a basic medium to give monomer

(8) according to the following scheme

Scheme 7:

(2) (8) Synthesis of novel electrolyte polymers from monomers 7 and 8.

[0047] It is possible to prepare the following polymers (9) and (10) (see schemes 8 and 9):

Scheme 8:

(2) (10)

[0048] The global market for lithium batteries for uses in vehicles is estimated to reach 221 billion USD by 2024.

[0049] The electrolytes of the lithium batteries continue to present problems in terms of stability, purity, safety and high cost.

[0050] The technology described in the present application proposes a novel synthesis route, without chlorine, of novel electrolyte polymers for the lithium batteries having chemically and electrochemical ly very stable fluorinated anions of low molecular weight. This synthesis route does not pass through chlorinated precursors. This is very important for simplifying the synthesis steps and the subsequent purifications. [0051 ] The electrolytes thus obtained can be free of any chlorine traces. The latter being very corrosive for lithium batteries.

[0052] It should be noted that such an economical route for synthesizing LiFSI (3) without chlorine, has been very sought after for years. Consequently, this route will rapidly have a large market and great economic benefits.

[0053] Moreover, NFS I (2) can be seen as a novel precursor that can have applications as:

• Auxiliary solvent for lithium batteries of the carbonate type; and

• Reagent enabling easy insertion of the FSO2- function in a biologically active target molecule (for example, bioisoteric replacement).

[0054] The present disclosure has been described above in reference to specific embodiments of the disclosure. Naturally, these embodiments that have just been described are only for exemplifying the technology and are in no case limiting, and various modifications can be made to the various subject matters that constitute the disclosure without leaving the scope of the present disclosure.