Method of manufacturing an organoboron salt

Abstract

The disclosure relates to a method of manufacturing an organoboron salt, the method comprising reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1-12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C, wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1, X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

Description

[0001] METHOD OF MANUFACTURING AN ORGANOBORON SALT

[0002] Field of the disclosure

[0003] The present disclosure relates to a method of manufacturing an organoboron salt. The organoboron salt may be a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1 - 12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

[0004] Background and summary

[0005] The present disclosure relates to a method of manufacturing an organoboron salt, such as a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1, X is a divalent cation and n is 2, or X is a trivalent cation and n is 3. Such compounds are useful as intermediates for the preparation of boron-containing compounds, such as battery electrolytes, additives, and alkali(ne earth) metal borohydrides.

[0006] Several methods for the manufacture of compounds according to formula (I) have been described. Reference can, for example, be made to Kemmit & Gainsford (2009) Int. J. Hydrogen Energy, 34, 5726-5731 and Lehmann & Tiess (1960) Z. anorg. allg. Chem., 304, 89-94.

[0007] Lehmann & Tiess describe that sodium tetramethoxy borate can be formed from e.g. Na4B2C>5, NasBsOe, NaB(OH)4, and hydrates of Na2B4O?. Similarly, they describe that lithium tetramethoxyborate can be manufactured from U3B3O6, UBO2 and hydrates thereof, and hydrates of U2B4O7, as well as that potassium tetramethoxyborate can be manufactured from K3B3O6, a hydrate of KBO2, hydrates of K2B4O7, and a hydrate of K2HB5O9.

[0008] Kemmit & Gainsford describe the alkanolysis of a hydrate of sodium borate to form sodium tetramethoxyborate and sodium tetraethoxyborate. They explain that higher alcohols (than methanol and ethanol) reacted much more slowly and required the use of higher reaction temperatures (than reflux temperature) accessed by the addition of toluene or xylene to the reactant alcohol. There is, thus, a need in the art for improved methods of manufacturing compounds according to formula (I). Particularly, there is a need for a method of manufacturing compounds according to formula (I) that has a broader scope (e.g., allows the use of higher alcohols), is (more) atom-economical, can be performed under mild conditions, and results in high yields of the compounds in, ideally, substantially pure form. The present disclosure provides such a method of manufacturing.

[0009] Accordingly, in a first aspect, the disclosure relates to a method of manufacturing an organoboron salt, the method comprising reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C, wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

[0010] The methods according to the disclosure, thus, involve reacting an ionic boron-oxygen compound, such as borax or a hydrate thereof, in the presence of a base and either an alcohol according to formula (II). The addition of the base enabled the conversion of the ionic boron-oxygen compound into a wide variety of organoboron compounds, thereby also enabling the manufacturing of important electrolytes directly from boron minerals (e.g. borax). This is surprising, because Kemmit & Gainsford reported that e.g. alkanolysis of sodium borate with higher alcohols (than methanol and ethanol) was slow and required higher temperatures that could only be achieved using the addition of toluene or xylene. In the present method, the scope of the reaction is unexpectedly fast, even when higher alcohols are used at relatively low temperatures. Moreover, because the reaction does not require the addition of any solvents that increase the boiling point of the reaction mixture, such as toluene or xylene, the method disclosed is also more atom-economical. It is also possible to obtain the organoboron salts in quantitative yield and in (substantially) pure form. In a further aspect, the disclosure relates to a method of processing an organoboron salt, wherein the method comprises the steps of reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C, wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3, and reacting the organoboron salt with a further reagent.

[0011] In the methods of processing the organoboron salt disclosed herein, the compound according to formula (I) is converted into a different product using the further reagent. For example, the compound according to formula (I) can be reacted with a hydride source, such as NaH, to form sodium borohydride, transesterified with an alcohol, a diol, or a dicarbonic acid or a salt thereof to form a different organoboron salts that can be used as, e.g. electrolytes. As another example, the compound according to formula (I) can be reacted with an ammonium salt or a phosphonium salt to exchange the cation X for the ammonium cation or the phosphonium cation, respectively.

[0012] RO 104207 B1 describes a synthesis of sodium ethylene glycol and glycerin borates as antistatic agents for polyesters.

[0013] Gainsford et al.: “Poly[tetrasodium(l)-tetra-[mu] 2-bis(butane-1,4-diyloxy)borato-[mu] 2-1,4- butanediol]”, Acta Crystallographies Section C. Crystal Structure Communications, vol. 61, no. 3, 28 February 2025, pgs. m136-m138, describes an addition of excess 1,4-butanediol to a solution of sodium metaborate in water.

[0014] Lehmann et al.: “Zur Chemie und Konstitution boraurer Salze. V Uber die Bildung von Methoxoboraten durch Methanolyse der Alkaliborate", Wissenschaftliche Zeitschrift der Technischen Hochschule „Carl Schorlemmer“ Leuna-Merseburg, vol. 2, 1 January 1959, pgs. 285-287, describes the methanolysis of alkali borates. It describes, for example, the methanolysis of borax.

[0015] Detailed description

[0016] The disclosure is described in detail below. As will be evident to the skilled person, different embodiments of the present disclosure can be combined unless they are mutually exclusive.

[0017] When amounts, concentrations, dimensions and other parameters are expressed in the form of a range, a preferable range, an upper limit value, a lower limit value or preferable upper and limit values, it should be understood that any ranges obtainable by combining any upper limit or preferable value with any lower limit or preferable value are also specifically disclosed, irrespective of whether the obtained ranges are clearly mentioned in the context.

[0018] Method of manufacturing the compound according to formula (I)

[0019] As mentioned, disclosed herein is a method of manufacturing an organoboron salt, the method comprising reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C, wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

[0020] The method, thus, results in the manufacture of the compound according to formula (I), X-[B- (OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1- 4)alkoxy, and wherein X is a monovalent cation and n is 1, X is a divalent cation and n is 2, or X is a trivalent cation and n is 3. The compound according to formula (I) comprises a monovalent, divalent, or trivalent cation: X. When X is a monovalent cation, n is 1. When X is a divalent cation, n is 2. And when X is a trivalent cation, n is 3. The cation can, in principle, be any cation, as the cation can originate from e.g. the ionic boron-oxygen compound and the base. It may be preferable that X originates from both the ionic boron-oxygen compound and the base, as this affords a (substantially) pure organoboron salt. Examples of monovalent cations include alkali metals, (such as Na, Li and K), (tetraalkyl)ammonium salts, and (tetraalkyl)phosphonium salts. Examples of divalent cations include alkaline earth metals, such as Ca and Mg, as well as metals such as Zn. Examples of trivalent cations include Al, Fe and Cr.

[0021] In some embodiments, X is Na, Li, or K and n is 1. In some embodiments, X is Na or Li and n is 1. In some embodiments, X is Na or K and n is i . In some embodiments, X is Na and n is 1. In some embodiments, the ionic boron-oxygen compound and the base comprise a cation X, wherein the cation X of the ionic boron-oxygen compound, the cation X of the base, and the cation X of the compound according to formula (I) are the same.

[0022] In some embodiments, X is Na, Li, or K, n is 1, and each R is independently selected from the group consisting of C(1 -12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy. In some embodiments, X is Na or Li, n is 1 , and each R is independently selected from the group consisting of C(1-12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy. In some embodiments, X is Na or K, n is 1, and each R is independently selected from the group consisting of C(1 - 12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy. In some embodiments, X is Na, n is 1, and each R is independently selected from the group consisting of C(1 - 12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy.

[0023] In some embodiments, X is Na, Li, or K, n is 1, and each R is independently selected from the group consisting of C(1 -12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen. In some embodiments, X is Na or Li, n is 1, and each R is independently selected from the group consisting of C(1- 12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen. In some embodiments, X is Na or K, n is 1 , and each R is independently selected from the group consisting of C(1 - 12)alkyl (optionally C(2- 10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen. In some embodiments, X is Na, n is 1 , and each R is independently selected from the group consisting of C(1 -12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen.

[0024] In particular embodiments, X is Na, n is 1 , and each R is independently selected from the group consisting of C(1-12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) and C(6- 10)aryl, each optionally substituted with one or more halogen. In particular embodiments, X is Na, n is 1 , and each R is independently selected from the group consisting of C(1-12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) and C(6-10)aryl, each substituted with one or more halogen. In particular embodiments, X is Na, n is 1 , and each R is independently selected from the group consisting of C(1 -12)alkyl (optionally C(2- 10)alkyl, in particular C(3- 8)alkyl) and C(6-10)aryl.

[0025] In particular embodiments, each R is independently selected from the group consisting of C(1-12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl) or C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy. In particular embodiments, each R is independently selected from the group consisting of C(1 - 12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl), each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy. In more particular embodiments, each R is independently selected from the group consisting of C(1 -12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl), each substituted with one or more halogen. In other particular embodiments, each R is independently selected from the group consisting of C(1 - 12)alkyl (optionally C(2-10)alkyl, in particular C(3-8)alkyl).

[0026] It may be preferred that, in the one or more compounds according to formula (II), R is selected from the group consisting of

[0027] - C(1 - 12)alkyl, in particular C(2- 10)alkyl, substituted with one or more halogen, and

[0028] - C(6-10)aryl, in particular C(6)aryl, substituted with one or more halogen.

[0029] Accordingly, it may be preferred that the one or more compounds according to formula (II) are selected from the group consisting of HOCF3, HOCH2CF3, HOCF2CF3, HOCH2CF2CF3, HOCF2CF2CF3, HOCH(CF3)2, HOCH2CF2CF2CF3, HOC(CF3)3, HOPhF, and HOCH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9. The use of such compounds allows commercially valuable products, such as electrolytes, to be formed directly from boron- containing materials, in particular boron-containing minerals.

[0030] In other embodiments, it may be preferred that, in the one or more compounds according to formula (II), R is the group consisting of C(1 -12)alkyl (optionally C(2- 10)alkyl, in particular C(3-8)alkyl) and C(6-10)aryl. For example, it may be preferred that the one or more compounds according to formula (II) are selected from the group consisting of HOCH3, HOCH2CH3, HOCH2CH2CH3, HOCH(CH3)2, HOCH2CH2CH2CH3, HOCH2CH(CH3)2, HOC(CH3)3, and HOPh. When these compounds are used, an intermediate product is formed, which can subsequently be converted in commercially valuable products, such as electrolytes or sodium borohydride.

[0031] It follows that the compound according to formula (II) may, in particular, be one or more selected from the group consisting of HOCH3, HOCF3, HOCH2CH3, HOCH2CF3, HOCF2CF3, HOCH2CH2CH3, HOCH2CF2CF3, HOCF2CF2CF3, HOCH(CF3)2, HOCH(CH3)2, HOCH2CH2CH2CH3, HOCH2CF2CF2CF3, HOCH2CH(CH3)2, HOC(CH3)3, HOC(CF3)3, HOPh, HOPhF, or HOCH2CH2(CF2)mCF3 wherein m is 1 , 3, 5, 7 or 9.

[0032] As will be clear to the skilled person, the R-groups in the compound according to formula (I) are derived from the one or more compounds according to formula (II). Thus, if the ionic boron-oxygen compound is reacted with one compound according to formula (II) and base, this will result in the formation of a compound according to formula (I) wherein the four OR- groups are the same. For example, if borax or a hydrate thereof is reacted with methanol and NaOH, the compound according to formula (I) will be NaB(OCH3)4. If the ionic boron-oxygen compound is reacted with two or more compounds according to formula (II) and base, this may result in the formation of a mixture of compounds according to formula (I). For example, if borax is reacted with a mixture of methanol and ethanol and NaOH, the following compounds according to formula (I) may form: NaB(OCH3)4, NaB(OCH2CH3)(OCH3)3, NaB(OCH2CH3)2(OCH3)2, NaB(OCH2CH3)3(OCH3), and NaB(OCH2CH3)4.

[0033] Non-limiting examples of the compound according to formula (I) are NaB(OCH3)4, NaB(OCF3)4, NaB(OCH2CH3)4, NaB(OCH2CF3)4, NaB(OCF2CF3)4, NaB(OCH2CH2CH3)4, NaB(OCH2CF2CF3)4, NaB(OCF2CF2CF3)4, NaB(OCH(CF3)2)4, NaB(OCH(CH3)2)4, NaB(OCH2CH2CH2CH3)4, NaB(OCH2CF2CF2CF3)4, NaB(OCH2CH(CH3)2)4, NaB(OC(CH3)3)4, NaB(OC(CF3)3)4, NaB(OPh)4, NaB(OPhF)4, NaB(OCH2CH2(CF2)mCF3)4 wherein m is 1 , 3, 5, 7 or 9.

[0034] Preferred compounds according to formula (I) are NaB(OCH3)4, NaB(OCF3)4, NaB(OCH2CH3)4, NaB(OCH2CF3)4, NaB(OCF2CF3)4, NaB(OCH2CH2CH3)4, NaB(OCH2CF2CF3)4, NaB(OCF2CF2CF3)4, NaB(OCH(CF3)2)4, NaB(OCH(CH3)2)4. The compound according to formula (I) may, in particular, be NaB(OCH3)4. The ionic boron-oxygen compound is selected from one or more of the group consisting of borax and hydrates thereof (in particular, borax, kernite, tincalconite, and tincal). Particularly, the boron-oxygen compound may be one or more selected from the group consisting of borax or hydrates thereof (in particular, borax, kernite, tincalconite, and tincal). Of these boron-containing materials, borax, kernite, tincalconite, and tincal may be preferred due to their good availability in nature.

[0035] The ionic boron-oxygen compound may be dehydrated prior to reacting it with the base and the compound according to formula (II), but this is not necessary. It may be preferred that, in the method of manufacturing the organoboron salt, the ionic boron-oxygen compound is not dehydrated.

[0036] The base used in the method according to the disclosure may be a hydroxide salt, such as a hydroxide of an alkali metal or a hydroxide of an alkaline earth metal, a carbonate salt, a bicarbonate salt, an oxide of an alkali metal, and / or an oxide of an alkaline earth metal. Examples of suitable bases are bases selected from the group consisting of NaOH, KOH, LiOH, Ca(OH)2, Mg(OH)2, Na2CO3, K2CO3, Li2CO3, CaCO3, MgCO3, NaHCO3, KHCO3, LiHCO3, Ca(HCO3)2, Mg(HCO3)2, Na2O, K2O, l_i2O, CaO, and MgO. When selecting a base, it is advantageous for the alkali metal(s) and / or the alkaline earth metal(s) present in the ionic boron-oxygen compound to be the same as the alkali metal(s) and / or the alkaline earth metal(s) present in the base. For example, if the ionic boron-oxygen compound is borax, kernite, tincalconite or tincal, the base is preferably NaOH, Na2CO3, NaHCO3, or Na2O. As another example, if the ionic boron-oxygen compound is colemanite, meyerhofferite, inyoite or pandermite, the base is preferably Ca(OH)2, CaCO3, Ca(HCO3)2, or CaO. As yet another example, if the ionic boron-oxygen compound is inderite, boracite or ascharite, the base is preferably Mg(OH)2, MgCO3, Mg(HCO3)2, or MgO.

[0037] The reacting may comprise using at least 1.0 moles of base per mole of cation in the ionic boron-oxygen compound, in particular at least 2.0 moles of base per mole of cation in the ionic boron-oxygen compound. The reacting may comprise using 1.0 to 12.0 moles of base per mole of cation in the ionic boron-oxygen compound, in particular 1 .0 to 5.0 moles of base per mole of cation in the ionic boron-oxygen compound.

[0038] The reacting comprises using the one or more compounds according to formula (II) in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound. It may be preferred that the reacting comprises using the one or more compounds according to formula (II) in a total amount of from 4.0 to 10 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, in particular a total amount of from 4.0 to 7.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, more in particular 4.0 to 4.3 moles of the compound according to formula (II) per mole of boron in the ionic boron- oxygen compound

[0039] The reacting preferably comprises using (the ionic boron-oxygen compound,) the base and the compound according to formula (II) in at least a stoichiometric amount. It is particularly preferred that the reacting comprises using (the ionic boron-oxygen compound,) the base and the compound according to formula (II) in a stoichiometric amount, as this results in a completely atom economical process and, thus, an essentially pure product when a boron- containing mineral is used as the ionic boron-oxygen compound. It is well within the capabilities of the skilled person to determine what is a stoichiometric amount by balancing the chemical equation and then determining appropriate amounts of reagent. As an example, the stoichiometric amounts of some preferred bases and compounds according to formula (II) have been listed below for a number of boron-containing materials.

[0040] *Equivalents as defined in this Table refer to the number of molar equivalents compared to 1 equiv. of the ionic boron-oxygen compound.

[0041] The reacting is carried out at a temperature of at least 20 °C. The reacting may preferably be carried out at a temperature of from 20 °C to the reflux temperature of the compound according to formula (II). Temperatures higher than reflux temperature are undesirable, because they can only be achieved with a complex process. For example, they can be achieved by adding a high-boiling point solvent (e.g., toluene or xylene), which reduces the atom efficiency of the method and may result in impurities. In some embodiments, the reacting is done at a temperature of from 50 to 200 °C, in particular at a temperature 50 to 90 °C, more in particular at a reflux temperature of the compound according to formula (II).

[0042] Water will usually be liberated during the reacting, for example from the ionic boron-oxygen compound, or be formed during the reacting. The presence of water is undesired, as water is detrimental to the yield of the reaction. Therefore, water is removed during the reacting. Preferably, the water is removed using a solid, water-absorbing material, such as molecular sieves (e.g. 3A molecular sieves or 4A molecular sieves), alumina, sodium sulfate, magnesium sulfate, or boron trioxide.

[0043] The reaction may be carried out under any atmosphere. It may be preferred for the reacting to be carried out under air or under an inert atmosphere (e.g. a nitrogen atmosphere or argon atmosphere).

[0044] The method according to the disclosure may be carried out under atmospheric pressure or under elevated pressure. For example, the reacting may be carried out under a pressure of 1.1 bar or more, such as a pressure of 1.5 bar or more. It is, however, preferred that the reacting is carried out under atmospheric pressure (1.0 bar).

[0045] The reactants (i.e., the ionic boron-oxygen compound, the base and the compound according to formula (II)) may be dosed at the same time or sequentially. In some embodiments, the reacting comprises contacting the ionic boron-oxygen compound with the base to form an intermediate, followed by contacting the intermediate with the compound according to formula (II). In other embodiments, the reacting comprises simultaneously contacting the ionic boron-oxygen compound with the base and the compound according to formula (II). In yet another embodiment, the compound according to formula (II) and the base may be combined to form an (optionally substituted) alkoxide, followed by contacting the compound according to formula (I) with the (optionally substituted) alkoxide.

[0046] As will now be clear, the method according to the disclosure affords the compound according to formula (I). This product is formed in (substantially) pure form. Accordingly, in the method according to the disclosure, the compound according to formula (I) may have a purity of at least 99.5%, in particular at least 99.9%, more in particular at least 99.99% (e.g. as determined by elemental analysis (optionally using ASTM E1621-22) and / or a combination of elemental analysis with XRD analysis and / or NMR spectroscopic analysis). For example, the compound according to formula (I) may contain less than 0.5% of trialkyl borate impurities, in particular at least 0.1 mol.% of trialkyl borate impurities, more in particular less than 0.01% of trialkyl borate impurities.

[0047] In particular embodiments, the method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 -12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

[0048] In particular embodiments, the method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 -12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

[0049] In particular embodiments, the method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, -CF2CF2CF3, -CH(CF3)2, - CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, -C(CH3)3I-C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3wherein n is 1 , 3, 5, 7 or 9, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, - CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, - C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3wherein n is 1 , 3, 5, 7 or 9, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

[0050] In particular embodiments, the method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of borax and hydrates thereof (in particular, borax, kernite, tincalconite, and tincal) with a base selected from the group consisting of NaOH, Na2CO3, NaHCO3, and Na2O (in particular, NaOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 - 12)alkyl (in particular C(2-10)alkyl, more in particular C(3- 8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Na, and n is 1.

[0051] In particular embodiments, the method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of borax and hydrates thereof (in particular, borax, kernite, tincalconite, and tincal) with a base selected from the group consisting of NaOH, Na2CO3, NaHCO3, and Na2O (in particular, NaOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 - 12)alkyl (in particular C(2-10)alkyl, more in particular C(3- 8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Na, and n is 1.

[0052] In particular embodiments, the method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of borax and hydrates thereof (in particular, borax, kernite, tincalconite, and tincal) with a base selected from the group consisting of NaOH, Na2CO3, NaHCCh, and Na2O (in particular, NaOH) and one or more compounds according to formula (II), R-OH, wherein R is -CH3, - CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, -CF2CF2CF3, -CH(CF3)2, - CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, -C(CH3)3I-C(CF3)3, -Ph, -PhF, and -OCH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, - CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, - C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, X is Na, and n is 1.

[0053] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of U4B2O5, LiBO2, LiBO2H2O, U2B4O7, and Li2B4Oy5H2O with a base selected from the group consisting of LiOH, U2CO3, UHCO3, and U2O (in particular, LiOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Li, and n is 1.

[0054] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of □46205, UBO2, UBO2 H2O, Li2B4O?, and U2B4O7 5H2O with a base selected from the group consisting of LiOH, U2CO3, UHCO3, and U2O (in particular, LiOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Li, and n is 1.

[0055] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of □46205, LiBO2, LiBO2H2O, Li2B4O?, and Li2B4Oy5H2O with a base selected from the group consisting of LiOH, Li2CO3, LiHCOs, and Li2O (in particular, LiOH) and one or more compounds according to formula (II), R-OH, wherein R is -CH3, -CF3, -CH2CH3, -CH2CF3, - CF2CF3, -CH2CH2CH3, -CH2CF2CF3, -CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, - CH2CF2CF2CF3, -CH2CH(CH3)2, -C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, - CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, - C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3wherein n is 1 , 3, 5, 7 or 9, X is Li, and n is 1.

[0056] Also described herein is a method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of

[0057] KsBsOe, KBO21 ,5H2O, K2B4O?, and K2B4Oy4H2O with a base selected from the group consisting of KOH, K2CO3, KHCO3, and K2O (in particular, KOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of 0(1-12)alkyl (in particular 0(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is K, and n is 1.

[0058] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of

[0059] KsBsOe, KBO21 ,5H2O, K2B4O?, and K2B4Oy4H2O with a base selected from the group consisting of KOH, K2CO3, KHCO3, and K2O (in particular, KOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of 0(1-12)alkyl (in particular 0(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is K, and n is 1.

[0060] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of K3B3O6, KBO2' 1 ,5H2O, K2B4O7, and K2B4O7 4H2O with a base selected from the group consisting of KOH, K2CO3, KHCO3, and K2O (in particular, KOH) and one or more compounds according to formula (II), R-OH, wherein R is -CH3, -CF3, -CH2CH3, -CH2CF3, - CF2CF3, -CH2CH2CH3, -CH2CF2CF3, -CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, - CH2CF2CF2CF3, -CH2CH(CH3)2, -C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, - CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, - C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, X is K, and n is 1.

[0061] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of colemanite, meyerhofferite, inyoite and pandermite with a base selected from the group consisting of Ca(OH)2, CaCCh, Ca(HCC>3)2, and CaO (in particular, Ca(OH)2) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Ca, and n is 2.

[0062] Also described herein is a method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of colemanite, meyerhofferite, inyoite and pandermite with a base selected from the group consisting of Ca(OH)2, CaCCh, Ca(HCC>3)2, and CaO (in particular, Ca(OH)2) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Ca, and n is 2.

[0063] Also described herein is a method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of colemanite, meyerhofferite, inyoite and pandermite with a base selected from the group consisting of Ca(OH)2, CaCCh, Ca(HCC>3)2, and CaO (in particular, Ca(OH)2) and one or more compounds according to formula (II), R-OH, wherein R is -CH3, -CF3, -CH2CH3, - CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, -CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, - CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, -C(CH3)3, -C(CF3)3, -Ph, -PhF, and - CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, - CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, - C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, X is Ca, and n is 2.

[0064] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of inderite, boracite and ascharite with a base selected from the group consisting of Mg(OH)2, MgCOs, Mg(HCC>3)2, and MgO (in particular, Mg(OH)2) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1- 12)alkyl (in particular C(2- 10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Mg, and n is 2.

[0065] Also described herein is a method of manufacturing an organoboron salt comprising reacting an ionic boron-oxygen compound selected from the group consisting of inderite, boracite and ascharite with a base selected from the group consisting of Mg(OH)2, MgCOa, Mg(HCC>3)2, and MgO (in particular, Mg(OH)2) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1- 12)alkyl (in particular C(2- 10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Mg, and n is 2.

[0066] Also described herein is a method of manufacturing an organoboron salt comprises reacting an ionic boron-oxygen compound selected from the group consisting of inderite, boracite and ascharite with a base selected from the group consisting of Mg(OH)2, MgCOa, Mg(HCOa)2, and MgO (in particular, Mg(OH)2) and one or more compounds according to formula (II), R-OH, wherein R is -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, - CH2CH2CH3, -CH2CF2CF3, -CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, - CH2CF2CF2CF3, -CH2CH(CH3)2, -C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3 wherein n is 1 , 3, 5, 7 or 9, in a total amount of from 4.0 to 10.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of -CH3, -CF3, -CH2CH3, -CH2CF3, -CF2CF3, -CH2CH2CH3, -CH2CF2CF3, - CF2CF2CF3, -CH(CF3)2, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CF2CF2CF3, -CH2CH(CH3)2, - C(CH3)3, -C(CF3)3, -Ph, -PhF, and -CH2CH2(CF2)nCF3wherein n is 1 , 3, 5, 7 or 9, X is Mg, and n is 2.

[0067] Method of processing the organoboron salt

[0068] The method of manufacturing the organoboron salt disclosed herein affords an organoboron salt having a structure according to formula (I), which can, in turn, be transformed into a number of commercially valuable materials by reacting it with a further reagent.

[0069] Accordingly, also disclosed herein is a method of processing the organoboron salt, wherein the method comprises the steps of manufacturing an organoboron salt, wherein the organoboron salt is a compound according to formula (I), according to the method of manufacturing disclosed herein, reacting the organoboron salt with a further reagent.

[0070] Suitable further reagents include, but are not limited to, a hydride source, water, (fluorinated) alcohols, diols, (di)carboxylic acids and their salts, ammonium salts, phosphonium salts, (boro)hydride salts, and organophosphorus compounds. Non-limiting examples of suitable alcohols include HOCF3, HOCH2CF3, HOCF2CF3, HOCH2CF2CF3, HOCF2CF2CF3, HOCH(CF3)2, HOCH2CF2CF2CF3, HOC(CF3)3, HOCH2CH2(CF2)nCF3wherein n is 1 , 3, 5, 7 or 9, and HOPhF. Non-limiting examples of suitable diols include perfluoropinacol. Non-limiting examples of suitable (di)carboxylic acids and their salts include oxalic acid, malonic acid, succinic acid, phtalic acid, isophtalic acid, tartaric acid, glycolic acid, and amino acids (e.g., glycine and valine), and salts thereof. Non-limiting examples of suitable ammonium salts include tetraalkylammonium salts, such as a tetramethylammonium salt or a tetraethylammonium salt. Non-limiting examples of suitable phosphonium salts include tetraalkylphosphonium salts, such as a tetramethylphosphonium salt or a tetraethylphosphonium salt.

[0071] Suitable reaction conditions are described in e.g. US 2001 / 0033964, US 2996534A, and US 2923731A. For example, US 2001 / 0033964 and US 2923731A describe methods suitable for cation exchange. US 2938920A describes methods suitable for transesterification of the compound according to formula (1(a)). These documents, in particular the methods described in their Examples, are incorporated by reference herein. It follows from the above that, in some embodiments, the method of processing the organoboron salt comprises the steps of manufacturing an organoboron salt, wherein the organoboron salt is a compound according to formula (I), according to the method disclosed herein, reacting the organoboron salt with a hydride source (such as a metal hydride (e,g. NaH, LiH, KH, CaH2 or MgH2), a borohydride salt (e.g., NaBH4, KBH4 or LiBFL), an aluminium hydride salt (e.g., LiAIFL or NaAIH4), diisobutylaluminium hydride, or tris(trimethylsilyl)silane).

[0072] In other embodiments, the method of processing the organoboron salt comprises the steps of manufacturing an organoboron salt, wherein the organoboron salt is a compound according to formula (I), according to a method disclosed herein, reacting the compound according to formula (I) with HOCH(CF3)2, HOCH2CF2CF2CF3, HOPhF, or perfluoropinacol, thereby forming an electrolyte.

[0073] If desired, the cation of the compound according to formula (I) or the electrolyte can be exchanged. Accordingly, disclosed herein is a method of processing the organoboron salt comprises the steps of manufacturing an organoboron salt, wherein the organoboron salt is a compound according to formula (I), according to a method disclosed herein, reacting the compound according to formula (I) with a cation source, thereby exchanging cation Xn+of the organoboron salt for another cation, optionally wherein the cation source is a salt having a cation selected from alkali metals (in particular, Li, Na, K, and Cs), alkaline earth metals (in particular, Mg and Ca), Zn, NH4, N[C(1-4)alkyl]4, P[C(1 -14)alkyl]4, imidazolium, pyrrolidinium, and piperidinium.

[0074] Also disclosed herein is method of processing the organoboron salt comprises the steps of manufacturing an organoboron salt, wherein the organoboron salt is a compound according to formula (I), according to the method disclosed herein, reacting the compound according to formula (I) with HOCH(CF3)2, HOCH2CF2CF2CF3, HOPhF, or perfluoropinacol, thereby forming an electrolyte, and reacting the electrolyte with an ammonium salt (in particular, a tetraalkylammonium salt) or a phosphonium salt (in particular, a tetraalkylphosphonium salt). The compound according to formula (I)

[0075] Also disclosed herein is a compound according to formula (I), X-B-(OR)4, wherein X is selected from the group consisting of Na, Li, K, and Mg and R is selected from the group consisting of C(1-6)alkyl, C(1-6)alkenyl, C(1-6)alkynyl, and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, characterized in that the compound is obtained by the method of manufacturing according to the disclosure.

[0076] The compound according to formula (I) obtained by the method of manufacturing according to the disclosure may, for example, be NaB(OCH3)4, NaB(OCF3)4, NaB(OCH2CH3)4, NaB(OCH2CF3)4, NaB(OCF2CF3)4, NaB(OCH2CH2CH3)4, NaB(OCH2CF2CF3)4, NaB(OCF2CF2CF3)4, NaB(OCH(CF3)2)4, NaB(OCH(CH3)2)4, NaB(OCH2CH2CH2CH3)4, NaB(OCH2CF2CF2CF3)4, NaB(OCH2CH(CH3)2)4, NaB(OC(CH3)3)4, NaB(OC(CF3)3)4, NaB(OPh)4, NaB(OPhF)4, NaB(OCH2CH2(CF2)mCF3)4 wherein m is 1 , 3, 5, 7 or 9.

[0077] Preferred compounds according to formula (I) obtained by the method of manufacturing according to the disclosure are NaB(OCH3)4, NaB(OCF3)4, NaB(OCH2CH3)4, NaB(OCH2CF3)4, NaB(OCF2CF3)4, NaB(OCH2CH2CH3)4, and NaB(OCH2CF2CF3)4.

[0078] Also disclosed herein is a compound according to formula (la), X-[B-(ORiO)2]n, each Ri is independently selected from the group consisting of C(2-4)alkylene, optionally substituted with one or more halogen, hydroxyl, C(1-4)alkyl, C(1-4)alkenyl, and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is 1 , X is a divalent cation and n is 2, or X is a trivalent cation and n is 3, characterized in that the compound according to formula (I) or the compound according to formula (la).

[0079] As discussed above, a particular advantage of compounds according to formula (I) obtained by the method of manufacturing according to the disclosure is that these compounds are substantially pure. Accordingly, the compound according to formula (I) obtained by the method of manufacturing according to the disclosure may have a purity of at least 99.5%, in particular at least 99.9%, more in particular at least 99.99% (e.g. as determined by elemental analysis (optionally using ASTM E1621-22) and / or a combination of elemental analysis with XRD analysis and / or NMR spectroscopic analysis). For example, the compound according to formula (1(a)) may contain less than 0.5% of trialkyl borate impurities, in particular at least 0.1 mol.% of trialkyl borate impurities, more in particular less than 0.01% of trialkyl borate impurities. As used herein, “C(x)alkyl” refers to an alkyl group having x carbon atoms in a linear or branched arrangement. For example, the term “C(6)alkyl” refers to a hexyl group.

[0080] As used herein, “C(x-y)alkylene” refers to an alkylene group having x to y carbon atoms in a linear or branched arrangement. For example, the term “C(2-4)alkylene” can refer to ethylene (-CH2CH2-), propylene (-CH2CH2CH2-) and butylene (-CH2CH2CH2CH2-) groups.

[0081] As used herein, “C(x-y)alkyl” refers to an alkyl group having x to y carbon atoms in a linear or branched arrangement. The alkyl group may be partially unsaturated. For example, the term “C(1-5)alkyl” refers to an alkyl having 1 to 5 carbon atoms, i.e. to methyl, ethyl, propyl, butyl, and pentyl groups.

[0082] As used herein, “C(x-y)aryl” refers to an aromatic group having x to y carbon atoms. For example, the term “C(6-10)aryl” may refer to a benzyl or naphthyl group. As another example, “C(6)aryl” refers to a benzyl group.

[0083] As used herein, “C(x-y)alkoxy” refers an alkyl group having x to y carbon atoms attached through an oxygen linking atom. For example, “C(1-3)alkoxy” refers to an alkyl group having one to three carbon atoms (i.e., methyl, ethyl, (iso-)propyl) attached through an oxygen linking atom, so to a methoxy, ethoxy or (iso-)propoxy group.

[0084] As used herein, “halogen” refers to Cl, Br, F, and I. It is preferred that “halogen” is F.

[0085] As used herein, “ionic boron-oxygen compound” refers to an ionic compound having at least one boron-oxygen bond. Examples of ionic boron-oxygen compounds include borax and hydrates thereof, as well as other boron-containing minerals mentioned herein. Boric acid is not an ionic boron-oxygen compound.

[0086] Examples

[0087] The following examples will illustrate the practice of the present disclosure in some of the preferred embodiments. Other embodiments within the scope of the claims will be apparent to one skilled in the art.

[0088] Example 1 : Synthesis of sodium tetra methoxy borate from anhydrous Borax (Na2B4O7)

[0089] In the following anhydrous borax (Na2B4O?) was allowed to react with methanol and sodium hydroxide according to the following reaction: Na2B4O7+ 2 NaOH + 24 MeOH 4 NaB(OMe)4+ 9 H2O

[0090] In a 200 mL round-bottom-flask (RBF) equipped with a reflux condenser anhydrous borax (2.00 g, 9.94 mmol, 1eq.) and sodium hydroxide (0.795 g, 19.9 mmol, 2 eq.) were dissolved in methanol (9.66 mL, 239 mmol, 24 eq.). 3 A Molecular sieves (13 g) were added to the mixture. The mixture was heated for 6 hours at reflux and the conversion was monitored via11B NMR spectroscopy. The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure to dryness, yielding sodium tetra methoxy borate in 68.0% yield.

[0091] The1H and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638-3653.

[0092] Example 2: Synthesis of sodium tetra ethoxy borate from anhydrous Borax (Na2B4O7) In the following anhydrous borax (Na2B4O?) was allowed to react with ethanol and sodium hydroxide according to the following reaction:

[0093] Na2B4O7+ 2 NaOH + 24 EtOH - ► 4 NaB(OEt)4+ 9 H2O

[0094] In a 200 mL round-bottom-flask (RBF) equipped with a reflux condenser anhydrous borax (2.00 g, 9.94 mmol, 1eq.) and sodium hydroxide (0.795 g, 19.9 mmol, 2 eq.) were dissolved in ethanol (13.9 mL, 239 mmol, 24 eq.). 3 A Molecular sieves (27 g) were added to the mixture. The mixture was heated for 24 hours at 120°C and the conversion was monitored via11B NMR spectroscopy.

[0095] The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure to dryness, yielding sodium tetra ethoxy borate in 74.0% yield. The1H and11B NMR spectroscopic of the reaction product confirmed the purity of the compound and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638-3653. Example 3: Synthesis of sodium tetra methoxy borate from Borax decahydrate (Na2B4O7x10H2O)

[0096] In the following borax decahydrate (Na2B4O?x10H2O) was allowed to react with methanol and sodium hydroxide according to the following reaction:

[0097] Na2B4O7x 10 H2O + 2 NaOH + 24 MeOH - ► 4 NaB(OMe)4+ 19 H2O

[0098] In a 200 mL round-bottom-flask (RBF) equipped with a reflux condenser borax decahydrate (10.00 g, 26.22 mmol, 1eq.) and sodium hydroxide (2.1 g, 52.44 mmol, 2 eq.) were dissolved in methanol (25.5 mL, 629 mmol, 24 eq.). 3 A Molecular sieves (20 g) were added to the mixture. The mixture was heated for 3 hours at 90°C and the conversion was monitored via11B NMR spectroscopy. After isolating the product via filtration of molecular sieves and solid residue11B NMR spectroscopy showed 70% yield. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638- 3653.

[0099] Example 4: Synthesis of sodium tetra ethoxy borate from Borax decahydrate (Na2B4O7x10H2O)

[0100] In the following borax decahydrate (Na2B4O7x10H2O) was allowed to react with ethanol and sodium hydroxide according to the following reaction:

[0101] Na2B4O7x 10 H2O + 2 NaOH + 24 EtOH - ► 4 NaB(OEt)4+ 19 H2O

[0102] In a 200 mL round-bottom-flask (RBF) equipped with a reflux condenser borax decahydrate (10.00 g, 26.22 mmol, 1eq.) and sodium hydroxide (2.1 g, 52.44 mmol, 2 eq.) were dissolved in ethanol (29.0 mL, 629 mmol, 24 eq.). 3 A Molecular sieves (45 g) were added to the mixture. The mixture was heated for 96 hours at 90°C and the conversion was monitored via11B NMR spectroscopy.

[0103] After isolating the product (50% yield), the1H and11B NMR spectroscopic data of the reaction product confirmed the purity of the compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638- 3653.

[0104] Example 5: Synthesis of sodium tetra methoxy borate from tincalconite (Na2B4O75 H2O) In the following tincalconite (Na2B4O?x 5 H2O) was allowed to react with methanol and sodium hydroxide according to the following reaction:

[0105] Na2B4O7X 5 H2O + 2 NaOH + 24 MeOH - ► 4 NaB(OMe)4+ 14 H2O

[0106] In a 10 0 mL Schlenk tube tincalconite (80 mg, 270 pmol, 1 eq.) and sodium hydroxide (22 mg, 550 pmol, 2 eq.) were dissolved in an excess methanol (2 mL, 629 mmol, 180 eq.) to ensure homogeneity of the solution. 3 A Molecular sieves (500 mg) were added to the mixture. The mixture was heated for 18 hours at 90°C. After isolating the product via filtration of molecular sieves and drying at high vacuum at 130 °C, 90% yield was determined.

[0107] Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638-3653.

[0108] Example 6: Synthesis of sodium tetra methoxy borate from kernite (Na2B4O74 H2O) In the following tincal (Na2B4O?x 4 H2O) was allowed to react with methanol and sodium hydroxide according to the following reaction:

[0109] Na2B4O7x 4 H2O + 2 NaOH + 24 MeOH - ► 4 NaB(OMe)4+ 13 H2O

[0110] In a 5 mL Schlenk tube kernite (75 mg, 270 pmol, 1 eq.) and sodium hydroxide (22 mg, 550 pmol, 2 eq.) were dissolved in an excess methanol (2 mL, 629 mmol, 180 eq.) to ensure homogeneity of the solution. 3 A Molecular sieves (500 mg) were added to the mixture. The mixture was heated for 18 hours at 90°C. After isolating the product via filtration of molecular sieves and drying at high vacuum at 130 °C, 48% yield was determined. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638-3653.

[0111] Example 7: Synthesis of sodium tetra butoxy borate from anhydrous borax (Na2B4O7) from a mixture butanol / acetonitrile (1 :1)

[0112] Na2B4O7+ 2 NaOH + 24 BuOH - ► 4 NaB(OBu)4+ 9 H2O

[0113] In a 200 mL round-bottom-flask (RBF) equipped with a reflux condenser anhydrous borax (5.00 g, 24.8 mmol, 1 eq.) and sodium hydroxide (1.99 g, 19.9 mmol, 2 eq.) were dissolved in a mixture of n-butanol (55 mL, 596 mmol, 24 eq.) and acetonitrile (55 mL). 3 A Molecular sieves (30 g) were added to the mixture. The mixture was heated for 18 hours at 110 °C. The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure while heating to 150 °C to ensure dryness, yielding sodium tetra n- butoxy borate in 60% yield.

[0114] The1H and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638-3653.

[0115] Example 8: Synthesis of sodium tetrakis(3,3,3-trifluoroethyl) borate from anhydrous borax (Na2B4O7)

[0116] Na2B4O7+ 2 NaOH + C2H2F3OH - ► 4 NaB(OC2H2F3)4+ 9 H2O

[0117] In a 5 mL Schlenk tube anhydrous borax (50 mg, 250 pmol, 1 eq.) and sodium hydroxide (20 mg, 500 pmol, 2 eq.) were dissolved in an excess of 2,2,2-trifluoroethanol (2.0 mL, 27.5 mmol, 110 eq.) to ensure homogeneity of the mixture. 3 A Molecular sieves (500 mg) were added to the mixture. The mixture was heated for 18 hours at reflux. The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure and heat to dryness, yielding sodium tetrakis(3,3,3-trifluoroethyl) borate in 24% yield.

[0118] The1H and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Chem. Eur. J. 2017, 23, 15628.

[0119] Example 9: Synthesis of sodium tetrakis(ethoxyethyl)borate from anhydrous borax (Na2B4O7)

[0120] Na2B4O7+ 2 NaOH + C4H10O2- ► 4 NaB(OC4H9O)4+ 9 H2O

[0121] In a 5 mL Schlenk tube anhydrous borax (50 mg, 250 pmol, 1 eq.) and sodium hydroxide (20 mg, 500 pmol, 2 eq.) were dissolved in an excess of 2-ethoxyethanol (2.0 mL, 20.6 mmol, 82.4 eq.) to ensure homogeneity of the mixture. 3 A Molecular sieves (500 mg) were added to the mixture. The mixture was heated for 18 hours at 130 °C. The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure and heat to dryness, yielding sodium tetrakis(ethoxyethyl) borate in 6% yield.

[0122] The identity and purity of the obtained compound were confirmed by spectroscopic and analytical methods, including nuclear magnetic resonance and infrared spectroscopy. The recorded spectra were consistent with the expected structure and composition of the target compound, thereby confirming its successful synthesis. No discrepancies or impurities were detected within the limits of analytical accuracy.

[0123] Example 10: Synthesis of sodium tetrakis(1,1,1,3,3,3-hexafluoroisopropyl) borate from anhydrous borax (Na2B4O7)

[0124] Na2B4O7+ 2 NaOH + C3HF6OH - ► 4 NaB(OC3HF6)4+ 9 H2O

[0125] In a 250 mL Schlenk round-bottom flask equipped with a reflux condenser anhydrous borax (2.50 g, 12.4 mmol, 1 eq.) and sodium hydroxide (994 mg, 24.8 mmol, 2 eq.) were dissolved in a mixture of 1 ,1,1,3,3,3-hexafluoroisopropanol (21 mL, 199 mmol, 16 eq.) and acetonitrile (21 mL) to ensure homogeneity of the mixture. 3 A Molecular sieves (30 g) were added to the mixture. The mixture was heated for 18 hours at reflux. The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure without external heating to dryness, yielding sodium tetrakis(1,1 ,1 ,3,3,3-hexafluoroisopropyl) borate in 36% yield.

[0126] The1H and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2011,40, 8114-8124 and Angew. Chem. Int. Ed. 2022, 61, e202202133.

[0127] Example 11 : Synthesis of sodium tetrakis(pentafluorophenyl) borate from anhydrous borax (Na2B4O7)

[0128] In a 25 mL Schlenk tube equipped with a stirring bar anhydrous borax (250 mg, 1.24 mmol, 1 eq.), sodium hydroxide (99.4 mg, 2.48 mmol, 2 eq.) and pentafluorophenol (2.74 g, 14.9 mmol, 12 eq.) were dissolved in acetonitrile (20 mL) to ensure homogeneity of the mixture. 3 A Molecular sieves (3 g) were added to the mixture. The mixture was heated for 18 hours at reflux. The molecular sieves and solid residue were filtered off and the residual mixture was evaporated under reduced pressure and heat to dryness, yielding sodium tetrakis(pentafluorophenyl) borate in 36% yield.

[0129] The1H and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Angew. Chem. Int. Ed. 2022, 61, e202202133.

[0130] Example 12: Synthesis of sodium bis(oxalato) borate from sodium tetra butoxy borate (NaB(OBu)4) in THF under an atmosphere of dry nitrogen

[0131] In the following sodium tetra butoxy borate (NaB(OBu)4) was formed by allowing borax to react with n-butanol and sodium hydroxide. The sodium tetra butoxy borate was then allowed to react with oxalic acid according to the following reaction:

[0132] In a 50 mL Schlenk flask sodium tetra butoxy borate (200 mg, 613 mmol, 1eq.), oxalic acid (110 mg, 1 .23 mmol, 2eq) and THF were added. The mixture was heated for 48 hours at reflux. The solvent was evaporated off under reduced pressure, yielding sodium bis(oxalato) borate at 81 ,5% yield.

[0133] The13C and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound, and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR spectroscopic literature values for comparison can be found inter alia in (Journal of Power Sources, 2014, Volume 248, Pages 77-82), and NMR spectroscopic literature values for comparison can be found inter alia in (Radiation Physics and Chemistry, 2009, Volume 78, Pages 1120-1125).

[0134] Example 13: Synthesis of sodium bis(oxalato) borate from sodium tetra butoxy borate (NaB(OBu)4) in acetonitrile under an atmosphere of dry nitrogen In the following sodium tetra butoxy borate (NaB(OBu)4) was formed by allowing borax to react with n-butanol and sodium hydroxide. The sodium tetra butoxy borate was then allowed to react with oxalic acid according to the following reaction:

[0135] NaB(OBu)4+ 2 C2O4H2- ► NaB(C2O4)2+ 4 BuOH

[0136] In a 50 mL Schlenk flask sodium tetra butoxy borate (200 mg, 613 mmol, 1eq.), oxalic acid (110 mg, 1 .23 mmol, 2eq) and acetonitrile were added. The mixture was stirred at room temperature for 2 hours. The solvent was evaporated off under reduced pressure, yielding sodium bis(oxalato) borate at 98,9% yield.

[0137] The13C and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the purity of the compound, and the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR spectroscopic literature values for comparison can be found inter alia in (Journal of Power Sources, 2014, Volume 248, Pages 77-82), and NMR spectroscopic literature values for comparison can be found inter alia in (Radiation Physics and Chemistry, 2009, Volume 78, Pages 1120-1125).

[0138] Comparative Example 1 : Synthesis of sodium tetra ethoxy borate from anhydrous borax (Na2B4O7) without molecular sieves

[0139] For comparative purposes (cf. Example 2), it was attempted to synthesize NaB(OEt)4via a method wherein no water was removed during the reacting.

[0140] Na2B4O7+ 2 NaOH + 24 EtOH - ► 4 NaB(OEt)4+ 9 H2O

[0141] In a 5 mL Schlenk tube equipped with a stirring bar anhydrous borax (50 mg, 250 pmol, 1 eq.) and sodium hydroxide (20 mg, 19.9 mmol, 2 eq.) were dissolved in an excess of ethanol (2 mL, 239 mmol, 140 eq.) to ensure homogeneity. The mixture was heated for 6 hours at reflux. Afterwards, the solvent was distilled off and the solids dried at 130 °C under high vacuum. The yield was measured corresponding to 10% of theoretical yield.

[0142] The1H and11B NMR spectroscopic data as well as the IR spectrum of the reaction product confirmed the spectra were identical compared to the spectra reported in literature for the same compound. Detailed IR and NMR spectroscopic literature values for comparison can be found inter alia in Dalton Trans., 2024, 53, 3638-3653. Comparative Example 2: Synthesis of sodium tetra ethoxy borate from anhydrous borax (Na2B4O7) with 2 equiv. of ethanol in acetonitrile

[0143] For comparative purposes, it was attempted to synthesize NaB(OEt)4 via a method using only 2 equivalents of ethanol per mole of boron in the borax and wherein no water was removed during the reacting.

[0144] Na2B4O7+ 2 NaOH + 8 EtOH - ► 2 NaB(OEt)4+ 5.5 H20

[0145] ACN

[0146] In a 5 mL Schlenk tube equipped with a stirring bar anhydrous borax (50 mg, 250 pmol, 1 eq.) and sodium hydroxide (20 mg, 19.9 mmol, 2 eq.) were dissolved in acetonitrile (2 mL) to ensure homogeneity and ethanol (29 L, 500 pmol, 2 eq.) added at once. The mixture was heated for 6 hours at reflux. Afterwards, the solvent was distilled off and the solids dried at 130 °C under high vacuum. No product could be identified from the residual solids.

Claims

We claim:

1. Method of manufacturing an organoboron salt, the method comprising reacting an ionic boron-oxygen compound, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax or a hydrate thereof, with a base and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C, wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1 -12)alkyl and C(6-10)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, and wherein X is a monovalent cation and n is1. X is a divalent cation and n is 2, or X is a trivalent cation and n is 3.

2. The method according to claim 1, wherein the ionic boron-oxygen compound is one or more selected from the group consisting of borax, kernite, tincalconite, and tincal.

3. The method according to claim 1 or 2, wherein the ionic boron-oxygen compound and the base comprise a cation X, wherein the cation X of the ionic boron-oxygen compound, the cation X of the base, and the cation X of the compound according to formula (I) are the same.

4. The method according any one of claims 1 to 3, wherein the base is NaOH, Na2CO3, NaHCCh, or Na2O.

5. The method according to any one of claims 1 to 4, wherein the reacting comprises contacting the ionic boron-oxygen compound with the base to form an intermediate, followed by contacting the intermediate with the compound according to formula (II); or the reacting comprises contacting the compound according to formula (II) with the base to form an intermediate, followed by contacting the ionic boron-oxygen compound with the intermediate.

6. The method according to any one of claims 1 to 5, wherein the reacting comprises simultaneously contacting the ionic boron-oxygen compound with the base and the compound according to formula (II).

7. The method according to any one of claims 1 to 6, wherein the reacting comprises using the one or more compounds according to formula (II) in a total amount of from 4.0 to 10 moles of compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, in particular a total amount of from 4.0 to 7.0 moles of compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, more in particular 4.0 to 4.3 moles of compound according to formula (II) per mole of boron in the ionic boron-oxygen compound.

8. The method according to any one of claims 1 to 7, wherein the reacting comprises using 1.0 to 12.0 moles of base per mole of cation in the ionic boron-oxygen compound, in particular 1.0 to 5.0 moles of base per mole of cation in the ionic boron-oxygen compound.

9. The method according to any one of claims 1 to 8, wherein the method comprises reacting an ionic boron-oxygen compound selected from the group consisting of borax and hydrates thereof (in particular borax, kernite, tincalconite, and tincal) with a base selected from the group consisting of NaOH, Na2COs, NaHCCh, and Na2O (in particular, NaOH) and one or more compounds according to formula (II), R-OH, wherein R is selected from the group consisting of C(1 - 12)alkyl (in particular C(2-10)alkyl, more in particular C(3- 8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, in a total amount of at least 4.0 moles of the compound according to formula (II) per mole of boron in the ionic boron-oxygen compound, at a temperature of at least 20 °C (in particular at a temperature of from 50 to 90 °C), wherein water is removed during the reacting, thereby forming the organoboron salt, wherein the organoboron salt is a compound according to formula (I), X-[B-(OR)4]n, wherein each R is independently selected from the group consisting of C(1-12)alkyl (in particular C(2-10)alkyl, more in particular C(3-8)alkyl) and C(6)aryl, each optionally substituted with one or more halogen, hydroxyl and / or C(1-4)alkoxy, X is Na, and n is 1.

10. The method according to any one of claims 1 to 9, wherein water is removed during the reaction using a solid, water-absorbing material, in particular using molecular sieves, alumina, sodium sulfate, magnesium sulfate, or boron trioxide.

11. The method according to any one of claims 1 to 10, wherein the reacting comprises using stoichiometric amounts of the ionic boron-oxygen compound, the compound according to formula (II), and the base.

12. The method according to any one of claims 1 to 11 , wherein the method further comprises the step of isolating the compound according to formula (I).

13. Method of processing an organoboron salt, wherein the method comprises the steps of manufacturing an organoboron salt, wherein the organoboron salt is a compound according to formula (I), according to the method of any one of claims 1 to 12, reacting the organoboron salt with a further reagent.

14. The method according to claim 13, wherein the further reagent is selected from the group consisting of a cation source, hydride source, water, alcohols, diols, dicarboxylic acids and their salts, in particular wherein the further reagent is a hydride source or a cation source, optionally wherein the cation source is a salt having a cation selected from alkali metals (in particular, Li, Na, K, and Cs), alkaline earth metals (in particular, Mg and Ca), Zn, NH4, N[C(1 -4)alkyl]4, P[C(1-14)alkyl]4, imidazolium, pyrrolidinium, and piperidinium.

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