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Embed Size px x x x x Since its invention the Simons process is one of thefavoured processes in the production of highly uorinatedmaterials[4]. Ethyl triate can be easily separated from the reaction mixturevia distillation, and the remaining ethyl benzoate is also a valuableproduct. Alkyl triates can also be used in solvent free metathesisreactions to eliminate chloride or bromide and synthesize highlyunsymmetrical triates ionic liquids with low halide content [8,9]. Scheme 3 presents an example:. Triic acid is widely used as catalyst andstarting material for the production of triates, for instance alkyltriates, CF3SO2OR.

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Embed Size px x x x x Since its invention the Simons process is one of thefavoured processes in the production of highly uorinatedmaterials[4]. Ethyl triate can be easily separated from the reaction mixturevia distillation, and the remaining ethyl benzoate is also a valuableproduct. Alkyl triates can also be used in solvent free metathesisreactions to eliminate chloride or bromide and synthesize highlyunsymmetrical triates ionic liquids with low halide content [8,9].

Scheme 3 presents an example:. Triic acid is widely used as catalyst andstarting material for the production of triates, for instance alkyltriates, CF3SO2OR.

Methyl and ethyl triate provide convenientaccess to ionic liquids ILs with triate anion via direct alkylation ofamines, phosphines or heterocyclic compounds.

These very strongalkylating reagents canbe easily prepared vianewmethods recentlydeveloped by Merck KGaA [6,7] Scheme 1 and 2. Method A see Scheme 1 [6] provides a very convenientaccess to methyl triate, which is produced in a very good yieldwith CO2 as the only side product. The disadvantage in thismethodis the use of relatively expensive starting material: triic acidanhydride. The production costs can be substantially reduced iftriic acid is used in combination with acyl or aryl chlorides, for.

Alkyl and aryl sulfonates, alkyl sulfates and alkyl phosphates. Anhydrides or silyl esters of triic acid and triuoroacetic acidor silyl ester of bis peruoroalkyl phosphinic acid can be used inthis type of reactions instead of alkyl triates, alkylphosphinates oralkyl triuoroacetates Scheme 6 []. The products ILs areformed in quantitative or near to quantitative yield.

Oxonium and sulfonium salts are also active in suchmetathesisreactions Scheme 7 forming the products in quantitative yield[12,13]:. The above described methodology offers the possibility tosynthesize highly unsymmetrical ionic liquids with low content ofhalide.

According to these methods the structures of cation andanion in ionic liquid can be built up independently. All rights reserved. Ignatev et al. ILs based upon chloride or bromide anions are very viscousliquids or even solid material at room temperature.

Ionic liquidsbased upon tetrauoroborate BF4. In particular, hexauorophosphates are water sensitive. Trying both to decrease the viscosity and increase the hydrolyticstability, we have developed new ILs with tris peruoroalkyl tri-uorophosphate [ RF 3PF3]. Schuoroalkyl diuorophosphoranes, RF 3PF2 [15,16] in a good yield. Tris peruoroalkyl diuorophosphoranes are very reactive com-pounds and can be easily converted into several derivatives whichare attractive for practical applications Scheme 8.

SchemeTris peruoroalkyl diuorophosphoranes are strong Lewisacids which are able to abstract uoride anion from BF4. We have used this reaction also to preparelithium tris pentauoroethyl triuorophosphate, Li[ C2F5 3PF3] LiFAP [19,20], that can be easily obtained via interaction oftris pentauoroethyl diuorophosphorane with LiF in polarorganic solvents or organic solvent mixtures Scheme Tris peruoroalkyl diuorophosphoranes are moisture sensi-. Schemegenerated in this reaction.

FAP-based ILs possess high hydrolytic, thermal and electro-chemical stability [22]. RF 3P55O give access to a new method for the alkylation oforganic bases with alcohols resulting in quaternary salts with thebis peruoroalkyl phosphinate anion Scheme 14 [29]. This newreaction class results in the formation of hydrophilic watersoluble ILs in good yield and the only side product in this processis C2F5H F which can be utilised for practical use.

This processopens the door to the alkylation of organic compounds withalcohols cheap and in many cases non-toxic source of alkylgroups Scheme Post on Jun views. Category: Documents 1 download.

Scheme 3 presents an example: Alkyl bis peruoroalkyl phosphinates are slightly less reactive Journal of Fluorine Chemistry Peruoroalkyl-uorophosphate Ionic liquids Conducting salts Brnsted acids ion pho oro pha hyd orga the s, etc. Contents lists available at ScienceDirect Journal of Fluor. The production costs can be substantially reduced iftriic acid is used in combination with acyl or aryl chlorides, for than alkyl triates in this reaction Scheme 4 [9,10].

Alkyl and aryl sulfonates, alkyl sulfates and alkyl phosphates can react with organic halides in the same way Scheme 5 resulting in the formation of corresponding ionic liquids inquantitative or near to quantitative yield [].

Oxonium and sulfonium salts are also active in suchmetathesisreactions Scheme 7 forming the products in quantitative yield[12,13]: The above described methodology offers the possibility tosynthesize highly unsymmetrical ionic liquids with low content ofhalide. E-mail address: nikolai. Willner b, P. Organic and in conductivity that makes batteries, super-capacitor journa l homepage: wwwcess A powerful tool for thec liquids and strong Brnsted acids stadt, Germany ermany , Duisburg, Germany Simons process provides a cheap commercial access to a series of sphoranes.

These substances are convenient starting material for the -chemicals. The synthesis of new conducting salts and ionic liquids with te FAP and peruoroalkyl-phosphinate anions is described. FAP ionic rolytic stability, low viscosity and high electrochemical and thermal nic salts with FAP anions possess high electrochemical stability and m attractive for application in several electrochemical devices Li-ion ine Chemistry l sev ier.

Scheme 2. Scheme 3. Ionic liquidsbased upon tetrauoroborate BF4 and hexauorophosphate PF6 anions are less viscous, but they are not very hydrolytically stable[14]. The key for these ILs is the electrochemical uorination of trialkylphosphines, R3P, that results in the formation of tris per- Schuoroalkyl diuorophosphoranes, RF 3PF2 [15,16] in a good yield.

SchemeTris peruoroalkyl diuorophosphoranes are strong Lewisacids which are able to abstract uoride anion from BF4 orPF6 anions, for example see Scheme 9 [13]:The high uoride afnity of uoroalkyl-uorophosphoranes is known from the literature [17]. LiFAP is of interest for application in Li-ion batteries as new 4.

Tris peruoroalkyl diuorophosphoranes are moisture sensi- tive compounds, but the uoride afnity of these substances is sohigh that in contact with aqueous HF the hydrolysis is negligible; 5. Treatment of bis peruoroalkyl phosphinates or peruoroalk- ylphosphonates with aHF leads to the formation of thecorresponding bis peruoroalkyl -tetrauorophosphates or per-uoroalkyl-pentauorophosphates Scheme 15 [21].

Scheme 9. Scheme

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