Oxalatoborates

Boro-oxalates, bis(oxalato)borates, or oxalatoborates are chemical compounds where an oxalate group is bound to a borate group via oxygen, forming a condensed anion. The oxalatoborates are heterocyclic compounds with a ring containing -O-B-O-C-C-. Bis(oxalato)borates are spiro compounds with two rings joined at the boron atom.

Oxalatoborates are used for research in lithium-ion battery electrolytes and for supercapacitors.

The borate oxalates are chemical compounds containing separate borate and oxalate anions. Compared to oxalatoborates, these are of little importance.

Production

Oxalatoborates have been produced by heating boric acid, oxalic acid and a metal oxalate, a metal carbonate or an amine in boiling benzene with continuous removal of water via azeotropic distillation.[1]

Properties

When heated, oxalatoborates decompose at around 320 °C to yield a metaborate, carbon monoxide, and carbon dioxide.[1]

List

Name Chemical formula Molecular weight Crystal system Space group Unit cell (Å) Volume Density Comments References
Lithium bis(oxalate)borate, LiBOB LiB(C2O4)2 193.8 orthorhombic Pnma a 6.3635 b 7.5998 c 13.1715 [2]
lithium difluoro (oxalate) borate, LiDFOB LiBF2(C2O4) 143.8 orthorhombic Cmcm a = 6.2623, b = 11.437, c = 6.3002, Z = 4 451.22 [3][4]
lithium difluoro (oxalate) borate dihydrate LiBF2(C2O4)•2H2O monoclinic P21/c a = 9.5580, b = 12.7162, c = 5.4387, β =106.247 Z = 4 634.63 [4]
ammonium bis(oxalato)borate [1]
tetramethylammonium bis(oxalato)borate N(CH3)4B(C2O4)2 [5]
triethylammonium bis(oxalato)borate [1]
pyridinium bis(oxalato)borate [1]
quinolinium bis(oxalato)borate [1]
1-ethyl-3-methylimidazolium bis(oxalate)borate (EmimBOB) ionic liquid [6]
1-Butyl-1-Methylpyrrolidinium bis(oxalate)borate; Bmpyr BOB (C4H8N+)(CH3)(C4H10)[B(C2O4)2]− ionic liquid
[(C2H5)4N][CF3B(OCH3)(C2O4)] [7]
[(C2H5)4N][CF3CF2B(OCH3)(C2O4)] [7]
[(C2H5)4N][CF3BF(C2O4)] [7]
[(C2H5)4N][CF3CF2BF(C2O4)] [7]
sodium bis(oxalato)borate, NaBOB NaB(C2O4)2 orthorhombic Cmcm a 8.12756( b 10.3399 c 7.8211 [8][2]
Trihexyltetradecylphosphonium bis(oxalate)borate [9]
[(C6H5)4P][CF3B(OCH3)(C2O4)] 538.24 triclinic P1 a 11.0744 b 11.5314 c 12.2196, α 73.427° β 69.395° γ 61.786° Z=2 1273.7 1.403 [7]
[(C6H5)4P][CF3CF2B(OCH3)(C2O4)] [7]
[(C6H5)4P][CF3BF(C2O4)] [7]
[(C6H5)4P][CF3CF2BF(C2O4)] 576.22 monoclinic C2/c a 16.821 b 7.1612 c 21.519 β 101.981° Z=4 2535.6 1.509 [7]
Lithium difluoro(oxalato)borate tetramethylene sulfone disolvate Li+•C2BF2O4−•2C4H8O2S monoclinic P21/n a = 13.9005 b = 5.8917 c = 19.9627 β = 106.010 Z=4 1571.48 1.623 colourless [10]
rubidium bis(oxalato)borate [1]
caesium bis(oxalato)borate [1]
thallium bis(oxalato)borate [1]
Borate oxalates
potassium boro-oxalate K(C2O4)(BO2)2•2H2O 248.77 triclinic P1 a=6.3508 b=7.0095 c=10.590 α=93.798 β=101.424 γ=100.196 452.3 1.827 NLO 1.56×KDP; stable to 187 °C [11]
Pb6O2(BO3)2(C2O4) 740.39 orthorhombic Cmcm a=18.0445 b=6.6225 c=11.4682 Z=8 1370.45 7.177 band gap 3.60 eV [12]

References

  1. ^ a b c d e f g h i Bessler, Eberhard; Weidlein, Johann (1 August 1982). "Borkomplexe mit Dicarbonsäuren: Bis(oxalato)borate und Bis(malonato)borate" [Boron Complexes with Dicarboxylic Acids: Bis(oxalato)borates and Bis(malonato)borates]. Zeitschrift für Naturforschung B. 37 (8): 1020–1025. doi:10.1515/znb-1982-0813. S2CID 53546940.
  2. ^ a b Zavalij, Peter Y.; Yang, Shoufeng; Whittingham, M. Stanley (2003-12-01). "Structures of potassium, sodium and lithium bis(oxalato)borate salts from powder diffraction data". Acta Crystallographica Section B. 59 (6): 753–759. doi:10.1107/S0108768103022602. ISSN 0108-7681. PMID 14634252.
  3. ^ PubChem. "Lithium difluoro(oxalato)borate". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-07-19.
  4. ^ a b Allen, Joshua L.; Han, Sang-Don; Boyle, Paul D.; Henderson, Wesley A. (November 2011). "Crystal structure and physical properties of lithium difluoro(oxalato)borate (LiDFOB or LiBF2Ox)". Journal of Power Sources. 196 (22): 9737–9742. Bibcode:2011JPS...196.9737A. doi:10.1016/j.jpowsour.2011.07.065.
  5. ^ Globa, N. I.; Pushyk, O. B.; Gromadskyi, D. G.; Milovanova, O. I.; Kirillov, S. A. (June 2016). "Electrochemical behavior of activated carbon electrodes in electric double layer capacitors with tetrametylammonium bis(oxalato)borate electrolyte synthesized by microwave irradiation". Russian Journal of Applied Chemistry. 89 (6): 1000–1008. doi:10.1134/S1070427216060252. ISSN 1070-4272. S2CID 100297708.
  6. ^ Wang, Liang; Zhang, Hong; Ge, Rile; Wang, Chaolei; Guo, Wei; Shi, Yantao; Gao, Yanan; Ma, Tingli (2013). "First application of bis(oxalate)borate ionic liquids (ILBOBs) in high-performance dye-sensitized solar cells". RSC Advances. 3 (31): 12975. Bibcode:2013RSCAd...312975W. doi:10.1039/c3ra41180j. ISSN 2046-2069.
  7. ^ a b c d e f g h Sprenger, Jan A.P.; Schäfer, Marius; Ignatiev, Nikolai; Finze, Maik (June 2015). "Salts of novel chelatoborate anions: [R F BX(ox)] − (R F = CF3, C2F5; X = F, OMe; ox = oxalato) and [R F B(OMe)(cat)] − (R F = CF3, C2F5; cat = catecholato)". Journal of Fluorine Chemistry. 174: 30–35. doi:10.1016/j.jfluchem.2014.08.003.
  8. ^ Mogensen, Ronnie; Buckel, Alexander; Colbin, Simon; Younesi, Reza (2021-02-23). "A Wide-Temperature-Range, Low-Cost, Fluorine-Free Battery Electrolyte Based On Sodium Bis(Oxalate)Borate". Chemistry of Materials. 33 (4): 1130–1139. doi:10.1021/acs.chemmater.0c03570. ISSN 0897-4756. S2CID 233994118.
  9. ^ Hjalmarsson, Nicklas; Alvarez-Asencio, Ruben (2013). "Biodegradable ionic liquids as lubricants" (PDF). 5th World Tribology Congress. Archived (PDF) from the original on 2021-07-19.
  10. ^ Allen, Joshua L.; Boyle, Paul D.; Henderson, Wesley A. (2011-05-15). "Lithium difluoro(oxalato)borate tetramethylene sulfone disolvate". Acta Crystallographica Section E. 67 (5): m533. doi:10.1107/S1600536811011743. ISSN 1600-5368. PMC 3089187. PMID 21754273.
  11. ^ Devi, S.; Jananakumar, Deepa (December 2020). "Structural, optical, spectroscopic and thermal investigations on novel semi-organic nonlinear optical material - Potassium boro-oxalate single crystal". Chinese Journal of Physics. 68: 339–347. Bibcode:2020ChJPh..68..339D. doi:10.1016/j.cjph.2020.09.018. S2CID 225332548.
  12. ^ Yang, Hui; Mao, Feifei; Xu, Cuixia (2018-05-24). "Syntheses, Crystal Structures and Properties of Two Novel Mixed Anion Hybrids with Formulas of Pb6O2(BO3)2(C2O4) and Pb4(CO3)2(C2O4)(OH)2". ChemistrySelect. 3 (19): 5431–5438. doi:10.1002/slct.201801072. ISSN 2365-6549.
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