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Borate oxalate

The borate oxalates are chemical compounds containing borate and oxalate anions. Where the oxalate group is bound to the borate via oxygen, a more condensed anion is formed that balances less cations. These can be termed boro-oxalates, bis(oxalato)borates, or oxalatoborates or oxalate borates. The oxalatoborates are heterocyclic compounds with a ring containing -O-B-O-. Bis(oxalato)borates are spiro compounds with rings joined at the boron atom.

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

Production

Oxalatoborates have been produced by heating boric acid, oxalic acid and one of a metal oxalate, a metal carbonate or an amine in boiling benzene.[1]

Properties

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

List

name chemical formula mw crystal system space group unit cell Å volume density comment CAS

no

references
Lithium bis(oxalate)borate, LiBOB LiB(C2O4)2 193.8 orthorhombic Pnma a 6.3635 b 7.5998 c 13.1715 244761-29-3 [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 409071-16-5 [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]
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×KDP; stable to 187 °C [11]
rubidium bis(oxalato)borate [1]
caesium bis(oxalato)borate [1]
thallium bis(oxalato)borate [1]
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 = CF 3 , C 2 F 5 ; X = F, OMe; ox = oxalato) and [R F B(OMe)(cat)] − (R F = CF 3 , C 2 F 5 ; 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 Pb 6 O 2 (BO 3 ) 2 (C 2 O 4 ) and Pb 4 (CO 3 ) 2 (C 2 O 4 )(OH) 2". ChemistrySelect. 3 (19): 5431–5438. doi:10.1002/slct.201801072. ISSN 2365-6549.
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