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(oxalato)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

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.
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.
PubChem. "Lithium difluoro(oxalato)borate". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-07-19.
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.
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.
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.
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.
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.
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.
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.
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.
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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[bess-1] 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.

[:1-2] 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.

[:0-4] 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.

[:2-7] 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.