Copper benzoate

Copper benzoate
Names
IUPAC name
copper dibenzoate
Other names
cupric benzoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.776
UNII
  • InChI=1S/2C7H6O2.Cu/c2*8-7(9)6-4-2-1-3-5-6;/h2*1-5H,(H,8,9);/q;;+2/p-2 Y
    Key: YEOCHZFPBYUXMC-UHFFFAOYSA-L Y
  • InChI=1/2C7H6O2.Cu/c2*8-7(9)6-4-2-1-3-5-6;/h2*1-5H,(H,8,9);/q;;+2/p-2
    Key: YEOCHZFPBYUXMC-NUQVWONBAX
  • [Cu+2].[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1
  • Chinese lantern structure: c0ccccc0[C-](O[Cu+2]123)O[Cu+2](O[C-](O1)c0ccccc0)(O[C-](O2)c0ccccc0)O[C-](O3)c0ccccc0
Properties
  • C14H10CuO4[1]
  • C14H12CuO5 (dihydrate)[2]
Molar mass
  • 305.77 g/mol[1]
  • 323.795 g/mol (dihydrate)[2]
Appearance blue solid
Density 1.197 g/cm3
Hazards
GHS labelling:[1]
Warning
H315, H319, H335
P261, P305+P351+P338
Flash point 111.4 °C (232.5 °F; 384.5 K)
NIOSH (US health exposure limits):[3]
PEL (Permissible)
 TWA 1 mg/m3 (as Cu)
REL (Recommended)
 TWA 1 mg/m3 (as Cu)
IDLH (Immediate danger)
 TWA 100 mg/m3 (as Cu)
Related compounds
Other anions
Other cations
Related compounds
 Phenylcopper
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Copper benzoate describes chemical compound with the formula Cu(C6H5CO2)2(H2O)n. They consist of coordination complexes derived from the cupric ion and the conjugate base of benzoic acid. Many derivatives are known with diverse ancillary ligands.[4]

Structure

Copper(II) benzoate exists in at least two structural forms, depending on the degree of hydration. Resembling copper(II) acetate, one form of copper benzoate adopts a "Chinese lantern" structure,[5] wherein a pair of copper centers are linked by four bridging carboxylate ligands. Typically, one site on each copper center is occupied by water, which can be replaced by other ligands.[6] A hydrated form is also known, wherein each Cu(II) centre is bound to four water ligands and a bidentate O, O-benzoate.[7]

Preparation

Trihydrate

Copper benzoate trihydrate can be made by combining aqueous solutions of sodium benzoate and copper sulfate, forming a pale blue precipitate:[8]

4 K(C6H5CO2) + 2 CuSO4·5H2O → Cu2(C6H5CO2)4(H2O)2 + 2 K2SO4 + 8 H2O

Anhydrous forms

The "α form" of the anhydrous compound is prepared by vacuum desiccation of the trihydrate at 95 °C with phosphorus pentoxide.[8] The "β form" is obtained by heating the monoethanol derivative in air at 90 °C.[8] The "γ form" is obtained by heating the monoethanol derivative in boiling carbon tetrachloride for a few hours.[8] All are described as "blue-green crystalline powders."

Uses

It has found some niche use as a combination fuel and source of copper ion for blue light production in fireworks.[9] It is not on the list of chemicals approved in consumer fireworks in the US.[10]

It is also used in two-part dental adhesives, in polyester resin compositions to increase thermal resistance and decrease gelation, and as a metal-based hydrogen sulfide scavenger in asphalt.[1]

Tetrakis[copper(I) benzoate]

A tetrakis[copper(I) benzoate] has been characterized.[11][12]

Addition compounds

Copper(II) benzoate forms many addition compounds. Examples include copper(II) benzoate mono(benzoic acid) and the adducts with ethanol and urea.[8]

References

  1. ^ a b c d "Copper Benzoate SDS" (PDF). JPharmaChem. Dr. J. Pharmachem Pvt. Ltd. Retrieved 12 July 2025.
  2. ^ a b Sigma-Aldrich Co., Benzoic acid, copper (II) salt dihydrate.
  3. ^ "NIOSH Pocket Guide to Chemical Hazards".
  4. ^ Rajakannu, Palanisamy; Kaleeswaran, Dhananjayan; Banerjee, Subarna; Butcher, Ray J.; Murugavel, Ramaswamy (2019-02-24). "Effect of benzoic acid substituents and additional functional groups of ancillary ligands in modulating the nuclearity and aggregation behavior of transition metal carboxylates". Inorganica Chimica Acta. 486: 283–293. doi:10.1016/j.ica.2018.10.054. ISSN 0020-1693.
  5. ^ Wells, A. F. (1984). Structural inorganic chemistry (5th ed.). Oxford [Oxfordshire] : New York: Clarendon Press; Oxford University Press. p. 1131. ISBN 0-19-855370-6.
  6. ^ Kawata, T.; Uekusa, H.; Ohba, S.; Furukawa, T.; Tokii, T.; Muto, Y.; Kato, M. (1 June 1992). "Magneto-structural correlation in dimeric copper(II) benzoates". Acta Crystallographica Section B Structural Science. 48 (3): 253–261. doi:10.1107/S0108768191012697.
  7. ^ Koizumi, Hideo; Osaki, Kenji; Watanabé, Tokunosuké (1963). "Crystal Structure of Cupric Benzoate Trihydrate Cu(C6H5COO)23H2O". Journal of the Physical Society of Japan. 18 (1): 117–124. Bibcode:1963JPSJ...18..117K. doi:10.1143/JPSJ.18.117.
  8. ^ a b c d e Inoue, Motomichi; Kishita, Michihiko; Kubo, Masaji (1964-02-01). "Magnetic Moments of Copper(II) Salicylate, Copper(II) Benzoate, and Some Related Compounds". Inorganic Chemistry. 3 (2): 239–242. doi:10.1021/ic50012a022. ISSN 0020-1669.
  9. ^ "Formulas For Firework Stars Using Copper Benzoate". Skylighter, Inc. Retrieved 2025-05-27.
  10. ^ "Approved and Prohibited Fireworks Chemicals" (PDF). www.phmsa.dot.gov. US Department of Transportation. Retrieved 12 July 2025.
  11. ^ Drew, Michael G. B.; Edwards, Dennis A.; Richards, Roger (1977-01-01). "Crystal and molecular structure of tetrakis[copper(I) benzoate]". Journal of the Chemical Society, Dalton Transactions (3): 299–303. doi:10.1039/DT9770000299. ISSN 1364-5447.
  12. ^ Edwards, Dennis A.; Richards, Roger (1973-01-01). "Copper(I) carboxylates: preparations and infrared and mass spectral features". Journal of the Chemical Society, Dalton Transactions (22): 2465. doi:10.1039/DT9730002463. ISSN 1364-5447.
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