Guanidinium carbonate

Guanidinium carbonate
Names
Other names
  • Bisguanidinium carbonate
  • Diguanidinium carbonate
  • Guanidine carbonate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.923
EC Number
  • 209-813-7
UNII
  • InChI=1S/2CH5N3.CH2O3/c3*2-1(3)4/h2*(H5,2,3,4);(H2,2,3,4)
    Key: STIAPHVBRDNOAJ-UHFFFAOYSA-N
  • C(=N)(N)N.C(=N)(N)N.C(=O)(O)O
Properties
C3H12N6O3
Molar mass 180.168 g·mol−1
Appearance White solid
Density 1.24 g/cm3[1]
Melting point 250 °C (482 °F; 523 K)[2] (decomposes)
Structure[1]
tetragonal
P41212 (No. 92)
a = 6.982 Å, c = 19.635 Å
4 units per cell
Hazards
GHS labelling:[3]
Danger
H302, H315, H318, H319, H335, H412
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Guanidinium carbonate or guanidine carbonate is the carbonate salt of guanidine with the chemical formula [C(NH2)3]2CO3. It is a white solid, forming tetragonal crystals exhibiting non-linear optical properties.[1][2]

Uses

Cosmetics

It has been used in cosmetic products for permanent hair straightening.[4] The active ingredient, guanidine hydroxide, is formed in situ by the reaction of guanidine carbonate with calcium hydroxide.[4] This formulation causes less irritation to the scalp than products directly containing a strong base such as sodium hydroxide.[4]

Materials

It is used in polyacrylonitrile (PAN)-based carbon fibers as an accelerator base material, improving the rate of fiber stabilization, fiber density, and tensile strength.[5]

It is used in the preparation of graphitic carbon nitride (g-C3N4) where it acts as an assembly edge terminator, binding to the composite surface to alter its morphology and expose active sites.[6] The synthesis involves a thermal polycondensation method in which melamine, cyanuric acid, and guanidine carbonate are assembled.[7]

Organic synthesis

Guanidine carbonate derivates are used in the synthesis of 5,5-diphenyl-2-iminohydantoins.[8] The reaction proceeds by the condensation of benzil with guanidine carbonate in ethanolic KOH.[8]

Reactions

Hydrolysis occurs upon heating in aqueous solution, forming urea and ammonium carbonate:[9]

[C(NH2)3]2CO3 + 2 H2O → 2 CO(NH2)2 + (NH4)2CO3

Guanidine carbonate reacts with ammonium dinitramide to form the energetic material guanidinium dinitramide:[10]

2 NH4N(NO2)2 + (NH2C(NH2)NH2)2CO3 → 2 NH2C(NH2)NH2N(NO2)2 + (NH4)2CO3

It reacts with boric acid to form anhydrous guanidinium tetraborate in a solid-state reaction at 115 °C.[11]

It also forms hydrogen bonded complexes with cyanuric acid.[12]

A guanidinium bicarbonate (C(NH2)3HCO3) has been characterized.[13]

References

  1. ^ a b c Adams, J. M.; Small, R. W. H. (1974-09-15). "The crystal structure of guanidinium carbonate". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 30 (9): 2191–2193. doi:10.1107/S0567740874006716. ISSN 0567-7408.
  2. ^ a b Deepa, B.; Philominathan, P. (2016-02-01). "Optical, mechanical and thermal behaviour of Guanidinium Carbonate single crystal". Optik. 127 (3): 1507–1510. doi:10.1016/j.ijleo.2015.10.159. ISSN 0030-4026.
  3. ^ PubChem. "Guanidine carbonate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-13.
  4. ^ a b c De Sá Dias, Tania Cristina; Baby, André Rolim; Kaneko, Telma Mary; Robles Velasco, Maria Valéria (March 2007). "Relaxing/straightening of Afro-ethnic hair: historical overview". Journal of Cosmetic Dermatology. 6 (1): 2–5. doi:10.1111/j.1473-2165.2007.00294.x. ISSN 1473-2130. PMID 17348987.
  5. ^ Yusof, N.; Ismail, A. F. (2012-01-01). "Post spinning and pyrolysis processes of polyacrylonitrile (PAN)-based carbon fiber and activated carbon fiber: A review". Journal of Analytical and Applied Pyrolysis. 93: 3. doi:10.1016/j.jaap.2011.10.001. ISSN 0165-2370.
  6. ^ Qian, Xinru; Li, Wenjin; Wang, Xiaoning; Guan, Haibin; Bao, Qinghe; Zhao, Baofeng; Wulan, Bari; Liu, Suxiang; Zhu, Di; Feng, Xiangyu; Sun, Jian (March 2025). "Multifunctional Roles of Ionic Microenvironments in the Preparation, Modification, and Application of g-C 3 N 4". Advanced Functional Materials. 35 (11) 2416946. doi:10.1002/adfm.202416946. ISSN 1616-301X.
  7. ^ Husein, Saddam; Slamet; Dewi, Eniya Listiani (2024-12-01). "A review on graphite carbon nitride (g-C3N4)-based composite for antibiotics and dye degradation and hydrogen production". Waste Disposal & Sustainable Energy. 6 (4): 603–635. doi:10.1007/s42768-024-00198-y. ISSN 2524-7891.
  8. ^ a b Kaur, Navjeet; Rajput, Mansi; Bhardwaj, Pranshu (2022-08-03). "Synthesis of heterocycles using guanidine: An overview". Synthetic Communications. 52 (15): 1549. doi:10.1080/00397911.2022.2087045. ISSN 0039-7911.
  9. ^ Bell, James (1928-01-01). "CCLXXI.—The hydrolysis of guanidine carbonate". Journal of the Chemical Society (Resumed): 2074–2077. doi:10.1039/JR9280002074. ISSN 0368-1769.
  10. ^ Kim, Wooram; Park, Mijung; Park, Yeonsoo; Kwon, Younja; Jo, Youngmin (2018-12-25). "Synthesis and characterization of a new energy material (guanidinium dinitramide) with crystallization solvent". Journal of Industrial and Engineering Chemistry. 68: 153–160. doi:10.1016/j.jiec.2018.07.040. ISSN 1226-086X.
  11. ^ Fuwa, Ryunosuke; Tsuyumoto, Isao (2023-09-01). "Guanidinium tetraborate anhydrate and its solid-state reaction synthesis". Results in Materials. 19 100436. doi:10.1016/j.rinma.2023.100436. ISSN 2590-048X.
  12. ^ Sivashankar, K. (2000-12-01). "Hydrogen bonded complexes of cyanuric acid with pyridine and guanidinium carbonate". Journal of Chemical Sciences. 112 (6): 607–614. doi:10.1007/BF02704368. ISSN 0973-7103.
  13. ^ Baldwin, D. A.; Denner, L.; Egan, T. J.; Markwell, A. J. (1986-09-15). "Structure of guanidinium bicarbonate: a model for the bicarbonate anion binding site of the transferrins". Acta Crystallographica Section C: Crystal Structure Communications. 42 (9): 1197–1199. doi:10.1107/S0108270186092909. ISSN 0108-2701.
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