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Draft:Urea hydrochloride

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Urea hydrochloride
Names
Other names
  • Urea monohydrochloride
  • Carbamide chloride
  • Uronium chloride
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 208-059-6
UNII
  • InChI=1S/CH4N2O.ClH/c2-1(3)4;/h(H4,2,3,4);1H
    Key: VYWQTJWGWLKBQA-UHFFFAOYSA-N
  • C(=O)(N)N.Cl
Properties
CH5ClN2O
Molar mass 96.51 g·mol−1
Appearance White solid
Density 1.34
Melting point Decomposes at 145 °C (293 °F; 418 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
H290, H302, H314, H315, H319, H335
P234, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P390, P403+P233, P405, P406, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Tracking categories (test):

Urea hydrochloride is the hydrochloride salt of urea. It is used in concrete etching and as a deep eutectic solvent. Its double salt with quinine hydrochloride has applications in surgical medicine.

Production

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Urea hydrochloride and diurea hydrochloride may be formed by treating solid urea with hydrogen chloride or concentrated hydrochloric acid.[1][2][3]

Properties

[edit]

Urea hydrochloride is a deliquescent white solid, soluble in water and ethanol.[2] It forms biuret and ammonium chloride upon heating to 130 °C (266 °F).[4] Thermal decomposition also yields condensation products of isocyanic acid, such as cyanuric acid.[1]

Uses

[edit]

Urea hydrochloride has uses as a concrete cleaning and etching agent, as it removes water-insoluble metal salts in solution.[5][6][7] In solution with betaine, urea hydrochloride has been investigated as a deep eutectic solvent for the dissolution of chitin.[8]

The double salt of quinine hydrochloride and urea hydrochloride has been used since the early 20th century as a long-duration injectable local anesthetic for use in various surgeries. The solution was formulated in France in 1881 and was first recommended for use as a local anesthetic in 1907.[9][10] While other quinine salts have the same anesthetic effect, quinine urea hydrochloride is preferred due to its exceptional solubility.[10] Operations involving a quinine urea hydrochloride solution included surgeries on the tonsils,[11] abdominal[12] and rectal tissues.[13][14] At the time, such operations were carried out using anesthetics that may have adverse side effects, such as cocaine.[13] Quinine urea hydrochloride was also used in the treatment of sciatica[15][16] and in 1931 was noted as one of the first treatments of anal fissures.[17] It was still in use by at least 1971, at which point it was noted as one of the few widely adopted injection treatments for hemorrhoids.[18]

References

[edit]
  1. ^ a b Beilstein, Friedrich Konrad (1893). Handbuch der organischen Chemie. Vol. 1. p. 1294. hdl:2027/osu.32435020872065. Verbindungen des Harnstoffes mit Mineralsäuren. 2CH4N2O·HCl. Zerfließliche Blätter (DESSAIGNES, J. 1854, 677). — CH4N2O·HCl. Sehr zerfließliche, blätterige Massen. Zerfällt, beim Lösen in Wasser, in HCl und freien Harnstoff (ERDMANN, KRUTSCH, J. pr. 25, 506). Zerfällt, beim Erhitzen, in Salmiak und Cyanursäure.
  2. ^ a b Gmelin, Leopold; Kraut, Karl Johann (1848). Gmelin-Krauts Handbuch der Chemie. Vol. 4. p. 294. hdl:2027/chi.13130191. [Verbindungen] (b) Mit Salzsäure. Der Harnstoff absorbirt das salzsaure Gas. PELOUZE, HAGEN. Sättigt man ihn damit, anfangs in der Kälte, zuletzt bei 100°, und befreit das gebildete blassgelbe Oel durch einen Luftstrom von der überschüssigen Salzsäure, so erstarrt das Oel beim Erkalten unter Wärmeentwicklung zu einer weißen, harten, blättrig strahligen Masse. Dieselbe zerfließt an der Luft rasch zu einer sehr sauren Flüssigkeit, welche Salzsäuredampf verbreitet; eben so wird sie durch Auflösen in Wasser sogleich in freie Salzsäure und freien Harnstoff zersetzt. In kochendem absoluten Weingeist scheint sie sich unverändert zu lösen, doch krystallisirt hieraus beim Erkalten sehr wenig Salmiak, der wahrscheinlich schon bei der Absorption des salzsauren Gases gebildet wurde. Salpetersäure fällt aus der weingeistigen Lösung sogleich salpetersauren Harnstoff. ERDMANN u. KRUTZSCH (J. pr. Chem. 25, 506).
  3. ^ Dessaignes, V. (1853). "Faits pour Contribuer à l'Histoire de Quelques Acides Organiques". Journal de pharmacie et de chimie. 25: 23–31. hdl:2027/pst.000052371189. J'ai obtenu un sous-chlorhydrate d'urée, en ajoutant à deux équivalents d'urée, un équivalent d'acide chlorhydrique, et abandonnant la solution sous une cloche avec de la chaux. C'est un beau sel cristallisant en longues lames parallèles et accolées. Il est peu déliquescent.
  4. ^ Berliner, J. F. T. (May 1936). "Crystal Urea: Industrial Development and Properties". Industrial & Engineering Chemistry. 28 (5): 517–522. doi:10.1021/ie50317a003. ISSN 0019-7866.
  5. ^ Онищенко, В. О.; Стороженко, Д. О.; Сененко, Н. Б.; Бунякіна, Н. В. (2018). "Mixes for Concrete Residues Removal from Sidewalk Tiles Production Molds Invention and Analysis" (PDF). International Journal of Engineering & Technology. 7 (4.8): 497–501.
  6. ^ US patent 5672279A, Sargent, R. Richard; Alender, Jeffrey Randolph & Moss, III, Thomas Hudson, "Method for using urea hydrochloride", issued 1997-09-30 
  7. ^ US patent 7658805B2, Netherton, Jason J., "Concrete cleaning and preparation composition", issued 2010-02-09 
  8. ^ Zhong, Yi; Cai, Jie; Zhang, Li-Na (October 2020). "A Review of Chitin Solvents and Their Dissolution Mechanisms". Chinese Journal of Polymer Science. 38 (10): 1047–1060. doi:10.1007/s10118-020-2459-x. ISSN 0256-7679.
  9. ^ "Quinine and Urea Hydrochloride". Wood Library-Museum of Anesthesiology. Retrieved July 5, 2024.
  10. ^ a b Thibault, Henry (September 1907). "A New Local Anesthetic". Journal of the Arkansas Medical Society. 4 (4): 149–150.
  11. ^ "Quinine and Urea Hydrochloride in Nose and Throat Surgery". Western Medical Reformer. LXXIV (5): 251–. 1914 – via Gale Nineteenth Century Collections Online.
  12. ^ Maxcy, Kenneth F. (1922). "Limitations to the Use of Quinine Intravenously in the Treatment of Malaria". Public Health Reports (1896-1970). 37 (12): 693–701. doi:10.2307/4576329. JSTOR 4576329.
  13. ^ a b Hertzler, Arthur E.; Brewster, Roger B.; Rogers, Ford B. (October 23, 1909). "Quinin and Urea Hydrochlorid as a Local Anesthetic". Journal of the American Medical Association. 53 (17): 1393–1395. doi:10.1001/jama.1909.92550170048002a.
  14. ^ Clemons, E. Jay (January 1918). "Internal Hemorrhoid Operation and After Care Under Quinine-Urea Hydrochloride Anesthesia". California State Journal of Medicine. 16 (1): 23–25. ISSN 0093-402X. PMC 1593352. PMID 18737501.
  15. ^ Rajendra Kumar Sen (1 May 1918). "Urea Hydrochloride". The Indian Medical Gazette. 53 (5): 195. ISSN 0019-5863. PMC 5201692. PMID 29008645. Wikidata Q42182364.
  16. ^ Garner, J. R. (May 1916). "The Treatment of Sciatica with Quinine and Urea Hydrochloride". Atlanta Journal-Record of Medicine. 63 (2): 59–63. PMC 9049479. PMID 36020631.
  17. ^ Howard, Christopher (April 1931). "Treatment of Anal Fissure". The Lancet. 217 (5617): 914–916. doi:10.1016/S0140-6736(00)30250-1.
  18. ^ Gologher, J. C. (1971). Surgery of the anus rectum and colon (3rd ed.). London: Bailliers Tindall. p. 126.
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