Hexamethoxymethylmelamine

Hexamethoxymethylmelamine
Names
Systematic IUPAC name
N2,N2,N4,N4,N6,N6-Hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine
Other names
Hexamethylolemelamine
Hexakis(methoxymethyl)melamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.019.475 Edit this at Wikidata
EC Number
  • 221-422-3
UNII
  • InChI=1S/C15H30N6O6/c1-22-7-19(8-23-2)13-16-14(20(9-24-3)10-25-4)18-15(17-13)21(11-26-5)12-27-6/h7-12H2,1-6H3
    Key: BNCADMBVWNPPIZ-UHFFFAOYSA-N
  • COCN(COC)C1=NC(=NC(=N1)N(COC)COC)N(COC)COC
Properties
C15H30N6O6
Molar mass 390.441 g·mol−1
Melting point 40–42 °C (104–108 °F; 313–315 K)
Hazards
GHS labelling:[1][2]
GHS07: Exclamation markGHS08: Health hazard
Danger
H317, H319, H341, H351
P264, P280, P305+P351+P338, P337+P313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hexa(methoxymethyl)melamine (HMMM) is a hemiaminal ether commonly used as a crosslinking agent in the production of coatings and rubber items. It is produced via the reaction of melamine with formaldehyde and excess methanol, with the later also acting as a solvent for the reaction. It can be considered as a monomeric intermediate in the formation of melamine resin.

Hexamethoxymethylmelamine is used along with resorcinol in the production of vehicle tires, where it improves adhesion between the rubber and the steel reinforcing cords. As it has some water solubility it slowly leaches out of the rubber; particularly from the particles formed as the tires wear-down through use.[3][4] Road runoff then introduces it into urban waters, where it has become a contaminant of emerging concern.[5][6][7]

See also

References

  1. ^ "Hexa(methoxymethyl)melamine". pubchem.ncbi.nlm.nih.gov. Retrieved 31 August 2022.
  2. ^ "C&L Inventory". echa.europa.eu. European Chemicals Agency. Retrieved 20 September 2022.
  3. ^ Johannessen, Cassandra; Parnis, J. Mark (October 2021). "Environmental modelling of hexamethoxymethylmelamine, its transformation products, and precursor compounds: An emerging family of contaminants from tire wear". Chemosphere. 280: 130914. doi:10.1016/j.chemosphere.2021.130914.
  4. ^ Johannessen, Cassandra; Helm, Paul; Metcalfe, Chris D. (January 2021). "Runoff of the Tire-Wear Compound, Hexamethoxymethyl-Melamine into Urban Watersheds". Archives of Environmental Contamination and Toxicology. 82: 162–170. doi:10.1007/s00244-021-00815-5. PMC 7846915.
  5. ^ Tian, Zhenyu; Peter, Katherine T.; Gipe, Alex D.; Zhao, Haoqi; Hou, Fan; Wark, David A.; Khangaonkar, Tarang; Kolodziej, Edward P.; James, C. Andrew (21 January 2020). "Suspect and Nontarget Screening for Contaminants of Emerging Concern in an Urban Estuary". Environmental Science & Technology. 54 (2): 889–901. Bibcode:2020EnST...54..889T. doi:10.1021/acs.est.9b06126. PMID 31887037. S2CID 209518958.
  6. ^ Johannessen, Cassandra; Helm, Paul; Metcalfe, Chris D. (October 2021). "Detection of selected tire wear compounds in urban receiving waters". Environmental Pollution. 287: 117659. doi:10.1016/j.envpol.2021.117659. PMID 34426371.
  7. ^ Seiwert, Bettina; Klöckner, Philipp; Wagner, Stephan; Reemtsma, Thorsten (August 2020). "Source-related smart suspect screening in the aqueous environment: search for tire-derived persistent and mobile trace organic contaminants in surface waters". Analytical and Bioanalytical Chemistry. 412 (20): 4909–4919. doi:10.1007/s00216-020-02653-1. PMC 7334239. PMID 32382968.