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
CAS Number	3089-11-0  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3183742
ChemSpider	56259
ECHA InfoCard	100.019.475
EC Number	221-422-3
PubChem CID	62479
UNII	890DZ25729
CompTox Dashboard (EPA)	DTXSID001037068 DTXSID9027520, DTXSID001037068
InChI 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
SMILES COCN(COC)C1=NC(=NC(=N1)N(COC)COC)N(COC)COC
Properties
Chemical formula	C15H30N6O6
Molar mass	390.441 g·mol−1
Melting point	40–42 °C (104–108 °F; 313–315 K)
Hazards
GHS labelling: [1] [2]
Pictograms
Signal word	Danger
Hazard statements	H317, H319, H341, H351
Precautionary statements	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). Infobox references

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

• Rubber pollution

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.