Hexamethoxymethylmelamine
{{Chembox
| ImageFile = Hexa(methoxymethyl)melamine.svg
| ImageSize = 200px
| ImageAlt =
| SystematicName = N2,N2,N4,N4,N6,N6-Hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine
| OtherNames = Hexamethylolemelamine
Hexakis(methoxymethyl)melamine
| Section1 = {{Chembox Identifiers
| CASNo = 3089-11-0
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChEMBL = 3183742
| ChemSpiderID = 56259
| EC_number = 221-422-3
| PubChem = 62479
| UNII = 890DZ25729
| StdInChI=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
| StdInChIKey = BNCADMBVWNPPIZ-UHFFFAOYSA-N
| SMILES = COCN(COC)C1=NC(=NC(=N1)N(COC)COC)N(COC)COC
}}
| Section2 = {{Chembox Properties
|C=15|H=30|N=6|O=6
| MolarMass =
| Appearance =
| Density =
| MeltingPtC = 40-42
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| GHS_ref={{cite web |title=Hexa(methoxymethyl)melamine |url=https://pubchem.ncbi.nlm.nih.gov/compound/62479#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=31 August 2022 |language=en}}{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/50601 |website=echa.europa.eu |publisher=European Chemicals Agency |access-date=20 September 2022}}
| GHSPictograms = {{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|317|319|341|351}}
| PPhrases = {{P-phrases|264|280|305+351+338|337+313}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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.{{cite journal |last1=Johannessen |first1=Cassandra |last2=Parnis |first2=J. Mark|title=Environmental modelling of hexamethoxymethylmelamine, its transformation products, and precursor compounds: An emerging family of contaminants from tire wear|journal=Chemosphere |date=October 2021 |volume=280 |pages=130914 |doi=10.1016/j.chemosphere.2021.130914}}{{cite journal |last1=Johannessen |first1=Cassandra |last2=Helm |first2=Paul |last3=Metcalfe |first3=Chris D. |title=Runoff of the Tire-Wear Compound, Hexamethoxymethyl-Melamine into Urban Watersheds |journal=Archives of Environmental Contamination and Toxicology|date=January 2021 |volume=82 |pages=162–170 |doi=10.1007/s00244-021-00815-5|doi-access=free |pmc=7846915 }} Road runoff then introduces it into urban waters, where it has become a contaminant of emerging concern.{{cite journal |last1=Tian |first1=Zhenyu |last2=Peter |first2=Katherine T. |last3=Gipe |first3=Alex D. |last4=Zhao |first4=Haoqi |last5=Hou |first5=Fan |last6=Wark |first6=David A. |last7=Khangaonkar |first7=Tarang |last8=Kolodziej |first8=Edward P. |last9=James |first9=C. Andrew |title=Suspect and Nontarget Screening for Contaminants of Emerging Concern in an Urban Estuary |journal=Environmental Science & Technology |date=21 January 2020 |volume=54 |issue=2 |pages=889–901 |doi=10.1021/acs.est.9b06126|pmid=31887037 |bibcode=2020EnST...54..889T |s2cid=209518958 }}{{cite journal |last1=Johannessen |first1=Cassandra |last2=Helm |first2=Paul |last3=Metcalfe |first3=Chris D. |title=Detection of selected tire wear compounds in urban receiving waters |journal=Environmental Pollution |date=October 2021 |volume=287 |pages=117659 |doi=10.1016/j.envpol.2021.117659|pmid=34426371 }}{{cite journal |last1=Seiwert |first1=Bettina |last2=Klöckner |first2=Philipp |last3=Wagner |first3=Stephan |last4=Reemtsma |first4=Thorsten |title=Source-related smart suspect screening in the aqueous environment: search for tire-derived persistent and mobile trace organic contaminants in surface waters |journal=Analytical and Bioanalytical Chemistry |date=August 2020 |volume=412 |issue=20 |pages=4909–4919 |doi=10.1007/s00216-020-02653-1|pmid=32382968 |pmc=7334239 }}
See also
References
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