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2,4,6-Tris(dimethylaminomethyl)phenol

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2,4,6-Tris(dimethylaminomethyl)phenol
Names
IUPAC name
2,4,6-Tris[(dimethylamino)methyl]phenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.831 Edit this at Wikidata
EC Number
  • 202-013-9
UNII
UN number 2735
  • InChI=1S/C15H27N3O/c1-16(2)9-12-7-13(10-17(3)4)15(19)14(8-12)11-18(5)6/h7-8,19H,9-11H2,1-6H3
    Key: AHDSRXYHVZECER-UHFFFAOYSA-N
  • CN(C)CC1=CC(=C(C(=C1)CN(C)C)O)CN(C)C
Properties
C15H27N3O
Molar mass 265.401 g·mol−1
Density 0.974 at 15°C
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H315, H319
P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4,6-Tris(dimethylaminomethyl)phenol is an aromatic organic chemical that has tertiary amine and phenolic hydroxyl functionality in the same molecule.[1] The formula is C15H27N3O and the CAS Registry Number is 90-72-2. It is REACH registered and the European Community Number is 202-013-9.[2][3][4]

Uses

A key use is as a catalyst for epoxy resin chemistry. It can be used as a homopolymerization catalyst for epoxy resins and also as an accelerator with epoxy resin curing agents. It is then further used in coatings,[5] sealants, composites,[6] adhesives[7] and elastomers. It has been stated that it is probably the most widely used room temperature accelerator for two-component epoxy resin systems.[8][9] The kinetics of curing with and without this accelerator have been extensively studied.[10][11] It is the usual benchmark or control used when other catalysts and accelerators are being developed and tested.[12]

In addition to its use in epoxy chemistry, it is also used in polyurethane chemistry for example by grafting the molecule into the polymer backbone.[13] It is also used as a trimerization catalyst with polymeric MDI.[14]

Polyether ether ketones may also be grafted with the molecule which then finds use in lithium batteries.[15]

The high functionality of the molecule means it can be used to complex some transition metals and this has also been studied.[16]

Often cited weaknesses are yellowing and odor.[17]

Manufacture

The material is a Mannich base and is manufactured by reacting phenol, formaldehyde and dimethylamine in a reactor under vacuum and removing the water produced.

Toxicity

It is classed as a high volume chemical and as such, its toxicity profile has been extensively studied.[18][19][20]

References

  1. ^ "Human Metabolome Database: Showing metabocard for 2,4,6-Tris(dimethylaminomethyl)phenol (HMDB0247627)". hmdb.ca. Retrieved 2024-06-04.
  2. ^ PubChem. "2,4,6-Tris(dimethylaminomethyl)phenol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-06-05.
  3. ^ "Registration Dossier - ECHA". echa.europa.eu. Retrieved 2024-06-05.
  4. ^ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2024-06-05.
  5. ^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 15 Master of Science Thesis April 1997 Imperial College London
  6. ^ Niazi, Mina; Beheshty, Mohammad Hosain (2019-04-01). "A new latent accelerator and study of its effect on physical, mechanical and shelf-life of carbon fiber epoxy prepreg". Iranian Polymer Journal. 28 (4): 337–346. doi:10.1007/s13726-019-00704-8. ISSN 1735-5265.
  7. ^ Schlechte, Jay S. (2023), "Advances in epoxy adhesives", Advances in Structural Adhesive Bonding, Elsevier, pp. 3–67, doi:10.1016/b978-0-323-91214-3.00030-2, ISBN 978-0-323-91214-3, retrieved 2024-06-05
  8. ^ Seo, Jiae; Yui, Nobuhiko; Seo, Ji-Hun (January 2019). "Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin". Chemical Engineering Journal. 356: 303–311. Bibcode:2019ChEnJ.356..303S. doi:10.1016/j.cej.2018.09.020. ISSN 1385-8947.
  9. ^ Chen, Fengjun; Liu, Fan; Du, Xiaogang (2023-01-10). "Molecular dynamics simulation of crosslinking process and mechanical properties of epoxy under the accelerator". Journal of Applied Polymer Science. 140 (2). doi:10.1002/app.53302. ISSN 0021-8995.
  10. ^ Yevtushenko, G.T.; Moshinskii, L.Ya.; Beletskaya, T.V. (January 1974). "Kinetics of hardening of ED-5 epoxy resins with anhydrides in the presence of 2.4,6-Tris-(Dimethylaminomethyl)phenol". Polymer Science U.S.S.R. 16 (6): 1557–1562. doi:10.1016/0032-3950(74)90421-3. ISSN 0032-3950.
  11. ^ Hesabi, Mohammadnabi; Salimi, Ali; Beheshty, Mohammad Hosain (May 2017). "Effect of tertiary amine accelerators with different substituents on curing kinetics and reactivity of epoxy/dicyandiamide system". Polymer Testing. 59: 344–354. doi:10.1016/j.polymertesting.2017.02.023. ISSN 0142-9418.
  12. ^ Fedtke, Manfred (January 1987). "Acceleration mechanisms in curing reactions involving model systems". Makromolekulare Chemie. Macromolecular Symposia. 7 (1): 153–168. doi:10.1002/masy.19870070114. ISSN 0258-0322.
  13. ^ Chung, Yong-Chan; Kim, Ji Young; Park, Ji Eun; Chun, Byoung Chul (2021-04-01). "Hydrophilic Modification of a Polyurethane Surface Using Grafted 2,4,6-Tris(dimethylaminomethyl) Phenol". Fibers and Polymers. 22 (4): 904–915. doi:10.1007/s12221-021-1406-y. ISSN 1875-0052.
  14. ^ Imai, Yoshio; Hidai, Takao; Inukai, Takao; Nakanishi, Takehisa (January 1986). "Study on Isocyanurate-Modified MDI. 1 — Preparation". Cellular Polymers. 5 (1): 13–23. doi:10.1177/026248938600500102. ISSN 0262-4893.
  15. ^ Kumar, Sonu; Bhushan, Mani; Shahi, Vinod K. (February 2020). "Cross-linked amphoteric membrane: Sulphonated poly(ether ether ketone) grafted with 2,4,6-tris(dimethylaminomethyl)phenol using functionalized side chain spacers for vanadium redox flow battery". Journal of Power Sources. 448: 227358. Bibcode:2020JPS...44827358K. doi:10.1016/j.jpowsour.2019.227358. ISSN 0378-7753.
  16. ^ Romashkina, E. P.; Ilyukhin, A. B.; Strashnova, S. B.; Koval’chukova, O. V.; Palkina, K. K.; Sergienko, V. S.; Zaitsev, B. E. (2011-03-01). "Complex compounds of some p, d, and f metals with 2,4,6-tris(N,N-dimethylaminomethyl)phenol (HL): Crystal and molecular structure of H4L(NO3)3 · H2O and H4LCl3 · 3H2O". Russian Journal of Inorganic Chemistry. 56 (3): 350–356. doi:10.1134/S0036023611030193. ISSN 1531-8613.
  17. ^ Chiang, Tzu Hsuan; Hsieh, Tsung-Eong (December 2007). "Effect of tertiary amines on yellowing of UV-curable epoxide resins". Polymer International. 56 (12): 1544–1552. doi:10.1002/pi.2300. ISSN 0959-8103.
  18. ^ Kanekrva, Lasse; Estlander, Tuula; Jolanki, Riitta (December 1996). "OCCUPATIONAL ALLERGIC CONTACT DERMATITIS CAUSED BY 2,4,6-TRIS-(DIMETHYLAMINOMETHYL)PHENOL, AND REVIEW OF SENSITIZING EPOXY RESIN HARDENERS". International Journal of Dermatology. 35 (12): 852–856. doi:10.1111/j.1365-4362.1996.tb05050.x. ISSN 0011-9059. PMID 8970840.
  19. ^ Aalto-Korte, Kristiina; Pesonen, Maria; Suuronen, Katri (December 2015). "Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sensitizing products, and diagnosis". Contact Dermatitis. 73 (6): 336–342. doi:10.1111/cod.12445. ISSN 0105-1873. PMID 26230376.
  20. ^ Geier, Johannes; Dickel, Heinrich; Schröder-Kraft, Claudia; Gina, Michal; Simon, Dagmar; Weisshaar, Elke; Lang, Claudia; Brans, Richard; Bauer, Andrea; Löffler, Harald; Schubert, Steffen; for the IVDK (April 2023). "2,4, 6-Tris (dimethylaminomethyl)phenol: The allergen which came in from the cold". Contact Dermatitis. 88 (4): 316–318. doi:10.1111/cod.14268. ISSN 0105-1873. PMID 36524787.

Further reading

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