Description
Grotan BK is a triazine derivative contained in cutting fluids. It is a formaldehyde releaser. Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine is a light-yellow liquid. It is a formaldehyde condensate product that is used as an antimicrobial agent in metal working fluids.
Chemical Properties
Light Yellow Solid
Uses
Hexahydro-l,3,5-tris-(2-hydroxyethyl)triazin is used in organic synthesis; as a bactericide in cooling fluids and various cosmetic products; formaldehyde liberator.
General Description
Viscous yellow liquid.
Air & Water Reactions
Water soluble.
Reactivity Profile
Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine is an amine and an alcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Health Hazard
Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine (TA, CAS 4719-04-4) is a widely used biocide added to water-based metalworking fluids (MWF) to control microbial populations. However, uncontrolled concentrations of this biocide within metalworking fluids may induce allergic pneumonitis. The mechanism may involve TA eliminating other competing microorganisms while simultaneously inducing the emergence of biocide-resistant mycobacteria, leading to their excessive proliferation within the fluid's sedimentation tanks
[6]. Furthermore, TA rapidly releases formaldehyde in diluted aqueous solutions. This substance exhibits strong irritant and corrosive effects on rabbit skin, eyes, and upper respiratory tract, attributed to the formation of irritant formaldehyde and 2-aminoethanol. As formaldehyde is released from TA, this substance is classified as a Category 4 carcinogen alongside formaldehyde. The aerosol form of TA is classified as a Category 2 carcinogen. As no data currently exist on the systemic bioavailability of TA released through hydrolysis in tissues, nor is there experimental evidence indicating formaldehyde reaches germ cells, TA has been categorised as a Category 3B germ cell mutagen. Skin contact is not anticipated to contribute significantly to systemic toxicity
[7].
Fire Hazard
Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine is probably combustible.
Flammability and Explosibility
Not classified
Contact allergens
Grotan BK is a triazine derivative contained as a bio cide in cutting fluids. It is a formaldehyde releaser.
Dermatitis, delayed-type allergic conjunctivitis, and
asthma were described.
Synthesis
General procedure for the synthesis of hydroxyethyl hexahydrohomotriazine from formaldehyde and 2-aminoethanol: To 6.1 g (0.1 mol) of 2-aminoethanol was added 3.0 g (0.1 mol as formaldehyde) of a 20 mL methanol solution of paraformaldehyde, and the mixture was stirred for 48 h at room temperature. Upon completion of the reaction, the solvent was removed by rotary evaporator and the residue was distilled under reduced pressure to give 6.3 g (86% yield) of light yellow viscous liquid. The physicochemical properties of the obtained compound (I) were in accordance with the data reported in literature [9].
Toxics Screening Level
The initial threshold screening level (ITSL) for 1,3,5-triazine-1,3,5(2H,4H,6H)-triethanol (CAS
# 4719-04-4) is 0.015 μg/m3 with an annual averaging time.
References
[1] Helvetica Chimica Acta, 2007, vol. 90, # 9, p. 1765 - 1780
[2] Russian Journal of Applied Chemistry, 2015, vol. 88, # 7, p. 1174 - 1177
[3] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2015, vol. 88, # 7, p. 1083 - 1086,4
[4] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1771,1773; engl. Ausg. S. 1869, 1871
[5] Chemische Berichte, 1949, vol. 82, p. 316,326
[6] PRETTY J, GLASER R, III J J, et al. A technique for the identification and direct analysis of hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine in metalworking fluids using electrospray-mass spectrometry[J]. Analyst, 2004, 11: 1150-1155. DOI:10.1039/B404578E.
[7] HARTWIG A. <i>N</i>,<i>N’</i>,<i>N”</i>-Tris(β-hydroxyethyl)hexahydro-1,3,5-triazine: MAK Value Documentation, addendum - Translation of the German version from 2023.[J]. The MAK collection for occupational health and safety, 2025, 10 3: Doc049. DOI:10.34865/mb471904kske10\_3ad.
