Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine
[CAS# 4719-04-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Triazines
• Name: Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine
• Synonyms: 1,3,5-Tris(2-hydroxyethyl)hexahydro-1,3,5-triazine; 1,3,5-Triazine-1,3,5(2H,4H,6H)-triethanol
• Molecular Formula: C₉H₂₁N₃O₃
• Molecular Weight: 219.28
• CAS Registry Number: 4719-04-4
• EC Number: 225-208-0
• SMILES: C1N(CN(CN1CCO)CCO)CCO

Properties

• Water solubility: Soluble (>=1 g/100 mL at 24 °C)
• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 399.9±42.0 °C 760 mmHg (Calc.)^*
• Flash point: 220.1±26.5 °C (Calc.)^*
• Index of refraction: 1.53 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H302-H317-H319-H330-H372
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P319-P320-P321-P330-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	3	H331
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1	H314
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine is a heterocyclic organic compound widely used for its antimicrobial properties, particularly as a preservative and biocide. The structure of this compound consists of a six-membered s-triazine ring, in which three nitrogen atoms alternate with three carbon atoms, each carbon atom being substituted with a hydroxyethyl group. This chemical structure was developed through studies on triazine derivatives, a class known for their chemical stability and versatile reactivity.

The discovery and synthesis of hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine emerged in the mid-20th century as researchers investigated effective biocidal agents for industrial applications. It is typically prepared by the reaction of formaldehyde with monoethanolamine under controlled conditions. The process involves the formation of a cyclic trimer where each nitrogen atom in the triazine ring bonds with a hydroxyethyl group, resulting in a highly water-soluble compound with notable antimicrobial activity.

One of the principal applications of hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine is in the oil and gas industry, where it is used as a biocide to control the growth of sulfate-reducing bacteria. These bacteria are known to produce hydrogen sulfide, leading to corrosion of pipelines and other infrastructure, as well as safety hazards. The triazine compound is injected into drilling fluids, production waters, and other related systems to mitigate microbial activity, thus protecting equipment and maintaining operational safety.

In addition to its role in oilfield applications, hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine finds use in metalworking fluids, adhesives, paints, and cooling towers. In these environments, microbial contamination can degrade product quality, reduce equipment lifespan, and pose health risks. The compound's antimicrobial properties help maintain the stability and effectiveness of these systems by inhibiting bacterial and fungal growth.

The mode of action of hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine involves the release of formaldehyde, which acts as the primary biocidal agent. Upon decomposition in aqueous environments, the compound slowly releases formaldehyde, which interacts with microbial proteins and nucleic acids, leading to cell death. This mechanism offers a controlled and prolonged antimicrobial effect, suitable for applications requiring extended protection.

Environmental considerations regarding the use of hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine have been a subject of study, primarily due to concerns about formaldehyde release. Formaldehyde is a recognized hazardous substance, associated with respiratory irritation and other health effects. Therefore, the use of the triazine compound is regulated in many jurisdictions, and efforts are made to optimize dosages to achieve microbial control while minimizing potential exposure risks.

Physical properties of hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine include its appearance as a colorless to pale yellow liquid, high solubility in water, and stability under normal storage conditions. It is compatible with a wide range of formulation components, making it a flexible additive for industrial biocide formulations. However, it should be stored in a cool, dry place, away from strong oxidizing agents and acids, which may accelerate decomposition.

Handling of hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine requires appropriate safety measures. Personal protective equipment such as gloves, goggles, and suitable clothing should be used to prevent skin and eye contact. Ventilation should be adequate to avoid inhalation of vapors or aerosols. In case of spills, the area should be ventilated, and spills should be contained and cleaned up using absorbent materials compatible with the substance.

Ongoing research into hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine aims to refine its applications and improve formulations that enhance efficacy while reducing environmental and health impacts. Modifications to the triazine core and variations in substitution patterns continue to be explored for the development of new antimicrobial agents. Nevertheless, hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine remains a significant compound within industrial microbiological control strategies, valued for its effectiveness, stability, and versatility.

References

1976. An evaluation of the mutagenicity of the cutting oil preservative Grotan BK. Mutation Research/Genetic Toxicology, 36(1).
DOI: 10.1016/0165-1218(76)90021-5

2004. Formaldehyde releasing compounds. Directory of Microbicides for the Protection of Materials.
DOI: 10.1007/1-4020-2818-0_26

2011. Susceptibility of Mycobacterium immunogenum and Pseudomonas fluorescens to Formaldehyde and Non-Formaldehyde Biocides in Semi-Synthetic Metalworking Fluids. International Journal of Molecular Sciences, 12(1).
DOI: 10.3390/ijms12010725