1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine
[CAS# 15875-13-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Triazines
• Name: 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine
• Synonyms: N,N,N',N',N'',N''-Hexamethyl-1,3,5-triazine-1,3,5(2H,4H,6H)-tripropanamine
• Molecular Formula: C₁₈H₄₂N₆
• Molecular Weight: 342.57
• CAS Registry Number: 15875-13-5
• EC Number: 240-004-1
• SMILES: CN(C)CCCN1CN(CN(C1)CCCN(C)C)CCCN(C)C

Properties

• Density: 0.92
• Boiling point: 141-142 °C
• Refractive index: 1.478
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H312-H314-H315-H318
• Safety Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P332+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1C	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

• Transport Information: UN 2735

Discovery and Applications

1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine is a chemical compound widely used in industrial applications, particularly in the oil and gas sector. This compound is a triazine derivative, characterized by a cyclic structure with three dimethylaminopropyl side chains. Its synthesis and development stemmed from the need for efficient corrosion inhibitors and biocides.

The discovery of 1,3,5-tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine can be traced back to efforts to create effective, long-lasting corrosion inhibitors for the petroleum industry. Corrosion in pipelines and equipment is a major issue that leads to significant maintenance costs and operational downtime. The compound’s structure, with multiple nitrogen atoms and tertiary amine groups, offers strong binding to metal surfaces, forming a protective barrier that inhibits corrosive processes. This makes it particularly effective in the harsh environments encountered in oil extraction and transportation.

In addition to its use as a corrosion inhibitor, 1,3,5-tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine functions as a biocide, preventing microbial growth in industrial systems. Microorganisms such as sulfate-reducing bacteria (SRB) are notorious for accelerating corrosion and causing biofouling in pipelines and storage tanks. The compound’s biocidal properties help in controlling microbial populations, ensuring the smooth operation of industrial systems. Its effectiveness as a biocide is due to its ability to penetrate biofilms and disrupt microbial cell functions.

In water treatment processes, 1,3,5-tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine is applied to control microbial growth and prevent scaling. Its versatility makes it suitable for use in various water systems, including cooling towers, boilers, and wastewater treatment facilities. It is also employed in formulations for paints and coatings, where it acts as a preservative by inhibiting microbial degradation of the materials.

The compound’s synthesis involves the condensation of formaldehyde with dimethylamine and a triamine precursor. This reaction forms the triazine ring structure, with the dimethylaminopropyl groups attached to the nitrogen atoms. The resulting compound is a stable, water-soluble molecule that is easily applied in various industrial settings.

The broad application of 1,3,5-tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine in the oil and gas industry, water treatment, and coatings underscores its importance in addressing corrosion and microbial growth challenges. Its dual role as a corrosion inhibitor and biocide highlights its versatility and effectiveness in maintaining the integrity of industrial systems.

References

2016. Non-isocyanate route to amides and polyamides through reactions of aryl N-phenylcarbamates with carboxylic acids. Journal of Polymer Research.
DOI: https://doi.org/10.1007/s10965-016-1052-z

2005. Isocyanatoisocyanurates by Partial Trimerization of Polyisocyanates. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-018-00919