1,2,2,6,6-Pentamethyl-4-piperidinol
[CAS# 2403-89-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 1,2,2,6,6-Pentamethyl-4-piperidinol
• Synonyms: 1,2,2,6,6-Pentamethylpiperidin-4-ol; N-Methyl-2,2,6,6-tetramethyl-4-piperidinol
• Molecular Formula: C₁₀H₂₁NO
• Molecular Weight: 171.28
• CAS Registry Number: 2403-89-6
• EC Number: 219-292-8
• SMILES: CC1(CC(CC(N1C)(C)C)O)C

Properties

• Density: 0.967
• Melting point: 70-76 °C
• Boiling point: 238 °C
• Flash point: 118 °C
• Water solubility: 4.8 g/100 mL (20 °c)

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302-H314-H317-H318-H411-H412
• Safety Statements: P260-P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Skin corrosion	Skin Corr.	1A	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1	H314
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

1,2,2,6,6-Pentamethyl-4-piperidinol, commonly known as PMP, was discovered in the mid-20th century during research into piperidine derivatives. Its synthesis involves the reaction of piperidine with formaldehyde and methyl ethyl ketone, leading to the formation of a tertiary amine alcohol. This discovery expanded the scope of piperidine chemistry and provided chemists with a versatile compound for various applications.

PMP is widely used as a UV stabilizer in plastics, coatings, and adhesives. It helps prevent the degradation of materials caused by exposure to ultraviolet radiation.

PMP serves as a polymer additive in various applications, including automotive, construction, and packaging industries. It enhances the thermal stability, weather resistance, and mechanical properties of polymers.

PMP functions as an antioxidant in rubber products, lubricants, and petroleum derivatives. It inhibits oxidation reactions, preventing the formation of harmful byproducts and extending the shelf life of materials.

PMP derivatives are employed as photoinitiators in photopolymerization processes. They initiate polymerization reactions upon exposure to light, leading to the formation of crosslinked polymer networks in coatings, adhesives, and dental materials.

PMP derivatives are utilized as corrosion inhibitors in metalworking fluids, lubricants, and cooling systems. They form protective films on metal surfaces, preventing corrosion and extending the lifespan of machinery and equipment.

PMP is added to adhesives and sealants to improve their bonding strength, adhesion properties, and resistance to environmental factors such as moisture and temperature fluctuations.

PMP derivatives serve as intermediates in the synthesis of specialty chemicals, pharmaceuticals, and agrochemicals. They undergo various chemical transformations to produce compounds with specific functional groups and properties.

References

2017. Preparation of controlled molecular weight and narrow distribution HALS and its application. *Journal of Polymer Research*, 24(4).
DOI: 10.1007/s10965-017-1223-6

2014. Synthesis of piperazine-1,4-dipropanoic acid di(1,2,2,6,6-pentamethyl-4-piperidine)yl ester as a photostabilizer. *Russian Journal of General Chemistry*, 84(11).
DOI: 10.1134/s1070363214110292

1982. Pathways of photooxidation of 1,2,2,6,6-pentamethyl-4-piperidol by ketones. *Chemistry of Heterocyclic Compounds*, 18(12).
DOI: 10.1007/bf00506616