Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
Names | |
---|---|
Other names
Trade names:
| |
Identifiers | |
3D model (JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.016.560 |
EC Number |
|
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C35H62O3 | |
Molar mass | 530.878 g·mol−1 |
Appearance | White solid |
Density | 1.012 |
Melting point | 50–52 °C (122–126 °F; 323–325 K) |
Boiling point | 323 °C (613 °F; 596 K) |
2.85 µg/L | |
Hazards | |
GHS labelling:[1] | |
Warning | |
H315, H317, H319, H335, H413 | |
P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a hindered phenolic antioxidant commonly used as a polymer stabiliser.
Synthesis
[edit]Base catalysed Michael addition of methyl acrylate to 2,6-di-tert-butylphenol forms the intermediate butyl-phloretic ester. High temperature transesterification of this with stearyl alcohol gives the final product.
Applications
[edit]Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is significantly less volatile than simpler phenolic antioxidants such as butylhydroxytoluene (BHT). This makes it more suitable to stabilising plastics, as it is not driven out by the high temperatures experienced during plastic extrusion and moulding,[2] when they are heated to 150-320 °C (300–600 °F).[3] It is widely used in the commodity plastics, particularly in polyethylenes and polypropylene. It has approval for use in food contact materials, such as plastic food packaging in the EU and US,[4] amongst others.
It is one of the most common polymer antioxidants, in part because of its comparatively low price. The stearyl tail reduces volatility and gives good chemical compatibility with plastics but contributes nothing to antioxidant performance. When higher performance is needed pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) a common alternative.[5]
References
[edit]- ^ "Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate". pubchem.ncbi.nlm.nih.gov.
- ^ Vulic, Ivan; Vitarelli, Giacomo; Zenner, John M. (January 2002). "Structure–property relationships: phenolic antioxidants with high efficiency and low colour contribution". Polymer Degradation and Stability. 78 (1): 27–34. doi:10.1016/S0141-3910(02)00115-5.
- ^ Ragaert, Kim; Delva, Laurens; Van Geem, Kevin (November 2017). "Mechanical and chemical recycling of solid plastic waste". Waste Management. 69: 24–58. Bibcode:2017WaMan..69...24R. doi:10.1016/j.wasman.2017.07.044. PMID 28823699.
- ^ Neal-Kluever, April P.; Bailey, Allan B.; Hatwell, Karen R. (December 2015). "Safety assessment for octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate (CAS Reg. No. 2082-79-3) from use in food contact applications". Food and Chemical Toxicology. 86: 176–190. doi:10.1016/j.fct.2015.10.004. PMID 26482640.
- ^ Jipa, S.; Setnescu, R.; Setnescu, T.; Cazac, C.; Budrugeac, P.; Mihalcea, I. (January 1993). "The comparative effectiveness of some commercial antioxidants as studied by lyoluminescence". Polymer Degradation and Stability. 40 (1): 101–107. doi:10.1016/0141-3910(93)90197-Q.