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Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

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Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
Names
Other names
  • Stearyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate
  • Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoate
  • Octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate
  • 3,5-Di-tert-butyl-4-hydroxyphenylpropionic acid octadecyl ester
  • Antioxidant 1076

Trade names:

  • Irganox 1076 (BASF)
  • Anox PP18 (SI Group)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.560 Edit this at Wikidata
EC Number
  • 218-216-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C35H62O3/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26-38-32(36)25-24-29-27-30(34(2,3)4)33(37)31(28-29)35(5,6)7/h27-28,37H,8-26H2,1-7H3Key: nChIKey=SSDSCDGVMJFTEQ-UHFFFAOYSA-N
SMILES
  • C(CC(OCCCCCCCCCCCCCCCCCC)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1
Properties
Chemical formula C35H62O3
Molar mass 530.878 g·mol
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)
Solubility in water 2.85 µg/L
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H317, H319, H335, H413
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a hindered phenolic antioxidant commonly used as a polymer stabiliser.

Synthesis

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

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, when they are heated to 150-320 °C (300–600 °F). 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, 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.

References

  1. "Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate". pubchem.ncbi.nlm.nih.gov.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
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