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
3D model (JSmol)
ECHA InfoCard 100.016.560 Edit this at Wikidata
EC Number
  • 218-216-0
  • 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,8-26H2,1-7H3
    Key: nChIKey=SSDSCDGVMJFTEQ-UHFFFAOYSA-N
  • C(CC(OCCCCCCCCCCCCCCCCCC)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1
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
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

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,[1] when they are heated to 150-320 °C (300–600 °F).[2] 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,[3] 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.[4]

References

  1. ^ 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.
  2. ^ Ragaert, Kim; Delva, Laurens; Van Geem, Kevin (November 2017). "Mechanical and chemical recycling of solid plastic waste". Waste Management. 69: 24–58. doi:10.1016/j.wasman.2017.07.044. PMID 28823699.
  3. ^ 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.
  4. ^ 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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