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

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	2082-79-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	15539;
ECHA InfoCard	100.016.560
EC Number	218-216-0;
PubChem CID	16386;
UNII	V88J661G2P;
CompTox Dashboard (EPA)	DTXSID8027456 ;
	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,8-26H2,1-7H3 Key: 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−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)
Solubility in water	2.85 µg/L
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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,^[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

^ "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.

[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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