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Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate)

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Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate)
Names
Preferred IUPAC name
2,2-Bis({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoyl]oxy}methyl)propane-1,3-diyl bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoate]
Other names
Anox 20, Irganox 1010, Dovernox 10
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.021 Edit this at Wikidata
EC Number
  • 229-722-6
RTECS number
  • DA8340900
UNII
  • InChI=1S/C73H108O12/c1-65(2,3)49-33-45(34-50(61(49)78)66(4,5)6)25-29-57(74)82-41-73(42-83-58(75)30-26-46-35-51(67(7,8)9)62(79)52(36-46)68(10,11)12,43-84-59(76)31-27-47-37-53(69(13,14)15)63(80)54(38-47)70(16,17)18)44-85-60(77)32-28-48-39-55(71(19,20)21)64(81)56(40-48)72(22,23)24/h33-40,78-81H,25-32,41-44H2,1-24H3
    Key: BGYHLZZASRKEJE-UHFFFAOYSA-N
  • CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)CCC(=O)OCC(COC(=O)CCC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C)(COC(=O)CCC3=CC(=C(C(=C3)C(C)(C)C)O)C(C)(C)C)COC(=O)CCC4=CC(=C(C(=C4)C(C)(C)C)O)C(C)(C)C
Properties
C73H108O12
Molar mass 1177.655 g·mol−1
Appearance White solid
Melting point 110–125 °C (230–257 °F; 383–398 K)
<0.1 g/ml
Solubility in Acetone 0.75 g/ml
Solubility in Toluene 0.5 g/ml
Solubility in Methanol <0.1 g/ml
Hazards
GHS labelling:
H413
P273, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) is a chemical compound composed of 4 sterically hindered phenols linked through a pentaerythritol core. It is used as primary antioxidant for stabilizing polymers, particularly polyethylene and polypropylene.

Synthesis

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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 pentaerythritol gives the final product. Driving this reaction to completion can be difficult and commercial samples often contain low levels of the tri-ester.

Properties

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The linking of phenols together with pentaerythritol maintains their activity with greatly reduced volatility. This is important during the processing and molding steps where the plastic is heated to molten, typically several hundred degrees.[1]

See also

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References

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  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.
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