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

{{DISPLAYTITLE:Pentaerythritol tetrakis(3,5-di-''tert''-butyl-4-hydroxyhydrocinnamate)}}
{{Chembox
| Name = Pentaerythritol tetrakis(3,5-di-''tert''-butyl-4-hydroxyhydrocinnamate
<!-- Images -->
| ImageFile = PAO-2_100.svg
| ImageSize =
| ImageAlt =
<!-- Names -->
| PIN = 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]
| OtherNames = Anox 20, Irganox 1010, Dovernox 10
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 6683-19-8
| PubChem = 64819
| RTECS = DA8340900
| ChEMBL = 3187856
| UNII = 255PIF62MS
| ChemSpiderID = 58351
| SMILES = 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
| InChI = 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
| InChIKey =BGYHLZZASRKEJE-UHFFFAOYSA-N
| EC_number = 229-722-6
}}
| Section2 = {{Chembox Properties
| C=73| H=108 |O= 12
| Appearance = White solid
| Density =
| MeltingPtC = 110-125
| BoilingPtC =
| Solubility = <0.1 g/ml
| Solubility1 = 0.75 g/ml
| Solvent1 = Acetone
| Solubility2 = 0.5 g/ml
| Solvent2 = Toluene
| Solubility3 = <0.1 g/ml
| Solvent3 = Methanol
}}
| Section3 = {{Chembox Hazards
| HPhrases = {{H-phrases|413}}
| PPhrases = {{P-phrases|273|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Pentaerythritol tetrakis(3,5-di-''tert''-butyl-4-hydroxyhydrocinnamate)''' is a chemical compound composed of four sterically hindered [[phenol]]s linked through a [[pentaerythritol]] core. It is used as primary antioxidant for [[polymer stabilizers|stabilizing polymers]], particularly [[polyethylene]] and [[polypropylene]].
==Synthesis==
Base catalysed [[Michael addition]] of [[methyl acrylate]] to [[2,6-Di-tert-butylphenol|2,6-di-''tert''-butylphenol]]  forms the intermediate butyl-[[phloretic acid|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==
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.<ref>{{cite journal|last1=Vulic|first1=Ivan|last2=Vitarelli|first2=Giacomo|last3=Zenner|first3=John M.|title=Structure–property relationships: phenolic antioxidants with high efficiency and low colour contribution|journal=Polymer Degradation and Stability|date=January 2002|volume=78|issue=1|pages=27–34|doi=10.1016/S0141-3910(02)00115-5}}</ref>
==See also==
* [[Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate|Octadecyl 3-(3,5-di-''tert''-butyl-4-hydroxyphenyl)propionate]] - an inexpensive and commonly used polymer stabiliser
* [[Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate|Tris(3,5-di-''tert''-butyl-4-hydroxybenzyl) isocyanurate]] - a polymer stabiliser commonly used to protect against long term heat aging
* [[Irganox 1098]] - a polymer stabiliser with metal chelation properties
==References==
{{Reflist}}
[[Category:Phenol antioxidants]]