Bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite

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Bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite
P-3 100.svg
Names
Preferred IUPAC name
3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane
Other names
Trade names
  • Irgafos 126 (BASF)
  • ADK Stab PEP 24 (Adeka)
  • Ultranox 626 (SI Group)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.043.578 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 248-597-9
PubChem CID
UNII
  • InChI=1S/C33H50O6P2/c1-29(2,3)23-13-15-27(25(17-23)31(7,8)9)38-40-34-19-33(20-35-40)21-36-41(37-22-33)39-28-16-14-24(30(4,5)6)18-26(28)32(10,11)12/h13-18H,19-22H2,1-12H3
    Key: InChIKey=AIBRSVLEQRWAEG-UHFFFAOYSA-N
  • O(P1OCC2(COP(OC3=C(C(C)(C)C)C=C(C(C)(C)C)C=C3)OC2)CO1)C4=C(C(C)(C)C)C=C(C(C)(C)C)C=C4
Properties
C33H50O6P2
Molar mass 604.705 g·mol−1
AppearanceWhite solid
Density 1.166 at 20°C
Melting point 172–179 °C (342–354 °F; 445–452 K)
Boiling point 311 °C (592 °F; 584 K)
93.0 µg/L at 25°C
Hazards
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H410
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite is an organophosphite used as a polymer stabilizer in plastics. Like other phosphite antioxidants it primarily acts to remove hydroperoxides and is typically used in combination with hindered phenolic antioxidants such as pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate).

Contents

Synthesis

It is formed by a reaction between phosphorus trichloride, pentaerythritol and 2,4-di-tert-butylphenol. The poor solubility of pentererythritol can be an issue and non-nuncleophilic amines are often used to promote the reaction. [1]

Properties and applications

Compared to tris(2,4-di-tert-butylphenyl)phosphite (a common phosphite antioxidant) it has higher activity but lower stability against hydrolysis. Trace levels of amine bases are often added to commercial material to slow hydrolysis and increase storage life. [2] Its crystal structure has been determined. [3] It is comparable with a wide range of plastics including polyolefins, engineering plastics and polyurethane fibers. It is an approved food contact material in the US. [4]

References

  1. ↑ Zhu, Yuliang; Liu, Xinyue; Tang, Ying; Xu, Kexin; Tang, Xin; Zhu, Longzhi; Xiong, Biquan (13 November 2024). "Recent Advances in the Synthesis of Commercially Available Phosphite Antioxidants". ChemistryOpen: e202400135. doi: 10.1002/open.202400135 . PMC   12128154 . PMID   39538976.
  2. ↑ Papanastasiou, M.; McMahon, A.W.; Allen, N.S.; Doyle, A.M.; Johnson, B.J.; Keck-Antoine, K. (November 2006). "The hydrolysis mechanism of bis(2,4-di-tert-butyl)pentaerythritol diphosphite (Alkanox P24): An atmospheric pressure photoionisation mass spectrometric study". Polymer Degradation and Stability. 91 (11): 2675–2682. doi:10.1016/j.polymdegradstab.2006.04.023.
  3. ↑ Barren, J. P.; Bryant, G. L.; Garbauskas, M. F.; Mahood, J. A. (15 August 1995). "Bis(2,4-di-tert-butylphenyl) Pentaerythritol Diphosphite". Acta Crystallographica Section C Crystal Structure Communications. 51 (8): 1636–1639. Bibcode:1995AcCrC..51.1636B. doi:10.1107/S0108270195000965.
  4. ↑ "FDA broadens food contact approval for SI Group's Ultranox 626 antioxidant". Additives for Polymers. 2019 (9): 4. September 2019. doi:10.1016/S0306-3747(19)30174-5.
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