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

Last updated
Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
PAO-1 100.svg
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)
ChemSpider
ECHA InfoCard 100.016.560 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-216-0
PubChem CID
UNII
  • 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
AppearanceWhite 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
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H317, H319, H335, H413
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).

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a hindered phenolic antioxidant commonly used as a polymer stabiliser.

Contents

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]

Related Research Articles

<span class="mw-page-title-main">Butylated hydroxytoluene</span> Chemical compound

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

Thermal depolymerization (TDP) is the process of converting a polymer into a monomer or a mixture of monomers, by predominantly thermal means. It may be catalyzed or un-catalyzed and is distinct from other forms of depolymerization which may rely on the use of chemicals or biological action. This process is associated with an increase in entropy.

<span class="mw-page-title-main">Polymer degradation</span> Alteration in the polymer properties under the influence of environmental factors

Polymer degradation is the reduction in the physical properties of a polymer, such as strength, caused by changes in its chemical composition. Polymers and particularly plastics are subject to degradation at all stages of their product life cycle, including during their initial processing, use, disposal into the environment and recycling. The rate of this degradation varies significantly; biodegradation can take decades, whereas some industrial processes can completely decompose a polymer in hours.

<span class="mw-page-title-main">Polycarbonate</span> Family of polymers

Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worked, molded, and thermoformed. Because of these properties, polycarbonates find many applications. Polycarbonates do not have a unique resin identification code (RIC) and are identified as "Other", 7 on the RIC list. Products made from polycarbonate can contain the precursor monomer bisphenol A (BPA).

<span class="mw-page-title-main">Plasticizer</span> Substance added to a material to make it softer and more flexible

A plasticizer is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.

In industrial chemistry, a stabilizer or stabiliser is a chemical that is used to prevent degradation. Above all, heat and light stabilizers are added to plastic and rubber materials because they ensure safe processing and protect products against aging and weathering. In particular polyvinyl chloride would not be possible without stabilizers.

2,6-Di-<i>tert</i>-butylphenol Chemical compound

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

<span class="mw-page-title-main">Biodegradable plastic</span> Plastics that can be decomposed by the action of living organisms

Biodegradable plastics are plastics that can be decomposed by the action of living organisms, usually microbes, into water, carbon dioxide, and biomass. Biodegradable plastics are commonly produced with renewable raw materials, micro-organisms, petrochemicals, or combinations of all three.

<span class="mw-page-title-main">Hindered amine light stabilizers</span>

Hindered amine light stabilizers (HALS) are chemical compounds containing an amine functional group that are used as stabilizers in plastics and polymers. These compounds are typically derivatives of tetramethylpiperidine and are primarily used to protect the polymers from the effects of photo-oxidation; as opposed to other forms of polymer degradation such as ozonolysis. They are also increasingly being used as thermal stabilizers, particularly for low and moderate level of heat, however during the high temperature processing of polymers they remain less effective than traditional phenolic antioxidants.

Polymer stabilizers are chemical additives which may be added to polymeric materials to inhibit or retard their degradation. Mainly they protect plastic and rubber products against heat, oxidation, and UV light. The biggest quantity of stabilizers is used for polyvinyl chloride (PVC), as the production and processing of this type of plastic would not be possible without stabilizing chemicals. Common polymer degradation processes include oxidation, UV-damage, thermal degradation, ozonolysis, combinations thereof such as photo-oxidation, as well as reactions with catalyst residues, dyes, or impurities. All of these degrade the polymer at a chemical level, via chain scission, uncontrolled recombination and cross-linking, which adversely affects many key properties such as strength, malleability, appearance and colour.

<span class="mw-page-title-main">Photo-oxidation of polymers</span>

In polymer chemistry photo-oxidation is the degradation of a polymer surface due to the combined action of light and oxygen. It is the most significant factor in the weathering of plastics. Photo-oxidation causes the polymer chains to break, resulting in the material becoming increasingly brittle. This leads to mechanical failure and, at an advanced stage, the formation of microplastics. In textiles the process is called phototendering.

<span class="mw-page-title-main">Plastic</span> Material of a wide range of synthetic or semi-synthetic organic solids

Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be molded, extruded or pressed into solid objects of various shapes. This adaptability, plus a wide range of other properties, such as being lightweight, durable, flexible, and inexpensive to produce, has led to their widespread use. Plastics typically are made through human industrial systems. Most modern plastics are derived from fossil fuel-based chemicals like natural gas or petroleum; however, recent industrial methods use variants made from renewable materials, such as corn or cotton derivatives.

Irganox 1098 is the trade name for N,N′-(hexane-1,6-diyl)bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanamide], a primary antioxidant manufactured by BASF primarily used for stabilizing polymers, especially polyamides. It is noted for its thermal stability as well as its non-discoloring properties.

2,4,6-Tri-<i>tert</i>-butylphenol Chemical compound

2,4,6-Tri-tert-butylphenol (2,4,6-TTBP) is a phenol symmetrically substituted with three tert-butyl groups and thus strongly sterically hindered. 2,4,6-TTBP is a readily oxidizable aromatic compound and a weak acid. It oxidizes to give the deep-blue 2,4,6-tri-tert-butylphenoxy radical. 2,4,6-TTBP is related to 2,6-di-tert-butylphenol, which is widely used as an antioxidant in industrial applications. These compounds are colorless solids.

Tris(2,4-di-<i>tert</i>-butylphenyl)phosphite Chemical compound

Tris(2,4-di-tert-butylphenyl)phosphite is an organophosphorus compound with the formula [(C4H9)2C6H3O]3P. This white solid is a widely used stabilizer in polymers where it functions as a secondary antioxidant. It also reduces discoloration (yellowing) of plastics. The compound is a phosphite ester formed by the reaction of 2,4-di-tert-butylphenol with phosphorous trichloride. It is an approved food contact materials in the US.

Pentaerythritol tetrakis(3,5-di-<i>tert</i>-butyl-4-hydroxyhydrocinnamate) Chemical compound

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

<span class="mw-page-title-main">UV-328</span> Chemical compound

UV-328 is a chemical compound that belongs to the phenolic benzotriazoles. It is a UV filter that is used as an antioxidant for plastics.

1,3,5-Tris(4-(<i>tert</i>-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione Chemical compound

1,3,5-Tris(4- -3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione is a speciality antioxidant used to stabilise plastics and synthetic fibres.

Tris(3,5-di-<i>tert</i>-butyl-4-hydroxybenzyl) isocyanurate Chemical compound

Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a chemical compound used as a polymer stabilizer in plastics. Like other hindered phenols it acts as a primary antioxidant. More than 1000 tonnes per year are used in the EU.

<span class="mw-page-title-main">Bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite</span> Chemical compound

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 antioxidant such as pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate).

References

  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.