Tris(2,4-di-tert-butylphenyl)phosphite

Last updated
Tris(2,4-di-tert-butylphenyl)phosphite
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Names
Preferred IUPAC name
Tris(2,4-di-tert-butylphenyl) phosphite
Other names
  • Plastic additive 12
  • Alkanox 240
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.046.084 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 250-709-6
PubChem CID
UNII
  • InChI=1S/C42H63O3P/c1-37(2,3)28-19-22-34(31(25-28)40(10,11)12)43-46(44-35-23-20-29(38(4,5)6)26-32(35)41(13,14)15)45-36-24-21-30(39(7,8)9)27-33(36)42(16,17)18/h19-27H,1-18H3
    Key: JKIJEFPNVSHHEI-UHFFFAOYSA-N
  • CC(C)(C)C1=CC(=C(C=C1)OP(OC2=C(C=C(C=C2)C(C)(C)C)C(C)(C)C)OC3=C(C=C(C=C3)C(C)(C)C)C(C)(C)C)C(C)(C)C
Properties
C42H63O3P
Molar mass 646.937 g·mol−1
Appearancewhite solid
Melting point 181–184 °C (358–363 °F; 454–457 K)
<0.1 g/100g
Solubility in n-hexane 14 g/100g
Solubility in ethyl acetate 5 g/100g
Solubility in chloroform 58 g/100g
Solubility in toluene 40 g/100g
Solubility in methanol <0.5 g/100g
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 an antioxidant as well as other roles. The compound is a phosphite ester derived from di-tert-butylphenol. [1]

Related Research Articles

<span class="mw-page-title-main">Phosphite anion</span> Ion

A phosphite anion or phosphite in inorganic chemistry usually refers to [HPO3]2− but includes [H2PO3] ([HPO2(OH)]). These anions are the conjugate bases of phosphorous acid (H3PO3). The corresponding salts, e.g. sodium phosphite (Na2HPO3) are reducing in character.

<span class="mw-page-title-main">Steric effects</span> Geometric aspects of ions and molecules affecting their shape and reactivity

Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is generally a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape (conformation) and reactivity of ions and molecules. Steric effects complement electronic effects, which dictate the shape and reactivity of molecules. Steric repulsive forces between overlapping electron clouds result in structured groupings of molecules stabilized by the way that opposites attract and like charges repel.

<span class="mw-page-title-main">Stabilizer (chemistry)</span> Chemical used to prevent degradation

In industrial chemistry, a stabilizer or stabiliser is a chemical that is used to prevent degradation.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

<i>tert</i>-Butyllithium Chemical compound

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as solutions in hydrocarbons (such as pentane); it is not usually prepared in the laboratory.

Di-<i>tert</i>-butyl dicarbonate Chemical compound

Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These carbamate derivatives do not behave as amines, which allows certain subsequent transformations to occur that would be incompatible with the amine functional group. The Boc group can later be removed from the amine using moderately strong acids. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an orthogonal protecting group.

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

2,4-Dimethyl-6-tert-butylphenol is the organic compound with the formula Me2(tert-Bu)C6H2OH (Me = methyl, tert-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol.

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">Phosphite ester</span> Organic compound with the formula P(OR)3

In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of an unobserved tautomer phosphorous acid, H3PO3, with the simplest example being trimethylphosphite, P(OCH3)3. Some phosphites can be considered esters of the dominant tautomer of phosphorous acid (HP(O)(OH)2). The simplest representative is dimethylphosphite with the formula HP(O)(OCH3)2. Both classes of phosphites are usually colorless liquids.

Di-<i>tert</i>-butylzinc Chemical compound

Di-tert-butylzinc is a compound with the formula ZnC8H18. This compound is used as a meta activating reagent in the syntheses of N,N-dimethyl-3-iodoaniline from N,N-dimethylaniline.

<span class="mw-page-title-main">Monopotassium phosphite</span> Chemical compound

Monopotassium phosphite is an inorganic compound with the formula KH2PO3. A compositionally related compound has the formula H3PO3.2(KH2PO3). Both are white solids that consist of salts of the phosphite anion H2PO3, the conjugate base of phosphorous acid.

<span class="mw-page-title-main">Trimethylolpropane phosphite</span> Chemical compound

Trimethylolpropane phosphite, C2H5C(CH2O)3P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic.

<span class="mw-page-title-main">Triethyl phosphite</span> Chemical compound

Triethyl phosphite is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.

<i>tert</i>-Butyl hydroperoxide Chemical compound

tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, like the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, tert-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable.

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

2,6-Di-tert-butylpyridine is an organic compound with the formula (Me3C)2C5H3N. This colourless, oily liquid is derived from pyridine by replacement of the two H atoms with tert-butyl groups. It is a hindered base. For example, it can be protonated, but it does not form an adduct with boron trifluoride.

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

In organic chemistry, a tricarbonate is a compound containing the divalent −O−C(=O)−O−C(=O)−O−C(=O)−O− functional group, which consists of three carbonate groups linked in a chain by sharing of oxygen atoms. These compounds can be viewed as derivatives of a hypothetical tricarbonic acid, HO−C(=O)−O−C(=O)−O−C(=O)−OH. An important example is di-tert-butyl tricarbonate(H3C−)3C−C3O7−C(−CH3)3, an intermediate in the synthesis of di-tert-butyl dicarbonate.

The Abramov reaction is the related conversions of trialkyl to α-hydroxy phosphonates by the addition to carbonyl compounds. In terms of mechanism, the reaction involves attack of the nucleophilic phosphorus atom on the carbonyl carbon. It was named after the Russian chemist Vasilii Semenovich Abramov (1904–1968) in 1957.

<span class="mw-page-title-main">Diethyl phosphorochloridate</span> Chemical compound

Diethyl chlorophosphate is an organophosphorus compound with the formula (C2H5O)2P(O)Cl. As a reagent in organic synthesis, it is used to convert alcohols to the corresponding diethylphosphate esters. It is a colorless liquid with a fruity odor. It is a corrosive, and as a cholinesterase inhibitor, highly toxic through dermal absorption. The molecule is tetrahedral.

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

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

<i>tert</i>-Butyl nitrite Chemical compound

tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.

References

  1. Rainer Wolf; Bansi Lal Kaul (2000). "Plastics, Additives". Ullmann's Encyclopedia Of Industrial Chemistry. doi:10.1002/14356007.a20_459. ISBN   3527306730.