87-97-8

Usage

Uses

Used in Plastics Industry:
2,6-di-tert-butyl-4-(methoxymethyl)phenol is used as an antioxidant for preventing the oxidative degradation of plastics, thereby enhancing their stability and extending their service life.
Used in Rubber Industry:
In the rubber industry, 2,6-di-tert-butyl-4-(methoxymethyl)phenol is used as a stabilizing agent to protect rubber materials from oxidative damage, which can cause deterioration and loss of mechanical properties.
Used in Petroleum Products:
2,6-di-tert-butyl-4-(methoxymethyl)phenol is used as an additive in petroleum products to inhibit oxidation, which can lead to the formation of harmful byproducts and reduce the quality of the products.

InChI:InChI=1/C16H26O2/c1-15(2,3)12-8-11(10-18-7)9-13(14(12)17)16(4,5)6/h8-9,17H,10H2,1-7H3

Upstream product

• 50-00-0 formaldehyd 
• 128-39-2 2,6-di-tert-butylphenol 
• 67-56-1 methanol 
• 14387-17-8 3,5-di-tert-butyl-4-hydroxybenzyl acetate 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 2179-51-3 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one 
• 20357-53-3 2,6-Bis--4-methoxymethyl-phenoxyl 
• 2607-52-5 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one 
• 131544-10-0 3,3',5,5'-tetra-tert-butyl-1,1'-dimethyl-[1,1'-bi(cyclohexane)]-2,2',5,5'-tetraene-4,4'-dione 
• 120-72-9 indole 
• 19487-11-7 2,6-di-tert-butyl-4-chloro-4-methylcyclohexa-2,5-dien-1-one 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 

Downstream Products

• 980-17-6 diisopropyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate 
• 127412-24-2 diisobutyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate 
• 899-89-8 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid dimethyl ester 
• 56856-08-7 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-3,3-dimethyl-2-butanone 
• 938174-16-4 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-(4-chlorophenyl)-2-methyl-propan-1-one 
• 938174-15-3 1-[{3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl}methyl]cyclopentanecarboxaldehyde 
• 938174-32-4 2,2-bis[{3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl}methyl]-1-(4-chlorophenyl)propan-1-one 
• 938174-28-8 2,2-bis[{3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl}methyl]indan-1-one 
• 56189-68-5 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2-dimethyl-propionaldehyde 
• 56856-06-5 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-3-methyl-2-butanone 
• 56106-45-7 1-[{3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl}methyl]cyclohexanecarboxaldehyde 

Relevant academic research and scientific papers

Bifunctional compound and synthesis method thereof, and applications of bifunctional compound as antioxidant

The invention discloses a bifunctional compound and a synthesis method thereof, and applications of the bifunctional compound as an antioxidant, wherein the bifunctional compound comprises a hinderedphenol unit, a phosphite unit, a trimethylbenzene unit and a straight-chain segment unit. According to the invention, the synergistic effect of the hindered phenol unit and the phosphite unit and thecontent of the effective functional groups in unit mass are adjusted by controlling the length of the straight-chain segment unit, and the trimethylbenzene structure is beneficial to preventing the antioxidant compound from being precipitated out of the polymer; and the compound can be used as an antioxidant of polypropylene or polyethylene.

Highly selective conversion of guaiacol to: Tert -butylphenols in supercritical ethanol over a H2WO4 catalyst

The conversion of guaiacol is examined at 300 °C in supercritical ethanol over a H2WO4 catalyst. Guaiacol is consumed completely, meanwhile, 16.7% aromatic ethers and 80.0% alkylphenols are obtained. Interestingly, tert-butylphenols are produced mainly with a high selectivity of 71.8%, and the overall selectivity of 2,6-di-tert-butylphenol and 2,6-di-tert-butyl-4-ethylphenol is as high as 63.7%. The experimental results indicate that catechol and 2-ethoxyphenol are the intermediates. Meanwhile, the WO3 sites play an important role in the conversion of guaiacol and the Br?nsted acid sites on H2WO4 enhance the conversion and favour a high selectivity of the tert-butylphenols. The recycling tests show that the carbon deposition on the catalyst surface, the dehydration and partial reduction of the catalyst itself are responsible for the decay of the H2WO4 catalyst. Finally, the possible reaction pathways proposed involve the transetherification process and the alkylation process during guaiacol conversion.

Novel method for synthesizing antioxidant 330 by catalyst

The invention aims at providing a method for synthesizing an antioxidant 330. Manganese dioxide-titanium dioxide-molecular sieve loaded phosphoric acid and ferroferric oxide-molecular sieve loaded phosphoric acid catalysts are prepared; under the existence of manganese dioxide-titanium dioxide-molecular sieve loaded phosphoric acid catalysts, 2,6-butylated hydroxytoluene and methyl alcohol are used as preparation raw materials to synthesize 3,5-di-tert-4-hydroxybenzyl ether; the methyl alcohol is used as preparation raw materials to synthesize 3,5-di-tert-4-hydroxybenzyl ether; next, under theexistence of the iron oxide-molecular sieve loaded phosphoric acid catalysts, the 3,5-di-tert-4-hydroxybenzyl ether and mesitylene react to obtain the antioxidant 330. The yield of the synthesized antioxidant is high; the purity is high.

Antiradical activity of benzazole-2-thiones

Reaction of benzoxazole-2-thione with 3,5-di-tert-butyl-4-hydroxybenzylacetate in methanol affords S-(3,5-di-tert-butyl-4-hydroxybenzyl)-2-mercaptobenzoxazole as the major product. Antiradical activity of S- and N-3,5-di-tert-butyl-4-hydroxybenzyl derivatives of benzothiazole(oxazole, imidazole)-2-thione with respect to 2,2-diphenyl-1-picrylhydrazyl is varies widely. S-Benzyl derivatives exhibit higher reactivity at 30°C.

Solvolysis of 4-halogeno-4-alkyl-2,6-di-tert-butylcyclohexa-2,5-dienones induced by positive halogen donors as electrophiles

Positive halogen donors such as N-iodosuccinimide (NIS) induce solvolysis of dienones 1, as model 4-halogenocyclohexa-2,5-dienones, in different hydroxylic solvents (ROH), yielding the 4-RO-cyclohexa-2,5-dienones (2). The rate of the solvolysis with NIS is highly dependent on the structure of ROH. The problem of such dependency is overcome by running the reaction in ROH diluted with MeCN, a polar aprotic solvent, in place of pure ROH; the rate of the reaction in the ROH-MeCN solvent mixture is almost independent of the structure (or the polarity) of ROH, and the reaction is completed faster or markedly faster than in neat ROH. The results suggest that the solvolysis rate is controlled by the polarity of the solvent system, although the hydrogen-bond acceptability of MeCN for dilution also accelerates the reaction. A mechanism for the solvolysis is proposed, involving electrophilic attack of a positive halogen donor at the halogen atom of 1, generating the 4-oxocyclohexa-2,5-dienyl cation intermediates (8) via the rate-limiting polar transition states. CSIRO 2013.

Synthesis and oxidizing ability of p-chloranil dimer

A p-chloranil dimer ( pCh2) has been synthesized. The first reduction potential of pCh2 shifted to a more positive value than that observed for the p-chloranil monomer ( pCh1) and was more negative than that for 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). As expected, pCh2 oxidized 9,10-dihydroanthracene and α-tetralol to give anthracene and α-tetralone, respectively, more efficiently than pCh1 did. The advantages of pCh2 were observed in oxidations of 2,4-di-tert-butylphenol and 2,6-di-tertbutyl- 4-methylphenol. Although further oxidation took place in DDQ oxidations and no reaction occurred in pCh1 oxidations, initial oxidation products were solely obtained in pCh2 oxidation because of its moderate oxidizing ability.

Single crystal X-ray structure of 2,6-di-tert-butyl-4-(3-(4-chlorophenyl)- 4-methyl-4,5-dihydroisoxazol-5-yl)phenol 1,4-dioxane hemisolvate

The title compound (2,6-di-tert-butyl-4-(3-(4-chlorophenyl)-4-methyl-4,5- dihydroisoxazol-5-yl)phenol is synthesized and studied by the single crystal X-ray diffraction method. The structure of the product was confirmed by IR, 1H and 13C NMR spectroscopy. The crystal structure of 1,4-dioxane hemisolvate of the product is solved in the monoclinic space group P21/c with a = 17.713(6) A, b = 9.529(3) A, c = 13.972(4) A, β = 94.09(4), V = 2352.3(13) A3, Z = 4, T = 120(2) K.

Synthesis of new substituted 2,2-bis-(3,5-di-t-butyl-4-hydroxybenzyl) benzocycloalkanones, bromopropiophenones, and their alcohol analogs

A new series of substituted 2,2-bis-(3,5-di-t-butyl-4-hydroxybenzyl) benzocycloalkanones, bromopropiophenones, and their alcohol analogs were synthesized. The corresponding alcohols may act as potential allosteric modulators of GABAB receptors. TUeBITAK.

Electron transfer between protonated and unprotonated phenoxyl radicals

(Chemical Equation Presented) The reaction of phenoxyl radicals with acids is investigated. 2,4,6-Tri-tert-butylphenoxyl radical (13), a persistent radical, deteriorates in MeOH/PhH in the presence of an acid yielding 4-methoxycyclohexa-2,5-dienone 18a and the parent phenol (14). The reaction is facilitated by a strong acid. Treatment of 2,6-di-tert-butyl-4-methylphenoxyl radical (2), a short-lived radical, generated by dissociation of its dimer, with an acid in MeOH provides 4-methoxycyclohexa-2,5-dienone 4 and the products from disproportionation of 2 including the parent phenol (3). A strong acid in a high concentration favors the formation of 4 while the yield of 3 is always kept high. Oxidation of the parent phenol (33) with PbO2 to generate transient 2,6-di-tert-butylphenoxyl radical (35) in AcOH/H2O containing an added acid provides eventually p-benzoquinone 39 and 4,4′-diphenoquinone 42, the product from dimerization of 35. A strong acid in a high concentration favors the formation of 39. These results suggest that a phenoxyl radical is protonated by an acid and electron transfer takes place from another phenoxyl radical to the protonated phenoxyl radical, thus generating the phenoxyl cation, which can add an oxygen nucleophile, and the phenol (eq 5). The electron transfer is a fast reaction.

Synthesis of sterically hindered phenolic compounds from indole and its derivatives

Reactions of 3,5-di-tert-butyl-4-hydroxybenzyl acetate with indole and its derivatives gave a series of sterically hindered phenolic compounds having various functional groups. The products are potentially capable of inhibiting radical chain oxidation processes according to different mechanisms.