118-82-1

Basic information

• Product Name: 4,4'-Methylenebis(2,6-di-tert-butylphenol)
• Synonyms: 4,4'-Methylenebis(2,6-di-tert-butylphenol);TIMTEC-BB SBB007948;RARECHEM AQ BD 0024;RALOX(R) 02 S;2,2’,6,6’-tetra-tert-butyl-4,4’-methylenediphenol;4,4’-methylenebis(2,6-bis(1,1-dimethylethyl)-pheno;4,4’-methylenebis(2,6-bis(1,1-dimethylethyl)phenol);4,4’-methylenebis(2,6-di-t-butylphenol)
• CAS NO: 118-82-1
• Molecular Formula: C₂₉H₄₄O₂
• Molecular Weight: 424.66
• EINECS: 204-279-1
• Product Categories: Antioxidant;Industrial/Fine Chemicals;Organics;Diphenylmethanes (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Bisphenol and Sulfonyldiphenol Monomers;Monomers;Polymer Science
• Mol File: 118-82-1.mol

Chemical Properties

• Melting Point: 155-159 °C(lit.)
• Boiling Point: 289 °C40 mm Hg(lit.)
• Flash Point: 289°C/40mm
• Appearance: /
• Density: 0.99 g/cm3 (20℃)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.4875 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: <0.0001g/l
• PKA: 12.03±0.40(Predicted)
• Water Solubility: 31.9ng/L at 20℃
• Stability: Stable for 2 years from date of purchase as supplied. Solutions are not stable. Solutions must be made fresh and used within 1 working day.
• BRN: 1916919
• CAS DataBase Reference: 4,4'-Methylenebis(2,6-di-tert-butylphenol)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Methylenebis(2,6-di-tert-butylphenol)(118-82-1)
• EPA Substance Registry System: 4,4'-Methylenebis(2,6-di-tert-butylphenol)(118-82-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 26-36
• WGK Germany: 1
• RTECS: SL9650000
• TSCA: Yes
• Hazardous Substances Data: 118-82-1(Hazardous Substances Data)

Usage

Uses

Used in Plastic Industry:
4,4'-Methylenebis(2,6-di-tert-butylphenol) is used as an additive for plastics to enhance their stability and resistance to oxidative degradation. This helps in extending the lifespan of plastic products and maintaining their structural integrity.
Used in Rubber Industry:
In the rubber industry, 4,4'-Methylenebis(2,6-di-tert-butylphenol) is used as an additive to improve the aging resistance and durability of rubber products. It helps in preventing the rubber from cracking, hardening, or becoming brittle over time.
Used in Lubricant Industry:
4,4'-Methylenebis(2,6-di-tert-butylphenol) is used as an additive in the lubricant industry to enhance the oxidation stability of lubricating oils. This helps in reducing wear and tear on machinery and prolonging the life of the lubricants.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4'-Methylenebis(2,6-di-tert-butylphenol) is used as an antioxidant to prevent the oxidation of active pharmaceutical ingredients, ensuring their stability and efficacy.
Used in Cosmetics Industry:
4,4'-Methylenebis(2,6-di-tert-butylphenol) is used as an additive in the cosmetics industry to protect cosmetic products from oxidative degradation, ensuring their freshness and effectiveness.
Used in Food Industry:
In the food industry, 4,4'-Methylenebis(2,6-di-tert-butylphenol) is used as an additive to prevent the oxidation of fats and oils, thereby extending the shelf life of food products and maintaining their taste and quality.

Flammability and Explosibility

Nonflammable

References

1) Amorati et al. (2003), Antioxidant activity of 0-bisphenols: the role of intramolecular hydrogen bonding; J. Org. Chem. 68 5198

Synthetic route

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With proton exchanged montmorillonite In dichloromethane at 25℃; for 0.67h; Solvent; Time;	96%
Multi-step reaction with 2 steps 1: proton exchanged montmorillonite / chloroform-d1 / 0.02 h / 25 °C 2: proton exchanged montmorillonite / dichloromethane / 0.67 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: proton exchanged montmorillonite / chloroform-d1 / 0.08 h / 25 °C 2: proton exchanged montmorillonite / dichloromethane / 0.67 h / 25 °C View Scheme

formaldehyd (50-00-0) + 2,6-di-tert-butylphenol (128-39-2) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With potassium tetramethoxyborate at 130℃; for 8h; Reagent/catalyst; Temperature;	95%
With formic acid; acetic acid at 40 - 80℃; for 4h; Concentration; Temperature; Reagent/catalyst; Reflux;	90%
With potassium hydroxide In isopropyl alcohol	64%

2,6-di-tert-butylphenol (128-39-2) + 3,5-di-tert-butyl-4-hydroxybenzyl acetate (14387-17-8) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With perchloric acid In acetone	92%

4,4'-(oxybis(methylene))bis(2,6-di-tert-butylphenol) (6922-60-7) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With proton exchanged montmorillonite In dichloromethane at 25℃; for 0.67h;	87%

formaldehyd (50-00-0) + 2,6-di-tert-butylphenol (128-39-2) + acetic acid (64-19-7) → 3,5-di-tert-butyl-4-hydroxybenzyl acetate (14387-17-8) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6)

Conditions	Yield
With diethylamine for 11h; Reflux;	A 85.5% B 4% C 2.5%

benzoic acid anhydride (93-97-0) + N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine (88-27-7) → 4-hydroxy-3,5-di-tert-butylbenzyl benzoate (96506-55-7) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
In benzene for 1h; Heating;	A 85% B n/a

Coppinger's Radikal (22719-43-3, 2370-18-5) + germanium hydride trichloride (1184-65-2) → (HO((CH3)3C)2C6H2)2CHGeCl3 (153789-55-0) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran treatment od reaction mixt. in THF with HCl soln., stirring (15 min); org. phase sepn., drying over Na2SO4 (24 h), soln. concn.; identification of individual compds.;	A 80% B 20% C <1

3,5-di-tert-butyl-4-hydroxybenzyl acetate (14387-17-8) + phenol (108-95-2) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,4,6-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-phenol (6010-34-0) + 2,4-di-(4-hydroxy-3,5-di-tert-butylbenzyl)phenol (127901-01-3)

Conditions	Yield
With perchloric acid In acetone 1) heating, 2) 24 h, 20 deg C;	A 16.8% B 72% C 7.5%

Coppinger's Radikal (22719-43-3, 2370-18-5) + diphenylchlorogermane (7366-23-6) → (HO((CH3)3C)2C6H2)2CHGe(C6H5)2Cl (153789-61-8) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + dichlorodiphenylgermane (1613-66-7)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran hydrolysis (6N HCl) of reaction mixt.;	A 70% B 30% C 30%

2,6-di-tert-butylphenol (128-39-2) + N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine (88-27-7) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With dimethyl sulfate; zinc(II) chloride In chlorobenzene for 15h; Heating;	69%

2,6-di-tert-butylphenol (128-39-2) + 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one (2607-52-5) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1)

Conditions	Yield
In pentane at 30℃; Further byproducts given;	A 66% B 4% C 6% D 59%

2,6-di-tert-butylphenol (128-39-2) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1)

Conditions	Yield
With 2,6-di-tert-butylbenzoquinone methide In pentane at 30℃; Further byproducts given;	A 66% B 4% C 6% D 59%

triphenyl germyllithium (3839-32-5) + Coppinger's Radikal (22719-43-3, 2370-18-5) → (C6H5)3GeCH(C6H2(C4H9)2(OH))2 (147024-31-5) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1) + hexaphenyldigermane (2816-39-9) + chlorotriphenylgermane (1626-24-0)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran inert atmosphere; dropwise addn. of org. compd. soln. to soln. of Ge-compd. at 0°C, soln. hydrolysis by dropwise HCl addn.; soln. filtration to obtain Ph3GeGePh3, filtrate extn. (ether), drying (Na2SO4), soln. concn. (reduced pressure); (1)H-NMR spectroscopy;	A 8% B 10% C 56% D 66% E 24%

Coppinger's Radikal (22719-43-3, 2370-18-5) + dichlorophenylgermane (7366-24-7) → (HO((CH3)3C)2C6H2)2CHGe(C6H5)Cl2 (153789-58-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + trichlorophenylgermane (1074-29-9)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran reaction mixt. treatment with HCl soln. (stirring, 15 min); org. phase sepn., drying over Na2SO4, concn. (reduced pressure), chromy.;	A 60% B 20% C 20%

2,6-di-tert-butylphenol (128-39-2) + 2-(hydroxymethyl)-4-methyl-6-(1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-di-tert-butyl-4-{2-hydroxy-5-methyl-3-(1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)-benzyl}phenol

Conditions	Yield
With formic acid In chloroform for 3.5h; Reflux;	A n/a B 59%

2,6-di-tert-butylphenol (128-39-2) + 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one (2607-52-5) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1) + 4,4'-Ethylen-bis-(2,6-di-tert.-butyl-4-(3,5-di-tert.-butyl-4-hydroxy-phenyl)-cyclohexa-2,5-dienon) (98543-00-1) + 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl>-2,6-di-tert-butylcyclohexa-2,5-dien-1-one (137649-09-3)

Conditions	Yield
With triethylamine In pentane at 30℃; Product distribution; Mechanism; without Et3N, other solvent, other phenols;	A 34% B 13% C 0.4% D 1% E 9% F 53%

phthalic anhydride (85-44-9) + N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine (88-27-7) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + phthalic acid dimethylamide 4-hydroxy-3,5-di-tert-butylbenzyl ester (127900-93-0)

Conditions	Yield
In benzene for 2h; Heating;	A 47% B 49%

3,5-di-tert-butyl-4-hydroxybenzyl acetate (14387-17-8) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) + 4,4'-(oxybis(methylene))bis(2,6-di-tert-butylphenol) (6922-60-7) + 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzyl)-4-(3,5-di-tert-butyl-4-hydroxy-benzyloxymethyl)-cyclohexa-2,5-dienone (127900-98-5)

Conditions	Yield
With perchloric acid; water In acetone for 28h; Heating;	A 8% B 49% C 41% D 2%

maleic anhydride (108-31-6) + N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine (88-27-7) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + maleic acid dimethylamide 4-hydroxy-3,5-di-tert-butylbenzyl ester (127900-92-9)

Conditions	Yield
In benzene Heating;	A n/a B 42%

succinic acid anhydride (108-30-5) + N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine (88-27-7) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + succinic acid dimethylamide 4-hydroxy-3,5-di-tert-butylbenzyl ester (127900-91-8)

Conditions	Yield
In benzene Heating;	A n/a B 41%

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) + 2-pentyl-4,6-bis-trichloromethyl-[1,3,5]triazine (24481-37-6) → 2,6-di-tert-butylphenol (128-39-2) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-Di-tert-butyl-4-(4-pentyl-6-trichloromethyl-[1,3,5]triazin-2-yloxymethyl)-phenol (119294-34-7)

Conditions	Yield
With triethylamine In 1,4-dioxane at 60℃; for 4h;	A 0.55 g B 0.35 g C 38%

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) → 2,6-di-tert-butylphenol (128-39-2) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-Di-tert-butyl-4-(4-phenyl-6-trichloromethyl-[1,3,5]triazin-2-yloxymethyl)-phenol (119294-35-8)

Conditions	Yield
With 2-phenyl-4,6-bis-trichloromethyl-[1,3,5]triazine; triethylamine In 1,4-dioxane at 60℃; for 4h;	A 0.55 g B 0.35 g C 32%

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) + 2-phenyl-4,6-bis-trichloromethyl-[1,3,5]triazine (24504-22-1) → 2,6-di-tert-butylphenol (128-39-2) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-Di-tert-butyl-4-(4-phenyl-6-trichloromethyl-[1,3,5]triazin-2-yloxymethyl)-phenol (119294-35-8)

Conditions	Yield
With triethylamine In 1,4-dioxane at 60℃; for 4h;	A 0.55 g B 0.35 g C 32%

2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone (10396-80-2) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) + 4,4'-(oxybis(methylene))bis(2,6-di-tert-butylphenol) (6922-60-7) + 4-(3,5-di-t-butyl-4-hydroxybenzyloxy)-4-methyl-2,6-di-t-butylcyclohexa-2,5-dienone (83638-63-5)

Conditions	Yield
With Nafion H In 1,2-dimethoxyethane for 24h; Ambient temperature;	A 5% B 12% C 13% D 6%

dimethyl 2-methylenepentanedioate (5621-44-3) + 2,6-di-tert-butylphenol (128-39-2) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1) + dimethyl α-(3,5-di-tert-butyl-4-hydroxybenzyl)glutarate (80099-80-5)

Conditions	Yield
With lithium at 160℃; for 20h;	A 6% B 10% C 1%
With lithium at 160℃; for 20h; Yield given. Yields of byproduct given;

methanol (67-56-1) + 2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium hydroxide at 65℃; Catalytic behavior; Inert atmosphere;	A 6% B n/a C n/a

3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) + diphenylamine (122-39-4) → C72H99NO4 (1020846-09-6) + C87H121NO5 (1020846-10-9) + C102H143NO6 (1020846-11-0) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With sulfuric acid In dichloromethane; water at 40℃; for 2 - 24h; Product distribution / selectivity;	A 3% B 5% C 0.5% D n/a
With sulfuric acid In acetic acid for 10 - 24h; Product distribution / selectivity;	A 1% B 1% C 1% D n/a

formaldehyd (50-00-0) + 2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-ethoxymethylphenol (3080-84-0) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1)

Conditions	Yield
With potassium hydroxide

methyl 3-methoxypropionate (3852-09-3) + 2,6-di-tert-butylphenol (128-39-2) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1) + dimethyl α-(3,5-di-tert-butyl-4-hydroxybenzyl)glutarate (80099-80-5) + 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,4,6-trimethoxycarbonylhexane (95683-83-3) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 160℃; for 5h; Product distribution; various bases, time, solvents;

C29H43O2 (14306-91-3) → 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1)

Conditions	Yield
Rate constant; Thermodynamic data; rate constant of the disproportionation;

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) → 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1)

Conditions	Yield
With chloranil In toluene at 110℃; for 2h;	A 90% B 92%

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + phenylborondichloride (873-51-8) → bis(3,5-di-tert-butyl-4-(hydrogenphenylboronoxy)phenyl)methane (1037069-96-7)

Conditions	Yield
With n-butyllithium In hexane; toluene byproducts: LiCl; n-C4H9Li in hexane was added dropwise to a soln. of phenol-compound in toluene in N2 atm., the mixt. was heated at 100°C overnight, cooled to room temp., Cl2BC6H5 was added, heated for 12 h; ppt. was dissolved washing with water, dried over MgSO4, the solvent wasremoved in vac.; elem. anal.;	84%

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one (2607-52-5) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1) + 3,3',5,5'-tetra-tert-butyl-4,4'-stilbenequinone (809-73-4) + 2,6-Di-tert-butyl-4,4-bis-(3,5-di-tert-butyl-4-hydroxy-benzyl)-cyclohexa-2,5-dienone (62078-82-4)

Conditions	Yield
With triethylamine In pentane at 30℃;	A 72% B 31% C 9% D 11%

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) → 2,4,10,12-tetra-t-butyl-14,15-dioxadispiro<5,1,5,2>-pentadeca-1,4,9,12-tetraene-3,11-dione (74854-03-8)

Conditions	Yield
With air; silver(l) oxide In benzene for 8h;	72%

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) → 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone (4359-97-1)

Conditions	Yield
With chloranil In toluene for 2h; Reflux;	70%
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: aq.-ethanolic NaOH View Scheme

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + epichlorohydrin (106-89-8) → 4,4’-methylenebis(2,6-di-tert-butylphenol) diglycidyl ether (860376-70-1)

Conditions	Yield
Stage #1: 4,4'-Methylenebis(2,6-di-tert-butylphenol) With sodium tert-pentoxide In N,N-dimethyl-formamide at -10 - -5℃; for 0.5h; Stage #2: epichlorohydrin In N,N-dimethyl-formamide at -10 - 82℃; for 16h;	60%

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one (2607-52-5) → 1,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (1516-94-5) + 2,6-Di-tert-butyl-4,4-bis-(3,5-di-tert-butyl-4-hydroxy-benzyl)-cyclohexa-2,5-dienone (62078-82-4)

Conditions	Yield
In dimethyl sulfoxide at 30℃;	A 15% B 55%

tetrahydrofuran (109-99-9) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) → C53H90Br2Mg2O8

Conditions	Yield
With 2-mesitylmagnesium bromide In toluene for 12h; Inert atmosphere;	47.1%

4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + methyl iodide (74-88-4) → bis(3,5-di-tert-butyl-4-methoxyphenyl)methane (32465-70-6)

Conditions	Yield
With sodium hydride	36%

Upstream product

• 3852-09-3 methyl 3-methoxypropionate 
• 128-39-2 2,6-di-tert-butylphenol 
• 14387-17-8 3,5-di-tert-butyl-4-hydroxybenzyl acetate 
• 2607-52-5 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadien-1-one 
• 93-97-0 benzoic acid anhydride 
• 88-27-7 N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)amine 
• 292638-85-8 acrylic acid methyl ester 
• 22719-43-3 Coppinger's Radikal 
• 1184-65-2 germanium hydride trichloride 
• 6922-60-7 4,4'-(oxybis(methylene))bis(2,6-di-tert-butylphenol) 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 
• 88-26-6 3,5-di-tert-butyl-4-hydroxybenzyl alcohol 
• 108-30-5 succinic acid anhydride 
• 108-31-6 maleic anhydride 

Downstream Products

• 2455-14-3 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 
• 15052-28-5 2,6-di-tert-butyl-1,4-benzoquinone monooxime 
• 153789-59-4 (HO((CH₃)3C)2C₆H₂)CH₂C₆H₂(C(CH₃)3)2OGe(C₆H₅)Cl₂ 
• 1037069-96-7 bis(3,5-di-tert-butyl-4-(hydrogenphenylboronoxy)phenyl)methane 
• 1879-09-0 2,4-dimethyl-6-tert-butylphenol 
• 103330-88-7 bis-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methoxy-methane 
• 4359-97-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone 
• 14306-91-3 C₂₉H₄₃O₂ 
• 83047-44-3 2,6,2',6'-tetra-tert-butyl-4,4'-dimethoxy-4,4'-methanediyl-bis-cyclohexa-2,5-dienone 
• 79965-38-1 bromo-bis-(3,5-di-tert-butyl-4-hydroxy-phenyl)-methane 
• 32465-70-6 bis(3,5-di-tert-butyl-4-methoxyphenyl)methane 
• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 

Relevant articles and documents

Practical process for the air oxidation of cresols: Part A. Mechanistic investigations

The catalytic air oxidation of p-cresol and 2,6-di-tert-butyl-4- methylphenol to the corresponding benzaldehydes was investigated to determine the mechanism at work in these oxidation reactions. A number of intermediates and byproducts, mainly in the form of dimers, were observed during the course of the reactions, and their structures were elucidated by spectroscopic and chromatographic methods. The existence of these compounds in the reaction mixtures, and their proposed methods of formation, provided further insight into the mechanism involved in these oxidations.

Synthesis of unsymmetrical hydroxybenzylphenols from 2-isobornyl-4-methylphenol

2-Hydroxymethyl-6-isobornyl-4-methylphenol was synthesized from 2-isobornyl-4-methylphenol. Reactions of this hydroxymethyl derivative with 2,4- and 2,4-di-tert-butylphenols gave new unsymmetrical hydroxybenzylphenols.

Thermal decomposition of 2,6-di-tert-butyl-4-dimethylaminomethylphenol

Products of thermolysis of 2,6-di-tert-butyl-4-dimethylaminomethylphenol were determined qualitatively and quantitatively by GLC, UV, and 1H NMR methods. The kinetics of the reaction was studied. The thermolysis products were studied as the inhibitors in thermopolymerization of monomers.

Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media

We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density functional theory calculations support a plausible mechanism, which includes a distinctive aromatic C[sbnd]C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.

Phenolic compound as well as preparation method and application thereof

The invention provides a phenolic compound as well as a preparation method and application thereof. The structure of the phenolic compound is shown as a general formula (I), R1 and R1'can be the sameor different and are independently selected from CnH(2n+m), n is an integer ranging from 3 to 30, m is 1, -1, -3 or -5, R2 and R2' can be the same or different and are independently selected from C1-C8 straight chain or branched chain alkyl respectively; and R3 is selected from C1-C6 straight chain or branched chain alkylene. The phenolic compound provided by the invention has very excellent oxidation resistance, and can be used as an antioxidant in lubricating oil, lubricating grease, fuel oil, plastic and rubber. The preparation method disclosed by the invention is simple and feasible, and the yield and product purity are relatively high.

Phenolic derivative as well as preparation method and application thereof

The invention provides a phenol derivative as well as a preparation method and application thereof. The structure of the phenolic derivative is shown as a formula (I), wherein the definition of each group is shown in the specification. The phenolic derivative can be used as an antioxidant in lubricating oil, lubricating grease, plastics and rubber, and can also be used as base oil of lubricating oil and lubricating grease, and an anti-wear agent of lubricating oil and lubricating grease. The phenolic derivative disclosed by the invention has excellent oxidation resistance, lubricating property, antifriction property, viscosity-temperature property and low-temperature property.

Antioxidant 1425 production process

Antioxidant 1425 is an important chemical industry product. The basic process comprises a benzylation reaction, an alkaline hydrolysis reaction, and a complexing reaction. The production process comprises: pouring distillation kettle residue loaded into a barrel into a 2000 L enamel reaction kettle, maintaining a certain temperature (95-100 DEG C), slowly adding a prepared 2-5% sodium hydroxide solution according to a ratio of 1:1.1 under stirring, stirring for 2 h, carrying out standing layering, neutralizing the lower layer water phase, transferring into an antioxidant 1425 complexing kettle, mixing with the hydrolyzate in the production, extracting with solvent oil, recovering the small amount of the antioxidant 1425, and carrying out drying crystallization on the upper layer organic phase to obtain the product antioxidant 4426 product, wherein the main components of the dried waste gas are water vapor and a small amount of non-methane total hydrocarbons, and are subjected to unorganized emission.

Iridium-Catalyzed C4-Alkylation of 2,6-Di-tert-butylphenol by Using Hydrogen-Borrowing Catalysis

An iridium-catalyzed hydrogen-borrowing process has been developed whereby 2,6-di-tert-butylphenol can be alkylated at the C4-position by using a range of primary alcohols (11 examples, 40-93% yield). Following this, a selection of the products obtained underwent retro-Friedel-Crafts reactions to provide para-substituted phenols, which could potentially undergo further synthetic manipulations.

Based on mixed alkali catalyst catalytic double-phenolic antioxidant preparation method and application (by machine translation)

The invention discloses a mixed alkali catalyst based on double-phenol method for preparing an antioxidant and application. The preparation method comprises: the two alkyl substituted phenol and aldehyde compound is placed in the closed and in the reactor and in a mixed alkali catalyst can choose to add or not to add the presence of an organic solvent of the reaction is carried out under the condition of, and in the after the reaction is finished after processing the obtained compound antioxidant product double phenol apperception, the anti-oxidant product can be used for preparing the lubricating oil composition, composition or burns the oil line as plastic, rubber, such as anti-aging agent. Antioxidant bisphenol compounds of this invention for the production of simple operation, mild conditions, such as the sources of raw materials and catalyst of extensive and is cheap and easy to obtain, the reaction cycle is short, it is easy to control, process with high safety, low energy consumption in the producing process, the yield of the product and high purity, and can effectively control and reducing pollutant emissions, is a safe and energy-saving, environmental protection art. (by machine translation)

Preparation method for hindered bisphenol type antioxidant

The invention relates to a preparation method for a hindered bisphenol type antioxidant. The preparation method comprises the following process steps: adding 2,6-ditert-butyl phenol and a catalyst into a reaction vessel, wherein per 1 mol of 2,6-ditert-butyl phenol is added with 3 to 8 mL of the catalyst; carrying out stirring under the temperature condition of 40 to 60 DEG C until the mixture is melted; adding a formaldehyde solution, wherein a mol ratio of formaldehyde and 2,6-ditert-butyl phenol is 1: (2.0-2.2); after the completion of addition, carrying out heating to 60 to 80 DEG C, carrying out reaction for 2 to 5 hours, then carrying out pumping filtration, and carrying out washing by using warm water with a temperature of 40 to 50 DEG C; subjecting an obtained filter cake to vacuum drying, and recrystallizing an obtained crude product, wherein per 1 g of the crude product is added with 0.5 to 5 mL of a recrystallization solvent; and carrying out vacuum drying so as to obtain a yellow needle-like crystal. The method provided by the invention does not need adding alcohol organic solvents in the preparation process, has the advantages of simple production process, low cost, few by-products in a preparation process, and high antioxidant purity and yield, and is beneficial for environmental protection.