1948-33-0

Basic information

• Product Name: tert-Butylhydroquinone
• Synonyms: 1-T-BUTYL-1,4-DIHYDROXYBENZENE;2-(1,1-Dimethylethyl)-1,4-benzenediol;2-tert-butylhydroquinone;2-TERT-BUTYL-1,4-BENZENEDIOL;2-TERT-BUTYL-1,4-DIHYDROXYBENZENE;2-T-BUTYLHYDROQUINONE;Butylhydroquinone;TERTIARY BUTYL HYDROQUINONE
• CAS NO: 1948-33-0
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• EINECS: 217-752-2
• Product Categories: Industrial/Fine Chemicals;Anthraquinones, Hydroquinones and Quinones;Alcohols;Monomers;Polymer Science;Organic Building Blocks;Oxygen Compounds;Polyols;Isoxazoles ,Oxazoles
• Mol File: 1948-33-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Boiling Point: 295 °C
• Flash Point: 171 °C
• Appearance: White to light tan, may contain black specs/Crystalline Powder
• Density: 295
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.4859 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.80±0.18(Predicted)
• Water Solubility: Slightly soluble in water(10g/L).
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 637923
• CAS DataBase Reference: tert-Butylhydroquinone(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butylhydroquinone(1948-33-0)
• EPA Substance Registry System: tert-Butylhydroquinone(1948-33-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-28A
• RIDADR: UN3077
• WGK Germany: 3
• RTECS: MX4375000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 1948-33-0(Hazardous Substances Data)

Usage

Chemical Properties

White, crystalline solid having a characteristic odour. tert-Butylhydroquinone (TBHQ) is an antioxidant used to preserve oils, fats and food items. It is found in vegetable oils and animal fats, varnishes, lacquers, resins, oils field additives, and perfumes.In low concentrations it shows cytoprotective qualities while at higher concentrations it exhibits cytotoxic behavior. TBHQ was used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli.Environment friendly electrode materials for supercapacitors were attained by decorating the surface of graphene nanosheets with TBHQ.

Uses

Different sources of media describe the Uses of 1948-33-0 differently. You can refer to the following data:
1. tert-Butylhydroquinone (TBHQ) is an antioxidant that exhibits an excellent stabilizing effect in unsaturated fats and oils. It has good solubility in fats and oils, with a maximum usage level of 0.02% based on the weight of the fat or oil or the fat content of the food product. It shows no discoloration in the presence of iron and produces no discernible flavor or odor. It can be combined with BHA and BHT. It is used in edible fats and vegetable oils to retard rancidity. It is used in potato chips and dry cereal. It is also termed butylhydroquinone and mono-tertiary-butylhydroquinone.
2. antioxidant in cosmetic products like lipsticks.
3. TBHQ was used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli. Environment friendly electrode materials for supercapacitors were attained by decorating the surface of graphene nanosheets with TBHQ. TBHQ is frequently used as a food preservative. Inhibition of oxidative rancidity in frozen cooked fish flakes by tert-butylhydroquinone. Nuclear factor E2-related factor 2-dependent antioxidant response element activation is by tert-butylhydroquinoneoccurring preferentially in Astrocytes conditions.

Definition

ChEBI: A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.

General Description

White to light tan crystalline powder or a fine beige powder. Very slight aromatic odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, such as tert-Butylhydroquinone, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. tert-Butylhydroquinone is incompatible with oxidizers.

Fire Hazard

tert-Butylhydroquinone is combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

This antioxidant has seldom been reported as a sensitizer, mainly in cosmetics (lipsticks, lip-gloss, hair dyes) or in cutting oils. Simultaneous/cross-reactions have been described to butylhydroxyanisole (BHA) and less frequently to butylhydroxytoluene (BHT), but not to hydroquinone

Purification Methods

Recrystallise the hydroquinone from H2O or MeOH and dry it in a vacuum at 70o. Store it in a dark container. [Stroh et al. Angew Chem 69 699 1957, Beilstein 6 IV 6013.]

InChI:InChI=1/C10H12O3/c1-10(2,3)8-6(11)4-5-7(12)9(8)13/h4-5,13H,1-3H3

Synthetic route

hydroquinone (123-31-9) + tert-butyl alcohol (75-65-0) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With phosphoric acid In water at 59 - 81℃; for 2h; Temperature;	99.9%
With aminosulfonic acid In 1,4-dioxane; toluene at 135℃; for 8h; Temperature;	50%
With phosphoric acid In water at 80℃; for 4h; Concentration; Temperature; Time; Large scale;	44.8%

acetic acid tert-butyl ester (540-88-5) + hydroquinone (123-31-9) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With sulfuric acid at 85℃; for 8h; Temperature; Large scale;	99.9%

2-tert-butyl-1,4-benzoquinone (3602-55-9) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With (iPr4PCP)IrH4; hydrogen In toluene at 60℃; under 760.051 Torr; for 2h;	99%
With palladium on activated charcoal; hydrogen In dichloromethane at 60℃; under 22502.3 Torr; for 2h; Temperature; Solvent; Pressure; Reagent/catalyst;	97.3%
With 2,5-dihydrotoluene; trifluoroacetic acid In toluene at 30℃; for 2h;	70%

2-tert-Butylphenol (88-18-6) → 2-tert-butyl-1,4-benzoquinone (3602-55-9) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With dihydrogen peroxide; Ti-superoxide In water; acetic acid at 50 - 60℃; for 1.25h; Product distribution / selectivity;	A 97% B 0.7%

2-tert-butyl-4-hydroxybenzaldehyde → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 35℃; for 12h; Dakin Phenol Oxidation;	70%

2-tert-butyl-1,4-benzoquinone (3602-55-9) + benzylamine (100-46-9) → tert-butylhydroquinone (1948-33-0) + 2-(Benzylamino)-5-(tert-butyl)1,4-benzoquinone + 2-(Benzylamino)-6-(tert-butyl)-1,4-benzoquinone

Conditions	Yield
With oxygen In acetonitrile for 1h; Ambient temperature;	A 15.6% B 18.8% C 65.6%

hydroquinone (123-31-9) + tert-butyl alcohol (75-65-0) → 2,5-di-tert-butylphenol (5875-45-6) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With aminosulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4h; Temperature; Solvent;	A 17.2% B 57.8%

2-tert-butyl-1,4-benzoquinone (3602-55-9) → tert-butylhydroquinone (1948-33-0) + 2-(Benzylamino)-5-(tert-butyl)1,4-benzoquinone + 2-(Benzylamino)-6-(tert-butyl)-1,4-benzoquinone

Conditions	Yield
With benzylamine In acetonitrile for 1h; Ambient temperature;	A 52.8% B 6.6% C 40.6%

hydroquinone (123-31-9) + tert-butyl alcohol (75-65-0) → t-butyl phenyl ether (6669-13-2) + 2,5-di-tert-butyl-p-benzoquinone (2460-77-7) + 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol (88-58-4) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With porous pillared-zirconium phosphate functionalized with methyl group In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4h; Reagent/catalyst; Autoclave;	A n/a B n/a C n/a D 48.8%
With perfluorosulfonicacid-functionalized carbon nanotubes (PFSA-CNT-0.5) In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Catalytic behavior; Reagent/catalyst; Autoclave;

hydroquinone (123-31-9) + isobutene (115-11-7) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With phosphoric acid; xylene at 105℃;
With aluminum oxide; silica gel; xylene at 200℃;
With aluminium tris-<4-hydroxy-phenolate>; xylene at 240℃;

t-butyl bromide (507-19-7) + hydroquinone (123-31-9) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
silica gel In dichloromethane at 30℃; for 24h; Product distribution;

2-tert-butylsemiquinone radical (66806-57-3) → 2-tert-butyl-1,4-benzoquinone (3602-55-9) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
In water at 22℃; Equilibrium constant; Rate constant; Irradiation;

hydroquinone (123-31-9) + isobutene (115-11-7) → 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol (88-58-4) + 2-t-Butyl-4-t-butoxyphenol (2467-52-9) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With Amberlyst IR120 H(1+) In diethyl ether Ambient temperature;

2-tert-butylsemiquinone radical anion → 2-tert-butyl-1,4-benzoquinone (3602-55-9) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
In water at 22℃; Rate constant;

1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) → 2-tert-butyl-1,4-benzoquinone (3602-55-9) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With ruthenium trichloride In water; acetonitrile Oxidation; Hydrolysis; Electrochemical reaction;

3-tert-Butyl-4-hydroxyanisole (121-00-6) + 3-tert-butyl-4-methoxyphenol (88-32-4) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With formic acid at 25℃; for 336 - 3696h; Conversion of starting material;
With formic acid for 24h; Heating / reflux;

5-tert-butyl-1,2,4-trihydroxybenzene (4857-74-3) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal

1,2,4-Trihydroxybenzene (533-73-3) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Acidic conditions 2: hydrogen / palladium on activated charcoal View Scheme

tert-butyl methyl ether (1634-04-4) + hydroquinone (123-31-9) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With 3-(4-sulfobutylamino)propylsilanized MCM-41 In nitrobenzene at 150℃; for 0.166667h; Catalytic behavior; Temperature; Solvent; Time; Friedel-Crafts Alkylation; Microwave irradiation; Green chemistry; chemoselective reaction;

tert-butyl methyl ether (1634-04-4) + hydroquinone (123-31-9) → 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With 3-(4-sulfobutylamino)propylsilanized MCM-41 In nitrobenzene at 165℃; for 0.166667h; Friedel-Crafts Alkylation; Microwave irradiation; Green chemistry; chemoselective reaction;

tert-butyl methyl ether (1634-04-4) + hydroquinone (123-31-9) → 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol (88-58-4) + 4-(tert-butoxy)phenol (2460-87-9) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With 3-(4-sulfobutylamino)propylsilanized MCM-41 In nitrobenzene at 150℃; for 0.133333h; Catalytic behavior; Concentration; Friedel-Crafts Alkylation; Microwave irradiation; Green chemistry; chemoselective reaction;

1,4-O-di-propanoyl-t-butylhydroquinone (90784-13-7) → tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With Candida antarctica lipase B In di-isopropyl ether; isopropyl alcohol at 45℃; Enzymatic reaction; regioselective reaction;

hydroquinone (123-31-9) + tert-butyl alcohol (75-65-0) → 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol (88-58-4) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With phosphoric acid In toluene at 70 - 105℃;

2-tert-butyl-1,4-benzoquinone (3602-55-9) + [PdI(μ-4,5-diazafluoren-9-one)(acetato)]2 → 4,5-Diazafluoren-9-one (50890-67-0) + palladium diacetate (3375-31-3) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
With acetic acid In 1,4-dioxane; tetradeuterioacetic acid at 20℃; for 24h; Equilibrium constant; Inert atmosphere; Glovebox;

[(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)Pd(η2-2-tert-butyl-1,4-benzoquinone)] + acetic acid (64-19-7) → (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)palladium(II) acetate (152506-88-2) + tert-butylhydroquinone (1948-33-0)

Conditions	Yield
In chloroform-d1; tetradeuterioacetic acid at 20℃; for 16h; Equilibrium constant; Inert atmosphere; Glovebox;

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) + tert-butylhydroquinone (1948-33-0) → 2-tert-butyl-4-thexyldimethylsilanyloxyphenol (943790-10-1)

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide at 20℃; for 7h;	100%

tert-butylhydroquinone (1948-33-0) → 2-tert-butyl-1,4-benzoquinone (3602-55-9)

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 0.25h; Ambient temperature;	99%
With tetra(n-butyl)ammonium dichromate(VI) In dichloromethane for 0.15h; Reflux;	99%
With [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6; dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 0.0833333h;	99%

tert-butylhydroquinone (1948-33-0) + methyl iodide (74-88-4) → 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 2h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	88%
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 4h; Inert atmosphere;	83%
Stage #1: tert-butylhydroquinone With sodium hydride In dimethyl sulfoxide for 0.5h; Metallation; Stage #2: methyl iodide In dimethyl sulfoxide Methylation;	60%

acetic anhydride (108-24-7) + tert-butylhydroquinone (1948-33-0) → 4-acetoxy-2-tert-butylphenol (717-47-5)

Conditions	Yield
With pyridine at 85℃; for 10h;	98%

pivaloyl chloride (3282-30-2) + tert-butylhydroquinone (1948-33-0) → 2-tert-butyl-4-pivaloyloxyphenol (66549-79-9)

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane at 0℃; for 4h; Acylation;	97%
With 1H-imidazole; dmap In dichloromethane at 0 - 4℃; for 18h; Inert atmosphere;	97%

triisopropylsilyl chloride (13154-24-0) + tert-butylhydroquinone (1948-33-0) → 2-(1,1-dimethylethyl)-4-(triisopropylsilyloxy)phenol (155135-23-2)

Conditions	Yield
With 1H-imidazole; dmap	96%
With 1H-imidazole; dmap In dichloromethane Inert atmosphere;	90%
With 1H-imidazole; dmap In dichloromethane for 15h; Ambient temperature;	88%

di-tert-butyl dicarbonate (24424-99-5) + tert-butylhydroquinone (1948-33-0) → carbonic acid tert-butyl ester 3-tert-butyl-4-hydroxy-phenyl ester

Conditions	Yield
With 6,7-dimethoxyisoquinoline In dichloromethane at 20℃; for 10h; Inert atmosphere; chemoselective reaction;	95%

p-Toluic acid (99-94-5) + tert-butylhydroquinone (1948-33-0) → 3-(tert-butyl)-4-hydroxyphenyl 4-methylbenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	94%

vinyl propionate (105-38-4) + tert-butylhydroquinone (1948-33-0) → 4-O-propanoyl-2-t-butylhydroquinone

Conditions	Yield
With Candida antarctica lipase B In di-isopropyl ether at 45℃; for 24h;	93.3%
With lipase B from Candida antarctica, immobilized form In di-isopropyl ether at 45℃; for 72h; Enzymatic reaction; regioselective reaction;

Bromoacetaldehyde diethyl acetal (2032-35-1) + tert-butylhydroquinone (1948-33-0) → 2-tert-Butyl-4-(2,2-diethoxy-ethoxy)-phenol (117516-67-3)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 6h; Heating;	93%

benzoic acid (65-85-0) + tert-butylhydroquinone (1948-33-0) → 3-(tert-butyl)-4-hydroxyphenyl benzoate (2444-27-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	93%

4-morpholino-4-yl-phenylamine (2524-67-6) + tert-butylhydroquinone (1948-33-0) → 2-[(4'-morpholinophenyl)amino]-6-tert-butyl-1,4-benzoquinone

Conditions	Yield
With citrate-phosphate buffer; Myceliophthora thermophila fungal laccase; oxygen at 20℃; pH=7; Enzymatic reaction;	92%

tert-butylhydroquinone (1948-33-0) + para-chlorobenzoic acid (74-11-3) → 3-(tert-butyl)-4-hydroxyphenyl 4-chlorobenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	91%

[1,3]-dioxolan-2-one (96-49-1) + tert-butylhydroquinone (1948-33-0) → 2,2'-(2-t-butyl-1,4-phenylenedioxy)diethanol (177539-44-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 140℃;	90%

[(η6-acenaphthene)manganese tricarbonyl][BF4] (864372-43-0) + tert-butylhydroquinone (1948-33-0) → [(η6-2-tert-butylhydroquinone)manganese tricarbonyl][BF4] (648442-05-1)

Conditions	Yield
In dichloromethane High Pressure; (N2); addn. of ligand to a soln. of manganese complex in CH2Cl2, sealing, heating to 70°C for 2 h, cooling to room temp.; filtration, washing with CH2Cl2, drying in vac.;	90%

2-furanoic acid (88-14-2) + tert-butylhydroquinone (1948-33-0) → 3-(tert-butyl)-4-hydroxyphenyl furan-2-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	89%

4-methoxy-benzoyl chloride (100-07-2) + tert-butylhydroquinone (1948-33-0) → 1,4 bis(4'-methoxybenzoyloxy) t-butylphenylene (79679-96-2)

Conditions	Yield
With pyridine; triethylamine for 4h;	88%

tetra-n-butyl ammonium + tert-butylhydroquinone (1948-33-0) → 2-tert-butyl-1,4-benzoquinone (3602-55-9)

Conditions	Yield
With hydrogenchloride In hexane; chloroform; water	88%

phenylacetic acid (103-82-2) + tert-butylhydroquinone (1948-33-0) → 3-(tert-butyl)-4-hydroxyphenyl 2-phenylacetate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	88%

(E)-3-phenylacrylic acid (140-10-3) + tert-butylhydroquinone (1948-33-0) → 3-(tert-butyl)-4-hydroxyphenyl cinnamate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	85%

ortho-methylbenzoic acid (118-90-1) + tert-butylhydroquinone (1948-33-0) → 3-(tert-butyl)-4-hydroxyphenyl 2-methylbenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	83%

tert-butylhydroquinone (1948-33-0) + 4-nitro-benzoic acid (62-23-7) → 3-(tert-butyl)-4-hydroxyphenyl 4-nitrobenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 6h;	83%

tert-butylhydroquinone (1948-33-0) + N-(E)-3-methylbut-1-enyl benzyl carbamate (914396-48-8) → benzyl (7-(tert-butyl)-5-hydroxy-3-isopropyl-2,3-dihydrobenzofuran-2-yl)carbamate

Conditions	Yield
With [bis(acetoxy)iodo]benzene; (R)-1,1'-spirobiindanyl-7,7'-diyl hydrogenphosphate In toluene at 20℃; for 16h; Inert atmosphere; stereoselective reaction;	83%

S-benzyl (E)-(3-methylbut-1-en-1-yl)carbamothioate + tert-butylhydroquinone (1948-33-0) → S-benzyl (7-(tert-butyl)-5-hydroxy-3-isopropyl-2,3-dihydrobenzofuran-2-yl)carbamothioate

Conditions	Yield
With [bis(acetoxy)iodo]benzene; (R)-1,1'-spirobiindanyl-7,7'-diyl hydrogenphosphate In toluene at 20℃; for 16h; Inert atmosphere; stereoselective reaction;	83%

(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)palladium(II) acetate (152506-88-2) + tert-butylhydroquinone (1948-33-0) → [(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)Pd(η2-2-tert-butyl-1,4-benzoquinone)]

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Sealed tube;	83%

benzyl bromide (100-39-0) + tert-butylhydroquinone (1948-33-0) → 2-(1,1-dimethylethyl)-1,4-bis(phenylmethoxy)benzene (35292-10-5)

Conditions	Yield
With potassium carbonate In acetone for 72h; Heating;	82%

Upstream product

• 3602-55-9 2-tert-butyl-1,4-benzoquinone 
• 123-31-9 hydroquinone 
• 115-11-7 isobutene 
• 21112-37-8 1,4-dimethoxy-2-tert-butylbenzene 
• 88-18-6 2-tert-Butylphenol 
• 540-88-5 acetic acid tert-butyl ester 
• 64-19-7 acetic acid 
• 75-65-0 tert-butyl alcohol 
• 90784-13-7 1,4-di-O-propanoyl-t-butylhydroquinone 
• 1634-04-4 tert-butyl methyl ether 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 4857-74-3 5-tert-butyl-1,2,4-trihydroxybenzene 
• 121-00-6 3-tert-Butyl-4-hydroxyanisole 
• 88-32-4 3-tert-butyl-4-methoxyphenol 

Downstream Products

• 73685-60-6 2-(1,1-dimethylethyl)-5-(2-propenyl)-1,4-benzenediol 
• 79950-49-5 5-allyloxy-2-hydroxy-t-butylbenzene 
• 7020-07-7 2-tert-Butyl-4-(2,3-epoxy-propoxy)-phenol 
• 31572-79-9 4-(iso-propoxy)-2-(tert-butyl)phenol 
• 2467-52-9 2-t-Butyl-4-t-butoxyphenol 
• 155135-23-2 2-(1,1-dimethylethyl)-4-(triisopropylsilyloxy)phenol 
• 79520-53-9 dimethyl 5,5'-[[2-(1,1-dimethylethyl)1,4-phenylene]bis(oxy)]bis[2,2-dimethylpentanoate] 
• 3602-55-9 2-tert-butyl-1,4-benzoquinone 
• 4024-47-9 N-Acetyl-3-<4-(3-tert-butyl-4-hydroxy-phenoxy)-3,5-dinitro-phenyl>-L-alanin-aethylester 
• 21099-14-9 2-bromo-5-(tert-butyl)-1,4-benzoquinone 
• 844-80-4 2-tert.-Butyl-5-tert.-octyl-hydrochinon 
• 177539-44-5 2,2'-(2-t-butyl-1,4-phenylenedioxy)diethanol 
• 21112-37-8 1,4-dimethoxy-2-tert-butylbenzene 
• 335590-64-2 1-O-(4-hydroxy-3-t-butyl)phenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Relevant articles and documents

Preparation and catalytic performance of perfluorosulfonic acid-functionalized carbon nanotubes

Perfluorosulfonic acid-functionalized carbon nanotubes were prepared by liquid deposition of the perfluorosulfonic acid-polytetrafluoroethylene copolymer and characterized by N2 adsorption, scanning electron microscopy, transmission electron mi

Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups

Candida antarctica lipase B proved to be highly active in the deacylation of substituted hydroquinones and resorcinols acylated at both phenolic hydroxy groups. The deacylation reactions were much faster than the corresponding direct acylations of these dihydroxybenzenes catalyzed by the same lipase. More importantly, they took place generally in a markedly regioselective manner: the acyloxy group remote from the substituent was preferentially cleaved. The main or exclusive products obtained were the regioisomers of those produced through the direct acylation of the dihydroxybenzenes. In the case of alkyl-substituted hydroquinone derivatives, the regioselectivity increased with an increase in the bulk of the substituent. In the case of 4-substituted diacylated resorcinols, the 3-O-monoacyl derivatives were obtained generally as the sole products. Quite interestingly, some secondary alcohols proved to act as better acyl acceptors than the corresponding primary alcohols in these enzymatic deacylations.

Tert-butylhydroquinone preparation method

The invention relates to the technical field of organic synthesis, and relates to a tert-butylhydroquinone preparation method, which comprises: 1) sequentially adding 2-tert-butylphenol, a transitionmetal copper (I) cooperation compound and a solvent to a high pressure reaction kettle, introducing oxygen to achieve a specified pressure, heating and stirring to a specified temperature, and carrying out a reaction for 0.5-3 h; 2) after the reaction is finished, evaporating out the solvent, washing the residual solid with a solvent, and carrying out steam stripping to obtain 2-tert-butyl p-benzoquinone; 3) sequentially adding the 2-tert-butyl p-benzoquinone obtained in the step 1), a catalyst and a solvent into a high-pressure reaction kettle, introducing hydrogen to a specified pressure after gas exchange is completed, heating and stirring to a specified temperature, and carrying out a reaction for 0.5-3 hours; and 4) after the reaction is finished, evaporating out the solvent, and rectifying to obtain the tert-butylhydroquinone product. According to the invention, the method has the advantages of high product yield, convenient operation, cheap raw materials, economy and reliability, and is suitable for large-scale production.

A PROCESS FOR PREPARATION OF TERTIARY BUTYL HYDROQUINONE

A PROCESS FOR PREPARATION OF TERTIARY BUTYL HYDROQUINONE The present invention relates to a process for preparation of tertiary butyl hydroquinone. More particularly, it relates to a process for preparation 5 of TBHQ by eradicating the consumption of hazardous solvents like toluene and eliminating hazardous impurities like hydroquinone, tertiary butyl‐p‐benzoquinone and also drastically reducing the presence of heavy metals like lead and arsenic. The present invention includes stages I‐IV in which TBHQ is more purified and precipitated with a high scale purity results. TBHQ has 10 application in food additives, animal feeds, as an antioxidant, emulsifier and in edible oils, effectively as antioxidant.