79-74-3

Basic information

• Product Name: 2,5-Di(tert-amyl)hydroquinone
• Synonyms: 2,5-Di-t-amylhydroquinone;2,5-Di-t-amyl-p-hydroquinone;2,5-Di-tert-amylbenzene-1,4-diol;2,5-di-tert-amyl-hydroquinon;2,5-Ditert-pentyl-1,4-benzenediol;2,5-Di-tert-pentylbenzene-1,4-diol;2,5-di-tert-pentyl-hydroquinon;2,5-di-t-pentyl-hydroquinon
• CAS NO: 79-74-3
• Molecular Formula: C₁₆H₂₆O₂
• Molecular Weight: 250.38
• EINECS: 201-222-2
• Product Categories: Industrial/Fine Chemicals
• Mol File: 79-74-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 179 °C
• Boiling Point: 353.51°C (rough estimate)
• Flash Point: 162.7 °C
• Appearance: White powder
• Density: 0.9781 (rough estimate)
• Vapor Pressure: 7.84E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 11.21±0.23(Predicted)
• Water Solubility: 200ng/L at 20℃
• Merck: 14,3304
• CAS DataBase Reference: 2,5-Di(tert-amyl)hydroquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Di(tert-amyl)hydroquinone(79-74-3)
• EPA Substance Registry System: 2,5-Di(tert-amyl)hydroquinone(79-74-3)

Safety Data

• WGK Germany: 3
• RTECS: MX6300000
• Hazardous Substances Data: 79-74-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise the hydroquinone under N2 from boiling AcOH (7mL/g) plus boiling water (2.5mL/g). [Stolow & Bonaventura J Am Chem Soc 85 3636 1963]. Store it in sealed ampoules under N2 away from light. [Beilstein 6 H 952, 6 III 4748.]

InChI:InChI=1/C16H26O2/c1-7-15(3,4)11-9-14(18)12(10-13(11)17)16(5,6)8-2/h9-10,17-18H,7-8H2,1-6H3

Synthetic route

2-methyl-but-2-ene (513-35-9) + hydroquinone (123-31-9) → 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3)

Conditions	Yield
methanesulfonic acid In toluene at 55 - 70℃; for 7h; Product distribution / selectivity;	90%
toluene-4-sulfonic acid In toluene at 85 - 110℃; for 4.5 - 7.5h; Product distribution / selectivity;

tert-Amyl alcohol (75-85-4) + hydroquinone (123-31-9) → 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3)

Conditions	Yield
With sulfuric acid; acetic acid at 20℃; for 7h;	78%
With sulfuric acid
methanesulfonic acid In toluene at 88 - 110℃; for 8.5h; Product distribution / selectivity;

hydroquinone (123-31-9) → 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3)

Conditions	Yield
With acetic acid man gibt dann Amylen zu;

2-methyl-but-2-ene (513-35-9) + sulfuric acid (7664-93-9) + acetic acid (64-19-7) + hydroquinone (123-31-9) → 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3)

hydroquinone (123-31-9) + tert.-pentyl chloride → 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3)

Conditions	Yield
With ethanol; zinc(II) chloride

2,5-bis-(1,1-dimethylpropyl)-1,4-benzoquinone (4584-63-8) + acetic acid (64-19-7) + zinc dust → 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3)

ethanol (64-17-5) + 2-methoxy-phenol (90-05-1) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With ortho-tungstic acid at 300℃; for 6h; Autoclave;

...Expand

ethanol (64-17-5) + 2-methoxy-phenol (90-05-1) → 2-Ethoxyphenol (94-71-3) + 3,5-Di-tert-butylcatechol (1020-31-1) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With tungsten(VI) oxide at 300℃; for 6h; Reagent/catalyst; Autoclave;

...Expand

ethanol (64-17-5) + benzene-1,2-diol (120-80-9) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With ortho-tungstic acid at 300℃; for 6h; Autoclave;

...Expand

2-Ethoxyphenol (94-71-3) + ethanol (64-17-5) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With ortho-tungstic acid at 300℃; for 6h; Autoclave;

...Expand

2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) → 2,5-bis-(1,1-dimethylpropyl)-1,4-benzoquinone (4584-63-8)

Conditions	Yield
With sodium hypochlorite; tetra(n-butyl)ammonium hydrogensulfate In ethyl acetate for 0.0833333h; Ambient temperature;	78%
With ethanol; iron(III) chloride
With thallium(III) trifluoroacetate

2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + acetic anhydride (108-24-7) → 1,4-diacetoxy-2,5-di-tert-pentyl-benzene

2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + phenyl isocyanate (103-71-9) → 1,4-di-tert-pentyl-2,5-bis-phenylcarbamoyloxy-benzene

ethanol (64-17-5) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + iron(III) chloride (7705-08-0) → 2,5-bis-(1,1-dimethylpropyl)-1,4-benzoquinone (4584-63-8)

2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) → C16H25O2

Conditions	Yield
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl In tetrachloromethane; acetonitrile Kinetics; Further Variations:; Solvents;

2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + trimellitic anhydride acid chloride (1204-28-0) → C34H30O10

Conditions	Yield
With pyridine In tetrahydrofuran

Upstream product

• 64-17-5 ethanol 
• 90-05-1 2-methoxy-phenol 
• 120-80-9 benzene-1,2-diol 
• 94-71-3 2-Ethoxyphenol 
• 513-35-9 2-methyl-but-2-ene 
• 123-31-9 hydroquinone 
• 75-85-4 tert-Amyl alcohol 
• 4584-63-8 2,5-bis-(1,1-dimethylpropyl)-1,4-benzoquinone 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 

Downstream Products

• 4584-63-8 2,5-bis-(1,1-dimethylpropyl)-1,4-benzoquinone 

Relevant articles and documents

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.

PRODUCTION OF A DISUBSTITUTED HYDROQUINONES

A process for the production of a disubstituted hydroquinone which comprises alkylating hydroquinone in the presence of a sulphonic acid condensation catalyst with an olefin or a substance which under the reaction conditions acts as a source thereof. The preferred olefin is 2-methyl-2-butene either alone or in admixture- with isomers thereof, and the preferred catalyst is methane sulphonic acid and the reaction product is 2,5-di-tert-amylhydroquinone. Only catalytic amounts of catalyst are required. The reaction product is worked-up by complete dissolution of the desired product and washing with an aqueous medium containing a pH buffering agent and a reducing agent.

Thioether substituted hydroxybenzophenones and stabilized compositions

2-Hydroxybenzophenone derivatives substituted in the 4′-position by a thioether moiety exhibit enhanced absorption in the UV at longer wavelength. Compositions comprising organic material subject to actinic degradation are beneficially stabilized with such derivatives.