721-26-6

Basic information

• Product Name: META-DIISOPROPYLBENZENEDIHYDROPEROXIDE
• Synonyms: META-DIISOPROPYLBENZENEDIHYDROPEROXIDE
• CAS NO: 721-26-6
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27
• Mol File: 721-26-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 61 °C
• Boiling Point: 376.8°C at 760 mmHg
• Flash Point: 181.7°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 2.4E-06mmHg at 25°C
• Refractive Index: 1.522
• PKA: 11.84±0.30(Predicted)
• CAS DataBase Reference: META-DIISOPROPYLBENZENEDIHYDROPEROXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: META-DIISOPROPYLBENZENEDIHYDROPEROXIDE(721-26-6)
• EPA Substance Registry System: META-DIISOPROPYLBENZENEDIHYDROPEROXIDE(721-26-6)

Safety Data

• Hazardous Substances Data: 721-26-6(Hazardous Substances Data)

Usage

General Description

META-DIISOPROPYLBENZENEDIHYDROPEROXIDE is a chemical compound that is commonly used as a polymerization initiator and a crosslinking agent in the plastics and rubber industries. It is a highly reactive organic peroxide, and is often used in combination with other peroxides to initiate the polymerization process. META-DIISOPROPYLBENZENEDIHYDROPEROXIDE is a source of free radicals and is able to initiate the crosslinking of polymers, which leads to the formation of a network structure in the material. It is also used as a curing agent for unsaturated polyester resins and as a disinfectant for medical equipment. It should be handled with care, as it is a strong oxidizing agent and can pose a fire hazard if not properly stored and handled.

InChI:InChI=1/C12H18O4/c1-11(2,15-13)9-6-5-7-10(8-9)12(3,4)16-14/h5-8,13-14H,1-4H3

Synthetic route

1,3-diisopropylbenzene (99-62-7) + 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene (80-24-0) → 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6)

Conditions	Yield
With oxygen In water at 83 - 92℃; under 2250.23 Torr; for 10h; pH=9 - 11; Product distribution / selectivity;	66.1%
With oxygen; sodium formate; sodium acetate; iron(II) acetate; sodium carbonate In water at 90℃; under 2250.23 Torr; for 6h; Product distribution / selectivity;
With oxygen; sodium formate; sodium acetate; sodium carbonate In water at 90℃; under 2250.23 Torr; for 6h; Product distribution / selectivity;
With oxygen at 90℃; Product distribution / selectivity;

1,3-diisopropylbenzene (99-62-7) → 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene (80-24-0) + 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6)

Conditions	Yield
With air; sodium carbonate at 90℃;
With air; sodium carbonate at 90℃;

1,3-diisopropylbenzene (99-62-7) → 1,3-bis(1',1'-dimethylhydroxymethyl)benzene (1999-85-5) + 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene (13387-60-5) + 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene (80-24-0) + 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6) + 2-(3-isopropyl-phenyl)-propan-2-ol (14860-89-0)

Conditions	Yield
With oxygen; 1,10-Phenanthroline; magnesium naphthenate at 80 - 120℃; Rate constant; Kinetics; Thermodynamic data; E(act.) for various reaction products formation, other catalyst;

1,3-diisopropylbenzene (99-62-7) → 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene (13387-60-5) + 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene (80-24-0) + 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6)

Conditions	Yield
With oxygen; amino acids copper salts at 110℃; Product distribution; var. catalysts, selectivity of catalysts;
With oxygen at 90℃; under 2250.23 Torr; for 10h; pH=9 - 11; Product distribution / selectivity;

1,3-diisopropylbenzene (99-62-7) + oxygen (80937-33-3) → m-(2-hydroperoxy-2-propyl)acetophenone + 1,3-bis(1',1'-dimethylhydroxymethyl)benzene (1999-85-5) + 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene (13387-60-5) + 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6) + acetylisopropylbenzene monocarbinol (87771-41-3) + 2-(3-isopropyl-phenyl)-propan-2-ol (14860-89-0) + 1-[3-(propan-2-yl)phenyl]ethan-1-one (40428-87-3)

Conditions	Yield
With sodium hydroxide; 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene In water at 90℃;

...Expand

3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene (13387-60-5) → m-(2-hydroperoxy-2-propyl)acetophenone + 1,3-bis(1',1'-dimethylhydroxymethyl)benzene (1999-85-5) + 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene (80-24-0) + 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6) + acetylisopropylbenzene monocarbinol (87771-41-3) + 2-(3-isopropyl-phenyl)-propan-2-ol (14860-89-0) + 1-[3-(propan-2-yl)phenyl]ethan-1-one (40428-87-3)

Conditions	Yield
With sodium hydroxide In water; 4-methyl-2-pentanone at 90℃; Heating / reflux;

3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene (13387-60-5) → m-(2-hydroperoxy-2-propyl)acetophenone + 1,3-bis(1',1'-dimethylhydroxymethyl)benzene (1999-85-5) + 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene (80-24-0) + 1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6) + acetylisopropylbenzene monocarbinol (87771-41-3) + 2-(3-isopropyl-phenyl)-propan-2-ol (14860-89-0)

Conditions	Yield
With sodium sulfite In water; 4-methyl-2-pentanone Heating / reflux;

1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6) → acetone (67-64-1) + recorcinol (108-46-3)

Conditions	Yield
sulfur trioxide In 4-methyl-2-pentanone at 70℃; for 0.166667h; Product distribution / selectivity;	A n/a B 94%

1,3-di(2-hydroperoxy-2-propyl)benzene (721-26-6) → recorcinol (108-46-3)

Conditions	Yield
With sulfuric acid; acetone; butanone
With with acid-agent treated Fuller's earth; acetone; benzene

Upstream product

• 99-62-7 1,3-diisopropylbenzene 
• 80-24-0 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene 
• 80937-33-3 oxygen 
• 13387-60-5 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene 

Downstream Products

• 67-64-1 acetone 
• 108-46-3 recorcinol 

Relevant articles and documents

PROCESS FOR PRODUCTION OF DIALKYLHYDROPEROXYBENZENES

To provide a method for producing dialkylhydroperoxybenzene by liquid-phase oxidation of dialkylbenzene, wherein the method comprises the following steps, Oxidation step: a step of obtaining a oxidation reaction liquid having pH of 9 to 12, which contains dialkylhydroperoxybenzene, unreacted dialkylbenzene, and by-produced hydroperoxybenzenes by subjecting an oxidation raw material solution containing dialkylbenzene to oxidation reaction, Aqueous solution extracting step: a step of extracting the oxidation reaction liquid with an alkaline aqueous solution to obtain a water layer mainly containing dialkylhydroperoxybenzene and by-produced hydroperoxybenzenes, and an oil layer mainly containing dialkylbenzene, and Recycle step: a step of recycling and feeding at least a part of the oil layer obtained in the aqueous solution extracting step to the oxidation step, wherein the oxidation step comprises two or more reaction sections of a first section and subsequent sections arranged in series, and the temperature of the first reaction section is set to be higher than an average temperature of the whole reaction sections by 2.5°C or more.

Process for producing alkyl aromatic hydroperoxide

A process for producing an alkyl aromatic hydroperoxide, which comprises oxidizing an alkyl aromatic compound with an oxygen-containing gas in the presence of a water-soluble iron compound, wherein a concentration of the iron compound in the oxidation reaction system is 0.0001 to 10 ppm by weight in terms of iron metal.

Process for the production of a dihydroxybenzene and dicarbinol from diisopropylbenzene

Improved methods for the simultaneous production of dihydroxybenzene and dicarbinol from diisopropylbenzene are provided. These methods provide for continuous and simultaneous production of diisopropylbenzene dihydroperoxide (DHP) and diisopropylbenzene hydroxyhydroperoxide (HHP) using Karr Column extractors operated in series. A very high purity DHP-containing solution, the precursor to the dihydroxybenzene, can be produced according to the reported methods. A safe and efficient method for producing dicarbinol from HHP is also disclosed.