Cumene

Base Information

• Chemical Name: Cumene
• CAS No.: 98-82-8
• Molecular Formula: C9H12
• Molecular Weight: 120.194
• Hs Code.: 29027000
• European Community (EC) Number: 202-704-5,685-463-2
• ICSC Number: 0170
• NSC Number: 8776
• UN Number: 1918
• UNII: 8Q54S3XE7K
• DSSTox Substance ID: DTXSID1021827
• Nikkaji Number: J3.581E
• Wikipedia: Cumene
• Wikidata: Q410107,Q83038079
• Metabolomics Workbench ID: 46330
• ChEMBL ID: CHEMBL1398949
• Mol file: 98-82-8.mol

Synonyms:2-phenylpropane;cumene;cumol;isopropylbenzene

Chemical Property of Cumene

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 8 mm Hg ( 20 °C)
• Melting Point: -96 °C(lit.)
• Refractive Index: n20/D 1.491(lit.)
• Boiling Point: 152.409 °C at 760 mmHg
• PKA: >14 (Schwarzenbach et al., 1993)
• Flash Point: 31.135 °C
• PSA: 0.00000
• Density: 0.862 g/cm³
• LogP: 2.81000
• Storage Temp.: 2-8°C
• Solubility.: 0.05g/l
• Water Solubility.: Soluble in alcohol, ether, acetone, benzene, carbon tetrachloride. Insoluble in water.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 120.093900383
• Heavy Atom Count: 9
• Complexity: 68.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Cumene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N,T,F
• Statements: 10-37-51/53-65-39/23/24/25-23/24/25-11
• Safety Statements: 24-37-61-62-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Aromatic Solvents
• Canonical SMILES: CC(C)C1=CC=CC=C1
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: If swallowed the substance easily enters the airways and could result in aspiration pneumonitis. The substance may cause effects on the central nervous system. Exposure far above the OEL could cause unconsciousness.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver and upper respiratory tract. This substance is possibly carcinogenic to humans.
• Uses: Industrial Use Cumene is utilized in the production of phenol or its product, acetone that is widely used in the manufacture of plastics and petroleum products. It is also used in the production of methyl styrene and acetophenone as well as a thinner in lacquers, paints, and enamels. In addition, the compound is used as a solvent in the manufacture of iron, rubber, and steel as well as paper and pulp. Pharmaceutical Use Cumene hydroperoxide produces oxidative stress in the various steps of protein synthesis. Cumene hydroperoxide is used to probe isoenzyme specificity as well as region-and stereoselectivity. It is used as a solvent and in the productionof phenol, acetone, and acetophenone. Raw Material for Phenol, Acetone and Alpha Methyl Styrene production, intermediate for argochemicals Production of phenol, acetone, and α- methylstyrene; solvent. Around 98% of cumene is used in the production of phenol and its coproduct, acetone, using cumene hydroperoxide as chemical intermediate. However, the demand for cumene is largely dependent on the performance of phenol’s derivatives, which have resulted in healthy growth rates in demand for cumene. It is also used as a starting material in the production of acetophenone, α-methylstyrene, diisopropylbenzene, and dicumylperoxide. Cumene is used as a thinner for paints, lacquers, and enamels. It is also used in the manufacture of acetophenone, methylstyrene, and other chemicals commonly found in home cleaning products. Minor uses of cumene include as a constituent of some petroleum-based solvents, such as naphtha; in gasoline blending diesel fuel and highoctane aviation fuel; and as a raw material for peroxides and oxidation catalysts such as polymerization catalysts for acrylic and polyester-type resins. It is also a good solvent for fats and resins and has been suggested as a replacement for benzene in many of its industrial applications.
• Description: Cumene is a common name for isopropylbenzene, an organic compound. Cumene is a volatile colorless liquid at room temperature with a characteristic sharp, penetrating, aromatic odor. It is insoluble in water but is soluble in alcohol and many other organic solvents. Cumene is structurally a member of the alkyl aromatic family of hydrocarbons, which also includes toluene (methylbenzene) and ethylbenzene.Cumene can be found in crude oil, refined fuels, and is a part of processed highoctane gasoline. Cumene is manufactured by reacting benzene with propylene at elevated temperature and pressure in the presence of a catalyst. It is considered an environmental pollutant because it is a natural component of petroleum and is present in tobacco smoke. Cumene vapor can be absorbed by the respiratory tract. Sufficiently high levels of exposure to cumene causes central nervous system (CNS) depression leading to death, internal bleeding of numerous organs, as well as irritation of the eyes and respiratory system, skin, and mucous membranes. Cumene is a high production volume chemical.
• Physical properties: Colorless liquid with an aromatic odor. Experimentally determined detection and recognition odor threshold concentrations were 40 μg/m3 (8 ppbv) and 230 μg/m3 (47 ppbv), respectively (Hellman and Small, 1974). The taste threshold concentration in water is 60 ppb (Young et al., 1996).

Technology Process of Cumene

There total 528 articles about Cumene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 14.7%

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Isopropylbenzene (98-82-8) + 1,4-bis(1-methylethyl)benzene (100-18-5) + ethylbenzene (100-41-4,27536-89-6) + 1,3-diisopropylbenzene (99-62-7) + toluene (108-88-3,15644-74-3,16713-13-6)

Guidance literature:

A-45 zeolite; at 200 ℃; Product distribution; Rate constant; Mechanism; var. ratio of reactants, oth. temperature, effect of size of catalyst particles;

Reference yield: 14.6%

(Z)-2-Butene (590-18-1) + propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + propane (74-98-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Isopropylbenzene (98-82-8) + 1,4-bis(1-methylethyl)benzene (100-18-5) + 1,3-diisopropylbenzene (99-62-7) + 1,2-diisopropylbenzene (577-55-9)

Guidance literature:

specimen (II); at 40 ℃; Product distribution;

Reference yield: 14.0%

(Z)-2-Butene (590-18-1) + propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + propane (74-98-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Isopropylbenzene (98-82-8) + 1,4-bis(1-methylethyl)benzene (100-18-5) + 1,3-diisopropylbenzene (99-62-7) + 1,2,4-triisopropylbenzene (948-32-3) + 1,2-diisopropylbenzene (577-55-9)

Guidance literature:

specimen (I); at 40 ℃; Product distribution;

upstream raw materials:

styrene

(1-bromoethyl)benzne

2-iodo-propane

bromobenzene

Downstream raw materials:

di(pyridin-2-yl)amine

octane

dicumene

(1-isothiocyanato-1-methyl-ethyl)-benzene

Refernces

• 1、 Punji, Benudhar,Balakrishna, Maravanji S.. "Large bite bisphosphite, 2,6-C5H3N{CH2OP(-OC10H6)(μ-S)(C10H6O-)}2: Synthesis, derivatization, transition metal chemistry and application towards hydrogenation of olefi". . p. 1683 - 1689. Retrieved 2007.
• 2、 Martin, Marta,Sola, Eduardo,Tejero, Santiago,Lopez, Jose A.,Oro, Luis A.. "Mechanistic investigations of imine hydrogenation catalyzed by dinuclear iridium complexes". . p. 4057 - 4068. Retrieved 2006.
• 3、 Dolgow,Tscherkasow. "-". . p. 825; engl. Ausg. S. 825. Retrieved 1954.
• 4、 Yamamoto et al.. "". . p. 2474. Retrieved 1978.
• 5、 Di, Yali,Li, Guangyu,Li, Zhiqin,Liu, Weiwei,Qiu, Zegang,Ren, Xiaoxiong,Wang, Ying. "One-step conversion of lignin-derived alkylphenols to light arenes by co-breaking of C-O and C-C bonds". . p. 2710 - 2721. Retrieved 2022/02/21.
• 6、 Han, Bo,Jiao, Hongmei,Ma, Haojie,Wang, Jijiang,Zhang, Miaomiao,Zhang, Yuqi. "Ligand-enabled and magnesium-activated hydrogenation with earth-abundant cobalt catalysts". . p. 39934 - 39939. Retrieved 2021/12/31.