Mesitylene

Base Information

• Chemical Name: Mesitylene
• CAS No.: 108-67-8
• Molecular Formula: C9H12
• Molecular Weight: 120.194
• Hs Code.: 29029080
• European Community (EC) Number: 203-604-4
• ICSC Number: 1155
• NSC Number: 9273
• UN Number: 2325
• UNII: 887L18KQ6X
• DSSTox Substance ID: DTXSID6026797
• Nikkaji Number: J2.424D
• Wikipedia: Mesitylene
• Wikidata: Q425161
• Metabolomics Workbench ID: 49631
• ChEMBL ID: CHEMBL1797281
• Mol file: 108-67-8.mol

Synonyms:mesitylene

Chemical Property of Mesitylene

Chemical Property:

• Appearance/Colour: colorless liquid with a peculiar odor
• Vapor Pressure: 14 mm Hg ( 55 °C)
• Melting Point: -45 °C
• Refractive Index: n20/D 1.499(lit.)
• Boiling Point: 166.7 °C at 760 mmHg
• PKA: >14 (Schwarzenbach et al., 1993)
• Flash Point: 44.4 °C
• PSA: 0.00000
• Density: 0.869 g/cm³
• LogP: 2.61180
• Storage Temp.: 2-8°C
• Solubility.: Miscible with alcohol, benzene, ether (Windholz et al., 1983), and trimethylbenzene isomers.
• Water Solubility.: 2.9 g/L (20 ºC)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 120.093900383
• Heavy Atom Count: 9
• Complexity: 55
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Mesitylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,F,T
• Hazard Codes: Xi,N,F,T
• Statements: 10-37-51/53-39/23/24/25-23/24/25-11-37/38
• Safety Statements: 61-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Aromatic Solvents
• Canonical SMILES: CC1=CC(=CC(=C1)C)C
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. Repeated or prolonged inhalation may cause effects on the lungs. This may result in chronic bronchitis. The substance may have effects on the central nervous system and blood.
• Uses: It can be used for the production of trimesic acid and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizers and dyes etc. It can be used as raw material of organic synthesis, it can be used in the preparation of trimesic acid, and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizer, 2,4,6-trimethyl aniline reactive brilliant blue, K-3R and other dye. It can be used as analytical reagents, solvents, it can be also used in organic synthesis, etc. Intermediate, including anthraquinone vat dyes, UV oxidation stabilizers for plastics. Mesitylene is used to make plastics and dyes. It acts as a solvent, ligand in organometallic chemistry and precursor to 2,4,6-trimethylaniline. It is also used as a developer for photopatternable silicones due to its solvent properties in the electronics industry. It is used as an internal standard in nuclear magnetic resonance (NMR) samples due to the presence of three equivalent protons in it. It is involved in the production of trimesic acid and antioxygen, epoxy firming agent and polyester resin stabilizers. Further, it is used as an additive and component in aviation gasoline blends.
• Production method: 1. It is derived by the separation of C9 aromatic hydrocarbon. 2. In the reforming of heavy aromatics the amount of mesitylene is about 11.8%. However, due to its boiling point (164.7 ℃) is extremely close to the boiling point of O-methyl benzene (165.15 ℃), it is difficult to separate for using distillation method. 3.The isomerization method with partial three toluene as raw material can fractionate, and can get mesitylene which the one way yield is 21.6%, the purity is more than 95%, while 4%-7% of by-product is durene, xylene is 9%. The average temperature of reactor bed is 260℃, pressure is 2.35MPa, empty the entire is 1.0h-1, molar ratio of reforming hydrogen and oil is 10: 1, the catalyst is mordenite which lack of aluminum hydrogen form: Cu: Ni: binder = 85.2: 0.5: 15. Under these conditions, the conversion rate of partial three toluene is 46%, selectivity is 47% , one way yield of mesitylene is 21.6%. HF-BF3 is xylene separated and through the method of isomerization by Japanese Mitsubishi Gas Company, by-products contain high concentration of mesitylene of high boiling, the goods can be get by distilled and refined. 4. Acetone in sulfuric acid-catalyzed goes through dehydration synthesis can obtain this goods with the yield of 13%-15%. 4600g (79mol) of industrial acetone is cooled to 0-5℃, and 4160ml concentrated sulfuric acid is added with stirring, the temperature can not exceed 10℃. After addition is completed, cntinue stirring 3-4h, place at room temperature for 18-24h. The product is subjected to steam distillation, mesitylene is separated, then it is washed with alkali, water, and then collect distillation fraction of 210℃, 15g sodium metal is added into this fraction, it is heated to near the boiling point, 2/3 liquid is evaporated. the residue is distilled to 210℃, efficient fractionation collection is done for the 163-167℃ distillate, 430-470g1,3,5-mesitylene can be obtained.
• Physical properties: Colorless liquid with a peculiar odor. An odor threshold concentration of 170 ppbv was reported by Nagata and Takeuchi (1990).

Technology Process of Mesitylene

There total 417 articles about Mesitylene 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: 74.0%

methanol (67-56-1) + acetone (67-64-1) → pentamethylbenzene, (700-12-9) + Hexamethylbenzene (87-85-4) + 1,3,5-trimethyl-benzene (108-67-8)

Guidance literature:

With aluminum oxide; at 420 ℃; flowrate: 33 ml/ h;

Reference yield: 44.5%

2,4,6-Trimethylacetophenone (1667-01-2,51885-97-3) + methoxybenzene (100-66-3) → 2-Methoxyacetophenone (579-74-8) + 1-(4-methoxyphenyl)ethanone (100-06-1) + 1,3,5-trimethyl-benzene (108-67-8)

Guidance literature:

trifluoroacetic acid; for 20h; Heating;

DOI:10.1039/P29860000847

Reference yield: 38.0%

2,4,6-Trimethylbenzophenon (954-16-5) + methoxybenzene (100-66-3) → 4-Methoxybenzophenone (611-94-9) + 1,3,5-trimethyl-benzene (108-67-8)

Guidance literature:

With Nafion-H; for 12h; Heating;

DOI:10.1021/jo00167a053

upstream raw materials:

tetrachloromethane

Dimethyl ether

1,3,5,5-tetramethyl-1,3-cyclohexadiene

phorone

Downstream raw materials:

β-(2,4,6-trimethylbenzoyl)acrylic acid

4-oxo-4-(2.4.6-trimethyl-phenyl)-trans-crotonic acid

3-(3,5-dimethylphenyl)propanoic acid

3-(2,4,6-Trimethylbenzoyl)-propionic acid

Refernces

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• 2、 Ryan, John H.,Stang, Peter J.. "Direct α-arylation of ketones: The reaction of cyclic ketone enolates with diphenyliodonium triflate". . p. 5061 - 5064. Retrieved 1997.
• 3、 Keumi, Takashi,Morita, Toshio,Ozawa, Yoshihiro,Kitajima, Hidehiko. "The Triflic Acid-Catalysed Deacylation and Decarboxylation of Polymethylbenzenecarbonyl Derivatives under Mild Conditions". . p. 599 - 601. Retrieved 1989.
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• 6、 Luo, Shengcheng,Falconer, John L.. "Acetone and acetaldehyde oligomerization on TiO2 surfaces". . p. 393 - 407. Retrieved 1999.
• 7、 Demorest et al.. "". . p. 2569,2572. Retrieved 1951.
• 8、 Zhang, Kainan,Conda-Sheridan, Martin,R. Cooke, Shayna,Louie, Janis. "N-heterocyclic carbene bound nickel(I) complexes and their roles in catalysis". . p. 2546 - 2552. Retrieved 2011.
• 9、 Nickels,Heintzelman. "-". . p. 1142,1143, 1145. Retrieved 1950.
• 10、 Kahlert, Jan,B?hling, Lena,Brockhinke, Andreas,Stammler, Hans-Georg,Neumann, Beate,Rendina, Louis M.,Low, Paul J.,Weber, Lothar,Fox, Mark A.. "Syntheses and reductions of C-dimesitylboryl-1,2-dicarba-closo-dodecaboranes". . p. 9766 - 9781. Retrieved 2015.