o-Xylene

Base Information

• Chemical Name: o-Xylene
• CAS No.: 95-47-6
• Molecular Formula: C8H10
• Molecular Weight: 106.167
• Hs Code.: 29024100
• European Community (EC) Number: 202-422-2
• ICSC Number: 0084
• NSC Number: 60920
• UN Number: 1307
• UNII: Z2474E14QP
• DSSTox Substance ID: DTXSID3021807
• Nikkaji Number: J3.563G
• Wikipedia: O-Xylene
• Wikidata: Q2988108,Q83048381
• Pharos Ligand ID: T3U3TPV1R9MX
• Metabolomics Workbench ID: 51574
• ChEMBL ID: CHEMBL45005
• Mol file: 95-47-6.mol

Synonyms:1,2-dimethylbenzene;1,2-xylene;2-xylene;o-xylene;o-xylol;ortho-xylene

Chemical Property of o-Xylene

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: <0.1 atm ( 21.1 °C)
• Melting Point: -26--23 °C
• Refractive Index: 1.505
• Boiling Point: 145.949 °C at 760 mmHg
• PKA: >15 (Christensen et al., 1975)
• Flash Point: 28.882 °C
• PSA: 0.00000
• Density: 0.87 g/cm³
• LogP: 2.30340
• Storage Temp.: 0-6°C
• Solubility.: water: partially soluble0.1705 g/L at 25°C
• Water Solubility.: Sparingly soluble in water. (0.2g/L)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 106.078250319
• Heavy Atom Count: 8
• Complexity: 56.4
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.0% ^*data from raw suppliers

o-Xylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,F
• Hazard Codes: Xn,T,F
• Statements: 10-20/21-38-39/23/24/25-23/24/25-11
• Safety Statements: 25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=CC=C1C
• 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: The substance is irritating to the eyes and skin. The substance may cause effects on the central nervous system. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the central nervous system. Exposure to the substance may increase noise-induced hearing loss. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Uses: (1)? It is mainly used in the production of phthalic anhydride (2)? O-xylene is the raw material for the production of germicide fenramine, tetrachlorophenyl peptide and the herbicide bensulfuron-methyl. It is used as intermediate for the manufacture of o-methyl benzoic acid. (3)? It is mainly used as chemical raw materials and solvents. It can be used to produce phthalic anhydride, dyes, pesticides and drugs, such as vitamins. It can also be used as aviation gasoline additives. (4)? Used as chromatographic standards and solvents (5)? As raw materials of synthesis of anhydride and other organic synthesis; Preparation of phthalic acid, phthalic anhydride, terephthalic acid, isophthalic acid; solvent for alkyd resins, lacquers, enamels, rubber cements; manufacture of dyes, pharmaceuticals, and insecticides; motor fuels. o-Xylene is largely used in the production of phthalic anhydride, and is generally extracted by distillation from a mixed Xylene stream in a plant primarily designed for p-Xylene production. Xylene, xylenes, and total xylenes are used interchangeably since xylene usually exists as a mixture of three isomers: 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene, i.e., o-, m-, and p-xylene, and is usually used as a mixture of the three forms. The mixture often also contains ethylbenzene. It is a high volume industrial chemical used in the synthetic fiber, chemical and plastics industries and as a solvent, cleaning agent and thinner for paints and varnishes.
• Production method: Industry applied super-distillation method to separate out the o-xylene from the mixed xylene. O-xylene has a over 5 ℃ difference in the boiling point compared with other components in the mixed xylene. For the distillation, the required tray number is about 150; the reflux ratio being 5-8 and consume relative much energy. O-xylene was originally produced mainly from coal tar. Currently most of the domestic and foreign production of o-xylene is mainly via extraction from oil catalytic reforming and thermal cracking of aromatic hydrocarbon. Owing to that the structures of o-xylene, p-xylene, and m-xylene in the xylene are very similar; their physical parameters are also quite similar. Industrial o-xylene separation mainly adopts super-distillation method; first separate out the o-xylene and ethylbenzene from the mixed xylene which demands the using of 100~150 tray distillation tower; followed by separation of o-xylene and ethylbenzene to obtain pure o-xylene.
• Physical properties: Clear, colorless liquid with an aromatic odor. An odor threshold concentration of 380 ppbv was reported by Nagata and Takeuchi (1990).

Technology Process of o-Xylene

There total 491 articles about o-Xylene 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: 13.2%

heptadecyl acetate (822-20-8) + toluene (108-88-3,15644-74-3,16713-13-6) → 1-undecene (821-95-4) + heptadec-1-ene (6765-39-5) + o-xylene (95-47-6) + 2-Ethyltoluene (611-14-3) + 1-methyl-2-vinyl-benzene (611-15-4) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

at 490 ℃; Rate constant; Product distribution; various temp., also with 14C-labelled ester;

DOI:10.1021/jo00083a028

Reference yield: 2.5%

octane (111-65-9) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4-octene (592-99-4,7642-15-1,14850-23-8) + oct-3-ene (14850-22-7,14919-01-8,138663-42-0,592-98-3) + cis-2-octene (7642-04-8) + trans-2-Octene (13389-42-9) + oct-1-ene (111-66-0,25068-25-1) + o-xylene (95-47-6) + ethylbenzene (100-41-4,27536-89-6)

Guidance literature:

With V₂O₅-MnO (15percent V₂O₅); air; N₂; at 450 ℃; Gas phase; Continuous flow fixed bed reactor;

DOI:10.1016/j.apcata.2009.11.004

Reference yield:

octane (111-65-9) → o-xylene (95-47-6) + para-xylene (106-42-3) + ethylbenzene (100-41-4,27536-89-6) + m-xylene (108-38-3,104809-90-7)

Guidance literature:

at 482 ℃; Product distribution; various of catalyst, support type and total pressure, investigation of distribution of C₈ aromatics;

upstream raw materials:

3,4-Dimethylphenol

ortho-tolylmagnesium bromide

2-benzofuran-1(3H)-one

1,3-dihydrobenzo[c]thiophene-2,2-dioxide

Downstream raw materials:

1-(3,4-dimethylphenyl)butane-1,3-dione

dimethyl 3-methylbenzene-1,2-dicarboxylate

dimethyl 4,5-dimethylphthalate

dimethyl 3,4-dimethylphthalate

Refernces

• 1、 Andrade, Juan G.,Maier, Wilhelm F.,Zapf, Lothar,Schleyer, Paul von Rague. "Catalytic Hydrogenolysis; III. Direct Transformation of Cyano into Methyl Groups". . p. 802 - 803. Retrieved 1980.
• 2、 Fan, Minghui,He, Yuting,Li, Quanxin,Luo, Yuehui,Yang, Mingyu,Zhang, Yanhua,Zhu, Lijuan. "Selective catalytic synthesis of bio-based high value chemical of benzoic acid from xylan with Co2MnO4@MCM-41 catalyst". . . Retrieved 2021/12/20.
• 3、 Dong, Jinxiang,Ge, Hui,Han, Tengfei,Li, Xuekuan,Liu, Jianchao,Xu, Hong,Zhou, Ligong. "One-Pass Conversion of Benzene and Syngas to Alkylbenzenes by Cu–ZnO–Al2O3 and ZSM-5 Relay". . . Retrieved 2021/05/21.