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1,4-Diethylbenzene
[CAS# 105-05-5]

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Identification
ClassificationChemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
Name1,4-Diethylbenzene
Synonymsp-Diethylbenzene; p-Ethylethylbenzene
Molecular StructureCAS # 105-05-5, 1,4-Diethylbenzene
Molecular FormulaC10H14
Molecular Weight134.22
CAS Registry Number105-05-5
EC Number203-265-2
SMILESCCC1=CC=C(C=C1)CC
Properties
SolubilityInsoluble (7.7E-3 g/L) (25 °C), Calc.*
Density0.8679 g/cm3 (16.200009765625 °C)**
Melting point159-160 °C***
Index of Refraction1.497, Calc.*
Boiling point184 °C (760 Torr)****
Refractive index1.51924 (16.20 °C)**
Flash point56.7±0.0 °C, Calc.*
*Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)
**von Auwers, K.
***Copenhaver, J. W.
****Kutz, W. M.
Safety Data
Hazard Symbolssymbol symbol symbol symbol symbol   GHS02;GHS05;GHS07;GHS08;GHS09 Danger  Details
Risk StatementsH226-H304-H315-H318-H411  Details
Safety StatementsP210-P233-P240-P241-P242-P243-P264-P264+P265-P273-P280-P301+P316-P302+P352-P303+P361+P353-P305+P354+P338-P317-P321-P331-P332+P317-P362+P364-P370+P378-P391-P403+P235-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Flammable liquidsFlam. Liq.3H226
Skin irritationSkin Irrit.2H315
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Aspiration hazardAsp. Tox.1H304
Serious eye damageEye Dam.1H318
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Acute toxicityAcute Tox.4H332
Acute toxicityAcute Tox.4H302
Chronic hazardous to the aquatic environmentAquatic Chronic4H413
Transport InformationUN 2049 3 / PGIII
SDSAvailable
up Discovery and Applications
1,4-Diethylbenzene, also known as para-diethylbenzene, is an organic compound with the chemical formula C10H14. It consists of a benzene ring with two ethyl groups attached at the 1 and 4 positions. This compound is a colorless liquid at room temperature and is insoluble in water but soluble in organic solvents. 1,4-Diethylbenzene is used in various industrial applications, although it is less well-known than some other alkylated benzenes.

The synthesis of 1,4-diethylbenzene typically involves the Friedel-Crafts alkylation of benzene with ethylene in the presence of a catalyst, such as aluminum chloride or ferric chloride. This process leads to the formation of the ethylated benzene in high yields. The reaction conditions are designed to favor the para-ethylation, resulting in the selective formation of 1,4-diethylbenzene over other positional isomers, such as 1,2-diethylbenzene or 1,3-diethylbenzene.

One of the primary applications of 1,4-diethylbenzene is as a solvent in various chemical processes. Its high solvency power for resins, oils, and other organic materials makes it suitable for use in paints, coatings, adhesives, and varnishes. As a solvent, it helps improve the application properties of these materials, such as flow and spreadability.

1,4-Diethylbenzene is also used in the production of other chemicals. It serves as a precursor in the synthesis of several aromatic compounds and is involved in the preparation of certain pharmaceuticals and agrochemicals. Its utility as an intermediate compound arises from its ability to undergo various chemical reactions, including alkylation and oxidation, to form a variety of derivatives that are valuable in industrial and research settings.

In addition, 1,4-diethylbenzene is a component of gasoline, where it may contribute to the overall performance and characteristics of the fuel. However, its presence in gasoline has led to concerns regarding air pollution and its potential impact on the environment and human health. Studies have been conducted to monitor and assess its emissions during combustion processes.

From an environmental and health perspective, 1,4-diethylbenzene is considered a volatile organic compound (VOC). Its release into the atmosphere can contribute to the formation of ground-level ozone and other pollutants, which can have adverse effects on air quality and human health. As a result, its levels in industrial emissions and gasoline are regulated in many regions.

In summary, 1,4-diethylbenzene is an important chemical in industrial applications, particularly as a solvent and intermediate in the synthesis of other compounds. Its production is primarily achieved through the Friedel-Crafts alkylation of benzene, and it finds use in the production of resins, adhesives, and some chemicals. Although it is a relatively minor constituent of gasoline, it is subject to environmental monitoring due to its potential to contribute to air pollution.

References

2024. Ester-functionalized pillar[6]arene as the gas chromatographic stationary phase with high-resolution performance towards the challenging isomers of xylenes, diethylbenzenes, and ethyltoluenes. Analytical and Bioanalytical Chemistry, 416(5).
DOI: 10.1007/s00216-024-05146-7

2024. Effects of the Type and Loading of Rare-Earth Metals (Pr, Yb, Ho) on the para-Selectivity of HTsVM Zeolite in Toluene Ethylation. Petroleum Chemistry, 64(2).
DOI: 10.1134/s0965544124010134

2023. Process-specific volatile organic compounds emission characteristics, environmental impact and health risk assessments of the petrochemical industry in the Beijing-Tianjin-Hebei region. Environmental science and pollution research international, 30(60).
DOI: 10.1007/s11356-023-31351-5
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