Benzoyl chloride

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Not to be confused with benzyl chloride.
Benzoyl chloride
Benzoyl Chloride
Benzoyl-chloride-3D-balls.png Benzoyl-chloride-3D-vdW.png
Identifiers
CAS number 98-88-4 YesY
PubChem 7412
ChemSpider 7134 YesY
KEGG C19168 YesY
RTECS number DM6600000
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H5ClO
Molar mass 140.57 g mol−1
Appearance colorless liquid
Density 1.21 g/mL, liquid
Melting point −1 °C (30 °F; 272 K)
Boiling point 197.2 °C (387.0 °F; 470.3 K)
Solubility in water reacts
Hazards
MSDS Oxford MSDS
EU classification Toxic T Corrosive C
R-phrases R34
S-phrases (S1/2) S26 S45
Flash point 72 °C (162 °F; 345 K)
Related compounds
Related compounds benzoic acid, benzoic anhydride, benzaldehyde
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the production of dyes, perfumes, pharmaceuticals, and resins.

Preparation[edit]

Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:[1]

C6H5CCl3 + H2O → C6H5COCl + 2 HCl
C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl

As for other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride or thionyl chloride. It was first prepared by treatment of benzoic acid with chlorine.[2]

Reactions[edit]

Benzoyl chloride is a typical acyl chloride. It reacts with alcohols and amines to give the corresponding esters and amides. It undergoes the Friedel-Crafts acylation with arenes to give the corresponding benzophenones. Similarly, it reacts with water to produce hydrochloric acid and benzoic acid:

C6H5COCl + H2O → C6H5CO2H + HCl

Benzoyl peroxide is industrially synthesised by reacting benzoyl chloride with hydrogen peroxide and sodium hydroxide:[3]

2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O

References[edit]

  1. ^ Takao Maki, Kazuo Takeda “Benzoic Acid and Derivatives” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a03_555
  2. ^ Friedrich Wöhler, Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 249–282. doi:10.1002/jlac.18320030302. 
  3. ^ El-Samragy, Yehia (2004). Chemical and Technical Assessment (PDF). "Benzoyl Peroxide". 61st JECFA (Technical report) (Joint FAO/WHO Expert Committee on Food Additives): 1. Retrieved 31 October 2013. 

External links[edit]