Benzoyl chloride

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Not to be confused with benzyl chloride.
Benzoyl chloride
Names
IUPAC name
Benzoyl chloride
Other names
Benzenecarbonyl chloride
Benzoylchloride
α-Chlorobenzaldehyde
Properties
C7H5ClO
C6H5COCl
Molar mass 140.57 g/mol
Appearance Colorless fuming liquid
Odor Pungent, aromatic, almond-like
Density 1.211 g/cm3 (25 °C)
Melting point −1 °C (30 °F; 272 K)
Boiling point 197.2 °C (387.0 °F; 470.3 K)
Reacts
Solubility Reacts with alcohols, amines, bases
Miscible with benzene, carbon disulfide, ethers, halocarbons
Vapor pressure 0.4 mmHg (20 °C)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 72 °C (162 °F; 345 K)
Lethal dose or concentration (LD, LC):
1,900 mg/kg (rat, oral)
Related compounds
Related compounds
Acetyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl.

Properties

Chemical

Benzoyl chloride hydrolyzes in water or basic solutions.

Benzoyl chloride reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give amides. Condensation with diethylamine for example, yields N,N-diethylbenzamide.

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.[1]

Treating benzoyl chloride with hydrogen peroxide and sodium hydroxide yields benzoyl peroxide.[2]

Physical

Benzoyl chloride is a colorless fuming liquid, with a pungent aromatic odor. It reacts with water and other protic solvents.

Availability

Benzoyl chloride is sold by chemical suppliers.

Preparation

Benzoyl chloride is produced by reacting benzotrichloride with water or benzoic acid:[3]

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

It can also be produced by the direct chlorination of benzaldehyde (Preparation of organic compounds, E. de. Barry Barnett, 52, 1912)[4]

As with other acyl chlorides, it can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride or oxalyl chloride.[5][6]

Chlorination of benzyl alcohol is another possible route.[7]

Projects

  • Preparation of benzoyl peroxide
  • Make benzoate esters
  • Make benzamides
  • Preparation of more volatile acyl chlorides [8]

Handling

Safety

Benzoyl chloride is harmful, corrosive and lachrymator. Proper protection must be worn when handling the compound, such as thick gloves, gas mask, an apron and always keep a neutralizing agent nearby.

Storage

In closed bottles, away from bases and people.

Disposal

Can be neutralized by adding it in cold water or crushed ice. Sodium hydroxide may be added to fully hydrolyze the compound to sodium benzoate.

References

  1. http://orgsyn.org/demo.aspx?prep=CV2P0520
  2. https://www.fao.org/fileadmin/templates/agns/pdf/jecfa/cta/63/Benzoylperoxide.pdf
  3. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a03_555
  4. https://www.prepchem.com/synthesis-of-benzoyl-chloride/
  5. https://www.prepchem.com/synthesis-of-benzoyl-chloride/
  6. https://babel.hathitrust.org/cgi/pt?id=hvd.hxdg3f&view=1up&seq=6
  7. https://patents.google.com/patent/US1851832
  8. https://pubs.acs.org/doi/10.1021/ja01273a014

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