Butyryl chloride

Butyryl chloride
Names
Preferred IUPAC name
Butanoyl chloride
Other names
Butyryl chloride
n-Butyryl chloride
C-4 Acyl halide
Identifiers
141-75-3 YesY
3D model (Jmol) Interactive image
ChemSpider 8523 YesY
ECHA InfoCard 100.004.999
EC Number 205-498-5
PubChem 8855
UN number 2353
Properties
C4H7ClO
Molar mass 106.55 g/mol
Appearance colorless
Odor pungent chloride ordor
Density 1.033g/cm3
Melting point −89 °C (−128 °F; 184 K)
Boiling point 102 °C (216 °F; 375 K)
decomposition
Solubility miscible with ether
1.412
Hazards
Main hazards Reacts violently with water, flammable, corrosive
R-phrases R11, R34
S-phrases (S1), (S2), S25, S36/37/39, S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
3
3
2
Flash point 21.7 °C (71.1 °F; 294.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Butyryl chloride (also known as n-Butyryl chloride, butanoyl chloride, or C-4 Acyl halide) is an organic compound with the chemical formula C4H7ClO. Butyryl chloride is liquid at room temperature, has a colorless to light yellowish appearance and has an extremely strong pungent odor. Butyryl chloride is soluble in almost all aprotic organic solvents, but it decomposes violently by heating and spontaneously decomposes when exposed to moist air or water to form pure hydrogen chloride gas. It also reacts violently when mixed with strong oxidants, metals (especially iron), alkali metals, alkali earth metals, bases and wide range of organic substances such as amines, dimethyl sulfoxide, and alcohols. These reactions tend to result in explosions and fire; hence extreme caution must be taken when mixing with other substances. Butyryl Chloride belongs in the group of acyl halides which are involved in acylation process that introduce an acyl group (RCO-) into compounds.

Reactions

Derivatives of butyryl chloride are used in manufacturing pesticides, pharmaceuticals, perfume fixative, polymerization catalyst, and dyestuffs. Butyryl chloride is also commonly used as an intermediate for organic synthesis for the preparation of pharmaceuticals, agrochemicals, dyes, esters, and peroxide compounds.[1]

Butyryl chloride is highly flammable and fumes in air. It decomposes exothermically in water to give corrosive hydrochloric acid. Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of Hydrogen Chloride gas will be created in 0.47 minutes.[2] May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts.[3]


Butyryl chloride belongs in the reactive groups:

•Acid Halides

•Sulfonyl Halides

•Chloroformates


Liquids classified within these reactive groups have been known to react with absorbent materials including:

•Cellulose-Based Absorbents

•Mineral-Based & Clay-Based Absorbents

•Dirt/Earth

Health concerns and disposal

The chemical, physical, and toxological properties of butyryl chloride have not been thoroughly investigated. Butyryl chloride is known to be toxic and symptoms of exposure include: burning sensation at site of contact, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.[4] Inhaling can result in death from spasms, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema.[5] It is extremely corrosive and destructive of tissues, especially mucous membranes, upper respiratory tract, eyes, and skin. Prolonged exposure and frequent contact is believed (but yet to be proven) to cause seizures and cancer.[6] If butyryl chloride is ingested, vomiting should not be induced.

In case of fire, CO2 or foam extinguishers should be used instead of water. In case of spillage butyryl chloride can neutralized with sodium carbonate (soda ash) or calcium hydroxide (slaked lime).[7][8]

References

  1. ↑ http://chemicalland21.com/specialtychem/perchem/N-BUTYRYL%20CHLORIDE.htm
  2. ↑ "Development of the Table of Initial Isolation and Protective Distances for the 2008 Emergency Response Guidebook", ANL/DIS-09-2, D.F. Brown, H.M. Hartmann, W.A. Freeman, and W.D. Haney, Argonne National Laboratory, Argonne, Illinois, June 2009.
  3. ↑ J. Haz. Mat., 1981, 4, 291.
  4. ↑ http://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/10/109614/109614-BULK_______ALDRICH__.pdf
  5. ↑ http://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/10/109614/109614-BULK_______ALDRICH__.pdf
  6. ↑ http://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/10/109614/109614-BULK_______ALDRICH__.pdf
  7. ↑ https://fscimage.fishersci.com/msds/97320.htm
  8. ↑ http://cameochemicals.noaa.gov/chris/BUC.pdf
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