Chemistry:Cyclohexyl acetate

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Cyclohexyl acetate
Cyclohexyl acetate molecule
Names
IUPAC name
Cyclohexyl acetate[1]
Other names
  • Acetoxycyclohexane[1]
  • Acetic acid, cyclohexyl ester[1]
  • Hexalin acetate[1]
  • Cyclohexanol acetate[1]
  • Cyclohexane acetate[1]
  • Cyclohexanyl acetate[1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 210-736-6
KEGG
UNII
UN number 2243
Properties
CH
3COOC
6H
11
Molar mass 142.198 g·mol−1
Appearance Colorless liquid[1]
Odor Fruity, sweet, banana or apple[2]
Density 0.966 g/cm3[3]
Melting point −77 °C (−107 °F; 196 K)[4]
Boiling point 173 °C (343 °F; 446 K)[4]
Insoluble[1];
1.56 g/l[2]
Solubility Miscible with diethyl ether.[4]
Solubility in ethanol 580.47 g/l[2]
Solubility in methanol 769.91 g/l[2]
Solubility in isopropanol 596.92 g/l[2]
Vapor pressure
  • 14.6 hPa at 25 °C
  • 35 hPa at 50 °C
  • 60 hPa at 65 °C
  • [5]
1.439[4]
Hazards
Main hazards Highly flammable, eye and respiratory tract irritation
GHS pictograms GHS02: FlammableGHS07: Harmful
GHS Signal word Warning
HH226Script error: No such module "Preview warning".Category:GHS errors, HH315Script error: No such module "Preview warning".Category:GHS errors
PP210Script error: No such module "Preview warning".Category:GHS errors, PP233Script error: No such module "Preview warning".Category:GHS errors, PP240Script error: No such module "Preview warning".Category:GHS errors, PP241Script error: No such module "Preview warning".Category:GHS errors, PP242Script error: No such module "Preview warning".Category:GHS errors, PP243Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP303+P361+P353Script error: No such module "Preview warning".Category:GHS errors, PP370+P378Script error: No such module "Preview warning".Category:GHS errors, PP403+P235Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors
Flash point 58 °C (136 °F; 331 K)[4]
330 °C (626 °F; 603 K)
Lethal dose or concentration (LD, LC):
  • 6.73 g/kg (rat, oral)
  • 10.1 g/kg (rabbit, dermal)
  • [1]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclohexyl acetate is an organic compound with the chemical formula CH
3COOC
6H
11. It is a colorless liquid with a fruity, sweet, banana or apple odor. It is the cyclohexyl ester of acetic acid.

Synthesis

Cyclohexyl acetate can be synthesized by esterification reaction between acetic acid and cyclohexanol at elevated temperature with trace amounts of sulfuric acid as a catalyst[1][6] or by reaction of cyclohexene with acetic acid.[7]

Occurrence

Cyclohexyl acetate has been reported in Glycine max (soybean), Malus pumila (paradise apple), Garcinia dulcis, Mangifera indica (mango), Malus domestica (apple), Allium cepa (onion), Allium fistulosum (Welsh onion), Brassica (cabbage family) and even in Homo sapiens (human).[1]

Uses

Cyclohexyl acetate is used as a solvent and in making rubber. It is a powerful solvent for nitrocellulose and other cellulose esters, many resins, gums. It is also used leather industry for improving adhesion of leather varnishes. In the food industry, it is used as a flavoring agent.[1] Can be used as a paint solvent.[4] Cyclohexyl acetate is used as a fragrance in cosmetics and cleaning agents.[8]

Safety

Vapors of cyclohexyl acetate are much heavier than air and may be narcotic in high concentrations. Vapors are heavier than air and may travel to the source of ignition and flash back. Vapor may form explosive mixtures with air. The lower explosive limit (LEL) is 0.9 vol% (54 g/m3). It is skin, eye and respiratory tract irritant. May cause drowsiness, lowered consciousness and unconsciousness upon vapor inhalation or ingestion of large quantities, but it is safe when used as a flavoring agent. Cyclohexyl acetate emits acrid smoke and irritating fumes when heated to high temperatures. Containers of cyclohexyl acetate may explode when heated.[1] Do not spill into drains because of risk of explosion.[3]

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 PubChem. "Cyclohexyl acetate". https://pubchem.ncbi.nlm.nih.gov/compound/Cyclohexyl-acetate. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 scent.vn. "Cyclohexyl Acetate". https://scent.vn/en/pages/compound/cyclohexyl-acetate-12146. 
  3. ↑ 3.0 3.1 Sigma-Aldrich. "Cyclohexyl acetate". https://www.sigmaaldrich.com/GB/en/sds/aldrich/246514. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Chemical Book. "Cyclohexyl acetate". https://www.chemicalbook.com/ProductDetail_EN_cyclohexyl-acetate_2477870.htm. 
  5. ↑ GESTIS substance database. "Cyclohexyl acetate". https://gestis.dguv.de/data?name=037440. 
  6. ↑ Yadav, Ganapati D.; Mehta, Pranav H. (September 1, 1994). "Heterogeneous Catalysis in Esterification Reactions: Preparation of Phenethyl Acetate and Cyclohexyl Acetate by Using a Variety of Solid Acidic Catalysts". Industrial & Engineering Chemistry Research 33 (9): 2198–2208. doi:10.1021/ie00033a025. https://doi.org/10.1021/ie00033a025. 
  7. ↑ Hu, Yabo; Wang, Le; Lu, Jiawei; Ding, Lianghui; Zhang, Guowen; Zhang, Zhuxiu; Tang, Jihai; Cui, Mifen et al. (11 April 2023). "Novel Reactive Distillation Process for Cyclohexyl Acetate Production: Design, Optimization, and Control". ACS Omega 8 (14): 13192–13201. doi:10.1021/acsomega.3c00469. ISSN 2470-1343. PMID 37065013. 
  8. ↑ Bhatia, S. P.; Letizia, C. S.; Api, A. M. (December 1, 2008). "Fragrance material review on cyclohexyl acetate". Food and Chemical Toxicology 46 (12, Supplement): S52–S55. doi:10.1016/j.fct.2008.09.033. https://www.sciencedirect.com/science/article/pii/S0278691508005218. 



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