ε-Caprolactone or caprolactone - lactone (cyclic ether ), with a seven-membered ring. Its name comes from caproic acid . This colorless liquid, miscible with most organic solvents and water, is produced on a large scale as a precursor for caprolactam and polycaprolactone polymers.
| Caprolactone | |
|---|---|
 | |
| Are common | |
| Systematic name | 2-oxepanone |
| Traditional names | epsilon-caprolactone, 6-hexanololactone, hexano-6-lactone, 1-oxa-2-oxocycloheptane |
| Chem. formula | C 6 H 10 O 2 |
| Physical properties | |
| condition | liquid |
| Molar mass | 114.14 g / mol g / mol |
| Density | 1,030 g / cm³ |
| Thermal properties | |
| T. melt. | -1 ° C |
| T. Kip. | 241 ° C ° C |
| Chemical properties | |
| Water solubility | mixes up |
| Classification | |
| Reg. CAS number | 502-44-3 |
| Pubchem | |
| Reg. EINECS number | |
| SMILES | |
| Inchi | |
| CHEBI | 17915 |
| Chemspider | |
Content
Production and Application
The vast majority of caprolactone, often produced locally, is used as a precursor for caprolactam [1] . It is also a monomer used in the manufacture of highly specialized polymers . For example, its ring-opening polymerization yields polycaprolactone [2] . Another polymer is monocryl , used as a suture material in surgery [3] .
In industry, caprolactone is produced by the oxidation of cyclohexanone with peracetic acid according to . The three main manufacturers are BASF in the USA, Daicel in Japan and the largest, Perstorp , in Sweden.
Chemical Properties
The main use of caprolactone is the production of polycaprolactones. They fall into two categories: low molecular weight polyols based on polycaprolactone used in special polyurethanes and coatings, and high molecular weight thermoplastics used in various fields. It is also known that millions of tons of caprolactone are converted to caprolactam annually, however, using a different technology [4] .
Carbonylation of caprolactone after hydrolysis gives pimelic acid . The lactone ring easily opens in the presence of nucleophiles, including alcohols and water, with the formation of various polylactones and, as a result, 6-hydroxyadipic acid .
Related Compounds
Several other caprolactones are also known, however, they do not find such technological applications as ε-caprolactone. These isomers include alpha, beta, gamma, delta caprolactones. They all have chirality . Gamma-caprolactone is a component of floral aromas and insect pheromones [5] Delta-caprolactone is found in heated milk fat. [6] .
Security
Caprolactone is rapidly hydrolyzed and the resulting hydroxycarboxylic acids are toxic, like other representatives of this class of compounds [7] . They cause severe eye irritation. Prolonged exposure can damage the cornea.
Links
- ↑ Josef Ritz, Hugo Fuchs, Heinz Kieczka, William C. Moran “Caprolactam” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. DOI : 10.1002 / 14356007.a05_031
- ↑ Horst Köpnick, Manfred Schmidt, Wilhelm Brügging, Jörn Rüter, Walter Kaminsky “Polyesters” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. DOI : 10.1002 / 14356007.a21_227
- ↑ glycolide E-caprolactone copolymer Summary Report | Curehunter
- ↑ https://www.perstorp.com/en/products/plastic_materials/polyurethane_elastomers?
- ↑ Leading reference: M. Teresa Nunez, Victor S. Martin (1990), Efficient oxidation of phenyl groups to carboxylic acids with ruthenium tetraoxide.
- ↑ Thomas H. Parliament, Wassef W. Nawar and Irving S. Fagerson (1965), Delta-Caprolactone in Heated Milk Fat Journal of Dairy Science Vol. 48 No. 5 pages 615-616.
- ↑ Karlheinz Miltenberger “Hydroxycarboxylic Acids, Aliphatic” in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. DOI : 10.1002 / 14356007.a13_507