24980-41-4

Usage

Uses

Used in Medical Devices and Tissue Engineering:
POLYCAPROLACTONE AVERAGE MN CA. 42 500 is used as a material for the fabrication of research medical devices and research tissue engineering solutions, such as orthopedic or soft tissue fixation devices. It is chosen for its ability to be safely resorbed by the body after implantation.
Used in Extrusion Aids and Lubricants:
In the manufacturing industry, POLYCAPROLACTONE AVERAGE MN CA. 42 500 is used as an extrusion aid, die lubricant, mold release, pigment and filler dispersion aid, and polyester segments in urethanes and block polyesters.
Used in Tissue Engineering Scaffolds:
In the field of tissue engineering, POLYCAPROLACTONE AVERAGE MN CA. 42 500 is used as a material for creating tissue engineering scaffolds, providing a supportive structure for cell growth and tissue regeneration.
Used in 3D Bioprinting:
This polymer is utilized in 3D bioprinting as a material for creating three-dimensional structures with precise control over the spatial arrangement of cells and biomaterials.
Used in Drug Delivery Applications:
POLYCAPROLACTONE AVERAGE MN CA. 42 500 is used in drug delivery applications, particularly for sustained release formulations, due to its controlled degradation rate and biocompatibility.
Used in Research Applications:
This material is widely used in research applications, including tissue engineering, 3D bioprinting, and drug delivery, due to its favorable properties such as biodegradability, low melting point, and high solubility in organic solvents.

InChI:InChI=1/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2

Upstream product

• 109-99-9 tetrahydrofuran 
• 463-51-4 Ketene 
• 1191-25-9 6-Hydroxyhexanoic acid 
• 626-86-8 adipinic acid monoethyl ester 
• 79-21-0 peracetic acid 
• 108-94-1 cyclohexanone 
• 93-59-4 Perbenzoic acid 
• 2311-91-3 monoperoxyphthalic acid 
• 98-11-3 benzenesulfonic acid 
• 943-39-5 4-nitroperbenzoic acid 
• 932-92-3 cyclohexyl ethyl ether 
• 183-84-6 Cyclohexanone diperoxide 
• 72037-38-8 ε-thionovalerolactone 
• 4224-70-8 6-bromohexanoic acid 

Downstream Products

• 1577-22-6 5-hexenoic acid 
• 39979-08-3 methyl 7-aminoheptanoate 
• 14273-90-6 methyl 6-bromohexanoate 
• 1117-66-4 7-aminoheptanoic acid ethyl ester 
• 34176-76-6 6-Bromhexansaeure-trimethylsilylester 
• 66241-83-6 6-Phenylselanyl-hexanoic acid 
• 67654-81-3 10-Hydroxy-1-trityloxy-dec-3-yn-5-one 
• 15985-49-6 6-[[(diphenylmethylene)amino]oxy]hexanoic acid 
• 58241-40-0 5-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-pentan-1-ol 
• 67654-87-9 6-Hydroxy-hexanoic acid 6-oxo-8-phenyl-oct-7-ynyl ester 
• 65850-99-9 7-(Toluene-4-sulfonyl)-heptane-1,6-diol 
• 92031-08-8 7-Amino-heptansaeure-cyclohexylester 
• 1694-83-3 6-hydroxyhexanoic hydrazide 
• 25177-65-5 6-(indol-3'-yl)hexanoic acid 

Relevant academic research and scientific papers

Baeyer-Villiger oxidation of ketones catalysed by rhenium complexes bearing N- or oxo-ligands

Rhenium (I, III-V or VII) complexes bearing N-donor or oxo-ligands catalyse the Baeyer-Villiger oxidation of cyclic and linear ketones (e.g. 2-methylcyclohexanone, 2-methylcyclopentanone, cyclohexanone, cyclopentanone, cyclobutanone and 3,3-dimethyl-2-butanone) into the corresponding lactones or esters, in the presence of aqueous H2O2 (30%). The effects of various reaction parameters are studied allowing to achieve yields up to 54%.

A novel method for epoxidation of cyclohexene catalyzed by Fe2O3 with molecular oxygen and aldehydes

A novel method for the epoxidation of cyclohexene using molecular oxygen (latm) and aldehyde in the presence of Fe2O3 is presented. The yields of epoxide highly increased by using this method.

Oxaziridine-mediated catalytic hydroxylation of unactivated 3° C-H bonds using hydrogen peroxide

The design, structural characterization, and evaluation of a unique class of 1,2,3-benzoxathiazine-based oxaziridines as potent O-atom transfer agents for catalytic C-H hydroxylation and alkene epoxidation are described. Turnover of this reaction is made possible by employing a diaryl diselenide cocatalyst and urea·H2O2 as the terminal oxidant. Oxidation of saturated hydrocarbons is strongly biased toward 3° C-H bonds even in systems possessing a significantly greater number of methylene groups. In addition, the benzoxathiazine catalyst is effective for epoxidation of terminal and electron-deficient olefins. Collectively, these findings represent an important first step toward the advancement of general methodology for selective C-H oxidation. Copyright

Phase Transfer Catalyzed Oxidation of Ketones with Borax - H2O2

Borax forms peroxy species when dissolved in 30percent hydrogen peroxide which can be transferred into the organic phase when biphase mixtures are agitated.The addition of a catalytic amount of BTEAC promotes the transfer.This biphase system was used for the Baeyer-Villiger oxidation of several ketones insoluble in water.Effects of changing various parameters, e.g. temperature, time, amount of H2O2 etc. were investigated.At higher temperature (ca. 80 deg C), 100percent conversion could be achieved in 2-4 h.The results show that under appropriate conditions this reaction is of synthetic value for the oxidation of acid-sensitive ketones using inexpensive and easily available reagents. - Keywords: Baeyer-Villiger oxidation; Phase transfer catalysis; Borax-H2O2 system

Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex

The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N?bis(2?pyridylmethyl)?1,2?di(2?pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclohexanone and the oxoiron(IV) species. The second order rate constant is smaller by one order of magnitude than that obtained for the related achiral [FeIV(N4Py)(O)]2+ complex. Oxidation of 4-substituted cyclohexanone derivatives by the chiral oxoiron(IV) complex attains moderate enantioselectivities up to 45% enantiomeric excess (ee).

An alternative approach towards poly-ε-caprolactone through a chemoenzymatic synthesis: Combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates

A novel synthetic route towards the polymer poly-ε-caprolactone based on a chemoenzymatic reaction sequence was developed. Initial hydrogenation of phenol to cyclohexanol gave a crude product, which was directly used without work-up for a subsequent biocatalytic double oxidation towards ε-caprolactone by means of an alcohol dehydrogenase and a monooxygenase. In order to overcome product inhibition effects, an in situ-product removal strategy via extraction of ε-caprolactone from an aqueous reaction medium with an organic solvent in the presence of a permeable polydimethylsiloxane membrane was applied. Furthermore, this in situ-product removal was combined with lipase-catalyzed polymerization in the organic phase at 25 °C. The obtained crude product contained a polymer fraction with a degree of polymerization comparable to commercial poly-ε-caprolactone.

An Alcohol Dehydrogenase from the Short-Chain Dehydrogenase/Reductase Family of Enzymes for the Lactonization of Hexane-1,6-diol

Biocatalytic production of lactones, and in particular ?-caprolactone (CL), have gained increasing interest as a greener route to polymer building blocks, especially through the use of Baeyer–Villiger monooxygenases (BVMOs). Despite several advances in the field, BVMOs, however, still suffer several practical limitations. Alcohol dehydrogenase (ADH)-mediated lactonization of diols in turn has received far less attention and very few enzymes have been identified for the conversion of diols to lactones, with horse-liver ADH (HLADH) remaining the catalyst of choice. Screening of a diverse panel of ADHs, AaSDR-1, a member of the short-chain dehydrogenase/reductase family, was found to produce ?-caprolactone from hexane-1,6-diol. Moreover, cofactor regeneration by an NADH oxidase eliminated the requirement of co-substrates, yielding water as the sole by-product. Despite lower turnover frequencies as compared to HLADH, higher selectivity was found for the production of CL, with HLADH forming significant amounts of 6-hydroxyhexanoic acid and adipic acid through aldehyde dehydrogenation/oxidation of the gem-diol intermediates. Also, CL yield were shown to be dependent on buffer choice, as structural elucidation of a Tris adduct confirmed the buffer amine to react with aliphatic aldehydes forming a Schiff-base intermediate which through further ADH oxidation, forms a tricyclic acetal product.

Kinetics Modeling of a Convergent Cascade Catalyzed by Monooxygenase-Alcohol Dehydrogenase Coupled Enzymes

A convergent cascade reaction coupling a cyclohexanone monooxygenase variant and an alcohol dehydrogenase to make ?-caprolactone from cyclohexanone and 1,6-hexanediol was characterized via progress curve analysis with two kinetic models developed iteratively. A chemical side reaction occurring with the utilized Tris buffer and consequent byproduct formations were considered in Model 2, which reduced the root-mean-square error (RMSE) values by half, compared to Model 1 (RMSE values of 13%-40%). The optimized model, Model 2, led us to simulate the cascade reaction including 22 kinetic parameters with a maximum RMSE value in the range of 10%-21%.

Combined H2O2/nitrile/bicarbonate system for catalytic Baeyer-Villiger oxidation of cyclohexanone to ε-caprolactone over Mg–Al hydrotalcite catalysts

Magnesium-aluminium hydrotalcite-like compounds (Ht) with molar ratios of Mg/Al = 2, 3, 4 and 6, were synthesized and used as catalysts in the Baeyer-Villiger oxidation of cyclohexanone to ε-caprolactone. Oxidation was carried out in mild conditions (70 °C, atmospheric pressure) either with conventional H2O2/acetonitrile oxidizing mixture, or with a newly designed H2O2/acetonitrile/bicarbonate system. The presented results show clearly superiority of bicarbonate-containing setup, which provides a significant increase of the ε-caprolactone yield. The neutralizing effect of bicarbonate, strongly limiting leaching of magnesium from Ht, is considered the main cause of the improved catalytic performance.

The Baeyer-Villiger oxidation of ketones with bis(trimethylsilyl) peroxide in the presence of ionic liquids as the solvent and catalyst

A new method for lactone synthesis with bis(trimethylsilyl) peroxide as the oxidant and ionic liquids as solvents is reported. We propose two possibilities for the Baeyer-Villiger reaction course. The first of these is based on simply exchanging dichloromethane, the classical solvent for Baeyer-Villiger oxidation, for the ionic liquid bmimNTf2, which results in increased product yields. The second possibility is the elimination of the Baeyer-Villiger reaction catalyst and use of 1-butyl-3-methylimidazolium trifluoromethanesulfonate as both the solvent and catalyst. This method gives lactones in high yields with the possibility of ionic liquid recycling.