Properties of Cyclohexanone

Evaporation rote, approximate (toluene = 100) Flash point (open cup) 

Distillation range Purity Residue Water content 

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Ratkovics, F. Laszlo-Parragi, M. Measurements of vapor-liquid equilibria, densities, viscosities and dielectric properties of cyclohexanone + triethylamine mixtures with respect to keto-enol tautomerism. Fluid Phase Equilib. 1984, 17, 97-113. 

N.A. Donoghue, D.B. Norris, P.W. Trudgill, The purification and properties of cyclohexanone oxygenase from Nocardia globerula CLl and Acinetobacter NCIB 9871, Eur. J. Biochem. 63 (1976) 175-192. 

Reactions. The chemical properties of cyanoacetates ate quite similar to those of the malonates. The carbonyl activity of the ester function is increased by the cyano group s tendency to withdraw electrons. Therefore, amidation with ammonia [7664-41-7] to cyanoacetamide [107-91-5] (55) or with urea to cyanoacetylurea [448-98-2] (56) proceeds very easily. An interesting reaction of cyanoacetic acid is the Knoevenagel condensation with aldehydes followed by decarboxylation which leads to substituted acrylonitriles (57) such as (29), or with ketones followed by decarboxylation with a shift of the double bond to give P,y-unsaturated nitriles (58) such as (30) when cyclohexanone [108-94-1] is used. 

Important physical properties of cyclohexanol and cyclohexanone are shown ia Table 1. Cyclohexanol is miscible ia all proportions with most organic solvents, including those customarily used ia lacquers. It dissolves many oils, waxes, gums, and resias. 

Several cleaning formulations for specific uses contain unreacted polyamines. Examples include mixtures of ammonium alkylbenzenesulfonate, solvents, and PIP which give good cleaning and shine performance on mirrors and other hard surfaces without rinsing (305), and a hard-surface cleaner composed of a water-soluble vinyl acetate—vinyl alcohol copolymer, EDA, cyclohexanone [108-94-1] dimethyl sulfoxide [67-68-5] a surfactant, and water (306). TEPA, to which an average of 17 moles of ethylene oxide are added, improves the clay sod removal and sod antiredeposition properties of certain hquid laundry detergents (307). 

The aim of this study is to develop model reaction for the characterization of the acidity and basicity of various transition aluminas, the experimental conditions being close to that for catalysis use. Among various model reactions, the transformation of cyclopentanol and cyclohexanone mixture was chosen for this work. Indeed, this reaction was well known for estimating simultaneously the acid-base properties of oxide catalysts [1], Two reactions take place the hydrogen transfer (HT) on basic sites and the alcohol dehydration (DEH) on acid sites. The global reaction scheme is shown in Figure 1. 

Alumina is an amphoteric catalyst, which can difficult to characterize via chemical and physic methods. The transformation of cyclopentanol/cyclohexanone mixture allows us to estimate at the same time the acid-base properties of aluminas. From this transformation, it was shown that aluminas can be classified into two families only basic aluminas, such as theta, which were more basic than MgO, and acido-basic aluminas, eta, gamma and delta, which possess an acidic character less pronounced than dealuminated HMOR zeolite... 

Secundo, F., Zambianchi, F., Crippa, G., Carrea, G. and Tedeschi, G., Comparative study of the properties of wild type and recombinant cyclohexanone monooxygenase, an enzyme of synthetic interest. J. Mol. Catal. B Enzym., 2005, 34, 1. 

In 1987, the successful startup of a new process was announced for the production of 10,000 tons/year of catechol and hydroquinone by the selective oxidation of phenol with H202 catalyzed by TS-1 at the Enichem plant in Ravenna, Italy (Notari, 1988). Soon thereafter, it was disclosed that another new process for the production of cyclohexanone oxime from cyclohexanone, H202, and NH3 with TS-1 as the catalyst was being developed (Roffia et al., 1990).The fact that a material with unusual catalytic properties had been obtained was then finally recognized, and the interest in titanium-containing catalysts spread rapidly in the scientific community, especially in industrial research laboratories. In the meantime, the synthesis method was studied and described in more detail and when all the necessary precautions were taken, TS-1 was reproduced in other laboratories, as were the highly selective catalytic reactions. The subsequent work confirmed that Ti v can assume the tetrahedral coordination necessary for isomorphous substitution of SiIV and added valuable information about the structure, properties and catalytic performance of the material. New reactions catalyzed by TS-1 have been discovered, and new synthetic methods... 

There is, as is well known, a close similarity between the crystalline and porous structures of silicalite-1 and silicalite-2. The same similarity therefore exists between TS-1 and TS-2, and it appears logical that they should have very similar catalytic properties. TS-2 has been evaluated as a catalyst for many different reactions, such as Beckmann rearrangement of cyclohexanone oxime with vapor-phase reactants H202 oxidation of phenol, anisole, benzene, toluene, n-hexane, and cyclohexane and ammoximation of cyclohexanone. As described in detail in Section V.C.3, differences that had been claimed between the catalytic properties of TS-1 and those of TS-2 have not been substantiated. Later investigations have shown that, when all the relevant parameters are identical, the catalytic activities of TS-1 and TS-2 are also identical. The small differences in the crystalline structure between the two materials have no influence on their catalytic properties (Tuel et al., 1993a). 

Some physical properties of the main species are listed in Table 5.2. Bringing phenol in reaction conditions implies vaporization at low partial pressure. Vacuum is necessary for carrying out separations by distillation. Phenol forms azeotropes with both cyclohexanol and cyclohexanone. If unconverted phenol should be recycled this could affect the global yield by recycling desired product too. If water appears as a byproduct, it gives azeotropes with both cyclohexanone and cyclohexanol. Because these azeotropes are low boilers they can be removed easily by distillation. 

The rearrangement of cyclohexanone oxime to caprolactam is still an important step in nylon production, and the heterogeneously catalyzed Beckmann rearrangement has been extremely well investigated (4, 16-19). In order to obtain catalysts that couple a high lactam selectivity to long lifespan, careful tuning of the zeolite properties is required. Some important factors are ... 

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