CAPRO

Place 125 ml. of concentrated ammonia solution (sp. gr. 0-88) in a 600 ml. beaker and surround the latter with crushed ice. Stir the ammonia solution mechanically, and introduce the n-caproyl chloride slowly by means of a suitably supported separatory funnel with bent stem. The rate of addition must be adjusted so that no white fumes are lost. The amide separates immediately. Allow to stand in the ice water for 15 minutes after all the acid chloride has been introduced. Filter oflF the amide at the pump use the flltrate to assist the transfer of any amide remaining in the beaker to the Alter (2). Spread the amide on sheets of Alter or drying paper to dry in the air. The crude n-capro-amide (30 g.) has m.p. 98-99° and is sufficiently pure for conversion into the nitrile (Section 111,112) (3). Recrystallise a small quantity of the amide by dissolving it in the minimum volume of hot water and allowing the solution to cool dry on filter paper in the air. Pure n-caproamide has m.p. 100°. 

When prepared by thermal condensation of the respective alkoxides and carbonates in hydrocarbon media such as decalin, these catalysts yielded living poly-e-capro-lactone. Its living nature was demonstrated by the increase of DPn with conversion and by the validity of the relation... 

However, an almost classical attempt to generate an a, -unsaturated e-capro-lactam 87 involved a Knoevenagel condensation of 86 as the ring forming step. The material was employed in a synthesis of conformationally restricted analogs of some anti cancer agents (tetrahydrofolate analog) (Scheme 17) [24]. 

Davis, P. A. Nicolais, L., Ambrosio, L., and Huang, S. J., Synthesis and characterization of semi-interpenetrating polymer networks of poly(2-hydroxyethyl methacrylate) and poly(capro-lactone), Polym. Mater. Sci. Eng., 56, 536-540, 1987. 

Mantzos, L., Capros, P., Kouvarikatis, N. et al. (2003). European Energy and Transport - Trends to 2030. On behalf of the European Commission, DG TREN. Greece University of Athens. 

Figure 19.4. Greenhouse-gas emissions by broad sector in selected world regions 1993 and 2003 (own compilation based on EPA (2006) Mantzos and Capros (2006) MLIT (2006) UN (2007)).

Mantoz, L. and Capros, M. (2006). European Energy and Transport, Trend to 2030 - Update 2005. Report to the European Commission. Brussels. 

Pahnans et al. prepared 5 by the reaction of [RuCl2(p-cymene)]2 and 2-phenyl-2-aminopropionamide in the presence of potassium carbonate. They used 5 in an iterative tandem catalysis for the synthesis of chiral oligoesters. The enzymatic ring opening of 6-methyl-e-caprolactone was combined with ruthenium-catalyzed alcohol racemization to produce optically active oligomers of 6-methyl-e-capro-lactone [23] (Scheme 1.17). 

Reaction of Aldehydes with Ammonium Sulfide. An aldehyde (0.1 mol, e.g, acetaldehyde, propionaldehyde, butyraldehyde, capro-aldehyde) was added to a 20% aqueous solution of ammonium sulfide (50 ml) and the mixture was stirred for 3 h at room temperature. Then it was extracted with ether, the extract was washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The remaining liquid residue was analyzed by GC and GC-MS. 

The seemingly complex imidazolone (78-3) is in fact obtained in a single step by reaction of the amino-ester (78-1) with the iminoether (78-2) derived from capro-nitrile. The relatively acidic proton on the heterocyclic ring is next removed by reaction with sodium hydride. This anion is then alkylated with the same biphenyl-methyl bromide (77-2) that was used to prepare losartan to afford (78-4). The nitrile group is in this case converted to the tetrazole by means of tributyltin azide, a reagent that involves milder conditions than the traditional acidic medium used to generate hydrazoic acid. Thus, treatment of (78-4) with the tin reagent affords irbesartan (75-5) [82]. 

Anionic polymerization of -caprolactone has been studied in several laboratories and it was found that considerable amounts of oligomers were found as by-products.— — We have studied the formation of oligomers in the anionic polymerization of 6-capro-lactone by gpc technique.A In view of the very facile intra- and intermolecular transesterification reactions in this system- -, the product distribution seems very interesting to check the validity of the thermodynamic equilibrium. 

Successive addition of monomers to the end of macromolecular initiator is the usual technique for the synthesis of tailored blockcopolymers. Anionic polymerization of pivalolactone, a-pyrrolidone— and the NCA of T-methyl-D-glutamate -2 was started from the end group of a prepolymer consisting carboxylate group or acyl lactam group or amino group. Living polymer of C-capro-lactone was expected to be formed by the initiated polymerization from polymer carbanion under kinetic controlled condition. 

A photoreactive macromer consisting of the reaction product of poly(capro-lactone-co-lactide) and pentaerythritol ethoxylate was prepared by Chudzik et al. (3) and used as tissue implants. 

Phenol is a basic feedstock for the production of phenolic resins, bisphenol A, capro-... 

The reactions of TMSA (14) with aldehydes165 23° gives a-trimethylsiloxy-alkyl azides (246, 413-417) they are highly stable against hydrolysis and higher temperatures (Scheme 62). Thermolysis of the azides 246, 413-417 gives directly N-TMS-butyr- (246), valero- (413), capro- (414)-, isobutyr- (415)-, pival- (416) and trichloroacetamide (417), respectively. 

Table IV. Calculated and Experimental Solubilities (mg/ml) of Progesterone and Naltrexone in Water, Poly(e-capro-lactone) and Poly(ethylene-co-vinyl acetate)...

NH3 or RNH2 or R2NH Amide formation from carboxylic acid derivatives (mild) or from carboxylic acids (A technical synthesis of nylon-6,6) transamidation [capro-lactame —> nylon-6 (perlon)] Peptide synthesis (Section 6.4.3)... 

Trade Name(s) D Capros (Rhone-Poulenc MXL (Napp as sulfate) MS Contin (Shionogi as... 

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