cyclic anhydride reaction with alcohol

A few 3-acyl-4-hydroxy-2H-pyran-2-ones were obtained by palladium(II)-catalyzed carbonylation of aliphatic and aromatic α-chloroketones, through the formation of an acylketene and dimerization by a [4 + 2] cycloaddition reaction (Scheme 36) (15TL2773). Sulphuric acid or concentrated phosphoric acid are normally used acid Presumably a redox reaction generates the radicals required. A comparison of Examples 1 and 8 shows that a halfester of ethylene-maleic anhydride copolymers (Example 8) will not function in accordance with the teachings of this invention to reform the alcohol and the cyclic acid anhydride at temperatures greater than 80 C. while removing the alcohol as formed, whereas half-esters of the higher carbon number alpha olefin-maleic anhydride copolymers will (Example 1). Contributors. thereafter admixing said copolymer product while in solution with a monohydroxy aliphatic alcohol having from 1 to 4 carbon atoms, the amount of said alcohol being sufficient and the rate of addition of said copolymer solution being such as to result in precipitation of the copolymer in a particulate solid form. This catalyst system is widely applicable to the copolymerization of phthalic anhydride and unsubstituted, monosubstituted and disubstituted epoxides as listed below: Aluminum porphyrin (4) was originally found to be a very effective catalyst for the ‘living’ polymerization of epoxide (equation 2) and β-lactone (equation 3), which proceeds via (porphinato)aluminum alkoxide (5) and carboxylate (6), respectively, as the growing species.7,8 On the other hand, the copolymerization of epoxide and cyclic acid anhydride by aluminum porphyrin alone proceeds very slowly, and the product contains a considerable amount of ether linkages. Thus, partially esterified ethylenemaleic anhydride copolymers and partially esterified vinyl chloride-maleic anhydride copolymers internally crosslink when subjected to temperatures in excess of 80 C. EXAMPLE 14 A maleic anhydride-l-octadecene copolymer was prepared by adding 303 grams (1.2 moles) of l-octadecene to a reaction mixture consisting of 200 grams (1.8 moles) of propylene dichloride, 58.8 grams (0.6 mole) of maleic anhydride, and 1.5 grams (0.006 mole) of benzoyl peroxide. The organic compound must therefore have at least eight carbon atoms, and at least four carbon atoms in a straight chain and the carbonyl groups of the acid and ester functions of the half-ester groups must be directly attached to adjacent internal aliphatic carbon atoms. The results of this series of runs are shown on Table I below. Nonisothermal curing studies by differential scanning calorimetry (DSC) have suggested that both the curing reaction of epoxide with the rosin anhydride and the curing reaction of rosin epoxide with aniline were autocatalytic, and the cure reactions were similar to the respective conventional epoxy resin systems. For example, the copolymerization of 1,2-epoxypropane (1; R1 = Me and R2 = R3 = R4 = H) and phthalic anhydride (25 equiv./25 equiv.) Alternatively one mole of aluminum chloride and one mole of alkylaluminum chloride may be used. Further polyfunctionalized derivatives were achieved through enantioselective formal [3 + 3] cycloaddition reaction of α,β-unsaturated N-acyltriazoles with 1,3-diketones (Scheme 38) (15CC14628) and asymmetric Michael addition of α,β-disubstituted enals with 1,3-diketones (15CC4473), mediated by NHC catalysts. [29], The obtained copolymers show properties that that suggests a potential use as biomaterials for therapeutic systems and prostheses. of hexene-l and 2940 grams of maleic anhydride were reacted in 13,500 cc. The reaction product which comprises an organic compound comprising at least one half-ester group and one diester group can then be heated in accordance with the invention at a temperature in excess of about 80 C. to convert the half-ester groups to a cyclic anhydride group and a by-product alcohol corresponding to the alcohol portion of said half-ester group.

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