36366-93-5Relevant articles and documents
PROCESS FOR THE CONTINUOUS PRODUCTION OF HIGH PURITY PHENOLIC GLYCOL ETHER
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Page/Page column 13-15, (2009/07/17)
Phenolic glycol ethers, e.g., ethylene glycol phenyl ether, are prepared by a continuous, nonaqueous process comprising the steps of (A) contacting under isothermal reactive conditions in a first reactor or reaction zone an alkylene oxide, e.g., ethylene oxide, with (i) a stoichiometric molar excess of a phenolic compound, e.g., phenol, and (ii) a catalytic amount of a base, e.g., sodium hydroxide, homogeneously dispersed throughout the phenolic compound, to form a first intermediate phenolic glycol ether product, (Bj transferring the first intermediate phenolic glycol ether product to a second reactor or reaction zone, and ( C) subjecting the first intermediate phenolic glycol ether product to adiabatic reactive conditions in the second reactor or reaction zone to form a second intermediate phenolic glycol ether product comprising phenolic glycol ether, unreacted phenolic compound, catalyst, water and byproduct glycols. In addition, the mono-/di-product weight ratio can be adjusted by increasing or decreasing the amount of base catalyst employed.
SELECTIV BROMINATION OF THE AROMATIC RING IN ω-PHENYLPOLYOXAALKANES AND ALKANOLS IN MICELLES
Jursic, Branko
, p. 1553 - 1558 (2007/10/02)
The regioselecticity of bromination of ω-phenylpolyoxaalkanes and alkanols by bromine in aqueous solution of dodecyl sulfate (SDS) and aqueous solution of cetyltrimethylammonium bromide (CTAB) are shown to be related to the average orientation of substrate as indicated by 1H NMR studies.Thus ortho-bromination is promoted at higher concentrations of the surfactant relative to pure water.In contrast, at an equal ratio of the surfactant and substrate para-bromination is promoted.The results are discussed with respect to the average orientation of substrate in a micellar microenvironment and the formation of an ether-bromine comples as possible bromination agent.
Phase-Transfer-Catalyzed Gomberg-Bachmann Synthesis of Unsymmetrical Biarenes: A Survey of Catalysts and Substrates
Beadle, James R.,Korzeniowsky, Stephen H.,Rosenberg, David E.,Garcia-Slanga, Blanche J.,Gokel, George W.
, p. 1594 - 1603 (2007/10/02)
Two problems have hindered the Gomberg-Bachmann (GB) and Pschorr reactions of arenediazonium cations: the instability of the arenediazonium salts and side reactions.Arenediazonium tetrafluoroborate and hexafluorophosphate salts can be prepared in high yield and purity and can be stored safely.Unfortunately, these salts are insoluble in most nonpolar organic solvents.Crown ether complexation or other phase-transfer (pt) catalytic methodology can ameliorate this situation, and reactions conducted by the approaches outlined herein often afforded coupling or cyclization products in high yield and corresponding purity.The use of crown ethers, quarternary 'onium salts, lipophilic carboxylic acid salts, and even the polar cosolvent acetonitrile increase the utility of the ptGB reaction dramatically.Sixty examples of couplings are reported along with an assessment of selectivities.A number of examples are also presented of phase-transfer-type Pschorr cyclizations.In the latter case, the use of potassium superoxide, KO2, is introduced to suppress indazole formation.
