cas 36366-93-5, 2-[2-[2-(2-phenoxyethoxy)ethoxy]ethoxy]ethanol

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PROCESS FOR THE CONTINUOUS PRODUCTION OF HIGH PURITY PHENOLIC GLYCOL ETHER
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.
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Page/Page column 13-15

(2009/07/17)

The Development of a New Nitrating Agent: The Unusual Regioselective Nitration of Diphenylpolyethylene Glycols and Phenylpolyethylene Glycols with Trimethylsilyl Nitrate - BF3OEt2
We have investigated the nitration of the following podands, 1-phenoxy-8-(2'-nitrophenoxy)-, 1-phenoxy-8-(4'-nitrophenoxy)-, and 1-(2',4'-dinitrophenoxy)-8-phenoxy-3,6-dioxaoctane (2, 3, and 4), and 1-(2',4'-dinitrophenoxy)-11-phenoxy-3,6,9-trioxaundecane (5), 1-phenoxy-3,6,9-trioxadecane (6), and 1-phenoxy-3,6,9,12-tetraoxatridecane (7), with trimethylsilyl nitrate catalyzed by BF3OEt2, which is soluble in nonpolar solvents.The reaction selectivity was measured by the ortho:para ratio of the nitrated products and was unusually large in CCl4.The structures of all isolated products, 1,8-bis(2'-nitrophenoxy)-, 1-(2'-nitrophenoxy)-8-(4'-nitrophenoxy)-, 1,8-bis(4'-nitrophenoxy)-, 1-(2',4'-dinitrophenoxy)-8-(2'-nitrophenoxy)-, and 1-(2',4'-dinitrophenoxy)-8-(4'-nitrophenoxy)-3,6-dioxaoctane (8, 9, 10, 11, and 12), 1-(2',4'-dinitrophenoxy)-11-(2'-nitrophenoxy)- and 1-(2',4'-dinitrophenoxy)-11-(4'-nitrophenoxy)-3,6,9-trioxaundecane (13 and 14), 1-(2'-nitrophenoxy)- and 1-(4'-nitrophenoxy)-3,6,9-trioxadecane (15 and 16), and 1-(2'-nitrophenoxy)- and 1-(4'-nitrophenoxy)-3,6,9,12-tetraoxatridecane (17 and 18), were confirmed by the independent preparation of these compounds using a modification of Joeger's method.We have invented a new nitrating system (trimethylsilyl nitrate and BF3OEt2) and have shown that the selectivity (o/p ratio of nitrated products) is unusually high in CCl4.
Kimura, Masaru,Kajita, Kazushige,Onoda, Naoyuki,Morosawa, Shiro
p. 4887 - 4892
(2007/10/02)

SELECTIV BROMINATION OF THE AROMATIC RING IN ω-PHENYLPOLYOXAALKANES AND ALKANOLS IN MICELLES
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.
Jursic, Branko
p. 1553 - 1558
(2007/10/02)

Chromoionophores, VII. Podands Carrying Terminal Electron-Donor- and -Acceptor Groups. Cation-Influenced Charge Transfer Absorption
The synthesis and spectroscopic investigation of the new noncyclic neutral ligands 12-20 of the glycol ether type (podands) carrying terminal electron-donor- and -acceptor groups are described.The podands show intramolecular charge transfer interactions which can be influenced selectively by complexed cations.The ligands 13 and 20 cause significant increases of extinction and bathochromic shifts of the charge transfer bands in the UV/Vis spectra on addition of alkali perchlorates, whereas the shorter ligands 14 and 18 show a decrease of extinction and hypsochromic shifts under similar conditions.Some of the noncyclic chromoionophores discern considerably and visually perceivably between Na+ and K+ or Li+ and Na+, respectively, in acetonitrile.The cation selective alterations in the electron spectra are discussed in view of steric effects considering some complex stability constants determined by photometric titrations.
Loehr, Hans-Gerd,Voegtle, Fritz
p. 914 - 921
(2007/10/02)

Phase-Transfer-Catalyzed Gomberg-Bachmann Synthesis of Unsymmetrical Biarenes: A Survey of Catalysts and Substrates
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.
Beadle, James R.,Korzeniowsky, Stephen H.,Rosenberg, David E.,Garcia-Slanga, Blanche J.,Gokel, George W.
p. 1594 - 1603
(2007/10/02)