7204-16-2Relevant articles and documents
Base- A nd Catalyst-Induced Orthogonal Site Selectivities in Acylation of Amphiphilic Diols
Ashush, Natali,Dobrovetsky, Roman,Fallek, Amit,Fallek, Reut,Portnoy, Moshe
supporting information, (2020/05/25)
Seeking to selectively functionalize natural and synthetic amphiphiles, we explored acylation of model amphiphilic diols. The use of a nucleophilic catalyst enabled a remarkable shift of the site selectivity from the polar site, preferred in background noncatalyzed or base-promoted reactions, to the apolar site. This tendency was significantly enhanced for organocatalysts comprising an imidazole active site surrounded by long/branched tails. An explanation of these orthogonal modes of selectivity is supported by competitive experiments with monoalcohol substrates.
Tough, Long-Term, Water-Resistant, and Underwater Adhesion of Low-Molecular-Weight Supramolecular Adhesives
Deng, Yan,Dong, Shengyi,Lai, Jinlei,Li, Xing,Zhao, Gai
supporting information, p. 5371 - 5379 (2020/04/09)
Modern functional adhesives have attracted considerable attention due to their reversible adhesion capacities and stimuli-responsive adhesion behavior. However, for modern functional adhesives, polymeric structures were highly necessary to realize adhesion behaviors. Supramolecular adhesives from low-molecular-weight monomers were rarely recognized. Compared with polymeric adhesive materials, it remains challenging for supramolecualr adhesive materials to realize tough adhesion on wet surfaces or even under water. In this study, a new supramolecular adhesive consisting of low-molecular-weight monomers was successfully designed and prepared. Strong and long-term adhesion performance was realized on various surfaces, with a maximum adhesion strength of 4.174 MPa. This supramolecular adhesive exhibits tough and stable adhesion properties in high-moisture and underwater environments (including seawater). Long-term underwater adhesion tests display the potential application of low-molecular-weight adhesive as a marine adhesive.
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.
Formation of huge cyclic oligomers in the condensation polymerization of bis(9-hydroxy-1,4,7-trioxanonyl) substituted naphthalene and benzenes with both aromatic and aliphatic bis-acid chlorides
Mertens, Ingrid J. A.,Wegh, Rene,Jenneskens, Leonardus W.,Vlietstra, Edward J.,Van Der Kerk-van Hoof, Anca,Zwikker, Jan W.,Cleij, Thomas J.,Smeets, Wilberth J. J.,Veldman, Nora,Spek, Anthony L.
, p. 725 - 736 (2007/10/03)
Without the use of high dilution techniques condensation polymerization of bis(9-hydroxy-1,4,7-trioxanonyl) substituted naphthalene and benzenes (1a-d) with the bis-acid chlorides terephthaloyl dichloride (2), adipoyl dichloride (5a) and isophthaloyl dich
The Development of a New Nitrating Agent: The Unusual Regioselective Nitration of Diphenylpolyethylene Glycols and Phenylpolyethylene Glycols with Trimethylsilyl Nitrate - BF3OEt2
Kimura, Masaru,Kajita, Kazushige,Onoda, Naoyuki,Morosawa, Shiro
, p. 4887 - 4892 (2007/10/02)
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.
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.
