26620-08-6Relevant academic research and scientific papers
HIGH-COVERAGE, LOW ODOR MALODOR COUNTERACTANT COMPOUNDS AND METHODS OF USE
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Page/Page column 32, (2016/04/20)
The present invention relates to novel compounds and their use as malodor counteractant materials.
Catalytic alkylation of alcohols to liquid ethers and organic compounds to alkylated products
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Paragraph 0030, (2013/08/15)
A catalytic process is taught for non-oxidative alkylation of organic compounds, comprising alcohols, alkanes, glycols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, thiols or phosphines, by alkyl groups produced from alcohols or glycols, forming products comprising ethers and other higher molecular weight alkylated compounds. The process is conducted at a reflux temperature below 200° C. in the presence of an acid, alkali or neutral salt dehydrating agent comprising sulfuric acid, phosphoric acid or their salts, lime or anhydrous calcium sulfate in the absence of zero valent metals and air. Specifically, this catalytic process converts ethanol to ethyl butyl ethers, ethyl hexyl ethers and dibutyl ethers or oxygenated gasoline as well as amines comprising n-butyl amine plus butanol to dibutyl amine and butyl hexyl amines at ambient pressure. This same catalytic alkylation chemistry, which does not constitute a condensation reaction, alkylates 4-hydroxybenzoic acid using ethanol to 4-ethoxyethylbenzoic acid products.
Microwave mediated protection of hindered phenols and alcohols
Pothi, Tejas,Dawange, Mahesh,Chavan, Kamlesh,Sharma, Rajiv,Deka, Nabajyoti
, p. 706 - 711 (2013/03/28)
Hindered phenols and alcohols were protected as their corresponding ethers using different alkylating agents in presence of KOH/DMSO under microwave irradiation.
Alkyl- and aryl-oxygen bond activation in solution by rhodium(I), palladium(II), and nickel(II). Transition-metal-based selectivity
Van Der Boom, Milko E.,Liou, Shyh-Yeon,Ben-David, Yehoshoa,Shimon, Linda J. W.,Milstein, David
, p. 6531 - 6541 (2007/10/03)
Reaction of [RhCl(C8H14)2]2 (C8H14 = cyclooctene) with 2 equiv of the aryl methyl ether phosphine 1 in C6D6 results in an unprecedented metal insertion into the strong sp2-sp3 aryl-O bond. This remarkable reaction proceeds even at room temperature and occurs directly, with no intermediacy of C-H activation or insertion into the adjacent weaker ArO-CH3 bond. Two new phenoxy complexes (8 and 9), which are analogous to the product of insertion into the ArO-CH3 bond (had it taken place) were prepared and shown not to be intermediates in the Ar-OCH3 bond cleavage process. Thus, aryl-O bond activation by the nucleophilic Rh(I) is kinetically preferred over activation of the alkyl-O bond. The phenoxy Rh(I)-η1-N2 complex (8) is in equilibrium with the crystallographically characterized Rh(I)-μ-N2-Rh(I) dimer(12). Reaction of [RhClC8H14)2]2 with 2 equiv of the aryl methyl ether phosphine 2, PPh3, and excess HSiR3 (R = OCH2CH3, CH2CH3) results also in selective metal insertion into the aryl-O bond and formation of (CH3O)SiR3. Thus, transfer of a OCH3 group from carbon to silicon was accomplished, showing that hydrosilation of an unstrained aryl-O single bond by a primary silane is possible. The selectivity of C-O bond activation is markedly dependent on the transition-metal complex and the alkyl group involved, allowing direction of the C-O bond activation process at either the aryl-O or alkyl-O bond. Thus, contrary to the reactivity of the rhodium complex, reaction of NiI2 or Pd(CF3CO2)2 with 1 equiv of 1 in ethanol or C6D6 at elevated temperatures results in exclusive activation of the sp3-sp3 ArO-CH3 bond, while reaction of the analogous aryl ethyl ether 4 and Pd(CF3CO2)2 results in both sp3-sp3 and sp2-sp3 C-O bond activation. The resulting phenoxy Pd(II) complex (18) is fully characterized by X-ray analysis. Heating the latter under mild dihydrogen pressure results in hydrodeoxygenation to afford an aryl-Pd(II) complex (19).
A New Rearrangement of Alkoxybenzyl Anions
Bates, Robert B.,Siahaan, Teruna J.,Suvannachut, Kessara
, p. 1328 - 1334 (2007/10/02)
Alkyl groups migrate from oxygen to carbon in alkyl aryl ethers which have been metalated in benzylic positions. 2,6-Dimethylanisole provides a variety of 2,6-dialkylphenols and their ethers in 45-80percent yields.Rearrangement products are obtained in 10-30percent yields from other dimethylanisoles and from methylanisoles.The reactions appear to proceed, like Wittig rearrangements, by homolytic cleavage of the alkyl-oxygen bond followed by recombination of the resulting radical pair in a different way.The rearrangements can be avoided by using methyl ethers and working at or below room temperature.
Studies on nucleophilic substitution reactions with cyclopentadienyliron complexes of some chloroarenes and nitorarenes and syntheses of substituted arenes by demetallation of the substitution products
Abd-El-Aziz, A.S.,Lee, C. C.,Piorko, A.,Sutherland, R. G.
, p. 95 - 108 (2007/10/02)
Nucleophilic substitution reactions with the cyclopentadienyliron (CpFe) complex of m- or p-dichlorobenzene with carbanion nucleophiles derived from ethyl acetoacetate (EAA), dibenzoylmethane (DBM) or diacetylmethane (DAM) were found to give only monosubstitution as previously observed for the CpFe complex of o-dichlorobenzene.Reaction of the CpFe complex of 2,6-dimethylchlorobenzene (XIVa) or 2,6-dimethylnitorbenzene (XIVb) with nucleophiles derived from ammonia, dimethylamine, n-butylamine, pyrrolidine, ethanol, phenol, o-thiocresol and EAA all gave SNAr products, without significant steric hindrance.However, no reaction was observed in the treatment of XIVa or XIVb with DBM, suggesting that only with a bulky nucleophile such as that derived from DBM were steric hindrance effects sufficiently large to prevent an SNAr reaction with XIVa or XIVb.Pyrolytic sublimation of the various SNAr products was found to cause decomposition in some cases, but in most instances, demetallation took place giving rise to substituted arenes.New substituted arenes prepared in this way in the present work included RC6H4CH(COC6H5)2, with R = p-CH3, o-Cl, m-Cl or p-Cl, and 2,6-(CH3)2C6H3Y, with Y = CH3(CH2)3NH, C2H5O or o-CH3C6H4S.
