- Mesoporous aromatic frameworks modified by metal chlorides in phenol alkylation with oct-1-ene
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Mesoporous polyaromatic frameworks (PAF) based on tetraphenylmethane were synthesized. The PAF/AlCl3 and PAF/FeCl3 catalysts were prepared by impregnating the synthesized products with aluminum and iron chlorides, respectively. The r
- Talanova, M. Yu.,Guojun,Karakhanov,Anisimov
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Read Online
- A Ball-Milling-Enabled Cross-Electrophile Coupling
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The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is herein described. Under a mechanochemical manifold, the reductive C-C bond formation was achieved in the absence of bulk solvent and air/moisture sensitive setups, in reaction times of 2 h. The mechanical action provided by ball milling permits the use of a range of zinc sources to turnover the nickel catalytic cycle, enabling the synthesis of 28 cross-electrophile coupled products.
- Jones, Andrew C.,Nicholson, William I.,Leitch, Jamie A.,Browne, Duncan L.
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supporting information
p. 6337 - 6341
(2021/08/23)
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- Preparation method of P-octyl phenol
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The invention relates to a preparation method of p-octyl phenol, belonging to the technical field of chemical synthesis. The preparation method comprises the following steps: carrying out a condensation reaction on p-hydroxybenzaldehyde and 2-heptanone under alkaline conditions, and carrying out catalytic hydrogenation reduction to obtain p-octyl phenol. The method disclosed by the invention has the advantages that (1) the yield and the purity of p-octyl phenol are high, no ortho-position byproduct is produced, total yield is 95% or above, the purity is as high as 99.9%, and an application range is expanded; 2) good economic performance is realized, byproducts are few, the generation of three wastes in separation and purification is reduced, the method is greener and more environment-friendly than other methods, and a used solvent and a used catalyst can be recycled. The p-octyl phenol prepared by the method can meet the use requirements of the chemical industry and the pharmaceuticalindustry.
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Paragraph 0030; 0042; 0045-0046; 0049-0050; 0053-0054; 0057
(2021/03/31)
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- Formation of C(sp3)–C(sp3) Bonds through Nickel-Catalyzed Decarboxylative Olefin Hydroalkylation Reactions
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Olefins and carboxylic acids are among the most important feedstock compounds. They are commonly found in natural products and drug molecules. We report a new reaction of nickel-catalyzed decarboxylative olefin hydroalkylation, which provides a novel practical strategy for the construction of C(sp3)?C(sp3) bonds. This reaction can tolerate a variety of synthetically relevant functional groups and shows good chemo- and regioselectivity. It enables cross-coupling of complex organic molecules containing olefin groups and carboxylic acid groups in a convergent fashion.
- Lu, Xi,Xiao, Bin,Liu, Lei,Fu, Yao
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supporting information
p. 11161 - 11164
(2016/08/03)
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- Synthesis and critical micelle concentration of a series of gemini alkylphenol polyoxyethylene nonionic surfactants
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A series of gemini n-alkylphenol polyoxyethylene surfactants (GAP) were successfully synthesized and their molecular structure were confirmed by NMR and FTIR spectrum. Using the same synthesis route, a Gemini nonylphenol polyoxyethylene surfactant (GNP) was synthesized using an industrial nonylphenol product and paraformaldehyde, and its molecular structure was also characterized by 1H-NMR and FTIR spectra. The optimal reaction conditions were established. The critical micelle concentration (CMC) values of GAP were determined by means of Wilhelmy plate method and steady-state fluorescence probe method. The experimental results show how the lengths of the hydrophilic polyoxyethylene chain and the hydrophobic tail alter the CMC values. The CMC values of the GAP are found to be much lower than those of corresponding conventional single tail nonionic surfactants of the polyethoxylated alkylphenol type, which indicates that the gemini species exhibit a better surface activity. AOCS 2011.
- Yang, Fang,Li, Gang,Xu, Nian,Liu, Rong,Zhang, Song-Mei,Wu, Zeng-Jiang
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experimental part
p. 339 - 345
(2012/06/30)
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- The reactivity of phosphonic esters in aqueous micellar solutions of cationic surfactants
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The micellar effect of cationic surfactants in alkaline hydrolysis of O-alkyl-O-aryl-chloromethyl phosphonates involves a positive contribution of concentrating the reagents and a negative effect of the micellar environment due to a loss in the activation entropy. The reactivity of substrates in micelles depends on both electronic and hydrophobic characteristics of substituents in the aryl group.
- Shagidullina,Zakharova,Valeeva,Kudryavtseva
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p. 1181 - 1185
(2007/10/03)
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- Metal cation-exchanged montmorillonite (Mn+-mont)-catalysed aromatic alkylation with aldehydes and ketones
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The alkylation of aromatic compounds with aldehydes and ketones in the presence of a variety of metal cation-exchanged montmorillonites (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+, Zn2+, H+, Na+) has been investigated. Al3+- and Zr4+-Monts are revealed to be effective as catalysts, while no reaction takes place with Na+-mont. Al3+-Mont-catalysed alkylation of phenol with several aldehydes produces mainly or almost solely the corresponding gem-bis(hydroxyphenyl)alkanes (bisphenols) in good yields, while that with several ketones affords selectively the corresponding alkylphenols in moderate to good yields. The alkylation always occurs at the carbonyl carbon without any skeletal rearrangement and the kind of products depends much on the steric hindrance of an electrophilic intermediary carbocation. The alkylation of anisole, veratrole and p-cresol proceeds well, while that of toluene, benzene, chlorobenzene and nitrobenzene scarcely occurs.
- Tateiwa, Jun-Ichi,Hayama, Ei,Nishimura, Takahiro,Uemura, Sakae
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p. 1923 - 1928
(2007/10/03)
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- Synthesis, characterization and applications of azo-containing photodestructible surfactants
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Photodestructible surfactants, sodium 4-(2-cyano-2-undecylazo)benzoate and a series of sodium 4-alkylphenylazosulfonates, have been synthesized and were shown to be surface active in solution, each exhibiting a distinct critical micelle concentration (CMC). UV irradiation of aqueous solutions of the alkylazobenzoate led to a distinct increase in surface tension, but even after complete photolysis significant surface activity remained, indicating a substantial amount of cage recombination after nitrogen evolution. UV irradiation of sodium 4-dodecylazosulfonate caused a photoscission reaction, completely destroying its surface active properties. In the case of azosulfonates with shorter alkyl chains, however, some residual surface activity remained after complete removal of the azo linkage, indicating that secondary surfactants were formed by the photolysis. The 4-alkylphenylazosulfonates were able to solubilize an oil-soluble dye in water to produce isotropic coloured solutions. Photoirradiation of these solutions led to complete loss of colour, presumably as a result of microprecipitation of the dye. The azosulfonate surfactants also readily emulsified vinyl monomers, such as styrene, in water. Attempts to achieve emulsion polymerization led to only low conversion of monomer, most likely owing to side reactions between initiating radicals and the azo linkage of the surfactant, leading in turn to disruption of the micelle.
- Dunkin, Ian R.,Gittinger, Andreas,Sherrington, David C.,Whittaker, Paul
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p. 1837 - 1842
(2007/10/03)
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- Al3+-exchanged montmorillonite as an effective solid catalyst for selective synthesis of alkylphenols and bisphenols
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Al3+-Exchanged montmorillonite-catalyzed aromatic alkylation of phenol with aldehydes produces the corresponding bisphenols mainly or almost solely in good yields, while that with ketones affords selectively the corresponding alkylphenols in mo
- Tateiwa, Jun-Ichi,Hayama, Ei,Nishimura, Takahiro,Uemura, Sakae
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- Tilt Angle Variation as a Function of Chain Length and Temperature in the Smectic C Phases of p,Alkoxyphenyl-p,Alkoxybenzoates
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The variation of the tilt angle with temperature in the smectic C phase has generally been shown to be non-existent or very slow for compounds or mixtures with the nematic-smectic C transition, while in the case of systems with the smectic A-smectic C transition, a relation between the steepness of this variation, near the transition, and the width of the smectic A domain has been observed.In this work, the variation of tilt angle in the smectic C phase is described for p-alkoxyphenyl-p-alkoxybenzoate homologous series, for which the evolution of polymorphism can be controlled systematically, by varying stepwise the length of the aliphatic chains, and for which large domains can be obtained for each type of phase sequence, nematic-, smectic A- and isotropic-smectic C.After completing the discussion made previously on the incidence of chain length on polymorphism, we confirm that the variation of tilt angle with temperature is slowest for compounds with intermediate chain lengths corresponding to the largest smectic A temperature range; this variation becomes continuously steeper when the smectic A domain becomes narrow.In addition, we show that the same description can be extended to the other types of phase sequences, by using the hypothesis of a virtual smectic A-smectic C transition above the observed nematic- or isotropic-smectic C transition.In fact, short chain lengths for homologues with a nematic/smectic C transition, or long chain lengths for homologues with an isotropic/smectic C transition, lead to an increase of the tilt angle at the phase transition and to a decrease of the amplitude of its variation with temperature; in our description, this behaviour corresponds to an increase of the temperature range between the real and virtual transitions.As a consequence, the homologues with very short and very long chain lengths show a quasi temperature-independent tilt angle, while the other homologues present a tilt angle variation similar to that observed for compounds exhibiting a smectic C/smectic A transition.This feature indicates that there is no need to distinguish between different types of smectic C phase.
- Heinrich, B.,Guillon, D.
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- Alkylation of aromatic compounds
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Monoalkylated benzene such as ethylbenzene and cumene or monoalkylated substituted benzene are produced by alkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 40:1, preferably 160:1. In a subsequent, optional process, the polyalkylated benzene or polyalkylated substituted benzene produced in the alkylation is transalkylated in the presence of an acidic mordenite zeolite catalyst.
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- Synthesis, Spectral Data and Extraction of Copper by 1-(2'-Hydroxy-5'-alkylphenyl)-1-alkanone Oximes
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1-(2'-Hydroxy-5'-alkylphenyl)-1-ethanone oximes with a normal alkyl group containing 2 to 12 carbon atoms and 1-(2'-hydroxy-5'-methylphenyl)-1-alkanone oximes containing 1 to 11 carbon atoms in the hydrocarbon chain were synthesized.Spectral data (u.v., i.r., n.m.r. and 13C) of oximes are reported.Four of these oximes were used for copper extraction from acidic solution.The results obtained indicate, that these oximes are better extractants than alkyl derivatives of 2-hydroxybenzophenone oximes.
- Krzyzanowska, Ewa,Olszanowski, A.,Juskowiak, M.
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p. 617 - 630
(2007/10/02)
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- RECHERCHES SUR LES SUBSTANCES MESOGENES-VIII; PREPARATION ET PROPERTIES MESOMORPHES DE SERIES ISOMETRIQUES
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The synthesis and the mesomorphic properties of various series of isometric mesogenic compounds are described.It is confirmed that isometric mesogenic molecules may be nematogenic and/or smectogenic according to the position of the polar rigid core.
- Malthete, Jacques,Canceill, Josette,Gabard, Jacqueline,Jacques, Jean
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p. 2815 - 2821
(2007/10/02)
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- Process for the production of 2-aryl-2H-benzotriazoles
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A process for the production of 2-aryl-2H-benzotriazoles comprises reducing and cyclizing the corresponding o-nitroazobenzenes with hydrogen at a temperature in the range of about 20° C. to about 100° C. and at a pressure in the range of about 15 psia (1 atmosphere) to about 1000 psia (66 atmospheres) in an alkaline medium at a pH over 10 in the presence of a nickel catalyst, preferably molybdenum-promoted Raney nickel. High yields of pure product are obtained directly with a concomitant reduction of undesired by-product and a reduction in effluent pollution problems.
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- Process for the production of 2-aryl-2H-benzotriazoles
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A process for the production of 2-aryl-2H-benzotriazoles comprises reducing and cyclizing the corresponding o-nitroazobenzenes with hydrogen at a temperature in the range of about 20° C. to about 100° C. and at a pressure in the range of about 15 psia (1 atmosphere) to about 1000 psia (66 atmospheres) in an organic solvent mixture containing an organic amine at a pH over 10 in the presence of noble metal hydrogenation catalyst, preferably palladium. High yields of pure product are obtained with a concomitant reduction of undesired by-products and a reduction in effluent pollution problems.
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- Process for the production of 2-aryl-2H-benzotriazoles
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A process for the production of 2-aryl-2H-benzotriazoles comprises reducing and cyclizing the corresponding o-nitroazobenzenes with carbon monoxide at a temperature in the range of about 20° C. to about 150° C. and at a pressure in the range of about 15 psia (1 atmosphere) to about 1000 psia (66 atmospheres) in an alkaline medium at a pH over 10 in the presence of a copper-amine complex catalyst. High yields of pure product are obtained with a concomitant reduction of undesired by-products and a reduction in effluent pollution problems.
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- Process for the production of 2-aryl-2H-benzotriazoles
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An improved process for the production of 2-aryl-2H-benzotriazoles by the reduction of o-nitroazobenzene intermediates with zinc in alkaline medium comprises employing a ratio of moles of alkali to moles of o-nitroazobenzene intermediate in the range of 0.2-1.7/1 in the presence of less than 150 ppm of iron based on zinc used. The improved process results in higher yields of high purity products with a concomitant reduction in the amount of undesired cleavage amine by-products and a reduction in effluent pollution problems. The process is carried out in a polar/non-polar solvent mixture.
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