127-41-3Relevant articles and documents
Macroreticular p-(ω-sulfonic-perfluoroalkylated) polystyrene ion-exchange resins: A new type of selective solid acid catalyst
Lin, Zhenghuan,Zhao, Chengxue
, p. 3556 - 3558 (2005)
Macroreticular p-(ω-sulfonic-perfluoroalkylated) polystyrene (FPS) cation-exchange resins 3 have been synthesized by sequential p-perfluoroalkylation of macroreticular polystyrene (PS) 1 with ω-fluorosulfonylperfluorodiacyl peroxide 2, hydrolysis and acidification; the fluorinated mesoporous resins exhibited higher activity and selectivity than commercial Amberlyst 36 and Nafion NR50 in the cyclization of pseudoionone. The Royal Society of Chemistry 2005.
Cyclization of pseudoionone into α-Ionone over heteropolyacid supported on mesoporous silica SBA-15
Rachwalik,Michorczyk,Ogonowski
, p. 1384 - 1390 (2011)
Cyclization of pseudoionone into α-ionone was performed over the series heteropolyacid supported on SBA-15 in liquid-phase at 363 and 373 K using a batch reactor. It has been demonstrated that the liquid-phase synthesis of α-ionone by pseudoionone cyclization can be efficiently achieved on heteropolyacid/SBA-15 materials. The high catalytic performance of PW 12/SBA-15 materials is due to their strong Bronsted acidity, high dispersion of active phase and also to absence of steric constraints for pseudoionone cyclization. PW12/SBA-15 catalysts are specially active and selective for this reaction giving predominantly α-ionone, as the main product, with high yield (about 60% at 373 K after 2 h) close to that obtained via the homogeneous synthesis. This catalytic system is more active and efficient in comparison with heteropolyacid supported on commercial silica. In order to achieve comparable amount of α-ionone, as is got for PW 12/SBA-15, belongs to apply five times more of the catalyst based on classical SiO2.
ω-Sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybridized nanocomposite as a new kind of solid acid catalyst
Lin, Zhenghuan,Huang, Limei,Ling, Qidan,Chen, Hong,Zhao, Chengxue
, p. 73 - 79 (2012)
A new kind of ω-sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybrid nanocomposite FSMA/SiO2 has been synthesized under mild conditions by perfluoroalkylation of styrene-maleic anhydride copolymer (SMA) with ω-fluorosulfonylperfluorodiacyl peroxides (SFAP), and followed in turn by aminolysis using (3-aminopropyl)triethoxysilane (APTES), alkali hydrolysis, gelation with tetraethoxysilane (TEOS) and finally acidification. The hybrid solid acid FSMA/SiO2 with terminal perfluoroalkylsulfonic and carboxyl groups was characterized by FTIR, SEM, TEM, TGA, XPS, EDX, acidimetry and nitrogen sorption technique. Its pore structure, acid strength and acid amount were easily modulated by controlling the gelation and perfluoroalkylation conditions. The catalytic activity and selectivity, as well as reusability of FSMA/SiO2 were tested in three important reactions, namely, cyclization of pseudoionone, condensation of indole and esterification of benzoic acid. Owing to the higher exchange capacity than that of Nafion/SiO2, and the stronger acidity than that of Amberlyst-15, the nanocomposite FSMA/SiO2 showed higher activity and selectivity than these commercial solid acids in the reactions.
Synthesis of ionones on solid Br?nsted acid catalysts: Effect of acid site strength on ionone isomer selectivity
Díez,Apesteguía,Di Cosimo
, p. 267 - 274 (2010)
The effect of Br?nsted acid site strength on the liquid-phase conversion of pseudoionone to ionone isomers (α-, β- and γ-ionone) was studied on resin Amberlyst 35W, silica-supported heteropolyacid (HPAS) and silica-supported triflic acid (TFAS). Catalyst acidity was probed by temperature-programmed desorption of NH3 coupled with infrared spectra of adsorbed pyridine. The initial pseudoionone conversion rate followed the order: TFAS > Amberlyst 35W ≈ HPAS. Synthesis of the three ionone isomers occurred via a common cyclic carbocation intermediate formed from the activation of the pseudoionone molecule on Br?nsted acid sites. Initial ionone mixtures containing a α:β:γ isomer distribution of about 40:20:40 were formed, irrespective of the acid site strength. But the ionone mixture composition changed with the progress of the reaction because γ-ionone was consecutively converted to α-ionone on HPAS and Amberlyst 35W, whereas the stronger acid sites of TFAS converted γ-ionone to β-ionone.
Continuous preparation method of high-selectivity alpha-ionone
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Paragraph 0033-0071, (2020/08/06)
The invention provides a continuous preparation method of high-selectivity alpha-ionone, pseudoionone is taken as a raw material, alpha-ionone is prepared under the condition of a catalyst system, thecatalyst system comprises a catalyst 1, a catalyst 2 and an auxiliary agent, the catalyst 1 is concentrated sulfuric acid or methanesulfonic acid, and the catalyst 2 is liquid organic carboxylic acid. Pseudoionone, a solvent and a catalyst system are uniformly mixed in a static mixer, then enter a pipeline reactor and react in the pipeline reactor, then the reaction liquid is discharged from an outlet of the pipeline reactor and enters a quenching stirring kettle to be quenched, and the reaction is ended. The synthesis process provided by the invention has the advantages of high catalytic efficiency, short reaction time, high alpha ionone content, continuous application of the catalyst and less three wastes, realizes continuous reaction, greatly saves the reaction time, operation and device cost, meets the requirements of green chemistry, and is suitable for industrial large-scale production.
Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release
Griesbeck, Axel G.,Porschen, Bj?rn,Kropf, Christian,Landes, Agnieszka,Hinze, Olga,Huchel, Ursula,Gerke, Thomas
, p. 539 - 553 (2017/01/25)
Five families of caged fragrance compounds that allow the storage and release of the following small volatile organic molecules are described: terpene hydrocarbons, aldehydes, ketones, Michael-type α,β-unsaturated enones, and carboxylic acids and esters. These caged molecules are released by photoexcitation via carbonyl-directed hydrogen-transfer processes and subsequent C-C bond cleavage (Norrish Type II) or by didenitrogenation of diazirines.
Controlled release of encapsulated bioactive volatiles by rupture of the capsule wall through the light-induced generation of a gas
Paret, Nicolas,Trachsel, Alain,Berthier, Damien L.,Herrmann, Andreas
supporting information, p. 2275 - 2279 (2015/02/19)
The encapsulation of photolabile 2-oxoacetates in core-shell microcapsules allows the light-induced, controlled release of bioactive compounds. On irradiation with UVA light these compounds degrade to generate an overpressure of gas inside the capsules, which expands or breaks the capsule wall. Headspace measurements confirmed the light-induced formation of CO and CO2 and the successful release of the bioactive compound, while optical microscopy demonstrated the formation of gas bubbles, the cleavage of the capsule wall, and the leakage of the oil phase out of the capsule. The efficiency of the delivery system depends on the structure of the 2-oxoacetate, the quantity used with respect to the thickness of the capsule wall, and the intensity of the irradiating UVA light.
PRO-FRAGRANCE COMPOUNDS
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Page/Page column 22, (2014/12/09)
A compound of Formula (I) wherein R1 represents a C3 to C20 hydrocarbon group derived from a fragrant alcohol of formula R1OH or from a fragrant aryl aldehyde or ketone of Formula (II), wherein: R2 is, independently, hydrogen atom, hydroxyl group, acetoxy group, -O(C=O)CH(CH3), optionally substituted C1-C6 alkyl group or C1-C6 alkoxy group, wherein any two of R2 may form an optionally substituted 5 or 6 membered ring, and R1 represents a radical derived from a fragrant alcohol of formula R1OH or from a fragrant aldehyde or from a fragrant aryl aldehyde or ketone of formula (II). The compounds are useful for example as a precursor for the prolonged delivery or release of fragrant compounds such as fragrant alcohols or aldehydes.
Aromatic aldols and 1,5-diketones as optimized fragrance photocages
Griesbeck, Axel G.,Hinze, Olga,Goerner, Helmut,Huchel, Ursula,Kropf, Christian,Sundermeier, Uta,Gerke, Thomas
experimental part, p. 587 - 592 (2012/06/30)
Aromatic aldols and 1,5-diketones with abstractable γ-hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3a-d are easily accessible by Mukaiyama addition and are cleaved to form the substrates with high quantum yields under solar radiation. By tuning the properties of the chromophores, a series of δ-damascone cages 5 were developed that can be used for selective and fast (5a,e) or slow (5b,d) release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.
Gold-mediated synthesis of α-ionone
Merlini, Valentina,Gaillard, Sylvain,Porta, Alessio,Zanoni, Giuseppe,Vidari, Giovanni,Nolan, Steven P.
scheme or table, p. 1124 - 1127 (2011/03/22)
A simple and convenient synthesis of α-ionone, an important component of flowers and fragrances, is reported. The key step in the formation of the α,β-unsaturated ketone moiety involves an NHC-AuI catalyzed Meyer-Schuster-like rearrangement of readily prepared propargylic esters. The complex [{Au(IPr)}2(μ-OH)][BF4] proved to be the most efficient catalyst leading to α-ionone in 70% yield from a propargylic benzoate. This optimized procedure represents a valuable and attractive alternative to classical methods leading to α,β- unsaturated ketones, such as the Wittig or aldol reactions.
