3548-78-5Relevant academic research and scientific papers
Preparation method of pseudoionone
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Paragraph 0027-0056, (2021/03/13)
The invention provides a preparation method of a vitamin A intermediate pseudoionone. The method relates to a reaction for preparing pseudoionone by catalyzing condensation of acetone and citral by using a novel catalyst, the use amount of reaction acetone can be effectively reduced by using the novel catalyst, self-polymerization and copolymerization of citral and pseudoionone in the reaction arereduced, and the reaction selectivity and yield are improved.
Continuous synthesis method of pseudoionone
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Paragraph 0035-0084, (2021/04/10)
The invention belongs to the field of pseudoionone preparation, and relates to a continuous synthesis method of pseudoionone, which comprises the following steps: continuously introducing citral, acetone and an alkaline catalyst containing inorganic alkali and acetate into a tubular reactor to carry out Aldol condensation reaction, and gradually raising the reaction temperature of the tubular reactor, and continuously introducing the condensation reaction product into a multi-kettle series acetone recovery device to recover acetone, carrying out extraction layering on the acetone removal product, and neutralizing the obtained oil layer with dilute acid to obtain the pseudoionone. On the premise of economy and environmental protection, high yield and high purity of pseudoionone and high conversion rate of citral serving as a raw material are realized, acetone and an alkaline water layer are recycled, and the production cost is reduced.
PROCESS OF MAKING PSEUDOIONONE AND HYDROXY PSEUDOIONONE IN AQUEOUS MIXTURES COMPRISING CITRAL AND ACETONE, COMPRISING ADDING FIRST AND SECOND AMOUNTS OF HYDROXIDE
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Page/Page column 30-33, (2020/06/05)
Described is a process of making pseudoionone and hydroxy pseudoionone comprising the steps of (i) preparing a first aqueous mixture comprising first concentrations of acetone, citral and hydroxide, (ii) producing a second aqueous mixture by allowing to react for a reaction time the components of the first aqueous mixture and (iii) producing a third aqueous mixture by adding to the second aqueous mixture a second amount of hydroxide so that an additional amount of pseudoionone is formed in the third aqueous mixture. The invention further suggests an apparatus for making pseudoionone and hydroxy pseudoionone as well as to a respective process and use of said apparatus in making pseudoionone and hydroxy pseudoionone.
APPARATUS FOR AND PROCESS OF MAKING PSEUDOIONONE AND HYDROXY PSEUDOIONONE
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Page/Page column 29-31, (2020/06/05)
The invention relates to an apparatus (1) for producing pseudoionone and hydroxy pseudoionone. It suggests an apparatus (1) comprising first and second substantially vertically oriented reactor chambers oriented such that components flow through the first and second reactor chambers in different directions, wherein the first reactor chamber (13) is configured to receive a first component feed (C1) containing a first aqueous mixture through an inlet (15), and to produce a second aqueous mixture, and wherein the apparatus (1) comprises a mixing device (17) positioned downstream of the first component feed inlet (15)and configured to add a second component feed (C2) to the first component feed (C1) when the second aqueous mixture has formed, and the second reactor chamber (23) is configured to receive the first and second component feeds unified in the mixing device (17) from the first reactor chamber (13) and to produce a third aqueous mixture from the first and second aqueous mixtures. The invention further suggests a method and a use for producing pseudoionone and hydroxy pseudoionone.
Method for catalytically synthesizing pseudoionone by using alkaline immobilized ionic liquid
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Paragraph 0023-0033, (2020/06/09)
The invention discloses a method for catalytically synthesizing pseudoionone by using alkaline immobilized ionic liquid. In the method, citral is adopted as a raw material, acetone is slowly dropwiseadded at 40-50 DEG C under the condition that the alkaline immobilized ionic liquid is used as a catalyst to react, thereby obtaining the pseudoionone; a carrier used in the alkaline immobilized ionicliquid is a PS material, the PS material is polystyrene, and the alkaline immobilized ionic liquid is one of the following components shown in the specification. The alkaline immobilized ionic liquidcatalyst disclosed by the invention is easy to separate from a reaction solution, avoids the condition of catalyst loss caused by multiple cyclic reactions, and has the advantages of high product yield, clean product and the like in the process of synthesizing pseudoionone.
Water-promoted surface basicity in FeO(OH) for the synthesis of pseudoionones (PS) and their analogues
Vernekar, Dnyanesh,Sakate, Sachin S.,Rode, Chandrashekhar V.,Jagadeesan, Dinesh
, p. 80 - 89 (2019/09/10)
Use of Iron oxyhydroxide (γ-FeO(OH)) as a robust catalyst for the synthesis of important intermediates like pseudoionones and their analogues through the C-C bond formation reactions like knoevenagel and aldol condensation is explored. These motifs are the building blocks for the construction of the sesquiterpenes as well as the diterpenes such as retinoic acid, Vitamin A etc. Iron oxyhydroxide (γ-FeO(OH)) was synthesized and well characterized using XRD, FT-IR, TEM, XPS and adsorption studies to establish the catalytic activity. A thorough investigation on the nature of basic sites and the role of water as a promoter was explored based on dye adsorption, in situ methanol dissociation and CO2 adsorption studies. The catalyst also showed a wide range of substrate scope with active methylene groups involving various functional groups such as cyanides, esters and acetophenones along with its stability and reproducibility.
Method for synthesizing alpha,gamma-unsaturated dienone from propargyl alcohol and catalyst system used for method
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Paragraph 0055-0057; 0059-0060, (2019/04/10)
The invention discloses a method for synthesizing alpha,gamma-unsaturated dienone from propargyl alcohol and a catalyst system used for the method. The method comprises the following steps: (1) a Saucy-Marbet reaction is carried out on propargyl alcohol and alkoxy propylene under the action of an acidic resin catalyst to obtain an allenyl ketone intermediate; and (2) a heterogeneous reaction is carried out on the allenyl ketone under the action of a solid base catalyst to obtain the alpha,gamma-unsaturated dienone product. The method disclosed by the invention has the main advantages that solid catalysts are adopted in the two steps of reactions, the catalyst activity is high, and the catalysts are easy to separate from products. Compared with a separation process in an existing homogeneous acid catalysis process, the separation process in the method provided by the invention is greatly simplified. Secondly, the acid resin catalyst and solid base catalyst adopted in the method both canbe continuously recycled, so that the cost is low, and the method is economical and feasible and is superior to the existing known process.
A pseudo-Ionone synthesis method (by machine translation)
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Paragraph 0038, (2018/10/27)
The invention relates to a pseudo-Ionone synthetic method, include a dehydrogenation-Linalool with 2 - methoxy propylene in a microchannel reactor Saucy - Marbet sequentially and isomerization reaction preparation of pseudo-Ionone. In a microchannel reactor dehydrolinalool through Saucy - Marbet reaction and the isomerization reaction to make the pseudo-Ionone, realizes the continuous production of pseudo-Ionone, and high efficiency, less reaction steps, high yield, high selectivity, and less pollution, accord with the green chemical development concept. (by machine translation)
Synthesis of apo-13- and apo-15-lycopenoids, cleavage products of lycopene that are retinoic acid antagonists
Narayanasamy, Sureshbabu,Sun, Jian,Pavlovicz, Ryan E.,Eroglu, Abdulkerim,Rush, Cassandra E.,Sunkel, Benjamin D.,Li, Chenglong,Harrison, Earl H.,Curley, Robert W.
, p. 1021 - 1029 (2017/05/17)
Consumption of the tomato carotenoid, lycopene, has been associated with favorable health benefits. Some of lycopene's biological activity may be due to metabolites resulting from cleavage of the lycopene molecule. Because of their structural similarity to the retinoic acid receptor (RAR) antagonist, β-apo-13-carotenone, the "first half" putative oxidative cleavage products of the symmetrical lycopene have been synthesized. All transformations proceed in moderate to good yield and some with high stereochemical integrity allowing ready access to these otherwise difficult to obtain terpenoids. In particular, the methods described allow ready access to the trans isomers of citral (geranial) and pseudoionone, important flavor and fragrance compounds that are not readily available isomerically pure and are building blocks for many of the longer apolycopenoids. In addition, all of the apo-11, apo-13, and apo-15 lycopenals/lycopenones/lycopenoic acids have been prepared. These compounds have been evaluated for their effect on RAR-induced genes in cultured hepatoma cells and, much like β-apo-13-carotenone, the comparable apo-13-lycopenone and the apo-15-lycopenal behave as RAR antagonists. Furthermore, molecular modeling studies demonstrate that the apo-13-lycopenone efficiently docked into the ligand binding site of RARα. Finally, isothermal titration calorimetry studies reveal that apo-13-lycopenone acts as an antagonist of RAR by inhibiting coactivator recruitment to the receptor.
Methylionone and preparation method of methylionone intermediate
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Paragraph 0030; 0031; 0032; 0033; 0034-0037; 0045-0046, (2017/08/29)
The invention discloses methylionone and a preparation method of a methylionone intermediate. According to an existing preparation method of methylionone, a lot of alkali usually needs to be wasted, and on the other hand, a lot of three wastes are caused. Under the conditions that citral and butanone serve as raw materials, PEG serves as a solvent and metal hydroxide serves as a condensation agent, an Aldol condensation reaction is conducted, and false methylionone is synthesized; the obtained false methylionone is subjected to a cyclization reaction catalyzed by acid, and methylionone is synthesized. According to methylionone and the preparation method of the methylionone intermediate, an adopted PEG-M(OH)x catalysis system improves the synthesis efficiency of the false methylionone, and the ratio of the false methylionone is kept at 68-79%; moreover, an adopted phosphoric acid-normal hexane catalytic cyclization system greatly improves the cyclization yield; an adopted catalytic condensation system can be used indiscriminately for several times, so that the cost is reduced, and environmental pollution is also reduced.
