- Preparation method of organic carboxylic acid
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The invention discloses a preparation method of organic carboxylic acid. The preparation method comprises the following steps that catalysts, olefins, water and solvents are added into a reaction container; CO is introduced; heating reaction is performed; after the reaction completion, separation is performed to obtain organic carboxylic acid; the catalysts comprise transition metal catalysts, ligands and catalysis assistants; the catalysis assistants comprise Lewis acid salt. The preparation method has the advantages that the dependency on protonic acid in the prior art is avoided; the Lewisacid salt is used as the catalysis assistant, so that the corrosion of a reaction system on equipment can be effectively prevented; the requirements on equipment are lowered. The preparation method has excellent substrate practicability; the operation steps are simple and fast; the reaction conditions are mild and are easy to control; the raw materials are cheap and can be easily obtained; the product yield and the product purity are high; the preparation method is suitable for large-scale industrial production; the normal/iso ratio of reaction products can be regulated and controlled throughthe catalysis assistants; the defects of regulating and controlling the normal/iso ratio of the reaction products by traditional phosphine ligands are overcome; the reaction progress of the reaction is simplified; the cost is favorably reduced.
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Paragraph 0059-0061; 0086-0089
(2019/10/15)
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- Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations
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Impactful regioselectivity control is crucial for cost-effective chemical synthesis. By using cheap and abundant iron(iii) salts, the hydroxycarbonylations of both aromatic and aliphatic alkenes were significantly enhanced in both reactivity and selectivity (iso/n or n/iso up to >99:1). Moreover, Pd-catalyzed carbonylation selectivity can be switched from branched to linear by using different Fe(iii) salts. In addition, similar results were obtained for the carbonylation of secondary alcohols.
- Huang, Zijun,Cheng, Yazhe,Chen, Xipeng,Wang, Hui-Fang,Du, Chen-Xia,Li, Yuehui
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supporting information
p. 3967 - 3970
(2018/04/23)
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- Anchored Pd-complexes in mesoporous supports: Synthesis, characterization and catalysis studies for carbonylation reactions
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Pd(pyca)(PPh3)(OTs) [pyca = 2-picolinate] complex is efficiently anchored inside different mesoporous matrices, such as MCM-41, MCM-48, SBA-15 using a molecular aminopropyl tether moiety employing different synthesis strategies. Thorough characterization of the materials using powder XRD, multinuclear (13C, 29Si, 31P) CP-MAS NMR, XPS, SEM, N2-sorption studies etc. confirmed the successful anchoring of the palladium complex to the walls of the support matrices thus establishing the synthesis protocols unambiguously. The catalysts were found to be highly active and selective for the carbonylation of different aryl olefins and alcohols. Consecutive recycling and successful reuse proved the stability and true heterogeneous nature of all the anchored catalysts, which is a substantial advancement over the existing heterogeneous catalysts for carbonylation.
- Sarkar, Bibhas R.,Chaudhari, Raghunath V.
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p. 154 - 173
(2013/01/15)
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- Synthesis of 1,4:3,6-dianhydro-d-mannitol 2,5-(hydrogenphosphate) and its usage in palladium-catalyzed hydroxycarbonylation of styrene
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Phosphorylation of 1,4:3,6-dianhydro-d-mannitol by phosphorus oxychloride in the presence of triethylamine followed by hydrolysis gave a cyclie hydrogen phosphate, which has the crystal structure of 6-hydroxy-6-oxo-2,5,7,10-tetraoxa-6-phospha-tricyclo[6.3.0.04,11]undecane. It was used as a chiral ligand in palladium-catalyzed hydroxycarbonylation of styrene. The regioselectivity was good, but the optical yield was limited.
- Jiang, Biao,Huang, Zuo-Gang,Cheng, Ke-Jun
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p. 2797 - 2803
(2007/10/03)
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- Anchored Pd complex in MCM-41 and MCM-48: Novel heterogeneous catalysts for hydrocarboxylation of aryl olefins and alcohols
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We report here, for the first time, synthesis of anchored Pd complexes in mesoporous supports such as MCM-41 and MCM-48 as true heterogeneous catalysts for hydrocarboxylation of aryl olefins and alcohols to give excellent conversion (~100%) and regioselectivity (~99%) for 2-arylpropionic acids. The catalysts were characterized by powder-XRD, 31PCP-MAS NMR, FT-IR, TEM, XPS and ICP-AES. Recycle studies with these anchored Pd mesoporous catalysts were performed to confirm true heterogeneity. Copyright
- Mukhopadhyay, Kausik,Sarkar, Bibhas R.,Chaudhari, Raghunath V.
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p. 9692 - 9693
(2007/10/03)
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- Highly active water-soluble palladium catalyst for the regioselective carbonylation of vinyl aromatics to 2-arylpropionic acids
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A novel water-soluble Pd complex containing pyridine carboxylate and TPPTS as ligands is a highly active catalyst for the carbonylation of vinyl aromatics under biphasic conditions and provides high regioselectivity to 2- arylpropionic acids.
- Jayasree,Seayad,Chaudhari
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p. 1239 - 1240
(2007/10/03)
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- Highly active supported palladium catalyst for the regioselective synthesis of 2-arylpropionic acids by carbonylation
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A catalyst system consisting of supported palladium in the presence of phosphine ligands, TsOH and LiCl catalyses the carbonylation of 1-arylethanols to 2-arylpropionic acids with significantly improved activity and regioselectivity; the catalyst can be recycled with no loss in activity and selectivity.
- Jayasree,Seayad,Chaudhari
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p. 1067 - 1068
(2007/10/03)
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- DIRECT, REGIOSELECTIVE HYDROCARBOXYLATION OF ALKYNES TO SATURATED ACIDS BY COBALT AND NICKEL CATALYSTS UNDER PHASE TRANSFER CONDITIONS
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Phase transfer catalyzed carbonylation of alkynes in the presence of cobalt chloride, potassium cyanide, and nickel cyanide affords saturated carboxylic acids, with good selectivity observed for the branched-chain isomer.
- Lee, Jong-Tae,Alper, Howard
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p. 1769 - 1770
(2007/10/02)
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- Polyprenyl compounds
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A polyprenyl compound terminated with a group of STR1 is novel and useful as an antihypercholesterolemic agent and an antiarteriosclerotic agent, in which X is a group of the formula STR2 (wherein K and L are independently a hydrogen atom or form a single valence bond between the carbon atoms to which they are attached), a group represented by the formula --CH2 -- or a group represented by the formula --(CH2)2 --, m is an integer of 0 or 1, and R stands for a hydroxy group, a group represented by the formula STR3 wherein R1 and R2 may be the same or different and each stands for a hydrogen atom or a lower alkyl group and p stands for an integer of 1 or 2, a group represented by the formula --NH--(CH2)q --OH (wherein q denotes an integer of 1 or 2) or a group represented by the formula
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- In Vivo Characterization of Hydroxamic Acid Inhibitors of 5-Lipoxygenase
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The hydroxamic acid functionality can be incorporated into simple molecules to produce potent inhibitors of 5-lipoxygenase.The ability of many of these hydroxamates to inhibit leukotriene synthesis in vivo has been measured directly with a rat peritoneal anaphylaxis model.Despite their potent enzyme inhibitory activity in vitro, many orally dosed hydroxamic acids only weakly inhibited leukotriene synthesis in vivo.This discrepancy is attributable at least in part to the rapid metabolism of hydroxamates to the corresponding carboxylic acids, which are inactive against the enzyme.A study of the structural features that affect this metabolism revealed that 2-arylpropionohydroxamic acids are relatively resistant to metabolic hydrolysis.Several members of this class of hydroxamates are described that are orally active inhibitors of leukotriene synthesis.
- Summers, James B.,Gunn, Bruce P.,Mazdiyasni, Hormoz,Goetze, Andrew M.,Young, Patrick R.,et al.
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p. 2121 - 2126
(2007/10/02)
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- THE SYNTHESIS OF ARYLPROPIONIC ACIDS AND THE QUANTITATIVE RELATIONSHIP BETWEEN THE STRUCTURE AND THE ACTIVATION OF FIBRINOLYSIS
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A number of substituted 2-arylpropionic (IV) and 3-arylpropionic (V) acids were prepared and their activity in the activation of fibrinolysis and the inhibition of heat denaturation of serum albumin was evaluated.The results were worked up using the method of regression analysis.From the regression equation obtained it may be considered that both activities are affected mainly by the lipophilicity of the aromatic substituents.The effect of branching in the connecting chain between the carboxyl group and the aromatic ring is negligible in both activities.Thelinear dependence of the fibrinolytic capacity on lipophilicity is in both series of acids, IV and V, characterized by a distinct decrease in activity, following the attainment of the optimum value of lipophilicity.In the series of cinnamic acids (VI) regression equations concerning the inhibition of the denaturation of serum albumin and the activation of fibrinolysis were also calculated, showing a linear dependence of these activities on the lipophilicity of the varying substituents R and X.Summary regression equations were derived for both activities in the whole set of acids I-VI.Both the inhibition of the denaturation of serum albumin , and the activation of fibrinolysis depends on the lipophilicity of the mentioned acids exclusively.The modification of the connecting chain between the carboxyl group and the aromatic ring affects both activities primarily by the corresponding change in lipophilicity.
- Kuchar, Miroslav,Brunova, Bohumila,Rejholec, Vaclav,Roubal, Zdenek,Nemecek, Oldrich
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p. 1173 - 1187
(2007/10/02)
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- Preparation of carboxylic acids from glycidonitriles with ionic lewis acids
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Process for preparing carboxylic acids by converting a glycidonitrile to a 2-oxopropionitrile via use of an ionic Lewis acid, and conversion of the 2-oxopropionitrile to the carboxylate salt with a base and of the salt to the carboxylic acid with acid. The process is especially useful for the preparation of 2-(p-isobutylphenyl)propionic acid, (lbuprofen), also known as Motrin, a known and highly active antiinflammatory agent as well as a host of other carboxylic acids which are known in the art as useful compounds.
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