111-16-0Relevant articles and documents
Colloidal tectonics for tandem synergistic Pickering interfacial catalysis: Oxidative cleavage of cyclohexene oxide into adipic acid
Yang, Bingyu,Leclercq, Lo?c,Schmitt, Véronique,Pera-Titus, Marc,Nardello-Rataj, Véronique
, p. 501 - 507 (2019)
Supramolecular preorganization and interfacial recognition can provide useful architectures for colloidal building. To this aim, a novel approach, based on colloidal tectonics involving two surface-active particles containing both recognition and catalytic sites, has been developed for controlling the formation and the properties of Pickering emulsions. This was illustrated by the combination of dodecyltrimethylammonium phosphotungstate nanoparticles, [C12]3[PW12O40], and silica particles functionalized with alkyl and sulfonic acid groups, [Cn/SO3H]@SiO2. The interfacial self-assembly occurs by the penetration of the alkyl chains of [Cn/SO3H]@SiO2 into the [C12]3[PW12O40] supramolecular porous structure constituted of polar and apolar regions. The emulsions were used as a non-nitric acid route for adipic acid synthesis from the one-pot oxidative cleavage of cyclohexene oxide with aqueous H2O2. The catalytic performance was significantly boosted due to the synergistic interactions between the particles.
Polymer supported vanadium complexes as catalysts for the oxidation of alkenes in water
Hsiao, Ming-Chieh,Liu, Shiuh-Tzung
, p. 61 - 66 (2010)
Polymer supported vanadium complexes (denoted as c-PMA n -V) were prepared by the complexation of vanadium ions onto a cross linked polyacrylate. c PMA n -V can catalyze the oxidative cleavage of olefins with a large excess of t-butyl hydroperoxide (TBHP) or bishydroxylation of olefins with 4 eq. of TBHP. Graphical Abstract: [Figure not available: see fulltext.].
Preparation and characterization of WO3 bonded imidazolium sulfonic acid chloride as a novel and green ionic liquid catalyst for the synthesis of adipic acid
Bhuyan, Bishal,Paul, Bappi,Vadivel, Sethumathavan,Dhar, Siddhartha Sankar
, p. 99044 - 99052 (2016)
A novel nano WO3-bonded imidazolium-sulfonic acid chloride (WO3-IL) was prepared, and characterized by FT-IR, XRD, SEM, TEM, EDX and BET. The as synthesized WO3 nanoparticle supported ionic liquid is studied as a heterogeneous catalyst for the liquid phase oxidation of cyclohexene to adipic acid. Apart from cyclohexene, a few other six-eight membered cyclic alcohols and ketones are converted into their dicarboxylic acids in high yields and in short reaction times employing the same reaction protocol. The synergy between the WO3 and ionic liquid is assumed to play a significant role towards its very high catalytic activity. The recyclability of the catalyst is proved to be noteworthy as the catalyst exhibits no significant change in its catalytic activity even after five cycles of reuse.
Chemical compositions of secondary organic aerosol from the ozonolysis of cyclohexene in the absence of seed particles
Sato, Kei
, p. 1584 - 1585 (2005)
The composition of the aerosol from the ozonolysis of cyclohexene in the absence of seed particles has been investigated by laboratory chamber experiments. The aerosol collected on filters was analyzed by a liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry. Low-molecular weight products, i.e., dicarboxylic acids, oxocarboxylic acids, and hydroxydicarboxylic acids, as well as oligomers with molecular weights more than 200 were found in the aerosol. Copyright
Regioselective biotransformations of dinitriles using Rhodococcus sp. AJ270
Meth-Cohn, Otto,Wang, Mei-Xiang
, p. 3197 - 3204 (1997)
A variety of dinitriles have been hydrolysed selectively under very mild conditions using Rhodococcus sp. AJ270. Aliphatic dinitriles NC[CH2]nCN 1 undergo regioselective hydrolysis to give the mono acids 2 with up to 4 methylenes between the nitrile functions while those with n > 4 give the diacids 3 in good yield. Dinitriles NC[CH2]nX[CH2]nCN 4 bearing an ether or sulfide linkage are efficiently transformed into the mono acids 5 when an oxygen is placed β, γ or δ to the cyano group or a β- or γ-sulfur is present. Hydrolysis of N,N-bis(2-cyanoethyl)anilines 4h-j takes place slowly affording exclusively the monoacids 5h-j while the monocyano amides 5o-p are obtained as the sole isolable product from rapid hydrolysis of the corresponding N,N-bis(2-cyanomethyl)butylamine 4o and N,N-bis(3-cyanopropyl)butylamine 4p. Higher homologues of arylimino- and butylimino-dinitriles are inert to enzymatic hydrolysis. A variety of other aliphatic dinitriles have been converted readily into mono acids in good to excellent yields except for o-phenylenediacetonitrile which gives o-phenylenediacetamide as the major product. The title organism also effects the hydrolysis of aromatic dinitriles with regiocontrol such as m- and p-dicyanobenzenes, but nct the ortho-substituted analogue. The scope and limitations of this enzymatic process have been systematically studied and the mechanism of regioselective hydrolysis has been discussed in terms of a chelation-deactivation effect.
Oxidative Cleavage of Vicinal Diols at the Nickel Hydroxide Electrode
Ruholl, Heinrich,Schaefer, Hans J.
, p. 54 - 56 (1988)
Vicinal diols are oxidatively cleaved with good yields by electrolysis at an oxide covered nickel electrode in an aqueous alkaline electrolyte and an undivided cell.The method is applied in the synthesis of optical pure derivatives of 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid.
(-)-Duryne and its homologues, cytotoxic acetylenes from a marine sponge Petrosia sp.
Hitora, Yuki,Takada, Kentaro,Okada, Shigeru,Ise, Yuji,Matsunaga, Shigeki
, p. 1262 - 1267 (2011)
Six linear acetylenes, (-)-duryne (1) and (-)-durynes B-F (2-6), were isolated from the marine sponge Petrosia sp. Their structures were elucidated by NMR and tandem FABMS analyses. The positions of the olefinic bonds were confirmed by ozonolysis experiments, and the absolute configurations were determined by the modified Mosher's method. Compound 1 was found to be the enantiomer of duryne, a previously reported sponge metabolite. Compounds 1-6 show cytotoxicity against HeLa cells with IC50 values between 0.08 and 0.50 μM. (Chemical Equation Presented).
Preparation method of aliphatic dicarboxylic acid
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Paragraph 0079-0080, (2021/03/17)
The invention discloses a preparation method for aliphatic dicarboxylic acids. The preparation method mainly employs acetyl carboxylic acids and/or acetyl carboxylates as raw materials for preparing the aliphatic dicarboxylic acids in a high yield through a nonoxidation process. The preparation technology is simple, efficient, short in flow, less in by-product and suitable for large-scale industrialized production, and the obtained aliphatic dicarboxylic acids are high in purity, and are applicable to synthesize polyesters, polyamides, polyurethanes and other engineering plastic and are used as chemical engineering raw materials and medicine intermediates.
METHOD FOR PRODUCING DICARBOXYLIC ACID
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Paragraph 0115, (2021/05/21)
A method for producing dicarboxylic acid. The method includes: subjecting a raw material system including a cyclic olefin and a lower monocarboxylic acid to an addition reaction in the presence of an addition reaction catalyst to generate an intermediate product system including cyclic carboxylic acid ester; and subjecting the intermediate product system including cyclic carboxylic acid ester to a ring-opening and oxidation reaction in the presence of an oxidant and an oxidation catalyst to generate a corresponding dicarboxylic acid product. The addition reaction in the dicarboxylic acid synthesis route achieves a high single-pass conversion rate, and the selectivity of the corresponding cyclic carboxylic acid ester is high. The addition-oxidation synthesis route achieves faster reaction rates for both the addition reaction and oxidation reaction, and high yield of corresponding dicarboxylic acid product. The addition-oxidation based synthesis route is suitable for continuous, stable and large-scale production of corresponding dicarboxylic acid product.
Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
supporting information, p. 20394 - 20398 (2020/09/21)
A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.
