- Ozonolysis of methylcyclohexanols and methylcyclohexanones
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Ozonolysis of isomeric methylcyclohexanols and methylcyclohexanones was studied.
- Syroezhko,Begak
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Read Online
- Sustainable electroorganic synthesis of lignin-derived dicarboxylic acids
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The oxidative ring opening of lignin-derived alkylated cyclohexanols to bio-based alkylated dicarboxylic acids is successfully performed by an electrocatalytic conversion. To establish this transformation as a green method, we developed a simple protocol for the anodic oxidation at nickel oxide-hydroxide (NiOOH) foam anodes in caustic soda in both a batch and flow electrolysis approach.
- Rauen, Anna Lisa,Waldvogel, Siegfried R.,Weinelt, Frank
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supporting information
p. 5956 - 5960
(2020/10/18)
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- Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
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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.
- Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
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supporting information
p. 20394 - 20398
(2020/09/21)
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- OXIDATIVE CLEAVAGE OF OLEFINS, EPOXIDES AND ALCOHOLS
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Provided is a process for producing a compound I comprising at least one functional group chosen in the group consisting of epoxy group, hydroxyl group and carbonyl group and by reacting a compound J comprising at least one functional group chosen in the group consisting of alkenyl group, epoxy group and hydroxyl group with an an oxidant in the presence of solid amphiphilic catalytic particles A and solid amphiphilic catalytic particles B.
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Page/Page column 23
(2019/02/06)
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- Colloidal tectonics for tandem synergistic Pickering interfacial catalysis: Oxidative cleavage of cyclohexene oxide into adipic acid
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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.
- Yang, Bingyu,Leclercq, Lo?c,Schmitt, Véronique,Pera-Titus, Marc,Nardello-Rataj, Véronique
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p. 501 - 507
(2019/01/10)
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- PRODUCTION OF ADIPIC ACID AND DERIVATIVES THEREOF
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Production of adipic acid and derivatives thereof The invention relates to a catalytic process for the production of a compound of formula (I) from a compound of formula (II)
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Page/Page column 39; 40
(2018/12/03)
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- Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2
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A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.
- Tortajada, Andreu,Ninokata, Ryo,Martin, Ruben
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supporting information
p. 2050 - 2053
(2018/02/19)
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- Complexation of tetrakis(acetato)chloridodiruthenium with naphthyridine-2,7-dicarboxylate - Characterization and catalytic activity
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The reaction of calcium naphthyridine-2,7-dicarboxylate (Cadcnp) with Ru2(OAc)4Cl in water resulted in the formation of Ca[Ru2(dcnp)(OAc)3]2 (3). X-ray crystal structural analysis of 3 confirmed its molecular structure and showed that the calcium ion binds to the lateral carboxylate groups of four neighboring anionic units of [Ru2(dcnp)(μ-OAc)3] and two acetone molecules to form a two-dimensional framework. The RuII-RuII valence state of the diruthenium core was supported by superconducting quantum interference device (SQUID) magnetometry [μeff (300 K) = 2.77 μB]. Complex 3 appears to be an efficient catalyst for the oxidative cleavage of olefins in aqueous media under mild conditions. Typically, the reaction of pulegone with NaIO4 in water catalyzed by 3 (1 mol-%) at 45 C afforded 3-methyladipic acid quantitatively. The reaction of calcium naphthyridine-2,7-dicarboxylate (Cadcnp) with Ru2(OAc)4Cl provides Ca[Ru2(dcnp)(OAc)3]2 as the exclusive product. The complex is catalytically active for the oxidative cleavage of olefins in aqueous media.
- Lee, Chia-Han,Wu, Cai-Ling,Hua, Shao-An,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung
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p. 1417 - 1423
(2015/03/18)
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- Liquid-phase catalytic oxidation of C6-C7 cycloolefins into carboxylic acids in a pseudohomogeneous system
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Liquid-phase oxidation of cyclohexene, methylcyclohexene isomers, and norbornene with a 30% solution of hydrogen peroxide in a pseudohomogeneous system involving highly dispersed compounds of Group-VIb and -VIIIb metals supported by nanosize carbon particles was studied.
- Alimardanov, Kh. M.,Sadygov,Garibov,Abbasov,Abdullaeva, M. Ya.,Dzhafarova
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experimental part
p. 236 - 242
(2011/06/09)
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- PROCESS FOR PRODUCING ALIPHATIC DICARBOXYLIC ACID COMPOUND
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The present invention discloses a process for producing an aliphatic dicarboxylic acid compound, which comprises oxidizing, with a nitrite or a nitrate in the presence of trifluoroacetic acid, an alicyclic secondary alcohol compound or an alicyclic ketone compound, in each of which at least one methylene group is bonded to the carbon atom having hydroxyl group bonded thereto or the carbon atom as a member of carbonyl group, wherein the reaction is conducted in the presence of water of 5 mass % or less relative to 100 mass % of the total of the trifluoroacetic acid and the water.
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Page/Page column 6
(2008/06/13)
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- Efficient oxidation of cycloalkanols by sodium nitrite with molecular oxygen in trifluoroacetic acid
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Oxidation of aliphatic cycloalkanols by sodium nitrite in trifluoroacetic acid gave α,ω-dicarboxylic acids in good yields. Adipic acid was obtained in a quantitative yield from cyclohexanol using 1 equiv of sodium nitrite under oxygen atmosphere but the oxidation required more than 3 equiv of sodium nitrite under nitrogen atmosphere. The oxidation method was applicable to the conversion of 1-alkanols to the corresponding carboxylic acids.
- Matsumura, Yoshihiro,Yamamoto, Yutaka,Moriyama, Noriaki,Furukubo, Shigeru,Iwasaki, Fumiaki,Onomura, Osamu
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p. 8221 - 8224
(2007/10/03)
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- Catalytic osmium-assisted oxidative cleavage of olefins
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An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.
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- A new, modulated, oxidative ring cleavage of α-nitrocycloalkanones by Oxone: Synthesis of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters
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By the appropriate choice of the reaction conditions Oxone produces the ring cleavage of α-nitrocycloalkanones affording good yields of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters, respectively, regardless the ring size and/or the presence of an alkyl group as substituent.
- Ballini, Roberto,Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio
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p. 1049 - 1050
(2007/10/03)
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- Oxidation reactions catalysed by titanium- and chromium-containing silicalites
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While the titanium silicalite-1 (TS-1)-tert-butyl hydroperoxide (TBHP) combination exhibits remarkable activity and selectivity in the oxidative cleavage of the C-C double bond of silyl enol ethers to produce dicarboxylic acids, the chemoselective oxidation of thioethers to sulfoxides without generation of sulfones is achieved using chromium silicalite-2 (CrS-2)-H2O2.
- Raju, Satya V. N.,Upadhya,Ponrathnam,Daniel,Sudalai
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p. 1969 - 1970
(2007/10/03)
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- Rearrangements of Nonracemic Vinyl Phosphates to β-Keto Phosphonates
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A series of chiral auxiliaries has been tested for viability in the vinyl phosphate/β-keto phosphonate rearrangement.While dienyl phosphates derived from ephedrine, pseudoephedrine, and isopinocampheol succumbed to competing elimination reactions, ones derived from menthol and (S)-2-methylbutanol were found to undergo rearrangement to the desired β-keto phosphonates.The bis((S)-2-methylbutyl) phosphorochloridate then was used to prepare the vinyl phosphates of the prochiral ketone 4-methylcyclohexanone, and modest diastereoselectivity was observed upon rearrangement of these phosphates to the corresponding β-keto phosphonates.The de of this rearrangement was established by degradation of the β-keto phosphonate to 3-methyladipic acid and determination of the optical rotation.This sequence allowed identification of the major rearrangement product as the 4R-diastereomer of β-keto phosphonate 13.Finally, two other prochiral cyclohexanones were found to be suitable substrates for the vinyl phosphate/β-keto phosphonate rearrangement.
- An, Yi-Zhong,An, Jian Guo,Wiemer, David F.
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p. 8197 - 8202
(2007/10/02)
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- 1,1-Alkanediol dicarboxylate linked antibacterial agents
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Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula STR1 where A is the residue of certain dicarboxyic acids, R3 is H or (C1 -C3), n is zero or 1 such that when n is zero R is P or B and R1 is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R1 is P and the other is B, and P is STR2 where R2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.
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- Bis-esters of dicarboxylic acids with amoxicillin and certain hydroxymethylpenicillanate 1,1-dioxides
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Antibacterial bis-esters of 1,4-cyclohexanedicarboxylic acids and alkane dicarboxylic acids wherein the ester moieties are derived from different alcohols; one alcohol being hydroxymethylpenicillanate 1,1-dioxide, or the 6-beta-hydroxymethyl or the 6-alpha-aminomethyl derivative thereof; and the other being 6-[D-(2-amino-2-(p-hydroxyphenyl)acetamido)]penicillanic acid (amoxicillin); and pharmaceutically acceptable salts thereof; a method for the use of said esters and their salts, and methods for their preparation.
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- UMLAGERUNG INTERMEDIAERER 1,4-DIRADIKALE BEI DER PHOTOSENSIBILISIERTEN ADDITION VON MALEINSAEUREANHYDRID AN PROPARGYLHALOGENIDE
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Photosensitized addition of maleic anhydride to propargyl bromides and tertiary propargyl chlorides gives rise to formation of vinylcyclopropane derivatives.Results are discussed in terms of a mechanism involving rearrangement of intermediate 1,4-alkyl-vinyl-diradicals.
- Hartmann, Willy,Wendisch, Detlef
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p. 2841 - 2844
(2007/10/02)
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