18069-17-5Relevant academic research and scientific papers
CARBOXYLATION OF γ-BUTYROLACTONES WITH CARBON MONOXIDE USING HF-SbF5 SUPER ACID
Yoneda, Norihiko,Suzuki, Akira,Takahashi, Yukio
, p. 767 - 768 (1981)
γ-Butyrolactones react with carbon monoxide at -20 to 30 deg C and at atmospheric pressure in HF-SbF5 super acid media containing an excess of SbF5 to give dicarboxylic acids in good yields.
Sustainable electroorganic synthesis of lignin-derived dicarboxylic acids
Rauen, Anna Lisa,Waldvogel, Siegfried R.,Weinelt, Frank
supporting information, p. 5956 - 5960 (2020/10/18)
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.
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.
Method used for synthesis of 2-methylpentanedioic acid dimethyl ester
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Paragraph 0037-0042; 0044-0049; 0051-0056, (2019/06/30)
The invention provides a method used for synthesis of 2-methylpentanedioic acid dimethyl ester. The method used for synthesis of 2-methylpentanedioic acid dimethyl ester comprises following steps: 2-methyl pentanedinitrile is mixed with an acid, hydrolysis reaction is carried out, an obtained product is allowed to stand so as to obtain an upper layer oil phase and a lower layer water phase; the oil phase and the water phase are separated; the oil phase is mixed with methanol for esterification reaction so as to obtain 2-methylpentanedioic acid dimethyl ester. Operation of the method is simple;technology route is short; raw material consumption is low; and no waste gas, waste water, or waste residue is generated.
PRODUCTION OF A COMPOUND COMPRISING AT LEAST ONE CARBOXYLIC ACID FUNCTIONAL GROUP
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Page/Page column 21; 22, (2015/07/15)
The present invention concerns a process for the production of a compound comprising at least one carboxylic acid functional group, comprising the reaction of a compound comprising at least one nitrile functional group with nitronium ions.
Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.
Low, Choon Heng,Nobbs, James D.,Van Meurs, Martin,Stubbs, Ludger P.,Drent, Eite,Aitipamula, Srinivasulu,Pung, Michelle H. L.
, p. 4281 - 4292 (2015/09/22)
A series of sterically bulky diphosphines have been prepared, including P2 = trans-1,2-bis[(di-tert-butylphosphino)methyl]cyclohexane (4), (2-methylenepropane-1,3-diyl)bis(di-tert-butylphosphine) (5), bis[(di-tert-butylphosphino)methyl]dimethylsilane (6), and cis- and trans-11,12-bis[(di-tert-butylphosphino)methyl]-9,10-dihydro-9,10-ethanoanthracene (10 and 11). The corresponding palladium complexes of these ligands, P2Pd(CF3CO2)2, have been synthesized and characterized. The solid-state structures of [Pd(4)(CF3CO2)2], [Pd(5)(CF3CO2)2], [Pd(6)(CF3CO2)2], and [Pd(11)(CF3CO2)2] were obtained by single-crystal X-ray diffraction and confirm the bidentate binding mode of the ligand and a square-planar coordination geometry with a minor distortion from the ideal. The diphosphines in combination with Pd(OAc)2 have been applied in the hydroxycarbonylation of a mixture of pentenoic acid isomers to produce adipic acid with high selectivity (in several cases >95%). The (regio)selectivity of the hydroxycarbonylation reaction is highly dependent on the P2 diphosphine ligand structure, particularly the steric bulk of the substituents on the diphosphine donor and the P-Pd-P bite angle in the complexes, with respectively tertiary alkyl phosphine substituents (tert-butyl, adamantyl) and a C4 backbone P-Pd-P bite angle >100° being the common features of highly adipic acid selective systems. It is suggested that the regioselectivity of hydroxycarbonylation becomes largely driven by the chelation of the carboxylic acid functionality of pentenoic acid substrates, when smaller size P substituents and/or when P2 ligands with smaller bite angles (100°) are applied.
CONVERSION OF NITRILE COMPOUNDS INTO CORRESPONDING CARBOXYLIC ACIDS AND ESTERS
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Page/Page column 3, (2010/06/19)
Hydrocarbon compounds having at least one nitrile function are converted into compounds having at least one carboxylic function by hydrating the nitrile functions into amide functions by reaction with water in the presence of a strong inorganic acid, and then hydrolyzing the amide functions into carboxylic functions by reaction with water and a strong inorganic acid; the carboxylic compounds thus obtained can be esterified into diesters, advantageously diester solvents.
Enzymatic nitrile hydrolysis catalyzed by nitrilase ZmNIT2 from maize. An unprecedented β-hydroxy functionality enhanced amide formation
Mukherjee, Chandrani,Zhu, Dunming,Biehl, Edward R.,Parmar, Rajiv R.,Hua, Ling
, p. 6150 - 6154 (2007/10/03)
To explore the synthetic potential of nitrilase ZmNIT2 from maize, the substrate specificity of this nitrilase was studied with a diverse collection of nitriles. The nitrilase ZmNIT2 showed high activity for all the tested nitriles except benzonitrile, producing both acids and amides. For the hydrolysis of aliphatic, aromatic nitriles, phenylacetonitrile derivatives and dinitriles, carboxylic acids were the major products. Unexpectedly, amides were found to be the major products in nitrilase ZmNIT2-catalyzed hydrolysis of β-hydroxy nitriles. The hydrogen bonding between the hydroxyl group and nitrogen in the enzyme-substrate complex intermediates that disfavors the loss of ammonia and formation of acyl-enzyme intermediate, which was further hydrolyzed to acid, was proposed to be responsible for the unprecedented β-hydroxy functionality assisted high yield of amide formation.
Regioselective biocatalytic hydrolysis of (E,Z)-2-methyl-2-butenenitrile for production of (E)-2-methyl-2-butenoic acid
Hann, Eugenia C.,Sigmund, Amy E.,Fager, Susan K.,Cooling, Frederick B.,Gavagan, John E.,Bramucci, Michael G.,Chauhan, Sarita,Payne, Mark S.,DiCosimo, Robert
, p. 577 - 581 (2007/10/03)
Acidovorax facilis 72W nitrilase catalyzed the regioselective hydrolysis of (E,Z)-2-methyl-2-butenenitrile, producing only (E)-2-methyl-2-butenoic acid with no detectable conversion of (Z)-2-methyl-2-butenenitrile. (E)-2-Methyl-2-butenoic acid, produced in aqueous solution as the ammonium salt, was readily separated from (Z)-2-methyl-2-butenenitrile, and isolated in high yield and purity. The combination of nitrile hydratase and amidase activities of several Comamonas testosteroni strains were also highly regioselective for the production of (E)-2-methyl-2-butenoic acid from (E,Z)-2-methyl-2- butenenitrile.
Pentenoic acid hydroxycarbonylation method
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Page column 3-4, (2008/06/13)
The invention discloses pentenoic acid hydroxycarbonylation into adipic acid. More particularly, it concerns one pentenoic acid hydroxycarbonylation method involving reaction water and carbon monoxide, in the presence of a catalyst comprising at least rho
