112-30-1Relevant academic research and scientific papers
Process Development for the Rhodium-Catalyzed Reductive Amination in a Thermomorphic Multiphase System
Künnemann, Kai U.,Bianga, Jonas,Scheel, Ricarda,Seidensticker, Thomas,Dreimann, Jens M.,Vogt, Dieter
, p. 41 - 49 (2020)
For the first time, the successful application of the homogeneously catalyzed reductive amination in a thermomorphic multiphase system (TMS) and the first reported scale-up of this reaction into a continuous process, which recovers and recycles the homogeneous catalyst in flow, is presented. Herein, the model substrate 1-decanal reacts with the secondary amine diethylamine to form the corresponding product N,N-diethyldecylamine. A thermomorphic multiphase system (TMS) is established as a recycling strategy to recover and reuse the catalyst for the continuous process. After screening different solvents for the TMS and optimizing the reaction conditions in batch mode, the recycling of the rhodium catalyst was realized in a fully automated miniplant. Parameters influencing the stability of the process were identified and optimized to develop the continuous process. The process was operated in a steady state over 90 h with yields >90% of the desired product and low catalyst leaching 1%/h.
Reduction of Carboxylic Acid with 2-Propanol over Zirconia-Titania
Takahashi, Kyoko,Shibagaki, Makoto,Kuno, Hideyuki,Matsushita, Hajime
, p. 839 - 840 (1993)
The reduction of long carbon chain carboxylic acids or the esters with 2-propanol proceeded efficiently over zirconia-titania at atmospheric pressure, and the corresponding alcohols were obtained.Methyl 9-octadecenoate was reduced to give 9-octadecen-1-ol in a 58percent yield.
Reduction of aldehydes using trialkylboranes in ionic liquids
Kabalka,Malladi
, p. 2191 - 2191 (2000)
Non-aqueous ionic liquids, molten salts, have been found to enhance organoboron mediated reductions of aldehydes.
Deprotection of mono and dimethoxy phenyl methyl ethers using catalytic amounts of DDQ
Chandrasekhar,Sumithra,Yadav
, p. 1645 - 1646 (1996)
4-Methoxy and 3,4 dimethoxy benzyl ethers have been deprotected with catalytic amounts of DDQ by oxidative recycling of the byproduct DDHQ with FeCl3 for the first time.
Selective Removal of the Methyldiphenylsilyl Protecting Group Using Azide Ion
Monger, Steven J.,Parry, David M.,Roberts, Stanley M.
, p. 381 - 382 (1989)
Sodium azide in dimethylformamide effects the cleavage of the methyldiphenylsilyl ether bond under conditions whereby t-butyldimethylsilyl ethers and t-butyldiphenylsilyl ethers are stable.
Hydrogen transfer hydrozirconation of alkenes with iBuZrCp2Cl catalyzed by Lewis-acidic metal compounds containing Al, Zn, Si, Ag, and Pd
Makabe, Hidefumi,Negishi, Ei-Ichi
, p. 969 - 971 (1999)
The hydrozirconation reaction of monosubstituted alkenes with iBuZrCp2Cl can be significantly accelerated by catalytic amounts of various Lewis acidic metal compounds, most notably AlCl3, Me3SiI, and Pd complexes, such as Li2PdCl4 and Cl2Pd(PPh3)2.
Structure sensitivity in the ruthenium nanoparticle catalyzed aqueous-phase Fischer-Tropsch reaction
Quek, Xian-Yang,Pestman, Robert,Van Santen, Rutger A.,Hensen, Emiel J. M.
, p. 3510 - 3523 (2014)
Low-temperature Fischer-Tropsch reaction data are reported for Ru nanoparticles suspended in the water phase. Their activity and selectivity strongly depends on particle size, when varied between 1 to 5 nm. Small particles display high oxygenates selectivity. The Anderson-Schulz-Flory (ASF) chain-growth probability for oxygenates is significantly lower than that observed for hydrocarbons. The chain growth parameter for hydrocarbon formation is independent of particle size. For oxygenates it is constant only for particles larger than 3 nm. Oxygenate and hydrocarbon formation occur on different sites. The ASF chain-growth probability for oxygenate formation increases with temperature. For very small 1.2 nm particles it shows a maximum as a function of temperature. This unusual temperature dependence is due to relatively slow CO dissociation compared to the rate of C-C bond formation. This journal is
Convenient method for the preparation of catecholborane and promotion of the formation of alkenyl catecholborane using BH3 complexes
Suseela, Y.,Periasamy, M.
, p. 47 - 52 (1993)
Catecholborane is prepared in benzene by passing B2H6, generated from I2/NaBH4, through a suspension of catechol at 25 deg C.The reagent prepared in this way is used for hydroboration-oxidation of representative alkenes and alkynes at 80 deg C.Hydroboration of 1-alkynes followed by iodination with I2/NaOH gives the corresponding trans-1-alkenyl iodides in 70-72percent yield.The alkenyl catecholboranes can be prepared at 25 deg C by performing the reaction in the presence of 10 molepercent of H3B:N(C2H5)2Ph or H3B:THF.The reaction is believed to go through hydroboration of thealkynes by borane followed by exchange with catecholborane.Studies of the preparation of dialkylphenoxyboranes and alkenyldiphenoxyboranes through hydroboration of 1-decene and 1-decyne by use of H3B:N(C2H5)2Ph and phenol are also reported.
Deprotection of benzyl ethers using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under photoirradiation
Rahim, Mohammad Abdur,Matsumura, Shuichi,Toshima, Kazunobu
, p. 7307 - 7309 (2005)
The deprotection of benzyl ethers was effectively realized in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN under photoirradiation using a long wavelength UV light.
Reactions of Amino Acid Decyl Esters with Nucleophiles Catalyzed by Polymer-Supported Amine-Metal Complexes
Ohtani, Noritaka,Inoue, Yukihiko,Inagaki, Yuichi,Fukuda, Kenji,Nishiyama, Taisuke
, p. 1669 - 1676 (1995)
The reactions of alanine decyl ester (AlaODc) with nucleophiles were catalyzed by a crosslinked polystyrene-supported ethylenediamine-copper(II) ion complex (Cu en-PS) under toluene/resin two-phase conditions or toluene/ aqueous buffer/resin three-phase conditions.In the two-phase reactions with octylamine, the rate was increased with a decreasing metal content of the resin.The catalytic efficiency was also dependent on other factors, that is, metal ion, ligand structure, and substrate structure.In the three-phase reactions with water, the hydrolysis was very fast when acetate ions were present in the aqueous phase.It has been suggested that the reactions proceed via a substrate-coordinated intermediate complex under both conditions.
