3179-63-3Relevant academic research and scientific papers
Hydrogenation of Esters by Manganese Catalysts
Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin
, (2022/01/13)
The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).
REDUCTIVE PREPARATION OF TERTIARY DIMETHYLAMINES FROM NITRILES
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Paragraph 0039, (2017/04/04)
This disclosure describes a low temperature process for the preparation of dimethyl amines from nitriles via reductive amination. In some embodiments, the process proceeds under mild conditions with aqeuous dimethylamine and show an unexpected rate acceleration by the inclusion of an acid addition salt of the dimethylamine.
Reductive amination of nitriles using transfer hydrogenation
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Paragraph 5; 6; 7; 8, (2016/11/09)
This disclosure describes a low temperature process for the preparation of tertiary amines from nitriles and secondary amines via reductive amination using transfer hydrogenation. The process can use a nitrile and a dialkylamine and proceeds under surprisingly mild conditions using a palladium catalyst and the corresponding dialkylammonium formate as the hydrogen donor, and show a pronounced acceleration in the presence of water.
Nanopalladium-catalyzed conjugate reduction of Michael acceptors-application in flow
Nagendiran, Anuja,S?rensen, Henrik,Johansson, Magnus J.,Tai, Cheuk-Wai,B?ckvall, Jan-E.
supporting information, p. 2632 - 2637 (2016/05/24)
A continuous-flow approach towards the selective nanopalladium-catalyzed hydrogenation of the olefinic bond in various Michael acceptors, which could lead to a greener and more sustainable process, has been developed. The nanopalladium is supported on aminofunctionalized mesocellular foam. Both aromatic and aliphatic substrates, covering a variation of functional groups such as acids, aldehydes, esters, ketones, and nitriles were selectively hydrogenated in high to excellent yields using two different flow-devices (H-Cube and Vapourtec). The catalyst was able to hydrogenate cinnamaldehyde continuously for 24 h (in total hydrogenating 19 g cinnanmaldehyde using 70 mg of catalyst in the H-cube) without showing any significant decrease in activity or selectivity. Furthermore, the metal leaching of the catalyst was found to be very low (ppb amounts) in the two flow devices.
Improved Second Generation Iron Pincer Complexes for Effective Ester Hydrogenation
Elangovan, Saravanakumar,Wendt, Bianca,Topf, Christoph,Bachmann, Stephan,Scalone, Michelangelo,Spannenberg, Anke,Jiao, Haijun,Baumann, Wolfgang,Junge, Kathrin,Beller, Matthias
supporting information, p. 820 - 825 (2016/03/09)
Hydrogenation of esters to alcohols with a well-defined iron iPr2PNP pincer complex has been recently reported by us and other groups. We now introduce a novel and sterically less hindered Et2PNP congener that provides superior catalytic activity in the hydrogenation of various carboxylic acid esters and lactones compared to the known complex. Successful hydrogenation proceeds under relatively mild conditions (60°C) with lower catalyst loadings.
Synthesis of scutellarein derivatives to increase biological activity and water solubility
Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Zhang, Wei,Dong, Ze-Xi,Tang, Yu-Ping,Zhang, Peng-Xuan,Gu, Ting,Wu, Wen-Yu,Fang, Fang,Xin-Xue,Li, He-Min,Yang, Jian-Ping,Duan, Jin-Ao
, p. 6875 - 6884 (2015/11/11)
In order to improve the biological activity and water solubility of scutellarin (1), some derivatives of its main metabolite (scutellarein) were designed and synthesized. All the compounds were tested for their thrombin inhibition activity through the analyzation of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity, their water solubility were also assessed by ultraviolet (UV) spectrophotometer. The results showed that compound 8b demonstrated stronger anticoagulant and antioxidant activity, better water solubility compared with scutellarein (2), which warrants it as a promising agent for the treatment of ischemic cerebrovascular disease.
Catalytic hydrogenation of esters. Development of an efficient catalyst and processes for synthesising (R)-1,2-propanediol and 2-(l-Menthoxy)ethanol
Kuriyama, Wataru,Matsumoto, Takaji,Ogata, Osamu,Ino, Yasunori,Aoki, Kunimori,Tanaka, Shigeru,Ishida, Kenya,Kobayashi, Tohru,Sayo, Noboru,Saito, Takao
experimental part, p. 166 - 171 (2012/05/20)
A ruthenium catalyst for the reduction of esters by hydrogenation has been developed. Processes for the hydrogenation of esters have also been developed for (R)-1,2-propanediol and 2-(l-menthoxy)ethanol. The catalyst shows good catalytic activity for the hydrogenation of esters in methanol. Methyl lactate was reduced at 30 °C and gave turnover numbers (TON) up to 4000. The optical purity of the (R)-1,2-propanediol made by the hydrogenation of methyl (R)-lactate was higher than that via the asymmetric hydrogenation of hydroxyacetone. A hydrogenation process to replace the lithium aluminum hydride (LAH) reduction used in the production of 2-(l-menthoxy)ethanol was developed.
METHOD FOR PRODUCING N,N-SUBSTITUTED-3-AMINOPROPAN-1-OLS
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Page/Page column 9, (2011/12/12)
The present invention relates to a process for preparing N,N-substituted 3-aminopropan-1-ols by a) reacting secondary amine with acrolein at a temperature of (?50) to 100° C. and a pressure of 0.01 to 300 bar, and b) reacting the reaction mixture obtained in stage a) with hydrogen and ammonia in the presence of a hydrogenation catalyst at a pressure of 1 to 400 bar, wherein the molar ratio of secondary amine to acrolein in stage a) is 1:1 or more and the temperature in stage b) is in the range from (?50) to 70° C. In a preferred embodiment, acrolein which has been obtained from glycerol based on renewable raw materials is used. The invention further relates to the use of an N,N-dimethyl-3-aminopropan-1-ol (DMAPOL) based on renewable raw materials as a catalyst for polyurethane preparation, as a scrubbing fluid in gas scrubbing, in the electronics chemicals and electroplating sectors, as a feedstock in organic synthesis, and as an intermediate in the production of pharmaceuticals and crop protection compositions.
METHOD FOR PRODUCING N,N-SUBSTITUTED-1,3-PROPANDIAMINES
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Page/Page column 8, (2011/04/18)
The present invention relates to a process for preparing N,N-substituted 1,3-propanediamine by a) reacting secondary amine with acrolein at a temperature of from (?50) to 100° C. and a pressure of from 0.01 to 300 bar, andb) reacting the reaction mixture obtained in stage a) with hydrogen and ammonia in the presence of a hydrogenation catalyst at a temperature of from 40 to 400° C. and a pressure of from 1 to 400 bar, wherein the molar ratio of secondary amine to acrolein in stage a) is 2:1 or more and the hydrogenation catalyst used in stage b) comprises cobalt. In a preferred embodiment, acrolein which has been obtained from glycerol based on renewable raw materials is used. The invention further relates to the use of N,N-dimethyl-1,3-propanediamine (DMAPA) based on renewable raw materials as a feedstock for lubricant soaps and other detergents, coagulants, polymers and comb polymers. In a further preferred embodiment, stage b) is performed in the presence of water.
ALCOHOL PRODUCTION METHOD BY REDUCING ESTER OF LACTONE WITH HYDROGEN
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Page/Page column 14, (2010/04/23)
Provided is an alcohol production method comprising the step of reducing an ester or a lactone with hydrogen to produce a corresponding alcohol without addition of a base compound by using, as a catalyst, a ruthenium complex represented by the following general formula (1): [in-line-formulae]RuH(X)(L1)(L2)n ??(1)[/in-line-formulae] wherein X represents a monovalent anionic ligand,L1 represents a tetradentate ligand having at least one coordinating phosphino group and at least one coordinating amino group or a bidentate aminophosphine ligand having one coordinating phosphino group and one coordinating amino group, andL2 represents a bidentate aminophosphine ligand having one coordinating phosphino group and one coordinating amino group, provided thatn is 0 when L1 is the tetradentate ligand, and n is 1 when L1 is the bidentate aminophosphine ligand.
