4048-33-3Relevant academic research and scientific papers
Sequential hydroaminomethylation/Pd-catalyzed hydrogenolysis as an atom efficient route to valuable primary and secondary amines
October, Jacquin,Mapolie, Selwyn F.
supporting information, (2021/04/12)
The facile synthesis of valuable primary and secondary amines is reported using a sequential procedure of hydroaminomethylation and Pd-catalyzed hydrogenolysis. The hydroaminomethylation reaction was catalyzed by a cationic Rh(I) iminopyridyl complex and the N-alkylated benzylamines were produced with high chemoselectivity, albeit as mixtures of linear and branched products. Performing the hydrogenolysis reaction using 10% Pd/C, provided access to valuable primary and secondary amines which have applications in the surfactant, pharmaceutical and polymer industries.
METHOD FOR PRODUCING HEXAMETHYLENE DIAMINE
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Paragraph 0033-0055, (2021/02/13)
To provide a method for producing hexamethylene diamine from 1,6-hexanediol and ammonia, under easy-to-control mild conditions.SOLUTION: A method for producing hexamethylene diamine includes reacting 1,6-hexanediol with ammonia in the presence of a solvent by means of a noble metal-supporting catalyst.SELECTED DRAWING: None
Synthesis method of 6-amino-1-hexanol
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Paragraph 0021-0056, (2020/09/30)
The invention relates to a synthesis method of 6-amino-1-hexanol. The synthesis method comprises the following steps: adding toluene and caprolactam into a reaction vessel, stirring, adding alkali into the reaction vessel in the stirring process, cooling the reaction temperature to the room temperature to obtain a primary reaction solution; slowly dropwise adding a red aluminum solution into the primary reaction solution, heating to carry out a reaction after dropwise adding so as to obtain a secondary reaction solution; cooling the secondary reaction solution, dropwise adding a quenching solution, continuously stirring for 15 minutes after dropwise adding, adding diatomite into the reaction vessel, stirring, filtering, carrying out reduced pressure distillation on the filtrate, and collecting fractions, thereby obtaining 6-amino-1-hexanol. The method has the advantages that the 6-amino-1-hexanol is synthesized from caprolactam by using red aluminum as a reducing agent, compared with existing rhodium and silver catalysts, the catalyst has the characteristics of short reaction time, mild conditions, low cost, simple process and the like, the maximal yield can reach 87%, and large-scale production is easy to realize.
Method for preparing aliphatic amine compound
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Paragraph 0071-0073, (2020/05/14)
The invention discloses a method for preparing an aliphatic amine compound, comprising the following steps: using furfuryl amine or a furfuryl amine derivative as a raw material, and carrying out hydrogenolysis in the presence of a supported metal catalyst to obtain the aliphatic amine compound. According to the method disclosed by the invention, the aliphatic amine compound is prepared by catalyzing hydrogenolysis of the biomass-based furfuryl amine and the derivative thereof for the first time. The catalyst has high activity and high product selectivity. According to the method, a biomass-based compound is used as a raw material to prepare the aliphatic amine compound, and the requirements of sustainable development and green chemistry are met. The aliphatic amine compound prepared by the method has high selectivity, and is convenient for separation and purification of products. After the reaction of the method is finished, the catalyst is easy to separate and can be recycled, so that the method has a good application prospect.
Synthetic method 6-amino-1-hexanol
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, (2019/10/23)
The invention discloses a synthetic method 6-amino-1-hexanol. According to the synthetic method 6-amino-1-hexanol, chlorosulphonyl isocyanate and 1, 6-hexanediol are taken as main raw materials, one-pot method is adopted to synthesize 6-amino-1-hexanol. The synthesis route comprises following steps: 1, under the catalyst effect of a tertiary amine, chlorosulphonyl isocyanate and a primary alcoholare reacted to generate a Burgess reagent, 1, 6-hexanediol is added to generate an intermediate 6-hydroxyhexyl carbamic acid; and 2, the intermediate 6-hydroxyhexyl carbamic acid synthesized in step is subjected to projecting group removing directly without separation so as to obtain target product 6-amino-1-hexanol. The synthetic method is low in cost, simple in reaction conditions, few in reaction steps, short in time, and high in purity and yield of finished product 6-amino-1-hexanol.
Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols
Chen, Jiangbo,Wang, Jiaquan,Tu, Tao
supporting information, p. 2559 - 2565 (2018/07/30)
By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.
Highly efficient nitrobenzene and alkyl/aryl azide reduction in stainless steel jars without catalyst addition
Martina, Katia,Baricco, Francesca,Tagliapietra, Silvia,Moran, Maria Jesus,Cravotto, Giancarlo,Cintas, Pedro
supporting information, p. 18881 - 18888 (2018/11/26)
The mechanochemical and selective reduction of aryl nitro and aryl/alkyl azide derivatives, with either formate salts or hydrazine, to the corresponding, synthetically useful amines occurs in excellent yields in a planetary ball mill without the addition of a catalyst. This newly developed and solvent-free protocol is efficient, fast and does not require the addition of a metal hydrogenation catalyst as the stainless steel jar itself fulfils that role. The method has been applied to a broad range of compounds and excellent yields have been obtained. The formylation of alkyl amines has been successfully performed, by means of mechanochemical activation, in the presence of ammonium formate alone.
Direct Hydrogenation of a Broad Range of Amides under Base-free Conditions using an Efficient and Selective Ruthenium(II) Pincer Catalyst
Wang, Zheng,Li, Yong,Liu, Qing-Bin,Solan, Gregory A.,Ma, Yanping,Sun, Wen-Hua
, p. 4275 - 4281 (2017/12/02)
The ruthenium(II) complex, [fac-PNHN]RuH(η1-BH4)(CO) (B; PNHN=8-(2-diphenylphosphinoethyl)aminotrihydroquinoline), is a highly versatile and effective catalyst (loadings of 0.1–1 mol %) for the hydrogenation of a multitude of amides, which include primary, secondary, and tertiary amides, to give their corresponding alcohols and amines in high yields under base-free conditions. All products were confirmed by using GC and GC–MS.
Tris(2-carboxyethyl)phosphine promotes hydrolysis of iminoboronates
Liu, Xiaoyu,Li, Zhihong,Xu, Hongtao,Zhan, Yuexiong,Ma, Peixiang,Chen, Hongli,Jiang, Biao
, p. 3101 - 3106 (2017/07/18)
Iminoboronates are stable and formed fast. Their B[sbnd]N bonds could be reverted by some endogenous biological molecules. The reversible characteristic attracts significant attention in biological and chemical fields. Although synthesis of iminoboronates is well-studied, less efforts have been devoted to disconnecting the units. Here, a series of selected compounds were screened to evaluate their hydrolytic capability of iminoboronates by 1H NMR or 11B NMR detection. Tris(2-carboxyethyl)phosphine (TCEP), was emerged as an excellent reagent, which decomposed most iminoboronates in short time with high yields. In addition, TCEP is also able to hydrolyze hydrazones and oximes with moderate yields.
Reductive amination of 1,6-hexanediol with Ru/Al2O3 catalyst in supercritical ammonia
Li, Yan,Cheng, Haiyang,Zhang, Chao,Zhang, Bin,Liu, Tong,Wu, Qifan,Su, Xinluona,Lin, Weiwei,Zhao, Fengyu
, p. 920 - 926 (2017/07/05)
Hexamethylenediamine (HMDA) is an important reagent for the synthesis of Nylon-6,6, and it is usually produced by the hydrogenation of adiponitrile using a toxic reagent of hydrocyanic acid. Herein, we developed an environmental friendly route to produce HMDA via catalytic reductive amination of 1,6-hexanediol (HDO) in the presence of hydrogen. The activities of several heterogeneous metal catalysts such as supported Ni, Co, Ru, Pt, Pd catalysts were screened for the present reaction in supercritical ammonia without any additives. Among the catalysts examined, Ru/Al2O3 presented a high catalytic activity and highest selectivity for the desired product of HMDA. The high performance of Ru/Al2O3 was discussed based on the Ru dispersion and the surface properties like the acid-basicity. In addition, the reaction parameters such as reaction temperature, time, H2 and NH3 pressure were examined, and the reaction processes were discussed in detail.
