Synthesis of 1,2-propanediamine via reductive amination of isopropanolamine over Raney Ni under the promotion of K2CO3
- 18 Downloads
Catalytic amination of isopropanolamine and ammonia to 1,2-propanediamine over Raney Ni with potassium carbonate as the additive was reported. Characterization of N2 adsorption–desorption and XRD were performed to reveal the textural and structural properties of the catalysts. With the additive of potassium carbonate, the selectivity of 1,2-propanediamine was improved, while the side generation of 2,5-dimethylpiperazine was suppressed. The catalytic reaction parameters were optimized and the yield of 1,2-propanediamine reached 80% under the optimized reaction condition.
KeywordsIsopropanolamine 1,2-Propanediamine Raney nickel Potassium carbonate Reductive amination
We are grateful to be supported by the Key Research and Development Projects of Shanxi Province (Nos. 2017ZDXM-GY-070, 2017ZDXM-GY-042).
- Bahadori A, Nwaoha C, Clark MW (2013) Dictionary of oil, gas, and petrochemical processing. CRC, LondonGoogle Scholar
- Fischer A, Mallat T, Baiker A (1999d) Continuous amination of propanediols in supercritical ammonia. Angew Chem Int Ed 38(3):351–354. https://doi.org/10.1002/(SICI)1521-3773(19990201)38:3%3c351:AID-ANIE351%3e3.0.CO;2-0 Google Scholar
- Imm S, Baehn S, Zhang M, Neubert L, Neumann H, Klasovsky F, Pfeffer J, Haas T, Beller M (2011) Improved ruthenium-catalyzed amination of alcohols with ammonia: synthesis of diamines and amino esters. Angew Chem Int Ed 50:7599–7603, S7599/7591–S7599/7511. https://doi.org/10.1002/chin.201201033
- Lafrance M, Roggen M, Carreira EM (2012) Direct, enantioselective iridium-catalyzed allylic amination of racemic allylic alcohols. Angew Chem Int Ed 51:3470–3473, S3470/3471–S3470/3431. https://doi.org/10.1002/anie.201108287
- Langdon WK, Levis WW Jr, Jackson DR (1962) 2,5-Dimethylpiperazine synthesis from 1-amino-2-propanol. Ind Eng Chem 1(2):153–156Google Scholar
- Liu Q, Zhang T, Liao Y, Cai C, Tan J, Wang T, Qiu S, He M, Ma L (2017a) Production of C5/C6 sugar alcohols by hydrolytic hydrogenation of raw lignocellulosic biomass over Zr based solid acids combined with Ru/C. ACS Sustain Chem Eng 5(7):5940–5950. https://doi.org/10.1021/acssuschemeng.7b00702 Google Scholar
- Liu YX, Zhou K, Shu HM, Liu HY, Lou JT, Guo DC, Wei ZJ, Li XN (2017b) Switchable synthesis of furfurylamine and tetrahydrofurfurylamine from furfuryl alcohol over Raney Nickel. Catal Sci Technol 7(18):4129–4135Google Scholar
- Lu XH, Wei XL, Zhou D, Jiang HZ, Sun YW, Xia QH (2015) Synthesis, structure and catalytic activity of the supported Ni catalysts for highly efficient one-step hydrogenation of 1,5-dinitronaphthalene to 1,5-diaminodecahydronaphthalene. J Mol Catal A Chem 396(396):196–206. https://doi.org/10.1016/j.molcata.2014.08.030 Google Scholar
- Martinez-Asencio A, Ramon DJ, Yus M (2011) N-Alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate: scope and mechanistic considerations. Tetrahedron 67:3140–3149. https://doi.org/10.1016/j.tet.2011.02.075 Google Scholar
- Okamoto Y, Nitta Y, Imanaka T, Teranishi S (1980) Surface state, catalytic activity and selectivity of nickel catalysts in hydrogenation reactions. Part 2: surface characterization of Raney nickel and Urushibara nickel catalysts by X-ray photoelectron spectroscopy. Jchemsocfaraday Trans 76:998–1007. https://doi.org/10.1039/F19807600998 Google Scholar