Synthesis and Application of Carbonated Fatty Acid Esters from Carbon Dioxide Including a Life Cycle Analysis

被引:55
作者
Schaeffner, Benjamin [1 ]
Blug, Matthias [1 ]
Kruse, Daniela [1 ]
Polyakov, Mykola [2 ]
Koeckritz, Angela [2 ]
Martin, Andreas [2 ]
Rajagopalan, Prasanna [2 ]
Bentrup, Ursula [2 ]
Brueckner, Angelika [2 ]
Jung, Sebastian [3 ]
Agar, David [3 ]
Ruengeler, Bettina [4 ]
Pfennig, Andreas [4 ,5 ]
Mueller, Karsten [6 ]
Arlt, Wolfgang [6 ]
Woldt, Benjamin [1 ]
Grass, Michael [1 ]
Buchholz, Stefan [1 ]
机构
[1] Evonik Ind AG, D-45772 Marl, Germany
[2] Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[3] TU Dortmund, Inst Tech Chem B, D-44227 Dortmund, Germany
[4] Rhein Westfal TH Aachen, AVT Therm Verfahrenstech, D-52056 Aachen, Germany
[5] Graz Univ Technol, Inst Chem Engn & Environm Technol, A-8010 Graz, Austria
[6] Univ Erlangen Nurnberg, Lehrstuhl therm Verfahrenstech, D-91058 Erlangen, Germany
关键词
carbon dioxide fixation; fatty acids; homogeneous catalysis; sustainable chemistry; SOYBEAN OIL; ORGANIC CARBONATES; CHEMICAL FIXATION; HYDROGEN-PEROXIDE; METHYL OLEATE; CO2; EPOXIDATION; CATALYSTS; ACRYLATE; TRANSFORMATION;
D O I
10.1002/cssc.201301115
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbon dioxide can be used in various ways as a cheap C1 source. However, the utilization of CO2 requires energy or energy-rich reagents, which leads to further emissions, and therefore, diminishes the CO2-saving potential. Therefore, life cycle assessment (LCA) is required for each process that uses CO2 to provide valid data for CO2 savings. Carbon dioxide can be incorporated into epoxidized fatty acid esters to provide the corresponding carbonates. A robust catalytic process was developed based on simple halide salts in combination with a phase-transfer catalyst. The CO2-saving potential was determined by comparing the carbonates as a plasticizer with an established phthalate-based plasticizer. Although CO2 savings of up to 80% were achieved, most of the savings arose from indirect effects and not from CO2 utilization. Furthermore, other categories have been analyzed in the LCA. The use of biobased material has a variety of impacts on categories such as eutrophication and marine toxicity. Therefore, the benefits of biobased materials have to be evaluated carefully for each case. Finally, interesting properties as plasticizers were obtained with the carbonates. The volatility and water extraction could be improved relative to the epoxidized system.
引用
收藏
页码:1133 / 1139
页数:7
相关论文
共 57 条
[41]   Photocatalytic Water Splitting: Recent Progress and Future Challenges [J].
Maeda, Kazuhiko ;
Domen, Kazunari .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2010, 1 (18) :2655-2661
[42]   Synthesis of cyclic carbonates from epoxides and CO2 [J].
North, Michael ;
Pasquale, Riccardo ;
Young, Carl .
GREEN CHEMISTRY, 2010, 12 (09) :1514-1539
[43]  
Olah G.A., 2006, Beyond Oil and Gas: The Methanol Economy
[44]   Epoxy resin modified with soybean oil containing cyclic carbonate groups [J].
Parzuchowski, Pawel G. ;
Jurczyk-Kowalska, Magdalena ;
Ryszkowska, Joanna ;
Rokicki, Gabriel .
JOURNAL OF APPLIED POLYMER SCIENCE, 2006, 102 (03) :2904-2914
[45]   Mechanistic Details of the Nickel-Mediated Formation of Acrylates from CO2, Ethylene and Methyl Iodide [J].
Plessow, Philipp N. ;
Weigel, Laura ;
Lindner, Ronald ;
Schaefer, Ansgar ;
Rominger, Frank ;
Limbach, Michael ;
Hofmann, Peter .
ORGANOMETALLICS, 2013, 32 (11) :3327-3338
[46]   Selective epoxidation of unsaturated fatty esters over peroxophosphotungstic catalysts (POW) under solvent free conditions Study of the POW catalyst's mechanism [J].
Poli, Evelyne ;
Bion, Nicolas ;
Barrault, Joel ;
Casciato, Stefano ;
Dubois, Vincent ;
Pouilloux, Yannick ;
Clacens, Jean-Marc .
CATALYSIS TODAY, 2010, 157 (1-4) :371-377
[47]   Copper(II) tetrafluroborate-promoted Meinwald rearrangement reactions of epoxides [J].
Robinson, Mathew W. C. ;
Pillinger, Kathryn S. ;
Mabbett, Ian ;
Timms, David A. ;
Graham, Andrew E. .
TETRAHEDRON, 2010, 66 (43) :8377-8382
[48]   Transformation of carbon dioxide [J].
Sakakura, Toshiyasu ;
Choi, Jun-Chul ;
Yasuda, Hiroyuki .
CHEMICAL REVIEWS, 2007, 107 (06) :2365-2387
[49]   Organic Carbonates as Solvents in Synthesis and Catalysis [J].
Schaeffner, Benjamin ;
Schaeffner, Friederike ;
Verevkin, Sergey P. ;
Boerner, Armin .
CHEMICAL REVIEWS, 2010, 110 (08) :4554-4581
[50]   Alumina-catalyzed epoxidation of unsaturated fatty esters with hydrogen peroxide [J].
Sepulveda, Jorge ;
Teixeira, Sergio ;
Schuchardt, Ulf .
APPLIED CATALYSIS A-GENERAL, 2007, 318 (213-217) :213-217