Aggregation of asphaltene model compounds using a porphyrin tethered to a carboxylic acid

被引:33
作者
Schulze, Matthias [1 ,2 ]
Lechner, Marc P. [1 ,2 ]
Stryker, Jeffrey M. [3 ]
Tykwinski, Rik R. [1 ,2 ]
机构
[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany
[2] Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat ICMM, D-91054 Erlangen, Germany
[3] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
MOLECULAR-ORBITAL CALCULATIONS; CRUDE OILS; PETROLEUM; CHLOROPHYLL; DERIVATIVES; CHEMISTRY; CRACKING; WATER; ASSOCIATION; BITUMEN;
D O I
10.1039/c5ob00836k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ni(II) porphyrin functionalized with an alkyl carboxylic acid (3) has been synthesized to model the chemical behavior of the heaviest portion of petroleum, the asphaltenes. Specifically, porphyrin 3 is used in spectroscopic studies to probe aggregation with a second asphaltene model compound containing basic nitrogen (4), designed to mimic asphaltene behavior. NMR spectroscopy documents self-association of the porphyrin and aggregation with the second model compound in solution, and a Job's plot suggests a 1 : 2 stoichiometry for compounds 3 and 4.
引用
收藏
页码:6984 / 6991
页数:8
相关论文
共 60 条
[1]   Association behavior of pyrene compounds as models for asphaltenes [J].
Akbarzadeh, K ;
Bressler, DC ;
Wang, JN ;
Gawrys, KL ;
Gray, MR ;
Kilpatrick, PK ;
Yarranton, HW .
ENERGY & FUELS, 2005, 19 (04) :1268-1271
[2]   The Peak of the Oil Age - Analyzing the world oil production Reference Scenario in World Energy Outlook 2008 [J].
Aleklett, Kjell ;
Hook, Mikael ;
Jakobsson, Kristofer ;
Lardelli, Michael ;
Snowden, Simon ;
Soderbergh, Bengt .
ENERGY POLICY, 2010, 38 (03) :1398-1414
[3]   Effect of Chemical Structure on the Cracking and Coking of Archipelago Model Compounds Representative of Asphaltenes [J].
Alshareef, Ali H. ;
Scherer, Alexander ;
Tan, Xiaoli ;
Azyat, Khalid ;
Stryker, Jeffrey M. ;
Tykwinski, Rik R. ;
Gray, Murray R. .
ENERGY & FUELS, 2012, 26 (03) :1828-1843
[4]   Modeling Asphaltene Aggregation with a Single Compound [J].
Breure, Bianca ;
Subramanian, Deepa ;
Leys, Jan ;
Peters, Cor J. ;
Anisimov, Mikhail A. .
ENERGY & FUELS, 2013, 27 (01) :172-176
[5]   Highly efficient porphyrin sensitizers for dye-sensitized solar cells [J].
Campbell, Wayne M. ;
Jolley, Kenneth W. ;
Wagner, Pawel ;
Wagner, Klaudia ;
Walsh, Penny J. ;
Gordon, Keith C. ;
Schmidt-Mende, Lukas ;
Nazeeruddin, Mohammad K. ;
Wang, Qing ;
Gratzel, Michael ;
Officer, David L. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2007, 111 (32) :11760-11762
[6]   Addition Reactions of Olefins to Asphaltene Model Compounds [J].
Cardozo, Samuel D. ;
Schulze, Matthias ;
Tykwinski, Rik R. ;
Gray, Murray R. .
ENERGY & FUELS, 2015, 29 (03) :1494-1502
[7]   Investigation of Asphaltene Chemical Structural Modification Induced by Thermal Treatments [J].
Chiaberge, Stefano ;
Guglielmetti, Gianfranco ;
Montanari, Luciano ;
Salvalaggio, Mario ;
Santolini, Luciano ;
Spera, Silvia ;
Cesti, Pietro .
ENERGY & FUELS, 2009, 23 (09) :4486-4495
[8]  
Chianelli R. R., 2014, US Patent, Patent No. [2014/0234026, 20140234026]
[9]   STEREOSELECTIVE ADDITION OF R2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - INTRAMOLECULAR ASSISTANCE AND SOLVENT EFFECTS [J].
CHRISTENSON, B ;
HALLNEMO, G ;
ULLENIUS, C .
TETRAHEDRON, 1991, 47 (26) :4739-4752
[10]   STUDIES IN PORPHYRIN CHEMISTRY - A SYNTHETIC APPROACH [J].
CLEZY, PS .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (09) :1163-1193