刊名:Journal of The American Society for Mass Spectrometry
出版年:2016
出版时间:January 2016
年:2016
卷:27
期:1
页码:144-152
全文大小:2,006 KB
参考文献:1.Lutz, E.F.: Sell higher olefins process. J. Chem. Educ. 63, 202–203 (1986)CrossRef 2.Kuhn, P., Sémeril, D.S., Matt, D., Chetcuti, M.J., Lutz, P.: Structure–reactivity relationships in SHOP-type complexes tunable catalysts for the oligomerisation and polymerisation of ethylene. Dalton Trans. 5, 515–528 (2007)CrossRef 3.Keim, W.: Oligomerization of ethylene to alpha-olefins: discovery and development of the shell higher olefin process (SHOP). Angew. Chem. Int. Ed. 52, 12492–12496 (2013)CrossRef 4.Zhang, W., Sun, W.H., Redshaw, C.: Tailoring iron complexes for ethylene oligomerization and/or polymerization. Dalton Trans. 42, 8988–8997 (2013)CrossRef 5.Park, J.H., Jang, Y.E., Jeon, J.Y., Go, M.J., Lee, J., Kim, S.K., Lee, S.I., Lee, B.Y.: Preparation of ansa-metallocenes for production of poly(alpha-olefin) lubricants. Dalton Trans. 43, 10132–10138 (2014)CrossRef 6.Mitchell, T.W., Pham, H., Thomas, M.C., Blanksby, S.J.: Identification of double bond position in lipids: from GC to OzID. J. Chromatogr. B 877, 2722–2735 (2009)CrossRef 7.Beroza, M., Bierl, B.A.: Rapid determination of olefin position in organic compounds in microgram range by ozonolysis and gas chromatography. Anal. Chem. 39, 1131–1135 (1967)CrossRef 8.Blanksby, S.J., Mitchell, T.W.: Advances in mass spectrometry for lipidomics. Annu. Rev. Anal. Chem. 3, 433–465 (2010)CrossRef 9.Sparvero, L.J., Amoscato, A.A., Dixon, C.E., Long, J.B., Kochanek, P.M., Pitt, B.R., Bayir, H., Kagan, V.E.: Mapping of phospholipids by MALDI imaging (MALDI-MSI): realities and expectations. Chem. Phys. Lipids 165, 545–562 (2012)CrossRef 10.Bang, D.Y., Lim, S., Moon, M.H.: Effect of ionization modifiers on the simultaneous analysis of all classes of phospholipids by nanoflow liquid chromatography/tandem mass spectrometry in negative ion mode. J. Chromatogr. A 1240, 69–76 (2012)CrossRef 11.Hsu, F.F., Turk, J.: Structural characterization of unsaturated glycerophospholipids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J. Am. Soc. Mass Spectrom. 19, 1681–1691 (2008)CrossRef 12.Hsu, F.F., Turk, J.: Elucidation of the double-bond position of long-chain unsaturated fatty acids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J. Am. Soc. Mass Spectrom. 19, 1673–1680 (2008)CrossRef 13.Hsu, F.F., Turk, J.: Electrospray ionization multiple-stage linear ion-trap mass spectrometry for structural elucidation of triacylglycerols: assignment of fatty acyl groups on the glycerol backbone and location of double bonds. J. Am. Soc. Mass Spectrom. 21, 657–669 (2010)CrossRef 14.Yuan, G., Yan, J.: A method for the identification of the double-bond position of isomeric linear tetradecenols and related compounds based on mass spectra of DDD. Rapid Commun. Mass Spectrom. 16, 11–14 (2002)CrossRef 15.Gee, J.C., Prampin, D.S.: Method for determining double-bond positions in mixtures of linear olefins. Anal. Chem. 81, 1646–1651 (2009)CrossRef 16.Kwon, Y., Lee, S., Oh, D.C., Kim, S.: Simple determination of double-bond positions in long-chain olefins by cross-metathesis. Angew. Chem. Int. Ed. 50, 8275–8278 (2011)CrossRef 17.Yang, K., Dilthey, B.G., Gross, R.W.: Identification and quantitation of fatty acid double bond positional isomers: a shotgun lipidomics approach using charge-switch derivatization. Anal. Chem. 85, 9742–9750 (2013)CrossRef 18.Xu, Y., Brenna, J.T.: AP covalent adduct CI tandem MS for double bond localization in monoene- and diene-containing triacylglycerols. Anal. Chem. 79, 2525–2536 (2007)CrossRef 19.Vrkoslav, V., Hakova, M., Peckova, K., Urbanova, K., Cvacka, J.: Localization of double bonds in wax esters by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry utilizing the fragmentation of acetonitrile-related adducts. Anal. Chem. 83, 2978–2986 (2011)CrossRef 20.Thomas, M.C., Mitchell, T.W., Blanksby, S.J.: Ozonolysis of phospholipid double bonds during electrospray ionization. A new tool for structure determination. J. Am. Chem. Soc. 128, 58–59 (2006)CrossRef 21.Thomas, M.C., Mitchell, T.W., Harman, D.G., Deeley, J.M., Murphy, R.C., Blanksby, S.J.: Elucidation of double bond position in unsaturated lipids by ozone electrospray ionization mass spectrometry. Anal. Chem. 79, 5013–5022 (2007)CrossRef 22.Thomas, M.C., Mitchell, T.W., Harman, D.G., Deeley, J.M., Nealon, J.R., Blanksby, S.J.: Ozone-induced dissociation elucidation of double bond position within mass-selected lipid ions. Anal. Chem. 80, 303–311 (2008)CrossRef 23.Poad, B.L., Pham, H.T., Thomas, M.C., Nealon, J.R., Campbell, J.L., Mitchell, T.W., Blanksby, S.J.: Ozone-induced dissociation on a modified tandem linear ion-trap: observations of different reactivity for isomeric lipids. J. Am. Soc. Mass Spectrom. 21, 1989–1999 (2010)CrossRef 24.Ellis, S.R., Hughes, J.R., Mitchell, T.W., in het Panhuis, M., Blanksby, S.J.: Using ambient ozone for assignment of double bond position in unsaturated lipids. Analyst 137, 1100–1110 (2012)CrossRef 25.Pham, H.T., Maccarone, A.T., Thomas, M.C., Campbell, J.L., Mitchell, T.W., Blanksby, S.J.: Structural characterization of glycerophospholipids by combinations of ozone- and collision-induced dissociation mass spectrometry: the next step towards "top-down" lipidomics. Analyst 139, 204–214 (2014)CrossRef 26.Hanley, L., Zimmermann, R.: Light and molecular ions: the emergence of vacuum UV single-photon ionization in MS. Anal. Chem. 81, 4174–4182 (2009)CrossRef 27.Shi, Y.J., Lipson, R.H.: An overview of organic molecule soft ionization using vacuum ultraviolet laser radiation. Can. J. Chem. 83, 1891–1902 (2005)CrossRef 28.Yang, Z., Zhang, T., Pan, Y., Hong, X., Tang, Z., Qi, F.: Electrospray/VUV single-photon ionization mass spectrometry for the analysis of organic compounds. J. Am. Soc. Mass Spectrom. 20, 430–434 (2009)CrossRef 29.Yamamoto, Y., Kambe, Y., Yamada, H., Tonokura, K.: Measurement of gas- and particle-phase organic species in diesel exhaust using vacuum ultraviolet single photon ionization time-of-flight mass spectrometry. Chem. Lett. 41, 292–294 (2012)CrossRef 30.Streibel, T., Mitschke, S., Adam, T., Zimmermann, R.: Time-resolved analysis of the emission of sidestream smoke (SSS) from cigarettes during smoking by photo ionisation/time-of-flight mass spectrometry (PI-TOFMS): towards a better description of environmental tobacco smoke. Anal. Bioanal. Chem. 405, 7071–7082 (2013)CrossRef 31.Cui, H., Hua, L., Hou, K., Wu, J., Chen, P., Xie, Y., Wang, W., Li, J., Li, H.: Coupling of stir bar sorptive extraction with single photon ionization mass spectrometry for determination of volatile organic compounds in water. Analyst 137, 513–518 (2012)CrossRef 32.Yamamoto, Y., Kanno, N., Tonokura, K., Yabushita, A., Kawasaki, M.: Membrane introduction system for trace analysis of volatile organic compounds using a single photon ionization time-of-flight mass spectrometer. Int. J. Mass Spectrom. 296, 25–29 (2010)CrossRef 33.Yamamoto, Y.K.Y., Yamada, H., Tonokura, K.: Measurement of volatile organic compounds in vehicle exhaust using single-photon ionization time-of-flight mass spectrometry. Anal. Sci. 28, 385–390 (2012)CrossRef 34.Xie, Y., Hua, L., Hou, K., Chen, P., Zhao, W., Chen, W., Ju, J., Li, H.: Long-term real-time monitoring catalytic synthesis of ammonia in a microreactor by VUV-lamp-based charge-transfer ionization time-of-flight mass spectrometry. Anal. Chem. 86, 7681–7687 (2014)CrossRef 35.Shi, Y.J., Lo, B., Tong, L., Li, X., Eustergerling, B.D., Sorensen, T.S.: In situ diagnostics of the decomposition of silacyclobutane on a hot filament by vacuum ultraviolet laser ionization mass spectrometry. J. Mass Spectrom. 42, 575–583 (2007)CrossRef 36.Hua, L., Wu, Q., Hou, K., Cui, H., Chen, P., Wang, W., Li, J., Li, H.: Single photon ionization and chemical ionization combined ion source based on a vacuum ultraviolet lamp for orthogonal acceleration time-of-flight mass spectrometry. Anal. Chem. 83, 5309–5316 (2011)CrossRef 37.Hatano, Y.: Interaction of photons with molecules – cross-sections for photoabsorption, photoionization, and photodissociation. Radiat. Environ. Biophys. 38, 239–247 (1999)CrossRef 38.Xie, M., Zhou, Z., Wang, Z., Chen, D., Qi, F.: Determination of absolute photoionization cross-sections of oxygenated hydrocarbons. Int. J. Mass Spectrom. 293, 28–33 (2010)CrossRef 39.Eschner, M.S., Zimmermann, R.: Determination of photoionization cross-sections of different organic molecules using gas chromatography coupled to single-photon ionization (SPI) time-of-flight mass spectrometry (TOF-MS) with an electron-beam-pumped rare gas excimer light source (EBEL): influence of molecular structure and analytical implications. Appl. Spectrosc. 65, 806–816 (2011)CrossRef 40.NIST National Institute of Standards and Technology (NIST). Available at: http://webbook.nist.gov/chemistry/ , accessed June 1 (2015)
作者单位:Yuanyuan Xie (1) (2) Ping Chen (1) Lei Hua (1) Keyong Hou (1) Yongchao Wang (1) Haiyan Wang (3) Haiyang Li (1)
1. Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, People’s Republic of China 2. Graduate University of Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China 3. Jiangsu Province Institute of Quality and Safety Engineering, Nanjing, Jiangsu, 210046, People’s Republic of China
The specific locations of the double bonds in linear olefins can facilitate olefin catalytic synthetic reactions to improve the quality of target olefin products. We developed a simple and efficient approach based on single photon ionization time-of-flight mass spectrometry (SPI-TOFMS) combined with online ozonolysis to identify and quantify the linear olefin double bond positional isomers. The online ozonolysis cleaved the olefins at the double bond positions that led to formation of corresponding characteristic aldehydes. The aldehydes were then detected by SPI-TOFMS to achieve unique spectrometric “fingerprints” for each linear olefin to successfully identify the isomeric ones. To accurately quantify the isomeric components in olefin mixtures, an algorithm was proposed to quantify three isomeric olefin mixtures based on characteristic ion intensities and their equivalent ionization coefficients. The relative concentration errors for the olefin components were lower than 2.5% while the total analysis time was less than 2 min. These results demonstrate that the online ozonolysis SPI-TOFMS has the potential for real-time monitoring of catalytic olefin synthetic reactions.