Citation: WANG Tian-He, LIU Ze, WANG Wei-Gang, GE Mao-Fa. Heterogeneous Uptake Kinetics of Limonene and Limonene Oxide by Sulfuric Acid Solutions[J]. Acta Physico-Chimica Sinica, ;2012, 28(07): 1608-1614. doi: 10.3866/PKU.WHXB201204241 shu

Heterogeneous Uptake Kinetics of Limonene and Limonene Oxide by Sulfuric Acid Solutions

WANG Tian-He ^1,2 ,
LIU Ze ¹ ,
WANG Wei-Gang ^1, ,
GE Mao-Fa ^1,

1.
1. State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China;
2. Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received Date: 26 March 2012
Available Online: 24 April 2012
Fund Project: 国家重点基础研究发展规划项目(973) (2011CB403401) (973) (2011CB403401)国家自然科学基金(40925016, 21077109, 41005070)资助 (40925016, 21077109, 41005070)

The heterogeneous uptake of limonene and limonene oxide (also known as 1,8-cineole) by a range of different aqueous sulfuric acid (H₂SO₄) solutions (30%-80% (w)) was investigated to develop an understanding of the reactivity of biogenic organic compounds in the atmosphere towards acidic aerosols. Experiments were performed using a rotating wetted-wall reactor coupled to a single photon ionization time-of-flight mass spectrometer. The heterogeneous uptake of the compounds into H₂SO₄ followed first-order kinetics and the corresponding steady-state uptake coefficients (γ) were calculated for the first time. Limonene oxide was found to be more reactive than limonene towards H₂SO₄. Reactive uptake was observed for limonene oxide in acidic solution containing greater than 30% (w). The steady-state uptake coefficients of limonene oxide in 30%-50% (w) H₂SO₄ solutions at room temperature ranged from (7.100± 0.023)×10^-5 to (8.150±0.162)×10^-3. Furthermore, the reactions of limonene oxide with sulfuric acid in bulk solution were investigated using gas chromatography-mass spectrometry (GC-MS) and electron spray ionization-mass spectroscopy (ESI-MS). Analysis of the products revealed the presence of monoterpenes, terpineols, terpin hydrates, and terpin hydrate diorganosulfate from the bulk solution reaction of limonene oxide with H₂SO₄. The formation of significantly more hydrophobic organic compounds with lower volatilities suggested that limonene oxide is a significant precursor in the formation of atmospheric secondary organic aerosols. A transformation mechanism has been proposed based on the products.
- Limonene,
- Limonene oxide,
- Sulfuric acid,
- Heterogeneous kinetics,
- Steady-state uptake coefficient,
- Organosulfate
1. [1]
  
  (1) Zhu, F. J.; Guo, Y. L. Chin. J. Chem. 2010, 28, 1451. doi: 10.1002/cjoc.201090248
2. [2]
  (2) Comai, S.; Dall'Acqua, S.; Grillo, A.; Castagliuolo, I.; Gurung,K.; Innocenti, G. Fitoterapia 2010, 81, 11. doi: 10.1016/j.fitote.2009.06.017
3. [3]
  (3) Staudt, M.; Bertin, N.; Frenzel, B.; Seufert, G. J. Atmos. Chem.2000, 35, 77. doi: 10.1023/A:1006233010748
4. [4]
  (4) Kesselmeier, J.; Staudt, M. J. Atmos. Chem. 1999, 33, 23. doi: 10.1023/A:1006127516791
5. [5]
  (5) Went, F.W. Nature 1960, 187, 641. doi: 10.1038/187641a0
6. [6]
  (6) Griffin, R. J.; Cocker, D. R.; Flagan, R. C.; Seinfeld, J. H.J. Geophys. Res-Atmos. 1999, 104, 3555. doi: 10.1029/1998JD100049
7. [7]
  (7) Zhang, R. Y. Science 2010, 328, 1366. doi: 10.1126/science.1189732
8. [8]
  (8) Ravishankara, A. R. Science 1997, 276, 1058. doi: 10.1126/science.276.5315.1058
9. [9]
  (9) Esteve,W.; Noziere, B. J. Phys. Chem. A 2005, 109, 10920. doi: 10.1021/jp051199a
10. [10]
  (10) Noziere, B.; Voisin, D.; Longfellow, C. A.; Friedli, H.; Henry, B.E.; Hanson, D. R. J. Phys. Chem. A 2006, 110, 2387.
11. [11]
  (11) Raja, S.; Valsaraj, K. T. Atmos. Res. 2006, 81, 277. doi: 10.1016/j.atmosres.2006.01.004
12. [12]
  (12) Jang, M. S.; Czoschke, N. M.; Lee, S.; Kamens, R. M. Science2002, 298, 814. doi: 10.1126/science.1075798
13. [13]
  (13) Liggio, J.; Li, S. M.; Mclaren, R. Environ. Sci. Technol. 2005,39, 1532. doi: 10.1021/es048375y
14. [14]
  (14) Liu, Z.; Ge, M.; Yin, S.;Wang,W. Chem. Phys. Lett. 2010, 491,146. doi: 10.1016/j.cplett.2010.04.004
15. [15]
  (15) Liu, Z.; Ge, M. F.;Wang,W. G.; Yin, S.; Tong, S. R. Phys. Chem. Chem. Phys. 2011, 13, 2069.
16. [16]
  (16) Howard, C. J. J. Phys. Chem. 1979, 83, 3. doi: 10.1021/j100464a001
17. [17]
  (17) Murphy, D. M.; Fahey, D.W. Anal. Chem. 1987, 59, 2753. doi: 10.1021/ac00150a006
18. [18]
  (18) Hanson, D. R.; Burkholder, J. B.; Howard, C. J.; Ravishankara,A. R. J. Phys. Chem. 1992, 96, 4979. doi: 10.1021/j100191a046
19. [19]
  (19) Fuller, E. N.; Schettle, P.; Giddings, J. C. Ind. Eng. Chem. 1966,58, 19.
20. [20]
  (20) Xu, Z. F.; Liu, Z.; Ge, M. F.;Wang,W. G. Chin. Sci. Bull. 2011,56, 1352. [徐志芳, 刘泽, 葛茂发, 王炜罡. 科学通报, 2011,56, 1352.] doi: 10.1007/s11434-011-4461-8
21. [21]
  (21) Li, Y. J.; Cheong, G. Y. L.; Lau, A. P. S.; Chan, C. K. Environ. Sci. Technol. 2010, 44, 5483. doi: 10.1021/es101231m
22. [22]
  (22) Ferek, R. J.; Lazrus, A. L.; Haagenson, P. L.;Winchester, J.W.Environ. Sci. Technol. 1983, 17, 315. doi: 10.1021/es00112a003
23. [23]
  (23) Matsuura, T.; Komae, H.; Saito, K. B. Chem. Soc. Jpn. 1958, 31,990. doi: 10.1246/bcsj.31.990
24. [24]
  (24) Lombard, R.; Geiger, E. Bull. Soc. Chim. Fran. 1956, 1564.
25. [25]
  (25) Surratt, J. D.; mez- nzalez, Y.; Chan, A.W. H.; Vermeylen,R.; Shahgholi, M.; Kleindienst, T. E.; Edney, E. O.; Offenberg,J. H.; Lewandowski, M.; Jaoui, M.; Maenhaut,W.; Claeys, M.;Flagan, R. C.; Seinfeld, J. H. J. Phys. Chem. A 2008, 112, 8345.doi: 10.1021/jp802310p
26. [26]
  (26) Liggio, J.; Li, S. M. Atmos. Chem. Phys. 2008, 8, 2039. doi: 10.5194/acp-8-2039-2008
27. [27]
  (27) din, S.; Poole, L. R. Scientific Assessment of Ozone Depletion, Global Ozone Research and Monitoring Project-Report No.44; 1998.
1. [1]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
2. [2]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
3. [3]
  Tianqi Bai , Kun Huang , Fachen Liu , Ruochen Shi , Wencai Ren , Songfeng Pei , Peng Gao , Zhongfan Liu . 石墨烯厚膜热扩散系数与微观结构的关系. Acta Physico-Chimica Sinica, 2025, 41(3): 2404024-. doi: 10.3866/PKU.WHXB202404024
4. [4]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
5. [5]
  Qiuping Liu , Yongxian Fan , Wenxian Chen , Mengdi Wang , Mei Mei , Genrong Qiang . Design of Ideological and Political Education for the Preparation Experiment of Ferrous Sulfate. University Chemistry, 2024, 39(2): 116-120. doi: 10.3866/PKU.DXHX202309083
6. [6]
  Yunting Shang , Yue Dai , Jianxin Zhang , Nan Zhu , Yan Su . Something about RGO (Reduced Graphene Oxide). University Chemistry, 2024, 39(9): 273-278. doi: 10.3866/PKU.DXHX202306050
7. [7]
  Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
8. [8]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
9. [9]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
10. [10]
  Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023
11. [11]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
12. [12]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
13. [13]
  Lijun Dong , Pengcheng Du , Guangnong Lu , Wei Wang . Exploration and Practice of Independent Design Experiments in Inorganic and Analytical Chemistry: A Case Study of “Preparation and Composition Analysis of Tetraammine Copper(II) Sulfate”. University Chemistry, 2024, 39(4): 361-366. doi: 10.3866/PKU.DXHX202310041
14. [14]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
15. [15]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
16. [16]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
17. [17]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
18. [18]
  Zeyu XU , Anlei DANG , Bihua DENG , Xiaoxin ZUO , Yu LU , Ping YANG , Wenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099
19. [19]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
20. [20]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

Get Citation

PDF

XML

Metrics

PDF Downloads(786)
Abstract views(2291)
HTML views(39)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142