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第 9 期 杨 凤，等: 甲基-β-环糊精与芘包合物的制备与表征 ·1593·

2.7 不同温度下甲基-β-环糊精对芘的增溶效果测定 Chemistry (应用化学), 1996, 13(4): 5-9.
[2] Zhang Bin (张斌), Qin Ling (秦岭), Zhang Lingling (张玲玲), et al.
当 MCD 质量浓度为 15 g/L 时，不同温度下
Preparation and characterization of inclusion complex of
MCD 对芘的增溶效果见图 6，在 15 ℃时，MCD 对 β-cyclodextrin and its derivative with chlorpyrifos[J]. Chinese
芘的增溶质量浓度仅为 3.08 mg/L，当温度升高到 Journal of Pesticide Science (农药学学报), 2010, 12(2): 127-134.
[3] Xie Botai (谢伯泰), Ma Xiaoming (马晓明), Yao Sunxian (姚孙贤),
25 ℃后，芘在水中的质量浓度增加到 7.36 mg/L， et al. Characteristic of methylated-β-cyclodextrins and their
为 15 ℃时 2 倍。而 β-环糊精在 15~45 ℃对芘增溶 application in pharmacy[J]. Chinese Journal of New Drugs (中国新
药杂志) ,2009, 18(8):705-709.
时，芘在溶液中的质量浓度从 2.52 mg/L 增加到 5.07
[4] Zhang Xiaoguang(张晓光),Liu Jiexiang(刘洁翔),Fan Zhijin(范志
mg/L。随着温度的升高，MCD 对芘的增溶效果增 金), et al. Advances of research on cyclodextrin and its derivatives
applied inpesticides[J].Chinese Journal of Pesticide Science(农药学
强，芘在水中的溶解度升高，导致水溶液中芘的浓
学报), 2009, 11(3): 291-297.
度增大，使芘与 MCD 的“物理接触频率”增加， [5] Zhou Yan (周妍). The effect on degradation of PAHs polluted soil by
包合反应向有利于生成包合物的方向进行。但由于 microbial reinforcement remediation[D]. Guizhou (贵州): Guizhou
University (贵州大学), 2015.
包合反应属于放热反应，其焓变小于零（ΔH<0）， [6] Viglianti C, Hanna K, Debrauer C. Use of cyclodextrins as an
且是一个熵减少的反应（ΔS<0），整个包合反应是 environmentally friendly extracting agent in organic aged contaminated
一个低温自发，高温非自发的反应 [28] ，因此，温度 soil remediation[J]. Inclusion Phenomena and Macrocyclic
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大于 25 ℃对增溶效果有不利影响。 [7] Marttin E, Verhoef J C, Romeijn S G, et al. Cyclodextrins in nasal
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[8] Cui Haiming (崔海明), Wang Yi (王一), Wang Xiaotao (王晓涛),
et al. Research status repair polycyclic aromatic hydrocarbon
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色科技), 2012, 29(6): 134-136.
[9] Shen Songmei (申松梅), Cao Xianzhong (曹先仲), Song Yanhui (宋
艳辉 ), et al. Nature and the impact of polycyclic aromatic
hydrocarbons[J]. Guizhou Chemical Industry. (贵州化工), 2008,
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[10] Zhu Shilong (朱士龙), Chen Dizhao (陈迪钊), Li Yong (李勇).
Preparation and characterization of sinomenine-β-cylcodextrin
inclusion complex[J]. Chinese Traditional and Herbal Drugs (中草
药), 2012, 43(7): 1328-1332.
图 6 不同温度下 β-环糊精与甲基-β-环糊精对芘的增溶 [11] Sun M M, Mao Y, Feng H, et al. Tenax extraction for exploring
效果 rate-limiting factors in methyl-β-cyclodextrin enhanced anaerobic
Fig. 6 Solubilization curves of β-CD and MCD to pyrene biodegradation of PAHs under denitrifying conditions in a red paddy
under different temperature soil[J]. Journal of Hazardous Materials, 2014, 264(11): 501-513.
[12] Spasojevic J M, Maleti S P, Ronevi S D, et al. Using chemical
3 结论 desorption of PAHs from sediment to model biodegradation during
bioavailability assessment[J]. Journal of Hazardous Materials, 2015,
283: 60-69.
采用饱和溶液法在 25、35、45 ℃下制备了芘 [13] Wang Lihong (王立红), Ding Keqiang (丁克强), Zhao Zhenhua (赵
与 MCD 的包合物 INC。其中，25 ℃下得到包合率 振华), et al. Continuous remediation of pyrene and benzo [a]
pyrene-contaminated soil by cyclodextrin-microbial remediation[J].
最高（39%），说明升高温度不利于包合反应的进行。
Sichuan Environment (四川环境), 2015, 34(6): 5-9.
芘经 MCD 包合后其在水相中的溶解度增加，25 ℃ [14] Li Xiang (李香), Lin Xiuli (林秀丽). The researching progress of
下，芘在水相中的质量浓度达到 7.36 mg/L。UV 测 exosyndrome method used in studying cyclodextrin inclusion
complex[J]. Food and Drug (食品与药品), 2007, 9(7): 35-39.
试结果显示，包合物的紫外吸收峰位置未发生改变， [15] Li Zhongjin (李仲谨), Yang Wei (杨威), Chen Yumiao (陈玉苗),
制备温度为 25、35、45 ℃时，包合物 INC 在 240 nm et al. Preparation and characterization of peppermint
oil-β-cyclodextrin polymer microsphere inclusion compound[J].
处对应吸光度分别为 1.62、1.03、0.87 a.u.。IR、TG、
Chinese Traditional and Herbal Drugs (中草药), 2011, 42(2):
XRD 测试结果显示，芘被 MCD 包合后各特征峰消 271-274.
失、峰形变化或产生位移，包合物的谱图均与 MCD [16] Chen Jianping (陈建平), Zhao Ling (赵玲), Su Jianyu (苏健裕),
et al. Preparation and structure identification of inclusion complex of
谱图类似，这 3 种表征均证明包合物的生成。由于 florfenicol with hydroxypropyl-β-cyclodextrin[J]. Journal of Basic
主客体分子间的相互作用，包合物的热稳定性得到 Science and Engineering (应用基础与工程科学学报), 2013, 21(1):
63-70.
提高。 [17] Wang Lihong (王立红).Continuous remediation of pyrene and
benzo[a]pyrene contaminated soil by hydroxypropyl-β-cyclodextrin-
参考文献： microbial remediation[D]. Nanjing(南京): Hohai University (河海大
[1] Gu Jun (古俊), Chang Yan (常雁), Pan Jinghao (潘景浩). Advances 学), 2016.
in practical applications cyclodextrins[J]. Chinese Journal of Applied （下转第 1608 页）