Effect of Dimethyl Sulfoxide on the Retention Time of Acetic Acid in Gas Chromatography and Its Mechanism

doi:10.19894/j.issn.1000-0518.210175

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (5): 852-854.DOI: 10.19894/j.issn.1000-0518.210175

Previous Articles Next Articles

Effect of Dimethyl Sulfoxide on the Retention Time of Acetic Acid in Gas Chromatography and Its Mechanism

Ren MU¹(), Shun NA², Natsagdorj NARANTSOGT¹, Chong-Jiu LI³

^1.Department of Chemistry School of Mathematic and Natural Science Mongolian National University of Education，Ulaanbaatar 210648，Mongolia
^2.Agilent Technologies China Co. ，Ltd. ，Beijing 100102，China
^3.China Agricultural University College of Science，Beijing 100193，China

Received:2021-04-07 Accepted:2021-08-12 Published:2022-05-01 Online:2022-05-24
Contact: Ren MU
About author:muren117@gmail.com

1. Effect of Dimethyl Sulfoxide on the Retention Time of Acetic Acid in Gas Chromatography and Its Mechanism.pdf(107KB)

Abstract

Abstract:

The mechanism for the fluctuation of the retention time of acetic acid dissolved in dimethyl sulfoxide （DMSO） was explored through gas chromatography， infrared spectroscopy， and quantum chemical calculations. Our results indicate that the change in retention time of acetic acid is linearly related to the increase of the volume of DMSO （R²=0.99301）. Infrared spectroscopy analysis shows that a hydrogen bond is formed between DMSO and acetic acid， which passes through the column in the form of DMSO-acetic acid molecules. According to the calculation results of the Gaussian09 program， the high electron density portion of DMSO gives electrons and forms a hydrogen bond with acetic acid， while the portion with the low electron density can easily obtain electrons and form bonds with polyethylene glycol， a column stationary phase with a strong dipole moment， and then adsorb on the fixed liquid. Therefore， under the combined influence of this series of complex intermolecular forces， the retention time of acetic acid fluctuates， and the retention time of acetic acid increases together with the volume ratio of the DMSO solvent.

Key words: Gas chromatography, Retention time, Dimethyl sulfoxide, Acetic acid, Hydrogen bond

CLC Number:

O657

Ren MU, Shun NA, Natsagdorj NARANTSOGT, Chong-Jiu LI. Effect of Dimethyl Sulfoxide on the Retention Time of Acetic Acid in Gas Chromatography and Its Mechanism[J]. Chinese Journal of Applied Chemistry, 2022, 39(5): 852-854.

Figures/Tables 3

Fig.1 Infrared spectrum of SO in gradient DMSO-water solution

Table 1 The changes of each molecular group in the three?phase system of acetic acid， DMSO and water in infrared spectroscopy analysis

项目 Project	二甲基亚砜（SO） DMSO（SO）	乙酸（—OH） CH₃CHOH（—OH）	乙酸（CO） CH₃CHOH（CO）
特征峰 Characteristic peaks	1010	1270	1700
5%CH₃COOH	1016←1010 ^a	1277→1258 ^b	1715←1700 ^a
20%CH₃COOH	1014←1010 ^a	1275→1252 ^b	1715←1700 ^a
50%CH₃COOH	1010→1003 ^b	1264→1237 ^b	1711←1700 ^a

Fig.2 Linear fitting relationship between the change of acetic acid retention time and the volume ratio of DMSO water to NMP water

1	ZHANG Y， CHEN G， GU J， et al. A theoretical study on dimerization and dissociation of acetic acid in ethanol solvent［J］. Comput Theor Chem， 2020， 1191： 113029-113038.
2	ARUNAN E， DESIRAJU G R， KLEIN R A， et al. Definition of the hydrogen bond （IUPAC Recommendations 2011）［J］. Pure Appl Chem，2011， 83（8）： 1637-1641.
3	CHANG X， ZHANG Y， WENG X， et al. Red-shifting versus blue-shifting hydrogen bonds： perspective from ab initio valence bond theory［J］. J Phys Chem A， 2016， 120（17）： 2749-2756.
4	PANUSZKO A， BRUŹDZIAK P， ŚMIECHOWSKI M， et al. DMSO hydration redefined： unraveling the hydrophobic hydration of solutes with a mixed hydrophilic-hydrophobic characteristic［J］. J Mol Liq， 2019， 294： 111661-111672.
5	FORESMAN B J， FRISCH E. Exploring chemistry with electronic structure methods［M］. Second Edition. Pittsburg： Gaussian Inc， 1996： 165-172.

[1]	Jin-Li ZHAO, Zong-Ren YU, Bo-Min SU. Analysis of Egg Whites from Burial Murals by Pyrolysis-Gas Chromatography/Mass Spectrometry [J]. Chinese Journal of Applied Chemistry, 2023, 40(4): 562-570.
[2]	Wei-Qiang ZHANG, Chen WANG, Yu-Rong ZHAO, Dong WANG, Ji-Qian WANG, Hai XU. Research Progress of Regulation of Driving Forces in Short Peptide Supramolecular Self‑Assembly [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1190-1201.
[3]	Dong-Qing CAI, Jing ZHANG, Qing-Chuan WU, Jing-Hong YE, Lin-Ying WANG, Dong-Fang WANG. Preparation and Application of Attapulgite Based Nano⁃controlled Chlorpyrifos [J]. Chinese Journal of Applied Chemistry, 2022, 39(11): 1774-1782.
[4]	Xiao-Ming XIE, Jia-Qi ZHANG. Hydrogen Bond Interaction Driven Procyanidine Assembly into Underwater Adhesive with Antibacterial Activity [J]. Chinese Journal of Applied Chemistry, 2022, 39(10): 1533-1542.
[5]	Meng-Wei LI, Hong-Yan WANG, Ying-Ying WANG, Xiao-Ying KANG, Mei-Fang LIU, Yu-Lan CHEN. Supramolecular Self⁃Assembly of Azobenzene⁃4，4'⁃dicarboxylic Acid Derivatives in Water [J]. Chinese Journal of Applied Chemistry, 2021, 38(10): 1362-1370.
[6]	LI Yingjun, YANG Hongjing, CAO Xin, GAO Lixin, JIN Kun, SHENG Li, LIU Jihong, LIU Xuejie, LI Jia. Synthesis of 3,6-Disubstituted Triazolothiadiazole Derivatives and Their Inhibitory Activities Against Cell Division Cycle 25B Phosphatase and Protein Tyrosine Phosphatase 1B [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 994-1002.
[7]	MA Hao, ZHAO Xue, LI Kunlan, SHAO Guolin, AN Qingda, YANG Liyu, WEI Ligang. Evaluation of Silane Imidazolium Bis(trifluoromethane)sulfonimide Ionic Liquid Stationary Phase for Gas Chromatography [J]. Chinese Journal of Applied Chemistry, 2020, 37(4): 447-454.
[8]	GUO Hongchen, QIN Yusheng, WANG Xianhong. Acetic Acid/Oxygen Route for Efficient Synthesis of Substituted Porphyrin [J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 264-270.
[9]	YU Jiarui, CHEN Shuai, XIN Xing, XU Jingkun. Research and Application Progress on Dimethyl Sulfoxide Modified Poly(3,4-ethylenedioxythiophene): Poly(styrenesulfonic acid) Films [J]. Chinese Journal of Applied Chemistry, 2020, 37(12): 1343-1356.
[10]	CHENG Yinjie, ZHANG Lu, HU Renjie, WANG Ying, JIN Xuexin, QIU Shuo, ZHANG Haoyan, JIANG Dawei. Preparation and Characterization of Hydrogen-Bonded Carbon Nanotubes Reinforced Self-healing Composites [J]. Chinese Journal of Applied Chemistry, 2020, 37(10): 1147-1155.
[11]	DAI Xiaoyu,QIAO Haiyan,HAN Dongyun,CAO Zubin,ZHANG Xingke. Distillation Separation and Gas Chromatography/Mass Spectrometry Analysis of Fushun Ethylene Bottom Oil [J]. Chinese Journal of Applied Chemistry, 2018, 35(6): 714-721.
[12]	WANG Wei, ZHENG Fei, GE Yan, QIAO Mengdan, YUE Hao, LIU Shuying. Analysis of Volatile Components in Processed Ginseng by GC-MS/MS [J]. Chinese Journal of Applied Chemistry, 2017, 34(8): 965-970.
[13]	TIAN Luoyang, CHEN Yali, WANG Qiang. Determination of Thermodynamic Parameters of Organic Solvents in Ionic Liquid 1-Butyl-3-methylimidazolium Hexafluorophosphate by Inverse Gas Chromatography [J]. Chinese Journal of Applied Chemistry, 2017, 34(7): 824-832.
[14]	XIE Fei,WEI Zhixian. Advances on Tetrazole-1-acetic Acid-Based Metal Coordination Polymers [J]. Chinese Journal of Applied Chemistry, 2017, 34(10): 1099-1109.
[15]	ZHANG Hanyun, LIU Manyun, YAN Gang, SHI Deqing. Synthesis of Diamides Containing of 2-Aryloxyacetyl and meta-Trifluoromethylphenyl Moieties and Their Herbicidal Activity [J]. Chinese Journal of Applied Chemistry, 2016, 33(6): 668-676.

Effect of Dimethyl Sulfoxide on the Retention Time of Acetic Acid in Gas Chromatography and Its Mechanism

RichHTML

PDF

Supplement

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 3

References 5

Related Articles 15

Recommended Articles

Metrics

Comments