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Green synthesis of a typical chiral stationary phase of cellulose-tris(3, 5-dimethylphenylcarbamate).

Liu RQ, Bai LY, Zhang YJ, Zhang YP - Chem Cent J (2013)

Bottom Line: The synthesized CDMPC was then coated onto the surfaces of aminopropyl silica gel to prepare a chiral stationary phase (CSP).The prepared CSP was successfully used in chiral separation of seven racemic pesticides by high performance liquid chromatography (HPLC).The experimental results suggested it was a good choice using a green solvent of AmimCl for cellulose functionalization.

View Article: PubMed Central - HTML - PubMed

Affiliation: College of Plant Protection, Hunan Agricultural University, Changsha 410128, P,R, China. blyang2006@163.com.

ABSTRACT

Background: At present, the study on the homogeneous-phase derivatization of cellulose in ionic liquid is mainly focused on its acetylation. To the best of our knowledge, there has been no such report on the preparation of cellulose-tris(3,5-dimethylphenylcarbamate) (CDMPC) with ionic liquid 1-allyl-3-methyl-imidazolium chloride (AmimCl) so far.

Results: With ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl) as a reaction solvent, cellulose-tris(3,5-dimethylphenylcarbamate) (CDMPC) was synthesized by the reaction of 3,5-dimethylphenyl isocyanate and soluble microcrystalline cellulose in a homogeneous phase. The synthesized CDMPC was then coated onto the surfaces of aminopropyl silica gel to prepare a chiral stationary phase (CSP). The prepared CSP was successfully used in chiral separation of seven racemic pesticides by high performance liquid chromatography (HPLC). Good chiral separation was obtained using n-hexane and different modifiers as the mobile phases under the optimal percentage and column temperature, with the resolution of metalaxyl, diniconazole, flutriafol, paclobutrazol, hexaconazole, myclobutanil and hexythiazox of 1.73, 1.56, 1.26, 1.00, 1.18, 1.14 and 1.51, respectively. The experimental results suggested it was a good choice using a green solvent of AmimCl for cellulose functionalization.

Conclusion: CDMPC was successfully synthesized as the chiral selector by reacting 3, 5-dimethylphenyl isocyanate with dissolved microcrystalline cellulose in a green ionic liquid of AmimCl.

No MeSH data available.


Related in: MedlinePlus

FTIR spectra of cellulose and CDMPC. ① Cellulose, ② CDMPC.
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Figure 2: FTIR spectra of cellulose and CDMPC. ① Cellulose, ② CDMPC.

Mentions: FTIR spectra of microcrystalline cellulose and CDMPC were compared in Figure 2. The spectrum of CDMPC had a significantly weaker -OH absorption peak at 3415.31 cm-1, suggesting that the -OH groups of cellulose were mostly replaced. Peak at 2902.34 cm-1 stands for the stretching vibration peak of -CH3 group, the absorption peaks of the benzene ring appeared at 1616.06 cm-1, 1544.70 cm-1 and 1455.99 cm-1, the absorption peak of the carbonyl group was found at 1737.55 cm-1. These all suggest that the -OH groups on microcrystalline cellulose have reacted with 3, 5-dimethylphenyl isocyanate.


Green synthesis of a typical chiral stationary phase of cellulose-tris(3, 5-dimethylphenylcarbamate).

Liu RQ, Bai LY, Zhang YJ, Zhang YP - Chem Cent J (2013)

FTIR spectra of cellulose and CDMPC. ① Cellulose, ② CDMPC.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3750357&req=5

Figure 2: FTIR spectra of cellulose and CDMPC. ① Cellulose, ② CDMPC.
Mentions: FTIR spectra of microcrystalline cellulose and CDMPC were compared in Figure 2. The spectrum of CDMPC had a significantly weaker -OH absorption peak at 3415.31 cm-1, suggesting that the -OH groups of cellulose were mostly replaced. Peak at 2902.34 cm-1 stands for the stretching vibration peak of -CH3 group, the absorption peaks of the benzene ring appeared at 1616.06 cm-1, 1544.70 cm-1 and 1455.99 cm-1, the absorption peak of the carbonyl group was found at 1737.55 cm-1. These all suggest that the -OH groups on microcrystalline cellulose have reacted with 3, 5-dimethylphenyl isocyanate.

Bottom Line: The synthesized CDMPC was then coated onto the surfaces of aminopropyl silica gel to prepare a chiral stationary phase (CSP).The prepared CSP was successfully used in chiral separation of seven racemic pesticides by high performance liquid chromatography (HPLC).The experimental results suggested it was a good choice using a green solvent of AmimCl for cellulose functionalization.

View Article: PubMed Central - HTML - PubMed

Affiliation: College of Plant Protection, Hunan Agricultural University, Changsha 410128, P,R, China. blyang2006@163.com.

ABSTRACT

Background: At present, the study on the homogeneous-phase derivatization of cellulose in ionic liquid is mainly focused on its acetylation. To the best of our knowledge, there has been no such report on the preparation of cellulose-tris(3,5-dimethylphenylcarbamate) (CDMPC) with ionic liquid 1-allyl-3-methyl-imidazolium chloride (AmimCl) so far.

Results: With ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl) as a reaction solvent, cellulose-tris(3,5-dimethylphenylcarbamate) (CDMPC) was synthesized by the reaction of 3,5-dimethylphenyl isocyanate and soluble microcrystalline cellulose in a homogeneous phase. The synthesized CDMPC was then coated onto the surfaces of aminopropyl silica gel to prepare a chiral stationary phase (CSP). The prepared CSP was successfully used in chiral separation of seven racemic pesticides by high performance liquid chromatography (HPLC). Good chiral separation was obtained using n-hexane and different modifiers as the mobile phases under the optimal percentage and column temperature, with the resolution of metalaxyl, diniconazole, flutriafol, paclobutrazol, hexaconazole, myclobutanil and hexythiazox of 1.73, 1.56, 1.26, 1.00, 1.18, 1.14 and 1.51, respectively. The experimental results suggested it was a good choice using a green solvent of AmimCl for cellulose functionalization.

Conclusion: CDMPC was successfully synthesized as the chiral selector by reacting 3, 5-dimethylphenyl isocyanate with dissolved microcrystalline cellulose in a green ionic liquid of AmimCl.

No MeSH data available.


Related in: MedlinePlus