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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.

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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.


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NMR spectrum of CDMPC.
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Figure 3: NMR spectrum of CDMPC.

Mentions: The obtained CDMPC was also determined by the 1H NMR (400 MHz, 50°C, DMSO-d6). As shown in Figure 3, the chemical shifts (δ, ppm) could be observed at different positions of 8.5-8.9 (N-H), 6.3-7.1 (Ar-H), 3.5-5.1 (Glucose-H), 1.8-2.2 (Ar-CH3).


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)

NMR spectrum of CDMPC.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Figure 3: NMR spectrum of CDMPC.
Mentions: The obtained CDMPC was also determined by the 1H NMR (400 MHz, 50°C, DMSO-d6). As shown in Figure 3, the chemical shifts (δ, ppm) could be observed at different positions of 8.5-8.9 (N-H), 6.3-7.1 (Ar-H), 3.5-5.1 (Glucose-H), 1.8-2.2 (Ar-CH3).

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