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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.


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Synthesis of CDMPC in AmimCl.
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Figure 1: Synthesis of CDMPC in AmimCl.

Mentions: As shown in Figure 1, 1.00 g of dry microcrystalline cellulose was transferred into a 100 ml three-neck flask, and the flask was added with 34.00 g of AmimCl (1). The solution was stirred magnetically for dissolution (90°C, 3 h). The flask was added with 10.00 mL of 3, 5-dimethylphenyl isocyanate (2), then the solution was refluxed for 48 h. The whole process was conducted under the protection of N2. After the solution was cooled down, it was added with 800 ml of methanol. The sediment was washed with 200 ml of methanol, and then dried for 12 h under vacuum at 80°C. 2.93 g of white solid of CDMPC was produced with a yield of 79.19%.


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)

Synthesis of CDMPC in AmimCl.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Figure 1: Synthesis of CDMPC in AmimCl.
Mentions: As shown in Figure 1, 1.00 g of dry microcrystalline cellulose was transferred into a 100 ml three-neck flask, and the flask was added with 34.00 g of AmimCl (1). The solution was stirred magnetically for dissolution (90°C, 3 h). The flask was added with 10.00 mL of 3, 5-dimethylphenyl isocyanate (2), then the solution was refluxed for 48 h. The whole process was conducted under the protection of N2. After the solution was cooled down, it was added with 800 ml of methanol. The sediment was washed with 200 ml of methanol, and then dried for 12 h under vacuum at 80°C. 2.93 g of white solid of CDMPC was produced with a yield of 79.19%.

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