Synthesis of Cellulose Tricarbonates in 1‐Butyl‐3‐methylimidazolium Chloride/Pyridine

Abstract

Cellulose phenyl tricarbonates could be synthesized by a novel and fast procedure applying 1-butyl-3-methylimidazolium chloride/pyridine as reaction medium. Even cellulose phenyl carbonates with high degree of substitution are accessible at low molar ratio very efficiently. The reagent phenyl chloroformate is inert in the mixture, which is different from the solvent N,N-dimethylacetamide/LiCl that is usually applied. The products were characterized in detail by two-dimensional NMR- and FTIR-spectroscopy, elemental analysis, and size-exclusion chromatography. This class of cellulose derivatives is a very important intermediate for the design of structures based on cellulose by nucleophilc attack on the carbonyl group.

Synthesis of Cellulose Methylcarbonate in Ionic Liquids using Dimethylcarbonate

“…From ATR-IR, the appearance carbonyl stretching frequencies at 1720 cm À1 supports the introduction of carbonate groups into cellulose ( Figure 1). The HMBC spectrum (Supporting Information, Figure S11) shows the main correlation to be between the carbonyl peak in the 13 C dimension [20] and Elschner et al [13] The peak listings are given in Table 2. In order to further prove the formation of cellulose alkylcarbonates, NMR spectroscopy was also applied.…”

Synthesis of Novel Cellulose Carbamates Possessing Terminal Amino Groups and Their Bioactivity

“…Cellulose phenyl carbonates are an interesting class of novel soluble cellulose derivatives that can be easily modified by nucleophilic displacement reactions at the carbonyl C‐atom applying various nucleophiles like amines of different structure . The cellulose phenyl carbonates could be easily synthesized by a homogeneous conversion of cellulose dissolved in N , N ‐diemthylacetamide (DMA)/LiCl or in a mixture of ionic liquid/pyridine . The cellulose phenyl carbonates used as starting material in the present studies were obtained by the homogenous reaction of microcrystalline cellulose dissolved in DMA/LiCl with phenyl chloroformate .…”

“…An alternative, efficient, and promising path to generate polymers containing amino groups is the aminolysis of polysaccharide carbonates . The chemical modification of cellulose phenyl carbonates turned out to be an excellent platform to obtain a broad variety of novel cellulose derivatives.…”

Rapid Flow Through Immunoassay for CRP Determination Based on Polyethylene Filters Modified withω-Aminocellulose Carbamate

“…To obtain uniform, rigid thin films of ω‐aminocellulose carbamates, the coating has to be carried out at pH value of 10 . Cellulose carbamates are obtained by aminolysis of the corresponding carbonic acid ester that may possess even a complete functionalization, i. e., a DS of 3 and thus the density of functional groups could be significantly increased …”