Sugar Alcohols. XXI. A Study of the Effect of the Anhydrides of Sorbitol on the Dissociation Constant of Boric Acid.

Bell, Frederick K.; Carr, C. Jelleff; Krantz, John C.

doi:10.1021/j150403a004

Cited by 8 publications

(6 citation statements)

References 1 publication

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“…[7] Crystalline isosorbide was synthesized a few years later, [8] and evidence of its structure was published in 1946. [9] The difference between isosorbide in comparison to its two isomers isoidide and isomannide is the configuration of the two hydroxyl groups.…”

Section: General Facts and Propertiesmentioning

confidence: 99%

“…[36] In comparison to the conventional method using a homogeneous solution and heating for several hours, a highly efficient synthesis for C 8 -alkyl and different aromatic diethers of isosorbide with reaction times of only a few minutes and yields > 90 % has been achieved by using phase-transfer catalysis with microwave heating.…”

Section: Fuels Solvents and Plasticizersmentioning

confidence: 99%

“…Isosorbide, also known as 1,4:3,6-dianhydro-d-glucitol and 1,4:3,6-dianhydro-d-sorbitol, is a V-shaped molecule of two cisconnected tetrahydrofuran rings with an opening angle of 1208 and secondary hydroxyl groups in the 2-and 5-positions ( Figure 1) [6] and it was first reported in 1927. [7] Crystalline isosorbide was synthesized a few years later, [8] and evidence of its structure was published in 1946. [9] The difference between isosorbide in comparison to its two isomers isoidide and isomannide is the configuration of the two hydroxyl groups.…”

Section: General Facts and Propertiesmentioning

confidence: 99%

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Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

2011

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Isosorbide is a platform chemical of considerable importance for the future replacement of fossil resource-based products. Applications as monomers and building blocks for new polymers and functional materials, new organic solvents, for medical and pharmaceutical applications, and even as fuels or fuel additives are conceivable. The conversion of isosorbide to valuable derivatives by functionalization or substitution of the hydroxyl groups is difficult because of the different configurations of the 2- and 5-positions and the resulting different reactivity and steric hindrance of the two hydroxyl groups. Although a substantial amount of work has been published using exclusively the endo or exo derivatives isomannide and isoidide, respectively, as starting material, a considerable effort is still necessary to transfer and adapt these methods for the efficient conversion of isosorbide. This Minireview deals with all aspects of isosorbide chemistry, which includes its production by catalytic processes, special properties, and chemical transformations for its utilization in biogenic polymers and other applications of interest.

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Section: General Facts and Propertiesmentioning

confidence: 99%

Section: Fuels Solvents and Plasticizersmentioning

confidence: 99%

Section: General Facts and Propertiesmentioning

confidence: 99%

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Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

2011

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“…In this paper, we describe the use of both dropin monomers obtained from renewable resources as well as the use of biobased alternatives to currently used raw materials in RMA binder resins. In Scheme 3, the main biobased raw materials featured in this study are shown: biobased diethyl malonate (Bio-DEM TM , used as a drop-in monomer to replace DEM prepared through the petrochemical process), isosorbide (1,4:3,6-dianhydro-D-glucitol) [6][7][8][9] and vegetable oils. Isosorbide is a commercially available, rigid bicyclic secondary diol produced starting from D-glucose.…”

Section: Introductionmentioning

confidence: 99%

Michael addition curable coatings from renewable resources with enhanced adhesion performance

Noordover¹,

Liu²,

McCracken³

et al. 2020

J Coat Technol Res

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Novel malonate-functional polyesters from biobased and potentially biobased monomers were developed and cured through the base-catalyzed carbon-Michael addition reaction with acryloyl-functional oligomers. Both drop-in monomers, such as fully biobased diethyl malonate, and alternative raw materials, such as isosorbide and vegetable oil, were introduced. Isosorbide-based polyesters show improved performance to humidity in terms of adhesion on epoxy-amine primer, while vegetable oil-containing resins lead to improved coating appearance due to better flow and levelling. This study demonstrates that biobased malonate resins, having renewable contents up to 53%, offer attractive performance benefits in 2K RMA paints. It is anticipated that, with the development of additional fully biobased polyols, renewable contents in excess of 80% can be achieved.

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“…In the 1940s, the structures of isosorbide, isomannide and isoidide (i.e. the presence of the 1,4 and the 3,6 anhydro rings as well as the secondary OH-groups) were determined [9,10]. The importance of the DAHs has increased recently due to the stereoconfiguration of these materials, which gave some enhanced properties of synthesized polycondensates [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of Polyester Based on Isosorbide and Butanedioic Acid

et al. 2012

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Copolyesters based on isosorbide and butanedioic acid in combination with monomers such as adipic acid and dimethyl terephthalate, poly(isosorbideco-butanedioic acid) (and -co-adipic acid) and poly(isosorbide-co-butanedioic acid-co-dimethyl terephthalate), were synthesized and characterized. Linear OH-functionalized polyesters were obtained via melt polyesterification of dicarboxylic acids with OH-functional monomers. The type of end-group was controlled by the monomer stoichiometry and hydroxyl functional group is formed in time. Average molecular masses of synthesised polyesters were measured by gel permeation chromatography. The glass transition temperatures and thermal stability of the obtained polyesters were effectively adjusted by varying polymer composition and molar mass. Addition of adipic acid or dimethyl terephthalate increased glass transition temperatures of obtained polyesters. Thermal stability of obtained polyester slightly increases by the increasing of dimethyl terephthalate content. Molecular structures of obtained polyester were assessed by Fourier transform infrared spectra and 1 H NMR spectroscopy.

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Sugar Alcohols. XXI. A Study of the Effect of the Anhydrides of Sorbitol on the Dissociation Constant of Boric Acid.

Cited by 8 publications

References 1 publication

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

Michael addition curable coatings from renewable resources with enhanced adhesion performance

Synthesis and Characterisation of Polyester Based on Isosorbide and Butanedioic Acid

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