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Crude reaction product comprising dianhydro sugar alcohol and method for preparing the same

A technology of dianhydrosugar alcohols and reaction products, which is applied in the field of crude reaction products and can solve the problems of decarboxylation of "C-O" units

Inactive Publication Date: 2014-01-01
CHEIL IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, decarboxylation of the "C-O" unit may occur using this method, and thus other ring-free sugar alcohols (xylitol) may be produced as reaction by-products

Method used

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  • Crude reaction product comprising dianhydro sugar alcohol and method for preparing the same
  • Crude reaction product comprising dianhydro sugar alcohol and method for preparing the same
  • Crude reaction product comprising dianhydro sugar alcohol and method for preparing the same

Examples

Experimental program
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Effect test

Embodiment 1

[0058] first cyclization reaction

[0059] In a 20 mL vial containing 5 g of 70% sorbitol in water, add the catalyst p-toluenesulfonic acid (p-TsOH) (9.1 mg, 0.26 wt%) and H 3 PO 2 (35mg, 1.0% by weight). In nitrogen (N 2 ) flow into the system and discharged through the outlet, the mixture was stirred for 16 hours by gradually increasing the temperature to 115°C. NMR measurements of the crude compound formed using AcPh (acetophenone) as an internal standard revealed that the crude compound formed was synthesized as 1,4-sorbitan (35%) and isosorbide (61%) as major products .

[0060] second cyclization reaction

[0061] After adding the catalyst zeolite (630 mg, 18 wt% sorbitol) to the product of the first cyclization reaction, the mixture was stirred for 3 hours under compressed nitrogen (60.0 bar) and elevated temperature (250 °C) . The crude compound thus produced was measured by NMR using AcPh (acetophenone) as an internal standard, and it was found that isosorb...

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Abstract

A crude reaction product includes: (A) about 90 to 100% by weight of a dianhydro sugar alcohol in a solid form and (B) about 0 to about 10% by weight of a reaction byproduct in a solid form. The reaction product is prepared by the steps of (a) preparing a monoanhydro sugar alcohol by reacting a sugar alcohol in the presence of a first cyclization catalyst and (b) preparing a dianhydro sugar alcohol by reacting the monoanhydro sugar alcohol in the presence of a second catalyst.

Description

technical field [0001] The present invention relates to crude reaction products comprising dianhydrosugar alcohols. Background technique [0002] The term sugar alcohol refers to an alcohol having more than two hydroxyl groups formed by reduction of the carbonyl group of a monosaccharide or a compound thereof. Examples of sugar alcohols include, and depending on the number of carbons in, erythritol (C 4 ), threitol (C 4 ), arabitol (C 5 ), xylitol (C 5 ), mannitol (C 6 ), sorbitol (C 6 ), iditol (C 6 )Wait. [0003] Sugar alcohols are not only used in various fields by themselves, but they are also made into mono-anhydrosugars or dianhydrosugars. Mono- and dianhydrosugars can be prepared by cyclodehydration of sugar alcohols as compounds with one or two rings. For example, isosorbide has two rings prepared by cyclodehydration of sorbitol and can be used as a monomer of polyester, polycarbonate, and the like. [0004] US Patent No. 6,818,781 discloses a method for p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 金万锡金善大安盛熙洪尚铉
Owner CHEIL IND INC