Deacylation method of sucralose-6-acetate

A technology of sucralose and acetate, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of impurity removal not being well mentioned, product destruction, sugar substance destruction and other problems

Active Publication Date: 2020-10-23
SHANDONG NHU FINE CHEM SCI & TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Deacylation under alkaline conditions usually has a pH value of 9.5 to 11.5. TGS (sucralose) is usually unstable at this pH value and will continue to decompose with alkali. Therefore, it needs to be used in the later stage of deacylation Extra acid is used to neutralize excess alkali in time, otherwise it will cause product damage, and then the loss of product is inevitable in the process (yield usually has 1 to 3% loss), followed by residual solvent DMF in this process. Disruption occurs during the process, resulting in reduced solvent recovery and increased routing costs
[0011] Acid (mainly proton acid) deacylation is extremely rare. The reason may be that carbohydrates (glycosidic bonds and acetal structures) are more unstable under acidic conditions than under alkaline conditions, and deacylation will also cause The destruction of some sugars, so the deacylation conditions are more stringent when the protonic acid is deacylated. The reported patent (CN101291945A) is carried out under the condition of a catalytic amount of water, and the hydrogen chloride produced by the reaction of the acid chloride and methanol is used. As a catalyst to catalyze the breakage of ester groups, this patent still inevitably uses a catalytic amount of water and alkali to neutralize, and does not mention the removal of impurities well, and according to its records, the sucralose obtained by processing The purity is only 96.8%, meanwhile, the yield is not mentioned

Method used

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  • Deacylation method of sucralose-6-acetate
  • Deacylation method of sucralose-6-acetate
  • Deacylation method of sucralose-6-acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1. Using existing technology to prepare sucralose-6-acetate from sucrose-6-acetate

[0031] Dissolve 6.8kg of phosgene in 11.3kg of n-octane to obtain phosgene n-octane solution, and slowly add it dropwise to the N,N-dimethyl In the formamide (DMF, 24.9kg) solution, the dropwise addition is completed, and the reaction mixture is stirred at room temperature until the system becomes a clear homogeneous solution; then the liquid-liquid two-phase mixture is heated and reacted at 96°C for 13 hours, the reaction is stopped, and the system is cooled To room temperature, stand for stratification, wherein the upper layer is an inert non-polar solvent layer, and the lower layer is a DMF solution layer containing the product; the lower layer is neutralized with ammonia gas or sodium ethoxide ethanol solution, filtered to obtain a filtrate, and then the filtrate is concentrated to obtain a concentrated 5.2kg (contains 2.34kg of sucralose-6-acetate after testing).

Embodiment 2

[0032] Embodiment 2, Lewis acid (anhydrous ZnCl 2 )-mediated deacylation and post-processing

[0033] Take 2.6kg of the neutralized concentrate (containing 1.17kg of sucralose-6-acetate) for deacylation, add 5.2kg of methanol to form a sucralose-6-acetate solution with a content of about 15% , adding anhydrous zinc chloride (0.75kg) and stirring the reaction at an internal temperature of 50° C., the reaction was monitored by HPLC, and the reaction was complete in about 200 minutes.

[0034] Remove methanol from the above solution under reduced pressure, then add 5.2kg of water to dissolve the concentrate, add a small amount of lye (sodium hydroxide) to adjust the pH value to 7.0, so that the zinc salt inside is completely settled in the form of colloid or precipitate, and let stand Filter after 4h, extract the filtrate with 3.5 times EA (ethyl acetate), concentrate, and crystallize through ethyl acetate once (using continuous feeding, pressure 0.07-0.08MPa, internal temperatu...

Embodiment 3

[0035] Embodiment 3, Lewis acid (anhydrous AlCl3 )-mediated deacylation and post-processing

[0036] Take 2.6kg of the neutralized concentrate (containing 1.17kg of sucralose-6-acetate) for deacylation, add 5.2kg of methanol to form a sucralose-6-acetate solution with a content of about 15% , adding anhydrous aluminum chloride (0.75kg) and stirring the reaction at an internal temperature of 20° C., the reaction was monitored by HPLC, and the reaction was complete in about 120 minutes.

[0037] Remove methanol from the above solution under reduced pressure, then add 5.2kg of water to dissolve the concentrate, add a small amount of lye to adjust the pH value to 7.0, so that the aluminum salt inside is completely settled in the form of colloid or precipitation, and after standing for 4 hours, filter to obtain After the filtrate was extracted with 3.5 times of EA, concentrated and crystallized, 1.04 kg of sucralose was obtained with an HPLC purity of 99.9%. The deacylation yield ...

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Abstract

The invention discloses a deacylation method of sucralose-6-acetate. The method comprises the following steps: under the action of Lewis acid, carrying out deacylation reaction on a sucralose-6-acetate-containing reactant in an alcohol solvent; after the reaction is completed, performing concentrating, and adding water; adding alkali liquor to form colloid or precipitate; and removing the colloidor precipitate, and performing purifying to obtain a sucralose product. The deacylation method can reduce the decomposition of TGS (trichlorosucrose), has higher product yield, can better remove impurities in the after-treatment process, and is more convenient to operate.

Description

technical field [0001] The invention belongs to the field of food additive preparation, and in particular relates to a deacylation method of sucralose-6-acetate. Background technique [0002] Sucralose, also known as sucralose and sucralose, is a sweetener developed by Tate & Lyie and the University of London. It has high sweetness, good sweetness, and is not absorbed by the human body. It has the advantages of stable properties and wide application. In industry, sucralose generally uses sucrose as the starting raw material, and is first esterified (protecting the 6-hydroxyl group) to obtain sucrose-6-acetate, and then chlorinated to obtain sucralose-6 -acetate, then carry out deacylation reaction (removal of protecting group) and aftertreatment to obtain sucralose. [0003] In the production of sucralose, the removal of protective groups (deacylation of esters) is generally carried out under the catalysis of alkalis (including inorganic or organic bases). According to dif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H5/02C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H5/02
Inventor 刘钢周有桂赵宇宸王国方严荣伟
Owner SHANDONG NHU FINE CHEM SCI & TECH CO LTD
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