A kind of preparation method of water-soluble natural vitamin E

A natural vitamin and water-soluble technology, applied in the field of preparation of water-soluble natural vitamin E, can solve the problems of inability to prepare high-purity TPGS, large separation loss of separation means, and incomplete separation at the same time, so as to achieve easy automatic operation and simplified reaction Post-processing operation, to achieve the effect of automatic operation

Active Publication Date: 2020-10-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all methods currently reported in the literature will encounter a common problem:
[0010] 1. The monoester content of TPGS is too low, and contains a large amount of diesterification products;
[0011] 2. Since TPGS has dual characteristics of hydrophilicity and lipophilicity, the post-treatment of the preparation reaction is very difficult and cannot be completed by conventional separation means (due to many reasons such as too much separation loss and incomplete separation at the same time), the reaction process brings The separation of incoming and generated impurities is not clean;
[0012] 3. Unable to prepare high-purity TPGS

Method used

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  • A kind of preparation method of water-soluble natural vitamin E
  • A kind of preparation method of water-soluble natural vitamin E
  • A kind of preparation method of water-soluble natural vitamin E

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the preparation of water-soluble natural vitamin E (TPGS) shown in formula VI

[0046] (1) Preparation of unidirectional loaded PEG1000 resin III

[0047] The reaction formula is as follows:

[0048]

[0049] Add PEG1000II (44g, 44mmol) and 5mL toluene into the reaction flask, heat to 50°C, start stirring, after the PEG1000 melts, add catalyst sodium ethoxide (2.994g, 44mmol) in batches, heat up to 85°C for 1 hour. Add chloromethyl polystyrene resin I (10 g, 1.1 mmol / g chlorine load) successively with tetrahydrofuran (THF) and toluene soaked and swollen for 3 hours in four batches, and then heat up to 130 ° C to continue the reaction for 5 Hour. Stop the reaction, and when the temperature drops to 80°C, filter while it is hot. The filtrate is transferred to a clean container and stored in a sealed container, which can be used in the next similar reaction; the filter cake is washed in the following order: water (100mL×2 times), THF (50mL×1 time), THF / ...

Embodiment 2

[0065] Embodiment 2: the Merrifield resin of different chlorine loads prepares TPGS

[0066]

[0067] (1) The first step reaction: preparation of unidirectional loaded PEG1000 resin III

[0068] Add PEG1000II (4×10×Y g, 4×10×Ymmol, Y is the amount of chlorine loaded on chloromethyl polystyrene resin Ⅰ, the same below) and 5×Y mL toluene into the reaction bottle, heat to 45°C, turn on Stir, after the PEG1000 is melted, add the catalyst sodium ethoxide (4×10×Ymmol) in batches, raise the temperature to 80° C. and react for 1 hour. Then add chloromethyl polystyrene resin I (10 g, Y mmol / g chlorine loading) successively with tetrahydrofuran (THF) and toluene soaked for 3 hours in 4 batches, then raise the temperature to 130 ° C and continue the reaction for 5 hours . Stop the reaction, and when the temperature drops to 80°C, filter while it is hot. The filtrate is transferred to a clean container and stored in a sealed container, which can be used in the next similar reaction...

Embodiment 3

[0075] Embodiment 3 Resin V cleavage reaction prepares TPGS

[0076] The reaction formula is as follows:

[0077]

[0078] Method a: in an autoclave, add the load TPGS resin V (TPGS loading capacity is 0.414mmol / g) and a certain amount of solvent (see Table 2) prepared by step (2) in 5.0g embodiment 1, soak for 6 hours, and then Add a certain amount of palladium carbon (5wt%, that is, the Pd / C with a weight content of 5%) and a certain amount of additives (see Table 2), seal the autoclave, and replace it with nitrogen and hydrogen successively (i.e. into the autoclave). Fill the corresponding gas to 0.5MPa and then vent) 3 times. Fill the autoclave with hydrogen at a certain pressure, raise the temperature and stir to react. The following operations are the same as step (3) of Example 1 to finally obtain TPGS VI, as shown in Table 2.

[0079] Method b: in the reaction flask, add the load TPGS resin V (TPGS load is 0.414mmol / g) and a certain amount of solvent (see Table 2...

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Abstract

The invention discloses a preparation method for water-soluble natural vitamin E. the method comprises the steps that chloromethylated polystyrene resin and PEG1000 serve as raw materials, alkali serves as a catalyst, and reaction is carried out in an organic solvent at 45-135 DEG C so as to obtain PEG1000-loaded resin; under the action of the catalyst, 4-dimethylaminopyridine (DMAP) and tetrahydrofuran, water division reflux reaction is carried out on the PEG1000-loaded resin and d-alpha-tocopherol succinate so as to obtain TPGS-loaded resin; and after the TPGS-loaded resin is soaked by usingmethylbenzene, ethanol, palladium carbon and pyridoxal phosphate are added, and under the atmosphere of 0.8-1.5 MPa of hydrogen , stirring is carried out for reaction for 24 hours at the temperatureof 100-110 DEG C so as to obtain d-alpha-tocopherol polyethylene glycol succinate. According to the synthetic method, the yield of TPGS can reach 97.8%, the TPGS monoester content is 98.6%, and the TPGS diester content is 0.

Description

technical field [0001] The invention relates to a preparation method of water-soluble natural vitamin E represented by formula VI. [0002] Background technique [0003] Water-soluble natural vitamin E, d-α-tocopheryl polyethylene glycol succinate (d-α-TocopherylPolyethylene Glycol Succinate, TPGS), which is composed of d-α-tocopheryl succinate and polyethylene glycol 1000 ( Polymerization degree is 22 to 23) and it is obtained by esterification (VI). It is a white to light brown waxy solid, which is miscible with water and common organic solvents and can exist stably in the air. TPGS contains both the lipophilic group of tocopherol and the hydrophilic group of polyethylene glycol long chain. It is a non-ionic surfactant and an effective tocopherol supplement and absorption enhancer. Various excipients have broad application prospects in the food, pharmaceutical and health care products markets. [0004] d-α-tocopherol has strong physiological and pharmacological activi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/332C08G81/02
CPCC08G65/3326C08G81/025
Inventor 王宇光胡芬朱冰春
Owner ZHEJIANG UNIV OF TECH
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