Continuous medium pressure column chromatography process for preparing high purity isodecyl decaprenyl alcohol

A deca isoprenyl alcohol and high-purity technology, which is applied in the field of preparing high-purity isodeca isoprenyl alcohol by continuous medium pressure column chromatography, and can solve the problem of low content of isodeca isoprenyl alcohol. , can not meet the problems of industrial production, unstable properties of solanesol, etc., to achieve the effect of high product yield, convenient industrial continuous production, and reduced production costs

Inactive Publication Date: 2009-10-21
KUNMING TONGFA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the properties of solanesol are unstable, it will be partially decomposed or self-dehydrated and condensed during the reaction process to produce by-products. The content of isodecadecaprenyl alcohol obtained is relatively low, and the intermediate process is not refined, so it cannot be used very well. Coenzyme Q is prepared by condensation 10 , according to the general refining methods such as extraction and crystallization, the efficiency is low and cannot meet the needs of industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Weigh 100g of 160-200 mesh activated silica gel, slowly and evenly load it into a stainless steel chromatography column with a column length of 500cm and an inner diameter of 55mm, use a vacuum of -0.08Mpa to remove the air in the column, and dry it for 30min. Slowly enter No. 6 solvent oil until the column is completely filled, pump No. 6 solvent oil from the top to compact the column under continuous pressure for 8 hours to remove air bubbles, and the pressure is controlled at 0.2Mpa. Take by weighing 25g content and be the crude product of isodecadecaprenyl alcohol of 69%, add No. 6 mineral spirits 16.5g, stir and make whole dissolving, sample injection with pump, use the mixed solution of No. 6 mineral spirits and ethyl acetate ( 100:1-80:1) gradient elution, fractions were collected in sections, monitored by TLC, combined to collect the eluent with a content of more than 95%, and recovered the eluent under reduced pressure to obtain 16.8 g of isocyanate with a purit...

Embodiment 2

[0024] Use a vacuum of -0.08Mpa to remove the air in the dry column of Example 1, dry it for 30 minutes, slowly enter No. 6 solvent oil from the bottom of the column until the column is completely filled, pump No. 6 solvent oil from the top and continue to pressurize Under the state, the dense column will drive out the air bubbles for 8 hours, and the pressure will be controlled at 0.2Mpa. Weigh 25g of crude isodecadecaprenyl alcohol with a content of 75%, operate according to the operation method of Example 1, and obtain 18.2g of pure isodecadecaprenyl alcohol with a purity of 97.8%. The yield is was 94.9%.

Embodiment 3

[0026] Weigh 6Kg of 300-500 mesh activated silica gel, slowly and evenly load it into a stainless steel chromatography with an effective column length of 300mm and an inner diameter of 300mm, vacuum-0.8Mpa to remove the air in the column, and dry it for 30min. Slowly enter the n-hexane at the bottom until the column is completely filled, pump the n-hexane to compact the column for 8 hours under continuous pressure, drive away the air bubbles, weigh 1Kg of the crude product of isodecadecaprenyl alcohol with a content of 70%, add n-hexane Heat 0.5Kg of alkane (50°C) to dissolve and load the sample, elute with a mixture of n-hexane and ethyl acetate (100:1-60:1), collect fractions in sections, monitor by TLC, spot the plate and collect the content The eluent is more than 95%, and the eluent is recovered under reduced pressure to obtain 0.68kg of pure isodecadecaprenyl alcohol with a purity of 98%, and the polarity of the eluent is increased to 98% ethyl acetate Esters, eluting th...

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Abstract

A method for preparing high-purity isodecadecaprenyl alcohol by continuous medium-pressure column chromatography. The method uses crude isodedecadecaprenyl alcohol with a content of not less than 65% as a raw material, and the preparation purity reaches 95% % more than pure isodecadecaprenyl alcohol. This method uses a medium-pressure silica gel-packed column. The dry-packed column is pressurized and compacted with a hydrocarbon solvent. The sample is dissolved in the hydrocarbon solvent. Liquid, the eluted fractions were collected in sections, concentrated under reduced pressure to recover the eluent, and concentrated to dryness to obtain pure isodecadecaprenyl alcohol with a purity of more than 95%. After use, the chromatographic column is heated to N2 to dry the solvent and can be used repeatedly. The main features of the method are reduced production cost, short production cycle, high product yield and high purity, all solvents used can be recycled and used mechanically, and are convenient for industrialized continuous production.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a method for preparing high-purity isodecadecaprenyl alcohol by continuous medium-pressure column chromatography. Background technique [0002] Isodecadecaprenyl alcohol is a synthetic coenzyme Q 10 The necessary raw material for the synthesis of coenzyme Q 10 The "side chain" of coenzyme Q 0 Condensation of hydroquinone to get coenzyme Q 10 . Among them, the purity of isodecadecaprenyl alcohol directly affects the coenzyme Q 10 Synthetic yield and quality. [0003] The synthetic method literature of isodecadecaprenyl alcohol has been reported, such as: [0004] 1) Rueggt et al., J Helv Chem Acta, 1959, 42: 2616-1621 [0005] 2) Naruta et al., J org chem. 1980, 45(21): 4091-4104 [0006] 3) Daniel Dacvid West, US 2002 / 0156302 A1 [0007] Several methods all use solanesol as raw material to obtain isodecadecaprenyl alcohol after bromination, condensation and h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/02C07C29/76
Inventor 申醒王国平朱锡英符涛
Owner KUNMING TONGFA IND
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