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Method of production of vitamin E

A derivative and epoxy technology, applied in organic chemical methods, bulk chemical production, organic chemistry, etc., can solve problems such as high cost

Inactive Publication Date: 2001-08-15
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Geranylgeraniol is available from plant or microbial sources but at high cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] This example illustrates the preparation of 2,3-epoxygeranylgeraniol in which the epoxidation is carried out in toluene with tert-butyl hydroperoxide in the presence of vanadium.

[0102] A solution of 5.0 g (0.0172 mol) of geranylgeraniol in 25 ml of toluene was treated with 50 mg of tris(acetylacetonate) vanadium (0.8 mol%), stirred under reflux under nitrogen, and 5.76 ml of 3.3 M tert-butyl hydroperoxide (0.019 mol). After the addition was complete, the heating was stopped and the mixture was cooled to room temperature. Thin layer chromatography analysis showed complete conversion of the starting material to a single product. The reaction mixture was treated with about 50 mL of about 5% aqueous sodium sulfite, stirred for 10 minutes and decanted. The organic phase was washed with water, 5% sodium bicarbonate, brine and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford 5.28 g (98%) of the product as a pale yellow oil. NMR anal...

Embodiment 2

[0103] This example illustrates the preparation of epoxyphytol by hydrogenation of 2,3-epoxygeranylgeraniol.

[0104] All the products of Example 6 were dissolved in 50ml ethanol, treated with 0.2g 5% palladium carbon catalyst, and hydrogenated under 1 atmospheric pressure hydrogen for 72 hours (at 40psiH 2 for about 4 hours, 40°C is more convenient). The mixture was filtered (celite) and the solvent stripped to give 5.03 g (95%) of product as a colorless oil which chromatography and NMR spectra showed to be identical to an authentic sample of epoxyphytol prepared by epoxidizing phytol. Example 3

Embodiment 3

[0105] This example illustrates the preparation of phytol / isophytol mixtures from epoxyphytol. A solution of 5.0 g of epoxyphytol (0.016 mol) obtained in Example 7 and 4.72 g of triphenylphosphine (0.018 mol) in 50 ml of toluene was treated with 80 mg of methylrhenium trioxide and stirred at reflux for 2 hours. Thin layer chromatography analysis showed the absence of starting material and the presence of isophytol, phytol and traces of front olefins. The mixture was cooled, filtered through a small pad of silica gel to remove the catalyst, and the solvent was stripped to give 5.0 g of crude product. Silica gel chromatography yielded 0.4 g phytadiene (7.4%) and 3.9 g (83%) of a 3:1 mixture of isophytol and phytol.

[0106] Subsequent tests of the examples were carried out with a small amount of catalyst (20-40 mg), which was removed by washing with aqueous sodium carbonate (yellow hydrolysis product ReO 4 ＝ into the water layer immediately). The crude product of this method...

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Abstract

The invention provides processes for producing phytol, isophytol, and certain phytol derivatives by a method of oxidizing or epoxidizing geranylgeraniol or geranylgeraniol derivatives to form epoxygeranylgeraniol derivatives, reducing or hydrogenating the epoxygeranylgeraniol derivatives to produce epoxyphytol derivatives, and then deoxygenating the epoxyphytol derivatives to produce phytol, isophytol, phytene derivatives, isophytene derivatives, or mixtures thereof. The step of deoxygenating is carried out in the presence of deoxygenation catalysts, including rhenium trioxide compounds. The invention also provides methods for the synthesis of certain novel substituted epoxyphytyl compounds and substituted phytene compounds having removable protecting groups. The produced phytol, isophytol, phytene derivatives, isophytene derivatives, substituted epoxyphytyl compounds and substituted phytene compounds are suitable starting materials for condensation with trimethylhydroquinone derivatives in the presence of Lewis acids to give tocopherol derivatives including alpha-tocopherol, vitamin E.

Description

[0001] Cross-linkages to related applications [0002] This application claims priority to US Provisional Application No. 60 / 091868, filed July 6, 1998, entitled "Process for the Production of Vitamins." field of invention [0003] The present invention generally relates to processes for the preparation of phytol, isophytol, certain phytol derivatives, vitamin E and related tocopherol derivatives including alpha-tocopherol. Background of the invention [0004] Vitamin E (d-α-tocopherol, 1) is an important nutritional supplement for humans and animals, compound 1 is obtained industrially by isolation from various vegetable oils, or by ring methylation of the related natural d-γ-tocopherol 2 Semi-synthetic obtained. A more important source of vitamin E is the fully synthetic method, which yields synthetic vitamin E, d, 1-alpha-tocopherol3. Despite being a mixture of isomers, 3 provides similar biological activity to 1 and is widely used due to its low cost and greater availa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/04C07B61/00C07C43/166C07C69/145C07D301/19C07D303/16C07D311/72C12P9/00
CPCC07D311/72C07D303/16Y02P20/55
Inventor J·A·许尔特
Owner EASTMAN CHEM CO
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