Process for producing aromatic compounds by supercritical...

Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution...

Reexamination Certificate

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C162S079000, C424S093200, C426S052000, C426S422000, C426S542000, C426S592000, C426S597000, C252S398000

Reexamination Certificate

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06331320

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The present invention relates to a process for producing aromatic compounds from a plant material. More particularly, the invention relates to a process for producing aromatic compounds in a short period of time and by a simple procedure involving treatment of a plant material with water which is in a supercritical state or subcritical state.
PRIOR ART
Plant materials are known to contain polymeric compounds, such as lignin and ellagitannin, having various aromatic compounds, such as vanillin, gallic acid, ellagic acid, and protocatechuic acid, as constituent units. Hitherto known methods for obtaining aromatic compounds contained in plant materials have been only extraction methods involving radical decomposition, such as thermal modification (Japanese Patent Public Disclosure (Kokai) No. 59519/97), electron beam irradiation (Japanese Patent Public Disclosure (Kokai) No. 121392/75), and explosive disintegration (Japanese Patent Public Disclosure (Kokai) Nos. 19895/86, 222802/88, 117400/90, 126725/92, and 145027/92).
Many aromatic compounds have characteristic aromas. Vanillin is an aromatic compound used widely as an edible perfume in foods such as ice cream and candies, and as a flavor in luxury products such as liqueur and tobacco. Industrially, vanillin is synthesized by methylating protocatechualdehyde, which is derived from eugenol or salofural, with an alkali and dimethyl sulfate, or by oxidatively treating lignin sulfonic acid contained in sulfite pulp waste liquor. A method of extraction from vanilla beans is also performed, but can obtain only a trace amount of vanillin from a large amount of a raw material. Syringaldehyde, an aromatic compound, is known as an aroma component of sake, but a method for commercial production of this compound has not been known. Gallic acid is utilized as a deoxidizing agent, a developer for photography, a starting material for inks and dyes, an astringent, or a hemostatic.
Various application studies are under way with regard to extraction, purification, synthesis and decomposition using supercritical fluids. For supercritical water, studies on its capacity to detoxify PCB and dioxin (Japanese Patent Public Disclosure (Kokai) No. 327678/97) are being carried out, and its degradation reaction of biomass is also being investigated. Japanese Patent Public Disclosure (Kokai) No. 31000/93 reports a method which selectively hydrolyzes or pyrolyzes natural or synthetic high molecular compounds with the use of supercritical water as a solvent to decompose the polymers into their constituent units or into approximately oligomeric combinations of the constituent units. Examples of this method include formation of glucose from cellulose contained in large amounts in polymeric resources, such as paper, wood and straw, and conversion of lignin-derived specimens into low molecular compounds. Japanese Patent Public Disclosure (Kokai) No. 268166/97 describes a method for producing various amino acids by hydrolyzing proteins with water present in a supercritical state.
However, it has not been known that it is possible to obtain aromatic compounds by treating plant materials with water present in a supercritical state.
SUMMARY OF THE INVENTION
The present invention provides a process for producing aromatic compounds from a plant material in a short period of time and by a simple procedure.
The present invention further provides a process for producing aromatic compounds, which process does not discharge waste generated as squeeze leavings as results from conventional methods such as thermal modification.


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patent: 5043100 (1991-08-01), Chang et al.
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patent: 5258188 (1993-11-01), Barmentlo et al.
Steven B. Hawthorne et al., Extraction of Organic Pollutants from Environmenmtal Solids with Sub- and Supercritical Water. Anal, Chem. vol. 66, pp. 2912-2920, Sep. 1994.
Tina M. Pawlowski et al. Extraction of Thiabandazole and Carbendazim from Foods Using Pressurized Hot (Subcritical) Water for Extraction: A Feasability Study. J. Agric. Food Chem., vol. 46, pp. 3124-3132, Jul. 1998.
Martin, J.P. et al. In Lignin Biodegradation: Microbiology, Chemistry and Potential Applications. vol. 1, Kirk, T.K.et al.(eds), CRC Press, Boca Raton, Fl. pp. 77-101. Proc., Internat'l Seminar, May 9-11, 1978 at US FP:L, Madison, WI, Book Published in 1980.

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