WO2019230803A1 - バガスからのポリフェノール組成物の製造方法 - Google Patents
バガスからのポリフェノール組成物の製造方法 Download PDFInfo
- Publication number
- WO2019230803A1 WO2019230803A1 PCT/JP2019/021310 JP2019021310W WO2019230803A1 WO 2019230803 A1 WO2019230803 A1 WO 2019230803A1 JP 2019021310 W JP2019021310 W JP 2019021310W WO 2019230803 A1 WO2019230803 A1 WO 2019230803A1
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- WIPO (PCT)
- Prior art keywords
- bagasse
- liquid
- synthetic adsorbent
- polyphenol composition
- solution
- Prior art date
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- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 58
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 241000609240 Ambelania acida Species 0.000 title claims abstract description 40
- 239000010905 bagasse Substances 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 36
- 239000003463 adsorbent Substances 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 239000012670 alkaline solution Substances 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000706 filtrate Substances 0.000 claims abstract description 17
- 230000002378 acidificating effect Effects 0.000 claims abstract description 14
- 239000000243 solution Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000012046 mixed solvent Substances 0.000 claims abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 49
- 238000001914 filtration Methods 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 3
- 238000002203 pretreatment Methods 0.000 claims 1
- 238000010828 elution Methods 0.000 description 21
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 16
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 16
- 229940114124 ferulic acid Drugs 0.000 description 16
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 16
- 235000001785 ferulic acid Nutrition 0.000 description 16
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 150000004676 glycans Chemical class 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229920001282 polysaccharide Polymers 0.000 description 6
- 239000005017 polysaccharide Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 244000017020 Ipomoea batatas Species 0.000 description 5
- 235000002678 Ipomoea batatas Nutrition 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 3
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- 229920002488 Hemicellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000011085 pressure filtration Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 229920005610 lignin Chemical group 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 description 1
- 229920002498 Beta-glucan Polymers 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229930002877 anthocyanin Natural products 0.000 description 1
- 235000010208 anthocyanin Nutrition 0.000 description 1
- 239000004410 anthocyanin Substances 0.000 description 1
- 150000004636 anthocyanins Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229930015704 phenylpropanoid Natural products 0.000 description 1
- 150000002995 phenylpropanoid derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L35/00—Food or foodstuffs not provided for in groups A23L5/00 – A23L33/00; Preparation or treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Definitions
- the present invention relates to a method for producing a polyphenol composition from bagasse.
- Patent Document 1 describes a method of subjecting plant material, particularly waste corn, to alkaline boiling and / or enzymatic treatment to recover an aqueous liquid phase containing ferulic acid and polysaccharide, and then recovering ferulic acid. .
- Non-Patent Documents 1 to 3 describe a method of obtaining polyphenols by treating bagasse or the like with an alkaline solution.
- Non-Patent Document 1 discloses that when sugarcane shells are treated with alkali, ester bonds with polysaccharides are hydrolyzed and ferulic acid or p-coumaric acid is liberated.
- Non-Patent Document 2 and Non-Patent Document 3 disclose that coumaric acid is liberated by treating bagasse with an aqueous sodium hydroxide solution as an alkali treatment for extraction of coumaric acid and ferulic acid.
- Patent Literature 2 and Patent Literature 3 describe a method for producing a sugar solution, which includes a step of hydrolyzing cellulose-containing biomass such as bagasse with cellulase derived from filamentous fungi.
- the present invention aims to provide a novel method for producing a polyphenol composition from bagasse.
- the pretreatment liquid generated in the sugar liquid production process contains polyphenols such as coumaric acid and ferulic acid, and further, this pretreatment liquid is treated by a predetermined method. Thus, it was found that the polyphenol composition in the pretreatment liquid can be produced very efficiently.
- the present invention is a method for producing a polyphenol composition from bagasse, wherein bagasse is pretreated using at least one alkaline solution selected from the group consisting of a sodium hydroxide aqueous solution, a potassium hydroxide aqueous solution, and an ammonia aqueous solution.
- a step of obtaining a pretreatment liquid a step of adjusting the pH of the pretreatment liquid to acidity with hydrochloric acid and then filtering, collecting the filtrate, and a column packed with an aromatic synthetic adsorbent
- the temperature of the alkaline solution is preferably 50 to 110 ° C.
- the alkaline solution is preferably a sodium hydroxide aqueous solution.
- concentration of the sodium hydroxide aqueous solution may be 0.1 to 10% by mass.
- the aromatic synthetic adsorbent in the elution step is preferably composed of a styrene-divinylbenzene resin.
- a novel method for producing a polyphenol composition from bagasse can be provided.
- FIG. 2 is a chart obtained by HPLC analysis of the polyphenol composition according to Example 1.
- the polyphenol composition produced in the present invention is a composition containing one or more polyphenols.
- the polyphenol in the present specification is a phenolic compound that can be measured by the foreign-thiocult method. More specifically, the polyphenol may be a phenylpropanoid such as p-coumaric acid or ferulic acid, a flavonoid such as catechin or anthocyanin, and the like.
- bagasse is first pretreated using an alkaline solution to obtain a pretreatment liquid (pretreatment step).
- bagasse is a pomace of sweet potato and typically refers to bagasse discharged during the sugar production process in a sugar factory.
- emitted in the sugar manufacturing process in a sugar factory includes not only the final bagasse which came out of the final pressing machine but the shredded sweet potato which was bitten by the subsequent pressing machine containing a 1st pressing machine.
- bagasse discharged after squeezing sugar juice in a squeezing process in a sugar factory is used.
- emitted from a pressing process differs in the water
- the bagasse may be the bagasse remaining after the sweet potato press discharged at the brown sugar factory. Further, in a small-scale implementation at the laboratory level, bagasse after squeezing sugar liquid from sweet potato may be used.
- the pretreatment using the alkaline solution may be a treatment of bringing the alkaline solution into contact with bagasse in one embodiment.
- Examples of the method of bringing the alkaline solution into contact include a method of sprinkling the alkaline solution over bagasse, a method of immersing bagasse in the alkaline solution, and the like.
- the mixture of bagasse and alkaline solution may be immersed while stirring.
- the alkaline solution may be at least one selected from the group consisting of an aqueous sodium hydroxide solution, an aqueous potassium hydroxide solution, and an aqueous ammonia solution.
- the alkaline solution is preferably an aqueous sodium hydroxide solution from the viewpoint of being inexpensive and used in the food production process.
- the concentration of the alkaline solution may be appropriately set depending on the type of the alkaline solution to be used, but is preferably 0.1% by mass or more, more preferably 0.2% by mass from the viewpoint of shortening the pretreatment time. It is above, More preferably, it is 0.3 mass% or more.
- the concentration of the alkaline solution is preferably 10% by mass or less, more preferably 5% by mass or less, and further preferably 1.0% by mass or less from the viewpoint of improving the extraction efficiency.
- the concentration of the alkaline solution is 0.1 to 10% by mass, 0.1 to 5% by mass, 0.1 to 1.0% by mass, 0.2 to 10% by mass, 0.2 to 5% from the same viewpoint. It may be mass%, 0.2 to 1.0 mass%, 0.3 to 10 mass%, 0.3 to 5 mass%, or 0.3 to 1.0 mass%.
- the temperature (liquid temperature) of the alkaline solution is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, and further preferably 80 ° C. or higher from the viewpoint of shortening the pretreatment time.
- the temperature of the alkaline solution is preferably 110 ° C. or lower, more preferably 105 ° C. or lower, and further preferably 100 ° C. or lower from the viewpoint of preventing polysaccharides from remaining in the pretreatment liquid.
- the temperature of the alkaline solution is 50 to 110 ° C., 50 to 105 ° C., 50 to 100 ° C., 60 to 110 ° C., 60 to 105 ° C., 60 to 100 ° C., 80 to 110 ° C., 80 to 105 ° C. from the same viewpoint. Or 80-100 ° C.
- the addition amount of the alkaline solution may be 50 parts by mass or more, 100 parts by mass or more, or 1000 parts by mass or more with respect to 100 parts by mass of bagasse, and the treatment time in the pretreatment step is the kind of the alkali solution, although it may be appropriately adjusted depending on the temperature and the amount added, it may be, for example, 1 to 5 hours.
- the pH of the pretreatment liquid may be 8 or more, 9 or more, or 13 or less, or 12 or less.
- the insoluble content and the liquid content may be separated after performing the alkali treatment described above.
- the separated liquid can be used as a pretreatment liquid.
- the method for separating the insoluble component and the liquid component may be separation by strainer, filtration, centrifugation, decantation, or the like.
- the pH of the obtained pretreatment solution is adjusted to acidic with hydrochloric acid and then filtered to collect the filtrate (filtration step).
- hydrochloric acid is added to the pretreatment liquid to adjust the pH of the pretreatment liquid to acid.
- concentration of hydrochloric acid may be appropriately set as long as the pH can be adjusted, and may be 0.1 to 35% by mass, for example.
- hydrochloric acid for pH adjustment the produced polyphenol composition can be used in the food industry.
- the pH of the pretreatment liquid after addition of hydrochloric acid is preferably 1.5 or more from the viewpoint of achieving both suppression of polyphenol aggregation and adsorption of the synthetic adsorbent. More preferably, it is 2.0 or more, More preferably, it is 2.5 or more, Preferably it is 4.5 or less, More preferably, it is 4.0 or less, More preferably, it is 3.5 or less is there.
- the pH of the acidic pretreatment liquid is 1.5 to 4.5, 1.5 to 4.0, 1.5 to 3.5, 2.0 to 4.5, 2.0 to 4 from the same viewpoint. 0.0, 2.0 to 3.5, 2.5 to 4.5, 2.5 to 4.0, or 2.5 to 3.5.
- the pH of the acidic pretreatment liquid is 1.5 or more, polyphenols are difficult to agglomerate and precipitate, so even if filtration is performed after pH adjustment, polyphenols are difficult to be removed by filtration.
- the pH of the acidic pretreatment liquid is 4.5 or less, polyphenol can be easily adsorbed to the aromatic synthetic adsorbent in the elution step described later. That is, when the pH of the acidic pretreatment liquid is within the above range, the adsorption to the aromatic synthetic adsorbent can be promoted while suppressing the aggregation and precipitation of polyphenol.
- insoluble components are precipitated in the acidic pretreatment liquid.
- the precipitated insoluble components are removed by filtration. Filtration may be performed by natural filtration, vacuum filtration, pressure filtration, centrifugal filtration, or the like, and preferably by pressure filtration.
- the pressure filtration may be performed by a pressure filter (filter press).
- a filter aid may be added to the acidic pretreatment liquid.
- filter aids include diatomaceous earth, perlite, and cellulose.
- the content of the filter aid may be 0.2 to 2.0 mass% based on the total amount of the acidic pretreatment liquid.
- the obtained filtrate is passed through a column filled with an aromatic synthetic adsorbent.
- an aromatic synthetic adsorbent By eluting the component adsorbed on the aromatic synthetic adsorbent with a mixed solvent of ethanol and water to obtain an elution fraction, a polyphenol composition can be produced (elution step).
- the aromatic synthetic adsorbent is a synthetic adsorbent made of an aromatic resin from the viewpoint of efficiently adsorbing the polyphenol composition contained in the filtrate.
- an aromatic resin a styrene-divinylbenzene aromatic resin (styrene-divinylbenzene resin) is preferable.
- styrene-divinylbenzene aromatic resins include aromatic resins having hydrophobic substituents, non-substituted aromatic resins, and aromatic resins that have undergone special treatment on non-substituted types. Porous resin and the like.
- the styrene-divinylbenzene aromatic resin is preferably an unsubstituted aromatic resin, or an aromatic resin obtained by subjecting the unsubstituted radical type to a special treatment with a high specific surface area.
- An aromatic resin that has been specially treated to increase the specific surface area is more preferable.
- the specific surface area of the aromatic synthetic adsorbent is preferably 500 m 2 / g or more, more preferably 700 m 2 / g or more, as a dry mass.
- the specific surface area of the aromatic synthetic adsorbent can be calculated by applying the measured value of the gas adsorption method to the BET equation.
- the most frequent pore diameter (moderate pore diameter) of the aromatic synthetic adsorbent is preferably 600 mm or less, more preferably 300 mm or less, and still more preferably 200 mm from the viewpoint of high separability and high adsorptivity. It is as follows. The most frequent pore diameter can be measured by a gas adsorption method.
- Such synthetic adsorbents are commercially available.
- Diaion (trademark) HP-10, HP-20, HP-21, HP-30, HP-40, HP-50 (above, unsubstituted fragrance Family resins, all trade names, manufactured by Mitsubishi Chemical Corporation); SP-825, SP-800, SP-850, SP-875, SP-70, SP-700 (above, special treatment for unsubstituted type SP-900 (aromatic resin, trade name, manufactured by Mitsubishi Chemical Corporation); Amberlite (trademark) XAD-2, XAD-4 XAD-16, XAD-18, XAD-2000 (above, aromatic resins, all trade names, manufactured by Organo Corporation); Diaion (trademark) SP-205, SP-206, SP-207 (above, Sparse HP-2MG, EX-0021 (above, aromatic resins having hydrophobic substituents, both trade names, Mitsubishi Chemical Co., Ltd.) Etc.).
- Diaion (trademark) SP-850 is preferable.
- the amount of the aromatic synthetic adsorbent packed in the column can be appropriately determined depending on the size of the column, the type of the synthetic adsorbent, and the like.
- the temperature of the filtrate may be 25 to 45 ° C.
- the flow rate and flow rate when the filtrate is passed through the column can be appropriately determined depending on the type of the aromatic synthetic adsorbent and the like.
- the components adsorbed on the column are eluted with a mixed solvent of ethanol and water after completion of the flow.
- the mixing volume ratio (ethanol / water) of the mixed solvent may be 50/50 to 99/1, and is preferably in the range of 50/50 to 70/30 from the viewpoint of improving elution efficiency.
- the elution rate can be appropriately determined depending on the size of the column, the type of the aromatic synthetic adsorbent, and the like.
- a bagasse-derived polyphenol composition can be produced by obtaining an elution fraction in the elution step.
- a step (concentration step) of concentrating the elution fraction (polyphenol composition) may be further provided as necessary.
- concentration step for example, concentration may be performed 5 to 20 times using a centrifugal thin film vacuum evaporator. Thereby, the concentrate containing a polyphenol composition can be obtained.
- the polyphenol composition that can be produced by the method of the present embodiment may mainly contain coumaric acid and ferulic acid as the polyphenol. Whether the polyphenol composition contains polyphenol can be confirmed by measurement by the foreign-thiocult method. The composition of the polyphenol composition can be confirmed by qualitative and quantitative analysis of the obtained polyphenol composition by high performance liquid chromatography (HPLC).
- HPLC high performance liquid chromatography
- the polyphenol composition obtained by the method of the present embodiment is particularly suitable as a food material because it is obtained by using an aromatic synthetic adsorbent in the elution step and eluting using a mixed solvent of ethanol and water. Can be used.
- the method of the present embodiment is a new method different from the conventional method for producing a polyphenol composition from bagasse, and in particular, a polyphenol composition from a pretreatment liquid (waste liquid) generated in a step of producing a sugar liquid from bagasse. This is a useful method in that it can be produced.
- the method of Patent Document 1 described above is a method of increasing the purity of ferulic acid and recovering it as crystals in order to use ferulic acid as a raw material for vanillin.
- the method is different from the method of the present embodiment in that a processing solution in which ferulic acid and polysaccharides are mixed is obtained using an extruder and a grinder-homogenizer.
- Non-Patent Documents 1 to 3 are methods in which plant materials are treated for a long time with a relatively low-temperature alkaline solution. This is more effective when the alkaline treatment is performed under mild conditions. This is because monophenols that are ester-bonded to saccharides are easily released, and the purity of coumaric acid and ferulic acid is increased.
- these methods are used for the waste liquid generated in the saccharification process, the processing time becomes long, and the balance between the time required for the saccharification process for obtaining the sugar liquid from bagasse and the time required for the treatment of the waste liquid. You may not be able to remove.
- a polyphenol composition can be efficiently produced from the waste liquid produced in the saccharification step while giving priority to the saccharification step.
- the pretreatment liquid that has been conventionally discarded can be used effectively without being discarded.
- the disposal cost of the pretreatment liquid can be reduced.
- the polyphenol composition that can be produced by the method of the present embodiment can also be used as a raw material for isolating and purifying polyphenols contained in the polyphenol composition in a high yield.
- the method for isolating and purifying the polyphenols from the polyphenol composition may be a known method. That is, the method of this embodiment can also be said to be a method for producing a raw material capable of isolating and purifying polyphenols such as ferulic acid and p-coumaric acid.
- Polyphenols isolated and purified from the polyphenol composition can also be suitably used as a food material in the same manner as the polyphenol composition described above.
- Example 1 Production test of polyphenol composition
- Example 1> (Pretreatment process) To a stainless steel pan, add 3.2 kg of bagasse (water content 50% by mass) and 90 L of 0.5% (w / w) aqueous sodium hydroxide at 90 ° C, and mix for 2 hours. A pretreatment was performed. The pre-treated mixed liquid was separated into an insoluble part and a liquid part to obtain about 20 L of the liquid part. This was repeated twice to obtain 40 L of liquid (pretreatment liquid).
- Table 1 shows the conditions of the concentration gradient (gradient) in the analysis by HPLC.
- Retention time Retention Time: RT
- Example 2 Examination of aromatic synthetic adsorbent
- 20 L of filtrate by a filter press was obtained from about 3 kg of bagasse (water content 50 mass%).
- Diaion SP-850 manufactured by Mitsubishi Chemical Corporation, Example 2
- Amberlite XAD-4 manufactured by Organo Corporation, Example 3
- Amberlite Amberlite are used as aromatic synthetic adsorbents.
- XAD-18 manufactured by Organo Corporation, Example 4 was used.
- Table 2 shows the solid concentration (mass%, based on the total amount of the eluted fraction) and the polyphenol concentration (mass%, based on the total amount of the eluted fraction) according to Examples 2 to 4.
- each of the total polyphenol, coumaric acid, and ferulic acid contained in the passing liquid after passing through the column liquid fraction not adsorbed on the synthetic adsorbent
- elution fraction liquid fraction adsorbed on the synthetic adsorbent
- Each ratio (recovery rate) was determined.
- the recovered amount of total polyphenol was measured by the foreign-thiocult method, and the recovered amounts of coumaric acid and ferulic acid were measured by HPLC. The results are shown in Table 3.
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Abstract
Description
<実施例1>
(前処理工程)
ステンレス製寸胴鍋に、サトウキビの搾りかすであるバガス3.2kg(含水率50質量%)及び90℃の0.5%(w/w)水酸化ナトリウム水溶液20Lを添加し、2時間混合することによって、前処理を行った。前処理後の混合液を不溶分と液分に分離して、液分を約20L得た。これを2回繰り返し、40Lの液分(前処理液)を得た。
上記の前処理液全量に対して、35%(w/w)塩酸を475mL添加し、pHを3.0に調整した。これを酸性前処理液とした。酸性前処理液に、ろ過助剤として珪藻土を395g(前処理液全量基準で1%(w/w)になるように)添加し、フィルタープレスでろ過することにより、不溶性成分を除去し、ろ液を38kg得た。
ろ過工程により得られたろ液を、芳香族系合成吸着剤(ダイヤイオンSP-850、三菱ケミカル株式会社製)383mLを充填したカラム(カラム容量:1L)に、流速7.6L/h(SV=20)の条件で通液した。その後、合成吸着剤の体積の10倍量の水で洗浄し、60%(v/v)エタノール水溶液をSV=2で766g通液して溶出し、溶出画分を得た。溶出画分を、48%(w/w)水酸化ナトリウム水溶液を用いてpH6.7に調整し、ロータリーエバポレーターにより10倍の濃度に濃縮して、ポリフェノール組成物を77g得た。
得られたポリフェノール組成物について、高速液体クロマトグラフィー(HPLC、Agilent 1260 Infinity LC、アジレント・テクノロジー株式会社製)による分析を行い、組成を確認した。分析条件は次のとおりである。
サンプル注入量:30μL
溶離液流速:0.6mL/min
溶離液:水(6%酢酸)(溶離液A)、メタノール(6%酢酸)(溶離液B)
カラム:LiChroCART(長さ150mm×内径4.6mm、粒子径5μm、メルク株式会社)
カラム温度:60℃
UV-VIS検出器設定波長:260nm
<実施例2~4>
実施例1と同様の前処理工程及びろ過工程に従って、バガス約3kg(含水率50質量%)からフィルタープレスによるろ液20Lを得た。溶出工程においては、芳香族系合成吸着剤として、ダイヤイオンSP-850(三菱ケミカル株式会社製、実施例2)、アンバーライトXAD-4(株式会社オルガノ製、実施例3)、及び、アンバーライトXAD-18(株式会社オルガノ製、実施例4)をそれぞれ用いた。各吸着剤50mLをそれぞれ充填したカラム(カラム容量100mL)を用意し、流速1000mL/h(SV=20)の条件でろ液を5Lずつ通液した。その後、各カラムにおいて、合成吸着剤の体積の10倍量の水で洗浄し、60%(v/v)エタノール水溶液をSV=2で100mL通液して溶出し、溶出画分を得た。実施例2~4に係る溶出画分の固形分濃度(質量%、溶出画分全量基準)及びポリフェノール濃度(質量%、溶出画分全量基準)を、表2に示す。
<実施例5~7、比較例1>
(前処理工程、ろ過工程)
実施例1と同様の前処理工程に従って、バガス約3kg(含水率50質量%)から前処理液20Lを得た。この液分を4つに分け、そのうち3つを、35%(w/w)塩酸により、pH6(実施例5)、pH5.5(実施例6)、pH3(実施例7)にそれぞれ調整した。また、4つに分けた前処理液のうち1つは、pHを調整しなかった(比較例1)。pHを調整していない比較例1の前処理液のpHは10.8であった。これら4種類の前処理液を、実施例1と同様の方法によってろ過した。
ろ過工程により得られたろ液を、芳香族系合成吸着剤(ダイヤイオンSP-850、三菱ケミカル株式会社製)383mLを充填したカラム(カラム容量:1L)に、流速SV=10、通液量BV=50の条件で通液した。その後、合成吸着剤の体積の10倍量の水で洗浄し、60%(v/v)エタノール水溶液をSV=2、BV=2で通液して溶出した。カラム通液後の通過液(合成吸着剤に吸着しなかった液分)、及び、溶出画分(合成吸着剤に吸着した液分)に含まれる総ポリフェノール、クマル酸、及びフェルラ酸のそれぞれの回収量(g)を測定し、溶出前のろ液中に含まれるポリフェノール量(g)に対する、通過液又は溶出画分に含まれる総ポリフェノール(ポリフェノール組成物)、クマル酸、及びフェルラ酸の質量比(回収率)をそれぞれ求めた。なお、総ポリフェノールの回収量はフォーリン-チオカルト法により測定し、クマル酸及びフェルラ酸の回収量は、HPLCにより測定した。結果を表3に示す。
Claims (5)
- バガスからのポリフェノール組成物の製造方法であって、
水酸化ナトリウム水溶液、水酸化カリウム水溶液、及びアンモニア水溶液からなる群より選ばれる少なくとも1種のアルカリ溶液を用いてバガスを前処理し、前処理液を得る工程と、
前記前処理液のpHを塩酸で酸性に調整してからろ過し、ろ液を回収する工程と、
前記ろ液を、芳香族系合成吸着剤が充填されたカラムに通液し、前記芳香族系合成吸着剤に吸着した成分をエタノール及び水の混合溶媒で溶出して溶出画分をポリフェノール組成物として得る工程と、を備える、製造方法。 - 前記アルカリ溶液の温度は50~110℃である、請求項1に記載の製造方法。
- 前記アルカリ溶液は水酸化ナトリウム水溶液である、請求項1又は2に記載の製造方法。
- 前記水酸化ナトリウム水溶液の濃度は、0.1~10質量%である、請求項3に記載の製造方法。
- 前記芳香族系合成吸着剤はスチレン-ジビニルベンゼン系樹脂からなる、請求項1~4のいずれか一項に記載の製造方法。
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