WO2021060334A1 - Procédé de production d'acétoïne - Google Patents

Procédé de production d'acétoïne Download PDF

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Publication number
WO2021060334A1
WO2021060334A1 PCT/JP2020/035929 JP2020035929W WO2021060334A1 WO 2021060334 A1 WO2021060334 A1 WO 2021060334A1 JP 2020035929 W JP2020035929 W JP 2020035929W WO 2021060334 A1 WO2021060334 A1 WO 2021060334A1
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acetoin
membrane
nanofiltration membrane
polyamide
producing
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PCT/JP2020/035929
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English (en)
Japanese (ja)
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塚本大治郎
河村健司
伊藤正照
山田勝成
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東レ株式会社
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Priority to JP2020570996A priority Critical patent/JPWO2021060334A1/ja
Publication of WO2021060334A1 publication Critical patent/WO2021060334A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/786—Separation; Purification; Stabilisation; Use of additives by membrane separation process, e.g. pervaporation, perstraction, reverse osmosis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/58—Multistep processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/56—Polyamides, e.g. polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups

Definitions

  • the present invention relates to a method for producing acetoin by separating acetoin from an acetoin-containing solution. More specifically, the present invention relates to a method for producing acetoin, which comprises a step of removing inorganic salts, sugars, proteins, catalyst components and the like remaining in the acetoin-containing solution by a nanofiltration membrane.
  • Acetoin (3-hydroxy-2-butanone) is a compound with a yogurt and butter-like scent, and is used as a food additive and a raw material for cosmetics.
  • Diacetyl (2,3-butandione) which is a compound similar to acetoin, is used not only as a food additive but also in pharmaceutical production.
  • the mainstream method for producing acetoin is by chemical synthesis, but there are problems such as a decrease in crude oil resources and soaring prices, and since acetoin is a metabolite of microorganisms, biomass is used as a raw material and microorganisms are used. An alternative to the manufacturing method is expected.
  • acetoin As a method for purifying acetoin in the case of producing acetoin using biomass as a raw material using microorganisms or the like, it is considered that a general method for isolating and purifying an ordinary water-soluble neutral substance can be applied. After removing the bacterial cells from the acetoin culture solution, impurities are removed from the culture supernatant by treatment with activated charcoal, ion exchange resin, microfiltration membrane, ultrafiltration membrane, nanofiltration membrane, back-penetration membrane, etc. It is considered that acetoin can be isolated and purified by methods such as distillation, gas stripping, permeation vaporization, extraction with an organic solvent, and recrystallization (Patent Documents 1 to 5). However, since the development of a method for producing acetoin using biomass as a raw material has just begun, a method for purifying acetoin from an acetoin culture solution has not been technically established.
  • an object of the present invention is to solve the above-mentioned problems in purifying acetoin and to find a method for separating and recovering acetoin with high purity and low cost.
  • the present inventor focused on the purification of acetoin using a nanofiltration membrane or a reverse osmosis membrane.
  • the permeability of nanofiltration membranes and reverse osmosis membranes of substances cannot be predicted simply by the relationship between the molecular weight of substances and the fractional molecular weights of these separation membranes, and the permeability of nanofiltration membranes and reverse osmosis membranes of acetoin.
  • the present inventor has found a process capable of obtaining high-purity and high-concentration acetoin by using these separation membranes, and has completed the present invention.
  • the present invention is composed of the following (1) to (7).
  • a method for producing acetoin which comprises step A of filtering the acetoin-containing solution through a nanofiltration membrane and recovering the acetoin-containing solution from the permeation side.
  • R represents -H or -CH 3
  • n represents an integer from 0 to 3.
  • step B The method for producing acetoin according to any one of (1) to (4), which comprises step B in which the acetoin-containing solution obtained in step A is passed through a reverse osmosis membrane to increase the acetoin concentration.
  • the permeate recovered from the step A or the concentrated solution recovered from the step B is further subjected to a step C of distilling at 25 ° C. or higher and 200 ° C. or lower under a pressure of 1 Pa or more and atmospheric pressure or less.
  • An acetoin composition derived from an acetoin-containing microbial culture solution and having an acetoin weight purity of 80% or more.
  • metal catalysts, inorganic salts, and sugars present in a chemical synthesis reaction solution containing acetoin or a fermentation culture solution can be removed by a simple operation to improve the recovery rate and reduce the cost, so that acetoin can be highly purified. It can be manufactured at low cost.
  • the acetoin production method of the present invention is a method for producing acetoin by separating acetoin from an acetoin-containing solution, and is a step of passing the acetoin-containing solution through a nanofiltration membrane to remove a metal catalyst, an inorganic salt, a saccharide, or the like.
  • the present invention relates to a method for producing acetoin, including.
  • the acetoin that can be produced in the present invention is an organic compound also called 3-hydroxy-2-butanone, acetylmethylcarbinol, or dimethyl kettle.
  • the method for producing the acetin-containing solution used in the present invention is not particularly limited as long as it is a method known to those skilled in the art, and when a chemical synthesis method is used, a method for synthesizing by partial reduction of diacetyl or double addition reaction of acetaldehyde. and so on.
  • acetoin can be produced by culturing a microorganism capable of producing acetoin in the presence of carbon sources such as sugars, cellulose, hemicellulose, lignin, and decomposition products thereof.
  • the microorganism having an acetoin-producing ability may be one having an ability to produce acetoin from the beginning, or one having a production ability given by breeding, mutation treatment, gene recombination treatment, or the like.
  • the type of bacterium is not particularly limited, but is limited to coryneform bacteria, Escherichia coli, Bacillus bacterium, Geobacillus bacterium, Lactobacillus bacterium, Lactococcus genus bacterium, Staphylococcus. ) Bacteria, Klebsiella bacteria, Streptococcus bacteria, Zymomonas bacteria, filamentous fungi, yeasts and the like.
  • the preferred method for producing the acetoin-containing solution used in the present invention is a fermentation culture method for microorganisms, in which case the fermentation culture solution containing acetoin itself can be used as an acetoin-containing solution to be applied to a nanofilter membrane.
  • the nanofiltration membrane used in the present invention is also called a nanofiltration membrane or an NF membrane, and is a membrane generally defined as "a membrane that allows monovalent ions to permeate and blocks divalent ions". .. It is a membrane that is considered to have microvoids of several nanometers, and is mainly used to block fine particles, molecules, ions, salts, etc. in water.
  • passing through the nanofiltration membrane means that the acetoin-containing solution is filtered through the nanofiltration membrane, impurities other than acetoin are removed to the non-permeate side, and the acetoin-containing solution is recovered from the permeate side. Means.
  • cellulose acetate-based polymers polyamides, polyesters, polyimides, vinyl polymers such as polyvinyl alcohol, and polymer materials such as polysulfone are known as materials for nanofilter membranes, and can be used in the present invention.
  • a nanofiltration membrane having a polyamide as a functional layer is preferably used because of its high purification effect.
  • the functional layer may be a film containing a plurality of other film materials.
  • the membrane structure is formed on an asymmetric membrane having a dense layer on at least one surface of the membrane and having fine pores having a gradually larger pore diameter from the dense layer toward the inside of the membrane or the other surface, or on the dense layer of the asymmetric membrane.
  • a composite membrane for example, a composite membrane described in Japanese Patent Application Laid-Open No. 62-201606 in which a nanofiltration membrane made of a functional layer of polyamide is formed on a support membrane using polysulfone as a membrane material can be used.
  • the nanofiltration membrane having a polyamide functional layer preferably used in the present invention is preferably a composite membrane having high pressure resistance, high water permeability, and high solute removal performance. Further, in order to maintain durability against operating pressure, high water permeability, and blocking performance, a structure in which polyamide is used as a functional layer and the polyamide is held by a support made of a porous film or a non-woven fabric is preferable.
  • preferable carboxylic acid components of the monomer constituting polyamide include, for example, trimesic acid, benzophenone tetracarboxylic acid, trimellitic acid, pyrrometic acid, isophthalic acid, terephthalic acid, and naphthalene.
  • Aromatic carboxylic acids such as dicarboxylic acid, diphenylcarboxylic acid, and pyridinecarboxylic acid can be mentioned, but trimesic acid, isophthalic acid, terephthalic acid, or a mixture thereof is more preferable in consideration of solubility in a film-forming solvent.
  • Preferred amine components of the monomer constituting the polyamide include m-phenylenediamine, p-phenylenediamine, benzidine, methylenebisdianiline, 4,4'-diaminobiphenyl ether, dianisidine, 3,3', 4-.
  • Triaminobiphenyl ether 3,3', 4,4'-tetraaminobiphenyl ether, 3,3'-dioxybenzidine, 1,8-naphthalenediamine, m (p) -monomethylphenylenediamine, 3,3'- Monomethylamino-4,4'-diaminobiphenyl ether, 4,N, N'-(4-aminobenzoyl) -p (m) -phenylenediamine-2,2'-bis (4-aminophenylbenzoimidazole), 2 , 2'-bis (4-aminophenylbenzoxazole), 2,2'-bis (4-aminophenylbenzothiazole) and other primary diamines with aromatic rings, piperazine, piperidine or derivatives thereof and the like.
  • a nanofiltration membrane having a crosslinked polyamide containing piperazine or piperidine as a monomer as a functional layer is preferably used because it has heat resistance and chemical resistance in addition to pressure resistance and durability.
  • a nanofiltration membrane containing the crosslinked piperazine polyamide or the crosslinked piperazine polyamide as a main component is more preferable, and the crosslinked piperazine polyamide or the crosslinked piperazine polyamide is a main component and contains the constituent component represented by the chemical formula 1.
  • nanofiltration membrane containing the crosslinked piperazine polyamide as a main component and the polyamide containing the constituent component represented by the chemical formula (1) as a functional layer examples include those described in JP-A-62-201606. Specific examples thereof include UTC60, which is a crosslinked piperazine polyamide-based nanofiltration membrane manufactured by Toray Industries, Inc.
  • the nanofiltration membrane is generally used as a spiral type membrane element, but the nanofiltration membrane used in the present invention can also be preferably used as a spiral type membrane element.
  • a preferable nanofiltration membrane for example, UTC60 manufactured by Toray Industries, Inc., which contains a crosslinked piperazine polyamide as a main component and a polyamide containing a constituent component represented by the chemical formula (1) as a functional layer, was used.
  • the company's nanofilter modules SU-210, SU-220, SU-600, and SU-610 can also be used.
  • the acetoin-containing solution may be filtered by a nanofiltration membrane under pressure. If the filtration pressure is lower than 0.1 MPa, the membrane permeation rate decreases, and if it is higher than 8 MPa, it affects the damage to the membrane. Therefore, it is preferably used in the range of 0.1 MPa or more and 8 MPa or less, but 0.5 MPa or more and 7 MPa. When used below, it is more preferable to use it at 1 MPa or more and 6 MPa or less because it has a high membrane permeation flux and can efficiently permeate acetoin and is less likely to affect the damage to the membrane. preferable.
  • the filtration of the acetoin-containing solution with the nanofiltration membrane can improve the recovery rate of acetoin by returning the non-permeated solution to raw water and filtering repeatedly.
  • the recovery rate of acetoin can be calculated by Equation 1 by measuring the total amount of acetoin before nanofiltration and the total amount of acetoin permeated through the nanofiltration membrane.
  • Acetoin recovery rate (%) (total amount of acetoin permeated through nanofiltration membrane / total amount of acetoin before nanofiltration) x 100 ... (Equation 1).
  • the membrane separation performance of the nanofiltration membrane used in the present invention is such that the salt removal rate is 45% or more when an aqueous sodium chloride solution (500 mg / L) adjusted to a temperature of 25 ° C. and a pH of 6.5 is evaluated at a filtration pressure of 0.75 MPa. Is preferably used.
  • the salt removal rate referred to here can be calculated by Equation 2 by measuring the permeate salt concentration of the sodium chloride aqueous solution.
  • Salt removal rate 100 x ⁇ 1- (salt concentration in permeate / salt concentration in feed water) ⁇ ... (Equation 2).
  • the membrane permeation flux (m 3 / (m 2 days)) of the sodium chloride aqueous solution (500 mg / L) is 0.3 or more at a filtration pressure of 0.3 MPa. Is preferably used.
  • the membrane permeation flux can be calculated by Equation 3 by measuring the permeated liquid amount, the time at which the permeated liquid amount is sampled, and the membrane area.
  • the impurities separated from the acetoin-containing solution to the non-permeate side by the nanofiltration membrane include inorganic substances such as calcium, sodium, sulfuric acid, nitric acid and phosphoric acid, glucose, fructose, xylose, sucrose, galactose and starch. Examples thereof include sugars and proteins, and even a mixture thereof is preferably separated.
  • the nanofiltration membrane permeability of acetoin in the present invention can be evaluated by calculating the acetoin transmittance.
  • the transmittance of acetoin is contained in the acetoin concentration (raw acetoin concentration) and the permeate (acetoin solution) contained in raw water (solution containing acetoin) by analysis typified by high-speed liquid chromatography and gas chromatography. It can be calculated by Equation 4 by measuring the acetoin concentration (permeate acetoin concentration).
  • Acetine transmittance (%) (permeate acetoin concentration / raw water acetoin concentration) x 100 ... (Equation 4).
  • the nanofiltration membrane permeate is preferably concentrated when the concentration of the target substance is low.
  • a method for concentrating the nanofiltration membrane permeate a method for removing water using a general concentrator typified by an evaporator or a zeolite membrane can be applied in the present invention, but the heat capacity of water is higher than that of an organic solvent. Because it is much larger, the energy and time required for enrichment is enormous.
  • concentration by a reverse osmosis membrane is superior to concentration by an evaporator from the viewpoint of energy cost reduction, and is preferably applied in the present invention.
  • the reverse osmosis membrane in the present invention is a filtration membrane that removes ions and low molecular weight molecules by using a pressure difference equal to or higher than the osmotic pressure of the water to be treated as a driving force.
  • a membrane obtained by polycondensing a polyfunctional acid halide and providing a polyamide separation functional layer on a microporous support membrane can be adopted.
  • an aqueous solution of a compound having at least one reactive group that reacts with an acid halide group is coated on the surface of the polyamide separation functional layer and remains on the surface of the separation functional layer.
  • a low fouling back-penetration film mainly for sewage treatment in which a covalent bond is formed between the acid halide group and the reactive group is also preferably adopted. Since most of the divalent ions can be removed in the step of filtering through the nanofiltration membrane of the present invention, stable membrane concentration can be performed without the formation of scale on the reverse osmosis membrane surface.
  • passing through the reverse osmosis membrane means that the acetoin-containing solution that has permeated the nanofiltration membrane is concentrated through the reverse osmosis membrane, and the solution containing acetoin on the concentrated solution side (non-permeating solution side) is recovered. Means to do.
  • a composite membrane having a cellulose acetate-based polymer as a functional layer (hereinafter, also referred to as a cellulose acetate-based reverse osmosis membrane) or a composite membrane having a polyamide as a functional layer (hereinafter, referred to as a functional layer).
  • a functional layer a composite membrane having a polyamide as a functional layer
  • a polyamide-based reverse osmosis membrane examples of the cellulose acetate-based polymer include those using organic acid esters of cellulose such as cellulose acetate, cellulose diacetate, cellulose triacetate, cellulose propionate, and cellulose butyrate alone or a mixture thereof, and mixed esters. Be done.
  • polyamide examples include linear polymers or crosslinked polymers using aliphatic and / or aromatic diamines as monomers.
  • the membrane morphology an appropriate morphology such as a flat membrane type, a spiral type, and a hollow fiber type can be used.
  • reverse osmosis membrane used in the present invention include, for example, low-pressure type SU-710, SU-720, SU-720F, and SU-710L which are polyamide-based reverse osmosis membrane modules manufactured by Toray Industries, Inc.
  • SU-720L, SU-720LF, SU-720R, SU-710P, SU-720P, high-pressure type SU-810, SU-820, SU-820L, SU-820FA which includes UTC70 as a reverse osmosis membrane Cellulose acetate reverse osmosis membrane SC-L100R, SC-L200R, SC-1100, SC-1200, SC-2100, SC-2200, SC-3100, SC-3200, SC-8100, SC-8200, Nitto Denko Co., Ltd.
  • the nanofiltration membrane permeate is filtered by a reverse osmosis membrane under pressure. If the filtration pressure is lower than 1 MPa, the membrane permeation rate decreases, and if it is higher than 8 MPa, it affects the damage to the membrane. Therefore, it is preferably in the range of 1 MPa or more and 8 MPa or less. Further, when the filtration pressure is in the range of 1 MPa or more and 7 MPa or less, the membrane permeation flux is high, so that the acetoin solution can be efficiently concentrated. Most preferably, it is in the range of 2 MPa or more and 6 MPa or less because it is unlikely to affect the damage of the film.
  • high-purity acetoin can be obtained by subjecting the nanofiltration membrane permeate to the step C of distillation.
  • the distillation step is preferably carried out under a reduced pressure of 1 Pa or more and atmospheric pressure (normal pressure, about 101 kPa) or less, and more preferably 100 Pa or more and 15 kPa or less.
  • the distillation temperature is preferably 20 ° C. or higher and 200 ° C. or lower, and more preferably 50 ° C. or higher and 150 ° C. or lower.
  • the present invention can increase the purity of acetoin in an acetoin composition derived from an acetoin-containing microbial culture solution.
  • an acetoin composition having a weight purity of 80% or more, preferably 90% or more, more preferably 95% or more can be obtained from a microbial culture solution containing acetoin.
  • a high-purity acetoin composition has been produced by chemical synthesis using crude oil as a raw material, but according to the present invention, a high-purity acetoin composition can also be produced from an acetoin-containing microbial culture solution obtained from a biomass raw material. become able to.
  • the high-purity acetoin composition derived from a biomass raw material is suitable for food additive applications and cosmetic applications from the viewpoint of safety.
  • GC analysis conditions GC equipment: GC2010 plus (manufactured by Shimadzu Corporation) Column: Rt- ⁇ -DEX, length 30 m, inner diameter 0.32 mm (manufactured by RESTEK) Carrier gas: helium, constant linear velocity (35.0 cm / sec) Vaporization chamber temperature: 250 ° C Detector temperature: 250 ° C Column oven temperature: constant at 75 ° C (18 minutes) Detector: FID.
  • Example 1 Purification of acetoin from a model culture solution using a nanofiltration membrane 200 L of the acetoin model culture solution prepared in Reference Example 1 was injected into the raw water tank 1 of the membrane filtration device shown in FIG.
  • a crosslinked piperazine polyamide-based nanofiltration membrane “UTC60” nanofiltration membrane 1; manufactured by Toray Co., Ltd.
  • the pressure of the high pressure pump 3 was adjusted to 2 MPa at 10 ° C., and the permeate 4 at each pressure was recovered.
  • the acetoin concentration contained in the raw water tank 1 and the permeate 4 was analyzed by GC, and the acetoin transmittance was calculated. The results are shown in Table 2.
  • 10 L of permeate was recovered, then 10 L of distilled water was added, and the permeate was recovered again 7 times. As a result, acetoin was recovered. The recovery rate was 77%.
  • 100 L of the acetoin-containing solution obtained from the permeation side of the nanofiltration membrane was placed in the raw water tank 1 of the membrane filtration apparatus shown in FIG.
  • a 90 ⁇ reverse osmosis film of reference numeral 7 in FIG. 2 a polyamide reverse osmosis film (UTC-70, manufactured by Toray Co., Ltd.) is attached to a stainless steel (SUS316) cell, the pressure of the high pressure pump 3 is 5 MPa, and the raw water temperature is 20. The temperature was adjusted to ° C. and membrane filtration was performed to remove 90 L of reverse osmosis membrane permeated water 4. The permeated water did not contain acetoin.
  • Example 2 Acetin was purified in the same manner as in Example 1 except that the cellulose acetate-based nanofiltration membrane "GEsepa” (nanofiltration membrane 2; manufactured by GE Osmonics) was used instead of the crosslinked piperazine polyamide-based nanofiltration membrane "UTC60". .. The results are shown in Tables 2 and 3.
  • GEsepa nanofiltration membrane 2; manufactured by GE Osmonics
  • Example 1 Acetoin was purified in the same manner as in Example 1 except that the nanofiltration membrane treatment was not performed. At this time, not only clogging occurred when concentrating with the reverse osmosis membrane, but also many precipitates were generated when concentrating with the rotary evaporator. In the vacuum distillation, it took more time to distill acetoin as compared with Example 1.
  • 1,3-propanediol had a membrane permeability of 35% in the nanofiltration membrane 1 which was lower than that of acetoin. That is, although the molecular weight of 1,3-propanediol and the acetoin shown in Example 1 is smaller than that of 1,3-propanediol, the nanofiltration membrane permeability of acetoin is significantly higher than that of acetoin. It was shown that the compound is more suitable for purification of nanofiltration membranes.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nanotechnology (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

Dans la présente invention, de l'acétoïne de haute pureté peut être séparée et récupérée à faible coût, au moyen d'une étape A dans laquelle une solution contenant de l'acétoïne est filtrée à travers une membrane de nanofiltration, et la solution contenant de l'acétoïne est récupérée à partir du côté de perméation de la membrane.
PCT/JP2020/035929 2019-09-27 2020-09-24 Procédé de production d'acétoïne WO2021060334A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023198993A1 (fr) 2022-04-15 2023-10-19 Lesaffre Et Compagnie Procédé d'obtention d'acétoïne

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0253091A2 (fr) * 1986-07-15 1988-01-20 Hüls Aktiengesellschaft Procédé de séparation d'alcools à bas poids moléculaires de solution aqueuse
JPH024401A (ja) * 1988-01-14 1990-01-09 Huels Ag 水溶液から有価物を分離する方法
JP2013518081A (ja) * 2010-01-29 2013-05-20 ワッカー ケミー アクチエンゲゼルシャフト 再生可能な原料から１〜３個の炭素原子を有するカルボン酸を製造する方法
US20150329927A1 (en) * 2014-05-17 2015-11-19 Sweetwater Energy, Inc. Sugar Separation and Purification Through Filtration
JP2015227298A (ja) * 2014-05-30 2015-12-17 三菱化学株式会社 ２，３−ブタンジオールの製造方法
CN109852478A (zh) * 2019-01-30 2019-06-07 四川中烟工业有限责任公司 一种从白酒丢糟中提取原味酒香风味物质的方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0253091A2 (fr) * 1986-07-15 1988-01-20 Hüls Aktiengesellschaft Procédé de séparation d'alcools à bas poids moléculaires de solution aqueuse
JPH024401A (ja) * 1988-01-14 1990-01-09 Huels Ag 水溶液から有価物を分離する方法
JP2013518081A (ja) * 2010-01-29 2013-05-20 ワッカー ケミー アクチエンゲゼルシャフト 再生可能な原料から１〜３個の炭素原子を有するカルボン酸を製造する方法
US20150329927A1 (en) * 2014-05-17 2015-11-19 Sweetwater Energy, Inc. Sugar Separation and Purification Through Filtration
JP2015227298A (ja) * 2014-05-30 2015-12-17 三菱化学株式会社 ２，３−ブタンジオールの製造方法
CN109852478A (zh) * 2019-01-30 2019-06-07 四川中烟工业有限责任公司 一种从白酒丢糟中提取原味酒香风味物质的方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023198993A1 (fr) 2022-04-15 2023-10-19 Lesaffre Et Compagnie Procédé d'obtention d'acétoïne
FR3134575A1 (fr) 2022-04-15 2023-10-20 Lesaffre Et Compagnie Procédé d’obtention d’acétoïne

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