WO2019027222A1 - 다가 알코올의 탈색 및 탈취 방법 - Google Patents
다가 알코올의 탈색 및 탈취 방법 Download PDFInfo
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- WO2019027222A1 WO2019027222A1 PCT/KR2018/008674 KR2018008674W WO2019027222A1 WO 2019027222 A1 WO2019027222 A1 WO 2019027222A1 KR 2018008674 W KR2018008674 W KR 2018008674W WO 2019027222 A1 WO2019027222 A1 WO 2019027222A1
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- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
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- B01D15/08—Selective adsorption, e.g. chromatography
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
- B01D15/361—Ion-exchange
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/001—Processes specially adapted for distillation or rectification of fermented solutions
- B01D3/002—Processes specially adapted for distillation or rectification of fermented solutions by continuous methods
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/001—Processes specially adapted for distillation or rectification of fermented solutions
- B01D3/003—Rectification of spirit
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/148—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step in combination with at least one evaporator
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- 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
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/422—Electrodialysis
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/207—1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/10—Vacuum distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/202—Ethylene glycol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/205—1,3-Propanediol; 1,2-Propanediol
Definitions
- the present invention relates to a method of decolorizing and deodorizing a polyhydric alcohol. More particularly, the present invention relates to a method for decolorizing and deodorizing a polyhydric alcohol after a separation step.
- Polyhydric alcohols are compounds in which a plurality of hydroxyl groups (-OH) are present in one molecule, and may be referred to as glycols in the case of dihydric alcohols and glycerol in the case of trihydric alcohols. Polyhydric alcohols are used as hydrophilic and quantitative solvents, and are also applied to various fields such as various cosmetic compositions, pharmaceutical additives, automobile antifreeze, and the like.
- 2,3-butanediol is widely used as a raw material or additive for electronic material additives, insecticides, cosmetics, beauty products and the like, and is also used in the field of medicine due to chiral characteristics The possibility is increasing.
- 2,3-butanediol can be produced by a chemical method such as the hydration reaction of 2,3-butene oxide, or may be synthesized through a bio-based fermentation process to produce 2,3-butanediol of specific optical activity.
- 2,3-butanediol needs to be produced in order to be applied to cosmetics, medicines and the like.
- 2,3-butanediol stock solution Due to a small amount of impurities which have not been removed in the separation and purification processes, 2,3-butanediol stock solution, It can be off-flavored with an off-white color.
- An object of the present invention is to provide a method for decolorizing and deodorizing a polyhydric alcohol having a high efficiency and a removal capacity.
- An object of the present invention is to provide a high-efficiency, removing capacity polyhydric alcohol decolorizing and deodorizing system.
- the mixed liquid comprises the first polyhydric alcohol, water, and a neutralizing agent.
- the neutralizing agent comprises at least one of a carbonate or a metal hydroxide.
- stripping treatment comprises injecting water or steam into the second polyhydric alcohol and then removing water through a distillation column or short distillation.
- fractionation distillation treatment further comprises discharging the edifice in the distillation column.
- fractional distillation treatment further comprises removing residues collected at the bottom of said distillation column.
- the adsorption treatment further comprises adding 10 to 100 parts by weight of water to 100 parts by weight of the pretreatment liquid.
- polyhydric alcohol fermentation broth comprises 2,3-butanediol synthesized from biomass.
- a fractionation unit for distilling a first polyhydric alcohol obtained by a separation process A stripping unit for distilling the second polyhydric alcohol supplied from the fractionation unit; And an adsorption unit for removing the dichroic and odorous substances remaining in the polyhydric alcohol fed from the removal unit.
- the distillation process in the polyalcohol decolorization / deodorization process produced through the separation / purification process, the distillation process can be performed before the adsorption treatment such as, for example, activated carbon treatment. Therefore, the dichroic and odorous substances can be removed by the vaporization or fractionation distillation mechanism to reduce the load of the adsorption treatment, and the removal efficiency / removal capacity of the odorous and odorous substances can be increased.
- the adsorption treatment such as, for example, activated carbon treatment. Therefore, the dichroic and odorous substances can be removed by the vaporization or fractionation distillation mechanism to reduce the load of the adsorption treatment, and the removal efficiency / removal capacity of the odorous and odorous substances can be increased.
- the distillation treatment may include a plurality of steps of continuous distillation processes.
- the distillation treatment may include a fractional distillation treatment and a stripping treatment.
- the fractional distillation treatment the different color and off-odor substances are removed in bulk units due to the difference in boiling point, and the remaining unoccupied and odorous substances can be removed in more minute units.
- adsorption treatment is carried out to obtain a colorless, odorless polyhydric alcohol in which the substantially odorous and odoriferous substances are completely removed.
- a substantially colorless, odorless 2,3-butanediol may be produced from a 2,3-butanediol synthesis solution comprising a number of impurities, dichroism, and odoriferous materials synthesized on a bio-based basis.
- FIG. 1 is a conceptual diagram for explaining a decoloring and deodorizing system for polyhydric alcohols according to an embodiment of the present invention.
- FIG. 2 is a process flow chart showing a method of decolorizing and deodorizing a polyhydric alcohol according to an embodiment of the present invention.
- 1 is a conceptual diagram for explaining a decoloring and deodorizing system for polyhydric alcohols according to an embodiment of the present invention.
- 2 is a process flow chart showing a method of decolorizing and deodorizing a polyhydric alcohol according to an embodiment of the present invention.
- a system for separating and deodorizing a polyhydric alcohol 100 may comprise a distillation unit and an adsorption unit (C).
- the distillation unit may comprise a fractionation unit A and a stripping unit B.
- the fractionation unit (A) may comprise a first reservoir (200) and a fractionation column (210).
- the detaching unit B may include a second storing unit 205 and an unloading column 230.
- the adsorption unit (C) may include an adsorption treatment chamber (250).
- a first mixed solution containing a first polyhydric alcohol can be prepared (for example, step S10).
- the first polyhydric alcohol may be a polyhydric alcohol that is collected after the separation process for the polyhydric alcohol fermentation broth.
- the polyhydric alcohol fermentation broth can be produced by fermenting a bio-raw material (or biomass) using a strain.
- the bio-raw material may be a kernel, woody and / or starch-based material.
- the starch-based material include starch-containing cereals such as corn, rye, etc., cassava, raw sugar, glucose (glucose) may be used.
- a microorganism capable of producing a fermentation product containing a diol can be utilized without particular limitation.
- Klebsiella, Bacillus, Serratia, Enterobacter, Clostridium, yeast, E. coli and the like are utilized as the microorganisms .
- the above-mentioned bio raw materials and strains can be selected in consideration of a desired target diol.
- the target diol may be 2,3-butanediol.
- the target diol may comprise 2R, 3S-butanediol in the optical isomer of 2,3-butanediol.
- cassava as the bio-raw material and Klebsiella as the strain may be used for the production of 2,3-butanediol.
- K. oxytoca, K. pneumoniae and the like can be used as the above-mentioned strains, and K. oxytoca (K. oxytoca) .
- the polyhydric alcohol fermentation broth can be produced through a saccharification process and a fermentation process.
- the bio-raw material may be pulverized, mixed with a liquid such as fresh water, and a saccharification enzyme may be added to react with the bio-raw material to produce a saccharified liquid.
- the saccharifying enzyme may include, for example, an amylase-based enzyme.
- the fermentation broth can be prepared by injecting the strain into the saccharified solution.
- the fermentation broth can be, for example, not only 2,3-butanediol, which is a target diol, but also monoalcohols and other glycols such as ethylene glycol, diethylene glycol, 1,3-propanediol, , Dipropylene glycol, and the like).
- the fermentation broth may contain various inorganic salts, organic acids, and dyes and odor-inducing impurities such as bio-by-products derived from the strain or its metabolites.
- the separation process may include a process for selectively collecting the desired target diol.
- the separation process may include an ion exchange process, an electrodialysis process, a vacuum distillation process, and the like.
- the method and system for decolorizing and deodorizing according to embodiments of the present invention may be a process and process system to be performed after the separation process.
- the first mixed liquor may comprise the first polyhydric alcohol (e.g., 2,3-butanediol), water, and a neutralizing agent.
- the first mixed liquid may contain dichroic and odoriferous substances that have not been removed in the separation step.
- the neutralizing agent may comprise a carbonate and / or a metal hydroxide.
- the carbonate include, but are not limited to, NaHCO 3 , KHCO 3 , Na 2 CO 3 , K 2 CO 3 , CaCO 3, etc. These may be used alone or in combination of two or more.
- the metal hydroxide include NaOH, Ca (OH) 2 , and Mg (OH) 2. These metal hydroxides may be used alone or in admixture of two or more.
- the carbonate or metal hydroxide may control the pH of the first mixed solution and remove acidic substances such as organic acid and inorganic acid present in the first mixed solution through neutralization or precipitation.
- acidic substances such as organic acid and inorganic acid present in the first mixed solution through neutralization or precipitation.
- removal of odorous and odorous substances through the boiling point difference can be promoted through the addition of the carbonate. Therefore, the efficiency of removing odor and odorous substances in the distillation unit can be improved.
- monovalent carbonate and bivalent carbonate may be used together for neutralization treatment efficiency.
- KHCO 3 and CaCO 3 may be used together as the neutralizing agent.
- the neutralizing agent may be included in an amount of about 0.1 to 1 part by weight based on 100 parts by weight of the first polyhydric alcohol contained in the first mixed solution.
- the neutralizing agent content is less than about 0.1 part by weight, the above-described acid removing effect may not be sufficiently realized.
- the content of the neutralizing agent is more than about 1 part by weight, for example, the amount of the residue generated at the completion of the fractional distillation increases and the recovery rate may be lowered.
- water may be included in an amount of about 5 to 10 parts by weight based on 100 parts by weight of the first polyhydric alcohol.
- the content of water is less than about 5 parts by weight, the impurities including the odorous and odoriferous substances may not sufficiently dissolve. If the content of water exceeds about 10 parts by weight, process yield and efficiency may be impaired.
- Non-limiting examples of the dichroic and deodorant materials include acetaldehyde, acetoin, diacetyl, furfural, and methanol.
- the first mixed solution may be subjected to distillation treatment so as to at least partially remove the dichroic and the offensive material (for example, step S20).
- the distillation treatment may comprise fractional distillation treatment and removal treatment.
- the first mixed liquid may be directly fed and fractionated to produce a second polyhydric alcohol (for example, step S22).
- the second polyhydric alcohol may be an alcoholic liquid from which the odorous and deodorant substances are at least partially removed from the first polyhydric alcohol.
- the first mixed liquid may be introduced into the first storage unit 200 included in the fractionation unit A through the first supply passage 105.
- the first supply channel 105 may be connected to an apparatus, a chamber, a column, and the like for the separation process to receive the first polyvalent alcohol.
- the first mixed liquid supplied to the first storage part 200 is supplied to the fractionation column 210 so that the first polyhydric alcohol flows from the upper part of the fractionation column 210 to the first discharge line 110 And the second polyhydric alcohol may be discharged.
- the boiling point of the first polyhydric alcohol may be lower than that of the second polyhydric alcohol, and thus the first polyhydric alcohol may be separated and discharged from the top of the fractionation column 210 .
- the temperature at which the first polyhydric alcohol can be separated and discharged in the fractionation column 210 is 60 ° C to 80 ° C, and the pressure can be maintained in the range of 7 mbar to 10 mbar.
- the second polyvalent alcohol discharged through the first discharge line 110 may be condensed through the first condenser 310 and moved through the second supply passage 120.
- the eddy stream exiting the fractionation column 210 may be removed externally, for example, through a second discharge line 125 that branches off from the second feed passage 120.
- the polyhydric alcohol and impurities including dichroic and odoriferous substances
- the purity of the second polyvalent alcohol can be improved by discharging and removing the flow of the plant.
- the stream may be recycled back to the fractionation distillation column 210, for example, through a first recovery line 115 coupled to the first condenser 310.
- the target can improve the yield of alcohol and reduce the amount of process by-products or waste.
- the untreated residual of the first mixed liquor after the above-described fractional distillation process can be stored in the first storage 200.
- the residue may be removed or discharged from the fractionation unit (A) to the outside to improve the purity of the second polyhydric alcohol.
- about 85 to 90 parts by weight of the second polyhydric alcohol may be removed from 100 parts by weight of the polyhydric alcohol contained in the first mixture.
- the second polyvalent alcohol supplied from the second supply passage 120 to the detaching unit B can be subjected to the removal process (for example, step S24)
- a second mixed liquid to which water is added to the second polyvalent alcohol may be supplied to the second storage unit 205.
- water may be supplied into the second storage part 205 through the water supply channel 127 to produce the second mixed solution mixed with the second polyhydric alcohol.
- steam may be supplied to the second reservoir 205 to produce a second mixed liquor mixed with the second polyhydric alcohol.
- the content of water or steam relative to 100 parts by weight of the second polyhydric alcohol may range from about 40 to 200 parts by weight, depending on the number of columns used. If the added amount of water or steam is less than about 40 parts by weight, it may not be easy to perform removal of odorous and odorous substances through the removal process. When the added amount of the water or steam exceeds about 200 parts by weight, the load in the detaching unit (B) becomes excessively increased, and the productivity and yield of the target alcohol may be lowered.
- the second mixed liquid may be supplied to the removal column 230 from the second storage unit 205 and may be removed.
- the second and third mixed liquid remaining in the second mixture liquid can be vaporized together with water and removed.
- the removal process may be performed at a temperature that is lower than the boiling point of the alcohol and is higher than the boiling point of water. Further, the removal treatment may be performed at a temperature lower than the temperature in the fractionation distillation treatment (for example, the maximum temperature in the fractional distillation treatment).
- the stripping treatment may be performed at a temperature of about 20 ⁇ to 30 ⁇ , and a pressure of about 15 mbar to 25 mbar.
- the dichroic and odorous substances which are difficult to be removed by the boiling point difference in the fractional distillation can be removed by an interaction such as hydrogen bonding with water or the like.
- ppm levels of the off-odor material may be removed via the stripping process.
- the micro-odorous substances that have not been removed through the fractional distillation treatment may be additionally removed through the stripping process.
- purging with air or nitrogen may be performed during the removal process to facilitate the removal of the dichroic and odoriferous substances.
- the water containing the dichroic and odoriferous substances may be vaporized and extracted from the upper portion (for example, the column portion) of the column 230 and discharged through the second discharge line 235.
- the water discharged from the second discharge line 235 may be refluxed into the stripping column 230 through the second condenser 330 and the second recovery line 125.
- the target multivalent alcohol partially contained in the water may be recovered and the process yield may be improved.
- the uncolored, odorous substance is vaporized and at least partially removed, so that a pretreatment liquid in which the alcohol is more concentrated or purified from the second mixed liquid can be produced.
- the pretreatment liquid is subjected to adsorption treatment to remove the remaining uncolored and odorous substances (for example, step S30).
- the dichroic, odoriferous material can be substantially completely removed through the adsorption treatment.
- the pretreatment liquid may be supplied to the adsorption processing chamber 250 of the adsorption unit C through the third supply passage 130 connected to the second storage part 205.
- the adsorbent can be contacted or mixed with the pretreatment liquid in the adsorption treatment chamber 250.
- the adsorbent may comprise activated carbon.
- the powdered activated carbon injected into the adsorption treatment chamber 250 is contacted with the pretreatment liquid through agitation, and the remaining odorous and odorous substances can be removed.
- 10 to 100 parts by weight of water may be added to 100 parts by weight of the pretreatment solution, and the temperature in the adsorption treatment chamber 250 may be maintained at a temperature of about 70 to 90 ° C.
- the activated carbon may be used in an amount of 0.3 to 1.0 part by weight based on 100 parts by weight of the pretreatment solution. It is possible to effectively remove odorous and deodorant substances even though the activated carbon is used in a relatively small amount compared to the conventional process.
- the adsorption treatment chamber 250 may comprise a bed or column on which activated carbon is immobilized. If a bed or column on which activated carbon is immobilized is used, the system may further comprise a cleaning section for cleaning the bed or column.
- the powdered activated carbon When used as the adsorbent, a process of separating the activated carbon adsorbed by the unoccupied or odorous substance may be further performed.
- the adsorption treatment liquid containing the target multi-alcohol from the adsorption treatment chamber 250 may be supplied to the filtration unit 400 through the fourth supply flow channel 140.
- the activated carbon is filtered together with the uncolored and the off-odor material through the filtration unit 400, and a substantially pure, odorless target polyvalent alcohol of high purity can be obtained through the collection channel 150.
- the treatment liquid discharged from the filtration unit 400 may be recycled to the adsorption treatment chamber 250 through the third recovery line 145 so that the adsorption treatment may be repeatedly performed.
- the adsorption treatment liquid discharged from the filtration unit 400 may be further subjected to reduced-pressure evaporation to remove water, thereby further removing the unusual and odorous components.
- Cassava was pulverized as a raw material and saccharified to be used as a carbon source.
- K. oxytoca GSC112 LK strain was used to obtain a fermentation broth of polyhydric alcohol containing 2,3-butanediol. The fermentation broth was subjected to filtration, electrodialysis, ion exchange, distillation 2,3-butanediol (first polyhydric alcohol) was obtained through the procedure.
- the mixed solution was passed through the upper portion of the reduced- 90 parts by weight of a polyhydric alcohol (second polyhydric alcohol) was taken out.
- the adsorbed solution was passed through a filtration membrane to finally obtain 2,3-butanediol.
- the pretreatment solution removed in Example 1 was supplied into a chamber containing 0.6 parts by weight of activated carbon and 100 parts by weight of ultrapure water with respect to 100 parts by weight of the pretreatment solution and stirred at a rate of 500 rpm for 30 minutes at 80 ° C.
- Example 2 The same first polyhydric alcohol as in Example 1 was fed to a treatment chamber containing 50 parts by weight of water and 5 parts by weight of activated carbon, which were 100 parts by weight of the first polyhydric alcohol, and stirred. Then, water was removed at 40 mbar and 50 ° C And 2,3-butanediol was obtained at 10 mbar.
- the purity (area ratio) of 2,3-butanediol was measured by gas chromatography on the 2,3-butanediol liquid obtained by the examples and the comparative examples. Specifically, gas chromatography analysis was performed using Agilent 6890 GC-MS (column: HP-5MS).
- the color of the 2,3-butanediol obtained by the examples and the comparative examples was measured for the color of the APHA color index.
- the average score was calculated by sensory evaluation of odor development according to the following evaluation criteria for 30 panelists. The evaluation results are shown in Table 1 below.
- Example 2 In the case of Example 2 in which water was removed by evaporation under reduced pressure after addition of water during the adsorption of activated carbon, it can be seen that substantially unusual and odorous substances were completely removed.
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Abstract
Description
Claims (19)
- 분리 공정에 의해 수득된 제1 다가 알코올을 함유하는 혼합액을 제조하는 단계;상기 혼합액을 증류 처리를 통해 이색 및 이취 물질을 예비적으로 제거하여 전처리 액을 생성하는 단계; 및상기 전처리 액을 흡착 처리하는 단계를 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 1에 있어서, 상기 혼합액은 상기 제1 다가 알코올, 물 및 중화제를 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 2에 있어서, 상기 중화제는 탄산염 또는 금속수산화물 중 적어도 하나를 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 2에 있어서, 상기 중화제는 상기 제1 다가 알코올 100 중량부 대비 0.1 내지 1 중량부의 함량으로 포함되는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 1에 있어서, 상기 증류 처리는 분별 증류 처리 및 탈거 처리를 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 5에 있어서, 상기 분별 증류 처리는 상기 혼합액에 대해 직접 수행되며, 상기 탈거 처리는 상기 분별 증류 처리 이후 수득된 제2 다가 알코올에 대해 수행되는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 6에 있어서, 상기 탈거 처리는 상기 제2 다가 알코올에 물 또는 스팀을 주입한 후 증류 칼럼 또는 단증류를 통해 물을 제거하는 것을 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 7에 있어서, 상기 탈거 처리에 있어서 추가되는 물 또는 스팀의 양은 상기 제2 다가 알코올 100 중량부 대비 40 내지 200 중량부인, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 6에 있어서, 상기 탈거 처리는 공기 또는 질소에 의한 퍼징을 더 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 6에 있어서, 상기 분별 증류 처리는 증류 칼럼에서의 초류를 배출하는 단계를 더 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 10에 있어서, 상기 분별 증류 처리는 상기 증류 칼럼의 저부에 수집되는 잔류를 제거하는 단계를 더 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 1에 있어서, 상기 흡착 처리는 상기 전처리 액을 활성탄 처리하는 것을 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 12에 있어서, 상기 활성탄 처리는 분말 활성탄 또는 활성탄 고정 베드를 사용하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 13에 있어서, 상기 분말 활성탄을 사용하는 경우 흡착 처리액으로부터 상기 활성탄을 분리하는 공정을 더 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 12에 있어서, 상기 흡착 처리는 상기 전처리 액 100 중량부 대비 10 내지 100 중량부의 물을 첨가하는 것을 더 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 15에 있어서, 흡착 처리액을 감압 증발시키는 공정을 더 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 1에 있어서, 상기 분리 공정은 다가 알코올 발효액에 대한 이온교환 처리, 전기 투석 또는 감압 증류 중 적어도 하나를 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 청구항 17에 있어서, 상기 다가 알코올 발효액은 바이오매스로부터 합성된 2,3-부탄디올을 포함하는, 다가 알코올의 탈색 및 탈취 방법.
- 분리 공정에 의해 수득된 제1 다가 알코올을 증류 처리하는 분별 증류 유닛;상기 분별 증류 유닛으로부터 공급된 제2 다가 알코올을 증류 처리하는 탈거 유닛; 및상기 탈거 유닛으로부터 공급되는 다가 알코올에 잔류하는 이색 및 이취 물질을 제거하는 흡착 유닛을 포함하는, 다가 알코올의 탈색 및 탈취 시스템.
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CA3067525C (en) | 2022-12-06 |
US11192844B2 (en) | 2021-12-07 |
JP6880246B2 (ja) | 2021-06-02 |
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