WO2012160256A1 - Procédé et appareil pour séparer un produit acide hydroxycarboxylique - Google Patents

Procédé et appareil pour séparer un produit acide hydroxycarboxylique Download PDF

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Publication number
WO2012160256A1
WO2012160256A1 PCT/FI2012/050482 FI2012050482W WO2012160256A1 WO 2012160256 A1 WO2012160256 A1 WO 2012160256A1 FI 2012050482 W FI2012050482 W FI 2012050482W WO 2012160256 A1 WO2012160256 A1 WO 2012160256A1
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WO
WIPO (PCT)
Prior art keywords
acid
suspension
separation
hydroxycarboxylic acid
stage
Prior art date
Application number
PCT/FI2012/050482
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English (en)
Inventor
Matti Ristolainen
Jutta Nuortila-Jokinen
Esa Hassinen
Kati Eskelinen
Original Assignee
Upm-Kymmene Corporation
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Filing date
Publication date
Application filed by Upm-Kymmene Corporation filed Critical Upm-Kymmene Corporation
Publication of WO2012160256A1 publication Critical patent/WO2012160256A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • 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
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • B01D9/02—Crystallisation from solutions
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42—Hydroxy-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/56—Lactic acid

Definitions

  • the invention relates to the method as de ⁇ fined in the preamble of claim 1 and to the apparatus as defined in the preamble of claim 9 for separating a hydroxycarboxylic acid product from a suspension con ⁇ taining hydroxycarboxylic acid formed as a result of hydrolysis and fermentation of lignocellulose-based raw material. Further, the invention relates to the use of a hydroxycarboxylic acid as defined in the claim 13. BACKGROUND OF THE INVENTION
  • Hydroxycarboxylic acid based products e.g. lactic acid
  • lignocellulose-based raw stock e.g. from waste wa ⁇ ters, residue flows and sludges derived from paper and/or pulp mill.
  • the waste waters contain organic ma ⁇ terial such as fibers and traces of bleaching agents.
  • the process of hydroxycarboxylic acid production is usually based on enzymatic hydrolysis and fermenta ⁇ tion. The produced hydroxycarboxylic acid is separated for example by crystallization.
  • WO 9919290 is known a process for the production of lactic acid products from mixture con ⁇ taining free lactic acid and dissolved lactate salt.
  • Preferred mixtures for processing are obtained from fermentation broths, preferably from fermentation processes conducted at a pH of 4.8 or lower.
  • From WO 00/56693 is known a method for purificating lactic ac ⁇ id by distillation and crystallization.
  • the objective of the invention is to disclose a new type of a method and apparatus for separating a hydroxycarboxylic acid product from a suspension con ⁇ taining hydroxycarboxylic acid formed as a result of hydrolysis and fermentation of lignocellulose-based raw material. Further, the objective of the invention is to disclose use of hydroxycarboxylic acid as a con ⁇ centrating agent for increasing the concentration above the eutectic point of the concentration.
  • the method for separating a hydroxycarboxylic acid product from a suspension containing hydroxycarboxylic acid formed as a result of hydrolysis and fer- mentation of lignocellulose-based raw material accord ⁇ ing to the present invention is characterized by what is presented in claim 1.
  • the apparatus for separating a hydroxycarbox ⁇ ylic acid product from a suspension containing hy- droxycarboxylic acid formed as a result of hydrolysis and fermentation of lignocellulose-based raw material according to the present invention is characterized by what is presented in claim 9.
  • Fig. 1 is a flow chart illustration of a method and an apparatus according to one embodiment of the present invention.
  • Fig. 2 shows a schematic illustration of an eutectic system of water (A) and carboxyhydroxyl acid (B) .
  • the invention is based on a method for sepa- rating a hydroxycarboxylic acid product from a suspen ⁇ sion containing hydroxycarboxylic acid formed as a re ⁇ sult of hydrolysis and fermentation of lignocellulose- based raw material.
  • the suspension containing hydroxycarboxylic acid is treated by a two-stage separation to form the hydroxycarboxylic acid product, the two-stage separation comprising a first separation stage in which water is separated, preferably at least a part of water is removed, from the suspension and a second separation stage in which hy- droxycarboxylic acid product is separated, preferably is concentrated and purified, from the suspension from which water has been removed, and hydroxycarboxylic acid is added to the suspension before the second separation stage, preferably between the first and second separa- tion stages, to increase the concentration of the hy ⁇ droxycarboxylic acid in the second stage.
  • the invention is based on an apparatus for separating a hydroxycarboxylic acid product 33 from a suspension 31 containing hydroxycarboxylic acid formed as a result of hydrolysis 11 and fermentation 12 of lignocellulose-based raw material 2.
  • the apparatus includes a two-stage sepa ⁇ ration device 36a-b for treating the suspension 31 containing hydroxycarboxylic acid to form the hydroxycar- boxylic acid product 33, and the two-stage separation device comprises a first separation device 36a in which water 37 is separated from the suspension 31 and a se ⁇ cond separation device 36b in which hydroxycarboxylic acid 33 is separated from the suspension 32 from which water has been removed, and a means 39,40 for adding hy- droxycarboxylic acid to the suspension 32 before the se ⁇ cond separation device 36b to increase a concentration of the hydroxycarboxylic acid in the second separation.
  • the invention is based on an use of hydroxycarboxylic acid as a concentrating agent in a two-stage separation process, e.g. method and/or appa ⁇ ratus, comprising a first stage in which water is re ⁇ moved from the suspension containing hydroxycarboxylic acid and a second stage in which hydroxycarboxylic acid is separated from the suspension containing hydroxycar- boxylic acid and the hydroxycarboxylic acid is led be ⁇ tween the two separation stages of the hydroxycarbox ⁇ ylic acid separation.
  • a two-stage separation process e.g. method and/or appa ⁇ ratus
  • the invention is specifically based on the use of at least two-stage separation method for sepa- ration of hydroxycarboxylic acid, e.g. lactic acid, wherein firstly at least a part of water, preferably mainly water, is removed and secondly hydroxycarbox ⁇ ylic acid is concentrated and purified.
  • the eutectical point of the separation preferably crystallization, is controlled in such a way that the resulting pure hydroxycarboxylic acid is collected in an acid form, not as a salt.
  • the new advantage of the invention is that the resulting hydroxycarboxylic acid is pure and ready to be used and no additional purification steps are needed.
  • An additional new feature is that the con ⁇ centration of the hydroxycarboxylic acid in the feed of the hydroxycarboxylic acid purification is in- creased by recycling or by adding pure hydroxycarbox ⁇ ylic acid to the feeding point which is located after the water removing. Then the eutectical point can be exceeded by jumping over it.
  • hydroxycarboxylic acid is gen ⁇ erated in the form of acid and a right side of the eu ⁇ tectical point is achieved.
  • the eutecti ⁇ cal point is dependent on an effluent, suspension com ⁇ position and concentrations of water and hydroxycarboxylic acid.
  • FIG 2 is shown a schematic illustration of a eutectic system of water (A) and carboxyhydroxyl acid (B) .
  • SMC crystalli ⁇ zation
  • stages are connected in series.
  • SMC1 the main component in the feed is water, i.e. the hydroxylic acid is present in a very low co- centration.
  • SMC1 the first SMC stage
  • the pure water is crystallised and removed from the system as a solid phase until the process is stopped at a concentration Xw.
  • the concentration Xw is more than 1 % below the concentration in the eutectic point, Xe .
  • the uncrystallised fraction of the feed is fed in the second suspension melt crystallisa ⁇ tion unit, SMC2 to increase the concentration of the component B (hydroxylic acid) above the concentration Xe .
  • the starting concentration Xh in SMC2 shown in Fig. 2 is thus more than 1 % higher than Xe .
  • the crys ⁇ tallisation process in SMC2 then follows the curve shown on the right hand side of the eutectic point (Xe) in Fig 1, where the pure hydroxylic acid is crys ⁇ tallised and removed from the system as the solid phase. A part of crystallised acid may liquify when temperature rises. The obtained final purity of the hydroxylic acid is 99 %.
  • Lignocellulose means in this connection a ma- terial formed from cellulose, hemicellulose and lig- nin.
  • Lignocellulose-based material means in this con ⁇ nection any material containing cellulose and/or hemicellulose, which may also contain, in addition to cel ⁇ lulose and hemicellulose, lignin, starch and/or other substances.
  • an effluent is used as a raw material.
  • the raw material can includes one or more than one component.
  • ef ⁇ fluent means any effluent selected from the group of pulp mill effluent, paper mill effluent, saw mill ef ⁇ fluent, food manufacturing effluent, brewing industry effluent and their combinations.
  • the effluent compris ⁇ es alkaline and/or acidic waste waters, filtrates and residual waters of the process.
  • the effluent is a waste water, waste sludge or residue flow from the pulp mill.
  • the efflu ⁇ ent is a waste water.
  • the first ef ⁇ fluent can include alkaline and/or acid components, e.g. a bleaching filtrate, and/or any residue effluent which comes from the pulp mill.
  • the effluent contains, at least in some quantity, the lignocellulosic materi ⁇ al described above.
  • the effluent can includes one or more than one component.
  • the raw material can also contain, in addition the effluent, other subtances.
  • a hydroxycarboxylic acid can include at least one hydroxycarboxylic acid or combina ⁇ tion of different hydroxycarboxylic acids.
  • hydroxycarboxylic acid means any hydroxycar ⁇ boxylic acid.
  • a hydroxycarboxylic acid product can include any hydroxycarboxylic acid or combination of different hydroxycarboxylic acids.
  • the hydroxycarboxylic acid is selected from the group of glycolic acid, 3- hydroxypropanoic acid, lactic acid, succinic acid, xy- loisosaccharine acid, anhydroisosaccharine acid, 3,4- dihydroxybutyric acid, 4-hydroxybutyric acid, glyceric acid, maleic acid, citric acid, oxalic acid and their combinations.
  • hydroxycarboxylic acid is selected from hydroxyl carboxylic acids formed from carbohydrate materials.
  • the hydroxycarboxylic acid can be formed by any method comprising a hydrolysis and fermentation stages.
  • the hydrolysis can be select ⁇ ed from the group of acid hydrolysis, alkaline hydrol ⁇ ysis, enzymatic hydrolysis and their combinations.
  • the hydrolysis and the fermentation may be carried by any method or process or apparatus known per se and suitable for the purpose can be used in hy ⁇ drolysis and fermentation.
  • the suspension containing the hydroxycarboxylic acid is filtered for separating fermentation residue and/or lignin from the suspension.
  • the filtration device can be any filtration device known per se and suit- able for the purpose can be used in the filtration of the suspension.
  • a residue of the fer ⁇ mentation can be treated by an anaerobic treatment, burning and/or lignin purification.
  • the first separation stage 36a is accomplished by a separation process selected from the group of crystallization, evaporation, filtration, e.g. ultrafiltration and nano- filtration, electro-osmotic treatment, suspension melt crystallization and their combinations.
  • the first separation stage is suspension melt crystallization, preferably water crystallization.
  • the first separation device 36a is selected from the group of evaporator, crystalli ⁇ zation device, filtration device, osmotic device, sus ⁇ pension melt crystallization device and their combina- tions.
  • the first separation device is a suspension melt crystallization device.
  • the first separation device can be any separation and/or concentration device known per se and suitable for the purpose can be used in the water separation and concentration of the hydroxycarboxylic acid composition.
  • the se ⁇ cond separation stage 36b is accomplished by suspen ⁇ sion melt crystallization.
  • the second separation stage is hy ⁇ droxycarboxylic acid crystallization, e.g. lactic acid crystallization.
  • the second separa ⁇ tion device 36b is a suspension melt crystallization device, which can be any suspension melt crystallization device known per se and suitable for the purpose can be used in the separation of the hydroxycarboxylic acid and the concentration of the hydroxycarboxylic acid composition .
  • the apparatus comprises a recirculating means 39 for recirculating at least a part of the hydroxycar- boxylic acid 33 formed in the second separation device 36b to the suspension 32 placed between the first 36a and second 36b separation devices.
  • the separation process com ⁇ prises at least one intermediate stage between the first and second separation stages.
  • the hy ⁇ droxycarboxylic acid is added into the intermediate stage.
  • the separation comprises at least on pre-treatment stage before the first separation stage.
  • the separation comprises at least one post-treatment stage after the second separa- tion stage.
  • the concentrated hy- droxycarboxylic acid product 33 formed is used as such to have a desired product or is processed further to have a desired product.
  • the hy- droxycarboxylic acid procuct is used as a chemical, biochemical and/or polymer component.
  • the hydroxycarboxylic acid product is lactic acid.
  • Fig. 1 shows an apparatus for producing and separating lactic acid by the method according to the invention .
  • the apparatus of Fig. 1 includes an effluent feeding means 20 for feeding an effluent used as a raw stock 2 from a pulp mill 1.
  • the effluent feeding means 20 comprises a pipe or a duct for transporting the ef ⁇ fluent.
  • the effluent feeding means may also comprise pump(s) or any other equipment needed for feeding the effluent from the pulp mill to an ultrafiltration device 10.
  • the apparatus includes an ultrafiltration device 10 for removing water 17 from the raw stock 2 and for concentrating the raw stock to provide a concentrate 3.
  • the process includes a hydrolysis device 11 based on an acid hydrolysis or alkaline hydrolysis for hydrolyzing the concentrate 3 to form saccharides 4, and a fermentation device 12 for fermentating the saccharides 4 to form lactic acid.
  • the apparatus includes a pH controlling means 18 a-c for controlling and adjusting the pH of the fermentation 12 by using a second efflu- ent 16 from the pulp mill 1.
  • a pH controlling means 18 a-c for controlling and adjusting the pH of the fermentation 12 by using a second efflu- ent 16 from the pulp mill 1.
  • the concentrate 3 can be treated in a dwell tank 13, es ⁇ pecially if a bleaching filtrate is used as the second effluent.
  • the second effluent can be fed in the dwell tank 13 and/or in the fermentation 12.
  • the bacteria are mixed with the concentrate 3 in the hydrolysis step 11.
  • the pH controlling means comprises at least one measur ⁇ ing device 18a for measuring the pH in the fermentation 12 and/or before the hydrolysis 11, a feeding device 18c for feeding the second effluent and a control unit 18b for controlling and adjusting the feeding of the second effluent on grounds of the pH measurements.
  • the feeding device is pump or any other suitable equipment for feed ⁇ ing the second effluent from the pulp mill to the dwell tank 13 and/or the fermentation device 12.
  • the control unit 18b contains reception means to receive signals from the measuring devices 18a, calculation means to form control signals, and control signal transmitting means to transmit the control signals formed in the con ⁇ trol unit to the feeding device 18c.
  • a suspension 30 including lactic acid is led to a filtering device 35, where lignin and fermentation waste 38 is filtered from a fermentation mother suspension 31 including lactic acid.
  • the fermentation mother suspension 31 including lactic acid is concentrated in a two-stage concentration device 36a-b to form concentrated lactid acid 33.
  • the apparatus of this invention comprises the two-stage con ⁇ centration device.
  • the two-stage concentration device comprises a first suspension melt crystallization device 36a where water is removed from the fermentation mother suspension 31 including lactic acid and a second suspension melt crystallization device 36b where lactic acid 33 is separated from the fermentation mother suspension 32 from which water 37 has been removed for forming lac- tic acid 33 with concentration over 90 %.
  • Water 37 from the first crystallization device 36a is led to the pulp mill 1.
  • the residue fermentation mother suspension 34 is recirculated into the suspension 30 after the fermenta ⁇ tion 12.
  • the apparatus of the invention com- prises means 39 and 40 for adding lactic acid to the suspension 32 before the second crystallization device 36b to increase a concentration of the lactic acid in the second stage 36b.
  • a suspension 30,31 containing lactic acid is formed from the pulp mill effluent 2 con- taining mainly bleaching filtrate by a hydrolysis 11, e.g. an entzymatic hydrolysis, and fermentation 12.
  • a hydrolysis the effluent is hydrolyzed to form sac ⁇ charides.
  • the saccharides are fer ⁇ mented to form lactic acid.
  • the suspension 30,31 con- taining lactic acid is led after the hydrolysis and fer ⁇ mentation to the lactic acid separation process 36a-b.
  • the suspension 30 may be filtered, e.g. by an ultrafiltration device 35, for removing lignin and fermentation residue 38 from the suspension 31.
  • Separated lignin and fermantion residue 38 can be further processed e.g. in anaerobic fermenta ⁇ tion, by burning or in lignin purification.
  • the suspension 31 including lactic acid is concentrated by a crystallisation for forming a concentrated lactic acid.
  • the lactic acid separation is based on two-stage crystallization which includes two stages 36a and 36b.
  • the first stage 36a of the separation is water crystallization.
  • the second stage 36b of the separation is lactic acid crystallization.
  • water 37 is removed by crystallization from the suspension 31 to form a suspension 32 from which at least a part of water is removed. After the first stage 36a the suspension 32 contains about 30 % lactic acid.
  • the sus ⁇ pension 32 is supplied to the second stage 36b of the separation.
  • the lactic acid is concentrated and crystalllized from the suspension 32. Simultaneously it is purified.
  • the lactic acid is thus recovered as pure lactic acid in solid form, not as a salt.
  • the concentration of the lactic acid 33 is about 99 %.
  • a residue 34 of the suspension 32 may be returned into the process or utilized in the other process.
  • the separated lactic acid 33 can be used as a chemical, biochemical, polymer component or final product.
  • a part of the sepa ⁇ rated lactic acid 33 is recirculated as a lactic acid flow by the recirculation means 39 to the suspension 32 to to increase a concentration of the lactic acid in the second stage 36b.
  • pure lactic acid is added by the adding means 40 to the suspension 32 to to increase a concentration of the lactic acid in the se ⁇ cond stage 36b.
  • Water 37 from the first stage 36a of the separation may be supplied to the pulp mill 1.
  • the method and the apparatus according to the invention are suitable as different embodiments to be used in the separation of most different hydroxycarbox- ylic acid products, e.g. lactic acid products.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne un procédé et un appareil pour séparer un produit acide hydroxycarboxylique (33) d'une suspension (31) contenant un acide hydroxycarboxylique formé en résultat d'une hydrolyse (11) et d'une fermentation (12) d'une matière première à base de lignocellulose (2). Selon l'invention, la suspension (31) contenant un acide hydroxycarboxylique est traitée par une séparation à deux étapes (36a-b) pour former le produit acide hydroxycarboxylique (33), la séparation à deux étapes comprenant une première étape de séparation (36a) lors de laquelle l'eau (37) est séparée de la suspension et une seconde étape de séparation (36b) lors de laquelle le produit acide hydroxycarboxylique (33) est séparé de la suspension (32) de laquelle l'eau a été éliminée, et de l'acide hydroxycarboxylique (39, 40) est ajouté à la suspension (32) avant la seconde étape de séparation (36b) pour augmenter la concentration de l'acide hydroxycarboxylique lors de la seconde étape. L'invention concerne également l'utilisation de l'acide hydroxycarboxylique en tant qu'agent de concentration.
PCT/FI2012/050482 2011-05-23 2012-05-22 Procédé et appareil pour séparer un produit acide hydroxycarboxylique WO2012160256A1 (fr)

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Application Number Priority Date Filing Date Title
FI20115497A FI20115497A (fi) 2011-05-23 2011-05-23 Menetelmä ja laitteisto hydroksikarboksyylihappotuotteen erottamiseksi
FI20115497 2011-05-23

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107098808A (zh) * 2017-05-05 2017-08-29 湖北壮美生物科技有限公司 一种高纯度、高含量常温不结晶乳酸产品的制备方法及生产装置
CN109694318A (zh) * 2017-10-20 2019-04-30 中国石油化工股份有限公司 生产高纯度乙醇酸的方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0733616A1 (fr) * 1995-03-21 1996-09-25 Hoechst Aktiengesellschaft Procédé de production d'acide glycolique cristallin
WO2000056693A1 (fr) * 1999-03-22 2000-09-28 Purac Biochem B.V. Procede de purification d'acide lactique a l'echelle industrielle
JP2004089177A (ja) * 2002-09-03 2004-03-25 Inha Univ Foundation 製紙スラッジから乳酸を生産する方法
US20050020853A1 (en) * 2002-01-29 2005-01-27 Yoshito Kuroda Process for production of high-purity cyrstals of glycolic acid
WO2006013228A1 (fr) * 2004-08-04 2006-02-09 Kemira Growhow Oyj Procede de recuperation de composants organiques et inorganiques a partir d'un flux de dechets
US20080091047A1 (en) * 2006-10-12 2008-04-17 Gallagher F Glenn Multi-stage glycolic acid crystallization
WO2010118932A1 (fr) * 2009-04-15 2010-10-21 Dsm Ip Assets B.V. Procédé de production d'acide dicarboxylique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0733616A1 (fr) * 1995-03-21 1996-09-25 Hoechst Aktiengesellschaft Procédé de production d'acide glycolique cristallin
WO2000056693A1 (fr) * 1999-03-22 2000-09-28 Purac Biochem B.V. Procede de purification d'acide lactique a l'echelle industrielle
US20050020853A1 (en) * 2002-01-29 2005-01-27 Yoshito Kuroda Process for production of high-purity cyrstals of glycolic acid
JP2004089177A (ja) * 2002-09-03 2004-03-25 Inha Univ Foundation 製紙スラッジから乳酸を生産する方法
WO2006013228A1 (fr) * 2004-08-04 2006-02-09 Kemira Growhow Oyj Procede de recuperation de composants organiques et inorganiques a partir d'un flux de dechets
US20080091047A1 (en) * 2006-10-12 2008-04-17 Gallagher F Glenn Multi-stage glycolic acid crystallization
WO2010118932A1 (fr) * 2009-04-15 2010-10-21 Dsm Ip Assets B.V. Procédé de production d'acide dicarboxylique

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107098808A (zh) * 2017-05-05 2017-08-29 湖北壮美生物科技有限公司 一种高纯度、高含量常温不结晶乳酸产品的制备方法及生产装置
CN107098808B (zh) * 2017-05-05 2020-01-31 湖北壮美生物科技有限公司 一种高纯度、高含量常温不结晶乳酸产品的制备方法及生产装置
CN109694318A (zh) * 2017-10-20 2019-04-30 中国石油化工股份有限公司 生产高纯度乙醇酸的方法

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FI20115497A (fi) 2012-11-24
UY34084A (es) 2012-11-30

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