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WO2021090250A1 - Processus et système d'extraction de molécules à partir de matrices de particules solides - Google Patents

Processus et système d'extraction de molécules à partir de matrices de particules solides Download PDF

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Publication number
WO2021090250A1
WO2021090250A1 PCT/IB2020/060448 IB2020060448W WO2021090250A1 WO 2021090250 A1 WO2021090250 A1 WO 2021090250A1 IB 2020060448 W IB2020060448 W IB 2020060448W WO 2021090250 A1 WO2021090250 A1 WO 2021090250A1
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WIPO (PCT)
Prior art keywords
solvent
extraction
matrices
solvents
solid particle
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2020/060448
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English (en)
Inventor
Patrizia PEREGO
Alessandro Alberto CASAZZA
Margherita PETTINATO
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIMES Dipartimento di Medicina Sperimentale Universita degli Studi di Genova
Original Assignee
DIMES Dipartimento di Medicina Sperimentale Universita degli Studi di Genova
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DIMES Dipartimento di Medicina Sperimentale Universita degli Studi di Genova filed Critical DIMES Dipartimento di Medicina Sperimentale Universita degli Studi di Genova
Priority to EP20811445.4A priority Critical patent/EP4054735A1/fr
Publication of WO2021090250A1 publication Critical patent/WO2021090250A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0261—Solvent extraction of solids comprising vibrating mechanisms, e.g. mechanical, acoustical
    • B01D11/0265—Applying ultrasound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0207—Control systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0211—Solvent extraction of solids in combination with an electric or magnetic field
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/028—Flow sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid

Definitions

  • the present invention is related to the field of the extraction processes of one or more solutes dis persed in inert solid matrices by using liquid solvents which are diffused in said solid matrices and subse- quently extracted in the form of a relatively concen trated solution as a solute to be subsequently sepa rated by simple separating actions, for example me chanical operations of draining and / or filtration and / or centrifugation and / or squeezing.
  • Object of the invention is in particular a process and a relative system of extraction of target molecules from solid particle matrices, via discontinuous or con tinuous processes, arranged in a packed bed, by using ultrasound, modulations of liquid phased solvents at high dynamic pressures and adjustable temperatures.
  • Extraction with solvents is in general the most used methodology for the separation of molecules from solid matrices and it finds application in various fields including, for example, in the food sector for the recovery of secondary metabolites from plants and from sub-products and residues of primary treatments. Extraction time can vary from a few seconds to several hours depending on the methodology adopted and the ma trix to be treated.
  • the extraction process can take place: in discontinuous mode, which can be exempli fied as an alternation between a loading the extractor and adding solvent phase, and a phase of discharging the solution and unloading the refined product; in semi-continuous mode, which can be exem plified with extractor loading and continuous flow of solvent, with a phase of refined product unloading at the end of the extraction.
  • the extractive yield of various kind of com pounds is mainly influenced by the ongoing conditions under which the extraction process is carried out, us ing a solvent to separate a soluble fraction from a permeable solid.
  • Literature reports various methods that, depend ing on the embodiment, use the aid from high tempera tures (obtained by traditional heating or with micro- waves), or from high solvent pressures or from ultra sounds to increase the extraction yields or to avoid use of certain solvents favouring instead the use of so-called green solvents, i.e. with low environmental impact to be intended as the impact in terms of alter ation from a qualitative and quantitative point of view of the environment, said low environmental impact neg ligible or in any case lower than that resulting from traditionally used solvents in this type of applica tion.
  • a partial and non-limiting example of low envi ronment impact solvent is water, ethanol, ethyl ace tate, glycerol.
  • each known embodiment is characterized by a single method i.e. the known embodiments are focused in the application of one and only one extraction meth odology.
  • thermolabile molecules making them inactive.
  • An alternative may be the extraction with high pressure solvents.
  • This technique has received a lot of attention in recent years as it represents an effi cient alternative to traditional extraction procedures and it is compatible with the requirement of low envi ronmental impact chemistry.
  • High pressure extraction can take place at variable temperatures (50-150 0 C) and at pressures that can reach up to 300 bar.
  • This technique can be performed in closed containers or in columns having solvent flowing in and collection of the extracted molecules as process output.
  • Another known alternative to optimize extraction involves the use of sound waves at a frequency higher than the threshold of human sensitivity, sound waves known as ultrasound, generated and conveyed to the solid matrices containing the molecules to be ex tracted.
  • the positive effect of ultrasound on the ex traction is attributed to the propagation of ultrasonic waves and to the resulting cavitation phenomena.
  • the shear forces due to these two phenomena, lead to an improvement in the material transportation ef fectiveness.
  • the implosions cavitation bubbles gener ate high variations in local pressure, macro-turbu lence, collisions between particles and perturbations in the micro-pores of the particles; all of this leads to an increase in both turbulence and internal diffu sion.
  • cavitation events near to the solid- liquid interface leads to rapid movement in the matrix cavities.
  • Extraction yield can vary depending on different structures of the bonds between molecules the matrix, from the rheology and/or from the different composition of the matrix itself.
  • the selection of solvents is generally targeted to reach a high affinity between solvent and solute.
  • the isolate pressure or temperature increase or ultrasound stress cannot lead to a signif icant release of the molecule of interest if the said molecule has a low solubility in the used solvent due to limited options related to the choice of the sol vent, also in consideration of the environmental im pacts leading to the choice of using products such as water or ethanol.
  • Applicant of the present invention is not aware of processes or plants for the extraction of molecules which, in a single embodiment, pair different method ologies by combining the effectiveness of high pres sures and high temperatures with the effects coming from ultrasound in a packed bed system and are able to work continuously and according to a predefined and known combination, and at the same time optimizable during the extraction treatment when necessary to im prove the extraction efficiency by the solvent.
  • the present invention therefore has the objective of implementing a process and a related system capable of using and combining different operating parameters, typical of different extraction techniques, which are capable of providing in a single equipment an instru- mental versatility able of better satisfying research purposes and industrial applications.
  • Scope of the present invention is to provide a device for research purposes capable of enhance the extraction process of target molecules from solid par ticle matrices arranged in a packed bed, using ultra- sound, modulations of liquid-phased solvents at high dynamic pressures and adjustable temperatures.
  • This extraction technology is particularly suitable for the recovery of molecules even heat-sensitive using hydro alcoholic solvents.
  • the pres- surized solvent permeates through the packed bed con sisting of the matrix to be treated thus extracting the target molecules, with the possibility of exploit ing a variety of operating parameters and configura tions.
  • the solid particles are retained by a metal filter with micrometric mesh, thus obtaining the sim ultaneous separation of the solid from the liquid in a single step.
  • the system to be patented is proposed as instrumentation for academic and industrial research purposes.
  • the invention therefore solves these limitations by means of a process for extracting molecules from solid particle matrices by means of at least one sol vent or a combination of solvents interacting with said solid particle matrices, which operates in an environ ment defined by known environmental parameters com prising at least one or a combination of two or more of the following extraction-aided methods: exposing said solid particle matrices to ul trasonic sound waves; using solvent or a combination of solvents operating at a predetermined fluid-dynamic pressure even greater than the ambient pressure; using solvent operating at a predetermined temperature also different from the ambient pressure; heating and/or cooling, also dynamically, said liquid and/or solid matrices; each method being able to be described by one or more specific operating parameters, and being said process operative through: controlled alteration of the chemical prop erties of said solvent, possibly obtained as a combi nation, even sequential, of two or more solvents having mutually different chemical properties; controlled alteration of the parameters de scribing said ultrasonic waves involved in said ex traction process; controlled
  • the invention allows many advantages compared to known techniques including: high versatility in the extraction process as it offers the possibility of combining in a single equipment, operating from discontinuous to continuous mode, assisted extraction by high temperatures, high pressures even pulsed and by ultrasound to accelerate the extraction kinetics. allowing to operate at low temperatures, where necessary, accelerating the extraction process through the combined use of high pressure and ultra sound to facilitate the penetration of the solvent into the solid matrix, improving the transfer of material, improving the mixing and the release of the analyte for cellular breakage while avoiding the use of high temperatures as a key parameter to accelerate the ex traction kinetics and consequently avoiding the poten tial degradation of bioactive thermolabile molecules, said degradation which is typical of the techniques known in the state of the art; using simple, eco-compatible solvents with physical conditions close to the ambient physical con ditions instead of subcritical fluids at high pressures or high temperatures.
  • the invention whose one executive form is called Solid-Liquid Multi-variable Extractor or in its acro nym "SoLVE"
  • Solid-Liquid Multi-variable Extractor or in its acro nym "SoLVE”
  • SoLVE Solid-Liquid Multi-variable Extractor
  • the proposed system allows to perform the ex tracting and separating operations of the solid matrix from the extract in a single equipment, with signifi cant savings in post-treatment operations.
  • the invention can be imple mented in accordance to embodiments that operates by applying a dynamic pressure (also pulsed), temperature and ultrasounds on a packed bed system made of the raw material from which it is aimed to recover the products of interest, being able to work at the same time on a multiplicity of variables that can satisfy the differ ent requirements related to the specific chemical na ture of the molecules to be extracted: solvent type, which can also be varied over time by imposing a gradient and allowing the sequential extraction of different molecules from the same matrix; temperature, which can be increased and/or reduced according to the thermolability of the products to be extracted; dynamic pressure, able to enhance the ability of the solvent to penetrate inside porous matrices, also acting on the surface tension of the solvent it self, simultaneously acting as a pushing force for the filtration of the extract and to promote the transfer of matter thanks to the fluid flowing; ultrasound which, through the phenomenon of cavitation, acts on the cellular structure of the solid matter causing a significantly accelerated release of
  • thermosensitive molecules such as, for example, polyphenols, proteins and bioactive compounds from plant matrices, which are widely used in the al imentary, cosmetic and pharmaceutical fields.
  • thermosensitive molecules such as, for example, polyphenols, proteins and bioactive compounds from plant matrices
  • the proposed process and system can also be used with advantages for the extraction of other molecules and fractions of multiple types and compositions.
  • the conventional extraction methods which use the temperature as the main param eter for increasing yields and extraction speed, are inefficient because: they cause a degradation of the molecules of interest or a loss of molecular activity; they accelerate unwanted chemical reactions with the consequent formation of undesired compounds; they make it impossible to obtain elevated recoveries of the compounds contained in the solid ma trices, being forced to operate with very short ex traction times or with unfavourable thermodynamics; they have a reduced selectivity.
  • the present invention also finds po tential applications for the purification of polluted solid materials or for the removal of undesired mole cules from complex matrices, thanks to the possibility of setting operating parameters capable of increasing the focus towards specific molecules, avoiding the co extraction of other unwanted compounds.
  • the invention leverages a hydrodynamic pressure imposed by a simple piston pump, assisted by the use of an ultra sonic probe and heat exchangers in different parts of the plant that can heat up or cool down as needed and allows the sequential extraction, and the preservation from degradative reactions, of molecules of a different type from the same matrix and in a short time.
  • the process operates conjunction with mathematical models for predicting the system behaviour as a function of the system operating parameters and as a function of the characteristics of the said solid particle matrix.
  • the process can be optimized with programmed experiments according to the various opti- mization techniques which are based on statistical mod els such as the so-called Response Surface Methodology that analyses the impact of the input parameters var iation on the results without involving theoretical models which would be hardly definable in consideration of the multiplicity of extraction methods that charac terize the invention.
  • the invention offer considerable advantages over the extraction sys tems available in the state of the art, allowing in a single system the possibility of operate different con figurations (discontinuous, semi-continuous, continu ous) and to take advantage from the application of different parameters able to increase extraction yields and reduce operating times.
  • the proposed system allows to perform the extracting and separating operations of the solid matrix from the extract in a single equipment, with significant savings in post-treatment operations and it allows the application of a dynamic pressure (also pulsed), temperature and ultrasounds on a packed bed system made of the raw material from which it is aimed to recover the products of interest, being able to work at the same time on a multiplicity of variables that can satisfy the different requirements related to the specific chemical nature of the molecules to be ex tracted.
  • Such multiplicity of methods and variables raises the complexity to create a theoretical model that would describe the expected result as a function of the input parameters whereas the combination with mathemati cal/statistical techniques facilitates the optimiza tion of the process in terms of obtainable results.
  • Other embodiments can include one or more inter faces for user interaction, e.g. in the form of a graphic display possibly equipped with tactile sensors, whose combined use can interact with the control elec tronics in different modes such as for example early or delayed activation processes, control parameters calibration included parameters based on the raw mate rial, duration, partialization, etc.
  • the automated or partially automated activa tion of one or more devices involved in the extraction process is provided.
  • the automatisms can therefore be controlled through control signals managed by an elec tronic control unit, which electronic control unit can be dedicated or shared with other system management and/or supervision features.
  • the control unit preferably running a firmware and/or control software contained in said control unit, executes algorithms that contribute to the extraction process execution by coordinating the devices involved and offering man to machine interface to display the process status and/or to interact with at least one local or remote operator, possibly executing the algo rithms included in the mathematical/statistical models for predicting the result and optimizing the result, e.g. by suggesting which method or which solvent to use for the extraction.
  • fig. 1 presents the overall view of a system implementing the extraction method object of the invention.
  • the listed figure supports the in dicative, and therefore non-limiting, description of a preferred but not exclusive embodiment of the said in vention.
  • the system consists of a device for flowing an extracting agent, for example in the form of one or more piston pumps 130, by means of which it is possible to circulate said extracting agent consisting of one or more solvents, which are two in the current embod iment and indicated with references 10 and 11, or a combination of said solvents, flowing through at least one packed bed column, which are two in the current embodiment and indicated with references 211 and 221.
  • an extracting agent for example in the form of one or more piston pumps 130, by means of which it is possible to circulate said extracting agent consisting of one or more solvents, which are two in the current embod iment and indicated with references 10 and 11, or a combination of said solvents, flowing through at least one packed bed column, which are two in the current embodiment and indicated with references 211 and 221.
  • the pump 130 has a settable flow rate of extract ing agent which can consist of a pure solvent, in a mixture or in two or more solvents fed by means of a gradient.
  • the two solvents 10, 11 are contained in the respective containers 100, 101 from which containers the said solvents are drawn by means of suitable ducts 102, 103.
  • the flow of the single solvent is controlled by means of dedicated control mechanisms, consisting for example of flow control valves 110 and 120, capable of operating independently and in every position from a state of complete opening to a state of complete occlusion of the controlled solvent flow.
  • the solvents 10 and 11 travel through the respective pipes 102 and 103 in the direction indicated by the arrows 104 and 105 to be mixed into the fitting 125 and to continue towards a liquid bath container 200 which contains the particle matrices 210 and 220.
  • the hydrodynamic conditions of the extracting agent are detected by a number of devices located downstream of the pump 130, for example a pres sure gauge 140 and a flow meter 150 and a thermometer 171 downstream of the heating device 170.
  • Packed columns 211 and 221 house the solid parti cle beds 210 and 220, which constitute the solid matrix from which targeted for the extraction the component or components of interest, which solid particle beds
  • 210 and 220 are segregated within the respective col umns 211 and 221 thanks to special metal filters 212, 213, 222, 223 placed respectively in the column inlet and outlet sections.
  • Extracting agent flowing into the columns is reg ulated by means of dedicated devices at the inlet and outlet of each individual column, said devices being feasible as shut-off valves 180, 181, 190, 191, said devices being also capable to completely occlude the flow of extracting agent to and from the single column
  • complete occlusion of the inlet and outlet valves involves the isolation of the re lated column, in this example the column 211, thus allowing maintenance operations and / or replacement of part of the extraction system without interrupting the extraction cycle which can continue on the remain ing columns, column 221 in this example.
  • the solids bed is axially traversed by the pres surized solvent, the pressure value is monitored by the pressure gauges 140 and 250, the latter located at the outlet of extraction columns 211 and 221, and the extraction process takes place during the traversing of the solids bed by the extracting agent.
  • the extraction phase is assisted by the effect of ultrasound, generated by a probe 240 and a transducer 230 immersed in a liquid bath 201 contained in the liquid bath container 200 that also contains the col umns 211 and 221 which are submerged in said liquid bath whose temperature can be set by means of a special control system of the liquid bath 30.
  • control system of the liquid bath 30 can increase the temperature of the liquid bath 201 and therefore of the columns 211 and 221, in order to help the extraction kinetics, or in order to com pensate the temperature increase due to ultrasound ap plication by reducing the temperature of the liquid bath 201.
  • variation of the temperature of said liquid bath is obtained by means of at least one heater 300 and at least one cooler 330 which act on the fluid composing the liquid bath whose flow to and from the liquid bath container 200 is regulated by dedicated valves 310, 320, 340 and 350, said valves being also able to exclude the relative devices 300 and 330 from the extraction system.
  • Temperature of the fluid included in the said liq uid bath is detected by the thermometer 370 and the detected value is sent to the thermostat 360 whose control signals coordinate the operation of the said heaters 300 and / or chillers 330.
  • the valve 181 located downstream of the col umn which allows the pressure regulation in the sys tem, can be used to vary the pressure conditions to impose a constant dynamic pressure, pulsed or ramp shaped depending on whether the system is working by feeding the extracting agent in discontinuous, semi- continuous or continuous extracting mode.
  • the second column 221 which has a configuration identical to the first, allows to work in parallel or alternate to the column 211 and, where appropriate, further embodiments can be realized contemplating a plurality of said columns or more in general containers for matrices solid parti cles, even reciprocally different, offering the possi bility to operate without interruptions and/or on dif ferent matrices.
  • an operative example of alternate extraction provides that, while the column 211 operates the extraction process, the column 221 can be isolated by closing the valves 190 and 191, so the column 221 can thus be emptied and the bed regen erated with a new solid matrix.
  • the valves 190 and 191 are opened while the valves 180 and 181 are closed, allowing the operation of the extraction process in packed column 221 and the regeneration of the matrix 210.
  • the extracted material filtered by the metal fil ters 213 and 223 flow out of the columns through the ducts 251 and the valve 260 to reach a heat exchanger 270 that works with a pressure lower than the column, allowing a cool down of the extract before its collec tion which takes place through valve 280.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Acoustics & Sound (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Automation & Control Theory (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

L'invention concerne un processus d'extraction de molécules à partir de matrices de particules solides au moyen d'au moins un solvant ou d'une combinaison de solvants interagissant avec lesdites matrices de particules solides, comprenant la combinaison d'au moins deux procédés d'aide à l'extraction et fonctionnant par une altération contrôlée des paramètres et/ou des propriétés dudit solvant ou d'une combinaison séquentielle de deux solvants ou plus. L'invention concerne en outre un système d'extraction de molécules à partir de matrices de particules solides au moyen d'au moins un solvant ou d'une combinaison de solvants interagissant avec lesdites matrices de particules solides selon la partie de procédé de l'invention elle-même.
PCT/IB2020/060448 2019-11-08 2020-11-06 Processus et système d'extraction de molécules à partir de matrices de particules solides Ceased WO2021090250A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20811445.4A EP4054735A1 (fr) 2019-11-08 2020-11-06 Processus et système d'extraction de molécules à partir de matrices de particules solides

Applications Claiming Priority (2)

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IT102019000020630 2019-11-08
IT102019000020630A IT201900020630A1 (it) 2019-11-08 2019-11-08 Processo e sistema per l’estrazione di molecole da matrici solide particellari

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT202200026727A1 (it) 2022-12-23 2024-06-23 Piovan Spa Apparato e metodo per decontaminare materiale plastico

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Publication number Priority date Publication date Assignee Title
EP1547679A1 (fr) * 2002-08-01 2005-06-29 Consejo Superior De Investigaciones Cientificas Procede de separation ou d'extraction au moyen de fluides supercritiques assiste par ultrasons de haute intensite
CN101274156A (zh) * 2007-12-18 2008-10-01 华南理工大学 天然产物有效成分的超声强化亚临界水萃取方法及装置
CN103861320A (zh) * 2012-12-17 2014-06-18 财团法人工业技术研究院 萃取装置与萃取方法
US20160144292A1 (en) * 2014-11-26 2016-05-26 Paradigm Supercritical Innovations LLC Supercritical fluid extraction apparatuses and methods for operating the same
WO2016118034A2 (fr) * 2015-01-19 2016-07-28 Patrascu Mariana Procédé et installation d'extraction de composés biologiquement actifs à partir de plantes et réacteur opérant en continu pour l'extraction assistée par micro-ondes et ultrasons desdits composés biologiquement actifs à partir de plantes
US20160318972A1 (en) * 2015-04-30 2016-11-03 Yang-Chang Wu Preparation method and analytic method for the extract of antrodia cinnamomea
WO2019169477A1 (fr) * 2018-03-09 2019-09-12 Mazza Innovation Ltd. Extraction par solvant sous pression de charges de biomasse végétale

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1547679A1 (fr) * 2002-08-01 2005-06-29 Consejo Superior De Investigaciones Cientificas Procede de separation ou d'extraction au moyen de fluides supercritiques assiste par ultrasons de haute intensite
CN101274156A (zh) * 2007-12-18 2008-10-01 华南理工大学 天然产物有效成分的超声强化亚临界水萃取方法及装置
CN103861320A (zh) * 2012-12-17 2014-06-18 财团法人工业技术研究院 萃取装置与萃取方法
US20160144292A1 (en) * 2014-11-26 2016-05-26 Paradigm Supercritical Innovations LLC Supercritical fluid extraction apparatuses and methods for operating the same
WO2016118034A2 (fr) * 2015-01-19 2016-07-28 Patrascu Mariana Procédé et installation d'extraction de composés biologiquement actifs à partir de plantes et réacteur opérant en continu pour l'extraction assistée par micro-ondes et ultrasons desdits composés biologiquement actifs à partir de plantes
US20160318972A1 (en) * 2015-04-30 2016-11-03 Yang-Chang Wu Preparation method and analytic method for the extract of antrodia cinnamomea
WO2019169477A1 (fr) * 2018-03-09 2019-09-12 Mazza Innovation Ltd. Extraction par solvant sous pression de charges de biomasse végétale

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT202200026727A1 (it) 2022-12-23 2024-06-23 Piovan Spa Apparato e metodo per decontaminare materiale plastico

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IT201900020630A1 (it) 2021-05-08

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