EP3224236A1 - Procédé de précipitation d'acides aminés et/ou organiques à partir d'une charge complexe et particules d'acides aminés et/ou organiques pouvant ainsi être obtenues - Google Patents

Procédé de précipitation d'acides aminés et/ou organiques à partir d'une charge complexe et particules d'acides aminés et/ou organiques pouvant ainsi être obtenues

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Publication number
EP3224236A1
EP3224236A1 EP15801150.2A EP15801150A EP3224236A1 EP 3224236 A1 EP3224236 A1 EP 3224236A1 EP 15801150 A EP15801150 A EP 15801150A EP 3224236 A1 EP3224236 A1 EP 3224236A1
Authority
EP
European Patent Office
Prior art keywords
amino
solvent
organic acids
precipitation
mixture
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.)
Withdrawn
Application number
EP15801150.2A
Other languages
German (de)
English (en)
Inventor
Ruben Cornelis KOLFSCHOTEN
Johan Pieter Marinus Sanders
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.)
Wageningen Universiteit
Original Assignee
Wageningen Universiteit
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 Wageningen Universiteit filed Critical Wageningen Universiteit
Publication of EP3224236A1 publication Critical patent/EP3224236A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • C07C227/42—Crystallisation

Definitions

  • the present invention relates to a process for the precipitation of amino and/or organic acid- containing particles from a feed comprising amino and/or organic acids, to a process for the crystallization of amino and/or organic acids from a feed into amino and/or organic acid- containing particles, to amino and/or organic acid particles obtainable by the process and the use thereof in food or feed and chemical applications.
  • Proteins consist of 20 different amino acids of which 9 are 'essential' because monogastric organisms cannot synthesize these by their own.
  • the cost of feed for pigs and poultry can be lowered by adding amino acids that are the most limiting in cheap bulk protein sources such as corn flower, rape meal, sunflower meal etc.
  • Two amino acids, lysine and methionine have large application (1 million ton/ year) while threonine is fast growing product, now 100 000 tonnes and the number 4 is tryptophan which is small in volume (10 000 ton).
  • Tryptophan and the other essential amino acids are currently too expensive for animal (compound) feed application. Even if one of them would be available at low cost, the absence of the other would prevent their use in feed. Glutamic acid is also applied at large scale (> 1 Mton/year) as a taste enhancer in human food. Almost all 20 amino acids find an application as food ingredient for hospital or sport food, for special diets or as ingredient in flavour and fragrancy applications
  • Amino acids can also be used as building blocks for (bulk) chemical products. Their actual cost price, even of the 3 amino acids that are produced on large scale( lysine, methionine and glutamic acid that is used as a taste enhancer) is too high for the production of bulk chemicals.
  • amino and/or organic acids are produced by fermentation, by chemical synthesis and by extraction from proteins. Their purification is done by ion exchange or by precipitation from water in which the desired amino and/or organic acid is present in high concentration. Examples of such processes are disclosed in US2681927, US2605284, US2222993. These processes in general rely on precipitation processes as well as the addition of antisolvents. However, there is still a need for a more efficient and cost effective production of amino and/or organic acids and a need to isolate and separate amino and/or organic acids from mixtures of amino and/or organic acids and other complex starting compositions that contain amino and/or organic acids.
  • the present invention provides methods for achieving these and other goals and will lower the cost of production of most or all amino and/or organic acids.
  • the amino and/or organic acids provided by the invention can find their application in animal feed.
  • amino and/or organic acids provided by the invention can be used for chemical starting compounds, and thereby improve the economics of the separation from complex amino and/or organic acid mixtures.
  • the precipitated solid particles can be isolated and used as such or further processed.
  • the process can also be used for the selective removal of one or more amino and/or organic acids from a solution and the solution, depleted of one or more amino and/or organic acids, that can now be used or further processed.
  • the process is used to remove undesired amino and/or organic acids from the solution.
  • the solvent can be removed by passing (vapour of) the mixture through a zone that is capable of removing the solvent.
  • the anti-solvent can be added from an external source. This allows the amino and/or organic acids in the mixture to precipitate.
  • the invention relates to a process for the precipitation of one or more amino and/or organic acids from a (liquid) feed comprising a plurality of amino and/or organic acids, comprising the following steps:
  • the process is particular suitable to be used in a process for the isolation of amino and/or organic acid rich fractions of certain feeds to provide for amino and/or organic acid containing products that can be used in food or feed applications or in chemical applications (building blocks).
  • the process is particularly suited for a bulk process, i.e. in amounts of more than 1 , 10 or 100 kilos.
  • the invention also relates to a process wherein the amino
  • the invention also relates to a process wherein from the feed comprising amino and/or organic acids two or several amino and/or organic acids are crystallized simultaneously and each amino and/or organic acid is obtained/isolated in a relative pure form, i.e. substantially free (more than
  • the invention also pertains to a process for the crystallization of amino and/or organic acids from the amino and/or organic acid-containing particles of the invention comprising providing, in a precipitation vessel, a solution of the amino and/or organic acids from the amino and/or organic acid-containing particles;
  • a feed comprising a plurality of amino and/or organic acids.
  • the feed can be derived from Protamylasse, corn steep liquor, orange juice or its concentrate, grass juice, vinasse, molasses, beet juice, (sugar) cane juice, whey mother liquor, protein hydrolysates, fermentation broths and the like. Feeds can be used that originate from fermentation processes. The mother liquor resulting from the
  • the feed may contain a plurality of amino and/or organic acids and the relative amount of one amino and/or organic acid is at most 5%, 10%, 15% or 25% of the total amount of amino and/or organic acids in the feed.
  • the feed is preferably a bulk feed, i.e. the feed is at least 1 kilo, preferably at least 10 kilo, at least 100 kilo.
  • the feed is provided in the form of a solution, where necessary combined with a solvent to provide a solution of amino and/or organic acids from the feed in a precipitation vessel. It can be that no additional solvent is needed and that the feed is liquid enough to be used as such.
  • the solvent may be selectively removed and/or an anti-solvent is added. It may be that an anti- solvent is added prior to selectively removing the solvent.
  • An anti-solvent as used herein is a liquid in which the amino and/or organic acids have a lower solubility than in the solvent.
  • the amino and/or organic acids are insoluble or essentially insoluble (less than 0.1 g/dm 3 ) in the anti-solvent.
  • the solvent can be any solvent wherein amino and/or organic acids in the liquid feed dissolve or wherein at least part of the amino and/or organic acids in the liquid feed dissolve or remain in solution.
  • aqueous solvents i.e. mixtures of water and other solvents.
  • Aqueous solvents may also be acidic (having a pH between 1 -7) or basic (between 7-12) to impart different degrees of solubility to acidic and/or basic amino acids in the solution and hence allow selective crystallization of acidic and/or basic amino acids or in the case of organic acids to have the acids in (partly or completely) ionised form or non-ionised form.
  • the amino and/or organic acids of the liquid feed are provided in a mixture of a solvent and an anti-solvent.
  • the mixture is passed through, or brought into contact with, a zone that is capable of selectively removing the solvent.
  • This removal of the solvent can be in the vapour phase or in the liquid phase.
  • the vapour phase the vapour of the mixture can be led through a sorption zone wherein the sorption zone contains a solvent vapour sorbent to selectively absorb solvent from the vapour phase to yield a phase depleted in solvent (and possibly enriched in anti-solvent).
  • the solvent and the anti-solvent may have a different vapour pressure under the conditions employed, or a different boiling point or may form an azeotrope.
  • the solvent and the anti-solvent may have boiling point that differ from each other within a limited range to allow a vapour phase that contains both the solvent and the anti-solvent to be brought into the sorption zone.
  • the boiling point of the anti-solvent may be within 50 degrees Celsius of the boiling point of the solvent, preferably within 40 degrees Celsius, more preferably within 25 degrees Celsius.
  • Such a solvent vapour sorbent can be zeolites or molecular sieves, preferably with pores that are capable of selectively removing the solvent, such as for water with a minimum diameter of 3.0 to 3.5 Angstrom.
  • the sorbent has a lower affinity for the anti- solvent than for the solvent.
  • the vapour saturated sorbent may be regenerated by known techniques in the art, preferably by heating, for instance in a temperature range of from 120 degrees Celsius to 400 degrees Celsius.
  • the solvent can also be removed by providing as the zone a semi-permeable membrane that is permeable to the solvent, but is essentially impermeable to the anti-solvent and the rest of the mixture.
  • the solvent can also be removed by using a polymer such as polyethylene glycol (for instance PEG600) that is capable of forming a biphasic system wherein the PEG absorbs the solvent such as water after which the solvent in the PEG phase can be separated, for instance by a membrane processes from the crystallization vessel
  • a polymer such as polyethylene glycol (for instance PEG600) that is capable of forming a biphasic system wherein the PEG absorbs the solvent such as water after which the solvent in the PEG phase can be separated, for instance by a membrane processes from the crystallization vessel
  • the amount of anti-solvent that is absorbed by the sorbent or passes through the semi-permeable membrane is less than 20%, 10, 5 or 1 % of the amount of anti-solvent present in the system.
  • the amount of anti-solvent in the process can be as high as 90 vol%, preferably not more than 80 vol% drawn on the combined amount of solvent and anti-solvent but, if used, is at least 10 vol%, preferably at least 20 vol%. Preconcentration of the feed may aid in reducing the amount of anti-solvent needed to come to (selective) precipitation of amino and/or organic acids.
  • an anti-solvent gradient can be used wherein the anti-solvent is a mixture of two or more anti-solvents and when the anti-solvent is added, the composition of the anti-solvent is a gradient of the two or more anti-solvents.
  • the precipitation can be a multiple step process in which in each step different solvent/anti-solvent ratios are used to thereby selectively precipitate different amino and/or organic acids or groups of amino and/or organic acids.
  • the liquid passing through the semi-permeable membrane contains at least 95 vol% solvent (and consequently not more than 5 vol% anti-solvent). More preferably, the liquid contains at least 97 vol% and even more preferably at least 99 vol % solvent.
  • an anti-solvent to the mixture, preferably from an external source, before, after or independently form the removal of the solvent.
  • the removal of the solvent and /or the addition of anti-solvent results in a mixture that is depleted in solvent and increased in anti-solvent.
  • the removal of the solvent from the mixture increases the concentration of the amino and/or organic acids in solution in the mixture.
  • the saturation of the mixture is increased to the point of precipitation of the amino and/or organic acids.
  • the anti-solvent can be an alcohol with one, two, three, four, five or six carbon atoms, a diol such as glycol, or a triol such as glycerol or a polyol or a mixture thereof.
  • An alcohol with one, two, three or four carbon atoms can be methanol, ethanol, n-propanol, iso-propanol, n- butanol, iso-butanol, tert-butanol.
  • higher alcohols such as pentanols and hexanols
  • the anti-solvent can form a mixture with the solvent, i.e. the anti-solvent is miscible with the solvent in the conditions prevailing in the precipitation vessel.
  • the mixture depleted in solvent and with an increased concentration compared to the liquid feed is now allowed to precipitate in the form of solid particles comprising amino and/or organic acids in the precipitation vessel. This is preferably done at a precipitation
  • the mixture that has been provided with an increased concentration of amino and/or organic acids at an increased temperature may be cooled to enhance or speed up the precipitation process, although this is less economical from an energy perspective.
  • the precipitation process step is preferably performed under ambient (atmospheric) pressure. Nevertheless, in certain embodiments, a process under reduced pressure or with a carrier gas may be advantageously for the removal of the solvent and allow for lower temperatures to be used for the removal of the solvent. This can be advantageous as it may avoid detrimental heat effects on the mixture (deterioration of the feed).
  • the precipitation of the solid particles can be ab initio or can be aided by the addition of seeds to the mixture.
  • the seeds can be solid (even crystalline and/or individual) amino and/or organic acids, but can also be inert seeds. When the mixture comprising amino and/or organic acids is subjected to
  • the mixture may crystallise/solidify into amino and/or organic acid-containing particles of varying composition as the various amino and/or organic acids will have a different solubility in the mixture and hence crystallise at different rates and in different (mixed) compositions.
  • the precipitation is a selective precipitation and the precipitated solid particles that result from the precipitation are enriched in certain amino and/or organic acids and depleted in other amino and/or organic acids compared to the original composition of the liquid feed.
  • the precipitated amino acids are enriched or depleted in one or more of acidic, basic (alkaline), polar, apolar and special amino acids.
  • the whole process of the invention may be performed batch-wise, semi-continuously or continuously.
  • the solid amino and/or organic acid-containing particles may be crystalline or contain crystalline material. This may be crystalline amino and/or organic acids, but it may also be mixed crystals, co-crystallised amino and/or organic acids, organic acids, co-crystallized organic and amino acids, salts of amino and/or organic acids, polymorphs, solvates and hydrates of amino and/or organic acid (salts) as well as mixtures of these.
  • Solid particles that are not pure crystalline amino and/or organic acids can be further purified in additional process steps such a extraction, washing or recrystallization.
  • the recrystallization can be for instance by repeating the above process of the invention with another solvent and/or anti- solvent. Re-crystallization may also be performed after a subsequent step in which the amino and/or organic acid particles are fractionated for instance by wind sifting or other techniques.
  • the organic acids may be selected from amongst organic mono-acids, organic diacids and hydroxyacids.
  • the organic acids may be selected from amongst lactic acid, 3-hydroxy propanoic acid, hydroxy butyric acid, hydroxy-valeric acid, oxalic acid, succinic acid, adipic acid, pimelinic acid, formic acid, acetic acid, propionic acid, butyric acid, malic acid, fumaric acid, itaconic acid, citric acid and glycolic acid.
  • amino and/or organic acids implies only amino acids, only organic acids or a combination of amino and organic acids.
  • the amino acids can be any amino acid and are for instance selected from the group consisting of alanine, arginine, aspartic acid, asparagine, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine , leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, alpha-butyric acid, gamma-butyric acid, ornithine, taurine, betaine.
  • amino acids can be grouped in to essential and non-essential amino acids or grouped into aliphatic, hydroxylic/sulfuric/selenic, cyclic, aromatic, basic, acidic and amide amino acids or into polar and nonpolar amino acids as exemplified herein below.:
  • Essential histidine, isoleucine, leucine, lysine, methionine, phenylalanine, threonine, tryptophan, valine.
  • Nonessential alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, ornithine, proline, selenocysteine, serine, tyrosine.
  • Aliphatic alanine , glycine , isoleucine , leucine , proline , valine.
  • Aromatic - phenylalanine , tryptophan , tyrosine.
  • Acidic aspartic acid , glutamic acid Basic: arginine , histidine , lysine Hydroxylic: serine , threonine.
  • Sulphuric cysteine , methionine.
  • Amidic (containing amide group) asparagine , glutamine.
  • Most amino acids exist in two stereoisomers denoted as D or L.
  • the present invention focuses on amino acids obtained from natural sources which typically have an L-configuration. However, the invention may also relate to D-amino acids or mixtures of D and L.
  • Amino acids in their solid form, preferably crystalline form each have their own aqueous solubilities as indicated in the below table. Solubilities in other solvents (antisolvents) such as ethanol are described for instance in CRC Handbook of Chemistry and Physics 54 th ed., page C-724 as well as in Thomas Needham, Thesis 1970, Univ. Rhode Island.
  • the feed may be pre-treated by extraction of a fraction of amino acids (acidic, basic (alkaline), polar, apolar and special) or wherein the solution of amino acids is an extract of the liquid feed solution enriched or depleted in acidic, basic (alkaline), polar, apolar and special amino acids.
  • the feed may be pH adapted prior to the process of the present invention.
  • a process for the manufacturing of amino and/or organic acid-containing particles from a liquid feed comprising a plurality of amino and/or organic acids comprising the following steps:
  • the present invention relates also to the amino and/or organic acid- containing particles obtainable by the process of the invention and to the use of the amino and/or organic acid-containing particles of the processes if the present invention as food or feed ingredient.
  • GABA 34 39 0 10% 8 0 34%
  • Untreated protamylasse and ethanol were mixed on a weight base.
  • the figure shows the final ethanol concentration on the x-axis. Precipitation was observed.
  • the mixtures were centrifuged for 5 min at 10,000 rpm and 20°C and U-HPLC analysis of the amino acid composition of the remaining juice was performed.
  • the figure (Fig 1 ) shows calculated composition of precipitate grouped by amino acid type.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fodder In General (AREA)

Abstract

Cette invention concerne un procédé de précipitation d'un ou de plusieurs acides aminés et/ou organiques à partir d'une charge liquide comprenant une pluralité d'acides aminés et/ou organiques, comprenant l'introduction, dans une cuve de précipitation, d'une solution d'acides aminés et/ou organiques provenant de la charge dans un mélange de solvant et d'un anti-solvant ; le passage du mélange dans une zone capable d'éliminer sélectivement le solvant et/ou d'ajouter un anti-solvant à partir d'une source externe au mélange, pour obtenir un mélange appauvri en solvant et enrichi en anti-solvant, et accroître ainsi la concentration d'acides aminés et/ou organiques dans le mélange solvant/anti-solvant, permettant la précipitation de particules solides d'acides aminés et/ou organiques à partir du mélange solvant/anti-solvant dans la cuve de précipitation à une température de précipitation ; et le déchargement des particules solides d'acides aminés et/ou organiques ayant précipité de la cuve de précipitation.
EP15801150.2A 2014-11-25 2015-11-25 Procédé de précipitation d'acides aminés et/ou organiques à partir d'une charge complexe et particules d'acides aminés et/ou organiques pouvant ainsi être obtenues Withdrawn EP3224236A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14194769 2014-11-25
PCT/EP2015/077654 WO2016083455A1 (fr) 2014-11-25 2015-11-25 Procédé de précipitation d'acides aminés et/ou organiques à partir d'une charge complexe et particules d'acides aminés et/ou organiques pouvant ainsi être obtenues

Publications (1)

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EP3224236A1 true EP3224236A1 (fr) 2017-10-04

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EP15801150.2A Withdrawn EP3224236A1 (fr) 2014-11-25 2015-11-25 Procédé de précipitation d'acides aminés et/ou organiques à partir d'une charge complexe et particules d'acides aminés et/ou organiques pouvant ainsi être obtenues

Country Status (2)

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EP (1) EP3224236A1 (fr)
WO (1) WO2016083455A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019138338A1 (fr) 2018-01-09 2019-07-18 Universidade Do Porto Procédé de séparation et de purification de dérivés du glycérol
CN110079884B (zh) * 2019-05-08 2021-11-02 东华大学 一种高比表面积聚酰亚胺沉析纤维的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274728A1 (fr) * 1987-01-14 1988-07-20 Ajinomoto Co., Ltd. Procédé pour la purification de tryptophane
WO2013168077A1 (fr) * 2012-05-11 2013-11-14 Aker Process Systems As Élimination de sel d'acide carboxylique pendant la récupération d'un inhibiteur d'hydrate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2222993A (en) * 1938-05-07 1940-11-26 Lankenau Hospital Process of recovering amino acids
US2605284A (en) * 1946-09-09 1952-07-29 Stuart Company Process of separating crystalline amino acids mixtures from natural proteins
US2681927A (en) * 1951-05-04 1954-06-22 Research Corp Separation of amino acids
JP4361641B2 (ja) * 1999-06-29 2009-11-11 三菱レイヨン株式会社 光学活性アミノ酸と光学活性アミノ酸アミドの分離回収方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274728A1 (fr) * 1987-01-14 1988-07-20 Ajinomoto Co., Ltd. Procédé pour la purification de tryptophane
WO2013168077A1 (fr) * 2012-05-11 2013-11-14 Aker Process Systems As Élimination de sel d'acide carboxylique pendant la récupération d'un inhibiteur d'hydrate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2016083455A1 *

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