WO1997035489A1 - A process for obtaining phytic acid and lactic acid - Google Patents
A process for obtaining phytic acid and lactic acid Download PDFInfo
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- WO1997035489A1 WO1997035489A1 PCT/GB1997/000701 GB9700701W WO9735489A1 WO 1997035489 A1 WO1997035489 A1 WO 1997035489A1 GB 9700701 W GB9700701 W GB 9700701W WO 9735489 A1 WO9735489 A1 WO 9735489A1
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- Prior art keywords
- liquor
- acid
- lactic acid
- phytic acid
- solvent
- Prior art date
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 88
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 title claims abstract description 46
- 235000002949 phytic acid Nutrition 0.000 title claims abstract description 46
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000000467 phytic acid Substances 0.000 title claims abstract description 45
- 229940068041 phytic acid Drugs 0.000 title claims abstract description 45
- 239000004310 lactic acid Substances 0.000 title claims abstract description 44
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 238000000926 separation method Methods 0.000 claims abstract description 17
- 240000008042 Zea mays Species 0.000 claims abstract description 14
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims abstract description 14
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 14
- 235000005822 corn Nutrition 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 238000005191 phase separation Methods 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000012074 organic phase Substances 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 239000012141 concentrate Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/14—Vegetable proteins
-
- 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Definitions
- the present invention relates to a process for the selective separation of an acid selected from the group consisting of phytic acid, lactic acid, and mixtures thereof from corn steep liquor containing the same.
- Corn steep liquors (CSL), a by-product of the corn milling industry, contain a very large number of constituents, including relatively high amounts of lactic acid and phytic acid. These acids present considerable commercial interest, and so would their recovery from CSL, if it were achievable at low cost. It is the purpose of the present invention to provide effective procedures for the recovery of lactic acid and phytic acid from CSL.
- a typical CSL is a viscous solution of about 50% solids with a lactic acid content ranging from 15% to 25% of the solids, and a phytic acid content of about 8% of the solids. It is important to stress that the expression of these contents in terms of acids is a form of stating the results of analytical determinations, and does not imply that the acids are present in CSL as such, i.e., as free acids. In fact, the pH of CSL ranges from 3.9 to 4.2, which would rather indicate a high content of phytates and lactates. The remainder of CSL solids, some 2/3 of the total, consists of inorganic ions, amino acids and peptides, carbohydrates, and numerous trace constituents.
- the purpose of the present invention is to recover concentrates containing as a preponderant component lactic acid, phytic acid, or both, from CSL containing the same, said concentrates lending themselves to efficient isolation of the acid or acids contained therein, which may or may not be in free acid form, but which products for purposes of simplicity of identification will hereinafter be referred to as lactic acid and phytic acid, since the same can be readily be recovered therefrom.
- a concentrate is defined as a material that contains, on a solvent-free basis, not less than 50% lactic acid, phytic acid, or both.
- the recovery of concentrates thus constitutes an inversion of the ratios of the desired acids to other solids from about 1 :3 to below 1 : 1 for lactic acid, and from about 1 :7 to below 1 : 1 for phytic acid.
- selected modes of concentrate recovery can provide ratios better than 10: 1 of phytic acid and lactic acid to other CSL components.
- the recovery of phytic acid and lactic acid concentrates from CSL also provides an important increase in the nutritional value of the remainder.
- these two acids respectively are of no, and of limited, nutritional value; the remainder is then constituted mainly of the nutritionally valuable nitrogen componds and is thus more valuable than the CSL prior to the recovery of phytic acid and lactic acid.
- alkanols when admixed with CSL, exert marked selectivities with respect to lactic acid and to phytic acid, and do so in opposite fashions: solvent power with respect to lactic acid and non-solvent power with respect to phytic acid, resulting in extraction capabilities with respect to the former and precipitation capabilities with respect to the latter.
- CSL alkanol mixtures Another surprising characteristic of CSL alkanol mixtures is that alkanols having at least 3 carbon atoms, which are per se completely water-miscible (specifically, n-propanol, sec-propanol, ter-butanol), separate into an aqueous phase and an organic phase and thus provide unexpected choices for solvent extraction. It was further found that CSL alkanol systems are operationally effective, as even a modest content of an alkanol in CSL greatly increases its fluidity, which in turn provides for easy separation of solid precipitates as well as for clean separation of an organic phase.
- alkanols can be modified by the inclusion of fatty amines without loss of the beneficial operational characteristics that they confer, which contrasts strongly with the visous emulsions that tend to form when the usual amine extractants are applied to CSL.
- amine modified alkanols the amines are at their maximum strength, whereby recoveries of lactic acid and phytic acid lend themselves to a variety of manipulations so as to fit effectively particular situations.
- said solvent can also contain additional components such as minor amounts, e.g. up to 20%, of hydrocarbons in order to better control the water miscibility of the alkanols and minor amounts of amines to lend basic properties to the alkanolic solvent.
- a process for the selective separation of phytic acid from corn steep liquor containing the same comprising combining said liquor with a solvent comprising at least one C -
- a process for the selective separation of lactic acid from corn steep liquor containing the same comprising combining said liquor with a solvent comprising at least one C3-C8 alkanol, whereby an alkanolic organic phase is formed containing at least a major portion of the lactic acid originally contained in said liquor.
- a solvent which contains up to 50% of a fatty amine having at least 18 carbon atoms comprising combining said liquor with a solvent comprising at least one C-
- a process for the selective separation of both phytic acid and lactic acid from corn steep liquor containing the same comprising combining said liquor with a solvent comprising at least one C-
- Example 1 100 g of the same CSL used in Example 1 was mixed at room temperature with 45 g of n-propanol (nPrOH), whereby the CSL became saturated with this alkanol, as evidenced by the separation of a small organic phase; the treated CSL, which became quite fluid, was extracted counter-current in four stages, with 25 g of nPrOH.
- the extract on drying, left a residue of 1 5.3 g; 9.5 g thereof was analysed as lactic acid.
- the extract in Example 2 is the concentrate as defined. On a solvent-free basis, it contained about 86% of the lactic acid in the extracted CSL, at a concentration of 62%.
- Example 4 indicates a way for its complete recovery, with the recovery of a lactic acid concentrate as a desirable co-product.
- Example 3 The procedure of Example 3 was followed, and the aqueous phase separated from the butanolic phase was contacted with a solution of 30 g of tridodecylamine in 30 g of secBuOH; the organic phase was found to contain 5.8 g solids of 95% in lactic acid.
- Example 4 teaches that virtually complete recovery of lactic acid is achievable as high grade concentrate in amine-containing alkanols.
- EXAMPLE 5
- Example 2 100 g CSL, of the same composition as used in Example 1 , were contacted counter-current with an extractant made of 1 10 g nPrOH and 33 g tridodecylamine, in five stages.
- the extracted aqueous phase contained less than 1 % lactic acid and only traces of phytic acid.
- the phytic acid was 25% and lactic acid was 68.5%.
- Example 5 illustrates several interesting features of the present invention. It is possible to recover the phytic acid alongside the lactic acid, if a fatty amine is added to the alkanol used, and the amount of amine used can be well below the molar equivalent to the acid extracted. Thus, in the present example, there are 122 mmol of lactic acid and 6 mmol of phytic acid, a total of 128 mmol; the amine is present in less than 63 mmol. This is in sharp contrast with known extractions of acids by amines (e.g., that of U.S. Patent 4,275,234), which require at least an equivalent amount of amine. This low usage of amine can only facilitate further treatment of the 93.5% concentrate described in Example 5.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention provides a process for the selective separation of an acid selected from the group consisting of phytic acid, lactic acid, and mixtures thereof, from corn steep liquor containing the same, comprising combining the liquor with a solvent comprising at least one C1-C8 alkanol, whereby phase separation of at least a major portion of the desired acid from the liquor is achieved.
Description
A PROCESS FOR OBTAINING PHYTIC ACID AND LACTIC ACID
The present invention relates to a process for the selective separation of an acid selected from the group consisting of phytic acid, lactic acid, and mixtures thereof from corn steep liquor containing the same.
Corn steep liquors (CSL), a by-product of the corn milling industry, contain a very large number of constituents, including relatively high amounts of lactic acid and phytic acid. These acids present considerable commercial interest, and so would their recovery from CSL, if it were achievable at low cost. It is the purpose of the present invention to provide effective procedures for the recovery of lactic acid and phytic acid from CSL.
A typical CSL is a viscous solution of about 50% solids with a lactic acid content ranging from 15% to 25% of the solids, and a phytic acid content of about 8% of the solids. It is important to stress that the expression of these contents in terms of acids is a form of stating the results of analytical determinations, and does not imply that the acids are present in CSL as such, i.e., as free acids. In fact, the pH of CSL ranges from 3.9 to 4.2, which would rather indicate a high content of phytates and lactates. The remainder of CSL solids, some 2/3 of the total, consists of inorganic ions, amino acids and peptides, carbohydrates, and numerous trace constituents.
In spite of the low cost of CSL, large scale commercial recovery of lactic acid and phytic acid has not been established. U.S. Patent 5, 248,804 describes recovery by means of ion-exchange. Such recovery requires prior dilution by water, which subsequently imposes an onerous reconcentration of the residue as well as the consumption of chemical reagents and the production of abundant wash liquors, which need to be disposed of. It is obvious that similar difficulties attach to other known separation methods if applied to CSL directly, due to CSL's high concentration in solutes other than the desired ones and the multiplicity of components that need to be separated from the desired products.
The purpose of the present invention is to recover concentrates containing as a preponderant component lactic acid, phytic acid, or both, from CSL containing the same, said concentrates lending themselves to efficient isolation of the acid or acids contained therein, which may or may not be in free acid form, but which products for purposes of simplicity of identification will hereinafter be referred to as lactic acid and phytic acid, since the same can be readily be recovered therefrom.
For the purposes of the present invention, a "concentrate" is defined as a material that contains, on a solvent-free basis, not less than 50% lactic acid, phytic acid, or both.
The recovery of concentrates thus constitutes an inversion of the ratios of the desired acids to other solids from about 1 :3 to below 1 : 1 for lactic acid, and from about 1 :7 to below 1 : 1 for phytic acid. As illustrated further below, selected modes of concentrate recovery can provide ratios better than 10: 1 of phytic acid and lactic acid to other CSL components.
The recovery of phytic acid and lactic acid concentrates from CSL also provides an important increase in the nutritional value of the remainder. In fact, these two acids respectively are of no, and of limited, nutritional value; the remainder is then constituted mainly of the nutritionally valuable nitrogen componds and is thus more valuable than the CSL prior to the recovery of phytic acid and lactic acid.
It was surprisingly found that alkanols, when admixed with CSL, exert marked selectivities with respect to lactic acid and to phytic acid, and do so in opposite fashions: solvent power with respect to lactic acid and non-solvent power with respect to phytic acid, resulting in extraction capabilities with respect to the former and precipitation capabilities with respect to the latter.
Another surprising characteristic of CSL alkanol mixtures is that alkanols having at least 3 carbon atoms, which are per se completely water-miscible (specifically, n-propanol, sec-propanol, ter-butanol), separate into an aqueous phase and an organic phase and thus provide unexpected choices for solvent extraction.
It was further found that CSL alkanol systems are operationally effective, as even a modest content of an alkanol in CSL greatly increases its fluidity, which in turn provides for easy separation of solid precipitates as well as for clean separation of an organic phase.
It was still further found that alkanols can be modified by the inclusion of fatty amines without loss of the beneficial operational characteristics that they confer, which contrasts strongly with the visous emulsions that tend to form when the usual amine extractants are applied to CSL. In amine modified alkanols, the amines are at their maximum strength, whereby recoveries of lactic acid and phytic acid lend themselves to a variety of manipulations so as to fit effectively particular situations.
Thus, according to the present invention, there is now provided a process for the selective separation of an acid selected from the group consisting of phytic acid, lactic acid, and mixtures thereof, from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C-| -Cs alkanol, whereby phase separation of at least a major portion of the desired acid from said liquor is achieved.
Preferably, said solvent can also contain additional components such as minor amounts, e.g. up to 20%, of hydrocarbons in order to
better control the water miscibility of the alkanols and minor amounts of amines to lend basic properties to the alkanolic solvent.
In a first preferred embodiment of the invention, there is provided a process for the selective separation of phytic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C -| -C8 alkanol, whereby a precipitate is formed containing at least a major portion of the phytic acid originally contained in said liquor.
Preferably, in said embodiment, there is formed a precipitate containing at least 90% of the phytic acid originally contained in said liquor.
In a second preferred embodiment of the invention, there is provided a process for the selective separation of lactic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C3-C8 alkanol, whereby an alkanolic organic phase is formed containing at least a major portion of the lactic acid originally contained in said liquor.
As will be illustrated in the Examples hereinafter, in said second embodiment, especially preferred results are obtained by using a solvent which contains up to 50% of a fatty amine having at least 18 carbon atoms.
In yet a third embodiment of the present invention, there is provided a process for the selective separation of both phytic acid and lactic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C-| -Cg alkanol, whereby a precipitate is formed containing at least a major portion of the phytic acid originally contained in said liquor, and an alkanolic organic phase is formed containing at least a minor portion of the lactic acid originally contained in said liquor.
In a fourth embodiment of the present invention, there is provided a process for the selective separation of both phytic acid and lactic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C-| -C8 alkanol and a fatty amine having at least 1 8 carbon atoms, whereby an alkanolic organic phase is formed containing at least a major portion of both the lactic acid and phytic acid originally contained in said liquor.
While the invention will now be described in connection with certain preferred embodiments in the following examples so that aspects thereof may be more fully understood and appreciated, it is not intended to limit the invention to these particular embodiments. On the contrary, it is intended to cover all alternatives, modifications and equivalents as may be included within the scope of the invention as defined by the appended claims. Thus, the following examples which include preferred embodiments will serve to illustrate the
practice of this invention, it being understood that the particulars shown are by way of example and for purposes of illustrative discussion of preferred embodiments of the present invention only and are presented in the cause of providing what is believed to be the most useful and readily understood description of formulation procedures as well as of the principles and conceptual aspects of the invention.
EXAMPLE 1
100 g CSL, containing 50% solids, 1 1 % lactic acid (22% on a solid basis) and 4% phytic acid (8% on a solid basis) were mixed with 200 g 95 % ethanol. The precipitate that formed was separated by centrifugations; after drying, it contained 56% phytic acid. The ethanol recovered by distillation was 95 %; the concentration of the extracted CSL was practically unchanged, and its phytic acid content practically zero.
EXAMPLE 2
100 g of the same CSL used in Example 1 was mixed at room temperature with 45 g of n-propanol (nPrOH), whereby the CSL became saturated with this alkanol, as evidenced by the separation of a small organic phase; the treated CSL, which became quite fluid, was extracted counter-current in four stages, with 25 g of nPrOH. The extract, on drying, left a residue of 1 5.3 g; 9.5 g thereof was analysed as lactic acid.
The extract in Example 2 is the concentrate as defined. On a solvent-free basis, it contained about 86% of the lactic acid in the extracted CSL, at a concentration of 62%.
EXAMPLE 3
1 5 g of secBuOH and 100 g CSL of the same composition as used in Example 1 , were mixed and heated to about 100dC to ensure complete dissolution of the alkanol. The solids that separated were collected by centrifugation; after drying, they weighed 5.7 g and contained 70% phytic acid. The clarified liquor was cooled to room temperature, whereupon 1 9 g of an alkanolic phase separated therefrom, containing 6.1 g solids of 87% concentration in lactic acid.
In Example 3, secBuOH is used to induce the precipitation of phytic acid, similar to the use of EtOH in Example 1 . However, the limited solubility of the higher alkanol in CSL required heating to dissolve enough of it to induce the desired precipitation; this amount was still much lower than the amount of ethanol required to achieve a similar precipitation. The probable explanation is that this is due to the lower hydrophilic character of secBuOH compared to EtOH. The recovery of phytic acid in the solid concentrate, computing to 3.99 g, was virtually complete.
The organic phase that separated on cooling constituted a concentrate containing about 48% of the lactic acid in the CSL. Thus, if phytic acid is the main product of interest, Example 4 indicates a way for its complete recovery, with the recovery of a lactic acid concentrate as a desirable co-product.
EXAMPLE 4
The procedure of Example 3 was followed, and the aqueous phase separated from the butanolic phase was contacted with a solution of 30 g of tridodecylamine in 30 g of secBuOH; the organic phase was found to contain 5.8 g solids of 95% in lactic acid.
Example 4 teaches that virtually complete recovery of lactic acid is achievable as high grade concentrate in amine-containing alkanols.
EXAMPLE 5
100 g CSL, of the same composition as used in Example 1 , were contacted counter-current with an extractant made of 1 10 g nPrOH and 33 g tridodecylamine, in five stages. The extracted aqueous phase contained less than 1 % lactic acid and only traces of phytic acid. In the organic phase, on a solvent-free basis, the phytic acid was 25% and lactic acid was 68.5%.
Example 5 illustrates several interesting features of the present invention. It is possible to recover the phytic acid alongside the lactic acid, if a fatty amine is added to the alkanol used, and the amount of amine used can be well below the molar equivalent to the acid extracted. Thus, in the present example, there are 122 mmol of lactic acid and 6 mmol of phytic acid, a total of 128 mmol; the amine is present in less than 63 mmol. This is in sharp contrast with known extractions of acids by amines (e.g., that of U.S. Patent 4,275,234), which require at least an equivalent amount of amine. This low usage of amine can only facilitate further treatment of the 93.5% concentrate described in Example 5.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative examples and that the present invention may be embodied in other specific forms without departing from the essential attributes thereof, and it is
therefore desired that the present embodiments and examples be considered in all respects as illustrative and not restrictive, reference being made to the appended claims, rather than to the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims
1 . A process for the selective separation of an acid selected from the group consisting of phytic acid, lactic acid, and mixtures thereof, from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C-| -C8 alkanol, whereby phase separation of at least a major portion of the desired acid from said liquor is achieved.
2. A process according to claim 1 for the selective separation of phytic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C-i -Cg alkanol, whereby a precipitate is formed containing at least a major portion of the phytic acid originally contained in said liquor.
3. A process according to claim 2, wherein there is formed a precipitate containing at least 90% of the phytic acid originally contained in said liquor.
4. A process according to claim 2, wherein said precipitate is recovered by centrifugation and drying.
5. A process according to claim 1 for the selective separation of lactic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C3-C8 alkanol, whereby an alkanolic organic phase is formed containing at least a major portion of the lactic acid originally contained in said liquor.
6. A process according to claim 5, wherein said solvent contains up to 50% of a fatty amine having at least 1 8 carbon atoms.
7. A process according to claim 5, wherein said selective separation is achieved by repeated counter-current extraction between said liquor and said solvent.
8. A process according to claim 1 , for the selective separation of both phytic acid and lactic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C-| -C8 alkanol, whereby a precipitate is formed containing at least a major portion of the phytic acid originally contained in said liquor, and an alkanolic organic phase is formed containing at least a minor portion of the lactic acid originally contained in said liquor.
9. A process according to claim 1 , for the selective separation of both phytic acid and lactic acid from corn steep liquor containing the same, comprising combining said liquor with a solvent comprising at least one C -| -C8 alkanol and a fatty amine having at least 1 8 carbon atoms, whereby an alkanolic organic phase is formed containing at least a major portion of both the lactic acid and phytic acid originally contained in said liquor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU20328/97A AU2032897A (en) | 1996-03-27 | 1997-03-13 | A process for obtaining phytic acid and lactic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL117679 | 1996-03-27 | ||
| IL11767996A IL117679A0 (en) | 1996-03-27 | 1996-03-27 | A process for obtaining phytic acid and lactic acid |
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| Publication Number | Publication Date |
|---|---|
| WO1997035489A1 true WO1997035489A1 (en) | 1997-10-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1997/000701 WO1997035489A1 (en) | 1996-03-27 | 1997-03-13 | A process for obtaining phytic acid and lactic acid |
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| Country | Link |
|---|---|
| AU (1) | AU2032897A (en) |
| IL (1) | IL117679A0 (en) |
| WO (1) | WO1997035489A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6229046B1 (en) | 1997-10-14 | 2001-05-08 | Cargill, Incorported | Lactic acid processing methods arrangements and products |
| US6475759B1 (en) | 1997-10-14 | 2002-11-05 | Cargill, Inc. | Low PH lactic acid fermentation |
| CN101838287A (en) * | 2010-05-27 | 2010-09-22 | 合肥工业大学 | Method for circularly extracting phytic acid from lactic acid assisted by ultrasonic waves |
| WO2012055997A1 (en) | 2010-10-28 | 2012-05-03 | Total S.A. | Process for polylactic acid production using monascus |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410929A (en) * | 1965-06-08 | 1968-11-12 | Corn Products Co | Recovery of phytates from steepwater |
| US4275234A (en) * | 1972-06-19 | 1981-06-23 | Imi (Tami) Institute For Research And Development | Recovery of acids from aqueous solutions |
| JPS6058993A (en) * | 1983-09-09 | 1985-04-05 | Kanemi Soko Kk | Method for separating phytin concentrate from rice bran |
| JPS6128396A (en) * | 1984-06-22 | 1986-02-08 | Oji Koonsutaac Kk | Preparation of lactate |
| WO1992016534A1 (en) * | 1991-03-14 | 1992-10-01 | Reilly Industries, Inc. | Recovery of phytic and/or lactic acid and direct retrieval of inositol |
| US5248804A (en) * | 1992-12-08 | 1993-09-28 | Abbott Laboratories | Separation of phytate from plant protein using ion exchange |
| WO1995003268A1 (en) * | 1993-07-26 | 1995-02-02 | A.E. Staley Manufacturing Company | Process for recovering organic acids |
-
1996
- 1996-03-27 IL IL11767996A patent/IL117679A0/en unknown
-
1997
- 1997-03-13 WO PCT/GB1997/000701 patent/WO1997035489A1/en active Application Filing
- 1997-03-13 AU AU20328/97A patent/AU2032897A/en not_active Abandoned
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410929A (en) * | 1965-06-08 | 1968-11-12 | Corn Products Co | Recovery of phytates from steepwater |
| US4275234A (en) * | 1972-06-19 | 1981-06-23 | Imi (Tami) Institute For Research And Development | Recovery of acids from aqueous solutions |
| JPS6058993A (en) * | 1983-09-09 | 1985-04-05 | Kanemi Soko Kk | Method for separating phytin concentrate from rice bran |
| JPS6128396A (en) * | 1984-06-22 | 1986-02-08 | Oji Koonsutaac Kk | Preparation of lactate |
| WO1992016534A1 (en) * | 1991-03-14 | 1992-10-01 | Reilly Industries, Inc. | Recovery of phytic and/or lactic acid and direct retrieval of inositol |
| US5248804A (en) * | 1992-12-08 | 1993-09-28 | Abbott Laboratories | Separation of phytate from plant protein using ion exchange |
| WO1995003268A1 (en) * | 1993-07-26 | 1995-02-02 | A.E. Staley Manufacturing Company | Process for recovering organic acids |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE WPI Section Ch Week 8521, Derwent World Patents Index; Class E11, AN 85-124700, XP002031693 * |
| DATABASE WPI Section Ch Week 8612, Derwent World Patents Index; Class D16, AN 86-079051, XP002031692 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6229046B1 (en) | 1997-10-14 | 2001-05-08 | Cargill, Incorported | Lactic acid processing methods arrangements and products |
| US6320077B1 (en) | 1997-10-14 | 2001-11-20 | Cargill, Incorporated | Lactic acid processing; methods; arrangements; and, product |
| US6475759B1 (en) | 1997-10-14 | 2002-11-05 | Cargill, Inc. | Low PH lactic acid fermentation |
| US6534679B2 (en) | 1997-10-14 | 2003-03-18 | Cargill, Incorporated | Lactic acid processing; methods; arrangements; and, products |
| US7144977B2 (en) | 1997-10-14 | 2006-12-05 | Cargill, Incorporated | Lactic acid processing; methods; arrangements; and, products |
| CN101838287A (en) * | 2010-05-27 | 2010-09-22 | 合肥工业大学 | Method for circularly extracting phytic acid from lactic acid assisted by ultrasonic waves |
| CN101838287B (en) * | 2010-05-27 | 2012-07-04 | 合肥工业大学 | Method for circularly extracting phytic acid from lactic acid assisted by ultrasonic waves |
| WO2012055997A1 (en) | 2010-10-28 | 2012-05-03 | Total S.A. | Process for polylactic acid production using monascus |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2032897A (en) | 1997-10-17 |
| IL117679A0 (en) | 1996-07-23 |
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