Method and system for preparing lysed lecithin

Abstract

The present invention relates to methods and systems for producing lysed lecithin, such as continuous methods. The methods can include contacting a lecithin-containing stream with a hydrolyzing agent. The stream can then be heated and / or mixed to form an emulsion, which can improve the efficiency of the method.

Description

Background Technology

[0001] Lecithin is widely used in various industries, including animal feed and the food industry (see, for example, Lister, GR (List, GR), Polar Lipids, 2015: 1-33). Lysophosphatidylcholine comprises a hydrolyzed version of lecithin and can have better emulsifying properties than lecithin. Therefore, in the feed industry, lysophosphatidylcholine can replace more fat in feed formulations (see, for example, Brautigan, DL (Brautigan, DL et al.), Poultry Science, 2017, 96(8): 2889-2898). Lysophosphatidylcholine can significantly improve animal growth performance and increase nutrient absorption and utilization. In the food industry, lysophosphatidylcholine is used in dairy products and baked goods, likely due to its excellent emulsifying ability. Lysophosphatidylcholine can also be used in many other fields, including but not limited to pharmaceuticals, cosmetics, and bioengineering (see, for example, Iwasaki, Y. et al., Lipid Biotechnology, 2002: 417-431). Although phosphatidylcholine (PC) is the main component of lecithin, it can be converted into a hydrolyzed form in lysophosphatidylcholine, which is called lysophosphatidylcholine (LPC).

[0002] Lysophosphatidylcholine is typically synthesized in a reactor by mixing lecithin, water, and phospholipases A1, A2, or B under constant stirring / mixing (see, for example, Joshi, A., *European Journal of Lipid Science and Technology*, 2006, 108(4): 363-373). To control conversion, the reaction typically requires 6 to 48 hours. When the desired LPC content is reached, the reaction is usually inactivated by heating to 95°C, followed by drying on a membrane evaporator to obtain the final lysophosphatidylcholine product. Lysophosphatidylcholine products used in feed and food typically have an LPC content ranging from 3% to 8%.

[0003] While continuous reactions are extremely common in the chemical synthesis industry, applying continuous synthesis processes to lecithin feedstocks has been a challenge for one or more reasons. For example, lecithin feedstocks typically have high viscosity; therefore, they can be difficult to transport in system components such as piping, particularly smoothly and / or at a constant rate. As another example, lecithin can become a non-Newtonian fluid when mixed with water (see, for example, Zhang, K. et al., *European Journal of Lipid Science and Technology*, 2012, 114(11): 1254-1260), which can make its fluid characteristics unpredictable. Furthermore, the lecithin industry typically processes hundreds of tons of lecithin per day; therefore, finding a suitable-sized continuous reactor, especially with long reaction times such as approximately 6 hours to approximately 48 hours, is difficult, if not impossible.

[0004] There is still a need for improved methods for producing lysophosphatidylcholine, including continuous methods and / or methods that are more efficient, reduce the possibility of overreaction, require less space, or have a combination of the above advantages. Summary of the Invention

[0005] This document provides examples of methods (including continuous methods) for producing lysophosphatidylcholine, which can be more efficient and / or cheaper than known methods for producing lysophosphatidylcholine. For example, embodiments of the methods described herein may require relatively short production cycle times and / or occupy relatively small spaces.

[0006] In one aspect, a method for producing a product is provided, wherein the method may be a continuous method. In some embodiments, the method includes: providing a first stream comprising lecithin and water, wherein the water is present in the first stream at a concentration of about 10 wt% to about 300 wt% based on the weight of the lecithin; contacting the first stream with a hydrolyzing agent to form a second stream, wherein the hydrolyzing agent can effectively promote the hydrolysis reaction of the lecithin; subjecting the second stream to heating, mixing, or a combination thereof for a sustained and effective period to form a third stream comprising an emulsion; and subjecting the third stream to heating, mixing, or a combination thereof for a sustained and effective period to drive the hydrolysis reaction at a desired rate, desired extent, or combination thereof to convert at least a portion of the lecithin into a product. The product may include lysophosphatidylcholine.

[0007] In another aspect, a system for producing a product is provided. In some embodiments, the system includes a mixer and a reactor, wherein the mixer and the reactor are in fluid communication. The mixture may be a static mixer or a dynamic mixer. The system may also include one or more other components known in the art, such as pumps. The system can be used to perform any of the methods disclosed herein, either fully or partially.

[0008] Further aspects will be set forth in part in the description which follows, and in part will be apparent from the description, or may be learned by practice of the aspects described herein. The advantages described herein can be realized and obtained by means of the elements and combinations particularly pointed out in the appended claims. It should be understood that the foregoing general description and the following detailed description are merely exemplary and explanatory, and not restrictive. Attached Figure Description

[0009] Figure 1 This is a schematic diagram depicting elements of an embodiment of a continuous method and system for producing lysophosphatidylcholine.

[0010] Figure 2A The effect of enzyme amount on lysophosphatidylcholine conversion rate observed during testing of embodiments of the methods provided herein is depicted.

[0011] Figure 2B The effect of moisture on lysophosphatidylcholine conversion rate is depicted during testing of embodiments of the methods provided herein.

[0012] Figure 2C The effect of reaction time on lysophosphatidylcholine conversion rate is depicted during testing of embodiments of the methods provided herein.

[0013] Figure 2D The effect of reaction temperature on lysophosphatidylcholine conversion rate is depicted during testing of embodiments of the methods provided herein.

[0014] Figure 2E The effect of emulsification time on lysophosphatidylcholine conversion rate is depicted during testing of embodiments of the methods provided herein.

[0015] Figure 3A The effects of enzyme levels on phosphatidylcholine (PC) and lysophosphatidylcholine (LPC) levels observed during testing of embodiments of the methods provided herein are depicted.

[0016] Figure 3B The effect of moisture on PC and LPC content is depicted during testing in embodiments of the methods provided herein.

[0017] Figure 3CThe effect of reaction time on PC and LPC content observed during testing of embodiments of the methods provided herein is depicted.

[0018] Figure 3D The effect of reaction temperature on PC and LPC content observed during testing in embodiments of the methods provided herein is depicted.

[0019] Figure 3E The effect of emulsification time on PC and LPC content observed during testing of embodiments of the methods provided herein is depicted. Detailed Implementation

[0020] This document provides methods and systems for producing a product. In some embodiments, the product includes lysophosphatidylcholine.

[0021] In some embodiments, the methods provided herein are continuous methods. The methods may be performed continuously for one or more reasons, such as (i) the formation of an emulsion that is relatively easy to handle, for example, for transport between components of a system, (ii) a relatively fast reaction time, or (iii) a combination of (i) and (ii).

[0022] In some embodiments, the method includes providing a first feed stream comprising lecithin and water. Water may be present in the first feed stream in any amount that does not undesirably affect one or more embodiments of the method provided herein. In some embodiments, water is present in the first feed stream at a concentration of about 10 wt% to about 300 wt%, about 10 wt% to about 250 wt%, about 10 wt% to about 200 wt%, about 10 wt% to about 150 wt%, about 10 wt% to about 100 wt%, about 10 wt% to about 50 wt%, about 20 wt% to about 40 wt%, about 25 wt% to about 35 wt%, about 50 wt% to about 300 wt%, about 100 wt% to about 300 wt%, about 150 wt% to about 300 wt%, about 200 wt% to about 300 wt%, or about 250 wt% to about 300 wt%, based on the weight of lecithin. Any known technique can be used to change (e.g., reduce) the amount of water in the first stream, and the change in water amount can be made before or after the first stream comes into contact with the hydrolysant.

[0023] In some embodiments, the methods provided herein include contacting a first stream with a hydrolyzing agent to form a second stream. Any amount of hydrolyzing agent may be used in the methods herein, such as any amount that will not undesirably affect one or more embodiments provided herein. In some embodiments, the hydrolysant is present in the second feed stream at concentrations relative to lecithin of about 10 ppm to about 1,500 ppm, about 10 ppm to about 1,250 ppm, about 10 ppm to about 1,000 ppm, about 10 ppm to about 750 ppm, about 10 ppm to about 500 ppm, about 10 ppm to about 300 ppm, about 10 ppm to about 200 ppm, about 10 ppm to about 100 ppm, about 10 ppm to about 50 ppm, about 100 ppm to about 1,500 ppm, about 200 ppm to about 1,500 ppm, about 300 ppm to about 1,500 ppm, about 500 ppm to about 1,500 ppm, about 750 ppm to about 1,500 ppm, about 750 ppm to about 1,250 ppm, or about 750 ppm to about 1,000 ppm. However, other concentrations may be used.

[0024] In some embodiments, the method includes subjecting a second stream to heating, mixing, or a combination thereof for a period of time to effectively form a third stream comprising an emulsion. The emulsion may be a homogeneous emulsion. The emulsion may be a Newtonian fluid. Without wishing to be bound by any particular theory, it is believed that the features of the embodiments of the emulsions herein allow the emulsions to be handled (e.g., transported) more easily than intermediate streams produced in existing processes. Therefore, the formation of the embodiments of the emulsions herein allows embodiments of the methods provided herein to be effective and / or efficient continuous methods.

[0025] The effective formation time of the third stream comprising the emulsion can be relatively short, which facilitates and / or makes it easy to perform embodiments of the methods provided herein in a continuous manner. In some embodiments, the effective formation time of the third stream comprising the emulsion is from about 1 minute to about 10 minutes, from about 1 minute to about 8 minutes, from about 1 minute to about 5 minutes, from about 2 minutes to about 4 minutes, from about 2.5 minutes to about 3.5 minutes, from about 3 minutes, or from about 1 minute to about 3 minutes.

[0026] Generally, any two or more elements of the method provided herein can be performed (i) in any order, (ii) entirely or partially simultaneously, (iii) sequentially, or (iv) in combination thereof. For example, hypothetical element "A" and hypothetical element "B" can be performed in any of the following ways: (i) element "A" begins and completes, and then element "B" begins and completes; (ii) element "B" begins and completes, and then element "A" begins and completes; (iii) elements "A" and "B" begin and complete simultaneously; (iv) element "A" begins, element "B" begins, element "A" completes, and then element "B" completes; (v) element "B" begins, element "A" begins, element "A" completes, and then element "B" completes, etc. In some embodiments, contacting the first stream with the hydrolysate and subjecting the second stream to heating, mixing, or a combination thereof are performed simultaneously or sequentially.

[0027] Generally, any element of the method provided herein can be performed using and / or in any known apparatus. In some embodiments, contact between the first feed stream and the hydrolysant takes place at least partially in a first reservoir or a first mixing apparatus. In some embodiments, contact between the first feed stream and the hydrolysant includes conveying the first feed stream to the first reservoir or the first mixing apparatus, and conveying the hydrolysant to the first reservoir or the first mixing apparatus. Any known apparatus, such as a pump, can be used to convey the feed stream. In some embodiments, a screw pump is used to convey the first feed stream. In some embodiments, a peristaltic pump is used to convey the hydrolysant.

[0028] In some embodiments, the second stream is subjected to heating, mixing, or a combination thereof at least partially in the first reservoir, the first mixing device, or a combination thereof. In some embodiments, contacting the first stream with a hydrolysate to form the second stream occurs before the second stream is placed in the first reservoir or the first mixing device.

[0029] The first mixing device may include any known mixing device. In some embodiments, the first mixing device includes a static mixer. The static mixer may be a static in-line mixer. The first mixing device may include an inlet and an outlet, which may be configured to allow one or more streams of material to enter and exit the static mixer, respectively.

[0030] In some embodiments, the second stream is present in the first reservoir, and the mixing of the second stream is achieved at least partially using a dynamic mixing device. The dynamic mixing device may include a stirring device, an oscillating device, a shaking device, etc. The first reservoir may include an inlet and an outlet, which may be configured to allow one or more streams to enter and exit the first reservoir respectively. In some embodiments, heating and / or mixing of the second stream includes placing the second stream into the inlet of the first reservoir or the first mixing device.

[0031] Generally, the delivery of any one or more material streams disclosed herein (e.g., a first material stream, a second material stream, a third material stream, etc.) can be achieved or assisted by any known device (e.g., a pump). In some embodiments, placing a second material stream into the inlet of a first reservoir or a first mixing device includes delivering the second material stream or a component thereof using a device (e.g., a pump), which may be a screw pump, a peristaltic pump, etc.

[0032] Generally, the delivery of the hydrolysate and / or the flow (e.g., the first flow, the second flow, the third flow, etc.) in this article can be controlled at least in part by one or more flow meters.

[0033] In some embodiments, the method provided herein further includes subjecting a third stream to heating, mixing, or a combination thereof for a period of time, continuously and effectively driving a hydrolysis reaction at a desired rate, desired extent, or combination thereof to convert at least a portion of the lecithin into a product, wherein the product includes lysophosphatidylcholine.

[0034] In some embodiments, the method includes conveying a third feed stream from the outlet of a first reservoir or a first mixing device to a second reservoir. Heating and / or mixing of the third feed stream may be carried out at least partially in the second reservoir. The second reservoir may be a reactor.

[0035] In some embodiments, the effective conversion time of at least a portion of lecithin into the product is approximately 30 seconds to approximately 4 hours, approximately 30 seconds to approximately 3.5 hours, approximately 30 seconds to approximately 3 hours, approximately 30 seconds to approximately 2.5 hours, approximately 30 seconds to approximately 2 hours, approximately 30 seconds to approximately 1.5 hours, approximately 30 seconds to approximately 1 hour, approximately 30 seconds to approximately 40 minutes, approximately 30 seconds to approximately 30 minutes, approximately 30 seconds to approximately 25 minutes, approximately 30 seconds to approximately 20 minutes, approximately 30 seconds to approximately 15 minutes, approximately 30 seconds to approximately 10 minutes, approximately 1 minute to approximately 40 minutes, approximately 1 minute to approximately 30 minutes, approximately 1 minute to approximately 25 minutes, approximately 1 minute to approximately 20 minutes, approximately 1 minute to approximately 15 minutes, approximately 1 minute... Approximately 10 minutes, approximately 2 minutes to approximately 40 minutes, approximately 2 minutes to approximately 30 minutes, approximately 2 minutes to approximately 25 minutes, approximately 2 minutes to approximately 20 minutes, approximately 2 minutes to approximately 15 minutes, approximately 2 minutes to approximately 10 minutes, approximately 5 minutes to approximately 40 minutes, approximately 5 minutes to approximately 30 minutes, approximately 5 minutes to approximately 25 minutes, approximately 5 minutes to approximately 20 minutes, approximately 5 minutes to approximately 15 minutes, approximately 5 minutes to approximately 10 minutes, approximately 10 minutes to approximately 40 minutes, approximately 10 minutes to approximately 20 minutes, approximately 12 minutes to approximately 18 minutes, approximately 14 minutes to approximately 16 minutes, approximately 15 minutes, approximately 15 minutes to approximately 40 minutes, approximately 20 minutes to approximately 40 minutes, or approximately 25 minutes to approximately 40 minutes.

[0036] In some embodiments, heating the third stream includes heating the third stream to a temperature at which the hydrolysant effectively promotes the hydrolysis reaction of lecithin. In some embodiments, heating the third stream includes heating the third stream to a temperature of at least 40°C, at least 45°C, or at least 50°C. In some embodiments, heating the third stream includes heating the third stream to a temperature of about 50°C to about 70°C, about 55°C to about 65°C, or about 60°C.

[0037] In some embodiments, the method further includes heating a third feed stream at a temperature and time that effectively deactivates the hydrolysant. The hydrolysant is "deactivated" when its ability to promote the hydrolysis reaction is reduced by at least 95%, at least 99%, or 100%.

[0038] In some embodiments, the method further includes separating the product from the third stream. The separation of the product from the third stream can be achieved using any known technique. In some embodiments, the separation of the product includes heating the second or third stream at a temperature and time that effectively removes at least 80 wt%, at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 98 wt%, at least 99 wt%, or 100 wt% water from the third stream.

[0039] product

[0040] The products of embodiments of the methods provided herein may include lysophosphatidylcholine. In some embodiments, after product separation, water is present in the product at a concentration not exceeding 30 wt%, 25 wt%, 20 wt%, 15 wt%, 10 wt%, 5 wt%, or 1 wt% by weight of the product.

[0041] In some embodiments, the product comprises phosphatidylcholine (PC), lysophosphatidylcholine (LPC), or a combination thereof. In some embodiments, after product separation, PC is present in the product at a concentration of about 0.5 wt% to about 20 wt%, about 0.5 wt% to about 15 wt%, about 0.5 wt% to about 10 wt%, about 0.5 wt% to about 5 wt%, about 5 wt% to about 20 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 10 wt%, or about 5 wt% to about 8 wt%, based on the weight of the product. In some embodiments, after product separation, LPC is present in the product at a concentration of about 1 wt% to about 14 wt%, about 1 wt% to about 12 wt%, about 1 wt% to about 10 wt%, about 1 wt% to about 8 wt%, about 1 wt% to about 6 wt%, about 1 wt% to about 4 wt%, about 2 wt% to about 10 wt%, about 4 wt% to about 10 wt%, about 6 wt% to about 10 wt%, or about 8 wt% to about 10 wt%, based on the weight of the product.

[0042] In some embodiments, the conversion rates of the methods provided herein are about 10 wt% to about 75 wt%, about 20 wt% to about 75 wt%, about 30 wt% to about 75 wt%, about 40 wt% to about 75 wt%, about 50 wt% to about 75 wt%, about 60 wt% to about 75 wt%, about 10 wt% to about 70 wt%, about 10 wt% to about 60 wt%, about 10 wt% to about 50 wt%, about 10 wt% to about 40 wt%, about 10 wt% to about 30 wt%, or about 10 wt% to about 20 wt%, wherein the phrase “conversion rate” refers to the wt% conversion of PC in lecithin to LPC.

[0043] The products produced by embodiments of the methods provided herein may include lysophosphatidylcholine. In some embodiments, the product further includes phosphatidylcholine (PC).

[0044] hydrolysate

[0045] Generally, any hydrolysant that effectively promotes the hydrolysis of lecithin can be used in the embodiments of the methods provided herein. The hydrolysant may include an enzyme. For example, the hydrolysant may include phospholipases such as phospholipase A1, phospholipase A2, phospholipase B, or combinations thereof.

[0046] All cited publications are incorporated herein by reference in their entirety. Furthermore, where the definitions or uses of terms in the references incorporated herein by reference differ from or are contrary to the definitions of terms provided herein, the definitions provided herein shall apply, and the definitions in the references shall not apply.

[0047] Although certain aspects of conventional techniques have been discussed to facilitate the disclosure of various embodiments, the applicant does not intend to waive these technical aspects, and it is anticipated that this disclosure may cover one or more conventional technical aspects discussed herein.

[0048] This disclosure can solve one or more problems and deficiencies of known methods and processes. However, various embodiments are expected to prove useful in solving other problems and deficiencies in many other technical fields. Therefore, this disclosure should not necessarily be construed as limited to solving any particular problem or deficiency discussed herein.

[0049] In this specification, any reference to or discussion of a document, act, or knowledge item is not an admission that the document, act, or knowledge item, or any combination thereof, was publicly available, well-known to the public, or part of common common sense at the priority date, or otherwise constitutes prior art under applicable statutory provisions; nor is it an admission that its knowledge is related to any attempt to solve any problem covered in this specification.

[0050] In the description provided herein, the terms “comprising,” “is,” “contains,” “has,” and “includes” are used in an open manner and should therefore be construed as meaning “including, but not limited to.” When a method or system is claimed or described with respect to “comprising” various steps or components, unless otherwise stated, the method or system may also be described as “consisting substantially of various steps or components” or “comprised of various steps or components.”

[0051] The terms “a”, “an”, and “the” are intended to include multiple alternatives, such as at least one. For example, unless otherwise stated, the disclosure of “hydrolyzing agent,” “flow,” etc., is intended to cover a hydrolyzing agent, flow, etc., or a mixture or combination of more than one hydrolyzing agent, flow, etc.

[0052] This document may disclose various numerical ranges. Unless otherwise specified, when an applicant discloses or claims any type of range, the applicant intends to individually disclose or claim each possible value that such range can reasonably cover, including the endpoints of the range and any subranges and combinations thereof covered therein. Furthermore, all endpoint values ​​of the ranges disclosed herein are approximate values. As a representative example, the applicant discloses in some embodiments that water is present in the first feed stream at a concentration of about 25 wt% to about 35 wt%. This range should be interpreted as covering about 25 wt% and about 35 wt%, and further covering each of “about” 26 wt%, 27 wt%, 28 wt%, 29 wt%, 30 wt%, 31 wt%, 32 wt%, 33 wt%, and 34 wt%, including any range and subranges between any of these values.

[0053] As used in this article, the term “about” means ±10% of the numerical value of the numbers used.

[0054] Example

[0055] The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention in any way. Rather, it should be clearly understood that various other aspects, embodiments, modifications, and equivalents may be conceived by one of ordinary skill in the art upon reading the description herein without departing from the spirit of the invention or the scope of the appended claims. Therefore, other aspects of the invention will be apparent to those skilled in the art upon consideration of the specification and practice of the invention disclosed herein.

[0056] Example 1 - Preparation of lysophosphatidylcholine

[0057] In this example, the following materials were used: crude lecithin, phospholipase A1 (Novoenzymes A / S, Bagsvaerd, Denmark) and SUPELCOSIL. TM LC-diol column (250 × 4.6 mm, 5.0 µm) (Sigma-Aldrich, USA).

[0058] Laboratory-scale continuous enzymatic hydrolysis reaction

[0059] In this example, the following procedure is used to perform a laboratory-scale continuous enzymatic hydrolysis reaction on a 100 g scale.

[0060] The crude lecithin starting material contains approximately 10 wt% to approximately 300 wt% water; therefore, an emulsification step is performed using mechanical stirring prior to the continuous hydrolysis reaction. Typically, 100 g of crude lecithin is mixed with a phospholipase A1 solution (e.g., the enzyme is first dissolved in water) in a 500 mL beaker. The mixture is emulsified using a homogenizer at a temperature of approximately 50°C to approximately 60°C for approximately 1 to approximately 5 minutes. A homogeneous emulsion is produced.

[0061] Next, the emulsion is transferred to a continuous reactor by a pump to react in the continuous reactor for about 5 to about 30 minutes.

[0062] After the desired reaction time, the mixture is heated to approximately 95°C for about 5 minutes to inactivate the enzyme. The mixture is then dried at approximately 60°C for about 4 to about 12 hours to remove moisture from the product lysophosphatidylcholine.

[0063] In this example, the conversion rate was calculated by the molar ratio of LPC (in the product) / (PC + LPC) (in the starting material), and these values ​​were obtained by high-performance liquid chromatography (HPLC-ELSD) and phosphorus-31 nuclear magnetic resonance (NMR) spectroscopy combined with an evaporative light scattering detector.

[0064] Table 1 provides a list of laboratory-scale reactions used in this example to screen for continuous enzymatic hydrolysis reaction conditions. As shown in Table 1, enzyme amount, moisture content, reaction time, temperature, and emulsification time were all screened as variables for this reaction.

[0065] Table 1. Laboratory-scale reactions conducted to screen for continuous enzymatic hydrolysis conditions for lysophosphatidylcholine synthesis.

[0066]

[0067]

[0068] Pilot-scale continuous enzymatic hydrolysis reaction

[0069] The following procedure is used in this example to perform pilot-scale synthesis of lysophosphatidylcholine using a continuous enzymatic hydrolysis reaction.

[0070] This example uses two 100 L storage tanks, a peristaltic pump, a screw pump, a high-power online mixer, and a 10 L stainless steel continuous reactor.

[0071] Figure 1 The diagram illustrates the systems and methods used in the embodiments of this example. In simple terms, in Figure 1 In system / method 100, crude lecithin 101 and enzyme solution 102 (i.e., phospholipase A1) of this example are fed into a high-intensity online mixer 130 via screw pump 110 and peristaltic pump 120, respectively. Enzyme solution 102 is delivered by means of flow meter 121. After emulsification in mixer 130, mixture 103 is directly transferred to a 10 L continuous reactor 140 for subsequent reaction at approximately 60°C. The final product, lysophosphatidylcholine 104, is then obtained after deactivation and drying 150. Further analysis is performed by HPLC-ELSD and... 31 PNMR analysis was performed on the phospholipids in the products. Table 2 lists the reaction conditions for all batches tested in this pilot-scale experiment.

[0072] Table 2. Continuous enzymatic hydrolysis reaction conditions for pilot-scale batches used in this example (other reaction parameters are the same unless mentioned in the table below).

[0073]

[0074] HPLC-ELSD analysis of phospholipids

[0075] In this example, the HPLC-ELSD method was used to quantify PC and LPC in lecithin and lysophosphatidylcholine, as explained in the literature (see, for example, Sas B. et al., Journal of Chromatography A, 1999, 864(1): 179-182).

[0076] 31 P-NMR analysis

[0077] Based on the methods explained in the literature 31 P-NMR (see, for example, Mayar, M. et al., Journal of Agricultural and Food Chemistry, 2020, 68(17): 5009-50177). This analytical technique provides the molar ratio of PC and LPC molecules based on an internal standard (i.e., triphenyl phosphate (PPh3)). The molecular weight of each molecule and the values ​​derived from... 31 The molar ratio of the p-NMR data is used to calculate the weight percentage of each molecule.

[0078] Results - Effects of moisture, enzyme content, emulsification time, temperature, and reaction time on lysophosphatidylcholine conversion rate

[0079] Table 3 lists all the conversion rates of lysophosphatidylcholine from the aforementioned laboratory-scale reactions.

[0080] Table 3. The effect of enzyme amount, moisture content, reaction time, reaction temperature and emulsification time on lysophosphatidylcholine conversion rate.

[0081]

[0082]

[0083] like Figures 2A-2E The study summarized that enzyme quantity, moisture content, reaction time, reaction temperature, and emulsification time significantly affected the conversion rate of lysophosphatidylcholine. Specifically, Figures 2A-2E Describing enzyme quantity ( Figure 2A ), moisture ( Figure 2B ), reaction time ( Figure 2C ), reaction temperature ( Figure 2D ) and emulsification time ( Figure 2E The effect of lysophosphatidylcholine conversion rate.

[0084] When the reaction conditions included 30 wt% water (relative to lysophosphatidylcholine), a reaction time of 15 minutes, a reaction temperature of 60°C, and an emulsification time of 3 minutes (entries 1a, 2a-2g, Table 3), the conversion rate of lysophosphatidylcholine (36%, 47%, 57%, 70%, 67%, 60%, 61%, and 56%) initially increased with increasing enzyme concentration (50 ppm, 100 ppm, 200 ppm, 300 ppm), and then slightly decreased with further increases in enzyme concentration (500 ppm, 750 ppm, 1000 ppm). Figure 2A ).

[0085] When screening for moisture content (items 1a, 3a-3g, Table 3), the conversion rates of lysophosphatidylcholine (24%, 57%, 67%, 60%, 50%, 30%, and 16%) initially increased with increasing moisture content (10%, 30%, 50%, 80%, 100%, 200%, and 300%), and then decreased accordingly. Figure 2B ).

[0086] When the reaction temperature ( Figure 2D ) and emulsification time ( Figure 2E When screening for the effects of ), a similar trend was observed.

[0087] However, the conversion rates of lysophosphatidylcholine (27%, 43%, 57%, 60%, and 61%) increased with reaction time (5 minutes, 10 minutes, 15 minutes, 20 minutes, and 25 minutes). Figure 2C This improvement becomes less noticeable after a reaction time exceeding 15 minutes.

[0088] Example 2 - Optimization of Reaction Conditions

[0089] In this example, reaction conditions are optimized for an embodiment that uses a continuous enzymatic hydrolysis reaction to produce lysophosphatidylcholine.

[0090] Figures 3A-3E The figures summarize the effects of enzyme amount, moisture, reaction time, reaction temperature, and emulsification time on PC and LPC content. Specifically, these figures depict the effects of enzyme amount ( ) after a series of enzymatic hydrolysis reactions. Figure 3A ), moisture ( Figure 3B ), reaction time ( Figure 3C ), reaction temperature ( Figure 3D ) and emulsification time ( Figure 3E The results of the effect on PC and LPC content.

[0091] Since PC is an important nutrient in the final product, the optimal reaction conditions in this example not only take into account the conversion rate of LPC, but also the residual amount of PC in the product and the production cost.

[0092] Because enzyme costs can be a significant production expense, it may be advantageous to control, reduce, or minimize the amount of enzyme used in the methods presented herein. Therefore, 200 ppm of enzyme was chosen as the addition amount in the following experiments due to its relatively high PC and LPC content (6.2% and 6.4%, respectively) at a relatively low cost. Figure 3A ).like Figure 3B As shown, the PC content decreases sharply when the moisture content increases to above 50 wt%, which reduces the value of the final product and increases drying costs.

[0093] All experiments below were conducted using 30 wt% water. The PC content decreased sharply with increasing reaction time, while the LPC content increased with increasing reaction time. Figure 3C However, after a 15-minute reaction time, this improvement was not significant.

[0094] In the following experiments, the reaction time was 15 minutes. For the enzyme used in this example, the reaction temperature was screened near its optimal activity temperature. Figure 3D The LPC content was highest at 60°C (6.4%), and high PC content residue was also observed (6.2%). For the examples in this instance, an emulsification time of 3 minutes produced the best results. Figure 3E ).

[0095] Therefore, the favorable reaction conditions for producing lysophosphatidylcholine using the continuous enzymatic hydrolysis reaction of this example are 200 ppm enzyme, 30 wt% water, 15 minutes reaction time, and 3 minutes emulsification time at 60°C, and these parameters yield a conversion rate of approximately 57%. These parameters were applied in the following pilot-scale tests.

[0096] Pilot-scale synthesis of lysophosphatidylcholine

[0097] Table 4 lists the PC and LPC content and conversion rates of the pilot-scale synthesis from this example.

[0098] Table 4. Conversion and separation yields of HMBI synthesized on a pilot-scale basis.

[0099]

[0100] When the same reaction conditions are used, the conversion rate is very close to that of the aforementioned laboratory-scale synthesis. These similarities indicate the scalability of the method in this example.

[0101] For example, in a 100 g laboratory-scale synthesis using 200 ppm enzyme, 30 wt% water, a 15-minute reaction time, and a 3-minute emulsification time at 60 °C, the conversion (entry 2c, Table 3) was 57%, with a residual PC of 6.2%. When scaled up to a 20 kg pilot-scale synthesis, the conversion increased to approximately 60% (average), with a residual PC of 6.0% (average) (lots 1–5, Table 4).

[0102] Comparison of traditional batch reaction methods and continuous enzymatic hydrolysis methods

[0103] Compared to traditional batch methods used for the commercial production of lysophosphatidylcholine, the method of preparing lysophosphatidylcholine using continuous enzymatic hydrolysis reactions exhibits one or more advantages. For example, continuous methods require less space, thus eliminating or reducing the need to build plants with many reactors. As another example, reaction time and cycle time are significantly reduced. As yet another example, labor input is greatly reduced due to continuous reaction methods.

[0104] Table 5 provides a complete comparison of the methods described.

[0105] Table 5. Comparison of the new continuous reaction method and the traditional batch reaction method.

[0106]

[0107] The screening of reaction conditions described in the aforementioned examples revealed that the contents of both PC and LPC decreased with changes in the variables (entries 2f-2g, 3d-3g, Table 2). This may be due to excessive hydrolysis of lecithin by adding an excessive amount of phospholipase A1, which is highly likely to produce another product, glycerophosphorylcholine (GPC) (see, for example, Zhang, K. et al., European Journal of Lipid Science and Technology, 2012, 114(11): 1254-1260).

[0108] However, the sequential enzymatic hydrolysis described herein can be precisely controlled—such as by controlling the reaction time—which can avoid or reduce the possibility of “over-hydrolyzing” lecithin. The ability to control sequential enzymatic hydrolysis ensures the stability of the lysophosphatidylcholine product.

[0109] Compared to traditional batch reaction methods, the continuous reaction methods described in the aforementioned examples offer one or more advantages in addition to requiring less space. For example, the embodiments of the continuous reaction method reduce reaction time and cycle time by at least 95% and 94%, respectively (Table 5), which lowers operating and energy costs. It also avoids or reduces the tedious labor required by traditional batch reaction methods, which can significantly reduce manufacturing costs. In fact, the estimated total production cost savings per ton of lysophosphatidylcholine product are approximately $200 to approximately $400.

[0110] In the 20 kg pilot-scale production test, the conversion rate (60%) was slightly higher than that in the corresponding laboratory-scale test (57%). This difference could be due to the stronger emulsifying effect of the powerful online mixer used in the pilot-scale experiment. However, these results indicate the importance of emulsification for continuous reaction embodiments. Another or alternative reason for this difference could be the easier control of the pilot-scale equipment used in the aforementioned examples.

[0111] aspect

[0112] The following is a non-limiting list of various aspects of this disclosure.

[0113] Aspect 1. A method for producing a product, the method comprising, substantially comprising, or consisting of: providing a first stream comprising, substantially comprising, or consisting of lecithin and water; and contacting the first stream with a hydrolyzing agent to form a second stream, wherein the hydrolyzing agent effectively promotes the hydrolysis reaction of the lecithin.

[0114] Aspect 2. The method according to aspect 1 further comprises, substantially comprises, or further comprises: subjecting the second stream to heating, mixing, or a combination thereof for a period of time to effectively form a third stream containing an emulsion.

[0115] Aspect 3. The method according to aspect 2, wherein contacting the first feed stream with the hydrolysant and subjecting the second feed stream to heating, mixing, or a combination thereof are carried out simultaneously or sequentially.

[0116] Aspect 4. The method according to any one of Aspects 1 to 3, further comprising, substantially comprising, or further comprising: subjecting the second or third stream to heating, mixing, or a combination thereof, for a sustained and effective period of time at a desired rate, desired extent, or combination thereof to drive the hydrolysis reaction to convert at least a portion of the lecithin into a product, wherein the product comprises, substantially comprises, or comprises lysophosphatidylcholine.

[0117] Aspect 5. The method according to any of the foregoing aspects further comprises, substantially comprises, or further comprises: heating the second or third stream at a temperature and time that effectively deactivates the hydrolysant.

[0118] Aspect 6. The method according to any of the foregoing aspects further comprises, substantially comprises, or further comprises: separating the product from the second stream or the third stream.

[0119] First storage unit / first mixing device

[0120] Aspect 7. The method according to any of the preceding aspects, wherein the second feed stream is subjected to heating, mixing or a combination thereof at least in part to a first reservoir, a first mixing device or a combination thereof.

[0121] Aspect 8. The method according to aspect 7, wherein the first mixing device comprises, is substantially composed of, or is composed of a static mixer.

[0122] Aspect 9. The method according to aspect 8, wherein the static mixer is a static online mixer.

[0123] Aspect 10. The method according to any of the preceding aspects, wherein when the second stream is present in the first reservoir, the mixing of the second stream is at least partially achieved by a dynamic mixing device.

[0124] Aspect 11. The method according to any of the preceding aspects, wherein the heating and / or mixing of the second stream comprises, substantially comprises, or comprises the following: placing the second stream into the inlet of the first reservoir or the first mixing device.

[0125] Aspect 12. The method according to any of the preceding aspects, wherein placing the second material stream at the inlet of the first reservoir or the first mixing device comprises, substantially comprises, or comprises: conveying the second material stream or a component thereof by means of a device, such as a pump, which may be a screw pump, a peristaltic pump, etc.

[0126] Aspect 13. The method according to any of the preceding aspects, wherein contacting the first stream with the hydrolysant to form the second stream is carried out at least partially in the first reservoir or the first mixing device.

[0127] Aspect 14. The method according to any of the preceding aspects, wherein contacting the first stream with the hydrolysant to form the second stream occurs before placing the second stream into the inlet of the first reservoir or the first mixing device.

[0128] Aspect 15. The method according to any of the preceding aspects, wherein contacting the first feed stream with the hydrolysant comprises, substantially comprises, or comprises comprising: conveying the first feed stream to the first reservoir or the first mixing device, and conveying the hydrolysant to the first reservoir or the first mixing device, wherein the conveying of the first feed stream and the hydrolysant is carried out independently using any known device, such as a pump, for example a screw pump, peristaltic pump, etc.

[0129] Aspect 16. The method according to aspect 15, wherein the first material flow is delivered by a screw pump.

[0130] Aspect 17. The method according to aspect 15 or 16, wherein the hydrolysate is delivered using a peristaltic pump.

[0131] Aspect 18. The method according to any of the preceding aspects, wherein the delivery of the first flow, the hydrolysant, the second flow, the third flow, or a combination thereof is controlled at least in part by one or more flow meters.

[0132] Second storage device

[0133] Aspect 19. The method according to any of the preceding aspects, wherein the method further comprises conveying the third stream from the outlet of the first reservoir or the first mixing device to the second reservoir.

[0134] Aspect 20. The method according to aspect 19, wherein the heating and / or mixing of the third feed stream is at least partially carried out in the second reservoir.

[0135] Aspect 21. The method according to aspect 19 or 20, wherein the second reservoir is a reactor.

[0136] First material flow

[0137] Aspect 22. The method according to any of the preceding aspects, wherein water is present in the first feed stream at a concentration of about 10 wt% to about 300 wt%, about 10 wt% to about 250 wt%, about 10 wt% to about 200 wt%, about 10 wt% to about 150 wt%, about 10 wt% to about 100 wt%, about 10 wt% to about 50 wt%, about 20 wt% to about 40 wt%, about 25 wt% to about 35 wt%, about 50 wt% to about 300 wt%, about 100 wt% to about 300 wt%, about 150 wt% to about 300 wt%, about 200 wt% to about 300 wt%, or about 250 wt% to about 300 wt%, based on the weight of the lecithin.

[0138] Second material flow

[0139] Aspect 23. The method according to any of the preceding aspects, wherein the hydrolysant is present in the second feed stream at a concentration relative to the lecithin of about 10 ppm to about 1,500 ppm, about 10 ppm to about 1,250 ppm, about 10 ppm to about 1,000 ppm, about 10 ppm to about 750 ppm, about 10 ppm to about 500 ppm, about 10 ppm to about 300 ppm, about 10 ppm to about 200 ppm, about 10 ppm to about 100 ppm, about 10 ppm to about 50 ppm, about 100 ppm to about 1,500 ppm, about 200 ppm to about 1,500 ppm, about 300 ppm to about 1,500 ppm, about 500 ppm to about 1,500 ppm, about 750 ppm to about 1,500 ppm, about 750 ppm to about 1,250 ppm, or about 750 ppm to about 1,000 ppm.

[0140] Third material flow

[0141] Aspect 24. The method according to any of the preceding aspects, wherein the emulsion of the third stream is a homogeneous emulsion.

[0142] Aspect 25. The method according to any of the preceding aspects, wherein the emulsion is a Newtonian fluid, such as a Newtonian fluid that can be transported by a known device (such as a pump described herein).

[0143] reaction time

[0144] Aspect 26. The method according to any of the preceding aspects, wherein the time for effectively forming the third flow comprising, substantially comprising, or consisting of the emulsion is about 1 minute to about 10 minutes, about 1 minute to about 8 minutes, about 1 minute to about 5 minutes, about 2 minutes to about 4 minutes, about 2.5 minutes to about 3.5 minutes, about 3 minutes, or about 1 minute to about 3 minutes.

[0145] Aspect 27. The method according to any of the preceding aspects, wherein the effective conversion time of at least a portion of the lecithin into the product is from about 30 seconds to about 4 hours, from about 30 seconds to about 3.5 hours, from about 30 seconds to about 3 hours, from about 30 seconds to about 2.5 hours, from about 30 seconds to about 2 hours, from about 30 seconds to about 1.5 hours, from about 30 seconds to about 1 hour, from about 30 seconds to about 40 minutes, from about 30 seconds to about 30 minutes, from about 30 seconds to about 25 minutes, from about 30 seconds to about 20 minutes, from about 30 seconds to about 15 minutes, from about 30 seconds to about 10 minutes, from about 1 minute to about 40 minutes, from about 1 minute to about 30 minutes, from about 1 minute to about 25 minutes, from about 1 minute to about 2 .... Approximately 15 minutes, approximately 1 minute to approximately 10 minutes, approximately 2 minutes to approximately 40 minutes, approximately 2 minutes to approximately 30 minutes, approximately 2 minutes to approximately 25 minutes, approximately 2 minutes to approximately 20 minutes, approximately 2 minutes to approximately 15 minutes, approximately 2 minutes to approximately 10 minutes, approximately 5 minutes to approximately 40 minutes, approximately 5 minutes to approximately 30 minutes, approximately 5 minutes to approximately 25 minutes, approximately 5 minutes to approximately 20 minutes, approximately 5 minutes to approximately 15 minutes, approximately 5 minutes to approximately 10 minutes, approximately 10 minutes to approximately 40 minutes, approximately 10 minutes to approximately 20 minutes, approximately 12 minutes to approximately 18 minutes, approximately 14 minutes to approximately 16 minutes, approximately 15 minutes, approximately 15 minutes to approximately 40 minutes, approximately 20 minutes to approximately 40 minutes, or approximately 25 minutes to approximately 40 minutes.

[0146] reaction temperature

[0147] Aspect 28. The method according to any of the preceding aspects, wherein the heating of the second or third stream comprises heating the second or third stream to (i) a temperature at which the hydrolysant effectively promotes the hydrolysis reaction of the lecithin, (ii) a temperature of at least 40°C, at least 45°C, or at least 50°C, or (iii) a temperature of about 50°C to about 70°C, about 55°C to about 65°C, or about 60°C.

[0148] hydrolysate

[0149] Aspect 29. The method according to any of the preceding aspects, wherein the hydrolysant comprises, is substantially composed of, or is composed of an enzyme.

[0150] Aspect 30. The method according to any of the preceding aspects, wherein the hydrolysant comprises, is substantially composed of, or is composed of phospholipase.

[0151] Aspect 31. The method according to any of the preceding aspects, wherein the hydrolysant comprises, or is substantially composed of, phospholipase A1, phospholipase A2, phospholipase C, phospholipase D or a combination thereof.

[0152] Separation products

[0153] Aspect 32. The method according to any of the preceding aspects, wherein the separation of the product comprises, substantially comprises, or comprises the following: heating the second stream or the third stream at a temperature and time at which at least 80 wt%, at least 85 wt%, at least 90 wt%, at least 95 wt%, at least 98 wt%, at least 99 wt%, or 100 wt% of the water is effectively removed from the second stream or the third stream.

[0154] product

[0155] Aspect 33. The method according to any of the preceding aspects, wherein after separation of the product, water is present in the product at a concentration not exceeding 30 wt%, 25 wt%, 20 wt%, 15 wt%, 10 wt%, 5 wt%, or 1 wt% by weight of the product.

[0156] Aspect 34. The method according to any of the preceding aspects, wherein the product further comprises or is substantially composed of phosphatidylcholine (PC).

[0157] Aspect 35. The method according to aspect 34, wherein, after separation of the product, PC is present in the product at a concentration of about 0.5 wt% to about 20 wt%, about 0.5 wt% to about 15 wt%, about 0.5 wt% to about 10 wt%, about 0.5 wt% to about 5 wt%, about 5 wt% to about 20 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 10 wt%, or about 5 wt% to about 8 wt%, based on the weight of the product.

[0158] Aspect 36. The method according to any of the preceding aspects, wherein, after separation of the product, lysophosphatidylcholine (LPC) is present in the product at a concentration of about 1 wt% to about 14 wt%, about 1 wt% to about 12 wt%, about 1 wt% to about 10 wt%, about 1 wt% to about 8 wt%, about 1 wt% to about 6 wt%, about 1 wt% to about 4 wt%, about 2 wt% to about 10 wt%, about 4 wt% to about 10 wt%, about 6 wt% to about 10 wt%, or about 8 wt% to about 10 wt%.

[0159] Conversion rate

[0160] Aspect 37. The method according to any of the preceding aspects, wherein about 10 wt% to about 75 wt%, about 20 wt% to about 75 wt%, about 30 wt% to about 75 wt%, about 40 wt% to about 75 wt%, about 50 wt% to about 75 wt%, about 60 wt% to about 75 wt%, about 10 wt% to about 70 wt%, about 10 wt% to about 60 wt%, about 10 wt% to about 50 wt%, about 10 wt% to about 40 wt%, about 10 wt% to about 30 wt%, or about 10 wt% to about 20 wt% of the lecithin is converted to lysophosphatidylcholine, wherein the phrase “conversion rate” refers to the wt% of PC converted to LPC.

[0161] condition

[0162] Aspect 38. The method according to any of the preceding aspects, wherein the first stream does not include a non-aqueous liquid, such as an organic liquid, and / or wherein (i) the first stream is contacted with the hydrolysant, (ii) the second stream is subjected to heating, mixing, or a combination thereof, and / or (iii) the third stream is subjected to heating, mixing, or a combination thereof in the absence of a non-aqueous liquid, such as an organic liquid.

[0163] Aspect 39. The method according to any of the preceding aspects, wherein the first stream does not include a hydroxyl acceptor, and / or wherein (i) the first stream is contacted with the hydrolysant, (ii) the second stream is subjected to heating, mixing, or a combination thereof, and / or (iii) the third stream is subjected to heating, mixing, or a combination thereof without the presence of a hydroxyl acceptor (such as any compound that can receive or accept a phosphatidyl group in the presence of phospholipase (e.g., serine, glycerol, L-ascorbic acid, glucose, choline, etc.)).

[0164] system

[0165] Aspect 40. A system, which is as follows Figure 1 As depicted in the text.

[0166] Aspect 41. A system, such as a system for performing, fully or partially, any of the methods according to the foregoing aspects, wherein the system comprises, substantially consists of, or consists of: (i) a first reservoir and / or a first mixing device, and (ii) a reactor, wherein the reactor is in fluid communication with the first reservoir and / or the first mixing device.

[0167] Aspect 42. The system according to any of the foregoing aspects further includes, is substantially composed of, or is composed of a drying device, wherein optionally the drying device is in fluid communication with the reactor.

[0168] Aspect 43. The system according to any of the preceding aspects further comprises one or more pumps, one or more flow meters or combinations thereof, substantially consisting of or consisting of them.

[0169] Aspect 44. The system according to any of the preceding aspects, wherein the first mixing device is a static mixing device, such as an online static mixing device.

Claims

1. A method for producing a product, such as a continuous method, said method comprising: A first feed stream comprising lecithin and water is provided, wherein the water is present in the first feed stream at a concentration of about 10 wt% to about 300 wt% based on the weight of the lecithin; The first stream is brought into contact with a hydrolyzing agent to form a second stream, wherein the hydrolyzing agent effectively promotes the hydrolysis reaction of the lecithin. The time during which the second stream is subjected to heating, mixing, or a combination thereof to continuously and effectively form a third stream containing an emulsion; and The time during which the third feed stream is subjected to heating, mixing, or a combination thereof to continuously and effectively drive the hydrolysis reaction at a desired rate, desired extent, or combination thereof to convert at least a portion of the lecithin into the product; The product contains lysophosphatidylcholine; and Optionally, the effective conversion time of at least a portion of the lecithin into the product is from about 30 seconds to about 4 hours.

2. The method of claim 1, wherein the mixing of the second stream comprises placing the second stream into the inlet of the mixing device.

3. The method according to claim 2, wherein the mixing device is a static mixer.

4. The method of claim 2, further comprising conveying the third stream from the outlet of the mixing device to a reservoir, wherein the heating and / or mixing of the third stream occurs at least partially in the reservoir.

5. The method of claim 1, further comprising heating the third feed stream at a temperature and time that effectively deactivates the hydrolysant.

6. The method of claim 1, further comprising separating the product from the third feed stream.

7. The method of claim 6, wherein the separation of the product comprises heating the third stream at a temperature and time at which at least 95% by weight of water is effectively removed from the third stream.

8. The method of claim 1, wherein the hydrolysant comprises an enzyme.

9. The method of claim 8, wherein the enzyme comprises phospholipase.

10. The method of claim 1, wherein the hydrolysant is present in the second feed stream at a concentration of about 10 ppm to about 1,500 ppm relative to the lecithin.

11. The method of claim 1, wherein the water is present in the first feed stream at a concentration of about 20 wt% to about 40 wt% based on the weight of the lecithin.

12. The method of claim 1, wherein the water is present in the first feed stream at a concentration of about 30 wt% based on the weight of the lecithin.

13. The method of claim 1, wherein the effective time for forming the third material flow is from about 2 minutes to about 4 minutes.

14. The method of claim 1, wherein the effective time for forming the third material flow is approximately 3 minutes.

15. The method according to claim 1, wherein (i) the effective driving time for the hydrolysis reaction is from about 10 minutes to about 20 minutes, (ii) the third feed stream is heated to a temperature of from about 55°C to about 60°C to drive the hydrolysis reaction, or (iii) both (i) and (ii) are satisfied.

16. The method of claim 1, wherein the product further comprises phosphatidylcholine (PC).

17. The method of claim 16, wherein after separation of the product, the phosphatidylcholine is present in the product at a concentration of about 5 wt% to about 10 wt% based on the weight of the product.

18. The method of claim 1, wherein the lysophosphatidylcholine comprises lysophosphatidylcholine, and wherein, after separation of the product, the lysophosphatidylcholine is present in the product at a concentration of about 2 wt% to about 14 wt% based on the weight of the product.

19. The method of claim 1, wherein the lecithin comprises phosphatidylcholine, wherein the lysophosphatidylcholine comprises lysophosphatidylcholine, and wherein about 50 wt% to about 75 wt% of the phosphatidylcholine in the lecithin is converted into the lysophosphatidylcholine of the product.

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