CN111233948A - Rhamnolipid calcium, preparation method and application - Google Patents
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Abstract
The invention discloses rhamnolipid calcium, a preparation method and application, wherein a rhamnolipid calcium solution containing calcium ions is added into a rhamnolipid-containing solution to have a precipitation reaction with rhamnolipid and impurities, and then the rhamnolipid calcium solution obtained by centrifugal separation is subjected to excessive concentration evaporation by utilizing the characteristic that the rhamnolipid calcium can be dissolved in an organic solvent and other impurities cannot be dissolved, so that light-colored rhamnolipid calcium powder is obtained, the purity is higher than 90%, and the recovery rate exceeds 80%. The invention prepares a new product, namely rhamnolipid calcium, and the preparation process is simple, the process is more green, the cost is lower, and the purification efficiency is high. The rhamnolipid powder is not a traditional solution or paste, but is in a powder shape, is easy to store and transport for a long time, and is light in color. The rhamnolipid calcium has similar structural good properties with rhamnolipid, and can be used in various fields instead of rhamnolipid.
Description
Technical Field
The invention relates to a preparation method of rhamnolipid calcium and application thereof in washing and caring products and cosmetics.
Background
The rhamnolipid is an anionic biosurfactant and is mainly obtained by fermentation of pseudomonas or burkholderia. Rhamnolipids are found to have 58 chemical structures, which can be mainly classified into four major groups: monorhamnolipid homologues, monorhamnodilipid homologues, dirhamnolipid monolipid homologues, dirhamnolipid diracholipid homologues. The rhamnolipid obtained by fermentation is a mixture of various homologues, is soluble in water and generally exists in a paste form of the mixture. The rhamnolipid has good surface activity effects of antibiosis, washing, wetting, permeation, emulsification and the like, so the rhamnolipid has wide potential markets in the fields of medical treatment, environment, petroleum, food and the like. And the rhamnolipid has biological activities of antibiosis, wrinkle resistance, aging resistance and the like, low toxicity and low skin irritation, and the characteristics make the rhamnolipid have great competitiveness in the cosmetic industry.
The purification and separation of rhamnolipids are very difficult. The rhamnolipid-containing fermentation broth contains very complex components, and contains various impurities such as thalli, proteins, polysaccharides, pigments, glycerides, fatty acids and the like besides rhamnolipid, so that the separation is difficult and the cost is high. The currently reported methods for separating and purifying rhamnolipid mainly include acid precipitation, membrane separation, solvent extraction, column chromatography, phase transfer method and the like. Generally, pH is adjusted to about 4.0 by using acid to precipitate rhamnolipid, then crude purification is carried out, and organic solvents such as methanol, chloroform, ethyl acetate, butyl acetate, hexane and the like are used for extraction, so that the method consumes a large amount of organic solvents, has high energy consumption, and the obtained product has poor purity, is dark brown paste and is poor in use convenience. Subsequently, m.heyd et al used methanol and pH to adjust rhamnolipid micelle size in combination with the ultrafiltration membrane method of polysulfone membrane to perform a two-step process to separate rhamnolipid: firstly, intercepting large-size rhamnolipid micelles and macromolecular proteins by an ultrafiltration membrane, and allowing small-molecular impurities to permeate; in the second step, methanol is added to reduce the rhamnolipid micelle size and trap the macromolecular proteins. The method effectively removes impurities such as micromolecular impurities, proteins and the like, so that the purity is higher, but a special and expensive ultrafiltration membrane device is needed, the problem of membrane pollution is serious, and the membrane is easy to deform under the action of an organic solvent. The column chromatography is carried out by gradient elution through a mixed solution of methanol and chloroform, the required time is long, the consumption of an organic solvent is large, and the cost is extremely high. German winning (2013) adopts a phase transfer method, namely according to the difference of distribution coefficients (caused by different solubilities of rhamnolipid in an organic solvent phase and a potassium hydroxide solution) of rhamnolipid under different pH values, the rhamnolipid is transferred to the solvent phase firstly and then to an alkali solution to remove hydrophilic and hydrophobic impurities, the operation method is complicated, and the separation yield is low.
In addition, the final product obtained by the method is not a paste or an aqueous solution, is difficult to transport and store, is inconvenient to use, has dark color, and has the defects of high separation cost and poor purity and yield.
Disclosure of Invention
The invention aims to provide rhamnolipid calcium and a preparation method thereof aiming at the defects of the prior art.
The invention utilizes the complexation reaction of calcium-containing ions and rhamnolipid to generate the rhamnolipid calcium which is insoluble in water. Then, the physical and chemical properties that the rhamnolipid calcium is easily dissolved by the alcohol and ester organic solvents but other impurities such as polysaccharide, protein, long-chain fatty acid and the like cannot be dissolved are utilized, so that the rhamnolipid calcium is well separated, the purity of the rhamnolipid calcium product obtained by the method is high, no harmful and toxic organic solvent is involved, and the method is suitable for common industry and agriculture and also suitable for the daily chemical industry. In particular, the benefits of the present invention are detailed below.
The invention aims to provide a method for converting rhamnolipid into rhamnolipid calcium and separating and purifying the rhamnolipid calcium, aiming at the defect that the existing rhamnolipid product is not easy to store and transport, and the method comprises the following steps:
(1) and (3) dropwise adding a calcium ion-containing solution into the rhamnolipid fermentation liquor or the rhamnolipid-containing solution under stirring, and centrifuging to obtain a crude rhamnolipid calcium precipitate.
(2) Dissolving the crude rhamnolipid calcium precipitate collected in the step (1) in an organic solvent, and centrifuging to remove impurities which cannot be dissolved in the organic solvent.
(3) Evaporating the organic solution of the rhamnolipid calcium collected in the step (2) to obtain rhamnolipid calcium powder.
Further, the rhamnolipid fermentation broth or the rhamnolipid-containing solution in the step (1) is firstly subjected to centrifugation to remove solid impurities.
The stirring mode in the step (1) adopts mechanical stirring.
Further, in the step (1), the centrifugation conditions are as follows: centrifuging at 1000-5000rmp for 10-30 min.
Further, in the step (1), the molar ratio of rhamnolipid to calcium ion is 1: 1-1: 5, preferably, a 1: 1.2-1: 3.
further, in the step (1), a solution containing calcium ions is dripped and then reacted for 0.1-4 h. The reaction temperature is 10-60 deg.C, preferably 20-50 deg.C.
Further, the organic solvent in the step (2) is selected from methanol, ethanol, propanol, isopropanol, butanol, ethyl acetate, butyl acetate and the like, and preferably, methanol, ethanol, propanol, isopropanol and butanol are used as the organic solvent.
Further, the evaporation step in the step (3) adopts reduced pressure or atmospheric distillation.
The invention also provides application of the rhamnolipid calcium in washing and caring products and cosmetics.
The rhamnolipid calcium of the invention has a similar main structure as rhamnolipid, except that the hydrogen ions of rhamnolipid are replaced by calcium ions (see nuclear magnetic and analytical structural identification of fig. 1 and fig. 2). The rhamnolipid calcium obtained by the invention is not used as a paste or a solution, is insoluble in neutral pure water, is in a powder shape, is soluble in an alcohol organic solvent, is light in color and is easy to transport and store. When in use, the calcium ions can be decomplexed in the presence of other substances (such as hydrogen ions) to obtain rhamnolipid. The rhamnolipid calcium has similar structural good properties with rhamnolipid, and can be used in various fields instead of rhamnolipid. The invention also provides an efficient, convenient and rapid preparation method of the rhamnolipid calcium, which uses less solvent, uses green solvent and can be obtained by using sustainable resources or direct microbial fermentation. Meanwhile, the requirement on temperature is not high, equipment which does not need too much energy consumption is simple, and the technical difficulty is low.
Drawings
FIG. 1 is a drawing of1H-NMR analysis spectrogram, wherein a is rhamnolipid calcium, and b is rhamnolipid;
FIG. 2 is an infrared spectrum in which a is rhamnolipid calcium and b is rhamnolipid.
Detailed Description
The present invention will be described in detail with reference to specific examples.
In the following examples, a rhamnolipid broth is obtained from the fermentation of pseudomonas aeruginosa, as one way, it can be fermented by, but is not limited to:
the fermentation strain is Pseudomonas aeruginosa ZJU-211 (preservation number: CCTCC No: M209237), the strain is inoculated in 60ml of seed culture medium, the temperature is 38 ℃, the rotating speed of a shaking table is 200rpm, and the shaking table is cultured for 48 hours to obtain the strain in the shaking bottle. The seed culture medium comprises the following components: first-grade soybean oil, 40 g/L: NaNO3，4g/L；NaCl，1.5g/L；KCl，1.5g/L；CaCl2·2H2O，0.2g/L；KH2PO4，4g/L；Na2HPO4·12H2O，4g/L；MgSO40.3 g/L; trace element, 2.5 mL/L. The trace elements comprise FeCl3·6H2O 0.08g/L，ZnSO4·7H2O 0.75g/L，CuSO4·5H2O 0.075g/L，MnSO4·H2O 0.75g/L，H3BO3，0.15g/L。
The shake flask strain is inoculated into 3 tons of fermentation medium, the inoculation amount is 2% (v/v), the temperature in the fermentation process is controlled at 38 ℃, the ventilation capacity is 1.0vvm, the stirring speed is 300rpm, and the fermentation period is 4 days. The fermentation medium consisted of: first-grade soybean oil, 70 g/L; NaNO3，8g/L；NaCl，1.5g/L；KCl，1.5g/L；CaCl2·2H2O，0.2g/L；KH2PO4，4g/L；Na2HPO4·12H2O，4g/L；MgSO40.3 g/L; trace element, 2.5 mL/L. The trace elements comprise FeCl3·6H2O 0.08g/L，ZnSO4·7H2O 0.75g/L，CuSO4·5H2O 0.075g/L，MnSO4·H2O 0.75g/L，H3BO3，0.15g/L。
After the fermentation is finished, about 1.6 tons of rhamnolipid 50g/L fermentation liquor is obtained.
Example 1 preparation of calcium fatty acid from rhamnolipid fermentation broth:
500ML 50g/L rhamnolipid fermentation liquor is sterilized at high temperature, and the color of the fermentation liquor is dark brown. Centrifuge at 1000rmp for 10min, discard the precipitate, place in 1000ML round bottom flask. At room temperature, CaCl was slowly added with magnetic stirring2Aqueous solution, such that the rhamnolipid: CaCl2The molar ratio is approximately equal to 1:0.5, and the reaction is stopped after 0.1 h. Centrifuging at 1000rmp for 10min, and collecting bottom rhamnolipid calcium precipitate. And further adopting methanol to fully dissolve the rhamnolipid calcium precipitate, and centrifuging for 10min at the rotating speed of 1000rmp to obtain the organic solution of rhamnolipid. After the organic solution of rhamnolipid calcium is evaporated, 19.2g of rhamnolipid calcium powder is obtained, the color of the powder is light yellow, the rhamnolipid content is 91% by high performance liquid chromatography analysis, and the yield is about 80%.
Simultaneously delivering the prepared rhamnolipid calcium and rhamnolipid to carry out sample preparation1And H-NMR identifies that the solvent is deuterated methanol. The nuclear magnetic spectrum of rhamnolipid calcium is shown in figure 1 a. The analytical results were as follows:1H NMR(500MHz,Methanol-d4) δ 5.25(p, J ═ 6.4Hz,1H),4.05(p, J ═ 6.0Hz,1H), 3.77-3.58 (m,3H),3.37(dt, J ═ 16.3,9.4Hz,1H), 2.63-2.51 (m,3H),2.49(dd, J ═ 15.2,5.8Hz,1H),1.63(q, J ═ 7.3,6.6Hz,2H),1.55(q, J ═ 7.2,6.8Hz,2H), 1.38-1.21 (m,25H),0.90(t, J ═ 6.7Hz,6H), for a total of 10 major peaks; the nuclear magnetic spectrum of rhamnolipid is shown in figure 1 b. The analytical results were as follows:1H NMR(500MHz,Methanol-d4)δ5.33(dd,J＝8.7,4.8Hz,1H),4.11(dq, J ═ 8.9,5.0Hz,1H), 3.84-3.62 (m,3H),3.36(dq, J ═ 19.0,9.5Hz,1H),2.47(dddd, J ═ 32.0,27.6,15.0,6.4Hz,3H), 1.63-1.50 (m,4H), 1.34-1.27 (m,19H),1.24(t, J ═ 5.3Hz,3H),0.90(td, J ═ 7.0,2.2Hz,5H), for a total of 9 major peaks. Compared with the existing nuclear magnetic results, the hydrogen of the carboxyl (-COOH) is not detected in the two substances, and probably the carboxyl is less in the two substances, so the detection signals are weak and both accord with the literature (Monteiro, Chemistry)&Physics of Lipids, 2007). The results indicate that the major structure of rhamnolipid calcium is similar to rhamnolipid.
Fig. 2a is an infrared spectrum of rhamnolipid calcium, and fig. 2b is an infrared spectrum of rhamnolipid. Comparing the two ir spectra, it can be seen that the two species have similar peak shapes: 1165. 1123cm-1Is a carboxylic ester group absorption peak generated by C-O-C stretching vibration, 1379cm-1C-H or O-H deformation vibration at the position causes an absorption peak; 1730cm-1Is a typical absorption peak generated by C ═ O stretching vibration; 3347cm-1The absorption peak is caused by OH stretching vibration in the molecule; 2924. 2855cm-1Is the absorption peak generated by the C-H stretching vibration of methyl and methylene in the oleophylic hydrocarbon chain. The two significantly different peaks are: 1560-1570 cm in FIG. 2a-1And 1380 to 1460 cm-1Two strong absorption peaks appeared in the process are antisymmetric stretching vibration peaks of carboxylate anions, because glycolipid calcium is a divalent metal salt, and two C-O bonds in the carboxylate anions are completely averaged, the stretching vibration is strongly coupled, so that the absorption band of the glycolipid calcium is shifted to a low frequency direction.
According to the infrared spectrum analysis, the rhamnolipid calcium is a compound produced by replacing respective hydrogen ions in carboxylic acid groups of two molecules of murine rhamnolipids with calcium ions, but because single/double rhamnose and single/double fatty acid in the rhamnolipid can be changed, rhamnolipid calcium with various composition structures is produced. The following lists the structural formulas of three mono-and di-rhamnolipid calcium:
wherein n, m, x and y are positive integers, and z and l are 0 or positive integers. Rhamnolipid calcium is prepared with mostly two fatty acids, i.e. when z, l equals 1.
The rhamnolipid calcium has a main structure similar to that of rhamnolipid, so that the properties and the application of the rhamnolipid calcium are similar to those of rhamnolipid. However, the rhamnolipid calcium is insoluble in neutral pure water, is in a powder shape, and has light color and is easy to transport and store compared with the rhamnolipid.
Example 2 preparation of calcium fatty acid from rhamnolipid paste:
dissolving 25g rhamnolipid (purity 80%, obtained by acid precipitation of fermentation broth and extraction with organic solvent) in 100mL diluted alkali water solution, centrifuging at 5000rmp for 10min, discarding insoluble substances, and placing into 250mL round-bottom flask. The flask was placed in a 50 ℃ thermostatted water bath, Ca (OH) was slowly added with mechanical stirring2Solution, such that the rhamnolipid: ca (OH)2And the reaction is stopped after 4 hours, wherein the molar ratio is approximately 1: 5. Centrifuging at 5000rmp for 10min to obtain crude rhamnolipid calcium precipitate. Centrifuging at 5000rmp for 10min to obtain rhamnolipid precipitate. Drying the rhamnolipid precipitate, washing with isopropanol for multiple times, and centrifuging at the rotation speed of 5000rmp for 10min to obtain the rhamnolipid organic solution. Distilling the organic solution of rhamnolipid calcium under reduced pressure to obtain 17g of rhamnolipid calcium powder with purity of 91.5%.
Example 3 preparation of rhamnolipid calcium starting from rhamnolipid solution:
500mL of 30 wt% rhamnolipid solution was placed in a 1000mL round bottom flask in a 95 ℃ oil bath, saturated CaCl was slowly added with stirring2Solution, such that the rhamnolipid: CaCl2And the reaction is stopped after 4 hours, wherein the molar ratio is approximately 1: 5. Centrifuging at 5000rmp for 30min to obtain crude rhamnolipid calcium precipitate. Drying the rhamnolipid precipitate, adding an organic solvent ethyl acetate 500ML for multiple times of dissolution, and centrifuging at the rotating speed of 5000rmp for 30min to obtain an organic solution of rhamnolipid. Distilling the organic solution of rhamnolipid calcium under reduced pressure to obtain 135g of rhamnolipid calcium powder with milk white color.
Example 4 preservation characteristics of rhamnolipid calcium powder:
135g of the rhamnolipid calcium powder obtained in example 5 above was put into a 250mL jar and, after storage at room temperature (20-30 degrees) for two months, weighed 125.5g, the color remained milky.
Example 5 use of rhamnolipid calcium powder as a cleaning product:
200g of rhamnolipid calcium powder is uniformly mixed with 10 g of talcum powder and 5g of baking soda to prepare the face washing powder which can be stored for a long time and does not need to be added with preservative. 2g of the face washing powder is dissolved in 100mL of tap water, the observed foaming property of the solution is strong, the face washing powder can be directly used for cleaning skin, and the skin feel after washing is good. The powder can be directly used as various cleaning products for personal care, household and the like, and no preservative or antibacterial agent is needed.
Example 6 use of rhamnolipid calcium powder as biopesticide:
the rhamnolipid calcium powder replaces a surfactant to be mixed with tricyclazole and a concave protruding rod to prepare 25% tricyclazole wettable powder, and the use effect is good.
Example 7 use of rhamnolipid calcium powder as cosmetic emulsifier:
the rhamnolipid calcium powder obtained in the example 3 is used for preparing the skin-care cream, and the skin-care cream is prepared from the following raw materials in percentage by weight:
5% -10% of 1, 3-butanediol;
3 to 8 percent of glycerin
10 to 15 percent of rhamnolipid calcium
Rhamnose 1.0-3.0%
1 to 4 percent of isohexadecane
1 to 4 percent of squalane
Xylitol 0.5-1.0%
1.5 to 3.5 percent of edible ethanol
Carbomer 0.5% -0.8%
0.3 to 0.5 percent of triethanolamine
0.05 to 0.2 percent of high molecular sodium hyaluronate
0.2 to 0.5 percent of preservative;
deionized water: balance of
The face cream prepared according to the formula is not sticky, has good spreading performance and good moistening effect, and has good use experience.
It should be understood that although the present invention has been described in connection with the preferred embodiments, it should be understood that they have been presented by way of illustration and description, and not limitation, and various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (10)
1. The rhamnolipid calcium is obtained by complexing rhamnolipid with calcium ions, and has a structural formula as follows:
wherein n, m, x and y are positive integers, and z and l are 0 or positive integers.
2. A method for preparing rhamnolipid calcium as claimed in claim 1, comprising the steps of:
(1) and (3) dropwise adding a calcium ion-containing solution into the rhamnolipid fermentation liquor or the rhamnolipid-containing solution under stirring, and centrifuging to obtain a crude rhamnolipid calcium precipitate.
(2) Dissolving the crude rhamnolipid calcium precipitate collected in the step (1) in an organic solvent, and centrifuging to remove impurities which cannot be dissolved in the organic solvent.
(3) Evaporating the organic solution of the rhamnolipid calcium collected in the step (2) to obtain rhamnolipid calcium powder.
3. The method for preparing rhamnolipid calcium according to claim 2, wherein the rhamnolipid fermentation broth or rhamnolipid-containing solution in the step (1) is first centrifuged to remove solid impurities.
4. The method for preparing rhamnolipid calcium according to claim 2, characterized in that the stirring manner in the step (1) is mechanical stirring.
5. The method for preparing rhamnolipid calcium according to claim 2, wherein the centrifugation conditions in step (1) are: centrifuging at 1000-5000rmp for 10-30 min.
6. The method for preparing rhamnolipid calcium according to claim 2, wherein the molar ratio of rhamnolipid and calcium ion in step (1) is 1: 1-1: 5, preferably, a 1: 1.2-1: 3.
7. the method for preparing rhamnolipid calcium according to claim 2, wherein the step (1) is performed by adding a solution containing calcium ions dropwise and reacting for 0.1-4 hours. The reaction temperature is 10-60 deg.C, preferably 20-50 deg.C.
8. The method for preparing rhamnolipid calcium according to claim 2, characterized in that the organic solvent in the step (2) is selected from methanol, ethanol, propanol, isopropanol, butanol, ethyl acetate, butyl acetate, etc., preferably methanol, ethanol, propanol, isopropanol and butanol are used as the organic solvent.
9. The method for preparing rhamnolipid calcium according to claim 2, characterized in that the evaporation step in the step (3) employs reduced pressure or atmospheric distillation.
10. Use of the rhamnolipid calcium of claim 1 in toiletries, cosmetics, surfactants.
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| KRUTIKA INVALLY，等: "A new approach for downstream purification of rhamnolipid biosurfactants", 《FOOD AND BIOPRODUCTS PROCESSING》 * |
| MINGLEI CHEN，等: "Influence of Calcium Ions on Rhamnolipid and Rhamnolipid/Anionic Surfactant Adsorption and Self-Assembly", 《LANGMUIR》 * |
| 聂麦茜: "《有机化学》", 31 January 2014, 冶金工业出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112108075A (en) * | 2020-08-19 | 2020-12-22 | 山东将军烟草新材料科技有限公司 | Pickering emulsifier and preparation method and application thereof |
| CN112108075B (en) * | 2020-08-19 | 2022-03-29 | 山东将军烟草新材料科技有限公司 | Pickering emulsifier and preparation method and application thereof |
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