CN117737157A - Preparation method of sucrose lauric acid diester - Google Patents
Preparation method of sucrose lauric acid diester Download PDFInfo
- Publication number
- CN117737157A CN117737157A CN202410158113.8A CN202410158113A CN117737157A CN 117737157 A CN117737157 A CN 117737157A CN 202410158113 A CN202410158113 A CN 202410158113A CN 117737157 A CN117737157 A CN 117737157A
- Authority
- CN
- China
- Prior art keywords
- sucrose
- laurate
- lipase
- diester
- sucrose laurate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 sucrose lauric acid diester Chemical class 0.000 title claims abstract description 49
- 229930006000 Sucrose Natural products 0.000 title claims description 44
- 239000005720 sucrose Substances 0.000 title claims description 44
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 title claims description 12
- 239000005639 Lauric acid Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title abstract description 8
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- 108090001060 Lipase Proteins 0.000 claims abstract description 16
- 239000004367 Lipase Substances 0.000 claims abstract description 16
- 102000004882 Lipase Human genes 0.000 claims abstract description 16
- 235000019421 lipase Nutrition 0.000 claims abstract description 16
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 22
- 239000002808 molecular sieve Substances 0.000 claims description 16
- 229940040461 lipase Drugs 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 14
- GCSPRLPXTPMSTL-IBDNADADSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GCSPRLPXTPMSTL-IBDNADADSA-N 0.000 claims description 13
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 9
- 108010048733 Lipozyme Proteins 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 8
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 claims description 6
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 4
- 241000228245 Aspergillus niger Species 0.000 claims description 3
- 241000222175 Diutina rugosa Species 0.000 claims description 3
- 108010084311 Novozyme 435 Proteins 0.000 claims description 3
- 102000019280 Pancreatic lipases Human genes 0.000 claims description 3
- 108050006759 Pancreatic lipases Proteins 0.000 claims description 3
- 101001003495 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 3
- 101001064559 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 3
- 229940116369 pancreatic lipase Drugs 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 7
- 230000002829 reductive effect Effects 0.000 abstract description 7
- 239000012429 reaction media Substances 0.000 abstract description 5
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000002752 melanocyte Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007036 catalytic synthesis reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 238000000956 solid--liquid extraction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
The invention discloses a preparation method of sucrose laurate diester, which adopts lipase as a catalyst to catalyze and synthesize the sucrose laurate diester, the method is not required to be carried out under the conditions of high temperature or reduced pressure, the reaction condition is mild, the safety is high, and the method adopts low-toxicity and easily-separated tertiary amyl alcohol or tertiary butyl alcohol as a reaction medium, so that the sucrose laurate diester is easy to separate and purify, the production cost is reduced, and the method is more environment-friendly.
Description
Technical Field
The invention relates to the technical field of preparation of sucrose fatty acid ester, in particular to a preparation method of sucrose lauric acid diester.
Background
Sucrose ester, also called sucrose fatty acid ester, is a nonionic surfactant, has the advantages of no toxicity, good biocompatibility, no irritation, biodegradability and the like, and is widely applied to industries such as food, daily chemicals, pharmacy and the like.
The sucrose laurate diester is one of sucrose esters, and researches show that the sucrose laurate diester can influence melanin generation and dendritic properties of melanocytes through a new metabolic pathway, and can obviously reduce bilirubin level, thereby playing roles in whitening and brightening skin color, and being a cosmetic raw material with wide application prospect.
At present, the sucrose fatty acid ester is industrially produced mainly by a chemical method, for example, the invention patent with the application publication number of CN 116751236A discloses a preparation method of sucrose fatty acid diester, which comprises the following steps: (1) Adding sucrose, fatty acid methyl ester and a catalyst (potassium carbonate or potassium hydroxide) into a solvent, and carrying out transesterification under the condition of reduced pressure at 70-120 ℃ to obtain a sucrose fatty acid ester crude product; (2) Concentrating, purifying and separating the sucrose fatty acid ester crude product to obtain the sucrose fatty acid diester. The solvent is N, N-dimethylformamide, dimethyl sulfoxide, mixture of N, N-dimethylformamide and toluene or mixture of N, N-dimethylformamide and tetrahydrofuran. The method can prepare sucrose fatty acid diester, but has harsh reaction conditions, and uses organic solvents with high toxicity, such as dimethyl sulfoxide and the like, which are difficult to separate as reaction media, thereby increasing the difficulty of separating and purifying the product, increasing the cost and limiting the application of sucrose ester in the fields of foods, cosmetics and the like.
Therefore, there is a need to provide a method for preparing sucrose laurate diester with mild, green and safe reaction conditions.
Disclosure of Invention
In order to solve the problems, the invention provides a preparation method of sucrose laurate diester, which is green, efficient, safe and low in cost.
The technical scheme for solving the problems is as follows:
a method for preparing sucrose laurate diester, comprising the following steps:
s1, respectively dehydrating sucrose, a substrate and a solvent;
s2, adding sucrose dehydrated in the step S1 and a substrate into the dehydrated solvent in the step S1, uniformly stirring, adding lipase and a molecular sieve, and reacting to obtain a sucrose ester crude product;
s3, purifying and separating the sucrose ester crude product in the step S2 to obtain sucrose lauric acid diester;
the substrate is selected from one or more of vinyl laurate, methyl laurate, ethyl laurate and lauric acid.
According to the preparation method, water is generated during the reaction, the inventor respectively dehydrates sucrose, a substrate and a solvent in advance, and adds a molecular sieve into a reaction system to remove the water generated during the reaction, so that the reaction is promoted to be carried out in the direction of generating the sucrose laurate diester, and the yield of the sucrose laurate diester is improved.
Wherein sucrose and lauric acid can be dehydrated using molecular sieves, preferablyA molecular sieve; vinyl laurate, methyl laurate, ethyl laurate and solvents may be dehydrated with anhydrous sodium sulfate.
The lipase is used as the catalyst, so that the enzyme dosage is small, and the lipase can be recycled after the reaction is finished, thereby reducing the cost.
Preferably, the solvent is at least one selected from tertiary amyl alcohol and tertiary butyl alcohol.
Tertiary butanol and tertiary amyl alcohol are low-toxicity, low-boiling point and easy-to-separate solvents, and the tertiary butyl alcohol and the tertiary amyl alcohol are used as reaction media, so that the safety of the reaction can be improved, and the difficulty of subsequent separation and purification of products is reduced; in addition, because the reaction medium does not contain toxic organic solvents such as DMSO and the like, the prepared sucrose laurate diester can be applied to the fields such as foods, cosmetics and the like with high requirements on raw material safety.
Preferably, the lipase is selected from one or more of Lipozyme TL IM, novozym 435, candida rugosa lipase, pseudomonas fluorescens lipase, aspergillus niger lipase, porcine pancreatic lipase.
Preferably, the molar ratio of sucrose to substrate in step S2 is (0.8-2.4): 1.5-3.5.
Preferably, the lipase in step S2 is 1.5-34% of the sucrose.
Preferably, 18 to 50mL of the solvent is used for every 1g of sucrose in the step S2.
Preferably, the reaction temperature in the step S2 is 60-75 ℃, and the reaction time is 12-48 hours.
The reaction of the invention is not needed to be carried out under the conditions of high temperature and reduced pressure, the reaction condition is mild, the energy consumption is low, and the cost is low.
Preferably, the purification method in step S3 is to extract the sucrose ester crude product, collect the organic phase, and then separate the organic phase.
The extraction may be solid-liquid extraction or liquid-liquid extraction, and the extraction solvent may be a mixture of n-butanol and aqueous NaCl solution.
The separation can be carried out by a column chromatography separation method, wherein the column chromatography silica gel is preferably 200-300 meshes.
The invention also provides the sucrose laurate diester prepared by the method.
The sucrose laurate diester can be used as a nonionic surfactant, and can be used as a cosmetic raw material, such as a formula of SDL color light forest, because the sucrose laurate diester can influence melanin generation and dendritic properties of melanocytes, and the sucrose laurate diester can be used for inhibiting the dendritic overactivity of the melanocytes so as to achieve the effects of removing spots and whitening.
The invention has the following beneficial effects:
the method adopts lipase as a catalyst to catalyze and synthesize the high-purity sucrose laurate, the method does not need to be carried out under the conditions of high temperature and reduced pressure, the reaction condition is mild, the safety is high, and the method adopts low-toxicity and easily-separated tertiary amyl alcohol or tertiary butanol as a reaction medium, so that the sucrose laurate is easy to separate and purify, the production cost is reduced, and the method is more environment-friendly.
Drawings
FIG. 1 is a high performance liquid chromatogram of catalytic synthesis of sucrose laurate diester in t-amyl alcohol in example 2;
FIG. 2 is a thin layer chromatogram of the reaction monitoring in a 65℃group round bottom flask of example 3;
FIG. 3 is a high resolution mass spectrum of sucrose laurate after purification by silica gel column chromatography in example 4.
Detailed Description
The present embodiments are merely illustrative of the invention and not limiting of the invention, and any changes made by those skilled in the art after reading the specification of the invention will be protected by the patent laws within the scope of the claims.
Example 1
The tert-amyl alcohol and vinyl laurate are dehydrated by anhydrous sodium sulfate. Will beThe molecular sieve is firstly activated in a muffle furnace at 350 ℃ for 6 hours, then is cooled to 120 ℃ along with the muffle furnace, and is taken out and put into a dryer. Will->The molecular sieve and crystalline sucrose ground to powder are dried in vacuo for 12h.
6 50mL round bottom flasks, numbered 1, 2, 3, 4, 5 and 6, were each charged with 15mL t-amyl alcohol, 1.81mmol (470. Mu.L) vinyl laurate, 0.4g treated sucrose, stirred in a 60℃water bath for 1h, and 0.4g each was charged to each round bottom flaskAfter molecular sieves, 0.1g Lipozyme TL IM was added to round bottom flask number 1, 0.1g Novozym 435 was added to round bottom flask number 2, 0.1g Candida rugosa lipase was added to round bottom flask number 3, 0.1g Pseudomonas fluorescens lipase was added to round bottom flask number 4, 0.1g Aspergillus niger lipase was added to round bottom flask number 5, 0.1g porcine pancreatic lipase was added to round bottom flask number 6, and all 6 round bottom flasks were reacted in a water bath at 60℃for 12h. After the reaction, the concentration of sucrose lauric acid diester was 9.1 by HPLC,6.7, 2.4, 1.3, 0.8, 0.4g/L, and the results showed that when Lipozyme TL IM was used as a catalyst, the sucrose laurate yield was the highest, 9.1g/L.
Example 2
The tert-amyl alcohol, tert-butyl alcohol and vinyl laurate are dehydrated with anhydrous sodium sulfate. Will beThe molecular sieve is firstly activated in a muffle furnace at 350 ℃ for 6 hours, then is cooled to 120 ℃ along with the muffle furnace, and is taken out and put into a dryer. Will->The molecular sieve and crystalline sucrose ground to powder are dried in vacuo for 12h.
2 50mL round bottom flasks, numbered 1 and 2, were each charged with 0.3g of treated sucrose, 1.81mmol of vinyl laurate, 15mL of t-amyl alcohol in round bottom flask 1, 15mL of t-butanol in round bottom flask 2, stirred in a 60℃water bath for 1h, 0.1g of Lipozyme TL IM and 0.4g of molecular sieve in each round bottom flask, and reacted in a 60℃water bath for 12h.
After the reaction was completed, the concentration of sucrose laurate diester in the tertiary butanol system was 9.8g/L and the concentration of sucrose laurate diester in the tertiary amyl alcohol system was 10.1g/L as determined by HPLC. FIG. 1 is a high performance liquid chromatogram of catalytic synthesis of sucrose laurate diester in t-amyl alcohol using Lipozyme TL IM as a catalyst, as can be seen from FIG. 1, the sucrose laurate diester concentration is relatively high and easy to separate.
Example 3
The tert-amyl alcohol and vinyl laurate are dehydrated by anhydrous sodium sulfate. Will beThe molecular sieve is firstly activated in a muffle furnace at 350 ℃ for 6 hours, then is cooled to 120 ℃ along with the muffle furnace, and is taken out and put into a dryer. Will->MoleculesThe crystalline sucrose, which was sieved and ground to powder, was dried in vacuo for 12h.
Taking 5 50mL round bottom flasks numbered No. 1 and No. 2, no. 3, no. 4 and No. 5, adding 1.81mmol of vinyl laurate, 0.4g of treated sucrose and 15mL of tertiary amyl alcohol into each round bottom flask, stirring for 1h in a water bath at 60 ℃, and adding 0.03g of Lipozyme TL IM and 0.4g of Lipozyme TL IM into each round bottom flaskMolecular sieves were reacted in water baths at 50, 55, 60, 65, 70 ℃ for 24h, respectively. The progress of the reaction was monitored by thin layer chromatography, and FIG. 2 is a graph showing the results of the reaction in a 65℃group round-bottomed flask, which shows that the color gradually increases from A to D, indicating that the concentration of sucrose laurate in the reaction system gradually increases with time.
After the reaction, the concentration of the sucrose laurate diester in 5 round bottom flasks was 25.1, 27.2, 35.2, 35.6 and 29.6g/L respectively as measured by HPLC, and as a result, the yield of the sucrose laurate diester was increased and then decreased in the temperature range of 50-70 ℃, wherein the yield of the sucrose laurate diester was higher at 60-65 ℃.
Example 4
After the completion of the catalytic reaction in a No. 4 round-bottomed flask placed in a water bath at 65℃in example 3, the organic phase of the upper layer was extracted with a biphasic system comprising n-butanol-5 wt% NaCl, dried over anhydrous sodium sulfate, filtered and depressurized. The silica gel with 200-300 meshes is used as a stationary phase, a wet method is used for filling a column, a solution of toluene, ethyl acetate, methanol and water in a volume ratio of 260:15:40:10 is used as a developing agent, TLC (thin layer chromatography) is used for tracking and collecting eluent with an Rf value of 0.3-0.5, the collected eluent is decompressed and removed of the solvent, and high-purity sucrose laurate diester is obtained, and a result is shown in figure 3.
Comparative example 1
The tert-amyl alcohol and vinyl laurate are dehydrated by anhydrous sodium sulfate. Will beThe molecular sieve is firstly activated in a muffle furnace at 350 ℃ for 6 hours and then is followed by the muffle furnaceCooled to 120 ℃, taken out and put into a dryer. Will->The molecular sieve and crystalline sucrose ground to powder are dried in vacuo for 12h.
A50 mL round bottom flask was charged with 0.3g of treated sucrose, 1.81mmol (470. Mu.L) of vinyl laurate and 15mL of t-amyl alcohol, stirred in a 60℃water bath for 1h, and then 0.4g was addedMolecular sieve, in a water bath kettle at 60 ℃ for 12h. After the reaction was completed, no sucrose laurate diester was formed by HPLC. From the results, it can be seen that sucrose and vinyl laurate cannot react to form sucrose laurate diester without a catalyst.
Claims (9)
1. A method for preparing sucrose laurate diester, which is characterized by comprising the following steps:
s1, respectively dehydrating sucrose, a substrate and a solvent;
s2, adding sucrose dehydrated in the step S1 and a substrate into the dehydrated solvent in the step S1, uniformly stirring, adding lipase and a molecular sieve, and reacting to obtain a sucrose ester crude product;
s3, purifying and separating the sucrose ester crude product in the step S2 to obtain sucrose lauric acid diester;
the substrate is selected from one or more of vinyl laurate, methyl laurate, ethyl laurate and lauric acid.
2. The method for producing sucrose laurate according to claim 1, wherein the solvent is at least one selected from the group consisting of t-amyl alcohol and t-butyl alcohol.
3. The method for preparing sucrose laurate according to claim 1, wherein the lipase is selected from one or more of Lipozyme TLIM, novozym 435, candida rugosa lipase, pseudomonas fluorescens lipase, aspergillus niger lipase, and porcine pancreatic lipase.
4. The method for producing a sucrose laurate according to claim 1, wherein the molar ratio of sucrose to substrate in step S2 is (0.8-2.4): 1.5-3.5.
5. The method for producing sucrose laurate according to claim 1, wherein the lipase in step S2 is 1.5-34% of the sucrose.
6. The method for producing sucrose laurate according to claim 1, wherein 18-50 mL of the solvent is used per 1g of sucrose in the step S2.
7. The method for preparing sucrose laurate according to claim 1, wherein the reaction temperature in the step S2 is 60-75 ℃ and the reaction time is 12-48 h.
8. The method for preparing sucrose laurate according to claim 1, wherein the purification in step S3 is performed by extracting the sucrose ester crude product, collecting the organic phase, and separating the organic phase.
9. Sucrose laurate prepared by the method of any one of claims 1-8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410158113.8A CN117737157A (en) | 2024-02-04 | 2024-02-04 | Preparation method of sucrose lauric acid diester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410158113.8A CN117737157A (en) | 2024-02-04 | 2024-02-04 | Preparation method of sucrose lauric acid diester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117737157A true CN117737157A (en) | 2024-03-22 |
Family
ID=90278076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410158113.8A Pending CN117737157A (en) | 2024-02-04 | 2024-02-04 | Preparation method of sucrose lauric acid diester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117737157A (en) |
-
2024
- 2024-02-04 CN CN202410158113.8A patent/CN117737157A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5353983B2 (en) | Capsinoid production method by dehydration condensation, capsinoid stabilization method, and capsinoid composition | |
| CN103228640B (en) | The preparation process of nebivolol | |
| US7052886B2 (en) | Process for the isolation of lovastatin | |
| JP4168170B2 (en) | Arbutin ester compound and method for producing the same | |
| CN117737157A (en) | Preparation method of sucrose lauric acid diester | |
| EP1634958B1 (en) | Method for producing optically active chroman-carboxylate | |
| CN110128246B (en) | Preparation method of hydroxytyrosol | |
| CN109020816B (en) | Method for obtaining 3-hydroxy-2, 2, 4-trimethyl pentanoic acid-2-methyl propyl ester from alcohol ester twelve-process wastewater | |
| CN112358514A (en) | Synthesis process of arbutin | |
| CN105296554B (en) | Combined-enzyme method prepares the preparation method of pneumatically conveying | |
| EP4034540B1 (en) | Method of making and/or isolating isoidide, comprising selective esterification of a mixture of dianhydrohexitol isomers | |
| US5256800A (en) | Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for preparing same | |
| CN113061084B (en) | Novel method for preparing ferulic acid | |
| WO2005033149A1 (en) | Receptor specific binder discovery using intramolecular acyl migration induced dynamic carbohydrate library | |
| CN116904533A (en) | Preparation method of (R) -5, 7-difluoro-3, 4-dihydro-2H-1-benzopyran-4-ol | |
| EP1445324A1 (en) | Process for producing optically active chroman derivative and intermediate | |
| KR0150287B1 (en) | Process for producing optically active 2-phenyl-1,3-propanediol derivatives | |
| CN117209379A (en) | Preparation method of tyrosol laurate, catalyst for preparation and preparation method of catalyst | |
| CN118206450A (en) | Method for synthesizing 3-hydroxybutyric acid glyceride | |
| JP2689211B2 (en) | Process for producing optically active 3-hydroxytetradecanoic acid ester | |
| CN102031278B (en) | Method for enzymatic synthesis of trehalose unsaturated fatty acid diester in organic phase | |
| Schick et al. | Synthesis of Alkyl (±)‐2, 3‐Di‐O‐acylglycerates and Attempts Directed to their Conversion into Alkyl (R)‐2, 3‐Di‐O‐acylglycerates by Enzyme‐catalyzed Enantioselective Deacylation Reactions [1] | |
| CN112266328A (en) | Synthetic route and preparation method of 3-fluoro-4-nitrobenzaldehyde | |
| OR | WHPh | |
| JPH06335398A (en) | Cyclohexenediol derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |