CN117069582A - Method for synthesizing natural components of medical-grade beewax - Google Patents
Method for synthesizing natural components of medical-grade beewax Download PDFInfo
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- CN117069582A CN117069582A CN202311030231.2A CN202311030231A CN117069582A CN 117069582 A CN117069582 A CN 117069582A CN 202311030231 A CN202311030231 A CN 202311030231A CN 117069582 A CN117069582 A CN 117069582A
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- 235000013871 bee wax Nutrition 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 14
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 claims abstract description 86
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 59
- 235000021314 Palmitic acid Nutrition 0.000 claims abstract description 29
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000012166 beeswax Substances 0.000 claims abstract description 15
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000004927 clay Substances 0.000 claims description 5
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 claims description 4
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 claims description 3
- ZHXZNKNQUHUIGN-UHFFFAOYSA-N chloro hypochlorite;vanadium Chemical compound [V].ClOCl ZHXZNKNQUHUIGN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 3
- 239000000126 substance Substances 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- 238000011160 research Methods 0.000 abstract description 4
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 235000019966 white bee wax Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 description 27
- 239000002253 acid Substances 0.000 description 13
- 241000256844 Apis mellifera Species 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 235000012907 honey Nutrition 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- -1 C25 alkane Chemical class 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- ADVORQMAWLEPOI-XHTSQIMGSA-N (e)-4-hydroxypent-3-en-2-one;oxotitanium Chemical compound [Ti]=O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O ADVORQMAWLEPOI-XHTSQIMGSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229940038481 bee pollen Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 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 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007765 cera alba Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 description 2
- 229960002666 1-octacosanol Drugs 0.000 description 1
- 241000256837 Apidae Species 0.000 description 1
- 241000256846 Apis cerana Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000009341 apiculture Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007766 cera flava Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application provides a method for synthesizing natural components of medical-grade beeswax, and relates to the technical field of pharmaceutical chemicals. A method for synthesizing natural components of medicinal beeswax comprises: mixing triacontanol, palmitic acid, a catalyst and a solvent, heating, refluxing and preserving heat to perform a water separation reaction to obtain a reaction liquid; and (3) sequentially cooling, filtering, purifying, extracting, decoloring, concentrating and collecting the melissa palmitate. The method provided by the application has the advantages of simple process, simple post-treatment process, low-cost and easily-obtained raw materials, high yield and purity of the prepared product, high pharmaceutical activity, and can be used for quality research of medicinal white beewax, and in addition, the method has better application effect in industries such as cosmetics and the like.
Description
Technical Field
The application relates to the technical field of pharmaceutical chemical industry, in particular to a method for synthesizing natural components of medical-grade beeswax.
Background
The Cera flava is wax secreted by Apis cerana Fabricius or Apis mellifera belonging to Apidae, and is prepared by heating honeycomb in water, filtering, condensing to obtain wax or refining; the materials for extracting bee wax mainly come from the honeycomb of bees and the wax cover cut off when taking the honey contains honey, pollen, bee wax, cocoon skin, bee corpse and the like, and the purity of the bee wax extracted from different substances is different;
beeswax is a complex organic compound. The main components of beeswax (beeswax) can be divided into 4 general classes, namely esters, free acids, free alcohols and hydrocarbons. In addition, it contains trace volatile oil and pigment. The esters include melissa palmitate (about 80% of the total content of beeswax), melissa cerotic, and melissa arachidate; among the free acids are cerotic acid (about 15%), pyromellitic acid, montanic acid, melissic acid, phyllosilicic acid, arachic acid and neocerotic acid; the free alcohols include n-octacosanol and melissa alcohol; among hydrocarbons, there are C25 alkane, C27 alkane, C29 alkane, C31 alkane and unsaturated melissa alkene, and the components thereof are different depending on the species of bee, honey powder source plant, extraction method and the like.
The quality of the bee wax product obtained by the bee honey powder source plant adopted by the bee is different from that of the bee wax product obtained by the commercial bee because of the different bee-keeping technology and the commercial bee wax product obtained by the commercial bee honey source plant is different from that obtained by the commercial bee honey source plant in 50 years ago, and the bee wax can be seldom collected into products with the refractive index of 1.4410.
In view of this, the present application has been made.
Disclosure of Invention
The application aims to provide a method for synthesizing natural components of medical-grade beeswax so as to solve the problems.
In order to achieve the above purpose, the application adopts the following technical scheme:
the application provides a method for synthesizing natural components of medical-grade beewax, which comprises the following steps: mixing triacontanol, palmitic acid, a catalyst and a solvent, heating, refluxing and preserving heat to perform a water separation reaction to obtain a reaction liquid;
and (3) sequentially cooling, filtering, purifying, extracting, decoloring, concentrating and collecting the melissa palmitate.
The structural formula of the target product prepared by the synthesis method provided by the application is
Preferably, the purification comprises adding water and stirring for 15-30min, and standing for 15-30min;
alternatively, the stirring time may be any value between 15min, 18min, 20min, 25min, 28min and 30min, and the standing time may be any value between 15min, 17min, 20min, 25min, 27min and 30 min.
Preferably, the purified water consumption is 2-6 times of the triacontanol consumption;
alternatively, the purified water amount may be any value between 2 times, 3 times, 4 times, 5 times, and 6 times the triacontanol amount;
still more preferably, the amount of water used for purification is 3 times the amount of triacontanol used;
preferably, the decoloring temperature is 30-80 ℃ and the time is 0.5-4h;
alternatively, the decolorizing temperature may be any value between 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃ and 80 ℃ and the time may be any value between 0.5h, 1h, 1.5h, 2h, 2.5h, 3h, 3.5h and 4h;
further preferably, the decolorizing temperature is 50 ℃ for 1 hour;
preferably, the concentration is reduced pressure concentration, and the concentration vacuum degree P is less than or equal to minus 0.08Mpa;
further, the temperature of the concentration is 70-100 ℃;
alternatively, the temperature of the concentration may be any value between 70 ℃, 75 ℃, 80 ℃, 85 ℃, 90 ℃, 95 ℃, and 100 ℃;
still further, the temperature of the concentration is preferably 80 ℃.
Optionally, the equivalent molar ratio of the triacontanol to the palmitic acid is 1.0:1.0-1.1:1.0.
Preferably, the equivalent molar ratio of triacontanol to palmitic acid feed may be any value between 1.0:1.0, 1.02:1.0, 1.05:1.0, 1.08:1.0 and 1.1:1.0.
Further, it is preferable that the equivalent molar ratio of triacontanol to palmitic acid feed amount is 1.0:1.0.
Optionally, the catalyst is one or more of titanium acetylacetonate, zirconium oxychloride and vanadium oxychloride.
Preferably, the catalyst is used in an amount of 0.005 to 0.10 times by mass of the triacontanol;
alternatively, the catalyst may be used in an amount of any value between 0.005 times, 0.01 times, 0.02 times, 0.03 times, 0.04 times, 0.05 times, 0.06 times, 0.07 times, 0.08 times, 0.09 times, and 0.10 times the mass of the triacontanol;
further, the catalyst is preferably used in an amount of 0.03 times the mass of the triacontanol.
Optionally, the solvent is one or more of toluene, paraxylene, ortho-xylene and meta-xylene.
Preferably, the solvent is used in an amount of 1 to 10 times the mass of the triacontanol;
alternatively, the solvent may be used in an amount of any of 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 times the amount of the triacontanol;
further, the solvent amount is preferably 3 times the mass of triacontanol.
Optionally, the target temperature for heating is 100-150 ℃;
preferably, the target temperature of the temperature increase may be any value between 100 ℃, 105 ℃, 110 ℃, 115 ℃, 120 ℃, 125 ℃, 130 ℃, 135 ℃, 140 ℃, 145 ℃ and 150 ℃;
further preferably, the target temperature of the temperature increase is 110±3 ℃;
preferably, the time of the water splitting reaction is 12-120h.
Alternatively, the time of the water splitting reaction may be any value between 12h, 24h, 36h, 48h, 60h, 72h, 84h, 96h, 108h, and 120h.
Optionally, the target temperature of the cooling is less than or equal to 100 ℃; preferably, the target temperature of the cooling is 80 ℃.
Optionally, the decoloring agent used for decoloring is activated clay and/or activated carbon.
Preferably, the decoloring agent is used in an amount of 0.005 to 0.1 times by mass of the triacontanol.
Alternatively, the amount of the decoloring agent may be any value between 0.005 times, 0.01 times, 0.02 times, 0.03 times, 0.04 times, 0.05 times, 0.06 times, 0.07 times, 0.08 times, 0.09 times, and 0.10 times the mass of the triacontanol;
further, it is preferable that the amount of the decoloring agent is 0.03 times the mass of the triacontanol.
According to the synthesis method provided by the application, proper amount of triacontanol and palmitic acid are dehydrated and esterified in the presence of a catalyst and a solvent, and the produced water is separated, so that the reversible esterification reaction moves to a terminal point, and the triacontanol is basically reacted completely; cooling the reaction solution, extracting, decolorizing, refining, and concentrating to obtain bee wax main component of melissa palmitate with high purity, low acid value and light color; the refining method has simple process and complete reaction, does not need to specially design the refining process for removing the triacontanol, reduces the damage of the production process to the environment, has high purity and high yield of the obtained product, has low peroxide value and refractive index meeting the medicinal requirements, and can be used in the industries of cosmetics, foods and the like with special requirements.
Compared with the prior art, the application has the beneficial effects that:
the synthesis method of the natural components of the medical-grade beeswax, provided by the application, uses the industrially purified triacontanol and the palmitic acid as the initial raw materials, esterifies the raw materials through a specific process, refines the raw materials through an extraction and decoloration method, removes unreacted alcohol impurities and the like completely, and prepares the main component of the palmitic acid melissa ester in the high-purity white beeswax with the color of nearly colorless, low peroxide value, low acid value and low hydroxyl value. The prepared product has high yield, high purity, low peroxide value, acid value and hydroxyl value, high pharmaceutical activity and high scientific research value, and the molar yield can reach 97.2 percent, the purity can reach 98.5 percent, the peroxide value can be as low as 0.03, the acid value can be as low as 1.7 and the hydroxyl value can be as low as 1.3.
Detailed Description
Embodiments of the present application will be described in detail below with reference to specific examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present application and should not be construed as limiting the scope of the present application. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
In the embodiment of the application, commercial industrial grade or food grade palmitic acid and triacontanol are used as starting materials, and the triacontanol is selected to obtain the triacontanol with the content of more than 95% as a key starting material mainly through extracting and purifying the sugar cane wax or sugar cane sugar manufacturing sludge.
The raw material information and sources used in the specific examples are shown in the following table 1:
table 1 raw materials and reagents information table used in examples
| Sequence number | Raw materials | Purity/information | Source |
| 1 | Palmitic acid | Reagent grade | Alatine |
| 2 | Titanium acetylacetonate | Industrial grade | Pichia reagent |
| 3 | Zirconium oxychloride | Reagent grade | Guangdong Weng Hong reagent |
| 4 | Activated carbon | Pharmaceutical grade | Shanghai Jinhu active carbon |
| 5 | Activated clay | Industrial grade | Yang Huagong of the family Duckweed Country |
| 6 | Triacontanol | Industrial grade | Shanxi Benhe biology |
Example 1
The method for synthesizing the melissa palmitate natural component of the medical-grade beeswax comprises the following specific steps:
s1: 100g of triacontanol with 97.4 percent of content is added into a 500ml reaction bottle, 58.4g of palmitic acid is added, 2.0g of zirconium oxychloride and 300ml of toluene are added to form a mixed system;
s2: heating the mixed system obtained in the step S1 to 110+/-3 ℃ to reflux and divide water, and carrying out heat preservation and stirring reaction for 60 hours to divide the generated water halfway;
s3: after the reaction of S2 is completed, the reaction liquid is cooled to 80 ℃, filtered, 300ml of purified water is added, stirred for 20min, kept stand for 20min, an organic layer is obtained by extraction, 3g of active carbon is added into the extract, the mixture is stirred and decolorized for 30min at 50 ℃, filtered, concentrated under reduced pressure at 80 ℃ and P is less than or equal to minus 0.08Mpa, low-boiling substances are removed, cooled to room temperature, and a yellowish and fragrant-smell product is collected, namely, the medical-grade bee wax natural component melissa palmitate of a target product, and the refractive index of the product is 1.4411, which is obviously superior to that of the products in the prior art.
Example 2
The method for synthesizing the melissa palmitate natural component of the medical-grade beeswax comprises the following specific steps:
s1: 100g of triacontanol with the content of 98.2 percent, 58.4g of palmitic acid, 2.5g of titanyl acetylacetonate and 300ml of o-xylene are added into a 500ml reaction bottle to form a mixed system;
s2: heating the mixed system obtained in the step S1 to 143+/-3 ℃ to reflux and divide water, and carrying out heat preservation and stirring reaction for 36h to divide the generated water halfway;
s3: after the reaction of S2 is completed, the reaction liquid is cooled to 80 ℃, filtered, 300ml of purified water is added, stirred for 20min, kept stand for 20min, an organic layer is obtained by extraction, 3g of active carbon is added into the extract, the mixture is stirred and decolorized for 30min at 50 ℃, filtered, concentrated under reduced pressure at 90 ℃ and P less than or equal to-0.08 Mpa, low-boiling substances are removed, cooled to room temperature, and a faint yellow and fragrant-smell product is collected, namely the medical-grade bee wax natural component melissa palmitate of a target product.
Example 3
The method for synthesizing the melissa palmitate natural component of the medical-grade beeswax comprises the following specific steps:
s1: 100g of triacontanol with the content of 98.2 percent, 58.4g of palmitic acid, 1.5g of titanyl acetylacetonate and 300ml of paraxylene are added into a 500ml reaction bottle to form a mixed system;
s2: heating the mixed system obtained in the step S1 to 138+/-3 ℃ to enable the mixed system to flow back and separate water, carrying out heat preservation and stirring reaction for 72 hours, and separating the generated water halfway;
s3: after the reaction of S2 is completed, the reaction liquid is cooled to 80 ℃, filtered, 300ml of purified water is added, stirred for 20min, kept stand for 20min, an organic layer is obtained by extraction, 5g of activated clay is added into the extract, stirred and decolored for 30min at 50 ℃, filtered, concentrated under reduced pressure at 90 ℃ and P less than or equal to-0.08 Mpa, low-boiling substances are removed, cooled to room temperature, and a faint yellow and fragrant-smell product is collected, namely the medical-grade bee wax natural component melissa palmitate of a target product.
The products obtained in examples 1-3 were weighed and tested for the relevant parameters, the test results being shown in Table 2 below:
TABLE 2 Table of product parameters obtained in examples 1-3
As is clear from Table 2, the melissa palmitate produced in examples 1-3 provided by the present application has high yield, high product content, high purity, and low peroxide value, acid value and hydroxyl value.
Example 4
The method for synthesizing the melissa palmitate natural component of the medical-grade beeswax comprises the following specific steps:
s1: 100g of triacontanol with the content of 98.2 percent is added into a 500ml reaction bottle, then 58.43g of palmitic acid is added, namely, the equivalent molar ratio of the triacontanol to the palmitic acid is 1.0, 2.0g of titanyl acetylacetonate and 300ml of toluene are added, so that a mixed system is formed;
s2: heating the mixed system obtained in the step S1 to 110+/-3 ℃ to reflux and divide water, and carrying out heat preservation and stirring reaction for 72 hours to divide the generated water halfway;
s3: after the reaction of S2 is completed, cooling the reaction liquid to 80 ℃, filtering, adding 300ml of purified water, stirring for 25min, standing for 25min, extracting to obtain an organic layer, adding 5g of activated clay into the extract, stirring and decoloring for 30min at 50 ℃, filtering, concentrating under reduced pressure at 70 ℃ and P less than or equal to-0.08 Mpa, removing low-boiling substances, cooling to room temperature, and collecting a pale yellow and fragrant product of the melissa palmitate.
Example 5
The difference from example 4 is that S1 is added with 61.36g of palmitic acid, i.e. the equivalent molar ratio of triacontanol to palmitic acid charge is 1.05.
Example 6
The difference from example 4 is that S1 is added with 64.28g of palmitic acid, i.e. the equivalent molar ratio of triacontanol to palmitic acid charge is 1.1.
Comparative example 1
The difference from example 4 is that S1 is added with 55.51g of palmitic acid, i.e. the equivalent molar ratio of triacontanol to palmitic acid charge is 0.95.
The specific results of the parameters relating to the amounts of products to be examined obtained in examples 4 to 6 and comparative example 1 are shown in Table 3 below:
table 3 Table of the results of measurement of the parameters of the products obtained in examples 4 to 6 and comparative example 1
| Project | Equivalent molar ratio | Acid value | Hydroxyl number | Molar yield | Crude color |
| Example 4 | 1.00eq | 2.5 | 2.4 | 97.2％ | Yellowish light yellow |
| Example 5 | 1.05eq | 5.3 | 2.6 | 96.6％ | Yellowish light yellow |
| Example 6 | 1.10eq | 7.2 | 2.1 | 94.3％ | Yellowish light yellow |
| Comparative example 1 | 0.95eq | 1.7 | 5.9 | 91.3％ | Yellowish light yellow |
As can be seen from Table 3, when the palmitic acid equivalent of the feed is relatively small, the triacontanol is not completely reacted, and the hydroxyl value of the reaction product is relatively high; when the charging equivalent of palmitic acid is larger, the palmitic acid residue is more, and the acid value of the product is higher; when the equivalent weight of palmitic acid is 1.0eq, the reaction effect is best, and the acid value and the hydroxyl value of the product are both more preferable. And when the palmitic acid addition equivalent is too low, below the preferred range of the application, the molar yield of the product is reduced to 91.3%, which is significantly lower than the yield of the product of the example of the preferred equivalent ratio of the application.
The application provides a method for synthesizing natural components of medical-grade beeswax, which uses industrial purified triacontanol and palmitic acid as starting materials, adopts high-purity triacontanol obtained by purifying sucrose wax, esterifies the triacontanol by a specific process, refines the triacontanol by extraction and decoloration methods, removes unreacted complete alcohol impurities and the like, and prepares the main component of the high-purity white beeswax with nearly colorless color, low peroxide value, low acid value and low hydroxyl value.
The preparation process of the natural components of the medical-grade bee wax is also suitable for synthesizing the bee pollen ester of the cerotic acid and the bee pollen ester of the arachidic acid, has mild reaction conditions, can intermittently and rapidly produce wax substances, and obtains high-purity bee wax products with high content and less impurities, and the obtained high-purity bee pollen ester of the palmitic acid can be used for scientific research, research on bee wax impurities and the like.
While certain specific embodiments of the application have been described in detail by way of example, it will be appreciated by those skilled in the art that the above examples are for illustration only and are not intended to limit the scope of the application. It will be appreciated by those skilled in the art that modifications may be made to the above embodiments without departing from the scope and spirit of the application. The scope of the application is defined by the appended claims.
Claims (10)
1. A method for synthesizing a natural component of pharmaceutical grade beeswax, comprising: mixing triacontanol, palmitic acid, a catalyst and a solvent, heating, refluxing and preserving heat to perform a water separation reaction to obtain a reaction liquid;
and (3) sequentially cooling, filtering, purifying, extracting, decoloring, concentrating and collecting the melissa palmitate.
2. The method of claim 1, wherein the equivalent molar ratio of triacontanol to palmitic acid is 1.0:1.0 to 1.1:1.0.
3. The method according to claim 1, wherein the catalyst is one or more of titanium acetylacetonate, zirconium oxychloride, and vanadium oxychloride.
4. A synthetic method according to claim 3 wherein the catalyst is used in an amount of 0.005 to 0.10 times the mass of the triacontanol.
5. The method of claim 1, wherein the solvent is one or more of toluene, para-xylene, ortho-xylene, meta-xylene.
6. The method according to claim 5, wherein the solvent is used in an amount of 1 to 10 times by mass of the triacontanol.
7. The synthetic method of claim 1 wherein the elevated target temperature is 100-150 ℃;
preferably, the time of the water splitting reaction is 12-120h.
8. The method according to claim 1, wherein the target temperature of the temperature decrease is 100 ℃ or less.
9. The method according to any one of claims 1 to 8, wherein the decolorizing agent used is activated clay and/or activated carbon.
10. The synthetic method according to claim 9, wherein the decoloring agent is used in an amount of 0.005 to 0.1 times by mass of the triacontanol.
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