CN112961056A - Preparation method and application of glycerol triacetate - Google Patents
Preparation method and application of glycerol triacetate Download PDFInfo
- Publication number
- CN112961056A CN112961056A CN202110147281.3A CN202110147281A CN112961056A CN 112961056 A CN112961056 A CN 112961056A CN 202110147281 A CN202110147281 A CN 202110147281A CN 112961056 A CN112961056 A CN 112961056A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- glycerol
- ex146h
- water
- particle size
- 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
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
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
- A24D3/10—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent of cellulose or cellulose derivatives
Abstract
The invention provides a preparation method and application of glycerol triacetate, and relates to the technical field of chemical synthesis. The preparation method comprises the following steps: glycerol and acetic acid are used as raw materials, and esterification reaction is carried out in the presence of a catalyst and a water-carrying agent to obtain glycerol triacetate; the catalyst is one or more of EX146H, D61, D72, Amberlyst-15, Nafion 511 and Amberlite IR-120, the water-carrying agent is one or more of benzene, toluene, cyclohexane, chloroform, n-propyl acetate, isopropyl acetate and carbon tetrachloride, and the yield and purity of the triacetyl glycerine are obviously improved by controlling the types of the catalyst and the water-carrying agent and the particle size of the catalyst in the implementation process.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, and particularly relates to a preparation method and application of glycerol triacetate.
Background
Glycerol triacetate, also known as triacetin, having a molecular formula of C9H14O6Molecular weight of 218.21, is colorless and slightly bitter at room temperature, and can be mixed with ethanol, diethyl ether, chloroform and benzeneMost of organic solvents are miscible, can be dissolved in acetone, are insoluble in mineral oil and can be partially dissolved in water, the solubility in water at 20 ℃ is 64.0g/L, the organic solvent is a good solvent, plasticizer and humectant, the organic solvent is widely used in industries such as food, spice, printing and dyeing and tobacco industry, the annual consumption amount reaches more than ten thousand tons, and the demand is huge.
Glyceryl triacetate is a bulk chemical, and has very wide application in industry. At present, the glycerol triacetate is mainly used as a plasticizer, and researches show that the addition amount of the glycerol triacetate in the cigarette cellulose acetate filter stick directly influences the hardness, the pressure drop and the like of the filter stick, further influences the filtering efficiency of the filter tip on harmful substances such as phenols, aldehydes and the like, and is only calculated by ten thousand tons in four tobacco groups in China; meanwhile, the glycerol triacetate as a plasticizer can improve the thermal stability of the starch ester film matrix, and is beneficial to further improvement and application of the hydrophobic biodegradable packaging material in different environments. In the field of medicine, glyceryl triacetate itself can be used as an active ingredient of antifungal drugs for treating onychomycosis and fungal infection of the skin surface layer; in addition, the compound can also be used as a penetration enhancer of medicines, and is beneficial to the penetration and site-specific release of the medicines. In the food industry, can be used as food additive; can also be used as acidifier of animal feed, and can effectively inhibit growth of harmful bacteria, promote reproduction of beneficial bacteria, and ensure health growth of livestock by changing pH value of gastrointestinal tract of livestock due to different living environments of different bacteria. In the cosmetics industry, glyceryl triacetate acts as a bactericide, plasticizer and solvent in perfume and fragrance formulations, and the concentration in these cosmetics is usually maintained between 0.8 and 4%. The research also shows that the glycerol triacetate is used as the additive of the diesel oil, so that the low-temperature fluidity of the oil product can be improved, the octane number of the oil product can be improved, the anti-explosion performance of the oil product can be improved, the engine efficiency can be improved, and the emission of nitrogen oxides in tail gas can be reduced.
The method for preparing the glycerol triacetate by taking the glycerol as the raw material is the most classical preparation method, concentrated sulfuric acid or toluenesulfonic acid is used as a catalyst, but the concentrated sulfuric acid is used as the catalyst, so that equipment is easily corroded, the equipment loss is large, more waste acid is generated in production, the environment is easily polluted, the reaction time is long, more byproducts are generated, and the product yield is not high.
For example, chinese patent application 201610515687.1 discloses a method for preparing triacetin, which comprises using glycerol and acetic acid as main reaction raw materials, adding a catalyst and a dehydrating agent, carrying out two-step esterification, neutralizing the corresponding acid solution to obtain a crude product, further carrying out nitrogen pressure filtration to obtain a refined product, using sulfuric acid as a catalyst in the reaction, which causes problems of high corrosion to equipment, more side reactions, difficult subsequent separation and purification, and poor yield and quality of the obtained product.
Further, as disclosed in chinese patent application 202010249675.5, a method for preparing triacetin comprises subjecting glycerol and acetic acid to esterification reaction in the presence of a modified porous medium supported heteropolyacid catalyst and a water-carrying agent to obtain triacetin, wherein the heteropolyacid is Ag3PW12O40 and/or Ag3PW12O40(ii) a The porous medium is diatomite or montmorillonite. Compared with the traditional liquid acid, the modified porous medium loaded heteropoly acid catalyst adopted by the invention is milder, low in toxicity and environment-friendly, and meanwhile, the catalytic activity is high, the dosage is small, the process is simple, the steps of acylation, neutralization and the like are not needed, the cost is saved, the yield of the prepared glyceryl triacetate is high, and the production efficiency is improved; however, this application does not focus on the purity of the obtained triacetin.
Therefore, the development of a preparation method of triacetyl glycerine with short reaction time and high yield and purity and the application of the triacetyl glycerine in cigarette cellulose acetate filter sticks are needed.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of glycerol triacetate, which takes cation exchange resin as a catalyst and uses a mixed solvent as a water-carrying base, and can obviously improve the conversion rate of glycerol in the reaction process and obviously improve the purity and yield of the obtained glycerol triacetate.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention discloses a preparation method of glycerol triacetate.
Wherein the catalyst is cation exchange resin catalyst, and the cation exchange resin catalyst is selected from one or more of EX146H, D61, D72, Amberlyst-15, Nafion 511 and Amberlite IR-120;
preferably, the cation exchange resin catalyst is selected from one or more of EX146H, D72, Nafion 511 and Amberlite IR-120;
still preferably, the cation exchange resin catalyst is selected from one or more of EX146H, D72 and Nafion 511;
further preferably, the cation exchange resin catalyst is a mixture of EX146H and D72;
the mass ratio of EX146H to D72 is 2-5: 1; the mass ratio of EX146H to D72 is 2:1, 3: 1. 4: 1 or 5: 1; preferably 3: 1.
The water-carrying agent is one or more of benzene, toluene, cyclohexane, n-propyl acetate, isopropyl acetate, chloroform and carbon tetrachloride;
preferably, the water-carrying agent is one or more of toluene, cyclohexane, n-propyl acetate, isopropyl acetate, chloroform and carbon tetrachloride;
preferably, the water-carrying agent is one or more of cyclohexane, n-propyl acetate, isopropyl acetate and carbon tetrachloride;
further preferably, the water-carrying agent is a mixture of cyclohexane and n-propyl acetate; the volume ratio of the cyclohexane to the n-propyl acetate is 5-10: 1; the volume ratio of the cyclohexane to the n-propyl acetate is 5:1, 6: 1. 7: 1. 8: 1. 9: 1 or 10: 1; preferably 10: 1.
The particle size of the catalyst is 0.8-1.20 mm; the particle size of the catalyst is 0.8mm, 0.9mm, 1.0mm, 1.1mm or 1.2 mm;
the invention unexpectedly discovers that the conversion rate of the glycerol can be promoted by simultaneously using catalysts with different particle sizes in the implementation process;
in some preferred embodiments, the EX146H catalyst has a particle size of 0.8 to 1.0 mm; the particle size of the D72 catalyst is 1.0-1.2 mm;
preferably, the particle size of the EX146H catalyst is 0.9-1.0 mm; the particle size of the D72 catalyst is 1.1-1.2 mm;
still preferably, the particle size of the EX146H catalyst is 1.0 mm; the particle size of the D72 catalyst was 1.2 mm.
The molar ratio of the acetic acid to the glycerol is 4-6: 1; preferably, the molar ratio of acetic acid to glycerol is 4.5-5.5: 1; still more preferably, the molar ratio of acetic acid to glycerol is 5: 1.
the mass ratio of the catalyst to the glycerol is 0.15-0.35: 100, respectively; preferably 0.20 to 0.30: 100, respectively; still more preferably 0.25: 100.
the mass ratio of the glycerol to the water-carrying agent is 100: 1.2-1.5; preferably 100: 1.3-1.5; more preferably 100: 1.4-1.5; more preferably 100: 1.5.
the reaction temperature of the esterification reaction is 80-95 ℃; preferably, the reaction temperature is 85-95 ℃; more preferably, the reaction temperature is 90-95 ℃; further preferably, the reaction temperature is 95 ℃.
Purifying the product to obtain the finished product of glycerol triacetate. The purification method comprises the following steps: and (3) cooling the reaction liquid to room temperature after the esterification reaction is finished, distilling at normal pressure to remove excessive acetic acid, distilling under reduced pressure to concentrate to remove the water-carrying agent, and separating to obtain glycerol triacetate.
The invention also provides application of the glycerol triacetate in preparing a cigarette filter stick.
Compared with the prior art, the invention has the beneficial effects that:
(1) the invention uses cation exchange resin as catalyst, which can obviously improve the conversion rate of glycerol, and the invention unexpectedly finds that the mixture of EX146H and D72 is used as catalyst, and the mass ratio of the EX146H to the D72 is controlled to be 2-5:1, which can obviously improve the purity of the product;
(2) according to the invention, the particle size of the catalyst is researched, and the discovery that the two catalysts with different particle sizes are used simultaneously can effectively weaken the internal diffusion of reactants in the cation exchange resin catalyst in the reaction process and improve the reaction efficiency;
(3) in the implementation process, the mixture of two solvents is used as a water-carrying agent, and the volume ratio of the two solvents is controlled, so that the conversion rate of the glycerol is obviously improved, and the yield of the product is improved.
(4) By selecting the catalyst and the water-carrying agent, the invention obviously improves the reaction efficiency, reduces the reaction temperature and ensures that the yield and the purity of the obtained glycerol triacetate are higher than those of the prior art.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The source of the reagent used in the present invention is not limited, and the reagents used in the present invention are all commercially available products in the art, and all the reagents used are AR, unless otherwise specified.
Example 1A method for preparing glyceryl triacetate
46.045g of glycerol (0.5mol), 121g of acetic acid (2mol), 0.0690g of catalyst and 552.54mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 10 hours at 80 ℃, after the reaction is finished, the reaction solution is distilled under normal pressure to remove excessive acetic acid, and then reduced pressure distillation is carried out to obtain the glycerol triacetate.
The catalyst is EX146H and D72 with the mass ratio of 2:1, and the particle size of the EX146H catalyst is 0.8 mm; the particle size of the D72 catalyst is 1.0 mm;
the water-carrying agent is cyclohexane and n-propyl acetate with the volume ratio of 5: 1.
Example 2 preparation method of glyceryl triacetate
46.045g of glycerol (0.5mol), 138.135g of acetic acid (3mol), 0.162g of catalyst and 690.675mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 95 ℃, excessive acetic acid is removed from reaction liquid by normal pressure distillation after the reaction is finished, and then glycerol triacetate is obtained by reduced pressure distillation.
The catalyst is EX146H and D72 with the mass ratio of 5:1, and the particle size of the EX146H catalyst is 0.9 mm; the particle size of the D72 catalyst is 1.1 mm;
the water-carrying agent is cyclohexane and n-propyl acetate with the volume ratio of 10: 1.
Example 3 preparation method of glyceryl triacetate
46.045g of glycerol (0.5mol), 115.1125g of acetic acid (2.5mol), 0.115g of catalyst and 690.675mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 90 ℃, excessive acetic acid is removed from reaction liquid by normal pressure distillation after the reaction is finished, and then glycerol triacetate is obtained by reduced pressure distillation.
The catalyst is EX146H and D72 with the mass ratio of 3:1, and the particle size of the EX146H catalyst is 1.0 mm; the particle size of the D72 catalyst is 1.2 mm;
the water-carrying agent is cyclohexane and n-propyl acetate with the volume ratio of 10: 1.
Example 4 preparation method of glyceryl triacetate
46.045g of glycerol (0.5mol), 115.1125g of acetic acid (2.5mol), 0.115g of catalyst and 690.675mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 10 hours at 95 ℃, after the reaction is finished, excessive acetic acid is removed from reaction liquid by normal pressure distillation, and then glycerol triacetate is obtained by reduced pressure distillation.
The catalyst is EX146H, and the particle size of the EX146H catalyst is 1.0 mm;
the water-carrying agent is cyclohexane.
Example 5 preparation method of glyceryl triacetate
46.045g of glycerol (0.5mol), 115.1125g of acetic acid (2.5mol), 0.115g of catalyst and 690.675mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 90 ℃, excessive acetic acid is removed from reaction liquid by normal pressure distillation after the reaction is finished, and then glycerol triacetate is obtained by reduced pressure distillation.
The catalyst is D72, and the particle size of the D72 catalyst is 1.2 mm;
the water carrying agent is n-propyl acetate.
Comparative example 1
The difference from example 3 is that: the mass ratio of EX146H to D72 was 1: 1, and the other operations and steps were the same as in example 3.
Comparative example 2
The difference from example 3 is that: the mass ratio of EX146H to D72 was 6: 1, and the other operations and steps were the same as in example 3.
Comparative example 3
The difference from example 3 is that: the particle sizes of EX146H and D72 were 1.0mm, and the other operations and steps were the same as in example 3.
Comparative example 4
The difference from example 3 is that: the water-carrying agent is a mixture of cyclohexane and n-propyl acetate with the volume ratio of 3:1, and other operations and steps are the same as those in the embodiment 3.
Comparative example 5
The difference from example 3 is that: the water-carrying agent is a mixture of cyclohexane and n-propyl acetate with the volume ratio of 12: 1, and other operations and steps are the same as those in the embodiment 3.
Test example 1 yield and purity of Glycerol triacetate product
The quantitative determination of glycerol triacetate was carried out by external standard method using gas chromatograph model Agilent 6890N. The chromatographic column is capillary Agilent19091N-113Hp-INNOWAX (30.00 mm × 0.32mm × 0.25 μm), and high purity H2High purity N used as fuel gas and compressed air for combustion supporting2As carrier gas, the temperature of the detector and the sample injector are both 280 ℃, the split ratio is 40: 1, the sample injection amount is 0.1 mu L, the initial temperature is 100 ℃, and the temperature is 30 ℃ per min-1The temperature is raised to 240 ℃ at the heating rate and kept for 2min, and the detection time is 12 min.
The yield and purity of the obtained glycerol triacetate product are shown in the following table 1.
The yield was ═ (actual yield ÷ theoretical yield) × 100%
Purity ═ purity (content of triacetin in product ÷ actual yield) × 100%
TABLE 1
According to the detection data in the above table 1, the yield and purity of the triacetin obtained by the preparation method of triacetin provided by the invention are both high, the catalyst is controlled to be a mixture of EX146H and D72 with a mass ratio of 2-5:1, the water-carrying agent is cyclohexane and n-propyl acetate with a volume ratio of 5-10:1, and the particle size of the catalyst is controlled to obviously improve the conversion rate of glycerol, so that the yield and purity of the finally obtained triacetin are both obviously improved, especially the particle size of EX146H and D72 is controlled to be 3:1, the particle size of EX146H is 1.0mm, and the particle size of D72 is 1.2mm in the embodiment 3; and the volume ratio of the cyclohexane to the n-propyl acetate is 10:1, the yield of the finally obtained glycerol triacetate is 98.3, the purity is 98.91, and the yield and the purity of the glycerol triacetate are obviously reduced by changing the type, the mass ratio or the particle size of the catalyst.
Test example 2 measurement of the content of Glycerol acetate and Glycerol diacetate
In order to further illustrate that the glycerol triacetate prepared by the method has higher purity, the content of by-products of glycerol monoacetate and glycerol diacetate obtained in the product is detected, and the result is shown in the following table 2.
TABLE 2
According to the detection data in the above table 2, the purity of the triacetin obtained by the preparation method of triacetin provided by the invention is higher, the catalyst is controlled to be a mixture of EX146H and D72 with a mass ratio of 2-5:1, the water-carrying agent is cyclohexane and n-propyl acetate with a volume ratio of 5-10:1, and the particle size of the catalyst is controlled to obviously improve the conversion rate of glycerol, so that the content of monoacetin and diacetin the obtained product is lower, particularly, the mass ratio of EX146H to D72 is controlled to be 3:1 in example 3, the particle size of EX146H is 1.0mm, and the particle size of D72 is 1.2 mm; and the volume ratio of the cyclohexane to the n-propyl acetate is 10:1, the content of the glycerol monoacetate and the glycerol diacetate in the finally obtained glycerol triacetate is the lowest, so the purity of the glycerol triacetate obtained in the embodiment 3 is the highest; when the type, the mass ratio or the particle size of the catalyst and the volume ratio of the components in the water-carrying agent are not in the claimed range, the content of the glycerol monoacetate and the content of the glycerol diacetate in the glycerol triacetate are obviously improved.
The present invention has been further described with reference to specific embodiments, which are only exemplary and do not limit the scope of the present invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (10)
1. A preparation method of glycerol triacetate uses glycerol and acetic acid as raw materials, and esterification reaction is carried out in the presence of a catalyst and a water-carrying agent to obtain glycerol triacetate; the method is characterized in that: the catalyst is cation exchange resin catalyst, and the cation exchange resin catalyst is selected from one or more of EX146H, D61, D72, Amberlyst-15, Nafion 511 and Amberlite IR-120.
2. The method of claim 1, wherein: the cation exchange resin catalyst is a mixture of EX146H and D72; the mass ratio of EX146H to D72 is 2-5: 1.
3. The method of claim 2, wherein: the mass ratio of EX146H to D72 is 3: 1.
4. The method of claim 1, wherein: the water-carrying agent is one or more of benzene, toluene, cyclohexane, n-propyl acetate, isopropyl acetate, chloroform and carbon tetrachloride.
5. The method of claim 4, wherein: the water-carrying agent is a mixture of cyclohexane and n-propyl acetate; the volume ratio of the cyclohexane to the n-propyl acetate is 5-10: 1.
6. The method of claim 5, wherein: the volume ratio of the cyclohexane to the n-propyl acetate is 10: 1.
7. The method of claim 1, wherein: the particle size of the catalyst is 0.8-1.20 mm.
8. The method of claim 7, wherein: the particle size of the EX146H catalyst is 0.8-1.0 mm; the particle size of the D72 catalyst is 1.0-1.2 mm.
9. The method of claim 8, wherein: the particle size of the EX146H catalyst is 1.0 mm; the particle size of the D72 catalyst was 1.2 mm.
10. The method of claim 1, wherein: the mass ratio of the catalyst to the glycerol is 0.15-0.35: 100, respectively; the mass ratio of the glycerol to the water-carrying agent is 100: 1.2-1.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110147281.3A CN112961056A (en) | 2021-02-03 | 2021-02-03 | Preparation method and application of glycerol triacetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110147281.3A CN112961056A (en) | 2021-02-03 | 2021-02-03 | Preparation method and application of glycerol triacetate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112961056A true CN112961056A (en) | 2021-06-15 |
Family
ID=76273715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110147281.3A Pending CN112961056A (en) | 2021-02-03 | 2021-02-03 | Preparation method and application of glycerol triacetate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112961056A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1213278B1 (en) * | 2000-11-30 | 2003-03-19 | La Chemial SpA | Process for esterification in a chromatographic reactor |
| CN108640835A (en) * | 2018-04-23 | 2018-10-12 | 南京工业大学 | A kind of method that organic catalysis prepares triacetyl glycerine |
| CN110078597A (en) * | 2019-03-13 | 2019-08-02 | 杭州盛弗泰新材料科技有限公司 | A kind of preparation method of glycerol 1,3- diethyl ether |
| CN111393295A (en) * | 2020-04-01 | 2020-07-10 | 江苏瑞佳新材料有限公司 | Preparation method of glycerol triacetate |
-
2021
- 2021-02-03 CN CN202110147281.3A patent/CN112961056A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1213278B1 (en) * | 2000-11-30 | 2003-03-19 | La Chemial SpA | Process for esterification in a chromatographic reactor |
| CN108640835A (en) * | 2018-04-23 | 2018-10-12 | 南京工业大学 | A kind of method that organic catalysis prepares triacetyl glycerine |
| CN110078597A (en) * | 2019-03-13 | 2019-08-02 | 杭州盛弗泰新材料科技有限公司 | A kind of preparation method of glycerol 1,3- diethyl ether |
| CN111393295A (en) * | 2020-04-01 | 2020-07-10 | 江苏瑞佳新材料有限公司 | Preparation method of glycerol triacetate |
Non-Patent Citations (5)
| Title |
|---|
| S. KALE EY AL.: "Selective formation of triacetin by glycerol acetylation using acidicion-exchange resins as catalyst and toluene as an entrainer", 《APPLIED CATALYSIS A：GENERAL》 * |
| 仓理主编: "《精细化工工艺 有机篇》", 31 May 1998, 化学工业出版社 * |
| 汪多仁主编: "《绿色增塑剂》", 31 October 2011, 科学技术文献出版社 * |
| 王树清: "强酸性阳离子交换树脂催化合成甘油三乙酸酯的研究", 《南通大学学报(自然科学版)》 * |
| 颜剑波等: "Amberlyst-15催化合成三醋酸甘油酯工艺条件研究", 《浙江科技学院学报》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20110160479A1 (en) | Process for the production of esters of levulinic acid from biomasses | |
| EP2097367A1 (en) | Process for preparing alkyl esters of fatty acids and acrolein from triglycerides | |
| CN106119303B (en) | Method for preparing chiral 3-cyclohexene-1-formic acid by protease resolution | |
| EP0326063B1 (en) | Process for the preparation of optically active cyanhydrins | |
| JPH09227488A (en) | Production of (s)-cyanohydrin | |
| EP1842843A1 (en) | Process for the synthesis of carboxylic acid alkyl esters | |
| CN1176094C (en) | Synthesis of trichlorosucrose | |
| CN106573852A (en) | Process for the manufacture of furfural and furfural derivatives | |
| Peris et al. | Supported Ionic Liquid‐Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins | |
| CN101348451B (en) | Preparation of medicinal D,L-2-hydroxy-4-methylthio calcium butyrate | |
| CN104119230B (en) | A kind of synthetic method of long-chain nipagin esters and application thereof | |
| CN1341091A (en) | Process for preparation of (2R)-2-propyloctanoic acid | |
| Higashio et al. | Continuous‐Flow Dynamic Kinetic Resolution of Racemic Alcohols by Lipase–Oxovanadium Cocatalysis | |
| CN112592356A (en) | Method for synthesizing lornoxicam | |
| CN112961056A (en) | Preparation method and application of glycerol triacetate | |
| CN113292522A (en) | Method for preparing 5-hydroxymethylfurfural by catalyzing biomass sugar with organic acid | |
| CN103998438A (en) | Method for manufacturing compounds including nitrile functions | |
| JPS6263543A (en) | Esterification | |
| CN110639511B (en) | Catalyst for carbon-carbon double bond hydrogenation of acrylate and application thereof | |
| CN101560527B (en) | Method for lipase-catalyzed synthesis of feruloylated acylglycerol in solvent-free system | |
| CN111944855B (en) | Method for synthesizing (R) -1- (4- (benzyloxy) -3-nitrophenyl) -2-bromoethanol | |
| CN104030984A (en) | Method for preparing pyrazole derivative | |
| CN114522720B (en) | Biomass-based carbon-silicon material immobilized heteropolyacid catalyst, and preparation and application thereof | |
| CN101293884A (en) | (1S,2S)-1-(2-furyl)-1,2-propylene glycol or its analogue, preparation and application thereof | |
| CN111499497A (en) | Preparation method of thymol |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210615 |