CN112375107A - Preparation method of sucrose ester - Google Patents
Preparation method of sucrose ester Download PDFInfo
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- CN112375107A CN112375107A CN202011184469.7A CN202011184469A CN112375107A CN 112375107 A CN112375107 A CN 112375107A CN 202011184469 A CN202011184469 A CN 202011184469A CN 112375107 A CN112375107 A CN 112375107A
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- sucrose
- palm oil
- hydrogenated palm
- ester
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
Abstract
The invention discloses a preparation method of sucrose ester, which comprises the following steps: preheating hydrogenated oil to 80 ℃ to completely dissolve the hydrogenated oil; taking caustic soda flakes with the mole mass fraction of 1.0-5.0% of hydrogenated oil into a round-bottom flask, reacting for 40 min at 80 ℃, and standing and dehydrating for 1 h; putting sucrose into a grinder, adding 200 mL of grinding zirconium beads into the sucrose, and grinding the mixture at room temperature at 1200 rpm for 10-90 min; taking potassium carbonate with the mole mass fraction of 1.0-5.0% of hydrogenated oil and activated sucrose with the mole mass fraction of 0.5-2.0%, stirring and heating to 120-150 ℃ at 100 rpm, reacting for 60-180 min with the vacuum degree of more than 0.09MPa, and determining the HLB value of the material to be within the range of 8.2-9.2 after the reaction is finished; drawing the wire at high temperature to obtain a reaction end point; standing for layering, wherein the upper layer is refined sucrose ester, and the lower layer is crude sucrose ester; taking hydrogen peroxide with the mass fraction of hydrogenated oil being 15%, and the mass fraction of the hydrogen peroxide being 30%, and reacting for 30 min at 80 ℃ to decolor the sucrose ester at the upper layer. The application adopts a solvent-free method, and does not pollute products.
Description
Technical Field
The invention belongs to the technical field of sucrose ester preparation, and particularly relates to a preparation method of sucrose ester.
Background
Sucrose fatty acid ester (sucrose ester) is a sucrose ester for short, has the advantages of wide HLB value, excellent emulsifying property, no toxicity, biodegradability and the like, and is widely used in the industries of food, medicine, cosmetics and the like.
With the increasing consumption of fossil resources and the expansion and increase of the consumption of Surfactants, there is a need to develop bio-based Surfactants that meet the new energy and environmental requirements to replace or partially replace petroleum-based Surfactants (Journal of Surfactants and Detergents, 2019, 22 (1): 32-37). The sucrose fatty acid ester belongs to a polyol nonionic surfactant, can be absorbed by human bodies due to easy biodegradation, is harmless to the human bodies, does not irritate the skin and mucous membranes, has good surface chemical properties, and is a nonionic surfactant with development prospect.
At present, the industrial production method of sucrose fatty acid ester adopts an ester exchange method, and the synthesis of sucrose ester by the ester exchange method is divided into a solvent method and a solvent-free method. The solvent-free method has simple production process, short production period, no solvent recovery problem, low cost and high yield, and meets the requirements on the direction of nontoxic low-cost green chemical synthesis (food science, 2005, (07): 128-132).
In the solvent-free synthesis process, the addition of the fluxing agent can effectively promote the sucrose to be in a molten state under a low-temperature condition, so that the contact between a reaction substrate and a catalyst is improved, the reaction rate is improved, and the coking reaction of the sucrose is inhibited. Hupeng et al studied the transesterification of sucrose with methyl fatty acid ester under solvent-free conditions using potassium carbonate as a catalyst, and investigated the effect of sodium stearate, potassium oleate, monoglyceride or sucrose ester as a flux on the transesterification rate, and found that the addition of flux enables sucrose and methyl stearate to form a good homogeneous molten phase at 135 ℃, the fluxing effect of potassium stearate is the best, and the yield of sucrose fatty acid ester can reach 68.5% (China Oils and Fats, 1999, 24 (5): 61-64).
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a preparation method of sucrose ester without solvent.
The technical scheme for solving the technical problems is as follows:
a preparation method of sucrose ester comprises the following steps:
(1) taking hydrogenated palm oil in a round-bottom flask, and preheating to 80 ℃ to completely dissolve the hydrogenated palm oil;
(2) placing flake caustic soda with the molar mass fraction of 1.0-5.0% of hydrogenated palm oil into a round-bottom flask, reacting for 40 min at 80 ℃, and standing for dehydration;
(3) putting sucrose into a grinder, adding grinding zirconium beads, and grinding at the room temperature and the rotation speed of 1200 rpm for 10-90 min;
(4) according to the technical scheme, potassium carbonate with the mole mass fraction of 1.0-5.0% of hydrogenated palm oil and activated sucrose with the mole mass fraction of 0.5-2.0% of hydrogenated palm oil are taken and put in a round bottom flask, stirring is carried out at the rotating speed of 100 rpm, the temperature is increased to 120-150 ℃, the constant temperature reaction is carried out for 60-180 min under the condition that the vacuum degree is more than 0.09MPa, the reaction is finished, and the HLB value of the material is measured to be within the range of 8.2-9.2; drawing the material at high temperature, namely judging as a reaction end point;
(5) standing until materials are layered, wherein the upper layer is refined sucrose fatty acid ester which is completely reacted, the part of sucrose fatty acid ester is decolorized, and the lower layer is crude sucrose ester;
(6) hydrogen peroxide in an amount of 15% by mass based on the hydrogenated palm oil and 30% by mass based on the hydrogenated palm oil, and decolorizing at 80 deg.C for 30 min to refine sucrose fatty acid ester.
Preferably, in the above-mentioned method for producing a sucrose ester: the mass of the flake caustic soda in the step (2) is 3.0 percent of the molar mass of the hydrogenated palm oil.
Preferably, in the above-mentioned method for producing a sucrose ester: and (4) grinding time in the grinding in the step (3) is 60 min.
Preferably, in the above-mentioned method for producing a sucrose ester: the mass of potassium carbonate in the step (4) is 2.0 percent of the molar mass of the hydrogenated palm oil.
Preferably, in the above-mentioned method for producing a sucrose ester: the mass of the activated sucrose in the step (4) is 0.8 percent of the molar mass of the hydrogenated palm oil.
Preferably, in the above-mentioned method for producing a sucrose ester: the temperature in step (4) was 135 ℃.
Preferably, in the above-mentioned method for producing a sucrose ester: the constant temperature reaction time in the step (4) is 120 min.
Compared with the prior art, the invention has the following beneficial effects:
1. the preparation method disclosed by the invention has the advantages that no solvent is needed, the problems of large environmental risk and series of problems caused by toxic solvent residues in the application of the nitrogen-containing organic solvent are thoroughly solved, the refining process of the product is simplified, the reaction time is shortened, the yield is improved, and the cost of the subsequent purification process of the sucrose ester is greatly reduced; the used raw materials have wide sources, and industrial production is facilitated;
2. the invention adopts mechanical activation energy to effectively improve hydrogen bond energy and free hydroxyl content, converts partial mechanical energy into chemical energy to be stored, and obviously improves the activity of the solvent-free esterification reaction; the mechanical activation can also reduce the grain diameter of the materials through the action of external force, increase the contact area among the materials, increase the active centers which can participate in the reaction, thereby increasing the reaction rate;
3. the crude sucrose ester prepared by the method can be used as a raw material of a compound defoaming agent, and the raw material can be repeatedly utilized.
Detailed Description
The present invention will be further described with reference to the following examples, but it should be noted that the scope of the present invention is not limited to these examples.
Example 1:
(1) taking hydrogenated palm oil in a round-bottom flask, and preheating to 80 ℃ to completely dissolve the hydrogenated palm oil;
(2) placing flake caustic soda with a molar mass fraction of 1.0% of hydrogenated palm oil in a round-bottom flask, reacting at 80 ℃ for 40 min, and standing and dehydrating for 1 h;
(3) placing sucrose in a grinder, adding 200 mL of grinding zirconium beads in bulk volume, and grinding at 1200 rpm at room temperature for 10 min;
(4) according to the technical scheme, potassium carbonate with the mole mass fraction of 5.0% of hydrogenated palm oil and activated sucrose with the mole mass fraction of 2.0% of hydrogenated palm oil are taken and put in a round-bottom flask, the potassium carbonate and the activated sucrose are stirred at the rotating speed of 100 rpm, the temperature is raised to 120 ℃, the constant temperature reaction is carried out for 60 min under the condition that the vacuum degree is more than 0.09MPa, the reaction is finished, and the HLB value of the material is measured to be within the range of 8.2-9.2; drawing the material at high temperature to judge the reaction end point;
(5) standing until materials are layered, wherein the upper layer is refined sucrose fatty acid ester which is completely reacted, the part of sucrose fatty acid ester is decolorized, and the lower layer is crude sucrose ester;
(6) hydrogen peroxide in an amount of 15% by mass based on the hydrogenated palm oil and 30% by mass based on the hydrogenated palm oil, and decolorizing at 80 deg.C for 30 min to refine sucrose fatty acid ester.
Example 2:
(1) taking hydrogenated palm oil in a round-bottom flask, and preheating to 80 ℃ to completely dissolve the hydrogenated palm oil;
(2) placing flake caustic soda with the mole mass fraction of 3.0% of hydrogenated palm oil in a round-bottom flask, reacting for 40 min at 80 ℃, standing and dehydrating for 1 h;
(3) placing sucrose in a grinder, adding 200 mL of grinding zirconium beads in bulk volume, and grinding at 1200 rpm at room temperature for 60 min;
(4) according to the technical scheme, potassium carbonate with the mole mass fraction of 2.0% of hydrogenated palm oil and activated sucrose with the mole mass fraction of 0.8% of hydrogenated palm oil are taken and put in a round-bottom flask, the potassium carbonate and the activated sucrose are stirred at the rotating speed of 100 rpm, the temperature is raised to 135 ℃, the constant temperature reaction is carried out for 120 min under the condition that the vacuum degree is more than 0.09MPa, the reaction is finished, and the HLB value of the material is measured to be within the range of 8.2-9.2; drawing the material at high temperature to judge the reaction end point;
(5) standing until materials are layered, wherein the upper layer is refined sucrose fatty acid ester which is completely reacted, the part of sucrose fatty acid ester is decolorized, and the lower layer is crude sucrose ester;
(6) hydrogen peroxide in an amount of 15% by mass based on the hydrogenated palm oil and 30% by mass based on the hydrogenated palm oil, and decolorizing at 80 deg.C for 30 min to refine sucrose fatty acid ester.
Example 3:
(1) taking hydrogenated palm oil in a round-bottom flask, and preheating to 80 ℃ to completely dissolve the hydrogenated palm oil;
(2) putting flake caustic soda with the molar mass fraction of 4.0% of hydrogenated palm oil into a round-bottom flask, reacting for 90 min at 80 ℃, standing and dehydrating for 1 h;
(3) putting sucrose into a grinder, adding 200 mL of grinding zirconium beads with a bulk volume, and grinding at 1200 rpm for 10-90 min at room temperature;
(4) according to the technical scheme, potassium carbonate with the mole mass fraction of 3.0% of hydrogenated palm oil and activated sucrose with the mole mass fraction of 0.5% of hydrogenated palm oil are taken and put in a round-bottom flask, the potassium carbonate and the activated sucrose are stirred at the rotating speed of 100 rpm, the temperature is raised to 150 ℃, the constant temperature reaction is carried out for 90 min under the condition that the vacuum degree is more than 0.09MPa, the reaction is finished, and the HLB value of the material is measured to be within the range of 8.2-9.2; drawing the material at high temperature to judge the reaction end point;
(5) standing until materials are layered, wherein the upper layer is refined sucrose fatty acid ester which is completely reacted, the part of sucrose fatty acid ester is decolorized, and the lower layer is crude sucrose ester;
(6) hydrogen peroxide in an amount of 15% by mass based on the hydrogenated palm oil and 30% by mass based on the hydrogenated palm oil, and decolorizing at 80 deg.C for 30 min to refine sucrose fatty acid ester.
Example 4:
(1) taking hydrogenated palm oil in a round-bottom flask, and preheating to 80 ℃ to completely dissolve the hydrogenated palm oil;
(2) placing flake caustic soda with the molar mass fraction of 5.0% of hydrogenated palm oil in a round-bottom flask, reacting for 40 min at 80 ℃, standing and dehydrating for 1 h;
(3) placing sucrose in a grinder, adding 200 mL of grinding zirconium beads in bulk volume, and grinding at 1200 rpm at room temperature for 30 min;
(4) according to the method, potassium carbonate with the mole mass fraction of 1.0% of hydrogenated palm oil and activated sucrose with the mole mass fraction of 1.0% of hydrogenated palm oil are taken and put in a round bottom flask, the potassium carbonate and the activated sucrose are stirred at the rotating speed of 100 rpm, the temperature is raised to 140 ℃, the constant temperature reaction is carried out for 180 min under the condition that the vacuum degree is more than 0.09MPa, the reaction is finished, and the HLB value of the material is measured to be within the range of 8.2-9.2; drawing the material at high temperature to judge the reaction end point;
(5) standing until materials are layered, wherein the upper layer is refined sucrose fatty acid ester which is completely reacted, the part of sucrose fatty acid ester is decolorized, and the lower layer is crude sucrose ester;
(6) hydrogen peroxide in an amount of 15% by mass based on the hydrogenated palm oil and 30% by mass based on the hydrogenated palm oil, and decolorizing at 80 deg.C for 30 min to refine sucrose fatty acid ester.
Claims (7)
1. A preparation method of sucrose ester is characterized by comprising the following steps: the method comprises the following steps:
(1) taking hydrogenated palm oil in a round-bottom flask, and preheating to 80 ℃ to completely dissolve the hydrogenated palm oil;
(2) placing flake caustic soda with the molar mass fraction of 1.0-5.0% of hydrogenated palm oil into a round-bottom flask, reacting for 40 min at 80 ℃, and standing for dehydration;
(3) putting sucrose into a grinder, adding grinding zirconium beads, and grinding at the room temperature and the rotation speed of 1200 rpm for 10-90 min;
(4) according to the technical scheme, potassium carbonate with the mole mass fraction of 1.0-5.0% of hydrogenated palm oil and activated sucrose with the mole mass fraction of 0.5-2.0% of hydrogenated palm oil are taken and put in a round bottom flask, stirring is carried out at the rotating speed of 100 rpm, the temperature is increased to 120-150 ℃, the constant temperature reaction is carried out for 60-180 min under the condition that the vacuum degree is more than 0.09MPa, the reaction is finished, and the HLB value of the material is measured to be within the range of 8.2-9.2; drawing the material at high temperature, namely judging as a reaction end point;
(5) standing until materials are layered, wherein the upper layer is refined sucrose fatty acid ester which is completely reacted, the part of sucrose fatty acid ester is decolorized, and the lower layer is crude sucrose ester;
(6) hydrogen peroxide in an amount of 15% by mass based on the hydrogenated palm oil and 30% by mass based on the hydrogenated palm oil, and decolorizing at 80 deg.C for 30 min to refine sucrose fatty acid ester.
2. The process for the preparation of sucrose ester as in claim 1, wherein: the mass of the flake caustic soda in the step (2) is 3.0 percent of the molar mass of the hydrogenated palm oil.
3. The process for the preparation of sucrose ester as in claim 1, wherein: and (4) grinding time in the grinding in the step (3) is 60 min.
4. The process for the preparation of sucrose ester as in claim 1, wherein: the mass of potassium carbonate in the step (4) is 2.0 percent of the molar mass of the hydrogenated palm oil.
5. The process for the preparation of sucrose ester as in claim 1, wherein: the mass of the activated sucrose in the step (4) is 0.8 percent of the molar mass of the hydrogenated palm oil.
6. The process for the preparation of sucrose ester as in claim 1, wherein: the temperature in step (4) was 135 ℃.
7. The process for the preparation of sucrose ester as in claim 1, wherein: the constant temperature reaction time in the step (4) is 120 min.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996206A (en) * | 1973-03-16 | 1976-12-07 | Tate & Lyle Limited | Process of making sucrose esters |
| US5527903A (en) * | 1991-06-14 | 1996-06-18 | Mitsubishi Kasei Corporation | Process for preparing sucrose fatty acid esters |
| WO2006054708A1 (en) * | 2004-11-19 | 2006-05-26 | Mitsubishi Chemical Corporation | Sucrose fatty acid ester with low degree of substitution and process for producing the same |
| JP2016141668A (en) * | 2015-02-04 | 2016-08-08 | 第一工業製薬株式会社 | Method for producing sucrose fatty acid ester |
| CN108003203A (en) * | 2017-11-28 | 2018-05-08 | 广东省石油与精细化工研究院 | A kind of preparation method of saccharide fatty acid esters |
| CN111094312A (en) * | 2019-12-13 | 2020-05-01 | 广州嘉德乐生化科技有限公司 | Preparation method of sucrose ester |
-
2020
- 2020-10-30 CN CN202011184469.7A patent/CN112375107A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996206A (en) * | 1973-03-16 | 1976-12-07 | Tate & Lyle Limited | Process of making sucrose esters |
| US5527903A (en) * | 1991-06-14 | 1996-06-18 | Mitsubishi Kasei Corporation | Process for preparing sucrose fatty acid esters |
| WO2006054708A1 (en) * | 2004-11-19 | 2006-05-26 | Mitsubishi Chemical Corporation | Sucrose fatty acid ester with low degree of substitution and process for producing the same |
| CN101056882A (en) * | 2004-11-19 | 2007-10-17 | 三菱化学株式会社 | Sucrose fatty acid ester having low degree of substitution and method for producing the same |
| JP2016141668A (en) * | 2015-02-04 | 2016-08-08 | 第一工業製薬株式会社 | Method for producing sucrose fatty acid ester |
| CN108003203A (en) * | 2017-11-28 | 2018-05-08 | 广东省石油与精细化工研究院 | A kind of preparation method of saccharide fatty acid esters |
| CN111094312A (en) * | 2019-12-13 | 2020-05-01 | 广州嘉德乐生化科技有限公司 | Preparation method of sucrose ester |
Non-Patent Citations (1)
| Title |
|---|
| 王奎;蒋剑春;李翔宇;吴欢;李科;: "生物柴油用于合成蔗糖酯的工艺研究", 林产化学与工业 * |
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