CN113289547A - Preparation method of dehydrated mannitol oleate emulsifier - Google Patents
Preparation method of dehydrated mannitol oleate emulsifier Download PDFInfo
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- CN113289547A CN113289547A CN202010522409.5A CN202010522409A CN113289547A CN 113289547 A CN113289547 A CN 113289547A CN 202010522409 A CN202010522409 A CN 202010522409A CN 113289547 A CN113289547 A CN 113289547A
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- reaction
- mannitol
- activated carbon
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- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 17
- 229940049964 oleate Drugs 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 dehydrated mannitol oleate Chemical class 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 34
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 28
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 24
- 229930195725 Mannitol Natural products 0.000 claims abstract description 24
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000594 mannitol Substances 0.000 claims abstract description 24
- 235000010355 mannitol Nutrition 0.000 claims abstract description 24
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 21
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 21
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000005642 Oleic acid Substances 0.000 claims abstract description 21
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000018044 dehydration Effects 0.000 claims abstract description 14
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 17
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000000746 purification Methods 0.000 abstract description 5
- 238000004904 shortening Methods 0.000 abstract description 4
- 238000005886 esterification reaction Methods 0.000 description 19
- 230000032050 esterification Effects 0.000 description 14
- 238000006266 etherification reaction Methods 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005580 one pot reaction Methods 0.000 description 5
- 238000004042 decolorization Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
The invention relates to a preparation method of a dehydrated mannitol oleate emulsifier, which comprises the following steps: s1, adding 200-500 g of mannitol into a reaction kettle, and heating to 166-220 ℃ to a molten state; s2, adding 500-700 g of oleic acid and 10-30 g of phosphoric acid, heating to 150-250 ℃ for reaction for 0.5-1.5 hours, S3, vacuumizing for dehydration for 1.5-2.5 hours, stopping reaction, and cooling to room temperature; s4, adding 4-6 liters of methanol, separating an upper layer, and concentrating the volume of the solvent to 0.5-1.5 liters; s5, adding 5-15 g of activated carbon, heating and refluxing for decoloring, filtering the activated carbon while the activated carbon is hot, and concentrating to obtain a finished product. The preparation method of the dehydration mannitol oleate emulsifier provided by the invention is beneficial to shortening the chemical reaction and the purification time of the product in the production process, saving the time and labor cost, and producing high-quality finished products.
Description
Technical Field
The invention relates to a preparation method of a dehydrated mannitol oleate emulsifier.
Background
At present, the commonly used preparation methods of the dehydrated mannitol oleate emulsifier are divided into two methods, the first method is a two-step method of dehydration, etherification and esterification, the preparation process is complicated in the production process, the chemical reaction and the purification time of the product are long, so that the time and labor cost are high, and more catalysts such as acid or alkali are mixed in the product.
In order to solve the defects of the first preparation method, the second preparation method is a one-pot dehydration esterification method in the prior art, although the production method is simplified in process, the esterification efficiency is low, the product reproducibility is poor, and the emulsifier product with stable quality and qualification is difficult to obtain.
Disclosure of Invention
Aiming at overcoming the defects of the prior art, the invention improves the one-pot dehydration esterification method, improves the preparation method of the dehydration mannitol oleate emulsifier on the basis of the one-pot dehydration esterification method, can be beneficial to shortening the chemical reaction and the purification time of products in the production process, saves the time and labor cost, and can produce high-quality finished products.
The technical problem in the prior art is solved.
The preparation method of the dehydrated mannitol oleate emulsifier is characterized by comprising the following steps:
s1, adding 200-500 g of mannitol into a reaction kettle, and heating to 166-220 ℃ to a molten state;
s2, adding 500-700 g of oleic acid and 10-30 g of phosphoric acid, heating to 150-250 ℃ for reaction for 0.5-1.5 hours,
s3, stopping the reaction after the vacuum pumping dehydration reaches 1.5-2.5 hours, and cooling to room temperature;
s4, adding 4-6 liters of methanol, separating an upper layer, and concentrating the volume of the solvent to 0.5-1.5 liters;
s5, adding 5-15 g of activated carbon, heating and refluxing for decoloring, filtering the activated carbon while the activated carbon is hot, and concentrating to obtain a finished product.
In step S1, the mannitol is added to the reaction kettle to melt, which is beneficial to uniform mixing with the subsequently added oleic acid and phosphoric acid catalyst and thorough esterification.
In step S2, phosphoric acid is used as a catalyst for mannitol etherification and oleic acid esterification. Oleic acid needs to be added slowly at a constant speed to prevent molten mannitol from contacting with cold oleic acid to rapidly agglomerate and cause uneven reaction. Firstly, the reaction is carried out for 0.5 to 1.5 hours under normal pressure, so that the phenomenon that the initial reaction is too violent and a large amount of black carbonized solid impurities are generated can be avoided.
In the step S3, water generated in the process of mannitol etherification and oleic acid esterification can be rapidly removed by vacuumizing, forward proceeding of etherification and esterification reactions is facilitated, and no obvious water is generated after vacuumizing for about 1.5-2.5 hours, which indicates complete reaction.
In step S4, methanol is added in order to dissolve most of the product while removing methanol-insoluble impurities and solid impurities generated during the reaction.
In step S5, the concentrated methanol solution of step S4 is brown, and the active carbon is added to remove the color of the product, and the product is light yellow after decolorization by active carbon.
Preferably, the mannitol added into the reaction kettle in the step S1 is 300-400 g, and is heated to 170-200 ℃ to be in a molten state.
Preferably, in the step S2, the oleic acid is added in an amount of 550 to 650 g, the phosphoric acid is added in an amount of 15 to 25 g, and the temperature is raised to 180 to 240 ℃ to react for 1 hour.
Preferably, in step S3, the reaction is stopped after vacuum dehydration for 2 hours, and the temperature is reduced to room temperature below 25 ℃.
Preferably, in the step S4, the amount of the methanol added is 4.5-5.5 liters, the upper layer is separated and the volume of the solvent is concentrated to 0.8-1.2 liters.
Preferably, in the step S5, the amount of the activated carbon added is 8-13 g.
The invention has the beneficial effects that:
in the step S1, the mannitol is added into the reaction kettle for melting, so that the mannitol is favorably and uniformly mixed with subsequently added oleic acid and phosphoric acid catalysts, and the esterification reaction is favorably and completely carried out; in step S2, phosphoric acid is used as a catalyst for mannitol etherification and oleic acid esterification. Oleic acid needs to be slowly added at a constant speed, so that molten mannitol is prevented from being rapidly agglomerated when contacting with cold oleic acid, the reaction is not uniform, the reaction is firstly carried out for 0.5-1.5 hours at normal pressure, and the over-violent initial reaction and the generation of a large amount of black carbonized solid impurities can be avoided; in the step S3, water generated in the process of mannitol etherification and oleic acid esterification can be rapidly removed by vacuumizing, forward proceeding of etherification and esterification reactions is facilitated, no obvious water is further produced after vacuumizing for about 1.5-2.5 hours, and the reaction is marked to be complete; in step S4, methanol is added in order to dissolve most of the product and remove methanol-insoluble impurities and solid impurities generated during the reaction; in step S5, the concentrated methanol solution of step S4 is brown, and the active carbon is added to remove the color of the product, and the product is light yellow after decolorization by active carbon. The preparation method of the dehydration mannitol oleate emulsifier provided by the invention is beneficial to shortening the chemical reaction and the purification time of the product in the production process, saving the time and labor cost, and producing high-quality finished products.
Detailed Description
In the following description of the present invention, in conjunction with the detailed description, if the terms "first", "second", etc. are used for descriptive purposes only and are not to be construed as indicating or implying any relative importance, it will be apparent to those of ordinary skill in the art that the specific meanings of the terms described above can be understood according to specific situations.
The preparation method of the dehydrated mannitol oleate emulsifier is characterized by comprising the following steps:
s1, adding 300-400 g of mannitol into a reaction kettle, and heating to 170-200 ℃ to a molten state;
s2, adding 550-650 g of oleic acid and 15-25 g of phosphoric acid, and heating to 180-240 ℃ for reaction for 0.5-1.5 hours;
s3, vacuumizing and dehydrating for 2 hours, stopping the reaction, and cooling to room temperature below 25 ℃;
s4, adding 4.5-5.5 liters of methanol, separating an upper layer, and concentrating the volume of the solvent to 0.8-1.2 liters;
s5, adding 8-13 g of activated carbon, heating and refluxing for decoloring, filtering the activated carbon while the activated carbon is hot, and concentrating to obtain a finished product.
In the step S1, the mannitol is added into the reaction kettle for melting, so that the mannitol is favorably and uniformly mixed with subsequently added oleic acid and phosphoric acid catalysts, and the esterification reaction is favorably and completely carried out; in step S2, phosphoric acid is used as a catalyst for mannitol etherification and oleic acid esterification. Oleic acid needs to be slowly added at a constant speed, so that molten mannitol is prevented from being rapidly agglomerated when contacting with cold oleic acid, the reaction is not uniform, the reaction is firstly carried out for 0.5-1.5 hours at normal pressure, and the over-violent initial reaction and the generation of a large amount of black carbonized solid impurities can be avoided; in the step S3, water generated in the process of mannitol etherification and oleic acid esterification can be quickly removed by vacuumizing, forward proceeding of etherification and esterification reactions is facilitated, and after vacuumizing for about 2 hours, no obvious water is further produced, which indicates complete reaction; in step S4, methanol is added in order to dissolve most of the product and remove methanol-insoluble impurities and solid impurities generated during the reaction; in step S5, the concentrated methanol solution of step S4 is brown, and the active carbon is added to remove the color of the product, and the product is light yellow after decolorization by active carbon.
The invention improves the one-pot dehydration esterification method in the prior art, improves the preparation method of the dehydration mannitol oleate emulsifier on the basis of the one-pot dehydration esterification method, can be beneficial to shortening the chemical reaction and the purification time of products in the production process, saves the time and labor cost, and can produce high-quality finished products.
It should be understood that the above-described embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (6)
1. The preparation method of the dehydrated mannitol oleate emulsifier is characterized by comprising the following steps:
s1, adding 200-500 g of mannitol into a reaction kettle, and heating to 166-220 ℃ to a molten state;
s2, adding 500-700 g of oleic acid and 10-30 g of phosphoric acid, and heating to 150-250 ℃ for reaction for 0.5-1.5 hours;
s3, vacuumizing and dehydrating for 1.5-2.5 hours, stopping the reaction, and cooling to room temperature;
s4, adding 4-6 liters of methanol, separating an upper layer, and concentrating the volume of the solvent to 0.5-1.5 liters;
s5, adding 5-15 g of activated carbon, heating and refluxing for decoloring, filtering the activated carbon while the activated carbon is hot, and concentrating to obtain a finished product.
2. The method for preparing the emulsifier of anhydromannitol oleate according to claim 1, wherein 300-400 g of mannitol is added into the reaction kettle in step S1, and the mixture is heated to 170-200 ℃ to a molten state.
3. The method for preparing the hydromannitol oleate emulsifier according to claim 1, wherein in the step S2, the oleic acid is added in an amount of 550-650 g, the phosphoric acid is added in an amount of 15-25 g, and the temperature is raised to 180-240 ℃ for reaction for 0.5-1.5 hours.
4. The method for preparing the anhydromannitol oleate emulsifier of claim 1, wherein in step S3, the reaction is stopped after vacuum dehydration for 2 hours, and the temperature is reduced to room temperature below 25 ℃.
5. The method of claim 1, wherein the amount of methanol added in step S4 is 4.5-5.5L, the upper layer is separated and the volume of the solvent is concentrated to 0.8-1.2L.
6. The method for preparing the emulsifier according to claim 1, wherein the amount of the activated carbon added in step S5 is 8-13 g.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010522409.5A CN113289547A (en) | 2020-06-10 | 2020-06-10 | Preparation method of dehydrated mannitol oleate emulsifier |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010522409.5A CN113289547A (en) | 2020-06-10 | 2020-06-10 | Preparation method of dehydrated mannitol oleate emulsifier |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85100482A (en) * | 1984-12-05 | 1987-01-24 | 澳大利亚吹制油有限公司 | Emulsion |
| US6156807A (en) * | 1997-09-24 | 2000-12-05 | Mitsubishi Chemical Corporation | Powdered emulsifier composition and process for producing the same |
| CN103059073A (en) * | 2012-12-14 | 2013-04-24 | 江苏省海安石油化工厂 | Method for preparing water-loss mannitol oleate |
| CN103087015A (en) * | 2012-12-19 | 2013-05-08 | 湖北葛店人福药用辅料有限责任公司 | Preparation method of sorbitan oleate servicing as medicinal auxiliary material |
-
2020
- 2020-06-10 CN CN202010522409.5A patent/CN113289547A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85100482A (en) * | 1984-12-05 | 1987-01-24 | 澳大利亚吹制油有限公司 | Emulsion |
| US6156807A (en) * | 1997-09-24 | 2000-12-05 | Mitsubishi Chemical Corporation | Powdered emulsifier composition and process for producing the same |
| CN103059073A (en) * | 2012-12-14 | 2013-04-24 | 江苏省海安石油化工厂 | Method for preparing water-loss mannitol oleate |
| CN103087015A (en) * | 2012-12-19 | 2013-05-08 | 湖北葛店人福药用辅料有限责任公司 | Preparation method of sorbitan oleate servicing as medicinal auxiliary material |
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Application publication date: 20210824 |