CN113893842B - Preparation method of modified supported magnesium oxide catalyst and monoglyceride production process - Google Patents
Preparation method of modified supported magnesium oxide catalyst and monoglyceride production process Download PDFInfo
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- CN113893842B CN113893842B CN202111119916.5A CN202111119916A CN113893842B CN 113893842 B CN113893842 B CN 113893842B CN 202111119916 A CN202111119916 A CN 202111119916A CN 113893842 B CN113893842 B CN 113893842B
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
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- 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
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Abstract
The preparation method of the modified supported magnesium oxide catalyst and the production process of the monoglyceride comprise the following steps: soaking the carrier with deionized water, adding a magnesium nitrate aqueous solution while stirring, and regulating the pH value of the solution with a sodium hydroxide solution to generate a magnesium hydroxide precipitate; soaking and filtering to obtain a filter cake, and cleaning, drying and roasting the filter cake to obtain magnesium oxide; and (3) impregnating the obtained magnesium oxide with cerium salt or lanthanum salt, and cleaning, drying and roasting after the impregnation is finished to obtain the modified magnesium oxide catalyst. Adding a modified supported magnesium oxide catalyst into a fixed bed reactor, introducing preheated and melted hydrogenated grease and glycerol into the fixed bed reactor for reaction, raising the temperature, and introducing nitrogen; after the reaction is finished, the reaction liquid is collected and separated to obtain the monoglyceride. The invention adopts the supported magnesium oxide catalyst, cerium salt or lanthanum salt is added for modification, the selectivity of monoglyceride is improved to 60 percent from 40 percent in the prior art, the reaction temperature is reduced, and the energy consumption is saved.
Description
Technical Field
The invention belongs to the field of monoglyceride preparation, and in particular relates to a preparation method of a modified supported magnesium oxide catalyst and a monoglyceride production process.
Background
The magnesia material is widely applied to the fields of catalysts, refractory materials, rubber activators, accelerators, functional ceramics and the like. Among them, magnesium oxide has the characteristics of low price, large specific surface area, no toxicity and no harm, and plays an important role in the catalysis field. However, the existing magnesium oxide catalyst often has the problems of insufficient active site, insufficient alkalinity, complex preparation process, low catalytic performance and the like, and has the problem of insufficient catalytic activity in some reactions (such as monoglyceride preparation).
Monoglyceride (monoglyceride) is used as an important food emulsifier and additive, and has been widely used in plastics, foods, pharmaceuticals, cosmetics, etc.
The prior industry adopts the steps that glycerol, hydrogenated oil and alkali liquor are dehydrated according to the proportion specified by the process, then enter an esterification reaction, the esterification reaction is cooled and then is neutralized with phosphoric acid, and the crude ester is obtained after standing and discharging the bottom glycerol. The monoglyceride product is obtained by molecular distillation of the crude ester.
However, the reaction monoglyceride has low selectivity, and the subsequent use of sodium hydroxide as a catalyst requires the neutralization with phosphoric acid, and soap substances such as sodium stearate and the like are easy to form in the post-treatment process, so that foam is easy to form, and the distillation effect is affected.
Disclosure of Invention
Based on the defects and shortcomings in the prior art, the invention provides a preparation method of a modified supported magnesium oxide catalyst and a monoglyceride production process, wherein the magnesium oxide is modified to increase the catalytic performance of the magnesium oxide, and the modified supported magnesium oxide is used as a solid catalyst to replace sodium hydroxide, so that the monoglyceride selectivity is improved, and the occurrence of post-treated foam is avoided.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the preparation method of the modified supported magnesium oxide catalyst comprises the following steps:
s1, soaking a carrier in deionized water, adding a magnesium nitrate aqueous solution while stirring, and adjusting the pH value of the solution by using a sodium hydroxide aqueous solution to generate a magnesium hydroxide precipitate; soaking and filtering to obtain a filter cake, and cleaning, drying and roasting the filter cake to obtain magnesium oxide;
s2, impregnating the obtained magnesia with cerium salt or lanthanum salt, and cleaning, drying and roasting after the impregnation is finished to obtain the modified magnesia catalyst.
Preferably, the carrier is gamma-Al 2 O 3 、SiO 2 ZSM-5 molecular sieve, activated carbon or diatomaceous earth.
Preferably, the mass fraction of the magnesium nitrate aqueous solution is 16-23%, and the mass of the added magnesium nitrate aqueous solution is 10-25% of the mass of the carrier.
Preferably, the cerium salt or lanthanum salt is nitrate solution with the mass fraction of 15-25%, and the addition amount of the nitrate solution is 5-25% of the mass of the carrier.
Preferably, the mass fraction of the sodium hydroxide aqueous solution is 5-15%, and the pH of the solution is adjusted to 8-9.
Preferably, in both S1 and S2, the impregnation time is not less than 10 hours, the drying temperature is more than 110 ℃, the drying time is 4-6 hours, the roasting temperature is more than 550 ℃, and the roasting time is 4-6 hours.
The invention also provides a production process of the monoglyceride, which comprises the following steps:
s11, adding the modified supported magnesium oxide catalyst into a fixed bed reactor,
s12, introducing preheated and melted hydrogenated grease and glycerin into a fixed bed reactor for reaction, raising the temperature, introducing nitrogen, and keeping the flow rate of the nitrogen at 30-100ml/min;
s13, collecting a reaction liquid after the reaction is finished, and separating to obtain the monoglyceride.
Preferably, the reaction temperature in step S2 is 190-210 ℃.
Preferably, the reaction time in step S2 is 50 to 130 minutes.
Preferably, the separation method of step S3 is a molecular distillation method.
Preferably, the raw materials are added in the following amounts in parts by weight: 0.3-0.7 part of modified supported magnesium oxide catalyst, 80-95 parts of hydrogenated grease and 15-20 parts of glycerol.
Compared with the prior art, the invention has the beneficial effects that:
the invention adopts the supported magnesium oxide catalyst, and cerium salt or lanthanum salt is added for modification, so that the alkalinity of the magnesium oxide reaction active site is enhanced, the selectivity of monoglyceride is improved to 60% from 40% in the prior art, the reaction temperature is reduced, and the energy consumption is saved.
The invention adopts the supported magnesium oxide catalyst to replace sodium hydroxide, does not need phosphoric acid for neutralization in post-treatment, avoids the generation of soap substances in the distillation process, reduces the generation of foam, and improves the distillation effect.
The invention adopts a fixed bed reaction device to replace the traditional kettle type reaction, thereby realizing the continuous production of the monoglyceride.
Detailed Description
In order to more clearly illustrate the embodiments of the present invention, specific embodiments of the present invention will be described below. It will be apparent to those of ordinary skill in the art that the following descriptions are only illustrative of the invention and that other embodiments are possible without undue burden to those of ordinary skill in the art.
Example 1:
taking 100g of gamma-Al 2 O 3 The carrier (also SiO) 2 ZSM-5, activated carbon or diatomite), adding a proper amount of deionized water (the proper amount of all the infiltration carriers is adopted), adding 14g of a magnesium nitrate aqueous solution with the mass fraction of 16% while stirring, and adjusting the pH to 8-9 by using a 10% sodium hydroxide aqueous solution to produce magnesium hydroxide precipitate. And immersing the magnesium hydroxide precipitate for 11 hours, filtering to obtain a filter cake, cleaning the filter cake, drying at 110 ℃ for 5 hours, and roasting at 550 ℃ for 5 hours to obtain magnesium oxide.
The obtained magnesia is immersed in cerium nitrate solution with 15 percent of carrier mass for 12 hours, and dried at 110 ℃ for 5 hours and baked at 550 ℃ for 5 hours to obtain the modified supported magnesia catalyst.
Example 2:
taking 100g of gamma-Al 2 O 3 The carrier (also SiO) 2 ZSM-5, activated carbon or diatomaceous earth) and adding deionized water (to fully infiltrate the carrier)The volume is proper), 16g of 20% magnesium nitrate aqueous solution is added while stirring, and 10% sodium hydroxide aqueous solution is used for adjusting the pH value to 8-9, thus producing magnesium hydroxide precipitate. Soaking the magnesium hydroxide precipitate for 12h, filtering to obtain a filter cake, cleaning the filter cake, drying at 112 ℃ for 4h, and roasting at 555 ℃ for 4.5h to obtain magnesium oxide.
The obtained magnesia is immersed in cerium nitrate solution with 15 percent of carrier mass for 12 hours, and dried for 4 hours at 115 ℃ and baked for 5 hours at 556 ℃ to obtain the modified supported magnesia catalyst.
Example 3:
taking 100g of gamma-Al 2 O 3 The carrier (also SiO) 2 ZSM-5, activated carbon or diatomite), adding a proper amount of deionized water (the proper amount of all the infiltration carriers is adopted), adding 24g of 17% magnesium nitrate aqueous solution by mass fraction while stirring, and adjusting the pH to 8-9 by using 10% sodium hydroxide aqueous solution to produce magnesium hydroxide precipitate. And immersing the magnesium hydroxide precipitate for 10 hours, filtering to obtain a filter cake, cleaning the filter cake, drying at 110 ℃ for 5 hours, and roasting at 550 ℃ for 6 hours to obtain magnesium oxide.
The obtained magnesia is immersed in 15 percent of lanthanum nitrate solution with the quality of the carrier for 10 hours, and dried at 110 ℃ for 5 hours and baked at 558 ℃ for 5 hours to obtain the modified supported magnesia catalyst.
Example 4:
taking 100g of gamma-Al 2 O 3 The carrier (also SiO) 2 ZSM-5, activated carbon or diatomite), adding a proper amount of deionized water (the proper amount of all the infiltration carriers is adopted), adding 20g of 20% magnesium nitrate aqueous solution by mass fraction while stirring, and adjusting the pH to 8-9 by using 10% sodium hydroxide aqueous solution to produce magnesium hydroxide precipitate. Soaking the magnesium hydroxide precipitate for 12h, filtering to obtain a filter cake, cleaning the filter cake, drying at 110 ℃ for 5h, and roasting at 550 ℃ for 5h to obtain magnesium oxide.
The obtained magnesia is immersed in 15 percent of lanthanum nitrate solution with the quality of the carrier for 12 hours, and dried at 110 ℃ for 5 hours and baked at 550 ℃ for 5 hours to obtain the modified supported magnesia catalyst.
Determination of monoglyceride content: the content of the monoglyceride is measured by using a GB/T22328-2008 method.
Monoglyceride selectivity assay: monoglyceride mass/(total mass of monoglyceride, diglyceride, and Triglyceride)
Example 5:
0.5 part of the modified supported magnesium oxide catalyst of example 1 was added to a fixed bed reactor; introducing 85 parts of preheated and melted hydrogenated oil and 17 parts of glycerol into a fixed bed reactor for reaction, increasing the temperature to 200 ℃, reacting for 60min, introducing nitrogen, and adjusting the flow rate of the nitrogen to 30ml/min; after the reaction is finished, the reaction liquid is collected and separated to obtain the monoglyceride. The monoglyceride selectivity was found to be 60.8%. (the selectivity of monoglyceride was 62.1% at 120min reaction time).
Example 6:
0.4 part of the modified supported magnesium oxide catalyst of example 1 was added to a fixed bed reactor; introducing 92 parts of preheated and melted hydrogenated grease and 15 parts of glycerol into a fixed bed reactor for reaction, raising the temperature to 197 ℃, reacting for 65min, introducing nitrogen, and adjusting the flow rate of the nitrogen to 50ml/min; after the reaction is finished, the reaction liquid is collected and separated to obtain the monoglyceride. The monoglyceride selectivity was found to be 60.2%.
Example 7:
0.5 part of the modified supported magnesium oxide catalyst of example 1 was added to a fixed bed reactor; introducing 85 parts of preheated and melted hydrogenated oil and 18 parts of glycerol into a fixed bed reactor for reaction, increasing the temperature to 200 ℃, reacting for 120min, introducing nitrogen, and adjusting the flow rate of the nitrogen to 100ml/min; after the reaction is finished, the reaction liquid is collected and separated to obtain the monoglyceride. The monoglyceride selectivity was measured to be 62.2%.
Example 8:
adding 0.7 of the modified supported magnesia catalyst of example 1 to a fixed bed reactor; introducing 82 parts of preheated and melted hydrogenated oil and 15 parts of glycerol into a fixed bed reactor for reaction, increasing the temperature to 200 ℃, reacting for 120min, introducing nitrogen, and adjusting the flow rate of the nitrogen to 50ml/min; after the reaction is finished, the reaction liquid is collected and separated to obtain the monoglyceride. The monoglyceride selectivity was measured to be 62.3%.
Example 9:
adding 0.6 of the modified supported magnesium oxide catalyst of example 1 to a fixed bed reactor; introducing 94 parts of preheated and melted hydrogenated oil and 19 parts of glycerol into a fixed bed reactor for reaction, raising the temperature to 208 ℃, reacting for 85min, introducing nitrogen, and adjusting the flow rate of the nitrogen to 80ml/min; after the reaction is finished, the reaction liquid is collected and separated to obtain the monoglyceride. The monoglyceride selectivity was found to be 61.3%.
Comparative example 1:
the difference from example 5 is that no catalyst was used.
At a reaction time of 1h, a monoglyceride selectivity of 22.4% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 25.9% was measured.
Comparative example 2:
the difference from example 5 is that no catalyst was used and the reaction temperature was 220 degrees celsius.
At a reaction time of 1h, a monoglyceride selectivity of 26.1% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 30.5% was measured.
Comparative example 3:
the difference from example 5 is that no catalyst was used and the reaction temperature was 240 degrees celsius.
At a reaction time of 1h, a monoglyceride selectivity of 34.6% was measured.
At a reaction time of 3h, a monoglyceride selectivity of 40.8% was measured.
Comparative example 4:
the difference from example 5 is that the modified supported magnesium oxide catalyst was replaced with 0.1 part of sodium hydroxide.
At a reaction time of 1h, a monoglyceride selectivity of 29.7% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 33.5% was measured.
Comparative example 5:
the difference from example 5 is that the modified supported magnesium oxide catalyst was replaced with 0.1 part of sodium hydroxide at a reaction temperature of 220 ℃.
At a reaction time of 1h, a monoglyceride selectivity of 37.2% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 44.4% was measured.
Comparative example 6:
the difference from example 5 is that the modified supported magnesium oxide catalyst was replaced with 0.5 part of sodium hydroxide.
At a reaction time of 1h, a monoglyceride selectivity of 32.7% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 36.1% was measured.
Comparative example 7:
the difference from example 5 is that 0.5 part of sodium hydroxide is used for replacing the modified supported magnesium oxide catalyst, and the reaction temperature is 220 DEG C
At a reaction time of 1h, a monoglyceride selectivity of 39.9% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 45.8% was measured.
Comparative example 8:
the difference from example 5 is that the modified supported magnesium oxide catalyst was replaced with 0.5 part of the unmodified supported magnesium oxide catalyst, and the reaction temperature was 200 DEG C
At a reaction time of 1h, a monoglyceride selectivity of 49.6% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 50.1% was measured.
Comparative example 9:
the difference from example 5 is that the modified supported magnesium oxide catalyst was replaced with 0.5 part of the unmodified supported magnesium oxide catalyst, and the reaction temperature was 200 DEG C
At a reaction time of 1h, a monoglyceride selectivity of 54.5% was measured.
At a reaction time of 2h, a monoglyceride selectivity of 55.8% was measured.
The experimental data of the examples 5-9 and the comparative examples 1-9 can be compared, the invention adopts the supported magnesium oxide catalyst, cerium salt or lanthanum salt is added for modification, the selectivity of monoglyceride is improved to more than 60% from 40% in the prior art, the reaction temperature is reduced to 200 ℃ from 220 ℃, the energy consumption is saved, and the cost is saved.
The foregoing is only illustrative of the preferred embodiments and principles of the present invention, and changes in specific embodiments will occur to those skilled in the art upon consideration of the teachings provided herein, and such changes are intended to be included within the scope of the invention as defined by the claims.
Claims (7)
1. The preparation method of the modified supported magnesium oxide catalyst is characterized by comprising the following steps:
s1, soaking a carrier in deionized water, adding a magnesium nitrate aqueous solution while stirring, and adjusting the pH value of the solution by using a sodium hydroxide solution to generate a magnesium hydroxide precipitate; soaking and filtering to obtain a filter cake, and cleaning, drying and roasting the filter cake to obtain magnesium oxide;
s2, impregnating the obtained magnesium oxide with cerium salt or lanthanum salt, and cleaning, drying and roasting after the impregnation is finished to obtain a modified magnesium oxide catalyst;
the carrier is gamma-Al 2 O 3 、SiO 2 ZSM-5 molecular sieve, activated carbon or diatomaceous earth;
the mass fraction of the magnesium nitrate aqueous solution is 16-23%, and the mass of the added magnesium nitrate aqueous solution is 10-25% of the mass of the carrier;
the cerium salt or lanthanum salt is nitrate solution with the mass fraction of 15-25%, and the addition amount of the nitrate solution is 5-25% of the mass of the carrier.
2. The method for preparing a modified supported magnesia catalyst as claimed in claim 1, wherein the mass fraction of the sodium hydroxide solution is 5-15%, and the pH of the solution is adjusted to 8-9.
3. The method for preparing a modified supported magnesia catalyst as claimed in claim 1, wherein in both S1 and S2, the impregnation time is not less than 10 hours, the drying temperature is above 110 ℃, the drying time is 4-6 hours, the calcination temperature is above 550 ℃ and the calcination time is 4-6 hours.
4. The production process of the monoglyceride is characterized by comprising the following steps of:
s11, adding the modified supported magnesium oxide catalyst obtained by the preparation method of any one of claims 1-3 into a fixed bed reactor,
s12, introducing preheated and melted hydrogenated grease and glycerol into a fixed bed reactor for reaction, raising the temperature, introducing nitrogen, and adjusting the flow rate of the nitrogen to 30-100ml/min;
s13, collecting a reaction liquid after the reaction is finished, and separating to obtain the monoglyceride.
5. The process for producing monoglyceride as set forth in claim 4, wherein the reaction temperature in step S2 is 190 to 210 ℃.
6. The process for producing monoglyceride as set forth in claim 4, wherein the reaction time in step S2 is 50 to 130 minutes.
7. The process for producing monoglyceride as set forth in claim 4, wherein the separation method of step S3 is a molecular distillation method.
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