CN115073324B - Method for preparing glutarimide by homogeneous catalysis - Google Patents

Method for preparing glutarimide by homogeneous catalysis Download PDF

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CN115073324B
CN115073324B CN202210790690.XA CN202210790690A CN115073324B CN 115073324 B CN115073324 B CN 115073324B CN 202210790690 A CN202210790690 A CN 202210790690A CN 115073324 B CN115073324 B CN 115073324B
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homogeneous catalyst
glutarimide
acid
pentanediamine
synthesis reaction
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CN115073324A (en
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王利国
惠祥
陈家强
曹妍
李会泉
贺鹏
徐爽
郑征
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Institute of Process Engineering of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The present invention provides a method for preparing glutarimide by using homogeneous catalyst, the method comprises: mixing pentanediamine, dimethyl carbonate and a homogeneous catalyst to perform carbonylation synthesis reaction to obtain glutarimide; wherein the homogeneous catalyst comprises an organic acid and/or water. The method provided by the invention improves the catalytic efficiency and the yield of the target product, simplifies the process flow, reduces the preparation cost and is suitable for industrial production.

Description

Method for preparing glutarimide by homogeneous catalysis
Technical Field
The invention belongs to the technical field of chemical synthesis, relates to a method for preparing glutarimide, and in particular relates to a method for preparing glutarimide by using a homogeneous catalyst.
Background
The glutarimide (PDC) is a bio-based carbamate, and the synthesis raw material of the glutarimide (PDA) is obtained by biomass fermentation, so that the PDC has good application prospect in the future market. The PDC can be used for synthesizing substances such as isocyanate, polyurethane and the like, and is applied to the industrial fields such as automobiles, wind power and the like and the daily necessities industry such as artificial leather, leather shoes and the like. With the large-scale production of PDA biological methods, researchers are focusing more and more on the synthesis of PDC. In the synthesis process of PDC, the action of the catalyst is crucial, and current reports about PDC synthesis at home and abroad are very few.
CN 108689884a discloses a preparation method of 1, 5-pentanediisocyanate, comprising the following steps: (1) Mixing the 1, 5-pentanediamine conversion solution with an extraction solvent to extract 1, 5-pentanediamine, and then dehydrating the extraction solution to obtain a mixed solution of 1, 5-pentanediamine and the extraction solvent; (2) Adding a catalyst and urea into a mixed solution of 1, 5-pentanediamine and an extraction solvent, supplementing a proper amount of the extraction solvent to form a reaction system, carrying out carbamate formation on the 1, 5-pentanediamine, and recovering excessive extraction solvent in the reaction system through reduced pressure distillation to obtain PDU; (3) And mixing PDU, a heat carrier and a catalyst for thermal cracking reaction, and separating to obtain an extraction solvent and PDI. According to the preparation method, zirconium acetate is adopted to catalyze urea and PDA extract to carry out carbamate synthesis, however, polyurea byproducts are easy to generate in the carbonylation process, the yield is reduced in practical application, and a pipeline is blocked.
CN113603613a discloses a catalytic synthesis method of glutarimide, which comprises adding pentylene diamine and carbonylation agent into solvent to dissolve, and carrying out catalytic synthesis reaction by titanium dioxide catalyst. The catalytic synthesis method adopts a solid-phase catalyst, so that the efficiency of catalytic reaction is limited, the catalyst needs to be separated after the reaction is finished, and the process flow is complex.
Therefore, how to provide a preparation method of glutarimide, further improving the catalytic efficiency and the yield of target products, simplifying the process flow, reducing the preparation cost, being applicable to industrial production and becoming the urgent problem to be solved by the current technicians in the field.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a method for preparing glutarimide by using a homogeneous catalyst, which improves the catalytic efficiency and the yield of target products, simplifies the process flow, reduces the preparation cost and is suitable for industrial production.
To achieve the purpose, the invention adopts the following technical scheme:
the invention provides a method for preparing glutarimide by homogeneous catalysis, which comprises the following steps: and mixing the pentanediamine, the dimethyl carbonate and the homogeneous catalyst to perform carbonylation synthesis reaction to obtain the pentanediamine carbamate.
Wherein the homogeneous catalyst comprises an organic acid and/or water.
In the preparation process of the glutarimide, organic acid and/or water is selected as a homogeneous phase catalyst, compared with the traditional heterogeneous catalytic reaction, the catalytic efficiency of the homogeneous catalytic reaction is higher, the yield of a target product can reach more than 90%, and the glutarimide can be automatically separated out at normal temperature when only water is selected as the homogeneous catalyst, so that the separation step is reduced, the process flow is simplified, the preparation cost is reduced, and the preparation method is suitable for industrial production.
Preferably, the organic acid comprises any one or a combination of at least two of acetic acid, propionic acid, malonic acid, butyric acid, glycine, alanine or lysine, typically but not limited to a combination of acetic acid and propionic acid, a combination of propionic acid and malonic acid, a combination of malonic acid and butyric acid, a combination of butyric acid and glycine, a combination of glycine and alanine, a combination of alanine and lysine, acetic acid, propionic acid and malonic acid, a combination of propionic acid and butyric acid, a combination of malonic acid, butyric acid and glycine, a combination of butyric acid, glycine and alanine, a combination of glycine, alanine and lysine, a combination of acetic acid, propionic acid, malonic acid and butyric acid, a combination of malonic acid, butyric acid, glycine and alanine, or a combination of butyric acid, glycine, alanine and lysine.
Preferably, the molar ratio of the pentylene diamine, the dimethyl carbonate and the homogeneous catalyst is 1 (2-10): (2-12), for example, 1:2:2, 1:2:4, 1:2:6, 1:2:8, 1:2:10, 1:2:12, 1:5:2, 1:5:4, 1:5:6, 1:5:8, 1:5:10, 1:5:12, 1:10:2, 1:10:4, 1:10:6, 1:10:8, 1:10:10 or 1:10:12, further preferably 1 (2-5): (2-6), but not limited to the recited values, other non-recited values within the range of values are equally applicable.
Preferably, the homogeneous catalyst comprises an organic acid and water.
Preferably, the molar ratio of the organic acid to water is 1 (2-4), and may be, for example, 1:2, 1:2.2, 1:2.4, 1:2.6, 1:2.8, 1:3, 1:3.2, 1:3.4, 1:3.6, 1:3.8 or 1:4, but is not limited to the recited values, and other non-recited values within the range of values are equally applicable.
The invention prefers the mixed solution of the organic acid and the water as the homogeneous catalyst, strictly limits the mixed molar ratio within a reasonable range, can further improve the catalytic efficiency and the yield of the target product, and simultaneously reduces the cost of the catalyst as much as possible, thereby improving the economic benefit and being beneficial to industrial production.
The temperature of the carbonylation synthesis reaction is preferably 50 to 120 ℃, and may be, for example, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃, 100 ℃, 110 ℃, or 120 ℃, and more preferably 50 to 100 ℃, but is not limited to the recited values, and other non-recited values within the range are equally applicable.
In the invention, the temperature of the carbonylation synthesis reaction is controlled within a reasonable range. When the temperature is lower than 50 ℃, the catalytic efficiency is too low, and the yield of the target product is less than 90%; when the temperature is higher than 120 ℃, side reactions are increased, the yield of the target product is reduced, and meanwhile, the energy consumption is increased, so that the preparation cost is not saved.
Preferably, the time of the carbonylation synthesis reaction is 0.5 to 10 hours, for example, 0.5 hours, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours or 10 hours, and more preferably 2 to 8 hours, but not limited to the recited values, and other non-recited values within the range are equally applicable.
Preferably, the carbonylation synthesis reaction is also accompanied by agitation.
Preferably, the stirring speed is 100-1000rpm, for example, 100rpm, 200rpm, 300rpm, 400rpm, 500rpm, 600rpm, 700rpm, 800rpm, 900rpm or 1000rpm, but not limited to the recited values, and other non-recited values within the range of values are equally applicable.
As a preferred technical solution of the present invention, the method includes:
mixing (2-6) pentanediamine, dimethyl carbonate and a homogeneous catalyst according to the mol ratio of (2-5), and carrying out carbonylation synthesis reaction for 2-8 hours at 50-100 ℃ with stirring at the speed of 100-1000rpm to obtain glutarimide; wherein the homogeneous catalyst comprises an organic acid and water in a mixed molar ratio of 1 (2-4), and the organic acid comprises any one or a combination of at least two of acetic acid, propionic acid, malonic acid, butyric acid, glycine, alanine or lysine.
The numerical ranges recited herein include not only the above-listed point values, but also any point values between the above-listed numerical ranges that are not listed, and are limited in space and for the sake of brevity, the present invention is not intended to be exhaustive of the specific point values that the stated ranges include.
Compared with the prior art, the invention has the beneficial effects that:
in the preparation process of the glutarimide, organic acid and/or water is selected as a homogeneous catalyst, compared with the traditional heterogeneous catalytic reaction, the catalytic efficiency of the homogeneous catalytic reaction is higher, the yield of a target product can reach more than 90%, and the glutarimide can be automatically separated out at normal temperature when only water is selected as the homogeneous catalyst, so that the separation step is reduced, the process flow is simplified, the preparation cost is reduced, and the preparation method is suitable for industrial production.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments.
Example 1
This example provides a process for preparing glutarimide using a homogeneous catalyst, the process comprising: mixing pentanediamine, dimethyl carbonate and a homogeneous catalyst according to a molar ratio of 1:3:4, and performing carbonylation synthesis reaction at 80 ℃ for 5 hours with stirring at a speed of 500rpm to obtain pentanediamine carbamate; wherein the homogeneous catalyst is acetic acid and water in a mixed molar ratio of 1:3.
Example 2
This example provides a process for preparing glutarimide using a homogeneous catalyst, the process comprising: mixing pentanediamine, dimethyl carbonate and a homogeneous catalyst according to a molar ratio of 1:5:6, and carrying out carbonylation synthesis reaction at 60 ℃ for 8 hours with stirring at a speed of 300rpm to obtain pentanediamine carbamate; wherein the homogeneous catalyst is propionic acid and water in a mixed molar ratio of 1:2.
Example 3
This example provides a process for preparing glutarimide using a homogeneous catalyst, the process comprising: mixing pentanediamine, dimethyl carbonate and a homogeneous catalyst according to a molar ratio of 1:2:2, and carrying out carbonylation synthesis reaction at 100 ℃ for 0.5h with stirring at a speed of 800rpm to obtain glutarimide; wherein the homogeneous catalyst is butyric acid and water with a mixed molar ratio of 1:4.
Example 4
This example provides a process for preparing glutarimide using a homogeneous catalyst, the process comprising: the pentanediamine, the dimethyl carbonate and the glycine are mixed according to the mol ratio of 1:10:2, and the carbonylation synthesis reaction is carried out for 10 hours at 50 ℃ with stirring at the speed of 100rpm, so as to obtain the pentanediamine carbamate.
Example 5
This example provides a process for preparing glutarimide using a homogeneous catalyst, the process comprising: the pentanediamine, the dimethyl carbonate and the water are mixed according to the mol ratio of 1:2:12, and the carbonylation synthesis reaction is carried out for 2 hours at 120 ℃ with the stirring with the speed of 1000rpm, so as to obtain the pentanediamine carbamate.
Example 6
This example provides a method for preparing glutarimide by using a homogeneous catalyst, and the other conditions are the same as those in example 1 except that the mixing molar ratio of pentanediamine, dimethyl carbonate and homogeneous catalyst is changed to 1:1:1, so that no description is given here.
Example 7
This example provides a method for preparing glutarimide by using a homogeneous catalyst, and the other conditions are the same as those in example 1 except that the mixing molar ratio of pentanediamine, dimethyl carbonate and homogeneous catalyst is changed to 1:12:14, so that no description is repeated here.
Example 8
This example provides a method for preparing glutarimide using a homogeneous catalyst, and the conditions of the method are the same as those of example 1 except that the mixing molar ratio of acetic acid and water in the homogeneous catalyst is changed to 1:1, so that no description is given here.
Example 9
This example provides a method for preparing glutarimide using a homogeneous catalyst, and the conditions of the method are the same as those of example 1 except that the mixing molar ratio of acetic acid and water in the homogeneous catalyst is changed to 1:5, so that no description is given here.
Example 10
This example provides a method for preparing glutarimide using homogeneous catalyst, and the conditions of the method are the same as those of example 1 except that the temperature of the carbonylation reaction is reduced to 40 ℃.
Example 11
This example provides a method for preparing glutarimide using homogeneous catalyst, and the conditions of the method are the same as those of example 1 except that the temperature of the carbonylation reaction is raised to 130 ℃.
Example 12
The present embodiment provides a method for preparing glutarimide using homogeneous catalyst, which shortens the time of carbonylation synthesis reaction to 0.3h, and the other conditions are the same as those of embodiment 1, so that the description thereof will not be repeated here.
Example 13
This example provides a method for preparing glutarimide using homogeneous catalyst, which is the same as example 1 except that the time of the carbonylation synthesis reaction is prolonged to 12 hours, so that the description thereof will be omitted.
Example 14
The present embodiment provides a method for preparing glutarimide by using a homogeneous catalyst, and the method is the same as that of embodiment 1 except that stirring operation is not performed during the carbonylation synthesis reaction, so that no description is given here.
Comparative example 1
This comparative example provides a process for the preparation of glutarimide using the titanium dioxide prepared in example 1 of CN113603613a as catalyst, in particular by: the pentanediamine, dimethyl carbonate and titanium dioxide catalyst were mixed in a molar ratio of 1:3:4, and the carbonylation reaction was carried out at 80℃for 6 hours with stirring at a rate of 300rpm to give the pentanediamine.
The products obtained in examples 1-14 and comparative example 1 were subjected to composition analysis using gas chromatography techniques under the following conditions:
chromatographic column model RTX-5; the column temperature is initially 50 ℃, 1min is reserved, 20 ℃/min is increased to 150 ℃, 1min is reserved, 20 ℃/min is increased to 220 ℃, and 12min is reserved at 220 ℃; the control mode is pressure control, the pressure is 110kPa, the purge flow is 3mL/min, and the split ratio is 25; the gasification temperature was 250 ℃.
The results of the composition analysis of the products obtained in examples 1 to 14 and comparative example 1 are shown in Table 1 below.
TABLE 1
Group of PDA conversion (%) PDC yield (%)
Example 1 98 95
Example 2 99 97
Example 3 94 90
Example 4 99 93
Example 5 98 91
Example 6 96 85
Example 7 99 87
Example 8 99 93
Example 9 99 88
Example 10 93 85
Example 11 95 88
Example 12 90 80
Example 13 95 90
Example 14 92 86
Comparative example 1 55 13
As can be seen from table 1: efficient synthesis of PDC can be achieved using water and/or organic acids as homogeneous catalysts. From a comparison of example 1, example 6 and example 7, it can be seen that: the ratio of the raw materials to the catalyst has obvious influence on the reaction yield. When the dosage of the dimethyl carbonate and the catalyst is too small, the reactant is reduced, and the reaction is insufficient; when the dimethyl carbonate is excessive, there is also a significant drop in the yield of PDC. From a comparison of example 1, example 8 and example 9, it can be seen that: the mixing ratio of water and organic acid has a certain influence on the yield of glutarimide. With the increase of the acid proportion, the yield of PDC is increased; when the amount of water used is large, the yield of PDC is lowered. From a comparison of example 1, example 10 and example 11, it can be seen that: a reaction temperature exceeding the preferable range adversely affects the yield of glutarimide. Too high a temperature may be accompanied by the formation of a portion of byproducts; too low a temperature will in turn lead to a reduced conversion of PDA. From a comparison of example 1, example 12 and example 13, it can be seen that: the reaction time is too short, and the reaction of the pentanediamine and the dimethyl carbonate is insufficient; the reaction time is too long, and other side reactions occur, so that the yield of PDC is reduced. From a comparison of example 1 and example 14, it can be seen that: stirring has a certain promotion effect on the reaction, and can promote mass and heat transfer, thereby improving the yield of PDC. As can be seen from example 1 and comparative example 1: when TiO is used 2 When used as a catalyst, the catalyst effect is obviously reduced, which indicates that TiO 2 Is not suitable for catalyzing the reaction of dimethyl carbonate and pentanediamine carbonylation under mild conditions.
Therefore, compared with the traditional heterogeneous catalytic reaction, the homogeneous catalytic reaction has higher catalytic efficiency, the yield of the target product can reach more than 90%, and when only water is used as the homogeneous catalyst, the glutarimide can be automatically separated out at normal temperature, so that the separation step is reduced, the process flow is simplified, the preparation cost is reduced, and the method is suitable for industrial production.
While the foregoing is directed to embodiments of the present invention, other and further details of the invention may be had by the present invention, it should be understood that the foregoing description is merely illustrative of the present invention and that no limitations are intended to the scope of the invention, except insofar as modifications, equivalents, improvements or modifications are within the spirit and principles of the invention.

Claims (9)

1. A process for preparing glutarimide using a homogeneous catalyst, the process comprising: mixing pentanediamine, dimethyl carbonate and a homogeneous catalyst, and performing carbonylation synthesis reaction at 50-120 ℃ to obtain glutarimide;
wherein the homogeneous catalyst is organic acid and water with a mixed molar ratio of 1 (2-4), and the organic acid is any one or a combination of at least two of acetic acid, propionic acid, malonic acid, butyric acid, glycine, alanine or lysine.
2. The method according to claim 1, wherein the mixing molar ratio of the pentanediamine, the dimethyl carbonate and the homogeneous catalyst is 1 (2-10): 2-12.
3. The method according to claim 2, wherein the mixing molar ratio of the pentanediamine, the dimethyl carbonate and the homogeneous catalyst is 1 (2-5): 2-6.
4. The process according to claim 1, wherein the temperature of the carbonylation synthesis reaction is 50-100 ℃.
5. The process according to claim 1, wherein the time of the carbonylation synthesis reaction is from 0.5 to 10 hours.
6. The process according to claim 5, wherein the time of the carbonylation synthesis reaction is from 2 to 8 hours.
7. The process according to claim 1, wherein the carbonylation synthesis reaction is further accompanied by agitation.
8. The method of claim 7, wherein the stirring is at a rate of 100-1000rpm.
9. The method according to any one of claims 1-8, characterized in that the method comprises: mixing (2-6) pentanediamine, dimethyl carbonate and a homogeneous catalyst according to the mol ratio of (2-5), and carrying out carbonylation synthesis reaction for 2-8 hours at 50-100 ℃ with stirring at the speed of 100-1000rpm to obtain glutarimide; wherein the homogeneous catalyst is organic acid and water with a mixed molar ratio of 1 (2-4), and the organic acid is any one or a combination of at least two of acetic acid, propionic acid, malonic acid, butyric acid, glycine, alanine or lysine.
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Publication number Priority date Publication date Assignee Title
DE3632010A1 (en) * 1986-09-20 1988-04-07 Basf Ag NEW 2- (ALKOXYMETHYL) PENTANE-1,5-DIISOCYANATE, DIURETHANE AND DICARBAMID ACID CHLORIDE, METHOD FOR THE PRODUCTION AND USE THEREOF
CN101468959A (en) * 2007-12-28 2009-07-01 中国科学院兰州化学物理研究所 Method for synthesizing hexamethylene carbamate
CN101260068A (en) * 2008-04-15 2008-09-10 中国科学院山西煤炭化学研究所 Method for preparing methyl 4-(4'-aminophenylmethylene)phenylaminoformate
CN102134205A (en) * 2010-01-25 2011-07-27 湖南大学 Method for preparing carbamate
CN103936623B (en) * 2014-04-15 2015-06-10 河北工业大学 Process for preparing toluene diisocyanate (TDI) by using toluenediamine and dimethyl carbonate
CN108689884A (en) * 2018-08-01 2018-10-23 南京工业大学 A kind of preparation method of penta diisocyanate of 1,5-
CN114105825A (en) * 2020-08-27 2022-03-01 中国科学院过程工程研究所 Preparation method of 1, 5-pentamethylene diisocyanate
CN113603613B (en) * 2021-04-14 2022-08-19 中国科学院过程工程研究所 Catalytic synthesis method of pentanedicarbamic acid ester

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