CN102731302A - Method for preparing diester succinate by esterifying diammonium succinate - Google Patents
Method for preparing diester succinate by esterifying diammonium succinate Download PDFInfo
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- CN102731302A CN102731302A CN2012102520232A CN201210252023A CN102731302A CN 102731302 A CN102731302 A CN 102731302A CN 2012102520232 A CN2012102520232 A CN 2012102520232A CN 201210252023 A CN201210252023 A CN 201210252023A CN 102731302 A CN102731302 A CN 102731302A
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Abstract
The invention discloses a method for preparing diester succinate by esterifying diammonium succinate, belonging to the field of chemical technology, and particularly discloses a method for preparing the diester succinate product with the purity of more than 99.8% by taking diammonium succinate as a raw material, contacting the raw material with an esterifying agent in a reactor filled with solid acid catalyst to generate dimethyl succinate crude product and finally refining. The method is simple, mild in technological conditions, reasonable in process flow, less in side reaction, high in product purity and good in quality.
Description
Technical field
The present invention relates to the method that a kind of Succinic Acid two ammonium esterifications prepare succinate, particularly a kind of is the method for feedstock production methyl-succinate with Succinic Acid two ammoniums and methyl alcohol.
Background technology
Methyl-succinate (has another name called Succinic acid dimethylester; CAS:106-65-0) be important synthetic perfume and foodstuff additive; Also be organic synthesis and medicine synthetic midbody, be widely used in industries such as food, spices, daily-use chemical industry, medicine, coating, rubber, plastics.
In the industry, methyl-succinate is to be raw material with Succinic Acid and methyl alcohol, under the katalysis of concentrated sulfuric acid catalyst, obtains through esterification.Adopt the vitriol oil many as the esterification side reaction of catalyzer, product yield is low, and vitriolic corrodibility is strong, and aftertreatment is complicated, and is seriously polluted, can not satisfy environmental protection requirement.
Disclosing a kind of among the U.S. Pat 5872276A is raw material with the dimethyl maleate; Continuous liquid phase hydrogenation prepares the method for methyl-succinate, and this method adopts fixed-bed reactor, and reaction pressure is 30 MPas; Temperature of reaction is 40-100 ℃, and liquid hourly space velocity is 0.6-1.5g/ml Cat.h
-1But the reaction pressure height that this method hydrogenation is required, facility investment is big, and process cost is high.
Chinese patent CN101824627 has announced that a kind of is the method that raw material is produced methyl-succinate with cis-butenedioic anhydride and methyl alcohol; The synthetic dimethyl maleate of cis-butenedioic anhydride and methyl alcohol catalytic esterification under the katalysis of sulfuric acid or hydrochloric acid, the electrolytic reduction dimethyl maleate generates methyl-succinate then.With cis-butenedioic anhydride and methyl alcohol is that the raw material production methyl-succinate is the raw material production methyl-succinate than with the Succinic Acid, the reaction more easily, more thorough.But this method is used sulfuric acid or hydrochloric acid in esterification process, equipment corrosion, and the difficult problem of catalyzer and product separation does not still solve.In addition, current efficiency and feed stock conversion are not high in the dimethyl maleate electrolytic reduction synthesis of dimethyl succinate, and whole process energy consumption, supplies consumption are bigger, are unfavorable for large-scale production.
Announced and a kind ofly produced the method for methyl-succinate to have characteristics such as product purity height, quality be good among the Chinese patent CN101824627A with the dimethyl maleate hydrogenation.But this method product separation process is long, energy consumption is big, main raw material is difficult for obtaining, and is unfavorable for large-scale industrial production.
Summary of the invention
The present invention adopts reactive distillation processes, utilizes Succinic Acid two aqueous ammoniums and esterifying agent generation catalytic esterification to generate succinate, and in reaction process, in time removes the ammonia G&W that is produced.The present invention has improved the Zhi Huadu of Succinic Acid two ammoniums, has guaranteed that the yield of succinate has arrived 90-100%.Simultaneously, suppressed production of by-products, the content of nitrogen element is below 1% in the product.
Particularly, the invention provides and a kind ofly prepare the method for succinate by Succinic Acid two ammonium esterifications, it may further comprise the steps:
(1) at first Succinic Acid two aqueous ammoniums and esterifying agent mol ratio and the stream with 1:2.5 to 1:10 is joined in the reaction kettle, add catalyzer simultaneously, and in reaction kettle, pour nitrogen;
(2) under 120 ℃-230 ℃ temperature, make Succinic Acid two ammoniums in the reaction kettle carry out alcoholysis reaction, reaction was carried out 8～14 hours;
(3) in the reaction process; The gas-phase product on reaction kettle top is separated into ammonia, esterifying agent and water through condensing surface and gas-liquid separator, and ammonia gets into the ammonia recovery system; Esterifying agent and water remove the water that dereaction generates through dehumidification system, and dried esterifying agent returns in the reaction kettle;
(4) after reaction finished, the still bottom product leads to azeotropic rose in the rectifying tower, and added entrainer and distill, and the bottom product that obtains is corresponding succinate;
Wherein, the mass concentration of Succinic Acid two aqueous ammoniums is 40% to 90% described in the step (1), and esterifying agent is the C1～C6 alkyl alcohol of straight or branched, and catalyzer is a solid acid catalyst, for example, and γ-Al
2O
3, H
3PO
4-zeyssatite, Al
2O
3/ MgO, SiO
2-Al
2O
3, the ZSM-5 molecular sieve; SAPO-34 molecular sieve etc.; The add-on of catalyzer is 8～10% of Succinic Acid two ammonium solutions, and the pressure in the reaction kettle is 0.1～1.5Mpa, and entrainer is a kind of in chloroform, tetracol phenixin, benzene, toluene, acetonitrile, Virahol, pyridine, n-propyl alcohol, the ETHYLE ACETATE.
In above-mentioned steps (1), the mass concentration of said Succinic Acid two aqueous ammoniums is preferably 40～80%, and more preferably 60%.
In above-mentioned steps (1), said esterifying agent is preferably methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol or the trimethyl carbinol, more preferably methyl alcohol.
In above-mentioned steps (1), the mol ratio of said Succinic Acid two aqueous ammoniums and esterifying agent is preferably 1:5 to 1:10, more preferably 1:10.
In above-mentioned steps (1), said catalyzer is preferably SiO
2-Al
2O
3
In above-mentioned steps (2), temperature of reaction is preferably 170 ℃～190 ℃, more preferably 170 ℃.
In above-mentioned steps (2), the reaction times is preferably 10～14 hours, more preferably 10 hours.
In above-mentioned steps (4), the pressure of said rectifying is 0.2-1.0MPa, and tower top temperature 64-72 ℃, column bottom temperature 85-120 ℃, distillation time is 1.5-3h.
The method for preparing succinate in method of the present invention and the prior art is compared has following advantage:
(1) adopt solid acid catalyst, simplified separation process, the entire reaction flow process is simple, little to corrosion on Equipment, energy consumption is low, pollution-free.
(2) in esterification workshop section, adopt reaction distillation technology, shift out the ammonia G&W that reaction produces, improved the transformation efficiency of Succinic Acid two ammoniums, the transformation efficiency of Succinic Acid two ammoniums has reached more than 80%, and the selectivity of methyl-succinate is greater than 99%.
(3) in product purification rectifying workshop section, product separation is simple, good product quality, and purity is high.
Description of drawings
Fig. 1 is the mass spectrum of prepared succinate.
Fig. 2 is the nuclear magnetic resonance spectrum of prepared succinate.
Embodiment
Through embodiment the present invention is further specified below, but the scope that scope of the present invention is not only limited to embodiment to be covered.Described Succinic Acid two ammoniums of the application are available from Baoji precious jade chemical industry ltd.
Embodiment 1
7.6g Succinic Acid two ammoniums are added in 11.4 water, obtain 19g Succinic Acid two ammonium mass concentrations and be 40% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 120 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 62-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 1 of seeing after.
Embodiment 2
7.6g Succinic Acid two ammoniums are added in 7.6 water, obtain 15.2g Succinic Acid two ammonium mass concentrations and be 50% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 150 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 1 of seeing after.
Embodiment 3
7.6g Succinic Acid two ammoniums are added in 5.07 water, obtain 12.67g Succinic Acid two ammonium mass concentrations and be 60% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 150 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 1 of seeing after.
Embodiment 4
7.6g Succinic Acid two ammoniums are added in 3.26 water, and configuration 10.86g Succinic Acid two ammonium mass concentrations are 70% solution, and this solution with 20ml methyl alcohol and flow and join in the reaction kettle, is added catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 150 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 1 of seeing after.
The result of table 1 embodiment 1-embodiment 4
Embodiment 5
7.6g Succinic Acid two ammoniums are added in 3.26 water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 120 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 2 of seeing after.
Embodiment 6
7.6g Succinic Acid two ammoniums are added in the 3.26g water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 150 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 2 of seeing after.
Embodiment 7
7.6g Succinic Acid two ammoniums are added in the 3.26g water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 170 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 2 of seeing after.
Embodiment 8
7.6g Succinic Acid two ammoniums are added in the 3.26g water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyst A l simultaneously
2O
3/ MgO 0.6g feeds nitrogen in reaction kettle, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 190 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 2 of seeing after.
The result of table 2 embodiment 5-embodiment 8
7.6g Succinic Acid two ammoniums are added in the 3.26g water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 170 ℃, and the reaction times is 8h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 3 of seeing after.
Embodiment 10
7.6g Succinic Acid two ammoniums are added in the 3.26g water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 170 ℃, and the reaction times is 10h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 3 of seeing after.
Embodiment 11
7.6g Succinic Acid two ammoniums are added in 3.26 water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 170 ℃, and the reaction times is 12h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 3 of seeing after.
Embodiment 12
7.6g Succinic Acid two ammoniums are added in 3.26 water, obtain 10.86g Succinic Acid two ammonium mass concentrations and be 70% solution, this solution and 20ml methyl alcohol and stream are joined in the reaction kettle, add catalyzer (SiO simultaneously
2-Al
2O
3) 0.6g, in reaction kettle, feed nitrogen, make reacting kettle inner pressure be promoted to 0.2Mpa.Temperature of reaction is 170 ℃, and the reaction times is 14h.
The stage number of succinate azeotropy rectification column is 15, adds 16g ETHYLE ACETATE as entrainer, and reflux ratio is 1, and tower top temperature is 60-65 ℃, and column bottom temperature is 90-100 ℃.The mass spectrum of prepared succinate is as shown in Figure 1, and nuclear magnetic resonance spectrum is as shown in Figure 2.
The experimental result table 3 of seeing after.
The result of table 3 embodiment 9-embodiment 12
Can be found out that by above result when Succinic Acid two aqueous ammonium concentration are 70%, temperature of reaction is 170 ℃, the reaction times, the by product that method as herein described obtains was few when being 10 hours, and the cost of raw material is low, and product purity is high.
Claims (10)
1. one kind prepares the method for succinate by Succinic Acid two ammonium esterifications, and it may further comprise the steps:
(1) at first Succinic Acid two aqueous ammoniums and esterifying agent mol ratio and the stream with 1:2.5 to 1:10 is joined in the reaction kettle, add catalyzer simultaneously, and in reaction kettle, pour nitrogen;
(2) under 120 ℃-230 ℃ temperature, make Succinic Acid two ammoniums in the reaction kettle carry out alcoholysis reaction, reaction was carried out 8～14 hours;
(3) in the reaction process; The gas-phase product on reaction kettle top is separated into ammonia, esterifying agent and water through condensing surface and gas-liquid separator, and ammonia gets into the ammonia recovery system; Esterifying agent and water remove the water that dereaction generates through dehumidification system, and dried esterifying agent returns in the reaction kettle;
(4) after reaction finished, the still bottom product leads to azeotropic rose in the rectifying tower, and added entrainer and distill, and the bottom product that obtains is corresponding succinate;
Wherein, the mass concentration of Succinic Acid two aqueous ammoniums is 40% to 90% described in the step (1), and esterifying agent is the C1～C6 alkyl alcohol of straight or branched, and catalyzer is γ-Al
2O
3, H
3PO
4-zeyssatite, Al
2O
3/ MgO, SiO
2-Al
2O
3, ZSM-5 molecular sieve or SAPO-34 molecular sieve; The add-on of catalyzer is 8～10% of Succinic Acid two ammonium solutions; Pressure in the reaction kettle is 0.1～1.5Mpa, and entrainer is a kind of in chloroform, tetracol phenixin, benzene, toluene, acetonitrile, Virahol, pyridine, n-propyl alcohol, the ETHYLE ACETATE.
2. method according to claim 1, wherein, said esterifying agent is a methyl alcohol, said succinate is a methyl-succinate.
3. method according to claim 1, wherein, said catalyzer is SiO
2-Al
2O
3
4. method according to claim 1, the mass concentration of wherein said Succinic Acid two aqueous ammoniums is 40～80%.
5. method according to claim 1, wherein, the temperature of reaction of said step (2) is 170 ℃～190 ℃.
6. method according to claim 1, wherein, the reaction times of said step (2) is 10～14 hours.
7. method according to claim 1, the mass concentration of wherein said Succinic Acid two aqueous ammoniums is 70%.
8. method according to claim 1, wherein, the temperature of reaction of said step (2) is 170 ℃.
9. method according to claim 1, wherein, the reaction times of said step (2) is 10 hours.
10. method according to claim 1, wherein, the pressure of said step (4) rectifying is 0.2-1.0MPa, tower top temperature 64-72 ℃, column bottom temperature 85-120 ℃, distillation time is 1.5-3h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015082077A1 (en) * | 2013-12-06 | 2015-06-11 | Thyssenkrupp Industrial Solutions Ag | Process for the preparation and isolation of carboxylic esters |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1337940A (en) * | 1999-02-03 | 2002-02-27 | 三星精密化学株式会社 | A process for preparing (R)-4-cyano-3-hydroxybutyric acid ester |
| CN101323566A (en) * | 2007-06-11 | 2008-12-17 | 深圳市飞扬实业有限公司 | Preparation method of diethyl succinate |
-
2012
- 2012-07-19 CN CN201210252023.2A patent/CN102731302B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1337940A (en) * | 1999-02-03 | 2002-02-27 | 三星精密化学株式会社 | A process for preparing (R)-4-cyano-3-hydroxybutyric acid ester |
| CN101323566A (en) * | 2007-06-11 | 2008-12-17 | 深圳市飞扬实业有限公司 | Preparation method of diethyl succinate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015082077A1 (en) * | 2013-12-06 | 2015-06-11 | Thyssenkrupp Industrial Solutions Ag | Process for the preparation and isolation of carboxylic esters |
| US9963414B2 (en) | 2013-12-06 | 2018-05-08 | Thyssenkrupp Industrial Solutions Ag | Process for the preparation and isolation of carboxylic esters |
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