CN104016861A - Preparation method for synthesis of ethyl 3-ethoxypropionate - Google Patents
Preparation method for synthesis of ethyl 3-ethoxypropionate Download PDFInfo
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- CN104016861A CN104016861A CN201410235205.8A CN201410235205A CN104016861A CN 104016861 A CN104016861 A CN 104016861A CN 201410235205 A CN201410235205 A CN 201410235205A CN 104016861 A CN104016861 A CN 104016861A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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- Y02P20/584—Recycling of catalysts
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Abstract
The invention relates to the technical field of chemical synthesis, and particularly relates to a preparation method for synthesis of ethyl 3-ethoxypropionate; the ethyl 3-ethoxypropionate is synthesized by addition reaction of absolute ethanol and ethyl acrylate in the presence of a catalyst in a tubular reactor, the molar ratio of absolute ethanol to ethyl acrylate is 3: 1 to 100: 1, the catalyst weight accounting for 0.1% to 20% of the weight of the ethyl acrylate; the catalyst is anion exchange resin, and the method has the advantages of simple synthesis, mild condition, less side reaction, recycling and regeneration of the catalyst without damage, great simplification of the separation process, easy continuous production and the like.
Description
[technical field]
The present invention relates to technical field of chemical synthesis, be specifically related to a kind of preparation method of synthetic 3-ethoxyl ethyl propionate.
[background technology]
3-ethoxyl ethyl propionate is a kind of important organic solvent and organic synthesis intermediate, is widely used in coating industry, electron trade and medicine intermediate synthetic.
US Patent No. 5081285 adopts ethanol and ethyl propenoate under the catalysis of methylsulfonic acid, to obtain 3-ethoxyl ethyl propionate, temperature of reaction 120-130 degree, yield 41%, this scheme need to be at stress reaction, be not easy to produce, and temperature of reaction is high, side reaction is many, high cost.
Document [Tetrahedro letters, 46 (19), 3279-3282:2005] to adopt the Potassium monofluoride of aluminium sesquioxide load be that catalyzer has synthesized 3-ethoxyl ethyl propionate with ethanol and ethyl propenoate, it is solvent that process is used acetonitrile, yield 90%, but a large amount of solvent needs recovery and 20 hours reaction times, time is oversize, affects production efficiency.
Patent CN200810061996.1 adopts the basic metal such as sodium Metal 99.5 or alkali metal alcoholates to make catalyzer, with dehydrated alcohol and the synthetic 3-ethoxyl ethyl propionate of ethyl propenoate, reaction times shortened in 3 hours, yield is the highest can reach 96%, but also exist catalyzer to acid, water electrode is responsive, once meeting water or acid suffers to destroy and cannot regenerate, and reaction finishes to remove to destroy catalyzer with acid and makes system neutrality even acid, this has increased the step separating, and reaction generates organic salt has increased the difficulty that product is purified, and the heat release of N-process height has increased side reaction.
[summary of the invention]
The object of the invention is to defect and deficiency for prior art, a kind of preparation method of a kind of synthetic 3-ethoxyl ethyl propionate reasonable in design, easy to use is provided, its employing is passed through the synthetic of tubular reactor with dehydrated alcohol and ethyl propenoate under catalyzer, has and synthesizes simply, mild condition, side reaction is few, catalyst recirculation is used, and need not destroy, and can regenerate, greatly simplify sepn process, be convenient to the advantages such as serialization production.
The preparation method of a kind of synthetic 3-ethoxyl ethyl propionate of the present invention, its preparation method:
It comprises dehydrated alcohol and ethyl propenoate, and this dehydrated alcohol and ethyl propenoate obtain 3-ethoxyl ethyl propionate by the addition of tubular reactor under catalyzer; The mol ratio of described dehydrated alcohol and ethyl propenoate is 3: 1～100: 1, and catalyzer accounts for the ethyl propenoate of weight ratio 0.1%～20%; Described catalyzer is anionite-exchange resin;
Its reaction preparation process is as follows:
(1), use fixed bed system, preferably tubular type or tower reactor, catalyzer is fixed on the inside;
(2), first use dehydrated alcohol cleaning catalyst, and then with nitrogen purging, then use deionized water wash, and then with nitrogen purging, use afterwards 2～10% alkali lye processing, after handling, wash with water, then fill nitrogen;
(3), then wash filling under nitrogen with fresh ethanol or the mixture of ethanol and ethyl propenoate, then filling under nitrogen by washing with alcohol, until the moisture of the ethanol after the cleaning of system the inside is not more than the moisture in raw material dehydrated alcohol;
(4), the activity of successive reaction rear catalyst can decline gradually, when unreacted acrylate in mixture exceedes 1%, considers catalyst regeneration.
(5), moisture can affect reaction, should be controlled in 0.01～0.5%;
(6), temperature of reaction is between-5～35 degree;
(9), reaction is homogeneous phase substantially, except catalyzer is solid, reaction is catalyst fixed bed or material and catalyzer are uniformly mixed by one the material that mixes, can successive reaction, also can be semicontinuous, also can batch carry out;
(10), product 3-ethoxyl ethyl propionate from the feed separation of having reacted out, excessive dehydrated alcohol recycles, catalyst recirculation re-uses after using certain phase regeneration.
As preferably, described catalyzer is quaternary ammonium salt anionite-exchange resin.
As preferably, described tubular reactor is fixed-bed reactor or suspension reactor.
As preferably, reaction can be in vacuum, normal pressure or add to depress and carry out.
As preferably, the reaction times is depended on the residence time of reactor.
As preferably, in reaction, moisture should be in 0.1%.
As preferably, temperature of reaction, at 10～20 degree, lower than 5 degree, reacts too slow, exceedes 50 degree catalyst lifes too short.
The technical program has following advantage compared with other: catalyst recirculation is used, and can regenerate, and product separation does not simply need to destroy catalyzer and goes to separate again; Flexible operation, can be continuous, also can be intermittently, also can be semicontinuous, and can vacuum, normal pressure, pressurization, both can use fixed bed, also can use suspension system.
Adopt after said structure, beneficial effect of the present invention is: the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate of the present invention, have synthetic simple, mild condition, side reaction is few, and catalyst recirculation is used, need not destroy, and can regenerate, greatly simplify sepn process, be convenient to the advantages such as serialization production.
[brief description of the drawings]
Accompanying drawing described herein is to be used to provide a further understanding of the present invention, forms the application's a part, but do not form inappropriate limitation of the present invention, in the accompanying drawings:
Fig. 1 is a concrete structural representation of implementing of invention.
[embodiment]
Utilize accompanying drawing below, describe the present invention in detail by specific embodiment, illustrative examples wherein and explanation are only used for explaining the present invention, but not as a limitation of the invention.
The preparation method of a kind of synthetic 3-ethoxyl ethyl propionate described in this embodiment, its preparation method is as follows:
It comprises dehydrated alcohol and ethyl propenoate, and this dehydrated alcohol and ethyl propenoate obtain 3-ethoxyl ethyl propionate by the addition of tubular reactor under catalyzer; The mol ratio of described dehydrated alcohol and ethyl propenoate is 3: 1～100: 1, and catalyzer accounts for the ethyl propenoate of weight ratio 0.1%～20%; Described catalyzer is anionite-exchange resin;
Its reaction preparation process is as follows:
(1), use fixed bed system, preferably tubular type or tower reactor, catalyzer is fixed on the inside;
(2), first use dehydrated alcohol cleaning catalyst, and then with nitrogen purging, then use deionized water wash, and then with nitrogen purging, use afterwards 2～10% alkali lye processing, after handling, wash with water, then fill nitrogen;
(3), then wash filling under nitrogen with fresh ethanol or the mixture of ethanol and ethyl propenoate, then filling under nitrogen by washing with alcohol, until the moisture of the ethanol after the cleaning of system the inside is not more than the moisture in raw material dehydrated alcohol;
(4), the activity of successive reaction rear catalyst can decline gradually, when unreacted acrylate in mixture exceedes 1%, considers catalyst regeneration.
(5), moisture can affect reaction, should be controlled in 0.01～0.5%;
(6), temperature of reaction is between-5～35 degree;
(11), reaction is homogeneous phase substantially, except catalyzer is solid, reaction is catalyst fixed bed or material and catalyzer are uniformly mixed by one the material that mixes, can successive reaction, also can be semicontinuous, also can batch carry out;
(12), product 3-ethoxyl ethyl propionate from the feed separation of having reacted out, excessive dehydrated alcohol recycles, catalyst recirculation re-uses after using certain phase regeneration.
As preferably, described catalyzer is quaternary ammonium salt anionite-exchange resin.
As preferably, described tubular reactor is fixed-bed reactor or suspension reactor.
As preferably, reaction can be in vacuum, normal pressure or add to depress and carry out.
As preferably, the reaction times is depended on the residence time of reactor.
As preferably, in reaction, moisture should be in 0.1%.
As preferably, temperature of reaction, at 10～20 degree, lower than 5 degree, reacts too slow, exceedes 50 degree catalyst lifes too short.
In Fig. 1, fixed-bed reactor for the invention process example, also have thinning ratio (volumetric flow rate per hour is divided by reactor volume) to investigate the impact of fixed bed catalyst life-span and temperature by the ethylacrylate concentration changing in charging, when exceeding 1%, ethylacrylate concentration in outflow product just illustrates that catalyzer has arrived use terminal, need regeneration, if catalyst life economy in 50 hours cannot be accepted, following example shows, temperature is lower than 35 degree, catalyst life was higher than 50 hours, temperature is higher than 35 degree, catalyst life was lower than 50 hours.
Specific embodiment 1: 2.5 centimetres of radiuses, the fixed-bed reactor the inside that height is 75 centimetres, catalyzer is fixed on the inside, first use dehydrated alcohol cleaning catalyst, and then with nitrogen purging, then use deionized water wash, and then with nitrogen purging, use afterwards 2～10% alkali lye processing, after handling, wash with water, then fill nitrogen, then wash filling under nitrogen with fresh ethanol or the mixture of ethanol and ethyl propenoate, then filling under nitrogen by washing with alcohol, until the moisture of the ethanol after the cleaning of system the inside is not more than 0.1%, be 85:15 at material-compound tank by the mass ratio of dehydrated alcohol and ethyl propenoate, catalyzer is about 15% of ethyl propenoate, be cooled to temperature between 9-13 degree, pass into fixed-bed reactor by 2.1 thinning ratio, the temperature of reactor is controlled at 26 ± 2 degree, the material reflecting enters receiving tank, survey the content of the ethyl propenoate of the inside, the material of receiving tank is through rectifying tower rectifying, the EEP of purity 99% is collected as product, calculated yield, the ethyl propenoate that excessive ethanol and unreacted are complete and a small amount of EEP that carries secretly out return material-compound tank and add fresh dehydrated alcohol and ethyl propenoate furnishing 85:15, enter fixed bed circulating reaction.Continuously operation 100 hours, records discharging to the ethyl propenoate 0.5% in receiving tank, and the yield of the EEP collecting is 96%.
Specific embodiment 2: at the fixed-bed reactor face of above embodiment 1, fix catalyzer, clean and be dried as embodiment 1, be 85:15 at material-compound tank by the mass ratio of dehydrated alcohol and ethyl propenoate, catalyzer is about 15% of ethyl propenoate, be cooled to temperature between 19-20 degree, pass into fixed-bed reactor by 2.0 thinning ratio, the temperature of reactor is controlled at 28 ± 2 degree, the material reflecting enters receiving tank, survey the content of the ethyl propenoate of the inside, the material of receiving tank is through rectifying tower rectifying, the EEP of purity 99% is collected as product, calculated yield, the ethyl propenoate that excessive ethanol and unreacted are complete and a small amount of EEP that carries secretly out return material-compound tank and add fresh dehydrated alcohol and ethyl propenoate furnishing 85:15, enter fixed bed circulating reaction.Continuously operation 105 hours, records discharging to the ethyl propenoate 0.3% in receiving tank, and the yield of the EEP collecting is 98%.
Specific embodiment 3: at the fixed-bed reactor face of above embodiment 1, fix catalyzer, clean and be dried as embodiment 1, be 85:15 at material-compound tank by the mass ratio of dehydrated alcohol and ethyl propenoate, catalyzer is about 15% of ethyl propenoate, be cooled to temperature between 13-15 degree, pass into fixed-bed reactor by 2.0 thinning ratio, the temperature of reactor is controlled at 28 ± 2 degree, the material reflecting enters receiving tank, survey the content of the ethyl propenoate of the inside, the material of receiving tank is through rectifying tower rectifying, the EEP of purity 99% is collected as product, calculated yield, the ethyl propenoate that excessive ethanol and unreacted are complete and a small amount of EEP that carries secretly out return material-compound tank and add fresh dehydrated alcohol and ethyl propenoate furnishing 85:15, enter fixed bed circulating reaction.Continuously operation 90 hours, records discharging to the ethyl propenoate 0.8% in receiving tank, and the yield of the EEP collecting is 94%.
Specific embodiment 4: at the fixed-bed reactor face of above embodiment mono-, fix catalyzer, clean and be dried as embodiment 1, be 90:10 at material-compound tank by the mass ratio of dehydrated alcohol and ethyl propenoate, catalyzer is about 15% of ethyl propenoate, be cooled to temperature at 21 degree, pass into fixed-bed reactor by 2.0 thinning ratio, the temperature of reactor is controlled at 29 ± 2 degree, the material reflecting enters receiving tank, survey the content of the ethyl propenoate of the inside, the material of receiving tank is through rectifying tower rectifying, the EEP of purity 99% is collected as product, calculated yield, the ethyl propenoate that excessive ethanol and unreacted are complete and a small amount of EEP that carries secretly out return material-compound tank and add fresh dehydrated alcohol and ethyl propenoate furnishing 90:10, enter fixed bed circulating reaction.Continuously operation 98 hours, records discharging to the ethyl propenoate 0.4% in receiving tank, and the yield of the EEP collecting is 96%.
Specific embodiment 5-specific embodiment 17, its preparation method is with specific embodiment 1, and each index that different from specific embodiment 1 is is with reference to different, as following table:
Specific embodiment 18 and specific embodiment 19, have electric mixing device at one, thermometer, and reflux condensing tube 2 liters of four-hole boiling flasks in, add catalyzer, the processing of catalyzer is as specific embodiment 1.
Specific embodiment 18: add 1500 grams altogether of dehydrated alcohol and ethyl propenoates by quality 3:1 2 liters of four-hole boiling flask the insides, controlling temperature spends in 30 degree ± 2, add by ethyl propenoate 5% catalyzer of handling well, open stirring, rotating speed does not turn higher than 120, make catalyzer suspended dispersed even, react after 4 hours, stop stirring, elimination catalyzer, the ethyl propenoate content recording in filtrate is 0.5%, filtrate is adding the tower reactor of rectifying tower, heat up, between 74-165 degree, the front-end volatiles of ethanol and ethyl propenoate and a small amount of 3-ethoxyl ethyl propionate are sloughed in slow rectifying, collect 99% product, yield 88%.
Specific embodiment 19: the front-end volatiles that add dehydrated alcohol and ethyl propenoate and embodiment 19 in 2 liters of four-hole boiling flasks the inside altogether 1500 grams make dehydrated alcohol: ethyl propenoate, controlling temperature spends in 30 degree ± 2, add the catalyzer of embodiment 18, open stirring, rotating speed does not turn higher than 120, make catalyzer suspended dispersed even, react after 4 hours, stop stirring, elimination catalyzer, the ethyl propenoate content recording in filtrate is 0.5%, filtrate is adding the tower reactor of rectifying tower, heat up, between 74-165 degree, the front-end volatiles of ethanol and ethyl propenoate and a small amount of 3-ethoxyl ethyl propionate are sloughed in slow rectifying, collect 99% product, yield 98%., catalyzer is reacted to terminal content and more than 1% will regenerates being recycled to ethyl propenoate.
The technical program has following advantage compared with other: catalyst recirculation is used, and can regenerate, and product separation does not simply need to destroy catalyzer and goes to separate again; Flexible operation, can be continuous, also can be intermittently, also can be semicontinuous, and can vacuum, normal pressure, pressurization, both can use fixed bed, also can use suspension system.
The preparation method of a kind of synthetic 3-ethoxyl ethyl propionate of the present invention, has and synthesizes simply, mild condition, and side reaction is few, and catalyst recirculation is used, and need not destroy, and can regenerate, and has greatly simplified sepn process, is convenient to the advantages such as serialization production.
The above is only preferred embodiments of the present invention, and the equivalence of doing according to structure, feature and principle described in patent claim of the present invention therefore all changes or modifies, and is included in patent claim of the present invention.
Claims (7)
1. a preparation method for synthetic 3-ethoxyl ethyl propionate, its preparation method is as follows:
It comprises dehydrated alcohol and ethyl propenoate, and this dehydrated alcohol and ethyl propenoate obtain 3-ethoxyl ethyl propionate by the addition of tubular reactor under catalyzer; It is characterized in that: the mol ratio of described dehydrated alcohol and ethyl propenoate is 3: 1～100: 1, and catalyzer accounts for the ethyl propenoate of weight ratio 0.1%～20%; Described catalyzer is anionite-exchange resin;
Its reaction preparation process is as follows:
(1), use fixed bed system, preferably tubular type or tower reactor, catalyzer is fixed on the inside;
(2), first use dehydrated alcohol cleaning catalyst, and then with nitrogen purging, then use deionized water wash, and then with nitrogen purging, use afterwards 2～10% alkali lye processing, after handling, wash with water, then fill nitrogen;
(3), then wash filling under nitrogen with fresh ethanol or the mixture of ethanol and ethyl propenoate, then filling under nitrogen by washing with alcohol, until the moisture of the ethanol after the cleaning of system the inside is not more than the moisture in raw material dehydrated alcohol;
(4), the activity of successive reaction rear catalyst can decline gradually, when unreacted acrylate in mixture exceedes 1%, considers catalyst regeneration.
(5), moisture can affect reaction, should be controlled in 0.01～0.5%;
(6), temperature of reaction is between-5～35 degree;
(7), reaction is homogeneous phase substantially, except catalyzer is solid, reaction is catalyst fixed bed or material and catalyzer are uniformly mixed by one the material that mixes, can successive reaction, also can be semicontinuous, also can batch carry out;
(8), product 3-ethoxyl ethyl propionate from the feed separation of having reacted out, excessive dehydrated alcohol recycles, catalyst recirculation re-uses after using certain phase regeneration.
2. the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate according to claim 1, is characterized in that: described catalyzer is quaternary ammonium salt anionite-exchange resin.
3. the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate according to claim 1, is characterized in that: described tubular reactor is fixed-bed reactor or suspension reactor.
4. the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate according to claim 1, is characterized in that: reaction can be in vacuum, normal pressure or add to depress and carry out.
5. the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate according to claim 1, is characterized in that: the reaction times is depended on the residence time of reactor.
6. the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate according to claim 1, is characterized in that: in reaction, moisture should be in 0.1%.
7. the preparation method of a kind of synthetic 3-ethoxyl ethyl propionate according to claim 1, is characterized in that: temperature of reaction, at 10～20 degree, lower than 5 degree, reacts too slow, exceedes 50 degree catalyst lifes too short.
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| CN201410235205.8A CN104016861A (en) | 2014-05-30 | 2014-05-30 | Preparation method for synthesis of ethyl 3-ethoxypropionate |
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| CN201410235205.8A CN104016861A (en) | 2014-05-30 | 2014-05-30 | Preparation method for synthesis of ethyl 3-ethoxypropionate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037151A (en) * | 2015-05-29 | 2015-11-11 | 南京工业大学 | Preparation method of 3-alkoxy alkyl propionate |
| CN107010772A (en) * | 2017-05-27 | 2017-08-04 | 南京工业大学 | Resource utilization and purification treatment method for wastewater containing ethoxy sodium propionate |
| CN111004123A (en) * | 2019-12-24 | 2020-04-14 | 深圳市普利凯新材料股份有限公司 | Preparation method of ethyl 3-ethoxypropionate |
| CN111018707A (en) * | 2019-12-19 | 2020-04-17 | 深圳市普利凯新材料股份有限公司 | Preparation method of methyl 3-methoxypropionate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2658070A (en) * | 1952-02-01 | 1953-11-03 | Rohm & Haas | Carboalkoxyethylation reactions in presence of certain anion-exchange resins |
| EP0254291A2 (en) * | 1986-07-22 | 1988-01-27 | Union Carbide Corporation | Catalytic process for production of alkoxylated esters |
-
2014
- 2014-05-30 CN CN201410235205.8A patent/CN104016861A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2658070A (en) * | 1952-02-01 | 1953-11-03 | Rohm & Haas | Carboalkoxyethylation reactions in presence of certain anion-exchange resins |
| EP0254291A2 (en) * | 1986-07-22 | 1988-01-27 | Union Carbide Corporation | Catalytic process for production of alkoxylated esters |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037151A (en) * | 2015-05-29 | 2015-11-11 | 南京工业大学 | Preparation method of 3-alkoxy alkyl propionate |
| CN107010772A (en) * | 2017-05-27 | 2017-08-04 | 南京工业大学 | Resource utilization and purification treatment method for wastewater containing ethoxy sodium propionate |
| CN107010772B (en) * | 2017-05-27 | 2020-04-07 | 南京工业大学 | Resource utilization and purification treatment method for wastewater containing ethoxy sodium propionate |
| CN111018707A (en) * | 2019-12-19 | 2020-04-17 | 深圳市普利凯新材料股份有限公司 | Preparation method of methyl 3-methoxypropionate |
| CN111004123A (en) * | 2019-12-24 | 2020-04-14 | 深圳市普利凯新材料股份有限公司 | Preparation method of ethyl 3-ethoxypropionate |
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