CN102260185A - Synthetic method of N-ethyl-2,2-diisopropyl butyramide - Google Patents
Synthetic method of N-ethyl-2,2-diisopropyl butyramide Download PDFInfo
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- CN102260185A CN102260185A CN2011101570757A CN201110157075A CN102260185A CN 102260185 A CN102260185 A CN 102260185A CN 2011101570757 A CN2011101570757 A CN 2011101570757A CN 201110157075 A CN201110157075 A CN 201110157075A CN 102260185 A CN102260185 A CN 102260185A
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Abstract
The invention relates to a synthetic method of N-ethyl-2,2-diisopropyl butyramide. Raw materials comprise diisopropyl butyronitrile and ethyl ester compounds and a catalyst is polyphosphoric acid. The reaction raw materials are all liquids; the reaction is the homogeneous reaction of liquid state and is easy to control with high selectivity but few by-products; the purification of a product is simple and the product whose purity is greater than 99% can be directly obtained by high vacuum distillation; and a few unreacted raw materials can be recycled for use by separation.
Description
Technical field
The present invention relates to a kind of N-ethyl-2, the synthetic method of 2-di-isopropyl butyramide.
Background technology
Common method by nitrile prepared in reaction N-alkyl substituted amide is Ritter reaction (Ritter), under the catalysis of strong acid, the addition hydrolysis reaction can take place in alkene and nitrile, the course of reaction is: alkene at first generates carbonium ion, generate active intermediate with nitrile again, water carries out nucleophilic addition(Adn) generation acid amides to it then.Reaction catalyzer commonly used is a sulfuric acid, formic acid, trifluoromethanesulfanhydride anhydride and some Lewis acids (Lewis).Ritter reaction is not only applicable to alkene, all compound such as alcohol that under acid catalysis, can form carbonium ion, and above-mentioned reaction all can take place in halohydrocarbon, beta-unsaturated carbonyl compounds etc.The complex compound of some transition metal complex such as cobalt and iron also can catalysis allyl alcohol and benzylalcohol and nitrile generation acid amides in addition.
Existing preparation N-ethyl-2,2-di-isopropyl butyramide, the CAS of this compound number is 51115-70-9, react with di-isopropyl butyronitrile and ethene, the selectivity of reaction is relatively poor, and by product is many, brings a lot of difficulties for follow-up separation, cause yield lower, and ethene is gas, and the di-isopropyl butyronitrile is a liquid, and reaction relates to the gas-liquid two-phase reaction, than higher, reaction process also is not easy control to the requirement of conversion unit.
Summary of the invention
The purpose of this invention is to provide a kind of N-ethyl-2, the synthetic method of 2-di-isopropyl butyramide, the raw material of reaction are di-isopropyl butyronitrile and ethyl ester compound, and catalyzer is a polyphosphoric acid, ethyl ester compound is to comprise diethyl carbonate (ethyl-carbonate), ethyl sulfate C
4H
10O
4S, triethyl phosphate TEP etc.The reaction temperature range be 80 spend to 180 the degree, preferred range be 110 spend to 150 the degree.Reaction time range is 4 to 16 hours, preferably 8 to 10 hours.The quality of di-isopropyl butyronitrile and ethyl ester compound is that 1:0.6 is to 1:3 than scope.The quality of di-isopropyl butyronitrile and polyphosphoric acid is that 1:1.5 is to 1:10 than scope.
The present invention is that (Polyphosphoric acid, abbreviation PPA claims Tripyrophosphoric acid, polyphosphoric acid again at polyphosphoric acid with di-isopropyl butyronitrile and ethyl ester compound.) catalysis under react, generate N-ethyl-2,2-di-isopropyl butyramide, reaction raw materials all are liquid, reaction is liquid homogeneous reaction, reaction is easy to control, and selectivity is very high, and by product seldom, the purification of product is fairly simple, can directly obtain purity greater than 99% product by high vacuum rectification, a spot of unreacting material can recycle by separating.Reaction formula is as follows:
。
Description of drawings
Fig. 1 is a N-ethyl-2,2-di-isopropyl butyramide stratographic analysis figure.
Embodiment
Embodiment 1:
Drop into 150 gram di-isopropyl butyronitrile in the 2000ml there-necked flask, 120 gram diethyl carbonates and 400 grams, 115% polyphosphoric acid, start mechanical stirring, under the reflux condition, control reaction temperature is at 125-135 ℃, reflux stirred about 10 hours, reaction solution is cooled to about 30 ℃ afterwards, slowly add an amount of water, decompose the intact polyphosphoric acid of unreacted, add 500 gram toluene extraction products again, the toluene phase is collected in the profit layering, wash toluene twice mutually with 200 grams, 5% aqueous sodium carbonate, with 100 gram washings twice, unreacted di-isopropyl butyronitrile content is 36% in the reaction product again, and product content is 60%, toluene is reclaimed in underpressure distillation then, and high vacuum rectification obtains 99% finished product, 110 grams again.
Embodiment 2
Drop into 150 gram di-isopropyl butyronitrile in the 2000ml there-necked flask, 280 gram triethyl phosphates and 400 grams, 115% polyphosphoric acid, start mechanical stirring, under the reflux condition, control reaction temperature is at 140-150 ℃, reflux stirred about 9 hours, reaction solution is cooled to about 30 ℃ afterwards, slowly add an amount of water, decompose the intact polyphosphoric acid of unreacted, add 500 gram toluene extraction products again, the toluene phase is collected in the profit layering, wash toluene twice mutually with 200 grams, 5% aqueous sodium carbonate, with 100 gram washings twice, unreacted di-isopropyl butyronitrile content is 24% in the reaction product again, and product content is 72%, toluene is reclaimed in underpressure distillation then, and high vacuum rectification obtains 99% finished product, 130 grams again.
Embodiment 3
Drop into 150 gram di-isopropyl butyronitrile in the 2000ml there-necked flask, 250 gram triethyl phosphates and 900 grams, 115% polyphosphoric acid, start mechanical stirring, under the reflux condition, control reaction temperature is at 135-140 ℃, reflux stirred about 8 hours, reaction solution is cooled to about 30 ℃ afterwards, slowly add an amount of water, decompose the intact polyphosphoric acid of unreacted, add 500 gram toluene extraction products again, the toluene phase is collected in the profit layering, wash toluene twice mutually with 200 grams, 5% aqueous sodium carbonate, with 100 gram washings twice, unreacted di-isopropyl butyronitrile content is 13% in the reaction product again, and product content is 80%, toluene is reclaimed in underpressure distillation then, and high vacuum rectification obtains 99% finished product, 145 grams again.
N-ethyl-2 as shown in Figure 1,2-di-isopropyl butyramide stratographic analysis figure, chromatographiccondition:
Below be the area percentage laboratory report:
According to gas chromatogram, the main ingredient retention time:
。
Reaction raw materials of the present invention all is a liquid, reaction is liquid homogeneous reaction, reaction is easy to control, selectivity is very high, by product seldom, the purification of product is fairly simple, can directly obtain purity greater than 99% product by high vacuum rectification, a spot of unreacting material can recycle by separating.
Claims (7)
1. N-ethyl-2, the synthetic method of 2-di-isopropyl butyramide is characterized in that, and raw material is di-isopropyl butyronitrile and ethyl ester compound, and catalyzer is a polyphosphoric acid.
2. synthetic method according to claim 1 is characterized in that, described ethyl ester compound is diethyl carbonate, ethyl sulfate or triethyl phosphate.
3. synthetic method according to claim 1 is characterized in that, the temperature range of reaction be 80 spend to 180 the degree.
4. synthetic method according to claim 3 is characterized in that, the temperature range of reaction be 110 spend to 150 the degree.
5. synthetic method according to claim 1 is characterized in that, reaction time range is 4 to 16 hours.
6. synthetic method according to claim 5 is characterized in that, reaction time range is 8 to 10 hours.
7. synthetic method according to claim 1 is characterized in that, the quality of di-isopropyl butyronitrile and ethyl ester compound is that 1:0.6 is to 1:3 than scope; The quality of di-isopropyl butyronitrile and polyphosphoric acid is that 1:1.5 is to 1:10 than scope.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101570757A CN102260185A (en) | 2011-06-13 | 2011-06-13 | Synthetic method of N-ethyl-2,2-diisopropyl butyramide |
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|---|---|---|---|
| CN2011101570757A CN102260185A (en) | 2011-06-13 | 2011-06-13 | Synthetic method of N-ethyl-2,2-diisopropyl butyramide |
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| CN102260185A true CN102260185A (en) | 2011-11-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2011101570757A Pending CN102260185A (en) | 2011-06-13 | 2011-06-13 | Synthetic method of N-ethyl-2,2-diisopropyl butyramide |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1184465A (en) * | 1995-05-19 | 1998-06-10 | 巴斯福股份公司 | Carboxylic acid derivative preparation process |
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2011
- 2011-06-13 CN CN2011101570757A patent/CN102260185A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1184465A (en) * | 1995-05-19 | 1998-06-10 | 巴斯福股份公司 | Carboxylic acid derivative preparation process |
Non-Patent Citations (1)
| Title |
|---|
| MIKHAIL Y. LEBEDEV ET AL.: "Lower primary alkanols and their esters in a Ritter-type reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides", 《TETRAHEDRON LETTERS》 * |
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Inventor after: Zhou Junxue Inventor after: Chen Qing Inventor before: Zhou Junxue |
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Application publication date: 20111130 |