CN104496836B - A kind of industrial method removing N, 2,3-trimethyl-2-butanamide mother liquor impurity - Google Patents
A kind of industrial method removing N, 2,3-trimethyl-2-butanamide mother liquor impurity Download PDFInfo
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Abstract
A kind of industrial method removing N, 2,3-trimethyl-2-butanamide mother liquor impurity of disclosure, comprises the following steps: (1) by mother solution when negative pressure 0.098MPa 70～85 DEG C distill out residual solvent；(2) residue mother solution is warming up under negative pressure 0.098MPa 90～100 DEG C and distills out 2,3-dimethyl-2-isopropyl butyronitrile；(3) fixing phase silica gel column chromatography is used to remove 2,3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramides in residue mother solution, detect after 1 column volume of eluting, collect eluent, obtain N after drying, 2,3-trimethyl-2-butanamide.Method provided by the invention can remove N, impurity in 2,3-trimethyl-2-butanamide mother solutions so that originally cannot be continuing with and as the N of waste liquid, 2,3-trimethyl-2-butanamide mother solution is re-used, and improves N, and 2, the yield of 3-trimethyl-2-butanamide, and isolated 2,3-dimethyl-2-isopropyl butyronitrile still can put into commercial production as intermediate again, have economy and environment protection significance concurrently.
Description
Technical field
The present invention relates to synthesis coolant agent production technical field, a kind of method being specially industrial removal WS-23 mother liquor impurity.
Background technology
Synthesis coolant agent WS-23 chemical name N, 2,3-trimethyl-2-butanamide, in its synthetic route 2,3-dimethyl-2-isopropyl butyronitrile (DIPPN) is the intermediate of most critical, and under polyphosphoric acids (PPA) catalysis, DIPPN synthesizes synthesis coolant agent WS-23 with dimethyl carbonate (DMC) through pyroreaction.Reason due to reaction yield and side reaction, containing DIPPN and 2 remained in the WS-23 mother solution synthesized, other impurity such as 3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramides, adopt the method for crystallization will synthesize coolant agent WS-23 separating-purifying out in commercial production.But due to after repeatedly crystallization, DIPPN and 2 in mother solution, the impurity enriched such as 3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramides, cause that mother solution cannot continue crystallization.Possibly together with substantial amounts of synthesis coolant agent WS-23 in above-mentioned mother solution, simple waste treatment also can produce a large amount of waste liquid while of not only reducing the yield of WS-23 and bring harm to environment.
But, due to the special physics of impurity and chemical property in synthesis coolant agent WS-23 mother solution (with synthesis coolant agent WS-23 boiling point close to etc.), simple industrial processing method, for instance distillation, rectification, crystallization, recrystallization etc. cannot remove it.Therefore, effective method is found to remove the impurity in synthesis coolant agent WS-23 mother solution, improving the yield of synthesis coolant agent WS-23, the generation reducing waste liquid is also one of the primary study problem in synthesis coolant agent WS-23 commercial production, the present invention is accomplished especially power and starting point place.
Summary of the invention
Technical problem solved by the invention is in that a kind of method providing industrial removal WS-23 mother liquor impurity, to solve the problem in above-mentioned background technology.
Technical problem solved by the invention realizes by the following technical solutions: a kind of industrial method removing N, 2,3-trimethyl-2-butanamide mother liquor impurity, comprises the following steps:
(1) by mother solution when negative pressure 0.098MPa 70～85 DEG C distill out residual solvent；
(2) residue mother solution is warming up under negative pressure 0.098MPa 90～100 DEG C and distills out 2,3-dimethyl-2-isopropyl butyronitrile (DIPPN)；
(3) fixing phase silica gel column chromatography is used to remove 2,3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramides in residue mother solution, detect after 1 column volume of eluting, collect eluent, obtain N after drying, 2,3-trimethyl-2-butanamide.
Fixing in described step (3) is 100,200,300,400 order purification on normal-phase silica gel mutually, mobile phase solvent is any two kinds of mixing in petroleum ether, dichloromethane, chloroform, ethyl acetate, acetone, ethanol, methanol, and two kinds of mobile phase solvent weight proportions are 1:1～9:1.
Compared with disclosed technology, there is advantages below in the present invention: method provided by the invention can remove N, and 2, impurity in 3-trimethyl-2-butanamide mother solution, make originally cannot be continuing with and WS-23 mother solution as waste liquid is re-used, improve N, the yield of 2,3-trimethyl-2-butanamide, and isolated 2,3-dimethyl-2-isopropyl butyronitrile still can put into commercial production as intermediate again, has economy and environment protection significance concurrently.
Accompanying drawing explanation
Fig. 1 is the raw material mother solution gas chromatogram of embodiments of the invention 1.
Fig. 2 is N, the 2,3-trimethyl-2-butanamide gas chromatogram obtained after the process of embodiments of the invention 1.
Fig. 3 is the isolated 2,3-dimethyl-2-isopropyl butyronitrile gas chromatogram of embodiments of the invention 1.
Fig. 4 is the raw material mother solution gas chromatogram of embodiments of the invention 2.
Fig. 5 is N, the 2,3-trimethyl-2-butanamide gas chromatogram obtained after the process of embodiments of the invention 2.
Fig. 6 is the isolated 2,3-dimethyl-2-isopropyl butyronitrile gas chromatogram of embodiments of the invention 2.
Detailed description of the invention
It is easy to understand with effect to make the technological means of the present invention, creation characteristic, workflow, using method reach purpose, below in conjunction with the embodiment of the present invention, technical scheme in the embodiment of the present invention is clearly and completely described, obviously, described embodiment is only a part of embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art obtain under not making creative work premise, broadly fall into the scope of protection of the invention.
A kind of industrial method removing N, 2,3-trimethyl-2-butanamide mother liquor impurity, comprises the following steps:
(1) by mother solution when negative pressure 0.098MPa 70～85 DEG C distill out residual solvent；
(2) residue mother solution is warming up under negative pressure 0.098MPa 90～100 DEG C and distills out 2,3-dimethyl-2-isopropyl butyronitrile (DIPPN)；
(3) fixing phase silica gel column chromatography is used to remove 2,3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramides in residue mother solution, detect after 1 column volume of eluting, collect eluent, obtain N after drying, 2,3-trimethyl-2-butanamide.
Fixing in described step (3) is 100,200,300,400 order purification on normal-phase silica gel mutually, mobile phase solvent is any two kinds of mixing in petroleum ether, dichloromethane, chloroform, ethyl acetate, acetone, ethanol, methanol, and two kinds of mobile phase solvent weight proportions are 1:1～9:1.
Embodiment 1
WS-23 mother solution 124kg, WS-23 content is 60.34%, and DIPPN content is 10.06%, and residual solvent levels is 21.78%, 2, and 3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramide content are 5.4%.
Step (1), mother solution is heated under negative pressure 0.098MPa to 80 DEG C, distilling off solvent 19.63kg；
Step (2), residue mother solution is warming up to 95 DEG C under negative pressure 0.098MPa, distills out DIPPN10.54kg；
Chromatographic column is added after step (3), general's residue mother solution and the mixing of 100 order purification on normal-phase silica gel, fixing is 200 order purification on normal-phase silica gel mutually, mobile phase is petroleum ether: ethyl acetate=7: 3, detect after 1 column volume of eluting, collect eluent, obtain WS-2359.85kg after drying, the pure washed with methanol of chromatographic column.
Embodiment 2
WS-23 mother solution 98.7kg, WS-23 content is 56.82%, and DIPPN content is 35.26%, and residual solvent levels is 3.78%, 2, and 3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramide content are 3.24%.
Step (1), mother solution is heated under negative pressure 0.098MPa to 80 DEG C, distilling off solvent 2.63kg；
Step (2), residue mother solution is warming up to 95 DEG C under negative pressure 0.098MPa, distills out DIPPN33.80kg；
Chromatographic column is added after step (3), general's residue mother solution and the mixing of 100 order purification on normal-phase silica gel, fixing is 200 order purification on normal-phase silica gel mutually, mobile phase is petroleum ether: methanol=9: 1, detect after 1 column volume of eluting, collect eluent, obtain WS-2342.85kg after drying, the pure washed with methanol of chromatographic column.
Method provided by the invention can remove N, impurity in 2,3-trimethyl-2-butanamide mother solutions so that originally cannot be continuing with and as the N of waste liquid, 2,3-trimethyl-2-butanamide mother solution is re-used, and improves N, and 2, the yield of 3-trimethyl-2-butanamide, and isolated 2,3-dimethyl-2-isopropyl butyronitrile still can put into commercial production as intermediate again, have economy and environment protection significance concurrently.
The ultimate principle of the present invention, principal character and advantages of the present invention have more than been shown and described.Skilled person will appreciate that of the industry; the present invention is not restricted to the described embodiments; described in above-described embodiment and description is that principles of the invention is described; without departing from the spirit and scope of the present invention; the present invention also has various changes and modifications, and these changes and improvements both fall within the claimed scope of the invention.The claimed scope of the present invention is defined by appending claims and equivalent thereof.
Claims (1)
1. the industrial method removing a N, 2,3-trimethyl-2-butanamide mother liquor impurity, it is characterised in that: comprise the following steps:
(1) by mother solution when negative pressure 0.098MPa 70～85 DEG C distill out residual solvent；
(2) residue mother solution is warming up under negative pressure 0.098MPa 90～100 DEG C and distills out 2,3-dimethyl-2-isopropyl butyronitrile；
(3) fixing phase silica gel column chromatography is used to remove 2,3-dimethyl-2-isopropyl butanoic acid, 2,3-dimethyl-2-isopropyl butyramides in residue mother solution, detect after 1 column volume of eluting, collect eluent, obtain N after drying, 2,3-trimethyl-2-butanamide；
Fixing in described step (3) is 100,200,300,400 order purification on normal-phase silica gel mutually, mobile phase solvent is any two kinds of mixing in petroleum ether, dichloromethane, chloroform, ethyl acetate, acetone, ethanol, methanol, and two kinds of mobile phase solvent weight proportions are 1:1～9:1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6482983B1 (en) * | 2001-07-31 | 2002-11-19 | Millennium Specialty Chemicals | Process for obtaining N-monosubstituted amides |
| CN101591263A (en) * | 2009-07-07 | 2009-12-02 | 安徽丰乐香料有限责任公司 | The preparation method of N-ethyl-2-sec.-propyl-5-methylcyclohexane methane amide |
| CN102964268A (en) * | 2012-10-27 | 2013-03-13 | 安徽丰乐香料有限责任公司 | Synthesis method of menthyl amide cooling agent |
| CN103274959A (en) * | 2013-06-20 | 2013-09-04 | 安徽科技学院 | Synthetic method of cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide |
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2014
- 2014-11-27 CN CN201410709984.0A patent/CN104496836B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6482983B1 (en) * | 2001-07-31 | 2002-11-19 | Millennium Specialty Chemicals | Process for obtaining N-monosubstituted amides |
| CN101591263A (en) * | 2009-07-07 | 2009-12-02 | 安徽丰乐香料有限责任公司 | The preparation method of N-ethyl-2-sec.-propyl-5-methylcyclohexane methane amide |
| CN102964268A (en) * | 2012-10-27 | 2013-03-13 | 安徽丰乐香料有限责任公司 | Synthesis method of menthyl amide cooling agent |
| CN103274959A (en) * | 2013-06-20 | 2013-09-04 | 安徽科技学院 | Synthetic method of cooling agent N-, 2, 3-trimethyl-2-isopropyl butyrylamide |
Non-Patent Citations (1)
| Title |
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| 新型凉味剂N,2,3-三甲基-2-异丙基丁酰胺(WS-23)的合成;李家玉等;《香料香精化妆品》;20071230(第06期);第18页第1.3.2节、第17页图2 * |
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