CN110790679B - Preparation method of 3-bromopropionitrile - Google Patents
Preparation method of 3-bromopropionitrile Download PDFInfo
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- CN110790679B CN110790679B CN201911020496.8A CN201911020496A CN110790679B CN 110790679 B CN110790679 B CN 110790679B CN 201911020496 A CN201911020496 A CN 201911020496A CN 110790679 B CN110790679 B CN 110790679B
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- bromopropionitrile
- acrylonitrile
- acetonitrile
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- CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 18
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 14
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000007259 addition reaction Methods 0.000 claims abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- CPOJJARBCZIKQQ-UHFFFAOYSA-N 3-trimethylsilyloxypropanenitrile Chemical compound C[Si](C)(C)OCCC#N CPOJJARBCZIKQQ-UHFFFAOYSA-N 0.000 description 1
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229960002656 didanosine Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- ZPATUOFYXSBHMN-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [H+].[H+].[H+].[Br-].[Br-].[Br-].C1=CC=NC=C1 ZPATUOFYXSBHMN-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 3-bromopropionitrile, which comprises the following steps: taking acrylonitrile as a raw material, carrying out intermolecular addition reaction on trimethyl bromosilane, and then distilling and purifying to obtain the high-purity 3-bromopropionitrile. According to the method, cheap acrylonitrile is used as a raw material, and the 3-bromopropionitrile with high purity is obtained through the intermolecular addition reaction of trimethyl bromosilane and finally distillation and purification, wherein the raw material is cheap and easy to obtain, is suitable for commercial production, and is environment-friendly, less in three wastes and high in yield.
Description
Technical Field
The invention relates to a preparation method, in particular to a preparation method of 3-bromopropionitrile.
Background
3-bromopropionitrile is an important medical intermediate and fine chemical raw material. It is the starting material for producing the antiviral drug didanosine and is also used as the production material of spermidine. The conventional preparation method comprises the steps of adding beta-hydroxypropionitrile and phosphorus tribromide into benzene to react, distilling off the solvent benzene after the reaction is completed, and distilling the reaction product under reduced pressure to obtain a pure product of 3-bromopropionitrile, as shown in the following (Journal of the Chemical Society, perkin Transactions2: physical Organic Chemistry (1972-1999); 1977; p.1914-1919).
The main defects of the process are as follows: phosphorus tribromide is expensive, and a large amount of acidic wastewater is generated in the treatment process; the solvent benzene is a kind of solvent with limited use and has strong carcinogenic risk.
Bulletin de la Societe Chimique de France (1920), 27,901 reported the reaction of acrylonitrile as a starting material with hydrogen bromide to give 3-bromopropionitrile. The reaction has the advantages of large amount of hydrogen bromide gas, strong corrosion to equipment, low yield and large amount of by-products.
Org, biomol, chem, 2015,13,2001 report 3-trimethylsiloxypropionitrile as a starting material, which was reacted with phosphorus trichloride followed by pyridine tribromide to give 3-bromopropionitrile. The post-treatment of the process is complex and generates a large amount of wastewater.
Disclosure of Invention
The invention aims to provide a preparation method of 3-bromopropionitrile, which solves the problems of high cost of raw materials, low yield, more three wastes and environmental unfriendliness in the prior art.
The invention is realized by the following technical scheme:
a preparation method of 3-bromopropionitrile comprises the following steps: taking acrylonitrile as a raw material, carrying out intermolecular addition reaction on trimethyl bromosilane, and then distilling and purifying to obtain the high-purity 3-bromopropionitrile.
The specific synthetic route of the invention is as follows:
according to the invention, cheap acrylonitrile is used as a raw material, and high-purity 3-bromopropionitrile is obtained through an intermolecular addition reaction of trimethyl bromosilane and final distillation and purification. The method has the advantages of cheap and easily-obtained raw materials, less wastewater generated by post-treatment, higher yield and lower cost, and is more suitable for commercial production; compared with hydrogen bromide and boron tribromide, TMSBr has small corrosion to equipment and only generates a small amount of solid waste; the distilled reaction solvent is collected and can be recycled through simple drying post-treatment; the invention produces less three wastes and is environment-friendly.
The preparation method of the 3-bromopropionitrile comprises the following specific steps: dissolving trimethyl bromosilane in an organic solvent, dropwise adding acrylonitrile at 0-40 ℃, dropwise adding deionized water, reacting at 0-40 ℃ until the raw materials disappear after dropwise adding, and filtering, concentrating and rectifying the reaction liquid to obtain the high-purity 3-bromopropionitrile. The reaction temperature in the preparation process is 0-40 ℃, and the optimal reaction temperature is selected to have less impurity content.
Preferably, the organic solvent is one of ethyl acetate, tetrahydrofuran, dichloromethane, toluene and acetonitrile.
Preferably, the organic solvent is acetonitrile. Acetonitrile gives the highest yield and is therefore the preferred solvent.
The preparation method of the 3-bromopropionitrile comprises the following specific steps: dissolving trimethyl bromosilane in acetonitrile, and stirring; under the protection of nitrogen, acrylonitrile is dripped into the mixture at the temperature of between 20 and 40 ℃; and (3) after the dropwise addition, controlling the reaction temperature to be 20-40 ℃, dropwise adding deionized water, reacting at 20-40 ℃ until the raw materials disappear after the dropwise addition, filtering the separated solid, concentrating the filtrate under reduced pressure, and rectifying by using a rectifying device to obtain the high-purity 3-bromopropionitrile. The invention takes acetonitrile as a solvent, optimizes the optimal reaction temperature and achieves the highest yield.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. according to the preparation method of the 3-bromopropionitrile, cheap acrylonitrile is used as a raw material, and the 3-bromopropionitrile with high purity is obtained through the intermolecular addition reaction of trimethyl bromosilane and finally distillation purification, wherein the raw material is cheap and easy to obtain, and is suitable for commercial production;
2. the preparation method of the 3-bromopropionitrile has simple post-treatment, basically does not generate wastewater, and can obtain a high-purity product only by simple quenching, filtering, concentrating and rectifying operations after the reaction;
3. the preparation method of 3-bromopropionitrile provided by the invention collects the distilled reaction solvent, can be recycled through simple drying post-treatment, and has high material utilization rate.
Drawings
The accompanying drawings, which are included to provide a further understanding of the embodiments of the invention and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the invention and together with the description serve to explain the principles of the invention. In the drawings:
FIG. 1 is a schematic diagram of the reaction of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to examples and accompanying drawings, and the exemplary embodiments and descriptions thereof are only used for explaining the present invention and are not meant to limit the present invention.
Example 1
The invention relates to a preparation method of 3-bromopropionitrile, which comprises the following specific steps: trimethylbromosilane (71.40kg, 653.60mol, 0.95eq) was dissolved in acetonitrile (15 Vol) and stirring was turned on; under the protection of nitrogen, acrylonitrile (25.40kg, 479.25mol, 1eq) is dropped at 20-40 ℃; after the dropwise addition, the reaction temperature is controlled to be 20-40 ℃, deionized water (10.60kg, 294.44mol and 2eq) is dropwise added, after the dropwise addition is finished, the reaction is carried out at 20-40 ℃ overnight until the raw materials basically disappear, the precipitated solid is filtered, the filtrate is decompressed and concentrated until no solvent flows out basically, a rectification device (75 +/-5 ℃,9-12 mmTorr) is used for rectification to obtain 45.45kg of colorless liquid, and the yield is 70.9 percent (the purity of the gas chromatography is more than 98 percent). H NMR (CDCl) 3 400 MHz). Delta.3.52-3.55 (t, 2H), 2.98-3.01 (t, 2H). The synthetic route of the invention is shown in figure 1.
Example 2
The invention relates to a preparation method of 3-bromopropionitrile, which comprises the following specific steps: trimethylbromosilane (71.40g, 0.66mol, 0.95eq) was dissolved in toluene (12 Vol) and stirring was turned on; under the protection of nitrogen, acrylonitrile (25.40g, 0.48mol, 1eq) is dropped at 20-40 ℃; controlling the reaction temperature to be 20-40 ℃ after the dropwise addition, dropwise adding deionized water (10.60g, 0.29mol, 2eq) at the temperature of 20-40 ℃, reacting overnight at the temperature of 20-40 ℃ until the raw materials basically disappear, filtering the precipitated solid, and concentrating the filtrate under reduced pressure to obtain the filtrateThe solvent-free solution was distilled with a distillation apparatus (75. + -. 5 ℃ C., 9-12 mmTorr) to give 38.0g with a yield of 59.7% (gas chromatography purity greater than 98%). HNMR (CDCl) 3 ,400MHz):δ3.52-3.55(t,2H),2.98-3.00.01(t,2H)。
Comparing example 1 with example 2, it is clear that the yield of acetonitrile as an organic solvent is higher than that of toluene, and acetonitrile is preferred as an organic solvent in the present invention.
Example 3
The invention relates to a preparation method of 3-bromopropionitrile, which comprises the following specific steps: trimethylbromosilane (71.40g, 0.66mol, 0.95eq) was dissolved in acetonitrile (15 Vol) and stirring was turned on. Under the protection of nitrogen, acrylonitrile (25.40g, 0.48mol, 1eq) is dropped at 0-20 ℃; after the dropwise addition, the reaction temperature is controlled to be 0-20 ℃, deionized water (10.60g, 0.29mol and 2eq) is dropwise added, after the dropwise addition is finished, the reaction is carried out at 10-20 ℃ overnight until the raw materials basically disappear, the precipitated solid is filtered, the filtrate is decompressed and concentrated until no solvent flows out basically, and the filtrate is rectified by a rectifying device (75 +/-5 ℃,9-12 mmTorr) to obtain 41.0g, and the yield is 64.2% (the purity of the gas chromatography is more than 98%). H NMR (CDCl) 3 ,400MHz):δ3.52-3.55(t,2H),2.98-3.01(t,2H)。
It is understood from the comparison of example 1 and example 3 that the yield varies at different reaction temperatures, and in the present invention, in the case of using acetonitrile as an organic solvent, the optimal reaction temperature range is preferred and the yield is optimal. The invention preferably selects the best reaction condition by combining the embodiment 1-the embodiment 3, and uses acetonitrile as the organic solvent under the condition that the proportion of each component is basically the same, the reaction temperature is 20-40 ℃, and the product yield reaches the highest.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are merely exemplary embodiments of the present invention, and are not intended to limit the scope of the present invention, and any modifications, equivalent substitutions, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (5)
1. A preparation method of 3-bromopropionitrile is characterized by comprising the following steps: taking acrylonitrile as a raw material, carrying out intermolecular addition reaction on trimethyl bromosilane, and then distilling and purifying to obtain the 3-bromopropionitrile.
2. The method for preparing 3-bromopropionitrile according to claim 1, characterized by comprising the following steps: dissolving trimethyl bromosilane in an organic solvent, dropwise adding acrylonitrile at 0-40 ℃, dropwise adding deionized water, reacting at 0-40 ℃ until the raw materials disappear after dropwise adding, and filtering, concentrating and rectifying the reaction liquid to obtain the 3-bromopropionitrile.
3. The method according to claim 2, wherein the organic solvent is one of ethyl acetate, tetrahydrofuran, dichloromethane, toluene and acetonitrile.
4. The method according to claim 3, wherein the organic solvent is acetonitrile.
5. The method for preparing 3-bromopropionitrile according to claim 4, characterized by comprising the following steps: dissolving trimethyl bromosilane in acetonitrile, and stirring; under the protection of nitrogen, acrylonitrile is dripped into the mixture at the temperature of between 20 and 40 ℃; and after the dripping is finished, controlling the reaction temperature to be 20-40 ℃, dripping deionized water, reacting at 20-40 ℃ until the raw materials disappear after the dripping is finished, filtering the precipitated solid, and rectifying the filtrate by using a rectifying device to obtain the 3-bromopropionitrile after the filtrate is subjected to reduced pressure concentration.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644476A (en) * | 1969-06-23 | 1972-02-22 | Halcon International Inc | Preparation of adiponitrile |
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- 2019-10-25 CN CN201911020496.8A patent/CN110790679B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644476A (en) * | 1969-06-23 | 1972-02-22 | Halcon International Inc | Preparation of adiponitrile |
Non-Patent Citations (2)
| Title |
|---|
| THE ADDITION OF TRIMETHYLSILYL IODIDE TO SOME a,B-UNSATURATED KETONES;R. D. Miller等;《Tetrahedron Letters》;19791231(第25期);第2305-2306页 * |
| Trimethylchlorosilane and Water. Convenient Reagents for the Regioselective Hydrochlorination of Olefins;Boudjouk, Philip等;《Synthetic Communications》;20060821;第26卷(第18期);第3479-3484页 * |
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