CN114292209A - Preparation method of valeronitrile - Google Patents
Preparation method of valeronitrile Download PDFInfo
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- CN114292209A CN114292209A CN202111598761.8A CN202111598761A CN114292209A CN 114292209 A CN114292209 A CN 114292209A CN 202111598761 A CN202111598761 A CN 202111598761A CN 114292209 A CN114292209 A CN 114292209A
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- valeronitrile
- sodium cyanide
- chlorobutane
- preparation
- reaction
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- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims abstract description 70
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 230000009471 action Effects 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000002699 waste material Substances 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 8
- 239000005708 Sodium hypochlorite Substances 0.000 abstract description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 4
- 230000009967 tasteless effect Effects 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 9
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229960000519 losartan potassium Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The application belongs to the technical field of chemical intermediates, and particularly relates to a preparation method of valeronitrile, which comprises the following steps: sodium cyanide and excessive 1-chlorobutane are used as raw materials and react under the action of a catalyst to generate valeronitrile. According to the method, sodium cyanide and 1-chlorobutane are used as raw materials to produce the valeronitrile, the cost of the raw materials is relatively low, the yield of the valeronitrile prepared by the method is high, and the purity of the product is high. Excessive 1-chlorobutane is adopted to react with sodium cyanide, so that the reaction of the sodium cyanide is promoted to be complete, the unreacted sodium cyanide does not need to be treated by excessive sodium hypochlorite after the reaction is finished, the generation of three wastes is reduced, and the method is environment-friendly. And because the waste liquid of sodium cyanide has relatively great potential safety hazard, the sodium cyanide meets acid and produces the cyanohydric acid, colorless tasteless but virulent, there is the safety problem easily, this application uses excessive 1-chlorobutane to cooperate with catalyst to impel the sodium cyanide reaction to be complete, reduces the potential safety hazard.
Description
Technical Field
The application belongs to the technical field of chemical intermediates, and particularly relates to a preparation method of valeronitrile.
Background
Valeronitrile is a key raw material for preparing a key intermediate imidazole aldehyde of losartan potassium which is a hypertension drug. The traditional preparation process is obtained by adopting 1-bromobutane and sodium cyanide as raw materials, but the 1-bromobutane has higher cost and is not beneficial to reducing the production cost.
In addition to the above methods, there are two methods for synthesizing valeronitrile; firstly, valeraldehyde and hydroxylamine hydrochloride are used as raw materials; the second method is to use n-butanol and tetrabutylammonium cyanide as raw materials. However, the two methods have some defects, and the valeraldehyde serving as the raw material in the first method is harsh in storage condition and easy to deteriorate due to improper storage; the starting material tetrabutylammonium cyanide in process two is expensive and difficult to obtain.
In view of the above, there is a need to develop a novel method for preparing valeronitrile, which uses cheap and easily available raw materials and can obtain high yield.
Disclosure of Invention
In order to solve the problems, the application discloses a preparation method of valeronitrile, the preparation method takes sodium cyanide and 1-chlorobutane as raw materials to produce the valeronitrile, the cost of the raw materials is relatively low, the yield of the valeronitrile prepared by the method is high, and the purity of the product is high.
The application provides a preparation method of valeronitrile, which adopts the following technical scheme:
a preparation method of valeronitrile, which comprises the following steps: sodium cyanide and excessive 1-chlorobutane are used as raw materials and react under the action of a catalyst to generate valeronitrile.
The reaction process is as follows:
according to the method, sodium cyanide and excessive 1-chlorobutane are adopted to react to prepare the valeronitrile, the raw material cost is low, the yield of the valeronitrile is high, and the purity of the valeronitrile is high. The excessive 1-chlorobutane can promote the reaction of sodium cyanide to be complete, and after the reaction is finished, the unreacted sodium cyanide does not need to be treated by excessive sodium hypochlorite, so that the generation of three wastes is reduced, and the method is environment-friendly.
Preferably, the molar ratio of sodium cyanide to 1-chlorobutane is 1:1.1 to 1.9.
Preferably, the molar ratio of sodium cyanide to 1-chlorobutane is 1: 1.5.
The inventor finds that the molar ratio of the sodium cyanide to the 1-chlorobutane is controlled to be 1:1.5, so that the forward reaction is facilitated, excessive unreacted sodium cyanide in the system is avoided, and excessive use of the 1-chlorobutane is avoided.
Preferably, the sodium cyanide is a sodium cyanide solution with a mass percent concentration of 30%.
The dropwise addition of sodium cyanide in the form of solution is beneficial to full reaction of sodium cyanide, post-treatment and environmental pollution reduction.
Preferably, the amount of the catalyst is 5-10% of the total mass of the 1-chlorobutane; the catalyst comprises tetrabutylammonium bromide.
Preferably, the catalyst also comprises triethylamine, and the mass ratio of the tetrabutylammonium bromide to the triethylamine is 1: 0.3-0.5.
The inventor finds that tetrabutylammonium bromide and triethylamine are used as combined catalysts to obtain higher yield and product purity.
Preferably, a cocatalyst is further added in the reaction, the cocatalyst is isopropanol, and the mass ratio of tetrabutylammonium bromide to isopropanol is 1: 3-5. .
The inventors found in experiments that a little more isopropanol was added to the catalyst, which further promoted the improvement of yield and product purity.
Preferably, the preparation method specifically comprises the following steps: adding sodium cyanide, 1-chlorobutane and a catalyst into a reaction kettle, heating to the reaction temperature under stirring, reacting for 3-4 h, standing for layering, and then distilling an organic layer to obtain valeronitrile.
The inventor finds that the raw material proportion, the catalyst and the cocatalyst can ensure that the reaction of sodium cyanide is basically complete within about 3-4 h, and can avoid excessive residual sodium cyanide in a reaction kettle from being unfavorable for aftertreatment and bringing about potential safety hazards.
Preferably, the reaction temperature is 20 to 100 ℃, preferably, the reaction temperature is 50 to 90 ℃.
The inventors found that the reaction is facilitated by controlling the reaction temperature to 50 to 90 ℃.
Preferably, the organic layer distillation is specifically as follows: the 1-chlorobutane is first recovered by distillation at 80 ℃ and then distilled at 145 ℃ to obtain valeronitrile.
The 1-chlorobutane is distilled and recovered at a lower temperature, the valeronitrile is obtained by distillation at a higher temperature, and the unreacted 1-chlorobutane is directly recycled, so that the waste of resources is avoided, and the influence on the purity of the valeronitrile can be reduced.
The application has the following beneficial effects:
(1) according to the method, sodium cyanide and 1-chlorobutane are used as raw materials to produce the valeronitrile, the cost of the raw materials is relatively low, the yield of the valeronitrile prepared by the method is high, and the purity of the product is high. Excessive 1-chlorobutane is adopted to react with sodium cyanide, so that the reaction of the sodium cyanide is promoted to be complete, the unreacted sodium cyanide does not need to be treated by excessive sodium hypochlorite after the reaction is finished, the generation of three wastes is reduced, and the method is environment-friendly. And because the waste liquid of sodium cyanide has relatively great potential safety hazard, the sodium cyanide meets acid and produces the cyanohydric acid, colorless tasteless but virulent, there is the safety problem easily, this application uses excessive 1-chlorobutane to cooperate with catalyst to impel the sodium cyanide reaction to be complete, reduces the potential safety hazard.
(2) In the application, the excessive 1-chlorobutane can be directly distilled and recovered in the organic layer distillation stage, the 1-chlorobutane is distilled and recovered at a lower temperature, the valeronitrile is obtained by distillation at a higher temperature, and the unreacted 1-chlorobutane is directly recycled, so that the waste of resources is avoided, and the influence on the purity of the valeronitrile can be reduced.
(3) The method adopts the mixture of tetrabutylammonium bromide and triethylamine as the catalyst, is favorable for providing yield and product purity, and can further improve the yield and the product purity after the catalyst promoter isopropanol is added.
Detailed Description
The present application will now be described in further detail with reference to examples.
Example 1
163.4g of 30 mass percent sodium cyanide solution (1 mol of sodium cyanide), 139g of 1-chlorobutane (1.50 mol) and 10 g of catalyst (10 g of tetrabutylammonium bromide) are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is almost complete, and the mixture is kept stand and layered. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 90.0% yield and 99.50% purity.
Example 2
163.4g (1 mol of sodium cyanide), 139g (1.50 mol) of 1-chlorobutane and 10 g of catalyst (7 g of tetrabutylammonium bromide and 3 g of triethylamine) of 30 mass percent sodium cyanide solution are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is almost complete, and the mixture is stood for layering. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 90.8% yield and 99.56% purity.
Example 3
163.4g of 30 mass percent sodium cyanide solution (1 mol of sodium cyanide), 139g of 1-chlorobutane (1.50 mol), 10 g of catalyst (7 g of tetrabutylammonium bromide and 3 g of triethylamine) and 40 g of cocatalyst (40 g of isopropanol) are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is basically completed, and the mixture is stood for demixing. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 92.3% yield and 99.84% purity.
Example 4
163.4g of 30 mass percent sodium cyanide solution (1 mol of sodium cyanide), 139g of 1-chlorobutane (1.50 mol), 10 g of catalyst (6.67 g of tetrabutylammonium bromide and 3.33 g of triethylamine) and 50 g of cocatalyst (50 g of isopropanol) are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is almost complete, and the mixture is stood for layering. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 91.4% yield and 99.62% purity.
Example 5
163.4g of 30 mass percent sodium cyanide solution (1 mol of sodium cyanide), 139g of 1-chlorobutane (1.50 mol), 10 g of catalyst (7.69 g of tetrabutylammonium bromide and 2.31 g of triethylamine) and 30 g of cocatalyst (30 g of isopropanol) are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is almost complete, and the mixture is stood for layering. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 92.7% yield and 99.75% purity.
Example 6
163.4g of 30 mass percent sodium cyanide solution (1 mol of sodium cyanide), 101.8 g of 1-chlorobutane (1.10 mol), 10 g of catalyst (7 g of tetrabutylammonium bromide and 3 g of triethylamine) and cocatalyst (40 g of isopropanol) are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is basically completed, and the mixture is kept stand and layered. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 90.5% yield and 99.87% purity.
Example 7
163.4g of 30 mass percent sodium cyanide solution (1 mol of sodium cyanide), 175.9 g of 1-chlorobutane (1.90 mol), 10 g of catalyst (7 g of tetrabutylammonium bromide and 3 g of triethylamine) and cocatalyst (40 g of isopropanol) are added into a 1000mL four-mouth reaction bottle, the temperature is slowly increased to 60 ℃, the temperature is kept for 4 hours, the reaction is basically completed, and the mixture is stood for demixing. The organic layer was distilled at 80 ℃ to recover 1-chlorobutane and at 145 ℃ to afford valeronitrile in 92.5% yield and 99.82% purity.
Comparative example 1
In a 1000ml four-necked reaction flask, 179.7g (1.5 mol of sodium cyanide), 92.57g (1.0 mol) of 1-chlorobutane and 10 g of a catalyst (10 g of tetrabutylammonium bromide) of a 30% sodium cyanide solution were added, and the mixture was slowly heated to 60 ℃ and kept warm for 4 hours, and then allowed to stand to separate. The organic layer was distilled at 145 ℃ to give valeronitrile in 89.0% yield and 99.20% purity. There was more sodium cyanide remaining.
As can be seen from the above examples and comparative examples, in example 1, the reaction was carried out with a molar ratio of sodium cyanide to 1-chlorobutane of 1:1.5, and tetrabutylammonium bromide alone was used as a catalyst to prepare valeronitrile, the final yield could reach 90.0% and the purity could reach 99.50%. The sodium cyanide basically reacts completely, so that the post-treatment is facilitated, the unreacted sodium cyanide does not need to be treated by excessive sodium hypochlorite after the reaction is finished, the generation of three wastes is reduced, and the method is environment-friendly. And because the waste liquid of sodium cyanide has relatively great potential safety hazard, the sodium cyanide meets acid and produces the cyanohydric acid, colorless tasteless but virulent, there is the safety problem easily, this application uses excessive 1-chlorobutane to cooperate with catalyst to impel the sodium cyanide reaction to be complete, reduces the potential safety hazard.
In the example 2, the tetrabutylammonium bromide and the triethylamine are compounded to be used as the catalyst, the yield of the valeronitrile is improved to 90.8% under the same condition, the purity is increased to 99.56%, and the condition that the triethylamine is compounded in the tetrabutylammonium bromide can make up the defects of the tetrabutylammonium bromide serving as a single catalyst and improve the yield of the product.
In example 3, the cocatalyst is added on the basis of example 2, the yield of the valeronitrile under the same conditions is further increased to 92.3%, and the purity is increased to 99.84%, which is probably because the addition of the isopropanol helps to increase the solubility of the triethylamine in the reaction system and improve the catalytic activity.
In example 6, the amount of 1-chlorobutane used was reduced based on example 3 so that the molar ratio of NaCN to 1-chlorobutane became 1:1.10, and the final valeronitrile yield decreased to 90.5%, indicating that more 1-chlorobutane favors more complete reaction.
In example 7, the molar ratio of sodium cyanide to 1-chlorobutane was increased to 1:1.90 in addition to example 3, and the final yield of valeronitrile was 92.5%, which was slightly higher than that in example 3, indicating that more 1-chlorobutane could not significantly improve the yield of valeronitrile, i.e., it was more appropriate to select the molar ratio of sodium cyanide to 1-chlorobutane to 1: 1.50.
In comparative example 1, the molar ratio of sodium cyanide to 1-chlorobutane was changed to 1.5:1.0, and excess sodium cyanide was used as the starting material, but the yield of valeronitrile was only 89.0%, which was lower than 90.0% in example 1, and the excess sodium cyanide did not give a higher yield, and also caused the residue of excess sodium cyanide, and it was necessary to treat unreacted sodium cyanide with excess sodium hypochlorite, which was not environmentally friendly. In addition, the waste liquid containing sodium cyanide has a relatively large potential safety hazard. Sodium cyanide produces cyanohydric acid when meeting acid, is colorless, tasteless and extremely toxic, and easily causes safety problems.
The present embodiment is merely illustrative and not restrictive, and various changes and modifications may be made by persons skilled in the art without departing from the scope of the present invention as defined in the appended claims. The technical scope of the present application is not limited to the contents of the specification, and must be determined according to the scope of the claims.
Claims (10)
1. A preparation method of valeronitrile is characterized by comprising the following steps: the preparation method comprises the following steps: sodium cyanide and excessive 1-chlorobutane are used as raw materials and react under the action of a catalyst to generate valeronitrile.
2. A process for the preparation of valeronitrile according to claim 1 wherein: the molar ratio of the sodium cyanide to the 1-chlorobutane is 1: 1.1-1.9.
3. A process for the preparation of valeronitrile according to claim 1 wherein: the molar ratio of sodium cyanide to 1-chlorobutane is 1: 1.5.
4. A process for the preparation of valeronitrile according to claim 1 wherein: the sodium cyanide is a sodium cyanide solution with the mass percentage concentration of 30%.
5. A process for the preparation of valeronitrile according to claim 1 wherein: the dosage of the catalyst is 5-10% of the total mass of the 1-chlorobutane; the catalyst comprises tetrabutylammonium bromide.
6. A process for the preparation of valeronitrile according to claim 5 which comprises: the catalyst also comprises triethylamine, and the mass ratio of the tetrabutylammonium bromide to the triethylamine is 1: 0.3-0.5.
7. A process for the preparation of valeronitrile according to claim 1 wherein: and a cocatalyst is also added in the reaction, the cocatalyst is isopropanol, and the mass ratio of tetrabutylammonium bromide to isopropanol is 1: 3-5.
8. A process for the preparation of valeronitrile according to claim 1 wherein: the preparation method specifically comprises the following steps: adding sodium cyanide, 1-chlorobutane and a catalyst into a reaction kettle, heating to the reaction temperature under stirring, reacting for 3-4 h, standing for layering, and then distilling an organic layer to obtain valeronitrile.
9. A process for the preparation of valeronitrile according to claim 7 wherein: the reaction temperature is 20-100 ℃, preferably, the reaction temperature is 50-90 ℃.
10. A process for the preparation of valeronitrile according to claim 1 wherein: the organic layer distillation specifically comprises the following steps: the 1-chlorobutane is first recovered by distillation at 80 ℃ and then distilled at 145 ℃ to obtain valeronitrile.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006097808A1 (en) * | 2005-03-15 | 2006-09-21 | Pfizer Japan Inc. | Benzimidazolone derivatives as cb2 receptor ligands |
| CN110845362A (en) * | 2019-11-28 | 2020-02-28 | 安徽泰格生物科技有限公司 | Preparation method of hydroxypivaonitrile |
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2021
- 2021-12-24 CN CN202111598761.8A patent/CN114292209B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006097808A1 (en) * | 2005-03-15 | 2006-09-21 | Pfizer Japan Inc. | Benzimidazolone derivatives as cb2 receptor ligands |
| CN110845362A (en) * | 2019-11-28 | 2020-02-28 | 安徽泰格生物科技有限公司 | Preparation method of hydroxypivaonitrile |
Non-Patent Citations (2)
| Title |
|---|
| BRANKO JURSIC ET AL.: "Preparation of nitriles by cyanide displacement on primary alkyl halides in reversed micelles", 《JOURNAL OF CHEMICAL RESEARCH, SYNOPSES》, no. 10, pages 336 - 337, XP003015440 * |
| 杜乾等: "正戊腈合成研究", 《精细与专用化学品》, vol. 26, no. 3, pages 15 - 17 * |
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