CN114292209B - Preparation method of valeronitrile - Google Patents
Preparation method of valeronitrile Download PDFInfo
- Publication number
- CN114292209B CN114292209B CN202111598761.8A CN202111598761A CN114292209B CN 114292209 B CN114292209 B CN 114292209B CN 202111598761 A CN202111598761 A CN 202111598761A CN 114292209 B CN114292209 B CN 114292209B
- Authority
- CN
- China
- Prior art keywords
- sodium cyanide
- valeronitrile
- chlorobutane
- reaction
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 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 61
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 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 group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 15
- 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
- 230000009965 odorless effect Effects 0.000 abstract description 4
- 231100000331 toxic Toxicity 0.000 abstract description 4
- 230000002588 toxic effect Effects 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000002349 favourable 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
- 230000007547 defect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 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
- 238000013329 compounding Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229960000519 losartan potassium Drugs 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 group [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing 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 to react under the action of a catalyst to generate valeronitrile. The method for preparing the valeronitrile by using the sodium cyanide and the 1-chlorobutane as raw materials has the advantages of relatively low raw material cost, high yield of the valeronitrile prepared by using the method and high purity of the product. And excessive 1-chlorobutane is adopted to react with sodium cyanide, so that the reaction of the sodium cyanide is promoted to be complete, and after the reaction is finished, the unreacted sodium cyanide is not required to be treated by excessive sodium hypochlorite, thereby reducing the generation of three wastes and being environment-friendly. And because the waste liquid of sodium cyanide has relatively large potential safety hazard, sodium cyanide generates cyanohydrin acid when meeting acid, is colorless, odorless and extremely toxic, and is easy to have safety problem, the excessive 1-chlorobutane matched catalyst is used for promoting the complete reaction of the sodium cyanide, so that the potential safety hazard is reduced.
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 an imidazole aldehyde which is a key intermediate of losartan potassium serving as a hypertension drug. The traditional preparation process adopts 1-bromobutane and sodium cyanide as raw materials, but the 1-bromobutane has higher cost and is not beneficial to the reduction of 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; secondly, n-butyl alcohol and tetrabutylammonium cyanide are used as raw materials. However, the two methods have some defects, the storage condition of the valeraldehyde raw material in the first method is harsh, and the storage is improper and easy to deteriorate; the starting material tetrabutylammonium cyanide in process two is expensive and difficult to obtain.
In view of this, there is a need to develop a new process for preparing valeronitrile which uses inexpensive and readily available starting materials and which is capable of achieving higher yields.
Disclosure of Invention
In order to solve the problems, the application discloses a preparation method of valeronitrile, which takes sodium cyanide and 1-chlorobutane as raw materials to produce valeronitrile, the raw material cost is relatively low, and the method is adopted to prepare the valeronitrile with high yield and high product purity.
The application provides a preparation method of valeronitrile, which adopts the following technical scheme:
a process for the preparation of valeronitrile, comprising the steps of: sodium cyanide and excessive 1-chlorobutane are used as raw materials to react under the action of a catalyst to generate valeronitrile.
The method adopts sodium cyanide and excessive 1-chlorobutane to react to prepare the valeronitrile, so that 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 is not required 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 the sodium cyanide to the 1-chlorobutane is 1:1.1-1.9.
Preferably, the molar ratio of the sodium cyanide to the 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, which is favorable for forward reaction, avoids excessive unreacted sodium cyanide remained in the system and can also avoid excessive use of the 1-chlorobutane.
Preferably, the sodium cyanide is a sodium cyanide solution with a mass percent concentration of 30%.
The sodium cyanide is added dropwise in the form of a solution, so that the full reaction of the sodium cyanide is facilitated, the post-treatment is facilitated, and the pollution to the environment is reduced.
Preferably, the catalyst is used in an amount of 5-10% of the total mass of 1-chlorobutane; the catalyst comprises tetrabutylammonium bromide.
Preferably, the catalyst further comprises triethylamine, and the mass ratio of tetrabutylammonium bromide to triethylamine is 1:0.3-0.5.
The inventors found in experiments that tetrabutylammonium bromide and triethylamine as combined catalysts are advantageous in obtaining higher yields and product purity.
Preferably, a cocatalyst is also added in the reaction, wherein the cocatalyst is isopropanol, and the mass ratio of tetrabutylammonium bromide to isopropanol is 1:3-5..
The inventors found in experiments that a slight amount of isopropanol was added to the catalyst to further promote the improvement of the yield and the purity of the product.
Preferably, the preparation method specifically comprises the following steps: adding sodium cyanide, 1-chlorobutane and a catalyst into a reaction kettle, heating to a reaction temperature under stirring, reacting 3-4 h, ending the reaction, standing for layering, and then distilling an organic layer to obtain valeronitrile.
The inventor discovers that the raw material proportion, the catalyst and the cocatalyst can be adopted to enable the sodium cyanide to react basically and completely in the reaction of about 3-4 h, so that excessive residual sodium cyanide in the reaction kettle can be avoided, the post-treatment is not facilitated, and the potential safety hazard is brought.
Preferably, the reaction temperature is 20 to 100 ℃, preferably 50 to 90 ℃.
The inventors found that the reaction temperature is controlled to 50-90℃to facilitate the reaction.
Preferably, the organic layer distillation is specifically: the 1-chlorobutane was recovered by distillation at 80℃and then distilled at 145℃to give valeronitrile.
The method comprises the steps of distilling and recovering 1-chlorobutane at a lower temperature, and then distilling and obtaining valeronitrile at a higher temperature, wherein 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) The method for preparing the valeronitrile by using the sodium cyanide and the 1-chlorobutane as raw materials has the advantages of relatively low raw material cost, high yield of the valeronitrile prepared by using the method and high purity of the product. And excessive 1-chlorobutane is adopted to react with sodium cyanide, so that the reaction of the sodium cyanide is promoted to be complete, and after the reaction is finished, the unreacted sodium cyanide is not required to be treated by excessive sodium hypochlorite, thereby reducing the generation of three wastes and being environment-friendly. And because the waste liquid of sodium cyanide has relatively large potential safety hazard, sodium cyanide generates cyanohydrin acid when meeting acid, is colorless, odorless and extremely toxic, and is easy to have safety problem, the excessive 1-chlorobutane matched catalyst is used for promoting the complete reaction of the sodium cyanide, so that the potential safety hazard is reduced.
(2) 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, then the valeronitrile is obtained by distillation at a higher temperature, the unreacted 1-chlorobutane is directly recycled, 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 the yield and the product purity, and can further improve the yield and the product purity after the promoter isopropanol is added.
Detailed Description
The present application will now be described in further detail with reference to examples.
Example 1
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30%, 139g (1.50 mol) of 1-chlorobutane and 10 g of catalyst (tetrabutylammonium bromide 10 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ and the temperature is kept for 4 hours, the reaction is basically complete, and the mixture is kept stand for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and at 145℃to give valeronitrile in 90.0% yield and 99.50% purity.
Example 2
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30%, 139g (1.50 mol) of 1-chlorobutane and 10 g catalyst (tetrabutylammonium bromide 7g and triethylamine 3 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ and the temperature is kept for 4 hours, the reaction is basically complete, and the mixture is kept stand for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and at 145℃to give valeronitrile in 90.8% yield and 99.56% purity.
Example 3
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30 percent, 139g (1.50 mol) of 1-chlorobutane, 10 g catalyst (tetrabutylammonium bromide 7g, triethylamine 3 g) and 40 g catalyst promoter (isopropanol 40 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ for 4 hours, the reaction is basically complete, and the mixture is stood for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and at 145℃to give valeronitrile in 92.3% yield and 99.84% purity.
Example 4
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30 percent, 139g (1.50 mol) of 1-chlorobutane, 10 g catalyst (tetrabutylammonium bromide 6.67 g, triethylamine 3.33 g) and 50 g catalyst promoter (isopropanol 50 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ for 4 hours, the reaction is basically complete, and the mixture is kept stand for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and 145℃to give valeronitrile in 91.4% yield and 99.62% purity.
Example 5
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30 percent, 139g (1.50 mol) of 1-chlorobutane, 10 g catalyst (tetrabutylammonium bromide 7.69 g, triethylamine 2.31 g) and 30 g catalyst promoter (isopropanol 30 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ for 4 hours, the reaction is basically complete, and the mixture is kept stand for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and at 145℃to give valeronitrile in 92.7% yield and 99.75% purity.
Example 6
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30 percent, 101.8 g (1.10 mol) of 1-chlorobutane, 10 g catalyst (tetrabutylammonium bromide 7g, triethylamine 3 g) and cocatalyst (isopropanol 40 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ for 4 hours, the reaction is basically complete, and the mixture is stood for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and at 145℃to give valeronitrile in 90.5% yield and 99.87% purity.
Example 7
163.4g (1 mol) of sodium cyanide solution with the mass percent concentration of 30 percent, 175.9 g (1.90 mol) of 1-chlorobutane, 10 g catalyst (tetrabutylammonium bromide 7g, triethylamine 3 g) and cocatalyst (isopropanol 40 g) are added into a four-port reaction bottle of 1000mL, the temperature is slowly increased to 60 ℃ for 4 hours, the reaction is basically complete, and the mixture is stood for layering. The organic layer was distilled at 80℃to recover 1-chlorobutane and at 145℃to give valeronitrile in 92.5% yield and 99.82% purity.
Comparative example 1
Into a 1000ml four-port reaction flask, 179.7g (1.5 mol) of 30% sodium cyanide solution and 92.57g (1.0 mol) of 1-chlorobutane were added, and the mixture was slowly warmed to 60℃and kept for 4 hours, and then allowed to stand for delamination, followed by 10-g catalyst (tetrabutylammonium bromide 10 g). The organic layer was distilled at 145 ℃ to give valeronitrile in 89.0% yield and 99.20% purity. There is more sodium cyanide remaining.
As can be seen from the above examples and comparative examples, in example 1, valeronitrile was prepared by carrying out the reaction in a molar ratio of 1:1.5 of sodium cyanide to 1-chlorobutane and using tetrabutylammonium bromide alone as a catalyst, and the final yield could reach 90.0% and the purity could reach 99.50%. The sodium cyanide basically reacts completely, is favorable for post-treatment, does not need to treat unreacted sodium cyanide by adopting excessive sodium hypochlorite after the reaction is finished, reduces the generation of three wastes, and is environment-friendly. And because the waste liquid of sodium cyanide has relatively large potential safety hazard, sodium cyanide generates cyanohydrin acid when meeting acid, is colorless, odorless and extremely toxic, and is easy to have safety problem, the excessive 1-chlorobutane matched catalyst is used for promoting the complete reaction of the sodium cyanide, so that the potential safety hazard is reduced.
In the example 2, tetrabutylammonium bromide and triethylamine are compounded to be used as catalysts, the yield of valeronitrile is improved to 90.8 percent under the same condition, the purity is improved to 99.56 percent, and the defect of the tetrabutylammonium bromide with a single catalyst can be overcome by compounding the triethylamine in the tetrabutylammonium bromide, so that the product yield is improved.
In example 3, the cocatalyst is added on the basis of example 2, the yield of valeronitrile is further increased to 92.3% under the same conditions, and the purity is improved to 99.84%, which is probably due to the fact that the addition of isopropanol helps to increase the solubility of triethylamine in the reaction system and improve the catalytic activity.
In example 6, the amount of 1-chlorobutane was reduced based on example 3, so that the molar ratio of sodium cyanide to 1-chlorobutane was changed to 1:1.10, and the final valeronitrile yield was reduced to 90.5%, indicating that more 1-chlorobutane was beneficial to more complete reaction.
In example 7, the amount of 1-chlorobutane is increased based on example 3, so that the molar ratio of sodium cyanide to 1-chlorobutane is changed to 1:1.90, the final yield of valeronitrile is 92.5%, and compared with example 3, the yield of valeronitrile is slightly increased, which indicates that more 1-chlorobutane cannot significantly improve the yield of valeronitrile, namely, the molar ratio of sodium cyanide to 1-chlorobutane is changed to 1:1.50.
The molar ratio of sodium cyanide to 1-chlorobutane in comparative example 1 was changed to 1.5:1.0, and excessive sodium cyanide was used as a raw material, but the valeronitrile yield was only 89.0%, which was lower than 90.0% of example 1, and excessive sodium cyanide was not only unable to obtain higher yields, but also resulted in excessive sodium cyanide residue, and the unreacted sodium cyanide was required to be treated with excessive sodium hypochlorite, which was not friendly to the environment. In addition, the waste liquid containing sodium cyanide has a relatively large potential safety hazard. Sodium cyanide generates cyanogen acid when meeting acid, is colorless, odorless and highly toxic, and is easy to generate safety problem.
The present embodiment is merely illustrative of the present application, and the present application is not limited thereto, and a worker can make various changes and modifications without departing from the scope of the technical idea of the present application. 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 claims.
Claims (3)
1. A preparation method of valeronitrile is characterized in that: the preparation method comprises the following steps: sodium cyanide and excessive 1-chlorobutane are used as raw materials to react under the action of a catalyst to generate valeronitrile; the molar ratio of the sodium cyanide to the 1-chlorobutane is 1:1.5-1.9; the catalyst is tetrabutylammonium bromide and triethylamine; the preparation method specifically comprises the following steps: adding sodium cyanide, 1-chlorobutane and a catalyst into a reaction kettle, heating to a reaction temperature under stirring, reacting 3-4 h to finish the reaction, standing for layering, and then distilling an organic layer to obtain valeronitrile; the organic layer distillation is specifically as follows: firstly, distilling at 80 ℃ to recover 1-chlorobutane, and then distilling at 145 ℃ to obtain valeronitrile; the dosage of the catalyst is 5-10% of the total mass of the 1-chlorobutane; the mass ratio of the catalyst tetrabutylammonium bromide to the triethylamine is 1:0.3-0.5; the reaction temperature is 50-60 ℃.
2. The method for producing valeronitrile according to claim 1, wherein: the sodium cyanide is a sodium cyanide solution with the mass percent concentration of 30 percent.
3. The method for producing valeronitrile according to claim 1, wherein: and a cocatalyst is also added in the reaction, wherein the cocatalyst is isopropanol, and the mass ratio of tetrabutyl ammonium bromide to isopropanol is 1:3-5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111598761.8A CN114292209B (en) | 2021-12-24 | 2021-12-24 | Preparation method of valeronitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111598761.8A CN114292209B (en) | 2021-12-24 | 2021-12-24 | Preparation method of valeronitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114292209A CN114292209A (en) | 2022-04-08 |
| CN114292209B true CN114292209B (en) | 2024-01-05 |
Family
ID=80969090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111598761.8A Active CN114292209B (en) | 2021-12-24 | 2021-12-24 | Preparation method of valeronitrile |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114292209B (en) |
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 |
-
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 |
|---|
| Preparation of nitriles by cyanide displacement on primary alkyl halides in reversed micelles;Branko Jursic et al.;《Journal of Chemical Research, Synopses》(第10期);336-337 * |
| 正戊腈合成研究;杜乾等;《精细与专用化学品》;第26卷(第3期);15-17 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114292209A (en) | 2022-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105777535B (en) | Process for preparing glucaric acid | |
| CN113372241B (en) | Method for synthesizing dinitrile ethyl tertiary amine by aliphatic primary amine one-step method | |
| CN101838221A (en) | Manufacturing method of atorvastatin intermediate (R)-(-)-4-nitrile-3-hydroxybutyrate | |
| CN114292209B (en) | Preparation method of valeronitrile | |
| CN102557952B (en) | Method for preparing di-tert-butyl dicarbonate | |
| CN102746161A (en) | Method for synthesizing 1,8-terpene diamine | |
| CN107488136B (en) | Method for preparing ethyl hydrogen sulfate | |
| CN1594281A (en) | Process for preparing iminodiacetic acid | |
| WO2014202031A1 (en) | Method for co-production of adipic acid and nitrocyclohexane | |
| CN1511818A (en) | Process for preparing 2-(alkyl) cyclic ketone | |
| CN108530301B (en) | Synthetic method of 2,4, 6-trifluorobenzylamine | |
| WO2013002397A1 (en) | Method for producing furfural compound, and apparatus for producing furfural compound | |
| CN114315532B (en) | Method for synthesizing 1, 4-tetraalkoxy-2-butene from 2, 2-dialkoxy acetaldehyde | |
| CN1765862A (en) | Method for synthesizing alkynol by ketone and acetylene | |
| JP2001233844A (en) | Method for producing 3-hydroxypropionitrile | |
| CN107954843B (en) | Method for synthesizing p-tert-butyl benzene propionaldehyde | |
| CN112279783B (en) | Method for preparing 3-hydroxypropionitrile under supercritical condition | |
| KR100921944B1 (en) | Process for preparing of epichlorohydrine | |
| CN110563586A (en) | Method for preparing dimethyl carbonate in one pot under low pressure condition | |
| CN112521265B (en) | Method for continuously producing glycollic acid | |
| CN109134312B (en) | Preparation method of 2-phenyl acrylonitrile | |
| WO2024077796A1 (en) | Production method for ethyl 8-chlorooctanoate | |
| JP5284350B2 (en) | Simultaneous production of cyclic carbonates and aliphatic nitriles and / or amines | |
| CN101613254B (en) | Method for directly preparing 1,3-dichloro-2-propanol by catalyzing glycerol with sulfur and zirconium | |
| CN108236945B (en) | Heteropolyacid slurry catalyst, preparation and application in hydroxylamine hydrochloride catalytic synthesis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |