CN110922341B - Preparation method of methoxylamine hydrochloride - Google Patents
Preparation method of methoxylamine hydrochloride Download PDFInfo
- Publication number
- CN110922341B CN110922341B CN201911281544.9A CN201911281544A CN110922341B CN 110922341 B CN110922341 B CN 110922341B CN 201911281544 A CN201911281544 A CN 201911281544A CN 110922341 B CN110922341 B CN 110922341B
- Authority
- CN
- China
- Prior art keywords
- butanone oxime
- reaction
- triethylamine
- temperature
- methoxylamine hydrochloride
- 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
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012022 methylating agents Substances 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- -1 C) 2 H 6 OS) Chemical compound 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 11
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 5
- 235000010288 sodium nitrite Nutrition 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 231100000614 poison Toxicity 0.000 abstract description 3
- 239000002341 toxic gas Substances 0.000 abstract description 3
- 239000003440 toxic substance Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 10
- 239000012295 chemical reaction liquid Substances 0.000 description 9
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229960001668 cefuroxime Drugs 0.000 description 3
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 239000005800 Kresoxim-methyl Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 108090000204 Dipeptidase 1 Proteins 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- BSDQITJYKQHXQR-UHFFFAOYSA-N methyl prop-2-eneperoxoate Chemical compound COOC(=O)C=C BSDQITJYKQHXQR-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of methoxylamine hydrochloride, which comprises the following steps: adding butanone oxime (C4H 9 NO), dimethyl sulfoxide (DMSO, C2H6 OS), triethylamine (C6H 15N) and a methylating agent into a reaction container, and reacting at 15-75 ℃ to generate O-methyl-2-butanone oxime ether; compared with the prior art, the method has the advantages that the operation is simple, three wastes are less, reaction raw materials can be completely converted, generated intermediate byproducts can be decomposed into butanone oxime (C4H 9 NO) and triethylamine (C6H 15N), NO side reaction is generated, the yield of the synthetic methoxyamine hydrochloride is improved, toxic substances such as sulfur dioxide and sodium nitrite are avoided, the emission of toxic gases such as nitrogen oxides is reduced, and the sustainable development of enterprises is facilitated.
Description
Technical Field
The invention relates to a preparation method of methoxylamine hydrochloride, belonging to the technical field of medical intermediates.
Background
The methoxylamine hydrochloride is an important pharmaceutical and chemical intermediate, and is mainly applied to the production of cefuroxime and phenoxy kresoxim-methyl. Cefuroxime belongs to cephalosporin antibiotics, and is widely applied due to the characteristics of wide antibacterial spectrum, stability to beta-lactamase and the like. The phenoxy-methyl is a good variety in methoxy acrylate bactericides and has high bactericidal activity and high selectivity. With the increasing production of cefuroxime and phenoxy kresoxim-methyl in recent years, the demand of the international market for the methoxylamine hydrochloride is gradually increased. However, the production of methoxylamine hydrochloride in China generally has the problems of backward process, serious three wastes, high product cost and the like. Therefore, the method has important significance for the development and research of the synthesis process of the methoxylamine hydrochloride.
The current synthetic routes of methoxylamine hydrochloride mainly comprise the following steps:
in 2009 Chinese patent CN101503375A, butanone oxime and sodium hydroxide are used as raw materials, a phase transfer catalyst and a methylation reagent are added to prepare oxime ether, and the oxime ether is mixed with hydrochloric acid and rectified to prepare methoxylamine hydrochloride. The method has the advantages of complex steps, complex operation, long high-temperature reaction time and high energy consumption, and is not suitable for industrial production.
In 2015, CN105330564A is prepared by connecting sulfur dioxide gas, sodium nitrite, sodium hydroxide and dimethyl sulfate in an aqueous phase in series by a one-pot method to prepare methoxyamine hydrochloride. The process uses sulfur dioxide and sodium nitrite, has high toxicity and serious pollution, generates a large amount of waste gas of nitrogen oxides and the like, has certain problems in safety and environmental protection, and is not suitable for industrial production.
Disclosure of Invention
The invention aims to provide a preparation method of methoxylamine hydrochloride, which uses triethylamine to replace sodium hydroxide to participate in reaction, can reduce the generation of reaction byproducts, improve the yield of the synthetic methoxylamine hydrochloride, avoid the use of toxic substances such as sulfur dioxide and sodium nitrite, and reduce the emission of toxic gases such as nitrogen oxides.
The preparation method of methoxylamine hydrochloride comprises the following steps:
1. adding butanone oxime (C4H 9 NO), dimethyl sulfoxide (DMSO, C2H6 OS), triethylamine (C6H 15N) and a methylating agent into a reaction container, and reacting at 15-75 ℃ to generate O-methyl-2-butanone oxime ether;
2. adding hydrochloric acid into the O-methyl-2-butanone oxime ether in the step 1 for acidification to obtain a target product methoxylamine hydrochloride,
wherein the molar ratio of the butanone oxime (C4H 9 NO) to the triethylamine (C6H 15N) is 1.3 to 1.5, and the molar quantity of the dimethyl sulfoxide (DMSO and C2H6 OS) is 2.2 to 2.4 times of that of the butanone oxime.
Further, the concentration of the hydrochloric acid is 30-35%, and the acidification time is 2-4h.
Furthermore, the methylating agent is methyl iodide (CH 3I), dimethyl sulfate (C2H 6O 4S), methyl chloride (CH 3 Cl) and the like, and the molar ratio of the butanone oxime (C4H 9 NO) to the methylating agent is 1.
Further, the molar ratio of the hydrochloric acid to the butanone oxime (C4H 9 NO) is 1 to 2.
Further, the reaction time in the step 1 is 6 to 10 hours.
The invention relates to a preparation method of methoxylamine hydrochloride. The preparation method comprises the steps of adding butanone oxime (C4H 9 NO), dimethyl sulfoxide (DMSO, C2H6 OS), triethylamine (C6H 15N) and a methylating agent into a reaction container under a high-temperature condition, reacting for 6 to 10h, and hydrolyzing for 2 to 4h under an acidic condition to obtain butanone (C4H 8O) and methoxylamine hydrochloride (CH 6 ClNO).
The relevant reaction formula is as follows:
①
②
the invention has the following beneficial effects:
1. the butanone oxime (C4H 9 NO) as the raw material is converted into the target product O-methyl-2-butanone oxime ether and the byproduct 2, the raw material can be completely converted, but the byproduct 2 is unstable and can be decomposed into the butanone oxime (C4H 9 NO) and the triethylamine (C6H 15N), and NO side reaction is generated, so that the yield of the synthetic methoxylamine hydrochloride is improved, and the yield of the synthetic methoxylamine hydrochloride is more than 87%.
2. The invention avoids using toxic substances such as sulfur dioxide, sodium nitrite and the like, reduces the emission of toxic gases such as nitric oxide and the like, and is easier to realize industrialization.
3. Compared with the traditional method adopting NaOH reaction, the method provided by the invention can not cause waste of raw materials, and avoids the problem of low product yield caused by incomplete reaction of butanone oxime.
4. The method of the invention does not need to carry out treatments such as liquid separation, distillation and the like because water is not used as a solvent, thereby greatly improving the production efficiency.
Detailed Description
The present invention is further described below with reference to examples.
Example 1
43.5g (0.5 mol) of butanone oxime (C4H 9 NO), 70.8g (0.7 mol) of triethylamine (C6H 15N), 87g (1.1 mol) of dimethyl sulfoxide (DMSO, C2H6 OS) are added into a 500ml reaction bottle, 82g (0.65 mol) of dimethyl sulfate (C2H 6O 4S) is slowly added dropwise when the temperature is raised to 60 ℃, the dropwise adding time is 50min, the temperature is kept for 6H after the dropwise adding is finished, the reaction liquid is transferred into the 500ml reaction bottle, 78.2g (0.75 mol) of 35% hydrochloric acid is added into the 500ml reaction bottle, the reaction liquid is reacted for 120min at 100 ℃, the reaction liquid is cooled to room temperature for crystallization and filtration, and the target product is obtained, wherein the yield is 87%.
Example 2
Adding 52.3g (0.6 mol) of butanone oxime (C4H 9 NO), 98g (0.97 mol) of triethylamine (C6H 15N), 111g (1.42 mol) of dimethyl sulfoxide (DMSO, C2H6 OS) into a 500ml reaction bottle, heating to 40 ℃, slowly dropwise adding 77.3g (0.61 mol) of dimethyl sulfate (C2H 6O 4S) for 90min, keeping the temperature for 7H after dropwise adding, transferring the reaction liquid into the 500ml reaction bottle, adding 93.7g (0.9 mol) of 35% hydrochloric acid into the 500ml reaction bottle, reacting for 140min at 120 ℃, cooling to room temperature, crystallizing and filtering to obtain the target product, wherein the yield is 91%.
Example 3
61g (0.7 mol) of butanone oxime (C4H 9 NO), 106.2g (1.05 mol) of triethylamine (C6H 15N), 122g (1.56 mol) of dimethyl sulfoxide (DMSO, C2H6 OS) are added into a 500ml reaction bottle, the temperature is raised to 75 ℃, 123.6g (0.98 mol) of dimethyl sulfate (C2H 6O 4S) is slowly added dropwise, the dropwise adding time is 30min, the temperature is kept for 8H after the dropwise adding is finished, the reaction liquid is transferred into the 500ml reaction bottle, 104.3g (1 mol) of 35% hydrochloric acid is added into the 500ml reaction bottle, the reaction is carried out for 110min at 95 ℃, the temperature is reduced to room temperature, crystallization and filtration is carried out, so that the target product is obtained, and the yield is 89%.
Comparative example 1
61g of butanone oxime (C4H 9 NO), 1.05mol of sodium hydroxide and 122g of dimethyl sulfoxide (DMSO, C2H6 OS) are added into a 500ml reaction bottle, the temperature is raised to 75 ℃, 123.6g of dimethyl sulfate (C2H 6O 4S) is slowly dripped, the dripping time is 30min, the temperature is kept for 8H after the dripping is finished, liquid separation is carried out after the reaction is finished, an upper-layer water phase is separated, then the water layer is distilled to the gas phase temperature of 92 ℃ under normal pressure, O-methyl-2-ketoxime ether and methanol in the water layer are recovered, the reaction liquid is transferred into the 500ml reaction bottle, 104.3g (1 mol) of 35% hydrochloric acid is added to react for 110min at 95 ℃, the temperature is reduced to room temperature, crystallization and filtration are carried out, and a target product is obtained, and the yield is 78%.
Comparative example 2
61g of butanone oxime (C4H 9 NO), 1.05mol of sodium hydroxide and 1.56mol of PEG-200 are added into a 500ml reaction bottle, the temperature is raised to 75 ℃, 123.6g of dimethyl sulfate (C2H 6O 4S) is slowly dripped for 30min, the temperature is kept for 8H after the dripping is finished, liquid is separated after the reaction is finished, an upper layer of water phase is separated, then the water layer is distilled under normal pressure to the gas phase temperature of 96 ℃, O-methyl-2-butanone oxime ether and methanol in the water layer are recovered, the reaction liquid is transferred into the 500ml reaction bottle, 104.3g (1 mol) of 35% hydrochloric acid is added into the 500ml reaction bottle to react for 110min at 95 ℃, the temperature is reduced to room temperature for crystallization and filtration, and a target product is obtained, and the yield is 75%.
Comparative example 3
43.5g (0.5 mol) of butanone oxime (C4H 9 NO), 70.8g (0.7 mol) of triethylamine (C6H 15N) and 1.1mol of tetrabutylammonium bromide are added into a 500ml reaction bottle, the temperature is raised to 60 ℃, 82g (0.65 mol) of dimethyl sulfate (C2H 6O 4S) is slowly dripped into the reaction bottle, the dripping time is 50min, the temperature is kept for 6H after the dripping is finished, the reaction liquid is transferred into the 500ml reaction bottle, 78.2g (0.75 mol) of 35 percent hydrochloric acid is added into the reaction bottle, the reaction is carried out for 120min at 100 ℃, the reaction liquid is cooled to room temperature, and crystallization and filtration are carried out to obtain the target product, wherein the yield is 82%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be subject to the appended claims.
Claims (3)
1. A preparation method of methoxylamine hydrochloride is characterized in that: the method comprises the following steps:
1) Butanone oxime (C) is added into the reaction vessel 4 H 9 NO), dimethyl sulfoxide (DMSO, C) 2 H 6 OS), triethylamine (C) 6 H 15 N) and methylating agent, temperature 15Reacting at the temperature of minus 75 ℃ to generate O-methyl-2-ketoxime ether;
2) Adding hydrochloric acid into the O-methyl-2-butanone oxime ether in the step 1 for acidification to obtain a target product, namely methoxylamine hydrochloride,
wherein butanone oxime (C) 4 H 9 NO) and triethylamine (C) 6 H 15 N) in a molar ratio of 1.3 to 1.5, dimethyl sulfoxide (DMSO, C) 2 H 6 OS) is 2.2 to 2.4 times of the molar weight of the butanone oxime;
the hydrochloric acid and butanone oxime (C) 4 H 9 NO) is 1:1-2:1.
2. The method for preparing methoxyamine hydrochloride according to claim 1, characterized in that: the reaction time in the step 1 is 6-10 h.
3. The process for the preparation of methoxyamine hydrochloride according to claim 1, characterized in that: butanone oxime (C) 4 H 9 NO) to methylating agent in a molar ratio of 1:1.1 to 1.4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911281544.9A CN110922341B (en) | 2019-12-15 | 2019-12-15 | Preparation method of methoxylamine hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911281544.9A CN110922341B (en) | 2019-12-15 | 2019-12-15 | Preparation method of methoxylamine hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110922341A CN110922341A (en) | 2020-03-27 |
| CN110922341B true CN110922341B (en) | 2023-04-14 |
Family
ID=69860457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911281544.9A Active CN110922341B (en) | 2019-12-15 | 2019-12-15 | Preparation method of methoxylamine hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110922341B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113735736A (en) * | 2021-07-06 | 2021-12-03 | 四平市精细化学品有限公司 | Method for synthesizing methoxyamine by using phloroglucinol as platform molecule |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101357895A (en) * | 2008-09-19 | 2009-02-04 | 江苏爱利思达清泉化学有限公司 | Method for synthesizing methoxamine hydrochloride |
| CN101503375A (en) * | 2009-03-16 | 2009-08-12 | 宁波欧迅化学新材料技术有限公司 | Method for synthesizing methoxy amine hydrochlorate |
| CN102325758A (en) * | 2008-12-23 | 2012-01-18 | 巴斯夫欧洲公司 | Imine compounds for combating invertebrate pests |
| CN102976968A (en) * | 2012-12-01 | 2013-03-20 | 张家港市大伟助剂有限公司 | Preparation method for methoxylamine hydrochloride |
| CN105330564A (en) * | 2015-11-20 | 2016-02-17 | 浙江华方药业股份有限公司 | Preparation method of methoxyamine hydrochloride |
-
2019
- 2019-12-15 CN CN201911281544.9A patent/CN110922341B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101357895A (en) * | 2008-09-19 | 2009-02-04 | 江苏爱利思达清泉化学有限公司 | Method for synthesizing methoxamine hydrochloride |
| CN102325758A (en) * | 2008-12-23 | 2012-01-18 | 巴斯夫欧洲公司 | Imine compounds for combating invertebrate pests |
| CN101503375A (en) * | 2009-03-16 | 2009-08-12 | 宁波欧迅化学新材料技术有限公司 | Method for synthesizing methoxy amine hydrochlorate |
| CN102976968A (en) * | 2012-12-01 | 2013-03-20 | 张家港市大伟助剂有限公司 | Preparation method for methoxylamine hydrochloride |
| CN105330564A (en) * | 2015-11-20 | 2016-02-17 | 浙江华方药业股份有限公司 | Preparation method of methoxyamine hydrochloride |
Non-Patent Citations (2)
| Title |
|---|
| 几种柠檬醛和樟脑肟醚类化合物的合成及其生物活性研究;莫洪波;《硕士学位论文》;20040601;正文第11页 * |
| 羟胺及烷氧基胺盐酸盐绿色生产工艺探索及实践;王伟 等;《山东化工》;20121231;第41卷(第2期);第1-4页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110922341A (en) | 2020-03-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108503531B (en) | Preparation method of 3, 3-dimethyl-2-oxobutyric acid | |
| CN110922341B (en) | Preparation method of methoxylamine hydrochloride | |
| CN109534975B (en) | A kind of catalytic synthesis method of 2-hydroxybenzophenone compounds | |
| CN104030886B (en) | Be the method that 2,2-difluoroethanol prepared by raw material with the fluoro-1-halothane of 2,2-bis- | |
| CN103755696B (en) | A kind of synthetic method of Nifuratel | |
| CN113874351B (en) | Synthesis method of florfenicol | |
| CN112010793B (en) | Synthetic method of 2-methylsulfonyl-4-trifluoromethylbenzoic acid | |
| CN111253241B (en) | 2,4,5-trifluoro-3-methoxybenzoyl chloride and preparation method of intermediate thereof | |
| CN102942532A (en) | Preparation method of 1,4,7,10-tetraazadodecane | |
| CN111018757A (en) | Method for synthesizing 3-mercaptopropionic acid by using acidic waste gas | |
| CN111004205A (en) | Synthetic method for preparing piperonyl butoxide under catalysis of composite alkali | |
| CN104892430A (en) | Method for clean preparation of alkyl substituted diamine fluorene compound | |
| CN101514190B (en) | Method for preparing heterocyclic compounds of methyl mercapto under ionic liquid catalysis | |
| CN112939804A (en) | Preparation method of organic amine oxide | |
| CN101774945A (en) | Method for synthesizing 4,4,4-trifluoro-butyronitrile | |
| CN101844989B (en) | Preparation method for clofedanol and hydrochloride thereof | |
| CN111333591A (en) | A kind of preparation method of 3-hydrazine-5-morpholinyl methyl-2-oxazolidinone | |
| CN101157679B (en) | Method for preparing N- ethyl-3,4-(methylenedioxy) aniline | |
| CN101337868A (en) | Method for preparing 3-phenoxy-benzaldehyde | |
| CN106478422A (en) | A kind of preparation method of paranitrophenylacetic acid | |
| CN112142579A (en) | Preparation process of 2-hydroxy-4-methoxybenzophenone | |
| CN106883147B (en) | A kind of preparation method of phenyl-pentafluoride formonitrile HCN | |
| CN1186124C (en) | Composite base catalyst and its preparing method | |
| CN103483199A (en) | Preparation method of tetrafluoroterephthalate | |
| CN109232471B (en) | Preparation method of pramipexole dihydrochloride |
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 |