CN104892484A - Synthesis method for N-phenylmaleimide - Google Patents
Synthesis method for N-phenylmaleimide Download PDFInfo
- Publication number
- CN104892484A CN104892484A CN201510322196.0A CN201510322196A CN104892484A CN 104892484 A CN104892484 A CN 104892484A CN 201510322196 A CN201510322196 A CN 201510322196A CN 104892484 A CN104892484 A CN 104892484A
- Authority
- CN
- China
- Prior art keywords
- phenylmaleimide
- reaction
- acid
- cyclodehydration
- synthetic method
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
The invention discloses a synthesis method for N-phenylmaleimide. The synthesis method comprises the steps of acylation synthesis, cyclodehydration and cooling crystallization and comprises the following specific steps: firstly, adding an aromatic solvent, an assistant solvent and a polymerization inhibitor in maleic anhydride in sequence and heating for reaction so as to obtain an intermediate N-phenyl maleimide acid, after cyclodehydration, cooling, washing and distilling under reduced pressure so as to obtain a N-phenylmaleimide crude product, dissolving through a methanol solution, filtering and carrying out cooling crystallization so as to obtain the N-phenylmaleimide finally. According to the invention, all chemical reactions are completed in one reactor, the intermediate product is not required to be filtered in a suction manner, dried and fed again, and the whole reaction is carried out under a homogeneous-phase condition, so that the reaction speed is increased and the reaction period is shortened. The yield of the process can reach 90% or above, the purity can reach 96% or above, the synthesis process is stable and safe, less side reaction is realized, product quality is stable, the production cost is low and the synthesis method is completely suitable for scale industrial production and is easy to popularize and apply.
Description
Technical field
The invention belongs to synthesis technical field, be specifically related to a kind of synthetic method of N-phenylmaleimide.
Background technology
N-phenylmaleimide is a kind of emerging heat-resistant monomer, because it has five-membered cyclic two dimensional structure, is widely used as the thermotolerance improving polymkeric substance.The heat resisting temperature of ABS resin can be made in the application of ABS resin to reach 125 ~ 130 DEG C, the super heat-resisting ABS resin that other property retentions are constant can also be produced, can Some substitute engineering plastics in application, it is a kind of heat-proof modifier conventional in current production of resins, in view of the resistance toheat that N-phenylmaleimide is superpower, increasing research and development institution is all being devoted to the research to N-phenylmaleimide.At present, the preparation method of N-phenylmaleimide mainly adopts MALEIC ANHYDRIDE and aniline to react under the effect of catalyzer and generates the acid of intermediate N phenyl maleimide, and this intermediate is obtained by reacting target product N-phenylmaleimide by cyclodehydration again.In the patent No. in the patent of invention disclosed in 201210112725.0, describe MALEIC ANHYDRIDE after terminating with aniline building-up reactions, need just can obtain N-phenylmaleimide after acid-base neutralisation, layering, washing, crystallisation by cooling, its complex operation step, reaction time is longer, the amount of industrial wastewater produced is large, and difficult.Also have in Chinese periodical " elastomerics " 2005 15 volumes the 3rd phase 34-36 page " synthesis of N-phenylmaleimide " and report two step synthesis N-phenylmaleimide, this method is after the first step is obtained by reacting the acid of intermediate N phenyl maleimide, this intermediate suction filtration is also dry, raw material as the reaction of second step cyclodehydration uses, the method is complex operation step not only, and loss of material is serious, finally cause product yield lower, cost of investment increases, in addition, when adding catalyzer, the overwhelming majority employs tosic acid and N-ethyl pyrrolidone as dual catalytic agent, the carrying out of catalytic dehydration cyclization, make the large usage quantity of N-ethyl pyrrolidone, and it is expensive, virtually just increase production cost.Therefore, develop that a kind of operating procedure is simple, yield is high, product purity is high and steady quality, reaction time are short, energy-conserving and environment-protective, the synthetic method that is applicable to the N-phenylmaleimide of large-scale production are desirabilities.
Summary of the invention
In order to solve Problems existing in background technology, the object of the present invention is to provide that a kind of operating procedure is simple, yield is high, product purity is high and steady quality, reaction time are short, energy-conserving and environment-protective, be applicable to the synthetic method of the N-phenylmaleimide of large-scale production.
The object of the present invention is achieved like this, a kind of synthetic method of N-phenylmaleimide, and comprise acidylate synthesis, cyclodehydration and crystallisation by cooling, concrete synthesis step is as follows:
acidylate is synthesized: in the container that MALEIC ANHYDRIDE is housed, add aromatic solvent, solubility promoter and stopper successively under room temperature, after stirring, control temperature is below 30 DEG C, and in 20 ~ 30min, instill aniline carry out acylation reaction, heat up after dropwising, when being warming up to 50 ~ 70 DEG C, reaction 0.5 ~ 1h, obtains the acid of intermediate product N-phenylmaleimide;
cyclodehydration: by step
obtained N-phenylmaleimide acid continues to heat up, add catalyzer, cyclodehydration is carried out under aromatic hydrocarbon reflux state, the time of cyclization is 3 ~ 5h, and the temperature of cyclization is 110 ~ 125 DEG C, after reaction to be drained off terminates, be cooled to less than 70 DEG C, with the water deviate from reaction, reaction solution is washed, carry out underpressure distillation Arene removal solvent after washing, obtain N-phenylmaleimide crude product;
crystallisation by cooling: by step
the yellow needle-like crystals that the N-phenylmaleimide crude product methanol solution obtained carries out dissolving, filter, separate out after crystallisation by cooling is N-phenylmaleimide.
The present invention adopts one kettle way Homogeneous synthesis N-phenylmaleimide, the acid of intermediate product N-phenylmaleimide is gone out without the need to suction filtration in the process of operation, not only reduce operation steps, avoid loss of material, for high yield is laid a good foundation, and utilize the method adding solubility promoter that reaction can be enable to carry out under homogeneous phase condition, can control speed of response accurately, the efficiency of reaction have also been obtained and increases substantially.Simultaneously, in water-washing step, react from cyclodehydration the water removed at the water source of washed reaction liquid, not only achieve the recycling of resource, solve the problem of wastewater treatment difficulty, and the solubility promoter added also can recycling, reduces the cost of investment of solubility promoter, reduces environmental stress.The present invention is in whole building-up process; production cost is low; the yield of product is high, purity is high, side reaction is few; the steady quality of product; its yield can reach more than 90%, and purity can reach more than 96%, and building-up process is stable, safety; be applicable to the industrial production of mass-producing completely, be easy to promote the use of.
Embodiment
Below in conjunction with embodiment, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or replacement, all belong to protection scope of the present invention.
Embodiment 1:
A synthetic method for N-phenylmaleimide, comprise acidylate synthesis, cyclodehydration and crystallisation by cooling, concrete synthesis step is as follows:
acidylate is synthesized: under room temperature 1000mL container in add the MALEIC ANHYDRIDE of 0.5mol, 1.5g Resorcinol, the toluene of 400mL and the mixed solvent of dimethylbenzene, the N of 10mL, dinethylformamide, after stirring, control temperature is below 30 DEG C, and the aniline instilling 45.6mL in 20min carries out acylation reaction, heat up after dropwising, when being warming up to 50 DEG C, reaction 0.5h, obtains the acid of intermediate product N-phenylmaleimide;
cyclodehydration: by step
obtained N-phenylmaleimide acid continues to heat up, add 7g tosic acid, cyclodehydration is carried out under aromatic hydrocarbon reflux state, the time of cyclization is 5h, and the temperature of cyclization is 125 DEG C, after reaction to be drained off terminates, be cooled to less than 70 DEG C, with the water deviate from reaction, reaction solution is washed, carry out underpressure distillation Arene removal solvent after washing, obtain N-phenylmaleimide crude product;
crystallisation by cooling: by step
the yellow needle-like crystals that the N-phenyl maleimide crude product methanol solution obtained carries out dissolving, filter, separate out after crystallisation by cooling is N-phenylmaleimide.
The processing step of the present embodiment 1 is simple, in whole building-up process, safety, efficiency that is stable, reaction time usage quantity that is short, solubility promoter that is high, reaction are little, the yield of product is high, purity is high, side reaction is few, the steady quality of product, its yield can reach 93.87%, and purity can reach 98.57%.
Embodiment 2:
A synthetic method for N-phenylmaleimide, comprise acidylate synthesis, cyclodehydration and crystallisation by cooling, concrete synthesis step is as follows:
acidylate is synthesized: in the container of 1000mL, add MALEIC ANHYDRIDE 0.5mol under room temperature, 1.5g Resorcinol and methyl hydroquinone, the toluene of 400mL and the mixed solvent of dimethylbenzene, the ethylene glycol of 10mL, after stirring, control temperature is below 30 DEG C, and the aniline instilling 45.6mL in 25min carries out acylation reaction, heats up after dropwising, when being warming up to 60 DEG C, reaction 0.8h, obtains the acid of intermediate product N-phenylmaleimide;
cyclodehydration: by step
obtained N-phenylmaleimide acid continues to heat up, add 7g tosic acid and phosphoric acid, cyclodehydration is carried out under aromatic hydrocarbon reflux state, the time of cyclization is 4h, and the temperature of cyclization is 125 DEG C, after reaction to be drained off terminates, be cooled to less than 70 DEG C, with the water deviate from reaction, reaction solution is washed, carry out underpressure distillation Arene removal solvent after washing, obtain N-phenylmaleimide crude product;
crystallisation by cooling: by step
the yellow needle-like crystals that the N-phenylmaleimide crude product methanol solution obtained carries out dissolving, filter, separate out after crystallisation by cooling is N-phenylmaleimide.
The processing step of the present embodiment 2 is simple, in whole building-up process, safety, efficiency that is stable, reaction time usage quantity that is short, solubility promoter that is high, reaction are little, the yield of product is high, purity is high, side reaction is few, the steady quality of product, its yield can reach 91.5%, and purity can reach 96.31%.
embodiment 3:
A synthetic method for N-phenylmaleimide, comprise acidylate synthesis, cyclodehydration and crystallisation by cooling, concrete synthesis step is as follows:
acidylate is synthesized: in the container of 1000mL, add MALEIC ANHYDRIDE 0.5mol under room temperature, 1.5g p-ten.-butylcatechol and methyl hydroquinone, the toluene of 400mL and the mixed solvent of dimethylbenzene, the methylene dichloride of 10mL, after stirring, control temperature is below 30 DEG C, and the aniline instilling 45.6mL in 30min carries out acylation reaction, heats up after dropwising, when being warming up to 70 DEG C, reaction 1h, obtains the acid of intermediate product N-phenylmaleimide;
cyclodehydration: by step
obtained N-phenylmaleimide acid continues to heat up, add the mixture of 7g tosic acid, phosphoric acid and phosphoric acid and phospho-wolframic acid, cyclodehydration is carried out under aromatic hydrocarbon reflux state, the time of cyclization is 5h, and the temperature of cyclization is 125 DEG C, after reaction to be drained off terminates, be cooled to less than 70 DEG C, with the water deviate from reaction, reaction solution is washed, carry out underpressure distillation Arene removal solvent after washing, obtain N-phenylmaleimide crude product;
crystallisation by cooling: by step
the yellow needle-like crystals that the N-phenylmaleimide crude product methanol solution obtained carries out dissolving, filter, separate out after crystallisation by cooling is N-phenylmaleimide.
The processing step of the present embodiment 3 is simple, in whole building-up process, safety, efficiency that is stable, reaction time usage quantity that is short, solubility promoter that is high, reaction are little, the yield of product is high, purity is high, side reaction is few, the steady quality of product, its yield can reach 90.64%, and purity can reach 97.33%.
Claims (6)
1. a synthetic method for N-phenylmaleimide, comprise acidylate synthesis, cyclodehydration and crystallisation by cooling, concrete synthesis step is as follows:
acidylate is synthesized: in the container that MALEIC ANHYDRIDE is housed, add aromatic solvent, solubility promoter and stopper successively under room temperature, after stirring, control temperature is below 30 DEG C, and in 20 ~ 30min, instill aniline carry out acylation reaction, heat up after dropwising, when being warming up to 50 ~ 70 DEG C, reaction 0.5 ~ 1h, obtains the acid of intermediate product N-phenyl maleimide;
cyclodehydration: by step
obtained N-phenylmaleimide acid continues to heat up, add catalyzer, cyclodehydration reaction is carried out under aromatic hydrocarbon reflux state, the time of cyclization is 3 ~ 5h, and the temperature of cyclization is 110 ~ 125 DEG C, after reaction to be drained off terminates, be cooled to less than 70 DEG C, with the water deviate from reaction, reaction solution is washed, after carry out underpressure distillation Arene removal solvent, obtain N-phenylmaleimide crude product;
crystallisation by cooling: by step
the yellow needle-like crystals that the N-phenylmaleimide crude product methanol solution obtained carries out dissolving, filter, separate out after crystallisation by cooling is N-phenylmaleimide.
2. the synthetic method of a kind of N-phenylmaleimide according to claim 1, is characterized in that: step
described in MALEIC ANHYDRIDE and the mol ratio of aniline be 1 ~ 1.2:1.
3. the synthetic method of a kind of N-phenylmaleimide according to claim 1, is characterized in that: step
described in catalyzer be one or more in the mixture of phosphoric acid, phospho-wolframic acid, phosphoric acid and phospho-wolframic acid, tosic acid or 2,5-acid dimethyl, the mol ratio of described catalyzer is 2% ~ 3% of MALEIC ANHYDRIDE mol ratio.
4. the synthetic method of a kind of N-phenylmaleimide according to claim 1, is characterized in that: step
described in aromatic solvent be the mixed solvent of toluene and dimethylbenzene, described aromatic solvent is 3 ~ 6mL/g with the volume mass ratio of MALEIC ANHYDRIDE.
5. the synthetic method of a kind of N-phenylmaleimide according to claim 1, is characterized in that: step
described stopper comprises methyl hydroquinone, p-ten.-butylcatechol or Resorcinol, and the consumption of described stopper is 2% ~ 3% of MALEIC ANHYDRIDE quality.
6. the synthetic method of a kind of N-phenylmaleimide according to claim 1, is characterized in that: step
described solubility promoter comprises methylene dichloride, acetone, DMF or ethylene glycol, and described aromatic solvent and solubility promoter volume ratio are 30 ~ 50:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510322196.0A CN104892484A (en) | 2015-06-12 | 2015-06-12 | Synthesis method for N-phenylmaleimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510322196.0A CN104892484A (en) | 2015-06-12 | 2015-06-12 | Synthesis method for N-phenylmaleimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104892484A true CN104892484A (en) | 2015-09-09 |
Family
ID=54025504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510322196.0A Pending CN104892484A (en) | 2015-06-12 | 2015-06-12 | Synthesis method for N-phenylmaleimide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104892484A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859724A (en) * | 2016-04-29 | 2016-08-17 | 绍兴文理学院 | 3-(6-bromo-4-oxy-4H-chromone)-1-phenyl-5-p-chlorphenyl-1,6a-dihydro pyrroline[3,4-c] pyrazole-4,6(3aH,5H)-diketone and preparation method and application thereof |
| CN105906632A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | Pyrazole-type N-p-methylphenyl maleimide derivative with chromone structure, and preparation method and application thereof |
| CN105906633A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | Pyrazole-type N-phenyl maleimide derivative with chromone structure, and preparation method and application thereof |
| CN105906634A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | 3-(6-bromine-4-oxygen-4H-chromone)-1-phenyl-5-p-methoxyphenyl-1, 6a-pyrroline (3, 4-c) pyrazole-4, 6(3aH, 5H)-diketone and preparation method and application thereof |
| CN105924445A (en) * | 2016-04-29 | 2016-09-07 | 绍兴文理学院 | Pyrazole-type N-p-nitrophenyl maleimide derivative containing chromone structure, and preparation method and application thereof |
| CN106397445A (en) * | 2016-04-29 | 2017-02-15 | 绍兴文理学院 | Pyrazoles N-p-bromophenyl maleimide derivative containing chromone structure as well as preparation method and application thereof |
| CN113231069A (en) * | 2021-04-15 | 2021-08-10 | 云南大为恒远化工有限公司 | Composite efficient catalyst for preparing succinic anhydride by maleic anhydride body hydrogenation and preparation method thereof |
| CN115197116A (en) * | 2021-04-12 | 2022-10-18 | 中国石油化工股份有限公司 | Preparation method of N-phenylmaleimide |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1962634A (en) * | 2006-12-01 | 2007-05-16 | 浙江大学 | Process for preparing N-phenyl maleimide |
| CN101462997A (en) * | 2008-12-30 | 2009-06-24 | 上海华谊（集团）公司 | Preparation of N-phenyl maleimide |
| CN103664732A (en) * | 2013-12-26 | 2014-03-26 | 上海华谊（集团）公司 | Synthetic method of N-phenylmaleimide |
| CN104557657A (en) * | 2013-10-09 | 2015-04-29 | 中国石油化工股份有限公司 | One-step synthesis method of N-phenylmaleimide |
-
2015
- 2015-06-12 CN CN201510322196.0A patent/CN104892484A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1962634A (en) * | 2006-12-01 | 2007-05-16 | 浙江大学 | Process for preparing N-phenyl maleimide |
| CN101462997A (en) * | 2008-12-30 | 2009-06-24 | 上海华谊（集团）公司 | Preparation of N-phenyl maleimide |
| CN104557657A (en) * | 2013-10-09 | 2015-04-29 | 中国石油化工股份有限公司 | One-step synthesis method of N-phenylmaleimide |
| CN103664732A (en) * | 2013-12-26 | 2014-03-26 | 上海华谊（集团）公司 | Synthetic method of N-phenylmaleimide |
Non-Patent Citations (7)
| Title |
|---|
| 史法胜: "N-苯基马来酰亚胺的合成研究", 《山东化工》 * |
| 张德江等: "N-苯基马来酰亚胺的合成", 《弹性体》 * |
| 彭永利: "N-苯基马来酰亚胺的合成及应用研究", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 彭永利等: "N-苯基马来酰亚胺的合成研究", 《化学与生物工程》 * |
| 王宝丰等: "N-苯基马来酰亚胺合成工艺的研究", 《天津化工》 * |
| 贾海红等: "N-苯基马来酰亚胺的合成及应用进展", 《热固性树脂》 * |
| 赵英武: "N-苯基马来酰亚胺的合成方法、应用及市场展望", 《化工技术与开发》 * |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105924445B (en) * | 2016-04-29 | 2017-12-12 | 绍兴文理学院 | Pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure and preparation method and application |
| CN105906634B (en) * | 2016-04-29 | 2017-12-12 | 绍兴文理学院 | P-methoxyphenyl 1,6a pyrrolin quinoline [3,4 c] pyrazoles 4,6 (3aH, 5H) diketone of 3 (the oxygen 4H chromones of 6 bromine 4) 1 phenyl 5 and preparation method and application |
| CN105906633A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | Pyrazole-type N-phenyl maleimide derivative with chromone structure, and preparation method and application thereof |
| CN105906634A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | 3-(6-bromine-4-oxygen-4H-chromone)-1-phenyl-5-p-methoxyphenyl-1, 6a-pyrroline (3, 4-c) pyrazole-4, 6(3aH, 5H)-diketone and preparation method and application thereof |
| CN105859724A (en) * | 2016-04-29 | 2016-08-17 | 绍兴文理学院 | 3-(6-bromo-4-oxy-4H-chromone)-1-phenyl-5-p-chlorphenyl-1,6a-dihydro pyrroline[3,4-c] pyrazole-4,6(3aH,5H)-diketone and preparation method and application thereof |
| CN106397445A (en) * | 2016-04-29 | 2017-02-15 | 绍兴文理学院 | Pyrazoles N-p-bromophenyl maleimide derivative containing chromone structure as well as preparation method and application thereof |
| CN105906632A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | Pyrazole-type N-p-methylphenyl maleimide derivative with chromone structure, and preparation method and application thereof |
| CN105859724B (en) * | 2016-04-29 | 2017-12-12 | 绍兴文理学院 | Rubigan 1,6a pyrrolin quinoline [3,4 c] pyrazoles 4,6 (3aH, 5H) diketone of 3 (the oxygen 4H chromones of 6 bromine 4) 1 phenyl 5 and preparation method and application |
| CN105924445A (en) * | 2016-04-29 | 2016-09-07 | 绍兴文理学院 | Pyrazole-type N-p-nitrophenyl maleimide derivative containing chromone structure, and preparation method and application thereof |
| CN105906633B (en) * | 2016-04-29 | 2018-01-02 | 绍兴文理学院 | Pyrazoles N phenyl maleimide derivatives containing chromone structure and preparation method and application |
| CN106397445B (en) * | 2016-04-29 | 2018-05-29 | 绍兴文理学院 | Pyrazoles N- p-bromophenyl maleimide derivatives containing chromone structure and preparation method and application |
| CN105906632B (en) * | 2016-04-29 | 2018-05-29 | 绍兴文理学院 | Pyrazoles N- p-methylphenyl maleimide derivatives containing chromone structure and preparation method and application |
| CN115197116A (en) * | 2021-04-12 | 2022-10-18 | 中国石油化工股份有限公司 | Preparation method of N-phenylmaleimide |
| CN115197116B (en) * | 2021-04-12 | 2024-05-14 | 中国石油化工股份有限公司 | Preparation method of N-phenylmaleimide |
| CN113231069A (en) * | 2021-04-15 | 2021-08-10 | 云南大为恒远化工有限公司 | Composite efficient catalyst for preparing succinic anhydride by maleic anhydride body hydrogenation and preparation method thereof |
| CN113231069B (en) * | 2021-04-15 | 2024-02-06 | 云南大为恒远化工有限公司 | Maleic anhydride bulk hydrogenation succinic anhydride preparation composite efficient catalyst and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104892484A (en) | Synthesis method for N-phenylmaleimide | |
| CN103664709B (en) | A kind of production method of 2-acrylamide-2-methylpro panesulfonic acid | |
| CN103664732A (en) | Synthetic method of N-phenylmaleimide | |
| CN107337618B (en) | Production method for simultaneously improving purity and yield of metformin hydrochloride | |
| CN106008482B (en) | A method of preparing electron level triglycidyl isocyanurate | |
| CN105968032A (en) | Synthetic method of metformin hydrochloride | |
| CN106928116A (en) | 2,2 ' double ［ 4（4 maleimide phenoxyls）Phenyl ］ propane preparation method | |
| CN103450131B (en) | The preparation method of a kind of dehydroacetic acid (DHA) and sodium salt thereof | |
| CN103497142B (en) | The preparation method of Disperse Blue-60 and/or its homologue | |
| CN102659587A (en) | Method for refining adamantane methacrylate | |
| CN102942543B (en) | Preparation method for 3-(Alpha-methoxy)methylenebenzofuran-2(3h)-one | |
| CN105503513A (en) | Method for catalytically synthesizing 4,4'-bischloromethylbiphenyl by using silicon dioxide-loaded phosphotungstic acid | |
| CN106187741B (en) | A kind of preparation method of the iodo- l,2,3 benzene tricarboxylic acids of 5- | |
| CN102633706A (en) | Synthesis method of N-phenyl-maleimide | |
| CN104402745A (en) | Method for synthesizing isopropyl 3-aminocrotonate | |
| CN102942533B (en) | Preparation method of 4-(5-amino-6-hydroxy-2-benzoxazolyl) benzoic acid (ABA) | |
| CN103012087B (en) | Green synthetic method of alpha, alpha'-double benzylidene cycloalkanone compound | |
| CN102531993A (en) | Synthetic method of N, N'-m-phenylenedimaleimide | |
| CN106397188A (en) | Preparation method of L-chicoric acid | |
| CN112047851A (en) | Preparation method of D-panthenol | |
| CN105541611A (en) | Method for preparing aceto acetoxy ethyl methacrylate | |
| CN104529862B (en) | N,N'-m-phenylenedimaleimide and preparation method thereof | |
| CN108191705A (en) | A kind of method for preparing acethydrazide | |
| CN113801125B (en) | Preparation method of cyclic anhydride | |
| CN1775775A (en) | Method for preparing dimaleimide compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150909 |