CN104892386A - Synthesis method of 2-heptamethylene cyclopentanone - Google Patents
Synthesis method of 2-heptamethylene cyclopentanone Download PDFInfo
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- CN104892386A CN104892386A CN201510271454.7A CN201510271454A CN104892386A CN 104892386 A CN104892386 A CN 104892386A CN 201510271454 A CN201510271454 A CN 201510271454A CN 104892386 A CN104892386 A CN 104892386A
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- cyclopentanone
- fleuramone
- sub
- synthetic method
- sodium hydroxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of 2-heptamethylene cyclopentanone, which comprises the following steps: reacting cyclopentanone and n-heptyl aldehyde at 70-90 DEG C under the action of a catalyst for 8-10 hours, regulating the pH value to 6-7, adding toluene, stirring at 100-120 DEG C until no water is generated, washing and drying to obtain the finished product. The sodium hydroxide catalyst can be utilized to control the progress and selectivity of the reaction, thereby enhancing the atom utilization ratio of the reactants and achieving the high yield of the aldol condensation reaction.
Description
Technical field
The application belongs to chemical technology field, particularly relates to the synthetic method of the sub-fleuramone of a kind of 2-.
Background technology
Aldol reaction is that the compound containing α-hydrogen atom such as ketone, aldehyde, carboxylic acid etc. carry out nucleophilic addition, and condensation obtains beta-hydroxy ketone or aldehyde under acidity or basic catalyst effect.
Traditional aldol reaction has following deficiency:
(1), stereoselectivity and regioselectivity performance lower;
(2), dehydration reaction stop after, α, β-unsaturated compound still can generate oligopolymer or polymer further;
(3), can multiple reaction be caused, cause cross-couplings to carry out difficulty.
Summary of the invention
The object of the present invention is to provide the synthetic method of the sub-fleuramone of a kind of 2-, to overcome deficiency of the prior art.
For achieving the above object, the invention provides following technical scheme:
The embodiment of the present application discloses the synthetic method of the sub-fleuramone of a kind of 2-, under catalyst action, cyclopentanone and enanthaldehyde react 8 ~ 10 hours under 70 ~ 90 DEG C of conditions, pH value is regulated to be 6 ~ 7, add toluene, stir until no longer include water generation 100 ~ 120 DEG C of conditions, obtain finished product finally by washing and drying.
Preferably, in the synthetic method of the sub-fleuramone of above-mentioned 2-, described catalyzer is sodium hydroxide.
Preferably, in the synthetic method of the sub-fleuramone of above-mentioned 2-, described amount of sodium hydroxide is 7% ~ 11% of cyclopentanone quality.
Preferably, in the synthetic method of the sub-fleuramone of above-mentioned 2-, the concentration of described sodium hydroxide is 2% ~ 2.3%.
Preferably, in the synthetic method of the sub-fleuramone of above-mentioned 2-, the mol ratio of described cyclopentanone and enanthaldehyde is (1 ~ 1.3): 1.
Compared with prior art, the invention has the advantages that: the present invention can control process and the selectivity of reaction by sodium hydroxide catalyst, improves reactant atom utilization, allows aldol reaction reach efficient productive rate.
Embodiment
The present invention is described further by the following example: according to following embodiment, the present invention may be better understood.But those skilled in the art will readily understand, concrete material ratio, processing condition and result thereof described by embodiment only for illustration of the present invention, and should can not limit the present invention described in detail in claims yet.
Embodiment 1
Cyclopentanone 2.1g, enanthaldehyde 2.19g are joined in flask, sodium hydroxide catalyst is added in whipping process, the quality of sodium hydroxide is 10% of cyclopentanone, 85 DEG C of conditioned responses 10 hours, adding hydrochloric acid after reaction terminates regulates PH to be about 6, to fetch water layer with toluene, then with sodium hydrogen carbonate solution and sodium chloride solution washing, a certain amount of toluene is added in solution after washing, stir until no longer include water generation under about 110 DEG C, after cooling, continuation sodium hydrogen carbonate solution and sodium chloride solution washing, underpressure distillation, drying, obtain finished product.
Pillar layer separation and nuclear-magnetism sign are carried out to above-mentioned finished product, known: finished product purity is more than 98%, and transformation efficiency is more than 80%, and productive rate is more than 60%.
Embodiment 2
Cyclopentanone and enanthaldehyde are joined in flask according to 1.2:1 mol ratio, sodium hydroxide catalyst is added in whipping process, the quality of sodium hydroxide is 11% of cyclopentanone, 85 DEG C of conditioned responses 10 hours, adding hydrochloric acid after reaction terminates regulates PH to be about 6, to fetch water layer with toluene, then with sodium hydrogen carbonate solution and sodium chloride solution washing, a certain amount of toluene is added in solution after washing, stir until no longer include water generation under about 110 DEG C, after cooling, continuation sodium hydrogen carbonate solution and sodium chloride solution washing, underpressure distillation, dry, obtain finished product.
Pillar layer separation and nuclear-magnetism sign are carried out to above-mentioned finished product, known: finished product purity is more than 98%, and transformation efficiency is more than 80%, and productive rate is more than 60%.
Embodiment 3
Cyclopentanone and enanthaldehyde are joined in flask according to 1.3:1 mol ratio, sodium hydroxide catalyst is added in whipping process, the quality of sodium hydroxide is 10% of cyclopentanone, 85 DEG C of conditioned responses 10 hours, adding hydrochloric acid after reaction terminates regulates PH to be about 6, to fetch water layer with toluene, then with sodium hydrogen carbonate solution and sodium chloride solution washing, a certain amount of toluene is added in solution after washing, stir until no longer include water generation under about 110 DEG C, after cooling, continuation sodium hydrogen carbonate solution and sodium chloride solution washing, underpressure distillation, dry, obtain finished product.
Pillar layer separation and nuclear-magnetism sign are carried out to above-mentioned finished product, known: finished product purity is more than 98%, and transformation efficiency is more than 80%, and productive rate is more than 60%.
Comparative example
Cyclopentanone and enanthaldehyde are joined in flask according to 1.3:1 mol ratio, concentrated sulfuric acid catalyst is added in whipping process, 85 DEG C of conditioned responses 10 hours, adding hydrochloric acid after reaction terminates regulates PH to be about 6, to fetch water layer with toluene, then with sodium hydrogen carbonate solution and sodium chloride solution washing, a certain amount of toluene is added in solution after washing, stir until no longer include water generation under about 110 DEG C, after cooling, continuation sodium hydrogen carbonate solution and sodium chloride solution washing, underpressure distillation, drying, obtain finished product.
Pillar layer separation and nuclear-magnetism sign are carried out to above-mentioned finished product, known: low conversion rate is in 35%, and productive rate is lower than 10%.
Finally, also it should be noted that, term " comprises ", " comprising " or its any other variant are intended to contain comprising of nonexcludability, thus make to comprise the process of a series of key element, method, article or equipment and not only comprise those key elements, but also comprise other key elements clearly do not listed, or also comprise by the intrinsic key element of this process, method, article or equipment.
Claims (5)
1. the synthetic method of the sub-fleuramone of 2-, it is characterized in that: under catalyst action, cyclopentanone and enanthaldehyde react 8 ~ 10 hours under 70 ~ 90 DEG C of conditions, pH value is regulated to be 6 ~ 7, add toluene, stir until no longer include water generation 100 ~ 120 DEG C of conditions, obtain finished product finally by washing and drying.
2. the synthetic method of the sub-fleuramone of 2-according to claim 1, is characterized in that: described catalyzer is sodium hydroxide.
3. the synthetic method of the sub-fleuramone of 2-according to claim 2, is characterized in that: described amount of sodium hydroxide is 7% ~ 11% of cyclopentanone quality.
4. the synthetic method of the sub-fleuramone of 2-according to claim 2, is characterized in that: the concentration of described sodium hydroxide is 2% ~ 2.3%.
5. the synthetic method of the sub-fleuramone of 2-according to claim 1, is characterized in that: the mol ratio of described cyclopentanone and enanthaldehyde is (1 ~ 1.3): 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510271454.7A CN104892386A (en) | 2015-05-25 | 2015-05-25 | Synthesis method of 2-heptamethylene cyclopentanone |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510271454.7A CN104892386A (en) | 2015-05-25 | 2015-05-25 | Synthesis method of 2-heptamethylene cyclopentanone |
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| CN201510271454.7A Pending CN104892386A (en) | 2015-05-25 | 2015-05-25 | Synthesis method of 2-heptamethylene cyclopentanone |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030109755A1 (en) * | 2001-11-30 | 2003-06-12 | Takasago International Corporation | Process for producing 2-alkyl-2cyclopentenones |
| CN101851154A (en) * | 2010-05-18 | 2010-10-06 | 天津理工大学 | Improved method for producing 2-alkylene alicyclic ketone |
| CN102382089A (en) * | 2011-11-08 | 2012-03-21 | 安徽理工大学 | Method for synthesizing delta-dodecalactone |
| CN102503791A (en) * | 2011-11-25 | 2012-06-20 | 天津理工大学 | Method for producing 2-alkylene grease cyclic ketone by adopting bionic catalytic system |
-
2015
- 2015-05-25 CN CN201510271454.7A patent/CN104892386A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030109755A1 (en) * | 2001-11-30 | 2003-06-12 | Takasago International Corporation | Process for producing 2-alkyl-2cyclopentenones |
| CN101851154A (en) * | 2010-05-18 | 2010-10-06 | 天津理工大学 | Improved method for producing 2-alkylene alicyclic ketone |
| CN102382089A (en) * | 2011-11-08 | 2012-03-21 | 安徽理工大学 | Method for synthesizing delta-dodecalactone |
| CN102503791A (en) * | 2011-11-25 | 2012-06-20 | 天津理工大学 | Method for producing 2-alkylene grease cyclic ketone by adopting bionic catalytic system |
Non-Patent Citations (1)
| Title |
|---|
| 徐金峰等: "δ-癸内酯和δ-十二内酯的合成", 《精细与专用化学品》 * |
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Application publication date: 20150909 |