CN114380674B - Preparation method of 1, 3-cyclohexanedione - Google Patents
Preparation method of 1, 3-cyclohexanedione Download PDFInfo
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- CN114380674B CN114380674B CN202210279237.2A CN202210279237A CN114380674B CN 114380674 B CN114380674 B CN 114380674B CN 202210279237 A CN202210279237 A CN 202210279237A CN 114380674 B CN114380674 B CN 114380674B
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- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
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Abstract
The invention discloses a preparation method of 1, 3-cyclohexanedione, belonging to the technical field of chemical synthesis, wherein n reaction kettles are connected in series in a multi-kettle series connection mode, sodium methoxide, sodium hydroxide, metal sodium and an aprotic polar solvent are added into a first-stage reaction kettle, and 5-oxomethyl caproate is respectively added into the 1 st-n-1 st-stage reaction kettle; n is 3 to 8; the preparation method selects raw materials and mixed alkali with lower cost, performs reaction in a multi-kettle series connection mode, prepares the high-content 1, 3-cyclohexanedione through acidification, centrifugation and drying, and has the advantages of mild reaction conditions, high reaction selectivity, high yield and purity, less side reaction, high content and low cost.
Description
Technical Field
The invention relates to a synthesis process of 1, 3-cyclohexanedione, and belongs to the technical field of chemical synthesis.
Background
The 1, 3-cyclohexanedione is an important organic synthesis intermediate, is widely applied to synthesis of pesticide raw materials, such as mesotrione, tembotrione and the like, and is also applied to the pharmaceutical industry for preparing and synthesizing special-effect medicines, namely carvedilol and antiemetic anthracenedione for protecting heart and cerebral vessels and treating hypertension.
At present, 1, 3-cyclohexanedione is mainly a resorcinol hydrogenation reduction method, a noble metal catalyst is needed in the method, a large amount of liquid alkali is needed to be added in the process, finally, a large amount of waste salt is obtained, more waste materials need to be treated, and the problem is brought to the ecological environment. Therefore, the development of a new preparation method of 1, 3-cyclohexanedione can reduce the waste, reduce the side reaction and improve the purity of the prepared 1, 3-cyclohexanedione, and is a problem to be continuously solved at present.
Chinese patent CN103936559B discloses that resorcinol is produced continuously by three steps of nitration of benzene, hydrogenation reduction of dinitrobenzene and hydrolysis reaction of m-phenylenediamine with benzene as the starting material, and the waste generated in the reaction process is large.
Chinese patent CN113336629A discloses the use of acetylacetone as a raw material for preparing 1, 3-cyclohexanedione, which has high price of the raw material and does not have economic advantages.
Chinese patent CN113372192A discloses a synthesis method of low-carbon sodium alkoxide, which needs to continuously introduce hydrogen into a system, maintains the pressure of the reaction system at 0.5-1.8MPa, and has high requirements on equipment materials.
Disclosure of Invention
Aiming at the technical problems, the invention provides a synthesis process of 1, 3-cyclohexanedione, which selects raw materials and mixed alkali with lower cost, performs reaction in a multi-kettle series connection mode, and realizes high purity of products through a continuous production process and stable process conditions. The high-content 1, 3-cyclohexanedione is prepared by acidification, centrifugation and drying, and has the advantages of mild reaction conditions, high reaction selectivity, high yield and purity, less side reaction, high content and low cost.
The invention is realized by the following technical scheme:
a method for preparing 1, 3-cyclohexanedione comprises the steps of connecting n reaction kettles in series in a multi-kettle series mode, adding sodium methoxide, sodium hydroxide, metal sodium and an aprotic polar solvent into a first-stage reaction kettle, and respectively adding methyl 5-oxohexanoate into the 1 st to n-1 st-stage reaction kettles;
and n is 3-8.
The adding amount of the 5-oxo methyl hexanoate in the multi-kettle series connection in the 1 to n-1-stage reaction kettles is 10-50% of the total input amount, and the last stage reaction kettle is a curing kettle used for completely reacting the reaction materials without feeding operation.
The temperature of each stage of reaction kettle is controlled at 50-100 ℃, and the reaction time is 0.3-2 h.
In the reaction process, materials in the first-stage reaction kettle overflow to the second-stage reaction kettle, the materials in the second-stage reaction kettle overflow to the third-stage reaction kettle after being full, overflow is performed in sequence, qualified 1, 3-cyclohexanedione sodium salt is collected in the last-stage reaction kettle after overflowing to the last-stage reaction kettle for full reaction, and the product 1, 3-cyclohexanedione is obtained through acidification, centrifugation and drying.
Wherein the mass ratio of sodium methoxide, sodium hydroxide and metal sodium is 1 (0.5-1) to 0.1.
The aprotic polar solvent is one of tetrahydrofuran, acetonitrile, DMSO, DMAC, DMF and NMP.
The molar ratio of the sodium methoxide to the methyl 5-oxohexanoate is 0.1-0.4: 1.
The mass ratio of the aprotic polar solvent to the methyl 5-oxohexanoate is 1-10: 1.
The yield of the 1, 3-cyclohexanedione can reach 93.5-95%, and the purity can reach 99-99.5%.
The beneficial effects of the invention include the following:
(1) the synthesis process of the 1, 3-cyclohexanedione adopts a plurality of kettles connected in series, so that the production efficiency is obviously improved, the operation is simple and convenient, the side reaction is less, and the preparation of a high-content product is facilitated;
(2) the synthesis process of the 1, 3-cyclohexanedione adopts the 5-oxomethyl hexanoate and the mixed alkali with lower cost as raw materials, and has the advantage of low cost compared with the current mainstream process;
(3) the synthesis process of the 1, 3-cyclohexanedione does not relate to a pressure vessel, has low requirements on equipment materials, mild reaction conditions and less equipment investment;
(4) the synthesis process of the 1, 3-cyclohexanedione realizes continuous production by adopting a multi-kettle series connection mode, and solves the difficulty of low intermittent production efficiency of the product at present;
(5) according to the synthesis process of the 1, 3-cyclohexanedione, disclosed by the invention, the mixed alkali is used as the condensing agent, and the methanol generated in the reaction process is effectively utilized to generate the raw material sodium methoxide, so that the energy consumption for separating the methanol is saved, the using amount of the sodium methoxide is reduced, and the cost is saved;
(6) the synthesis process of the 1, 3-cyclohexanedione has the advantages that the yield of the prepared 1, 3-cyclohexanedione can reach 93.5-95%, and the purity can reach 99-99.5%.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of illustration and description, and is in no way intended to limit the invention.
Example 1
A preparation method of 1, 3-cyclohexanedione comprises the following specific steps:
after 3-stage reaction kettles are connected in series, adding sodium methoxide, sodium hydroxide, metal sodium and tetrahydrofuran into a first-stage reaction kettle, respectively adding 50% of 5-oxomethyl hexanoate of the total input amount into a 1-stage reaction kettle and a 2-stage reaction kettle, controlling the temperature of the 1-stage reaction kettle to 50 ℃, the temperature of the 2-stage reaction kettle to 50 ℃, the temperature of the 3-stage reaction kettle to 60 ℃, reacting the reaction material in the 1-stage reaction kettle for 0.3h, overflowing into the 2-stage reaction kettle, reacting in the 2-stage reaction kettle for 0.5h, overflowing into the 3-stage reaction kettle for 1h, collecting qualified 1, 3-cyclohexanedione sodium salt in the 3-stage reaction kettle, acidifying, centrifuging and drying to obtain the product 1, 3-cyclohexanedione.
Wherein the mass ratio of the sodium methoxide, the sodium hydroxide and the metal sodium is 1:0.5: 0.1.
The molar ratio of sodium methoxide to methyl 5-oxohexanoate was 0.1: 1.
The mass ratio of the tetrahydrofuran to the methyl 5-oxohexanoate is 1: 1.
The yield of the 1, 3-cyclohexanedione can reach 93.5%, and the purity can reach 99.2%.
Example 2
A preparation method of 1, 3-cyclohexanedione comprises the following specific steps:
after 4-stage reaction kettles are connected in series, adding sodium methoxide, sodium hydroxide, metal sodium and acetonitrile into a first-stage reaction kettle, respectively adding 30%, 40% and 30% of 5-oxomethyl hexanoate into a 1-stage reaction kettle, a 2-stage reaction kettle, a 3-stage reaction kettle, a 4-stage reaction kettle, reacting for 0.5h in the 1-stage reaction kettle, overflowing into the 2-stage reaction kettle, reacting for 0.5h in the 2-stage reaction kettle, overflowing into the 3-stage reaction kettle, reacting for 1h in the 3-stage reaction kettle, overflowing into the 4-stage reaction kettle for 2h, collecting qualified 1, 3-cyclohexanedione sodium salt in the 4-stage reaction kettle, acidifying and centrifuging to obtain a product 1, 3-cyclohexanedione.
Wherein the mass ratio of the sodium methoxide, the sodium hydroxide and the metal sodium is 1:0.7: 0.1.
The molar ratio of sodium methoxide to methyl 5-oxohexanoate was 0.2: 1.
The mass ratio of the acetonitrile to the methyl 5-oxohexanoate is 2: 1.
The yield of the 1, 3-cyclohexanedione can reach 93.8%, and the purity can reach 99%.
Example 3
A preparation method of 1, 3-cyclohexanedione comprises the following specific steps:
after 5-stage reaction kettles are connected in series, adding sodium methoxide, sodium hydroxide, metal sodium and DMF into a first-stage reaction kettle, respectively adding 20%, 30%, 30% and 20% of 5-oxomethyl hexanoate into a 1-stage reaction kettle, a 2-stage reaction kettle, a 3-stage reaction kettle and a 4-stage reaction kettle, controlling the temperature of the 1-stage reaction kettle to be 100 ℃, the temperature of the 2-stage reaction kettle to be 80 ℃, the temperature of the 3-stage reaction kettle to be 80 ℃, the temperature of the 4-stage reaction kettle to be 90 ℃, the temperature of the 5-stage reaction kettle to be 70 ℃, reacting materials in the 1-stage reaction kettle for 2 hours, overflowing into the 2-stage reaction kettle, reacting in the 2-stage reaction kettle for 0.5 hour, overflowing into the 3-stage reaction kettle, reacting in the 3-stage reaction kettle for 0.5 hour, overflowing into the 4-stage reaction kettle, reacting in the 4-stage reaction kettle for 0.5 hour, overflowing to a 5-stage reaction kettle, reacting for 0.5h in the 5-stage reaction kettle, collecting qualified 1, 3-cyclohexanedione sodium salt in the 5-stage reaction kettle, acidifying, centrifuging and drying to obtain the product 1, 3-cyclohexanedione.
Wherein the mass ratio of the sodium methoxide, the sodium hydroxide and the metal sodium is 1:0.8: 0.1.
The molar ratio of sodium methoxide to methyl 5-oxohexanoate was 0.3: 1.
The mass ratio of DMF to methyl 5-oxohexanoate is 5: 1.
The yield of the 1, 3-cyclohexanedione can reach 94.2%, and the purity can reach 99.5%.
Example 4
A preparation method of 1, 3-cyclohexanedione comprises the following specific steps:
after 7-stage reaction kettles are connected in series, sodium methoxide, sodium hydroxide, metallic sodium and DMSO are added into a first-stage reaction kettle, 10%, 10%, 20%, 20% and 30% of 5-oxomethyl hexanoate in the total input amount is respectively added into a 1 st-stage reaction kettle, a 2 nd-stage reaction kettle, a 3 rd-stage reaction kettle, a 4 th-stage reaction kettle and a 6 th-stage reaction kettle, the temperature of the 1 st-stage reaction kettle is controlled to be 50 ℃, the temperature of the 2 nd-stage reaction kettle is controlled to be 60 ℃, the temperature of the 3 rd-stage reaction kettle is controlled to be 70 ℃, the temperature of the 4 th-stage reaction kettle is controlled to be 70 ℃, the temperature of the 5 th-stage reaction kettle is controlled to be 60 ℃, the temperature of the 6 th-stage reaction kettle is controlled to be 90 ℃, reaction materials overflow into the 2 nd-stage reaction kettle after reacting in the 1 st-stage reaction kettle for 0.5h, overflow into the 3 rd-stage reaction kettle after reacting in the 2 nd-stage reaction kettle for 0.5h, after reacting for 0.5h in the 3 rd stage reaction kettle, overflowing to the 4 th stage reaction kettle, after reacting for 0.5h in the 4 th stage reaction kettle, overflowing to the 5 th stage reaction kettle, after reacting for 1h in the 5 th stage reaction kettle, overflowing to the 6 th stage reaction kettle, after reacting for 1h in the 6 th stage reaction kettle, overflowing to the 7 th stage reaction kettle, after reacting for 1.5h in the 7 th stage reaction kettle, collecting qualified 1, 3-cyclohexanedione sodium salt in the 7 th stage reaction kettle, acidifying, centrifuging and drying to obtain the product 1, 3-cyclohexanedione.
Wherein the mass ratio of the sodium methoxide, the sodium hydroxide and the metal sodium is 1:1: 0.1.
The molar ratio of sodium methoxide to methyl 5-oxohexanoate was 0.4: 1.
The mass ratio of DMSO to methyl 5-oxohexanoate is 9: 1.
The yield of the 1, 3-cyclohexanedione can reach 95%, and the purity can reach 99.4%.
Example 5
A preparation method of 1, 3-cyclohexanedione comprises the following specific steps:
after 8-stage reaction kettles are connected in series, sodium methoxide, sodium hydroxide, metal sodium and DMAC are added into a first-stage reaction kettle, 10%, 10%, 20%, 20% of 5-oxomethyl hexanoate is respectively added into a 1 st-stage reaction kettle, a 2 nd-stage reaction kettle, a 3 rd-stage reaction kettle, a 4 th-stage reaction kettle, a 5 th-stage reaction kettle, a 6 th-stage reaction kettle and a 7 th-stage reaction kettle, the temperature of the 1 st-stage reaction kettle is controlled to 50 ℃, the temperature of the 2 nd-stage reaction kettle is controlled to 60 ℃, the temperature of the 3 rd-stage reaction kettle is controlled to 80 ℃, the temperature of the 4 th-stage reaction kettle is controlled to 80 ℃, the temperature of the 5 th-stage reaction kettle is controlled to 70 ℃, the temperature of the 6 th-stage reaction kettle is controlled to 80 ℃, the temperature of the 8 th-stage reaction kettle is controlled to 90 ℃, reaction materials are overflowed into the 2 nd-stage reaction kettle after reacting in the 1 st-stage reaction kettle for 1 hour, after reacting for 1 hour in a 2-stage reaction kettle, overflowing to a 3-stage reaction kettle, after reacting for 1.5 hours in the 3-stage reaction kettle, overflowing to a 4-stage reaction kettle, after reacting for 2 hours in the 4-stage reaction kettle, overflowing to a 5-stage reaction kettle, after reacting for 1.5 hours in the 5-stage reaction kettle, overflowing to a 6-stage reaction kettle, after reacting for 2 hours in the 6-stage reaction kettle, overflowing to a 7-stage reaction kettle, reacting for 1 hour in the 7-stage reaction kettle, overflowing to an 8-stage reaction kettle, after reacting for 0.5 hour in an 8-stage reaction kettle, collecting qualified 1, 3-cyclohexanedione sodium salt in the 8-stage reaction kettle, acidifying, centrifuging and drying to obtain the product 1, 3-cyclohexanedione.
Wherein the mass ratio of the sodium methoxide, the sodium hydroxide and the metal sodium is 1:0.9: 0.1.
The molar ratio of sodium methoxide to methyl 5-oxohexanoate was 0.3: 1.
The mass ratio of the DMAC to the methyl 5-oxohexanoate is 10: 1.
The yield of the 1, 3-cyclohexanedione can reach 94.2%, and the purity can reach 99.1%.
Example 6
A preparation method of 1, 3-cyclohexanedione comprises the following specific steps:
after 6-stage reaction kettles are connected in series, sodium methoxide, sodium hydroxide, metal sodium and NMP are added into a first-stage reaction kettle, 20%, 20%, 20% and 20% of 5-oxomethyl hexanoate in the total input amount is respectively added into a 1 st-stage reaction kettle, a 2 nd-stage reaction kettle, a 3 rd-stage reaction kettle, a 4 th-stage reaction kettle and a 5 th-stage reaction kettle, then the temperature of the 1 st-stage reaction kettle is controlled to 50 ℃, the temperature of the 2 nd-stage reaction kettle is controlled to 60 ℃, the temperature of the 3 rd-stage reaction kettle is controlled to 70 ℃, the temperature of the 4 th-stage reaction kettle is controlled to 80 ℃, the temperature of the 5 th-stage reaction kettle is controlled to 90 ℃, the temperature of the 6 th-stage reaction kettle is controlled to 80 ℃, reaction materials react in the 1 st-stage reaction kettle for 0.3h, then overflow into the 2 nd-stage reaction kettle, after reacting in the 2 nd-stage reaction kettle for 0.5h, overflow into the 3 rd-stage reaction kettle, after reacting in the 3 rd-stage reaction kettle for 1h, overflowing to a 4-stage reaction kettle, reacting in the 4-stage reaction kettle for 1 hour, overflowing to a 5-stage reaction kettle, reacting in the 5-stage reaction kettle for 1 hour, collecting qualified 1, 3-cyclohexanedione sodium salt in the 5-stage reaction kettle, acidifying, centrifuging and drying to obtain the product 1, 3-cyclohexanedione.
Wherein the mass ratio of the sodium methoxide, the sodium hydroxide and the metal sodium is 1:1: 0.1.
The molar ratio of sodium methoxide to methyl 5-oxohexanoate is 0.4: 1.
The mass ratio of NMP to methyl 5-oxohexanoate is 10: 1.
The yield of the 1, 3-cyclohexanedione can reach 94.7%, and the purity can reach 99.3%.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (3)
1. A preparation method of 1, 3-cyclohexanedione is characterized in that n reaction kettles are connected in series in a multi-kettle series connection mode, sodium methoxide, sodium hydroxide, metal sodium and an aprotic polar solvent are added into a first-stage reaction kettle, and methyl 5-oxohexanoate is added into the 1 st to n-1 st-stage reaction kettles respectively;
n is 3 to 8;
the temperature of each stage of reaction kettle in the multi-kettle series is controlled to be 50-100 ℃, and the reaction time is 0.3-2 h;
the mass ratio of sodium methoxide, sodium hydroxide and metal sodium is 1 (0.5-1) to 0.1;
the aprotic polar solvent is one of tetrahydrofuran, acetonitrile, DMF, DMSO, DMAC and NMP;
the molar ratio of the sodium methoxide to the methyl 5-oxohexanoate is 0.1-0.4: 1;
the mass ratio of the aprotic polar solvent to the methyl 5-oxohexanoate is 1-10: 1.
2. The method for preparing 1, 3-cyclohexanedione according to claim 1, wherein the amount of methyl 5-oxohexanoate added to each of the 1 to n-1 stage reaction vessels in the multi-vessel cascade is 10 to 50% of the total amount charged, and the last stage reaction vessel is a curing vessel for completely reacting the reaction materials without performing the charging operation.
3. The preparation method of 1, 3-cyclohexanedione as claimed in claim 1, wherein the multiple kettles are connected in series, during the reaction process, the materials of the first-stage reaction kettle overflow to the second-stage reaction kettle, the materials in the second-stage reaction kettle overflow to the third-stage reaction kettle after being full, the materials overflow in sequence, the materials overflow to the last-stage reaction kettle for full reaction, qualified 1, 3-cyclohexanedione sodium salt is collected in the last-stage reaction kettle, and the product 1, 3-cyclohexanedione is obtained by acidification, centrifugation and drying.
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Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922307A (en) * | 1972-09-15 | 1975-11-25 | Hoechst Ag | Process for preparing cyclohexanediones-(1,3) |
| US3932511A (en) * | 1973-03-14 | 1976-01-13 | Stamicarbon B.V. | Preparation of cyclohexane-1,3-dione and of alkyl-substituted derivatives thereof |
| EP0021511A1 (en) * | 1979-06-28 | 1981-01-07 | Stamicarbon B.V. | Process for the preparation of optionally alkyl-substituted resorcinol and catalyst to be used in this process |
| US4409400A (en) * | 1978-06-08 | 1983-10-11 | Hoechst Aktiengesellschaft | Process for the preparation of cyclohexane-1,3-dione from δ-ketohexanoic acid ester |
| JP2008222606A (en) * | 2007-03-09 | 2008-09-25 | Okayama Univ | Process for producing ester, carboxylic acid and amide |
| CN110818540A (en) * | 2019-11-22 | 2020-02-21 | 湖北广富林生物制剂有限公司 | Production process of 1, 3-cyclohexanedione |
| CN111187153A (en) * | 2020-01-10 | 2020-05-22 | 文登市兴文新材料有限公司 | Preparation method of 1, 3-cyclohexanedione |
| CN112028755A (en) * | 2020-09-24 | 2020-12-04 | 青岛科技大学 | Method for preparing 1,3 cyclohexanedione |
| CN112159317A (en) * | 2020-09-22 | 2021-01-01 | 山东智永化工产业技术研究院有限公司 | Method for continuously synthesizing methyl isopropyl ketone |
| CN113336629A (en) * | 2021-03-05 | 2021-09-03 | 上海埃农生物科技有限公司 | Preparation process of 1,3 cyclohexanedione |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ307751B6 (en) * | 2018-03-12 | 2019-04-10 | JBPV s.r.o. | A method of producing terephthalic acid from waste polyethylene terephthalate |
-
2022
- 2022-03-22 CN CN202210279237.2A patent/CN114380674B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922307A (en) * | 1972-09-15 | 1975-11-25 | Hoechst Ag | Process for preparing cyclohexanediones-(1,3) |
| US3932511A (en) * | 1973-03-14 | 1976-01-13 | Stamicarbon B.V. | Preparation of cyclohexane-1,3-dione and of alkyl-substituted derivatives thereof |
| US4409400A (en) * | 1978-06-08 | 1983-10-11 | Hoechst Aktiengesellschaft | Process for the preparation of cyclohexane-1,3-dione from δ-ketohexanoic acid ester |
| EP0021511A1 (en) * | 1979-06-28 | 1981-01-07 | Stamicarbon B.V. | Process for the preparation of optionally alkyl-substituted resorcinol and catalyst to be used in this process |
| JP2008222606A (en) * | 2007-03-09 | 2008-09-25 | Okayama Univ | Process for producing ester, carboxylic acid and amide |
| CN110818540A (en) * | 2019-11-22 | 2020-02-21 | 湖北广富林生物制剂有限公司 | Production process of 1, 3-cyclohexanedione |
| CN111187153A (en) * | 2020-01-10 | 2020-05-22 | 文登市兴文新材料有限公司 | Preparation method of 1, 3-cyclohexanedione |
| CN112159317A (en) * | 2020-09-22 | 2021-01-01 | 山东智永化工产业技术研究院有限公司 | Method for continuously synthesizing methyl isopropyl ketone |
| CN112028755A (en) * | 2020-09-24 | 2020-12-04 | 青岛科技大学 | Method for preparing 1,3 cyclohexanedione |
| CN113336629A (en) * | 2021-03-05 | 2021-09-03 | 上海埃农生物科技有限公司 | Preparation process of 1,3 cyclohexanedione |
Non-Patent Citations (2)
| Title |
|---|
| 1,4-环己二酮的合成研究;安华娟等;《浙江化工》;20060228(第02期);第5+25页 * |
| 邻氨基二苯乙烯与1,3-环己二酮的串联环化反应合成1,4-二氢喹啉衍生物;余飞等;《常州大学学报(自然科学版)》;20190528(第03期);摘要 * |
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| CN114380674A (en) | 2022-04-22 |
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Denomination of invention: A Preparation Method of 1,3-Cyclohexanedione Effective date of registration: 20230713 Granted publication date: 20220520 Pledgee: Pudong Shanghai Development Bank Limited by Share Ltd. Lanzhou branch Pledgor: Shandong Zhiyong Chemical Industry Technology Research Institute Co.,Ltd. Registration number: Y2023980048335 |