CN118164995B - Preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride - Google Patents
Preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride Download PDFInfo
- Publication number
- CN118164995B CN118164995B CN202410229890.7A CN202410229890A CN118164995B CN 118164995 B CN118164995 B CN 118164995B CN 202410229890 A CN202410229890 A CN 202410229890A CN 118164995 B CN118164995 B CN 118164995B
- Authority
- CN
- China
- Prior art keywords
- dimethyl
- purity
- tetracarboxylic dianhydride
- cyclobutane tetracarboxylic
- steps
- 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
- SBHHKGFHJWTZJN-UHFFFAOYSA-N 1,3-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C)(C(O)=O)C1C(O)=O SBHHKGFHJWTZJN-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 15
- 229930195729 fatty acid Natural products 0.000 claims abstract description 15
- 239000000194 fatty acid Substances 0.000 claims abstract description 15
- -1 fatty acid ester Chemical class 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 15
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000004650 carbonic acid diesters Chemical class 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000012046 mixed solvent Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000011907 photodimerization Methods 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 239000012043 crude product Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 150000005690 diesters Chemical class 0.000 claims description 11
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- 229940117955 isoamyl acetate Drugs 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 230000007547 defect Effects 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 239000004642 Polyimide Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- MQQRFOXFIPBFOV-UHFFFAOYSA-N 1,2-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C(O)=O)C1(C)C(O)=O MQQRFOXFIPBFOV-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 238000013032 photocatalytic reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention provides a preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride, and relates to the technical field of fine chemical engineering. The preparation method mainly comprises the steps of carrying out photodimerization reaction on carbonic acid diester serving as a solvent and citraconic anhydride, removing solvent solution, dissolving a product into fatty acid ester, mixing, filtering, continuously stirring and filtering by adopting a carbonic acid diester and fatty acid ester mixed solvent, and carrying out heating reaction by adopting acetic anhydride, and filtering. The invention overcomes the defects of the prior art, improves the purity of the 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride production, reduces the production cost and provides good support for the industrialized enlarged production of the product.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride.
Background
1, 3-Dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride (1, 3-DMCBDA) is an alicyclic dianhydride monomer for synthesizing polyimide; 1,3-DMCBDA adds two methyl groups on the non-conjugated alicyclic structure, which can further increase the molecule chain distance of polyimide, improve the transparency, solubility and dielectric property of polyimide, meet the requirements of photoalignment films and can be widely applied in the field of photoelectric display.
Japanese patent application laid-open No. 4-106127 discloses a process for producing citraconic anhydride by photodimerization, wherein more than half of 1, 2-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride (1, 2-DMCBDA) is present in addition to 1,3-DMCBDA target product in the resultant mixture. 1,2-DMCBDA itself is not light yellow and has low symmetry, which can affect the transparency and molecular weight of polyimide.
The prior patent CN105916866B obtains that 1,3-DMCBDA still contains 0.5 percent of 1,2-DMCBDA by a method of acetic anhydride reflux; CN109422762a reports a method of dissolution filtration using ketones containing 5 or more carbon atoms; the scheme uses a large amount of solvent, and the content of 1,2-DMCBDA can be reduced to 0.5%; therefore, how to prepare the high-purity 1,3-DMCBDA is a problem to be solved in the current industrial process.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride, which effectively improves the production purity of the 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride and is convenient for industrial production.
In order to achieve the above object, the technical scheme of the present invention is realized by the following technical scheme:
a method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride, which is characterized by comprising the following steps:
(1) Adding citraconic anhydride into carbonic diester according to mass to carry out photodimerization reaction to obtain 1,3-DMCBDA crude product solution S1 for standby;
(2) Distilling the S1 under reduced pressure to remove part of carbonic diester, adding fatty acid ester, stirring, and filtering to obtain A1, 3-DMCBDA crude product A1;
(3) Dissolving the crude product A1 into a mixed solvent of carbonic diester and fatty acid ester, stirring and filtering to obtain A1, 3-DMCBDA crude product A2;
(4) Heating the crude product A2 in acetic anhydride, cooling and filtering to obtain high-purity 1,3-DMCBDA.
Preferably, the carbonic acid diester is dimethyl carbonate or diethyl carbonate.
Preferably, in the step (1), the mass ratio of citraconic anhydride to carbonic acid diester is 1:5-20.
Preferably, the photodimerization reaction in the step (1) is carried out by selecting an ultraviolet light source with the wavelength of 290-390 nm, and controlling the reaction temperature to be 5-20 ℃ for 5-48h.
Preferably, the fatty acid ester is any one of methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate and isoamyl acetate.
Preferably, the mass ratio of the addition amount of the fatty acid ester to the citraconic anhydride in the step (2) is 0.5-3:1.
Preferably, the amount of S1 carbonic acid diester distilled off in the step (2) is 85 to 95%.
Preferably, in the step (3), the ratio of the crude product A1 to the mixed solvent is 1:1-5, and the mass ratio of the carbonic diester to the fatty acid ester in the mixed solvent is 0-20: 100-80.
Preferably, in the step (4), the mass ratio of the crude product A2 to acetic anhydride is 1:3-10.
Preferably, the heating reaction temperature in the step (4) is 130-150 ℃ and the reaction time is 2-10 h.
The invention provides a preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride, which has the advantages that compared with the prior art:
(1) The preparation method of the invention can obtain high-purity 1,3-DMCBDA and final products 1,3-DMCBDA:1,2-DMCBDA is more than or equal to 99.8:0.2
(2) When the content of the 1,2-DMCBDA isomer is high, the invention adopts the carbonic diester and the fatty acid ester with proper proportion to dissolve most of the 1,2-DMCBDA isomer under the normal temperature condition; when the content of the 1,2-DMCBDA isomer is low, removing a small amount of residual 1,2-DMCBDA isomer by adopting acetic anhydride reflux; thereby obtaining a high-purity 1,3-DMCBDA product;
(3) The invention adopts the carbonic acid diester and the fatty acid ester as main solvents, and the carbonic acid diester and the fatty acid ester generally have lower boiling points, thereby being beneficial to recycling; the dissolution and purification under normal temperature conditions are safe and energy-saving;
(4) The invention carries out the reflux refining of acetic anhydride when the content of 1,2-DMCBDA isomer is low, reduces the consumption of acetic anhydride and is beneficial to industrial scale-up production.
Detailed Description
The present application will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present application more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the application.
Examples of certain embodiments of the application are given below and are not intended to limit the scope of the application.
In addition, the materials, the processing means, and the like, which are present in the present application, are common materials and familiar technical means in the art unless otherwise specified. The numerical values set forth in the following examples are reported as precisely as possible, but those of ordinary skill in the art will understand that, due to unavoidable measurement errors and experimental operating problems, each numerical value should be understood as a divisor rather than an absolute accurate numerical value.
Example 1:
Preparation of 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride:
(1) Adding 4kg of citraconic anhydride and 40kg of dimethyl carbonate into a photocatalytic reaction device, controlling the reaction temperature to be 10 ℃, and irradiating 365-380 nm LED lamps for 30 hours under the stirring condition to obtain a solution S1;
(2) After 92% of dimethyl carbonate is removed by reduced pressure distillation of the solution S1, 6kg of ethyl acetate is added, stirred and filtered to obtain 1.82kg of 1,3-DMCBDA crude product A1;
(3) 1.82kg of crude product A1 is dissolved in 5.46kg of ethyl acetate, stirred and filtered to obtain 1.2kg of 1,3-DMCBDA crude product A2;
(4) Dispersing 1.2kg of crude product A2 in 7.2kg of acetic anhydride, heating to 150 ℃ for reaction for 5 hours, cooling and filtering to obtain 1.05kg of high-purity 1,3-DMCBDA products.
Example 2:
Preparation of 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride:
step (1) is the same as in example 1;
(2) After removing 95% dimethyl carbonate by reduced pressure distillation of the solution S1, adding 2kg of ethyl acetate, stirring and filtering to obtain 2.04kg of 1,3-DMCBDA crude product A1;
(3) 2.04kg of crude product A1 is dissolved in 10.2kg of mixed solvent (dimethyl carbonate: ethyl acetate=10:90), stirred and filtered to obtain 1.08kg of 1,3-DMCBDA crude product A2;
(4) Dispersing 1.08kg of crude product A2 into 6.48kg of acetic anhydride, heating to 150 ℃ for reaction for 5 hours, cooling and filtering to obtain 0.932kg of high-purity 1,3-DMCBDA products.
Comparative example 1:
Preparation of 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride:
step (1) is the same as in example 1;
(2) After 82% of dimethyl carbonate is removed by reduced pressure distillation of the solution S1, 1.12kg of 1,3-DMCBDA crude product A1 is obtained by direct filtration;
(3) Dispersing 1.12kg of crude product A1 into 6.72kg of acetic anhydride, heating to 150 ℃ for reaction for 5 hours, cooling and filtering to obtain 0.678kg of high-purity 1,3-DMCBDA products.
Comparative example 2:
Preparation of 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride:
steps (1), (2) are the same as comparative example 1;
(3) 1.12kg of crude A1 are dissolved in 5.6kg of ethyl acetate, stirred and filtered to give 0.846kg of 1,3-DMCBDA product.
Comparative example 3:
Preparation of 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride:
4kg of citraconic anhydride and 40kg of dimethyl carbonate are added into a photocatalysis reaction device, the reaction temperature is controlled to be 10 ℃, and under the stirring condition, 390-410 nm LED lamps are irradiated for 30 hours, so that a solution S1 is obtained.
And (3) detection:
For the production processes of examples 1-2 and comparative examples 1-3 described above, the raw material residue ratio of S1, the yields of crude A1, crude A2 and 1,3-DMCBDA products, and the ratio of 1,3-DMCBDA to 1,2-DMCBDA in each production process were examined, and the specific results are shown in the following table:
In summary, example 1 in comparison with comparative example 1 found that decreasing the distilled amount of dimethyl carbonate while decreasing the 1, 2-isomer content was accompanied by more dissolution loss of 1, 3-DMCBDA; on the other hand, the reflux of acetic anhydride is carried out under the condition of higher content of 1, 2-isomer, and more 1, 2-isomer still remains in the product; in comparative example 2, even though more dimethyl carbonate was retained and ethyl acetate was added in a larger proportion, the 1, 2-isomer remained in the product of 0.7% in comparison example 1, which is disadvantageous for the preparation of high purity 1, 3-DMCBDA.
And the LED lamp wavelength was changed in comparative example 3, the photodimerization efficiency was greatly reduced.
The above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride, which is characterized by comprising the following steps:
(1) Adding citraconic anhydride into carbonic diester according to mass to carry out photodimerization reaction to obtain 1,3-DMCBDA crude product solution S1 for standby;
(2) Distilling the S1 under reduced pressure to remove part of carbonic diester, adding fatty acid ester, stirring, and filtering to obtain A1, 3-DMCBDA crude product A1;
(3) Dissolving the crude product A1 into a mixed solvent of carbonic diester and fatty acid ester, stirring and filtering to obtain A1, 3-DMCBDA crude product A2;
(4) Heating the crude product A2 in acetic anhydride, cooling and filtering to obtain high-purity 1,3-DMCBDA.
2. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the carbonic diester is dimethyl carbonate or diethyl carbonate.
3. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: in the step (1), the mass ratio of citraconic anhydride to carbonic diester is 1:5-20.
4. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the photodimerization reaction mode in the step (1) is to select an ultraviolet light source with the wavelength of 290-390 nm, and the reaction temperature is controlled to be 5-20 ℃ for 5-48h.
5. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the fatty acid ester is any one of methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate and isoamyl acetate.
6. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the mass ratio of the addition amount of the fatty acid ester to the citraconic anhydride in the step (2) is 0.5-3:1.
7. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the amount of the S1 carbonic acid diester distilled off in the step (2) is 85 to 95%.
8. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: in the step (3), the ratio of the crude product A1 to the mixed solvent is 1:1-5, and the mass ratio of the carbonic diester to the fatty acid ester in the mixed solvent is 0-20: 100-80.
9. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the mass ratio of the crude product A2 to acetic anhydride in the step (4) is 1:3-10.
10. The method for preparing high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride according to claim 1, wherein the method comprises the following steps: the heating reaction temperature in the step (4) is 130-150 ℃ and the reaction time is 2-10 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410229890.7A CN118164995B (en) | 2024-02-29 | 2024-02-29 | Preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410229890.7A CN118164995B (en) | 2024-02-29 | 2024-02-29 | Preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN118164995A CN118164995A (en) | 2024-06-11 |
| CN118164995B true CN118164995B (en) | 2024-09-13 |
Family
ID=91351209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410229890.7A Active CN118164995B (en) | 2024-02-29 | 2024-02-29 | Preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118164995B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105916866A (en) * | 2014-01-17 | 2016-08-31 | 日产化学工业株式会社 | Method for producing cyclobutane tetracarboxylic acid derivative |
| CN109422762A (en) * | 2017-08-29 | 2019-03-05 | Jsr株式会社 | The manufacturing method of New cyclobutane derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4852206B2 (en) * | 2001-12-26 | 2012-01-11 | 日産化学工業株式会社 | Method for producing cyclobutanetetracarboxylic dianhydride compound |
| CN110105367A (en) * | 2014-01-17 | 2019-08-09 | 日产化学工业株式会社 | The manufacturing method of cyclobutane tetracarboxylic acid derivatives |
-
2024
- 2024-02-29 CN CN202410229890.7A patent/CN118164995B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105916866A (en) * | 2014-01-17 | 2016-08-31 | 日产化学工业株式会社 | Method for producing cyclobutane tetracarboxylic acid derivative |
| CN109422762A (en) * | 2017-08-29 | 2019-03-05 | Jsr株式会社 | The manufacturing method of New cyclobutane derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| CN118164995A (en) | 2024-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101004211B1 (en) | Process for the purification of crude carboxylic acid slurry | |
| CN114787140B (en) | Heat treatment of organic acids and purified 2, 5-furandicarboxylic acid | |
| US5859294A (en) | Process for the production of high-purity naphthalenedicarboxylic acid | |
| CN118164995B (en) | Preparation method of high-purity 1, 3-dimethyl-1, 2,3, 4-cyclobutane tetracarboxylic dianhydride | |
| WO2018180855A1 (en) | Method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride | |
| KR20050085463A (en) | Process for the oxidative purification of terephthalic acid | |
| CN114929679B (en) | Heat treatment of water and purified 2, 5-furandicarboxylic acid | |
| KR101257962B1 (en) | Process for preparing purified terephthalic acid | |
| CN107540538B (en) | Composition, reaction system and method for preparing 5-methyl isophthalic acid | |
| JP2006083080A (en) | Method for producing hydrogenated aromatic polycarboxylic acid | |
| CN115850061A (en) | Refining method of diphenyl ether tetracarboxylic acid | |
| JP3879781B2 (en) | Method for producing high purity 2,6-naphthalenedicarboxylic acid | |
| JPH09151162A (en) | Purification of naphthalenedicarboxylic acid | |
| US7417108B2 (en) | Process for production of 2,3,3′,4′-biphenyltetracarboxylic dianhydride | |
| KR100711300B1 (en) | Manufacturing method of high purity naphthalenedi carboxylic acid | |
| US6579990B2 (en) | Process for producing refined pyromellitic acid and refined pyromellitic anhydride | |
| JPH1180074A (en) | Production of highly pure 2,6-naphthalene dicarboxylic acid | |
| JPH09208518A (en) | Production of high-purity naphthalenedicarboxylic acid | |
| JPH09104654A (en) | Purification of naphthalenedicarboxylic acid | |
| JP3757989B2 (en) | Method for purifying naphthalenedicarboxylic acid | |
| JP2006328040A (en) | Method for producing 2,3,3',4'-biphenyltetracarboxylic acid dianhydride | |
| JP3826960B2 (en) | Method for producing high purity naphthalenedicarboxylic acid | |
| JPH08193049A (en) | Production of 2,6-naphthalenedicarboxylic acid and its ester | |
| JP3348462B2 (en) | Method for producing high-purity terephthalic acid | |
| CN118043300A (en) | Process for producing fluorenone |
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 |