CN104974036A - Purifying method of crude trimesic acid - Google Patents
Purifying method of crude trimesic acid Download PDFInfo
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- CN104974036A CN104974036A CN201410144243.2A CN201410144243A CN104974036A CN 104974036 A CN104974036 A CN 104974036A CN 201410144243 A CN201410144243 A CN 201410144243A CN 104974036 A CN104974036 A CN 104974036A
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- CN
- China
- Prior art keywords
- trimesic acid
- dmf
- thick
- tma
- adducts crystal
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- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000013078 crystal Substances 0.000 claims abstract description 31
- 238000000746 purification Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 30
- 239000002904 solvent Substances 0.000 abstract description 15
- 238000010438 heat treatment Methods 0.000 abstract description 10
- 239000000843 powder Substances 0.000 abstract description 4
- 238000001953 recrystallisation Methods 0.000 abstract description 4
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WIAPFNDQWLOVKC-UHFFFAOYSA-N 1,3,5-trimethylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)(C(O)=O)C1 WIAPFNDQWLOVKC-UHFFFAOYSA-N 0.000 description 1
- NBEFMISJJNGCIZ-UHFFFAOYSA-N 3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C)=CC(C=O)=C1 NBEFMISJJNGCIZ-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a purifying method of crude trimesic acid, wherein the method includes the steps of forming an adduct crystal from N,N-dimethylformamide and crude trimesic acid and heating the adduct crystal to remove the N,N-dimethylformamide, thereby obtaining trimesic acid being not less than 99.0% in purity. By means of the solvent recrystallization with the N,N-dimethylformamide and heating decomposition of the adduct crystal, a TMA white powder is obtained, wherein the content of TMA is not less than 99.0% and the b value is not more than 2.0%, thereby purifying the crude trimesic acid.
Description
Technical field
The present invention relates to a kind of method of purification of thick trimesic acid, particularly a kind of method adopting solvent and thick trimesic acid to form adducts crystal to carry out purifying.
Background technology
Trimesic acid (TMA) is a kind of desirable high molecular synthetic material, mainly as preparing reverse osmosis membrane, polymeric membrane for separation, for the highly purified and gas delivery etc. of sea water desaltination, water; In biological medicine, it can be used for preparing cancer therapy drug, plant-growth regulator etc.; On aircraft industry, it also can be used as the solid-fuelled linking agent of rocket propulsion and prepares high temperature-resistant polymer material etc.In addition, trimesic acid is produced also significant to plastics, regenerated fiber, water soluble allcylbenzene resin, softening agent etc.
The production method of trimesic acid has three kinds: sym-trimethylbenzene potassium permanganate oxidation method, sym-trimethylbenzene nitric acid oxidation method and mesitylene air oxidation style.Industrial main employing mesitylene air oxidation style produces trimesic acid.Except containing except trimesic acid (TMA about 98.5%) in the thick trimesic acid product obtained by oxidizing reaction, also containing a small amount of oreinol dioctyl phthalate, 3, the foreign pigments such as 5-mesitylenic acid and 3,5-dimethylbenzaldehyde, must carry out purification processes to it.
Document " adducts crystal that trimesic acid and N-Methyl pyrrolidone are formed characterizes " (Peng Ge, Guo Xia, become promising, Deng. chemistry world [J], 2010,51 (10): 623-625) have employed solvent N-methyl pyrilidone (NMP) and trimesic acid (TMA) to carry out recrystallization and forms adducts crystal, and make solvent NMP remove the purification carrying out TMA by heating, when temperature is to 225 DEG C, solvent NMP can be removed completely.But the energy consumption of the method is high, cost is also higher.
Summary of the invention
The object of the present invention is to provide a kind of more cheap than above-mentioned nmp solvent, adducts crystal can be formed with TMA, and can the TMA method of purification of desolvation completely under lower Heating temperature, while, also reduces production cost and has saved energy consumption.
Concrete technical scheme of the present invention is as follows:
A method of purification for thick trimesic acid, adopts DMF and thick trimesic acid to form adducts crystal; Then the adducts crystal obtained is heated, remove DMF, obtain the trimesic acid of purity >=99.0%.
The concrete steps that employing DMF and thick trimesic acid form adducts crystal are as follows:
(1) be dissolved in by thick trimesic acid in the DMF of 95-105 DEG C and form mixing solutions, during dissolving, the mass ratio of thick trimesic acid and DMF is 1:2 ~ 5;
(2) mixing solutions obtained in step (1) is placed in crystallisation by cooling under room temperature, then filters, obtain adducts crystal.
In step (1), thick trimesic acid is dissolved in the DMF of 100 DEG C and forms mixing solutions..
The adducts crystal obtained is heated to 170-175 DEG C, removes DMF, obtain the trimesic acid of purity >=99.0%.Adducts crystal is heated to about 170-175 DEG C end, and what lose in this process is lower boiling solvent DMF molecule, remains high boiling TMA molecule.
The adducts crystal obtained is heated to 170 DEG C, removes DMF, obtain the trimesic acid of purity >=99.0%.
The present invention adopts solvent DMF (DMF) and TMA to carry out recrystallization and forms TMA-DMF adducts crystal, when getting final product complete desolvation DMF to during temperature 170 DEG C, to reach the object of purifying to thick TMA to TMA-DMF heating crystals.
Adopt DMF solvent recrystallization and by the TMA white powder that obtains after adducts crystal thermal degradation, content >=99.0% of TMA, b value≤2.0, reach the object of product purification.
Embodiment
Below the specific embodiment of the present invention is described in detail, but it is pointed out that protection scope of the present invention not by the restriction of these embodiments, but determined by claims.
embodiment 1
By crude benzol tricarboxylic acid (TMA content 98.5%) 50g, join about 100 DEG C, in DMF (DMF) solvent of 200g, thick TMA dissolves; Be cooled to room temperature, then filter, obtain adducts crystal; Carry out thermogravimetric analysis by filtering the white adducts crystal heating obtained, crystal decomposes from about 70 DEG C, to about 170 DEG C end; To the white powder analysis composition obtained after heating, measure acid number, and use colour-difference meter to measure its b value.The results are shown in Table 1.
embodiment 2-embodiment 6
Implementation process is identical with embodiment 1, the mass ratio of the TMA content in crude benzol tricarboxylic acid, solvent DMF and crude benzol tricarboxylic acid, purify after the analytical results of benzene tricarboxylic acid all in table 1.
comparative example
By crude benzol tricarboxylic acid (TMA content 98.5%) 50g, join about 120 DEG C, in N-Methyl pyrrolidone (NMP) solvent of 200g, thick TMA dissolves; Be cooled to room temperature, obtain the white crystal that particle is thick.Carry out thermogravimetric analysis by filtering the white crystal heating obtained, crystal decomposes from about 75 DEG C, to about 225 DEG C end.To the white powder analysis composition obtained after heating, measure acid number, and use colour-difference meter to measure its b value.The results are shown in Table 1.
Known by the test-results data of embodiment 1-embodiment 6 in table 1, by adopting solvent N, dinethylformamide (DMF) and TMA form TMA-DMF adducts crystal, then by heating, the solvent DMF in TMA-DMF are removed, and thick trimesic acid can be purified to more than 99.0%.
Known by the test-results data of embodiment 1-embodiment 6 and comparative example in contrast table 1, when adopting DMF comparatively to adopt NMP as solvent, when making adducts crystal thermal degradation complete, top temperature can drop to about 170 DEG C from about 225 DEG C, reaches the object that industrial production is energy-conservation.
Although be described in detail the specific embodiment of the present invention above in conjunction with the embodiments, it is pointed out that protection scope of the present invention not by the restriction of these embodiments, but determined by claims.Those skilled in the art can carry out suitable change to these embodiments in the scope not departing from technological thought of the present invention and purport, and the embodiment after these changes is obviously also included within protection scope of the present invention.
Claims (5)
1. a method of purification for thick trimesic acid, is characterized in that adopting DMF and thick trimesic acid to form adducts crystal; Then the adducts crystal obtained is heated, remove DMF, obtain the trimesic acid of purity >=99.0%.
2. method of purification according to claim 1, is characterized in that adopting DMF and thick trimesic acid to form the concrete steps of adducts crystal as follows:
(1) be dissolved in by thick trimesic acid in the DMF of 95-105 DEG C and form mixing solutions, during dissolving, the mass ratio of thick trimesic acid and DMF is 1:2 ~ 5;
(2) mixing solutions obtained in step (1) is placed in crystallisation by cooling under room temperature, then filters, obtain adducts crystal.
3. method of purification according to claim 2, is characterized in that, in step (1), being dissolved in by thick trimesic acid in the DMF of 100 DEG C and forming mixing solutions..
4. the method for purification according to above-mentioned arbitrary claim, is characterized in that the adducts crystal obtained to be heated to 170-175 DEG C, removes DMF, obtain the trimesic acid of purity >=99.0%.
5. method of purification according to claim 4, is characterized in that the adducts crystal obtained to be heated to 170 DEG C, removes DMF, obtain the trimesic acid of purity >=99.0%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410144243.2A CN104974036B (en) | 2014-04-11 | 2014-04-11 | A kind of method of purification of thick trimesic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410144243.2A CN104974036B (en) | 2014-04-11 | 2014-04-11 | A kind of method of purification of thick trimesic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104974036A true CN104974036A (en) | 2015-10-14 |
| CN104974036B CN104974036B (en) | 2016-10-05 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106832082A (en) * | 2016-05-27 | 2017-06-13 | 张玲 | A kind of auxiliary agent for refining trimesic acid |
| CN107774329A (en) * | 2016-08-29 | 2018-03-09 | 中国石油化工股份有限公司 | A kind of metal-organic framework materials and preparation method thereof |
| CN109384935A (en) * | 2017-08-08 | 2019-02-26 | 中国石油化工股份有限公司 | A kind of metal-organic framework materials and preparation method thereof |
-
2014
- 2014-04-11 CN CN201410144243.2A patent/CN104974036B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| S. CHATTERJEE ET AL.: "Self-assembled four-membered networks of trimesic acid forming organic channel structures", 《JOURNAL OF MOLECULAR STRUCTURE 》 * |
| 彭革等: "均苯三酸与N-甲基吡咯烷酮形成的加合物晶体表征", 《化学世界》 * |
| 彭革等: "芳香二羧酸在有机溶剂中的加合结晶", 《高校化学工程学报 》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106832082A (en) * | 2016-05-27 | 2017-06-13 | 张玲 | A kind of auxiliary agent for refining trimesic acid |
| CN107774329A (en) * | 2016-08-29 | 2018-03-09 | 中国石油化工股份有限公司 | A kind of metal-organic framework materials and preparation method thereof |
| CN109384935A (en) * | 2017-08-08 | 2019-02-26 | 中国石油化工股份有限公司 | A kind of metal-organic framework materials and preparation method thereof |
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| Publication number | Publication date |
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| CN104974036B (en) | 2016-10-05 |
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