CN103539660A - Method of preparing trans-1,4-cyclohexane dicarboxylic acid from hybrid 1,4-cyclohexane dicarboxylic acid - Google Patents
Method of preparing trans-1,4-cyclohexane dicarboxylic acid from hybrid 1,4-cyclohexane dicarboxylic acid Download PDFInfo
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- CN103539660A CN103539660A CN201310440947.XA CN201310440947A CN103539660A CN 103539660 A CN103539660 A CN 103539660A CN 201310440947 A CN201310440947 A CN 201310440947A CN 103539660 A CN103539660 A CN 103539660A
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- Prior art keywords
- cyclohexanedicarboxylic acid
- mixing
- trans
- dicarboxylic acid
- cyclohexane dicarboxylic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method of preparing trans-1,4-cyclohexane dicarboxylic acid from hybrid 1,4-cyclohexane dicarboxylic acid. The method comprises the following steps: adding the hybrid 1,4-cyclohexane dicarboxylic acid into a DMF (Dimethyl Formamide) solvent; and adding a little catalyst, heating and refluxing, cooling and crystallizing, and filtering to obtain the trans-1,4-cyclohexane dicarboxylic acid. The method disclosed by the invention is simple in process, easy to operate, high in product yield and high in purity.
Description
Technical field
The present invention relates to a kind of method of being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid, belong to compound preparing technical field.
Background technology
1,4-cyclohexane cyclohexanedimethanodibasic (CHDA) is a kind of important production of polyester raw material, with terephthalic acid (TPA) esterification with di-carboxylic acid feature, after polycondensation, for the production of trevira, the fiber of this commodity Kodel by name is developed by U.S. Eastman company.Be a kind of high poly-linear condensation polymer, there is relative density few, the feature such as fusing point is high, good electrical property.Be specially adapted to electrical equipment, adopt (PET) resin of CHDA modification.And trans structure has better performance, but the industrial terephthalic acid Hydrogenation that generally adopts is for 1,4 cyclohexanedicarboxylic acid at present, and the product obtaining is mixing structure.Therefore pure trans 1,4 cyclohexanedicarboxylic acid preparation has very large market potential.
Summary of the invention
The object of the invention is to for deficiency of the prior art, a kind of method of being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid is provided.
For solving the problems of the technologies described above, the present invention adopts following technical scheme to realize:
By mixing 1,4-cyclohexane cyclohexanedimethanodibasic prepares trans 1, the method of 4-cyclohexane cyclohexanedimethanodibasic, its innovative point is: described method is that mixing 1,4 cyclohexanedicarboxylic acid is joined in DMF solvent, and adds a certain amount of catalyzer, reflux, crystallisation by cooling, filters and obtains trans 1,4 cyclohexanedicarboxylic acid again.
Further, what described solvent can be in DMF, dioxane is a kind of, and preferred solvent is DMF.
Further, the quality of described solvent is raw materials quality one times
Further, described catalyzer is a kind of in sodium methylate, sodium ethylate, sodium hydroxide, preferably sodium methylate.
Further, the consumption of described catalyzer is the 1%-5% of the quality of the mixing 1,4 cyclohexanedicarboxylic acid of raw material, preferably 1%.
Further, the described temperature rising reflux time is 6-24h, preferably 12h.
Further, described reflux temperature is 160 ℃.
Beneficial effect of the present invention: technique of the present invention is simple, easy to operate, and product yield is high, and purity is high.
Embodiment
Below in conjunction with specific embodiment, technical scheme of the present invention is elaborated.
Embodiment 1
50 grams of mixing 1,4 cyclohexanedicarboxylic acids join in 50 grams of solvent DMF, and add 0.5 gram of sodium methylate solid, are heated to the 12h that refluxes, be cooled to 5-10 ℃ of crystallization, after filtration drying, obtain 42.5 grams of trans 1,4 cyclohexanedicarboxylic acids, yield 85.1%, mixing purity is 99.80%, and trans 98.5%.
Embodiment 2
100 grams of mixing 1,4 cyclohexanedicarboxylic acids join in 100 grams of solvent DMF, and add 1 gram of sodium methylate solid, are heated to the 12h that refluxes, be cooled to 5-10 ℃ of crystallization, after filtration drying, obtain 86.3 grams of trans 1,4 cyclohexanedicarboxylic acids, yield 86.3%, mixing purity is 99.78%, and trans 98.7%.
Embodiment 3
200 grams of mixing 1,4 cyclohexanedicarboxylic acids join in 200 grams of solvent DMF, and add 2 grams of sodium methylates, are heated to the 12h that refluxes, be cooled to 5-10 ℃ of crystallization, after filtration drying, obtain 173.2 grams of trans 1,4 cyclohexanedicarboxylic acids, yield 86.6%, mixing purity is 99.88%, and trans 98.9%.
Embodiment 4
400 grams of mixing 1,4 cyclohexanedicarboxylic acids join in 400 grams of solvent DMF, and add 4 grams of sodium methylates, are heated to the 12h that refluxes, be cooled to 5-10 ℃ of crystallization, after filtration drying, obtain 358.0 grams of trans 1,4 cyclohexanedicarboxylic acids, yield 89.5%, mixing purity is 99.82%, and trans 99.0%.
Above-described embodiment is only in order to illustrate technical scheme of the present invention; but not design of the present invention and protection domain are limited; those of ordinary skill in the art modifies or is equal to replacement technical scheme of the present invention; and not departing from aim and the scope of technical scheme, it all should be encompassed in claim scope of the present invention.
Claims (11)
1. by mixing 4-cyclohexane cyclohexanedimethanodibasic, prepare trans 1, the method of 4-cyclohexane cyclohexanedimethanodibasic, it is characterized in that: described method is by mixing 1,4-cyclohexane cyclohexanedimethanodibasic joins in DMF solvent, and add a certain amount of catalyzer, reflux, then crystallisation by cooling, filtration obtains trans 1,4 cyclohexanedicarboxylic acid.
2. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 1, is characterized in that: what described solvent can be in DMF, dioxane is a kind of.
3. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 2, is characterized in that: described solvent is DMF.
4. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 1, is characterized in that: the quality of described solvent is raw materials quality one times.
5. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 1, is characterized in that: described catalyzer is a kind of in sodium methylate, sodium ethylate, sodium hydroxide.
6. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 4, is characterized in that: described catalyzer is sodium methylate.
7. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 1, is characterized in that: the consumption of described catalyzer is the 1%-5% of the quality of the mixing 1,4 cyclohexanedicarboxylic acid of raw material.
8. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 6, is characterized in that: the consumption of described catalyzer be the mixing 1,4 cyclohexanedicarboxylic acid of raw material quality 1%.
9. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 1, is characterized in that: the described temperature rising reflux time is 6-24h.
10. the method for being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 8, is characterized in that: the described temperature rising reflux time is 12h.
11. methods of being prepared trans 1,4 cyclohexanedicarboxylic acid by mixing 1,4 cyclohexanedicarboxylic acid according to claim 1, is characterized in that: described reflux temperature is 160 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310440947.XA CN103539660A (en) | 2013-09-25 | 2013-09-25 | Method of preparing trans-1,4-cyclohexane dicarboxylic acid from hybrid 1,4-cyclohexane dicarboxylic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310440947.XA CN103539660A (en) | 2013-09-25 | 2013-09-25 | Method of preparing trans-1,4-cyclohexane dicarboxylic acid from hybrid 1,4-cyclohexane dicarboxylic acid |
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| CN103539660A true CN103539660A (en) | 2014-01-29 |
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| CN201310440947.XA Pending CN103539660A (en) | 2013-09-25 | 2013-09-25 | Method of preparing trans-1,4-cyclohexane dicarboxylic acid from hybrid 1,4-cyclohexane dicarboxylic acid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945237A (en) * | 2015-05-15 | 2015-09-30 | 济南磐石医药科技有限公司 | Synthesis method of (1R, 2R)-trans-cyclohexane dicarboxylic acid |
| CN106316825A (en) * | 2016-08-24 | 2017-01-11 | 泰州精英化成医药科技有限公司 | Preparing method for trans- 4- hydroxycyclohexanecarboxylic acid |
| JP2022513714A (en) * | 2018-12-27 | 2022-02-09 | ハンワ ソリューションズ コーポレイション | Method for producing 1,4-cyclohexanedimethanol |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5824540A (en) * | 1981-08-06 | 1983-02-14 | Dai Ichi Seiyaku Co Ltd | Preparation of trans-hexyhydroterephthalic acid |
| CN1935773A (en) * | 2001-10-26 | 2007-03-28 | 三菱化学株式会社 | Process for producing trans-1,4-cyclohexanedicarboxylic acid |
| JP2008063311A (en) * | 2006-09-11 | 2008-03-21 | Iwatani Industrial Gases Corp | Method for producing trans-cyclohexanedicarboxylic acid |
| JP2010270093A (en) * | 2009-05-25 | 2010-12-02 | Iwatani Industrial Gases Corp | Method of producing dimethyl trans-1,4-cyclohexanedicarboxylate, and high purity dimethyl trans-1,4-cyclohexanedicarboxylate |
-
2013
- 2013-09-25 CN CN201310440947.XA patent/CN103539660A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5824540A (en) * | 1981-08-06 | 1983-02-14 | Dai Ichi Seiyaku Co Ltd | Preparation of trans-hexyhydroterephthalic acid |
| CN1935773A (en) * | 2001-10-26 | 2007-03-28 | 三菱化学株式会社 | Process for producing trans-1,4-cyclohexanedicarboxylic acid |
| JP2008063311A (en) * | 2006-09-11 | 2008-03-21 | Iwatani Industrial Gases Corp | Method for producing trans-cyclohexanedicarboxylic acid |
| JP2010270093A (en) * | 2009-05-25 | 2010-12-02 | Iwatani Industrial Gases Corp | Method of producing dimethyl trans-1,4-cyclohexanedicarboxylate, and high purity dimethyl trans-1,4-cyclohexanedicarboxylate |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945237A (en) * | 2015-05-15 | 2015-09-30 | 济南磐石医药科技有限公司 | Synthesis method of (1R, 2R)-trans-cyclohexane dicarboxylic acid |
| CN106316825A (en) * | 2016-08-24 | 2017-01-11 | 泰州精英化成医药科技有限公司 | Preparing method for trans- 4- hydroxycyclohexanecarboxylic acid |
| JP2022513714A (en) * | 2018-12-27 | 2022-02-09 | ハンワ ソリューションズ コーポレイション | Method for producing 1,4-cyclohexanedimethanol |
| JP7222092B2 (en) | 2018-12-27 | 2023-02-14 | ハンワ ソリューションズ コーポレイション | Method for producing 1,4-cyclohexanedimethanol |
| US11629112B2 (en) * | 2018-12-27 | 2023-04-18 | Hanwha Solutions Corporation | Method for preparation of 1,4-cyclohexanedimethanol |
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Application publication date: 20140129 |