CN101417973A - Method for preparing 2,3,5,6-tetra aminopyridine-2,5-dihydroxy terephthalate - Google Patents
Method for preparing 2,3,5,6-tetra aminopyridine-2,5-dihydroxy terephthalate Download PDFInfo
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- CN101417973A CN101417973A CNA2008101373437A CN200810137343A CN101417973A CN 101417973 A CN101417973 A CN 101417973A CN A2008101373437 A CNA2008101373437 A CN A2008101373437A CN 200810137343 A CN200810137343 A CN 200810137343A CN 101417973 A CN101417973 A CN 101417973A
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- aminopyridine
- phthalic acid
- dhta
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Abstract
The invention discloses a method for preparing 2, 3, 5, 6-tetrapyridylamine-2, 5-dihydroxyterephthalate, which relates to a method for preparing a complex by taking hydrochloride of 2, 3, 5, 6-tetrapyridylamine and 2, 5-dihydroxyterephthalic acid as raw materials. The method solves the problems of low purity and low yield existing in the prior TD salt preparation method. The method prepares the 2, 3, 5, 6-tetrapyridylamine-2, 5-dihydroxyterephthalate by complexing the hydrochloride of the 2, 3, 5, 6-tetrapyridylamine and the 2, 5-dihydroxyterephthalic acid. The method has the advantages of simple process, convenient operation, high purity, mild conditions, high yield, and easy industrialized production. The yield of TD salt prepared by the method is high up to 97 percent, and the purity of products is more than 99 percent.
Description
Technical field
The present invention relates to 2,3,5, the hydrochloride of 6-4-aminopyridine and 2, the 5-dihydric para-phthalic acid is the method for feedstock production complex compound.
Background technology
2,3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt (TD salt) be preparation poly-[2,5-dihydroxyl-1, one of 4-penylene pyrido diimidazole] (abbreviating PIPD as) weight raw material, yet there is the problem that purity is low, productive rate is low in existing TD salt preparation method.
Summary of the invention
The objective of the invention is to have the problem that purity is low, productive rate is low in order to solve existing TD salt preparation method; And provide 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt.
The solution of the present invention one: 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt: one, adding mass percent concentration in the reactor of sealing is 10%～30% sodium hydroxide solution, feeds nitrogen, stir with 30～50r/min rotating speed, add Sulfothiorine again, add 2 again, 5-dihydric para-phthalic acid (abbreviating DHTA as) after being heated to 50 ℃～80 ℃; Two, under nitrogen protection, with mass percent concentration be 8%～10% 2,3,5, the aqueous solution of the hydrochloride of 6-4-aminopyridine adds in the reactor, reacts 30min under 50 ℃ of conditions; Three, under nitrogen protection, drip while stirring with the rotating speed of 80～150r/min that mass percent concentration is 40%～50%, the phosphoric acid of nitrogen deoxidation is separated out yellow mercury oxide, dropwise the acetum adjust pH that adds the nitrogen deoxidation again, make the pH value less than 4; Four, ice bath is cooled to room temperature then, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of DHTA and sodium hydroxide is 1:4～6 in the step 1, and the Sulfothiorine consumption is 0.5～1% of a DHTA quality; In the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1～1.2:1; In the step 3 in the dripping quantity of phosphoric acid and the step 1 mol ratio of sodium hydroxide be 1:3～5, the rate of addition of phosphoric acid is 1～2mL/s.
The solution of the present invention two: 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is finished by following step: one, be 85% phosphoric acid with the mass percent concentration of nitrogen deoxidation with mass percent concentration be that 10%～30% sodium hydroxide solution mixes, regulate pH value to 4～5 then, mixing solutions is heated to 50～60 ℃; Two, under nitrogen protection, the sodium salt solution of DHTA and 2,3,5, the hydrochloric acid salt solution mix of 6-4-aminopyridine stirs with the rotating speed of 30～50r/min and to be warming up to 50 ℃, is incubated to solution becomes to clarify; Three, under nitrogen protection, the settled solution that step 2 is obtained adds in the mixing solutions that step 1 obtains, then with the mass percent concentration of nitrogen deoxidation be 85% phosphorus acid for adjusting pH value 4～5, separate out yellow mercury oxide; Four, ice bath is cooled to room temperature then, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of phosphoric acid and sodium hydroxide is 1:2～3 in the step 1; The sodium salt of DHTA and 2,3,5 in the step 2, mol ratio 1:1～1.2 of 6-4-aminopyridine hydrochloride; The sodium salt of DHTA and 2,3,5 in the step 2, the mol ratio of sodium hydroxide is 3～4:1 in 6-4-aminopyridine hydrochloride total mole number and the step 1.
The solution of the present invention three: 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is finished by following step: one, add mass percent concentration and be 10%～30% sodium hydroxide solution in reactor, feed nitrogen, rotating speed with 30～50r/min stirs, add Sulfothiorine again, add 2 again, the 5-dihydric para-phthalic acid after being heated to 95～100 ℃; Two, under nitrogen protection, with mass percent concentration be 18%～20% 2,3,5, the aqueous solution of the hydrochloride of 6-4-aminopyridine adds in the reactor, reacts 30min under 50 ℃ of conditions; Three, ice bath is cooled to room temperature, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of DHTA and sodium hydroxide is 1:3～3.5 in the step 1, and the Sulfothiorine quality is 0.5%～1% of a DHTA quality in the step 1; In the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1～1.2:1.
Method of the present invention have technology simple, be convenient to operation, mild condition, productive rate is high and be easy to the suitability for industrialized production advantage.The inventive method prepares TD salt productive rate up to 97%, and product purity is more than 99%.
Adopt method for preparing 2,3,5 of the present invention, 6-4-aminopyridine-2,5-dihydric para-phthalic acid salt (TD salt) polymerization prepares PIPD, saves the step that removes hydrogenchloride, shorten the reaction times, improve the molecular weight that makes PIPD, improved every performance of PIPD.
Description of drawings
Fig. 1 is the infrared spectrogram that embodiment one method makes TD salt.
Embodiment
Embodiment one: in the present embodiment 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is undertaken by following reaction: one, add mass percent concentration and be 10%～30% sodium hydroxide solution in the reactor of sealing, feed nitrogen, stir with 30～50r/min rotating speed, add Sulfothiorine again, add 2 again, the 5-dihydric para-phthalic acid after being heated to 50 ℃～80 ℃; Two, under nitrogen protection, with mass percent concentration be 8%～10% 2,3,5, the aqueous solution of the hydrochloride of 6-4-aminopyridine adds in the reactor, reacts 30min under 50 ℃ of conditions; Three, under nitrogen protection, drip while stirring with the rotating speed of 80～150r/min that mass percent concentration is 40%～50%, the phosphoric acid of nitrogen deoxidation is separated out yellow mercury oxide, dropwise the acetum adjust pH that adds the nitrogen deoxidation again, make the pH value less than 4; Four, ice bath is cooled to room temperature then, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of DHTA and sodium hydroxide is 1:4～6 in the step 1, and the Sulfothiorine consumption is 0.5～1% of a DHTA quality; In the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1～1.2:1; In the step 3 in the dripping quantity of phosphoric acid and the step 1 mol ratio of sodium hydroxide be 1:3～5, the rate of addition of phosphoric acid is 1～2mL/s.
After phosphoric acid dripped in the step 3 of present embodiment, reaction solution became and stirs easily.It is the xanchromatic pressed powder that present embodiment obtains product, and its productive rate is 97%, and its purity reaches more than 99%.Adopt present embodiment preparation 2,3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt (TD salt) polymerization prepares PIPD, saves the step that removes hydrogenchloride, shortens the reaction times, improves the molecular weight that makes PIPD, has improved every performance of PIPD.
Fig. 1 is the infrared spectrum of the TD salt that makes of present embodiment, at 3440cm
-1The spike at place is the absorption peak that phenolic hydroxyl group forms intramolecular hydrogen bond; 3120cm
-1The place is uncle ammonium salt-NH
+ 3The stretching vibration absorption peak, 2540cm
-1Place and 1880cm
-1The place is the frequency multiplication and the sum of fundamental frequencies absorption peak of uncle's ammonium salt; 1660cm
-1The absorption peak and the 787cm of place's medium tenacity
-1The strong absorption peak at place is the absorption peak of pyridine ring; 1580cm
-1The place is ammonium carboxylate salt antisymmetric stretching vibration absorption peak; 1500cm
-1Place and 1440cm
-1The place is the framework deformation vibration of phenyl ring and pyridine ring; 1250cm
-1The place is the phenolic hydroxyl group vibration absorption peak; 864cm
-1The place replaces characteristic peak for 1,2,4,5 of benzene.To the sign that the TD complexing salt for preparing carries out ultimate analysis, experimental value: W (C)=43.54%, W (H)=4.79%, W (N)=19.48%, theoretical value is that theoretical value is: W (C)=43.95%, W (H)=4.82%, W (N)=19.71%.Theoretical value and experimental value are identical substantially, and gap belongs to credible scope in 0.5% scope.Proof has obtained the TD complexing salt of expected structure thus, and purity is higher.
Embodiment two: what present embodiment and embodiment one were different is: the rotating speed with 100～130r/min in the step 3 stirs.Other is identical with embodiment one.
Embodiment three: what present embodiment and embodiment one were different is: the acetum adjust pH with the nitrogen deoxidation in the step 3 is 1～3.Other is identical with embodiment one.
Embodiment four: what present embodiment and embodiment one were different is: in the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1.1:1.Other is identical with embodiment one.
Embodiment five: in the present embodiment 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is undertaken by following reaction: one, be 85% phosphoric acid with the mass percent concentration of nitrogen deoxidation with mass percent concentration be that 10%～30% sodium hydroxide solution mixes, regulate pH value to 4～5 then, mixing solutions is heated to 50～60 ℃; Two, under nitrogen protection, the sodium salt solution of DHTA and 2,3,5, the hydrochloric acid salt solution mix of 6-4-aminopyridine stirs with the rotating speed of 30～50r/min and to be warming up to 50 ℃, is incubated to solution becomes to clarify; Three, under nitrogen protection, the settled solution that step 2 is obtained adds in the mixing solutions that step 1 obtains, then with the mass percent concentration of nitrogen deoxidation be 85% phosphorus acid for adjusting pH value 4～5, separate out yellow mercury oxide; Four, ice bath is cooled to room temperature then, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of phosphoric acid and sodium hydroxide is 1:2～3 in the step 1; The sodium salt of DHTA and 2,3,5 in the step 2, mol ratio 1:1～1.2 of 6-4-aminopyridine hydrochloride; The sodium salt of DHTA and 2,3,5 in the step 2, the mol ratio of sodium hydroxide is 3～4:1 in 6-4-aminopyridine hydrochloride total mole number and the step 1.
It is the xanchromatic pressed powder that present embodiment obtains product, and its productive rate is 95%, and its purity reaches more than 99%.Adopt present embodiment preparation 2,3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt (TD salt) and 2,3,5,6-4-aminopyridine (abbreviating TAP as) polymerization prepares PIPD, save the step that removes hydrogenchloride, shorten the reaction times, improve the molecular weight that makes PIPD, improved every performance of PIPD.
Embodiment six: what present embodiment and embodiment four were different is: the sodium salt of DHTA and 2,3,5 in the step 2, the mol ratio 1:1.1 of 6-4-aminopyridine hydrochloride.Other is identical with embodiment four.
Embodiment seven: in the present embodiment 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is undertaken by following reaction: one, add mass percent concentration and be 10%～30% sodium hydroxide solution in reactor, feed nitrogen, rotating speed with 30～50r/min stirs, add Sulfothiorine again, add 2 again, the 5-dihydric para-phthalic acid after being heated to 95～100 ℃; Two, under nitrogen protection, with mass percent concentration be 18%～20% 2,3,5, the aqueous solution of the hydrochloride of 6-4-aminopyridine adds in the reactor, reacts 30min under 50 ℃ of conditions; Three, ice bath is cooled to room temperature, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of DHTA and sodium hydroxide is 1:3～3.5 in the step 1, and the Sulfothiorine quality is 0.5%～1% of a DHTA quality in the step 1; In the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1～1.2:1.
It is the xanchromatic pressed powder that present embodiment obtains product, and its productive rate is 87%, and its purity reaches more than 99%.Adopt present embodiment preparation 2,3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt (TD salt) polymerization prepares PIPD, saves the step that removes hydrogenchloride, shortens the reaction times, improves the molecular weight that makes PIPD, has improved every performance of PIPD.
Embodiment eight: what present embodiment and embodiment seven were different is: in the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1.1:1.Other is identical with embodiment seven.
Claims (8)
1,2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is undertaken by following reaction: one, add mass percent concentration and be 10%～30% sodium hydroxide solution in the reactor of sealing, feed nitrogen, stir, add Sulfothiorine again with 30～50r/min rotating speed, add 2 again after being heated to 50 ℃～80 ℃, the 5-dihydric para-phthalic acid; Two, under nitrogen protection, with mass percent concentration be 8%～10% 2,3,5, the aqueous solution of the hydrochloride of 6-4-aminopyridine adds in the reactor, reacts 30min under 50 ℃ of conditions; Three, under nitrogen protection, drip while stirring with the rotating speed of 80～150r/min that mass percent concentration is 40%～50%, the phosphoric acid of nitrogen deoxidation is separated out yellow mercury oxide, dropwise the acetum adjust pH that adds the nitrogen deoxidation again, make the pH value less than 4; Four, ice bath is cooled to room temperature then, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of DHTA and sodium hydroxide is 1:4～6 in the step 1, and the Sulfothiorine consumption is 0.5～1% of a DHTA quality; In the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1～1.2:1; In the step 3 in the dripping quantity of phosphoric acid and the step 1 mol ratio of sodium hydroxide be 1:3～5, the rate of addition of phosphoric acid is 1～2mL/s.
2, according to claim 12,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that the rotating speed with 100～130r/min stirs in the step 3.
3, according to claim 12,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that the acetum adjust pH with the nitrogen deoxidation is 1～3 in the step 3.
4, according to claim 12,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that in the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1.1:1.
5,2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt, it is characterized in that 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is undertaken by following reaction: one, be 85% phosphoric acid with the mass percent concentration of nitrogen deoxidation with mass percent concentration be that 10%～30% sodium hydroxide solution mixes, regulate pH value to 4～5 then, mixing solutions is heated to 50～60 ℃; Two, under nitrogen protection, the sodium salt solution of DHTA and 2,3,5, the hydrochloric acid salt solution mix of 6-4-aminopyridine stirs with the rotating speed of 30～50r/min and to be warming up to 50 ℃, is incubated to solution becomes to clarify; Three, under nitrogen protection, the settled solution that step 2 is obtained adds in the mixing solutions that step 1 obtains, then with the mass percent concentration of nitrogen deoxidation be 85% phosphorus acid for adjusting pH value 4～5, separate out yellow mercury oxide; Four, ice bath is cooled to room temperature then, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of phosphoric acid and sodium hydroxide is 1:2～3 in the step 1; The sodium salt of DHTA and 2,3,5 in the step 2, mol ratio 1:1～1.2 of 6-4-aminopyridine hydrochloride; The sodium salt of DHTA and 2,3,5 in the step 2, the mol ratio of sodium hydroxide is 3～4:1 in 6-4-aminopyridine hydrochloride total mole number and the step 1.
6, according to claim 52,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that the sodium salt and 2,3,5 of DHTA in the step 2, the mol ratio 1:1.1 of 6-4-aminopyridine hydrochloride.
7,2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that 2,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is undertaken by following reaction: one, add mass percent concentration and be 10%～30% sodium hydroxide solution in reactor, feed nitrogen, the rotating speed stirring with 30～50r/min adds Sulfothiorine again, add 2 again after being heated to 95～100 ℃, the 5-dihydric para-phthalic acid; Two, under nitrogen protection, with mass percent concentration be 18%～20% 2,3,5, the aqueous solution of the hydrochloride of 6-4-aminopyridine adds in the reactor, reacts 30min under 50 ℃ of conditions; Three, ice bath is cooled to room temperature, under nitrogen protection, carry out suction filtration, use the water washing three to five times of nitrogen deoxidation then, use the washing with alcohol three to five times of nitrogen deoxidation again, change in the vacuum drying oven dry 20～24h under 50 ℃ of conditions again over to drying up then, promptly obtain 2 with nitrogen gas stream, 3,5,6-4-aminopyridine-2,5-dihydric para-phthalic acid salt; The mol ratio of DHTA and sodium hydroxide is 1:3～3.5 in the step 1, and the Sulfothiorine quality is 0.5%～1% of a DHTA quality in the step 1; In the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1～1.2:1.
8, according to claim 52,3,5,6-4-aminopyridine-2, the preparation method of 5-dihydric para-phthalic acid salt is characterized in that in the step 22,3,5, the hydrochloride of 6-4-aminopyridine and the mol ratio of DHTA are 1.1:1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103588703A (en) * | 2013-11-29 | 2014-02-19 | 中蓝晨光化工研究设计院有限公司 | Preparation method of 2,3,5,6-tetraaminopyridine phosphate |
| CN114920688A (en) * | 2022-05-05 | 2022-08-19 | 东华大学 | Method for preparing 2,3,5, 6-tetraaminopyridine-2, 5-dihydroxy terephthalate |
-
2008
- 2008-10-17 CN CNA2008101373437A patent/CN101417973A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103588703A (en) * | 2013-11-29 | 2014-02-19 | 中蓝晨光化工研究设计院有限公司 | Preparation method of 2,3,5,6-tetraaminopyridine phosphate |
| CN103588703B (en) * | 2013-11-29 | 2015-08-05 | 中蓝晨光化工研究设计院有限公司 | A kind of 2,3,5,6-4-aminopyridine method for production of phosphate salt |
| CN114920688A (en) * | 2022-05-05 | 2022-08-19 | 东华大学 | Method for preparing 2,3,5, 6-tetraaminopyridine-2, 5-dihydroxy terephthalate |
| CN114920688B (en) * | 2022-05-05 | 2024-06-18 | 东华大学 | Method for preparing 2,3,5, 6-tetra-aminopyridine-2, 5-dihydroxyterephthalic acid salt |
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