CN101531612A - Method for preparing phthalandione monoamide carboxylate - Google Patents
Method for preparing phthalandione monoamide carboxylate Download PDFInfo
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- CN101531612A CN101531612A CN200910136024A CN200910136024A CN101531612A CN 101531612 A CN101531612 A CN 101531612A CN 200910136024 A CN200910136024 A CN 200910136024A CN 200910136024 A CN200910136024 A CN 200910136024A CN 101531612 A CN101531612 A CN 101531612A
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- phthalandione
- carboxylate
- phthalandione monoamide
- monoamide
- reaction
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Abstract
The invention provides a preparing method which uses phthalandione and alkylamine for synthesizing phthalandione monoamide carboxylate. The method belongs to the organic compound synthesis field. The method includes steps as follows: utilizing phthalic anhydride and alkylamine amidating for generating phthalandione monoamide, then neutralizing to phthalandione monoamide carboxylate by alkali. The method has simple synthesizing route, and can obtain surface active agent with excellent performance which is suitable for applying in rigor conditions of acid-alkali and high temperature.
Description
Technical field
The present invention relates to a kind of preparation method who synthesizes phthalandione monoamide carboxylate with Tetra hydro Phthalic anhydride and alkylamine.
Background technology
With alkyl alcohol and Tetra hydro Phthalic anhydride is the synthetic phthalic monoester of raw material, again in and salify belong to the alkyl alcohol series of surfactants.Phthalic acid list alcohol ester carboxylate salt has more excellent physical and chemical performance than other tensio-active agents of alkyl alcohol series.Yet the ester group in this type of surfactant molecule structure than facile hydrolysis, has influenced the stable performance of its application performance under acid-alkali medium and hot conditions.
Replace the synthetic phthalandione monoamide carboxylate of ester group to have good stability with amide group, surfactivity excellence, advantage such as synthetic route is simple, domestic not appearing in the newspapers at present.
Summary of the invention
The objective of the invention is to overcome the deficiency of phthalic monoester carboxylate salt stability, synthetic a kind of stable and have an excellent surface-active phthalandione monoamide carboxylate under acid-alkali medium and hot conditions.
The chemical structural formula of phthalandione monoamide carboxylate of the present invention is as follows:
In the formula: R is C
1～C
22Saturated, unsaturated, straight chain, the alkyl of side chain;
M is Na
+, K
+, NH
4 +Deng.
Synthetic method of the present invention is to utilize Tetra hydro Phthalic anhydride and alkylamine amidate action to generate phthalandione monoamide, is neutralized into phthalandione monoamide carboxylate with alkali again.
The synthetic method of described phthalandione monoamide is to be that raw material carries out in reaction vessel with the Tetra hydro Phthalic anhydride, and the mol ratio of Tetra hydro Phthalic anhydride and alkylamine is: 1:2～5:1, and temperature of reaction is-50～130 ℃, the reaction times is 1～600min.Reaction formula is as follows:
The synthetic method of described phthalandione monoamide salt is phthalandione monoamide and alkali neutralization, and the mol ratio of phthalandione monoamide and alkali is: 1:1～1:5, and temperature of reaction is 0～100 ℃, the reaction times is 1～600min.Reaction formula is as follows:
Synthetic phthalandione monoamide carboxylate anion surfactant of the present invention has more excellent surface activity, has avoided phthalic monoester carboxylate salt unsettled limitation under soda acid or hot conditions, has good practical value is more arranged.
Embodiment
Below in conjunction with embodiment the present invention is made an explanation.
Embodiment 1
Take by weighing 22.2g Tetra hydro Phthalic anhydride and 18.5g lauryl amine, join in the 250ml flask, add the 100ml solvent, slowly be warming up to 75 ℃, stirring reaction 3h, reaction naturally cools to room temperature after finishing, decompress filter is collected product, and recrystallization gets phthalic acid list laurylamide white solid.The phthalic acid list laurylamide that obtains is water-soluble, add the 4g sodium hydrate solid, 40 ℃ were stirred 20 minutes, after reaction finishes, concentrated, and recrystallization obtains phthalic acid list laurylamide carboxylic acid and receives.
Embodiment 2
Take by weighing 29.6g Tetra hydro Phthalic anhydride and 18.5g lauryl amine, join in the 250ml flask, add the 100ml solvent, slowly be warming up to 75 ℃, stirring reaction 4h, reaction naturally cools to room temperature after finishing, decompress filter is collected product, and recrystallization gets phthalic acid list laurylamide white solid.The phthalic acid list laurylamide that obtains is water-soluble, add the 4g sodium hydrate solid, 40 ℃ were stirred 20 minutes, after reaction finishes, concentrated, and recrystallization obtains phthalic acid list laurylamide carboxylic acid and receives.
Embodiment 3
Take by weighing 22.2g Tetra hydro Phthalic anhydride and 20.9g tetradecy lamine, join in the 250ml flask, add the 100ml solvent, slowly be warming up to 80 ℃, stirring reaction 3h, reaction naturally cools to room temperature after finishing, decompress filter is collected product, and recrystallization gets phthalic acid list myristamide white solid.The phthalic acid list myristamide that obtains is water-soluble, add 5.6g potassium hydroxide solid, 40 ℃ were stirred 20 minutes, after reaction finishes, concentrated, and recrystallization obtains phthalic acid list myristamide carboxylic acid potassium.
Embodiment 4
Take by weighing 29.6g Tetra hydro Phthalic anhydride and 20.9g tetradecy lamine, join in the 250ml flask, add the 100ml solvent, slowly be warming up to 80 ℃, stirring reaction 3.5h, reaction naturally cools to room temperature after finishing, decompress filter is collected product, and recrystallization gets phthalic acid list myristamide white solid.The phthalic acid list myristamide that obtains is water-soluble, add 5.6g potassium hydroxide solid, 40 ℃ were stirred 20 minutes, after reaction finishes, concentrated, and recrystallization obtains phthalic acid list myristamide carboxylic acid potassium.
Embodiment 5
Take by weighing 22.2g Tetra hydro Phthalic anhydride and 26.9g stearylamine, join in the 250ml flask, add the 100ml solvent, slowly be warming up to 80 ℃, stirring reaction 4h, reaction naturally cools to room temperature after finishing, decompress filter is collected product, and recrystallization gets phthalic acid list stearylamide white solid.The phthalic acid list stearylamide that obtains is water-soluble, add 5.6g potassium hydroxide solid, 40 ℃ were stirred 20 minutes, after reaction finishes, concentrated, and recrystallization obtains phthalic acid list stearylamide carboxylic acid potassium.
Embodiment 6
Take by weighing 29.6g Tetra hydro Phthalic anhydride and 26.9g stearylamine, join in the 250ml flask, add the 100ml solvent, slowly be warming up to 80 ℃, stirring reaction 3h, reaction naturally cools to room temperature after finishing, decompress filter is collected product, and recrystallization gets phthalic acid list stearylamide white solid.The phthalic acid list stearylamide that obtains is water-soluble, add 5.6g potassium hydroxide solid, 40 ℃ were stirred 20 minutes, after reaction finishes, concentrated, and recrystallization obtains phthalic acid list stearylamide carboxylic acid potassium.
Claims (8)
1. phthalandione monoamide carboxylate is characterized in that chemical structural formula is as follows:
In the formula: R is C
1～C
22Saturated, unsaturated, straight chain, the alkyl of side chain;
M is Na
+, K
+, NH
4 +Deng.
2. phthalandione monoamide carboxylate according to claim 1 is characterized in that: the gegenion of carboxylate salt partly is Na
+, K
+, NH
4 +Deng.
3. phthalandione monoamide carboxylate according to claim 1 is characterized in that: alkyl R is C
1～C
22Saturated, unsaturated, straight chain, the alkyl of side chain.
4. phthalandione monoamide carboxylate according to claim 1 is characterized in that: with Tetra hydro Phthalic anhydride and alkylamine is that amidation reagent synthesizes phthalandione monoamide, is neutralized into phthalandione monoamide carboxylate with alkali again.
5. phthalandione monoamide carboxylate synthetic method according to claim 1 is characterized in that: Tetra hydro Phthalic anhydride and alkylamine generation amidate action, and synthetic phthalandione monoamide, the building-up reactions formula is as follows:
6. phthalandione monoamide carboxylate synthetic method according to claim 4 is characterized in that: phthalandione monoamide and various alkali reaction, synthetic gegenion are Na
+, K
+, NH
4 +Deng phthalandione monoamide carboxylate, the building-up reactions formula is as follows:
7. the synthetic method of phthalandione monoamide according to claim 5, it is characterized in that comprising following reaction conditions: the mol ratio of Tetra hydro Phthalic anhydride and alkylamine is: 1:2～5:1, temperature of reaction is-50～130 ℃, the reaction times is 1～600min.
8. the synthetic method of phthalandione monoamide carboxylate according to claim 6, it is characterized in that comprising following reaction conditions: the mol ratio of phthalandione monoamide and alkali is: 1:1～1:5, temperature of reaction is 0～100 ℃, and the reaction times is 1～600min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910136024A CN101531612A (en) | 2009-04-24 | 2009-04-24 | Method for preparing phthalandione monoamide carboxylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910136024A CN101531612A (en) | 2009-04-24 | 2009-04-24 | Method for preparing phthalandione monoamide carboxylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101531612A true CN101531612A (en) | 2009-09-16 |
Family
ID=41102494
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910136024A Pending CN101531612A (en) | 2009-04-24 | 2009-04-24 | Method for preparing phthalandione monoamide carboxylate |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669490A (en) * | 2016-01-15 | 2016-06-15 | 辽宁石油化工大学 | Phthalic acid derivative gelator and preparation method and application thereof |
| CN111333532A (en) * | 2020-04-09 | 2020-06-26 | 江苏顶塑实业有限公司 | N-alkyl phthalic diamide acid derivative and synthetic method and application thereof |
| CN111468032A (en) * | 2020-05-28 | 2020-07-31 | 江南大学 | Easily soluble/cleavable/self-thickening surfactant and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991001970A2 (en) * | 1989-08-08 | 1991-02-21 | Stepan Company | Cyclic amidocarboxy surfactants, synthesis and use thereof |
-
2009
- 2009-04-24 CN CN200910136024A patent/CN101531612A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991001970A2 (en) * | 1989-08-08 | 1991-02-21 | Stepan Company | Cyclic amidocarboxy surfactants, synthesis and use thereof |
Non-Patent Citations (1)
| Title |
|---|
| JOHN W. VERBICKY，JR ET AL: "Thermolysis of N-Alkyl-Substituted Phthalamic acids.Steric inhibition of imide formation", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669490A (en) * | 2016-01-15 | 2016-06-15 | 辽宁石油化工大学 | Phthalic acid derivative gelator and preparation method and application thereof |
| CN111333532A (en) * | 2020-04-09 | 2020-06-26 | 江苏顶塑实业有限公司 | N-alkyl phthalic diamide acid derivative and synthetic method and application thereof |
| CN111333532B (en) * | 2020-04-09 | 2022-09-16 | 江苏顶塑实业有限公司 | N-alkyl phthalic diamide acid derivative and synthetic method and application thereof |
| CN111468032A (en) * | 2020-05-28 | 2020-07-31 | 江南大学 | Easily soluble/cleavable/self-thickening surfactant and preparation method thereof |
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Application publication date: 20090916 |