CN113880709A - Preparation method of high-purity 2-hydroxy-6-naphthoic acid - Google Patents
Preparation method of high-purity 2-hydroxy-6-naphthoic acid Download PDFInfo
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- CN113880709A CN113880709A CN202111348950.XA CN202111348950A CN113880709A CN 113880709 A CN113880709 A CN 113880709A CN 202111348950 A CN202111348950 A CN 202111348950A CN 113880709 A CN113880709 A CN 113880709A
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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
- C07C51/41—Preparation of salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
- C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
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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
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
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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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of high-purity 2-hydroxy-6-naphthoic acid, which comprises the following steps: 1) mixing 2-phenol, alkali liquor and an organic solvent, and salifying and dehydrating to obtain a mixture; 2) drying, carbonizing and carrying out chromatographic separation on the mixture to obtain a crude product; 3) mixing the crude product, activated carbon and petroleum ether, heating and refluxing, filtering, adjusting the pH value to 5-6, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid. The preparation method has low cost and simple steps, and the prepared 2-hydroxy-6-naphthoic acid has high purity and excellent quality and can meet the requirement of high-purity monomers required by polymer reaction.
Description
Technical Field
The invention relates to the field of production of organic chemical intermediates, in particular to a preparation method of high-purity 2-hydroxy-6-naphthoic acid.
Background
Liquid Crystal Polymer (LCP) is a high performance polymer material generally known for its high strength, high modulus, excellent melt processing characteristics, flame retardancy, low water absorption, chemical resistance and radiation resistance. The method is widely applied to the fields of packaging materials, electronic communication and the like.
2-hydroxy-6-naphthoic acid is used as a main monomer for synthesizing liquid crystal polymer materials, and the demand is also rapidly increasing. The application of the 2-hydroxy-6-naphthoic acid has higher purity requirement. The existing preparation process related to the 2-hydroxy-6-naphthoic acid has more side reactions, is easy to introduce impurities, and the quality of the obtained 2-hydroxy-6-naphthoic acid is not high.
Disclosure of Invention
In view of the above-mentioned disadvantages of the prior art, the present invention aims to provide a process for producing 2-hydroxy-6-naphthoic acid with high purity, which is intended to obtain 2-hydroxy-6-naphthoic acid with excellent quality and purity higher than 99.9%.
In order to achieve the purpose, the invention is realized by the following technical scheme:
a preparation method of high-purity 2-hydroxy-6-naphthoic acid is characterized by comprising the following steps:
1) mixing 2-phenol, alkali liquor and an organic solvent, and salifying and dehydrating to obtain a mixture;
2) drying, carbonizing and carrying out chromatographic separation on the mixture to obtain a crude product;
3) mixing the crude product, activated carbon and petroleum ether, heating and refluxing, filtering, adjusting the pH value to 5-6, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
The preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the following steps of (1) preparing 2-phenol, an organic solution and an alkali liquor in a weight ratio of 1.5-2:2-4: 1;
the preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the following steps of (1) preparing an alkali solution by using a sodium hydroxide solution and/or a potassium hydroxide solution, wherein the concentration of the alkali solution is 20-40 wt%;
the preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the following steps of salt formation and dehydration: heating to 160-180 ℃ and 0.1-0.2MPa, stirring for 1-3h, and heating to 200-210 ℃ for reaction for 1-2 h.
The preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the steps of carrying out chromatographic separation on eluent of petroleum ether-acetone-diethylamine, and carrying out chromatographic column on alumina column.
The preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the following steps of: heating to 230 ℃ and 240 ℃ at the speed of 1-2 ℃/min, stirring for 2-3h, and keeping the vacuum degree at 0.1-0.2 MPa.
The preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the following steps of mixing a crude product, activated carbon and petroleum ether in a mass ratio of 1: 0.1-0.2: 50-100.
The preparation method of the high-purity 2-hydroxy-6-naphthoic acid comprises the steps of heating and refluxing at 70-80 ℃ for 8-12 hours.
The preparation method of the high-purity 2-hydroxy-6-naphthoic acid is characterized in that the purity of the high-purity 2-hydroxy-6-naphthoic acid is higher than 99.9%.
Has the advantages that: the invention discloses a preparation method of high-purity 2-hydroxy-6-naphthoic acid, which controls the dosage of raw materials and reduces the occurrence of side reactions by improving parameters of a Kolbe-Schmidt reaction; then carrying out chromatographic separation to obtain a crude product of the 2-hydroxy-6-naphthoic acid; finally, purifying the 2-hydroxy-6-naphthoic acid by recrystallization. The preparation method has low cost and simple steps, and the prepared 2-hydroxy-6-naphthoic acid has high purity and excellent quality and can meet the requirement of high-purity monomers required by polymer reaction.
Detailed Description
The present invention provides a method for preparing high-purity 2-hydroxy-6-naphthoic acid, which is further described in detail below in order to make the objects, technical solutions and effects of the present invention clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Specifically, the invention provides a preparation method of high-purity 2-hydroxy-6-naphthoic acid, which comprises the following steps:
1) mixing 2-phenol, an organic solution and an alkali liquor according to a weight ratio of 1.5-2:2-4:1, placing the mixture in a salt forming kettle, heating to 160-180 ℃ and a pressure of 0.1-0.2MPa, stirring for 1-3h, heating to 200-210 ℃ for reaction for 1-2h, and performing salt formation and dehydration to obtain a mixture;
wherein the alkali solution is sodium hydroxide solution and/or potassium hydroxide solution, and the concentration is 20-40 wt%.
2) Placing the mixture in a carbonization kettle, heating to 230-240 ℃ at the speed of 1-2 ℃/min, stirring for 2-3h, and carrying out drying carbonization and chromatographic separation under the condition that the vacuum degree is 0.1-0.2MPa to obtain a crude product;
wherein the eluent for chromatographic separation is petroleum ether-acetone-diethylamine, and the chromatographic column is an alumina column.
3) Mixing the crude product, the activated carbon and the petroleum ether according to the mass ratio of 1: 0.1-0.2: mixing 50-100 parts, heating and refluxing at 70-80 ℃ for 8-12h, filtering, adjusting the pH value to 5-6, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
The purity of the high-purity 2-hydroxy-6-naphthoic acid is higher than 99.9 percent.
The process for preparing high purity 2-hydroxy-6-naphthoic acid according to the present invention is further illustrated by the following specific examples:
example 1
One embodiment of the present invention provides a method for preparing high-purity 2-hydroxy-6-naphthoic acid, comprising the steps of:
1) mixing 150 parts of 2-phenol, 200 parts of organic solution and 10 parts of 20 wt% sodium hydroxide solution, placing the mixture in a salt forming kettle, heating to 160 ℃, stirring for 3 hours under the condition of 0.1MPa of pressure, heating to 200 ℃ again, reacting for 2 hours, salifying and dehydrating to obtain a mixture.
2) And (3) putting the mixture into a carbonization kettle, heating to 230 ℃ at the speed of 1 ℃/min, stirring for 3h under the condition that the vacuum degree is 0.2MPa, drying and carbonizing, and performing chromatographic separation by using an alumina column and petroleum ether-acetone-diethylamine eluent to obtain a crude product.
3) Heating and refluxing the 10 parts of crude product, 1 part of activated carbon and 500 parts of petroleum ether at 70 ℃ for 12 hours, filtering, adjusting the pH value to 6, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
The purity of the high-purity 2-hydroxy-6-naphthoic acid of example 1 is higher than 99.9% by detection.
Example 2
One embodiment of the present invention provides a method for preparing high-purity 2-hydroxy-6-naphthoic acid, comprising the steps of:
1) mixing 200 parts of 2-phenol, 400 parts of organic solution and 10 parts of 40 wt% sodium hydroxide solution, placing the mixture in a salt forming kettle, heating to 180 ℃, stirring for 1h under the condition of 0.2MPa of pressure, heating to 210 ℃, reacting for 1h, salifying and dehydrating to obtain a mixture.
2) And (3) putting the mixture into a carbonization kettle, heating to 240 ℃ at the speed of 2 ℃/min, stirring for 2h under the condition that the vacuum degree is 0.1MPa, drying and carbonizing, and performing chromatographic separation by using an alumina column and petroleum ether-acetone-diethylamine eluent to obtain a crude product.
3) And heating and refluxing the 10 parts of crude product, 2 parts of activated carbon and 1000 parts of petroleum ether at 80 ℃ for 8 hours, filtering, adjusting the pH value to 5, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
The purity of the high-purity 2-hydroxy-6-naphthoic acid of the example 2 is higher than 99.9 percent through detection.
Example 3
One embodiment of the present invention provides a method for preparing high-purity 2-hydroxy-6-naphthoic acid, comprising the steps of:
1) mixing 180 parts of 2-phenol, 300 parts of organic solution and 10 parts of 30 wt% potassium hydroxide solution, placing the mixture in a salt forming kettle, heating to 170 ℃, stirring for 1h under the condition of 0.2MPa of pressure, heating to 210 ℃, reacting for 2h, salifying and dehydrating to obtain a mixture.
2) And (3) putting the mixture into a carbonization kettle, heating to 240 ℃ at the speed of 1 ℃/min, stirring for 3h under the condition that the vacuum degree is 0.2MPa, drying and carbonizing, and performing chromatographic separation by using an alumina column and petroleum ether-acetone-diethylamine eluent to obtain a crude product.
3) And heating and refluxing the 10 parts of crude product, 2 parts of activated carbon and 500 parts of petroleum ether at 80 ℃ for 12 hours, filtering, adjusting the pH value to 6, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
The purity of the high-purity 2-hydroxy-6-naphthoic acid of example 3 is higher than 99.9% by detection.
Example 4
One embodiment of the present invention provides a method for preparing high-purity 2-hydroxy-6-naphthoic acid, comprising the steps of:
1) mixing 200 parts of 2-phenol, 300 parts of organic solution and 10 parts of 30 wt% sodium hydroxide solution, placing the mixture in a salt forming kettle, heating to 160 ℃, stirring for 2 hours under the condition of 0.2MPa of pressure, heating to 210 ℃, reacting for 1 hour, salifying and dehydrating to obtain a mixture.
2) And (3) putting the mixture into a carbonization kettle, heating to 240 ℃ at the speed of 1 ℃/min, stirring for 2h under the condition that the vacuum degree is 0.2MPa, drying and carbonizing, and performing chromatographic separation by using an alumina column and petroleum ether-acetone-diethylamine eluent to obtain a crude product.
3) And heating and refluxing the 10 parts of crude product, 2 parts of activated carbon and 1000 parts of petroleum ether at 70 ℃ for 8 hours, filtering, adjusting the pH value to 5, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
The purity of the high-purity 2-hydroxy-6-naphthoic acid of the example 2 is higher than 99.9 percent through detection.
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.
Claims (9)
1. A preparation method of high-purity 2-hydroxy-6-naphthoic acid is characterized by comprising the following steps:
1) mixing 2-phenol, alkali liquor and an organic solvent, and salifying and dehydrating to obtain a mixture;
2) drying, carbonizing and carrying out chromatographic separation on the mixture to obtain a crude product;
3) mixing the crude product, activated carbon and petroleum ether, heating and refluxing, filtering, adjusting the pH value to 5-6, distilling and drying to obtain the high-purity 2-hydroxy-6-naphthoic acid.
2. The method of claim 1, wherein the weight ratio of the 2-phenol, the organic solution and the alkali solution is 1.5-2:2-4: 1.
3. The method for preparing high-purity 2-hydroxy-6-naphthoic acid according to claim 1, wherein said alkali solution is sodium hydroxide solution and/or potassium hydroxide solution, and has a concentration of 20 to 40 wt%.
4. The method for preparing high-purity 2-hydroxy-6-naphthoic acid according to claim 1, wherein said salt-forming dehydration comprises: heating to 160-180 ℃ and 0.1-0.2MPa, stirring for 1-3h, and heating to 200-210 ℃ for reaction for 1-2 h.
5. The method for preparing high-purity 2-hydroxy-6-naphthoic acid according to claim 1, wherein said drying and carbonizing conditions comprise: heating to 230 ℃ and 240 ℃ at the speed of 1-2 ℃/min, stirring for 2-3h, and keeping the vacuum degree at 0.1-0.2 MPa.
6. The method of claim 1, wherein the eluent for chromatographic separation is petroleum ether-acetone-diethylamine, and the chromatographic column is an alumina column.
7. The method for preparing high-purity 2-hydroxy-6-naphthoic acid according to claim 1, wherein the mass ratio of the crude product, the activated carbon and the petroleum ether is 1: 0.1-0.2: 50-100.
8. The method for preparing high-purity 2-hydroxy-6-naphthoic acid according to claim 1, wherein said heating under reflux is carried out at a temperature of 70 to 80 ℃ for 8 to 12 hours.
9. The method of claim 1, wherein the purity of the high-purity 2-hydroxy-6-naphthoic acid is higher than 99.9%.
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Citations (9)
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|---|---|---|---|---|
| CN1064072A (en) * | 1991-10-14 | 1992-09-02 | 上海新顺化工厂 | The preparation method of 2 hydroxyls-3 naphthoic acid of content 99% |
| JPH10120624A (en) * | 1996-10-18 | 1998-05-12 | Sugai Kagaku Kogyo Kk | Purification of 2-hydroxymephthalene-6-carboxylic acid |
| US5770766A (en) * | 1995-11-13 | 1998-06-23 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Method for separating and purifying hydroxynaphtalenecarboxylic acids |
| US6124498A (en) * | 1995-04-28 | 2000-09-26 | University Of New Mexico | Hydroxynaphthoic acids and derivatives |
| TW467886B (en) * | 1996-05-15 | 2001-12-11 | Du Pont | Preparation of aromatic hydroxycarboxylic acids and dialkali metal salts thereof |
| JP2004256448A (en) * | 2003-02-26 | 2004-09-16 | Daicel Chem Ind Ltd | Method for decoloring 6-hydroxy-2-naphthoic acid |
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| CN102173988A (en) * | 2011-03-25 | 2011-09-07 | 衢州英特高分子材料有限公司 | Purification method of 6-hydroxyl-2-naphthoic acid |
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-
2021
- 2021-11-15 CN CN202111348950.XA patent/CN113880709A/en active Pending
Patent Citations (9)
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| CN1064072A (en) * | 1991-10-14 | 1992-09-02 | 上海新顺化工厂 | The preparation method of 2 hydroxyls-3 naphthoic acid of content 99% |
| US6124498A (en) * | 1995-04-28 | 2000-09-26 | University Of New Mexico | Hydroxynaphthoic acids and derivatives |
| US5770766A (en) * | 1995-11-13 | 1998-06-23 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Method for separating and purifying hydroxynaphtalenecarboxylic acids |
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| JP2004256448A (en) * | 2003-02-26 | 2004-09-16 | Daicel Chem Ind Ltd | Method for decoloring 6-hydroxy-2-naphthoic acid |
| JP2007169237A (en) * | 2005-12-26 | 2007-07-05 | Teijin Ltd | Method for purifying 6,6'-(ethylenedioxy)di-2-naphthoic acid |
| CN102173988A (en) * | 2011-03-25 | 2011-09-07 | 衢州英特高分子材料有限公司 | Purification method of 6-hydroxyl-2-naphthoic acid |
| CN112707808A (en) * | 2020-12-25 | 2021-04-27 | 宿迁思睿屹新材料有限公司 | Preparation process of 2-hydroxy-6-naphthoic acid |
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