CN111747840A - Preparation method of 1, 4-naphthalenedicarboxylic acid - Google Patents
Preparation method of 1, 4-naphthalenedicarboxylic acid Download PDFInfo
- Publication number
- CN111747840A CN111747840A CN202010704455.7A CN202010704455A CN111747840A CN 111747840 A CN111747840 A CN 111747840A CN 202010704455 A CN202010704455 A CN 202010704455A CN 111747840 A CN111747840 A CN 111747840A
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- CN
- China
- Prior art keywords
- methyl
- acetonaphthone
- preparation
- oxygen
- naphthalenedicarboxylic acid
- Prior art date
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- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims description 31
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 15
- 229940011182 cobalt acetate Drugs 0.000 claims description 14
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 14
- 229940071125 manganese acetate Drugs 0.000 claims description 14
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229960000583 acetic acid Drugs 0.000 claims description 11
- 239000012043 crude product Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 239000012362 glacial acetic acid Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000012452 mother liquor Substances 0.000 claims description 8
- 229940094035 potassium bromide Drugs 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BKGIZYOJHJKFJP-UHFFFAOYSA-N 1-(4-methylnaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=C(C)C2=C1 BKGIZYOJHJKFJP-UHFFFAOYSA-N 0.000 abstract description 7
- SIVYRLBDAPKADZ-UHFFFAOYSA-N 4-methylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C)=CC=C(C(O)=O)C2=C1 SIVYRLBDAPKADZ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000007858 starting material Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000003916 acid precipitation Methods 0.000 description 4
- 238000004042 decolorization Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- -1 1-methyl-4-naphthone Chemical compound 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
Abstract
The invention belongs to the technical field of organic synthesis, and provides a preparation method of 1, 4-naphthalenedicarboxylic acid. The 1, 4-naphthalene dicarboxylic acid is prepared by directly oxidizing 1-methyl-4-acetonaphthone serving as a starting material with oxygen, and the preparation steps are simple and easy to operate; the preparation method provided by the invention solves the problem of raw material supply, the price of the 1-methyl-4-naphthyl ethanone is 5 ten thousand yuan lower than that of the 1-methyl-4-naphthoic acid per ton, the total cost of the 1, 4-naphthalenedicarboxylic acid can be reduced by 4 ten thousand yuan, and the preparation method has good economic benefit.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1, 4-naphthalenedicarboxylic acid.
Background
The 1, 4-naphthalene dicarboxylic acid has wide application in chemical production, and can be particularly used as an intermediate of a dye and a plastic processing aid or used for producing a fluorescent whitening agent, a dye intermediate and the like.
In the prior art, 1-methyl-4-naphthoic acid is used as a starting material to prepare 1, 4-naphthalenedicarboxylic acid, 1-methyl-4-naphthoic acid is obtained by reacting 1-methyl-4-naphthone with sodium hypochlorite, a byproduct chloroform is generated in the reaction process, and a large amount of salt-containing wastewater is generated, so that the purchasing price of 1-methyl-4-naphthoic acid is higher and higher along with the stricter environmental protection requirement and the increase of environmental protection cost, and the 1-methyl-4-naphthoic acid is difficult to buy in the current market, so that the market demand of the 1, 4-naphthalenedicarboxylic acid is directly influenced.
Disclosure of Invention
In view of the above, the present invention provides a novel process for preparing 1, 4-naphthalenedicarboxylic acid. The method provided by the invention uses 1-methyl-4-acetonaphthone as the starting material, and the 1, 4-naphthalenedicarboxylic acid is prepared by directly oxidizing with oxygen, so that the problem of raw material supply is solved, and the price of the 1-methyl-4-acetonaphthone is lower than that of the 1-methyl-4-naphthoic acid, so that the economic benefit is better.
In order to achieve the above object, the present invention provides the following technical solutions:
a method for preparing 1, 4-naphthalenedicarboxylic acid, comprising the steps of:
mixing 1-methyl-4-acetonaphthone, a solvent and a catalyst, and introducing oxygen into the obtained mixed solution to perform oxidation reaction on the 1-methyl-4-acetonaphthone to obtain 1, 4-naphthalenedicarboxylic acid; the catalyst comprises cobalt acetate, manganese acetate and potassium bromide; the solvent is glacial acetic acid.
Preferably, the mass ratio of the 1-methyl-4-acetonaphthone, the cobalt acetate, the manganese acetate, the potassium bromide, the glacial acetic acid and the oxygen is 100 (3-5): 3-5: (1400-1600): 80-100.
Preferably, the mass ratio of the 1-methyl-4-acetonaphthone, the cobalt acetate, the manganese acetate, the potassium bromide, the glacial acetic acid and the oxygen is 100:4:4:4:1500: 90.
Preferably, the introduction rate of the oxygen is 3-5 cubic meters per hour.
Preferably, the temperature of the oxidation reaction is 90-100 ℃.
Preferably, after the oxidation reaction is completed, the method further comprises post-treating the obtained product liquid, wherein the post-treating comprises the following steps:
(1) cooling the product liquid, and performing solid-liquid separation to obtain a crude product;
(2) and sequentially carrying out alkalization salt formation, decoloration, acidification, solid-liquid separation, water washing, solid-liquid separation again and drying on the crude product to obtain the 1, 4-naphthalenedicarboxylic acid.
Preferably, the decolorizing agent is activated carbon.
Preferably, the mother liquor generated in the solid-liquid separation in the step (1) is recycled; the recycling method comprises the following steps: and adding acetic anhydride, cobalt acetate, manganese acetate and potassium bromide into the mother liquor, and then adding 1-methyl-4-acetonaphthone to perform the next batch of reaction.
The invention provides a preparation method of 1, 4-naphthalenedicarboxylic acid, which takes 1-methyl-4-acetonaphthone as a starting material and prepares the 1, 4-naphthalenedicarboxylic acid directly by oxygen oxidation, and the preparation steps are simple and easy to operate; the preparation method provided by the invention solves the problem of raw material supply, the price of the 1-methyl-4-naphthyl ethanone is 5 ten thousand yuan lower than that of the 1-methyl-4-naphthoic acid per ton, the total cost of the 1, 4-naphthalenedicarboxylic acid can be reduced by 4 ten thousand yuan, and the preparation method has good economic benefit.
Detailed Description
The invention provides a preparation method of 1, 4-naphthalenedicarboxylic acid, which comprises the following steps:
mixing 1-methyl-4-acetonaphthone, solvent and catalyst, and introducing oxygen into the obtained mixed solution to perform oxidation reaction on the 1-methyl-4-acetonaphthone to obtain 1, 4-naphthalenedicarboxylic acid.
In the invention, the catalyst comprises cobalt acetate, manganese acetate and potassium bromide, and the three substances are simultaneously used as the catalyst, so that the catalytic oxidation reaction can be smoothly carried out.
In the present invention, the solvent is glacial acetic acid; the mass ratio of the 1-methyl-4-naphthylethanone, the cobalt acetate, the manganese acetate, the potassium bromide, the glacial acetic acid and the oxygen is preferably 100 (3-5): 1400-1600): 80-100, and more preferably 100:4:4:4:1500: 90.
In the invention, the introduction rate of the oxygen is preferably 3-5 cubic meters per hour, and more preferably 4 cubic meters per hour; the temperature of the oxidation reaction is preferably 90-100 ℃, and more preferably 100 ℃; the invention preferably monitors the reaction degree, and the oxygen can be stopped to be introduced when the reaction is carried out until the content of the 1-methyl-4-acetonaphthone is less than 0.5 percent; in a specific embodiment of the present invention, the time of the oxidation reaction is preferably 16 h.
In the specific embodiment of the invention, the oxidation reaction is preferably carried out in a glass lining reaction kettle with a condenser, an oxygen inlet pipe and a tail gas absorption device, the invention preferably adds 1-methyl-4-acetonaphthone, a solvent and a catalyst into the reaction kettle, then starts stirring and heats up to the oxidation reaction temperature, and then oxygen is introduced at a constant speed for reaction.
In the present invention, the reaction formula of the oxidation reaction is shown as formula I:
after the oxidation reaction is finished, the invention preferably carries out post-treatment on the obtained product feed liquid, and the post-treatment preferably comprises the following steps:
(1) cooling the product liquid, and performing solid-liquid separation to obtain a crude product;
(2) and sequentially carrying out alkalization salt formation, decoloration, acidification, solid-liquid separation, water washing, solid-liquid separation again and drying on the crude product to obtain the 1, 4-naphthalenedicarboxylic acid.
In the invention, the solid-liquid separation method is preferably spin-drying, namely a spin-drying mode well known to a person skilled in the art is used, and the subsequent description is not provided.
In the invention, the alkalization salt formation is specifically that the obtained crude product is added into water, then the temperature is raised to 80 ℃, and then liquid caustic soda is added to adjust the pH value of the feed liquid to 7; the mass fraction of the liquid caustic soda is preferably 30%; the ratio of the amount of crude product to water is preferably 150 kg: 2000L. The invention converts 1, 4-naphthalene dicarboxylic acid into sodium salt by alkalization into salt, so as to facilitate subsequent decolorization.
In the invention, the decolorizing agent for decolorization is preferably activated carbon, and specifically, activated carbon is added into alkalized liquid obtained by alkalization, and then decolorization is carried out under stirring conditions; the time for decoloring is preferably 30 min; the mass ratio of the activated carbon to the crude product is preferably 1: 50.
After the decolorization is finished, the decolorized solution is preferably filtered to remove the activated carbon in the decolorized solution, and the filtrate is subjected to acid precipitation. In the invention, the acid precipitation is specifically as follows: and (3) dripping 10 wt% of sulfuric acid into the filtrate at the temperature of 75-85 ℃ until the pH value of the feed liquid is 2, so as to separate out the 1, 4-naphthalenedicarboxylic acid.
After acid precipitation, the invention carries out solid-liquid separation, water washing, solid-liquid separation again and drying on the acid precipitation feed liquid in sequence to obtain the 1, 4-naphthalenedicarboxylic acid.
In the invention, in the process of carrying out solid-liquid separation on the product feed liquid, the main components in the generated mother liquid are acetic acid and a catalyst, and the mother liquid is preferably recycled; the recycling method is preferably as follows: adding acetic anhydride, cobalt acetate, manganese acetate and potassium bromide into the mother solution, and then adding 1-methyl-4-acetonaphthone to perform the next batch of reaction; in a specific embodiment of the present invention, the addition of acetic anhydride is preferably calculated by measuring the moisture of the mother liquor, and the addition of cobalt acetate, manganese acetate and potassium bromide is independently preferably 0.5% of the initial amount.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention.
Example 1
Putting 100kg of 1-methyl-4-naphthylethanone, 4kg of cobalt acetate, 4kg of manganese acetate, 4kg of potassium bromide and 1500kg of glacial acetic acid into a 2000L glass lining reaction kettle with a condenser, an oxygen inlet pipe and a tail gas absorption device, starting stirring, heating to 100 ℃, introducing 90kg of oxygen at a constant speed, stopping introducing the oxygen when the content of the 1-methyl-4-naphthylethanone is controlled to be less than 0.5% in sampling, cooling to 30 ℃, and spin-drying to obtain a crude product with the wet weight of 150kg to be refined; and (3) pumping the mother liquor into the reaction kettle again, measuring the water content, adding acetic anhydride according to the water content of the mother liquor, adding glacial acetic acid to 1500L if the mother liquor is not enough, adding 0.2kg of cobalt acetate, 0.2kg of manganese acetate, 0.2kg of potassium bromide and 100kg of 1-methyl-4-naphthylethanone, and then carrying out the same batch reaction operation.
Adding 150kg of the crude product and 2000L of water into a 3000L glass lining reaction kettle, heating to 80 ℃, dropwise adding 30% liquid caustic soda to adjust the pH value to 7, adding 3kg of active carbon, stirring and decoloring for 30 minutes, filtering, adding into another 3000L glass lining reaction kettle, heating to 80 ℃, dropwise adding 10% dilute sulfuric acid to adjust the pH value to 2 at 75-85 ℃, then sequentially performing spin-drying, water washing and spin-drying again, and drying to obtain 110kg of 1, 4-naphthalenedicarboxylic acid finished product, wherein the purity of the product is 99.8% according to HPLC detection, and the yield is 93.7% in terms of 1-methyl-4-naphthylethanone.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. A method for preparing 1, 4-naphthalenedicarboxylic acid, comprising the steps of:
mixing 1-methyl-4-acetonaphthone, a solvent and a catalyst, and introducing oxygen into the obtained mixed solution to perform oxidation reaction on the 1-methyl-4-acetonaphthone to obtain 1, 4-naphthalenedicarboxylic acid; the catalyst comprises cobalt acetate, manganese acetate and potassium bromide; the solvent is glacial acetic acid.
2. The preparation method according to claim 1, wherein the mass ratio of the 1-methyl-4-acetonaphthone, the cobalt acetate, the manganese acetate, the potassium bromide, the glacial acetic acid and the oxygen is 100 (3-5): 1400-1600): 80-100.
3. The preparation method according to claim 1 or 2, wherein the mass ratio of the 1-methyl-4-acetonaphthone, the cobalt acetate, the manganese acetate, the potassium bromide, the glacial acetic acid and the oxygen is 100:4:4:4:1500: 90.
4. The method according to claim 1, wherein the oxygen is introduced at a rate of 3 to 5 cubic meters per hour.
5. The method according to claim 1 or 4, wherein the temperature of the oxidation reaction is 90 to 100 ℃.
6. The preparation method according to claim 1, further comprising post-treating the resultant product liquid after the oxidation reaction is completed, wherein the post-treatment comprises the steps of:
(1) cooling the product liquid, and performing solid-liquid separation to obtain a crude product;
(2) and sequentially carrying out alkalization salt formation, decoloration, acidification, solid-liquid separation, water washing, solid-liquid separation again and drying on the crude product to obtain the 1, 4-naphthalenedicarboxylic acid.
7. The method according to claim 6, wherein the decoloring agent is activated carbon.
8. The production method according to claim 6, wherein the mother liquor produced by the solid-liquid separation in the step (1) is reused; the recycling method comprises the following steps: and adding acetic anhydride, cobalt acetate, manganese acetate and potassium bromide into the mother liquor, and then adding 1-methyl-4-acetonaphthone to carry out the next batch of reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202010704455.7A CN111747840A (en) | 2020-07-21 | 2020-07-21 | Preparation method of 1, 4-naphthalenedicarboxylic acid |
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| CN202010704455.7A CN111747840A (en) | 2020-07-21 | 2020-07-21 | Preparation method of 1, 4-naphthalenedicarboxylic acid |
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Cited By (3)
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| CN112479861A (en) * | 2020-12-10 | 2021-03-12 | 成家钢 | Liquid-phase normal-pressure catalytic oxygen oxidation safety method and oxygen oxidation safety reaction equipment |
| CN113461511A (en) * | 2021-06-07 | 2021-10-01 | 黄石市利福达医药化工有限公司 | Preparation method of 1, 4-naphthalenedicarboxylic acid |
| CN114014750A (en) * | 2021-11-29 | 2022-02-08 | 黄石市利福达医药化工有限公司 | Method for separating and purifying 1, 4-naphthalenedicarboxylic acid from distillation residue of 1, 4-naphthalenedicarboxylic acid reaction mother liquor |
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| CN114014750A (en) * | 2021-11-29 | 2022-02-08 | 黄石市利福达医药化工有限公司 | Method for separating and purifying 1, 4-naphthalenedicarboxylic acid from distillation residue of 1, 4-naphthalenedicarboxylic acid reaction mother liquor |
| CN114014750B (en) * | 2021-11-29 | 2024-02-13 | 黄石市利福达医药化工有限公司 | Method for separating and purifying 1, 4-naphthalene dicarboxylic acid from distillation residues of 1, 4-naphthalene dicarboxylic acid reaction mother liquor |
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