CN117088769A - Production process of p-tert-butylbenzoic acid product with low toluene residue - Google Patents
Production process of p-tert-butylbenzoic acid product with low toluene residue Download PDFInfo
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- CN117088769A CN117088769A CN202310443124.6A CN202310443124A CN117088769A CN 117088769 A CN117088769 A CN 117088769A CN 202310443124 A CN202310443124 A CN 202310443124A CN 117088769 A CN117088769 A CN 117088769A
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- butylbenzoic acid
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- butyltoluene
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- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 125000003944 tolyl group Chemical group 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 239000000047 product Substances 0.000 claims abstract description 64
- QCWXDVFBZVHKLV-UHFFFAOYSA-N 1-tert-butyl-4-methylbenzene Chemical compound CC1=CC=C(C(C)(C)C)C=C1 QCWXDVFBZVHKLV-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 239000012065 filter cake Substances 0.000 claims abstract description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 34
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 31
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000008213 purified water Substances 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 238000001914 filtration Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 16
- 239000012043 crude product Substances 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 18
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 polypropylene Polymers 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
-
- 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
- C07C51/305—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with sulfur or sulfur-containing compounds
-
- 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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- 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
Abstract
The application relates to the field of chemical synthesis, in particular to a production process of a p-tert-butylbenzoic acid product with low toluene residue, which comprises the following steps: (1) Obtaining a crude product of the p-tert-butyltoluene, and obtaining a refined product of the p-tert-butyltoluene after rectification; (2) The refined p-tert-butyltoluene reacts with a catalyst, and oxygen is introduced for oxidation to obtain a crude p-tert-butylbenzoic acid product; (3) Adding crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding butyl acetate, activated carbon and purified water; heating to dissolve the crude tert-butylbenzoic acid completely, stirring continuously, cooling, crystallizing, and filtering to obtain a first filter cake; (4) Adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing with water at normal temperature, and then filtering to obtain a second filter cake; and drying the second filter cake to obtain refined p-tert-butylbenzoic acid. The application solves the problem of high toluene residue in the product, reduces the production procedures and reduces the production cost.
Description
Technical Field
The application relates to the field of chemical synthesis, in particular to a production process of a p-tert-butylbenzoic acid product with low toluene residue.
Background
P-tert-butylbenzoic acid (PTBBA) is colorless needle-like crystal or crystal powder, is an important organic synthesis intermediate, and can be widely applied to polypropylene nucleating agents, polyvinyl chloride heat stabilizers, additives for metal processing cutting and lubricating oil, antioxidants, alkyd resin modifiers, soldering flux, fuel, pesticides, essence and perfume and daily chemical industry.
In the production process of p-tert-butylbenzoic acid, toluene is required to be introduced into the crude p-tert-butylbenzoic acid for flushing, such as a refining method of CN202110399870.0 p-tert-butylbenzoic acid, wherein the crude p-tert-butylbenzoic acid is required to be subjected to cooling crystallization and centrifugal drying, and the crude p-tert-butyltoluene is used for flushing to obtain a centrifugal crude product; and adding toluene into the centrifugal crude product, heating to dissolve, transferring to a recrystallization kettle for cooling and crystallizing, and drying to obtain a p-tert-butyl benzoic acid finished product. Reintroducing toluene in the above process results in toluene remaining in the product; the existing technology can only achieve the purpose of reducing toluene residues through recrystallization and repeated drying, but the reprocessing can greatly improve the production cost of products, increase the production time of each batch of products and cause product loss; therefore, the traditional process needs to be improved, and a production process of the p-tert-butylbenzoic acid product with low toluene residue is designed.
Disclosure of Invention
The application aims to provide a production process of a p-tert-butylbenzoic acid product with low toluene residue, which solves the problems in the prior art.
In order to achieve the above purpose, the present application provides the following technical solutions:
a production process of a p-tert-butylbenzoic acid product with low toluene residue comprises the following steps:
(1) Step one: toluene, isobutene and concentrated sulfuric acid are added into a reaction kettle according to the mass fraction ratio of 18-20:7-8:4-5, the reaction is carried out for 10-15 hours, a crude p-tert-butyltoluene product is obtained, and the crude p-tert-butyltoluene product is rectified to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product;
(3) Step three: adding crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding butyl acetate, activated carbon and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing for 20-30 minutes at normal temperature, and then filtering to obtain a second filter cake; and drying the second filter cake to obtain refined p-tert-butylbenzoic acid.
What needs to be further explained is: in the first step, toluene, isobutene and concentrated sulfuric acid are mixed according to a mass fraction ratio of 18:7:5.
What needs to be further explained is: the catalyst in the second step is a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1.
Further described are: in the second step, the mass ratio of the refined p-tert-butyltoluene to the catalyst is 100:0.5-1.
Further described are: in the second step, the mass ratio of the refined p-tert-butyltoluene to the catalyst is 100:0.8.
What needs to be further explained is: in the third step, the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:200-220:0.8-1:20-50.
Further described are: in the third step, the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:220:0.8:30.
What needs to be further explained is: the mass of the butyl acetate added in the fourth step is 0.8-1% of the mass of the butyl acetate added in the third step.
What needs to be further explained is: in the second step, the temperature in the reaction kettle is 80-85 ℃ and the pressure is 0.3-0.5 megapascals.
Further described are: in the second step, the temperature in the reaction kettle is 80 ℃ and the pressure is 0.3 megapascals.
Compared with the prior art, the application has the beneficial effects that: according to the application, toluene is not introduced again as a solvent for use in purification treatment, so that the problem of high toluene residue in a product is solved, and the steps of recrystallization and repeated drying are reduced, the production procedures are reduced, and the production cost is reduced because no toluene is introduced again; compared with toluene, the butyl acetate has less harm to human body and is more beneficial to environmental protection production.
Detailed Description
Example 1
In embodiment 1 of the present application, the method comprises the following steps:
(1) Step one: 180kg of toluene, 70kg of isobutene and 4kg of concentrated sulfuric acid are sequentially added into a reaction kettle to react for 10-15 hours to obtain a crude p-tert-butyltoluene product, and the crude p-tert-butyltoluene product is rectified to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product; wherein the catalyst accounts for 0.5% of the mass of the refined p-tert-butyltoluene; the catalyst adopts a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1;
(3) Step three: adding 100kg of crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding butyl acetate, activated carbon and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of the tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake, wherein the mass of the first filter cake is 95% of that of the crude product of the p-tert-butylbenzoic acid; wherein the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:200:0.8:20;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing for 20-30 minutes at normal temperature, and then filtering to obtain a second filter cake; drying the second filter cake to obtain refined p-tert-butylbenzoic acid; the mass of butyl acetate in this step was 0.8% of the mass of butyl triacetate in the step.
In the second step, the temperature in the reaction kettle is 80 ℃ and the pressure is 0.3 megapascals.
The p-tert-butylbenzoic acid prepared in this example had a purity of 99.5% by HPLC and a toluene content of 0.
Example 2
In embodiment 2 of the present application, the method comprises the following steps:
(1) Step one: sequentially adding 200kg of toluene, 70kg of isobutene and 4kg of concentrated sulfuric acid into a reaction kettle, reacting for 10-15 hours to obtain a crude p-tert-butyltoluene product, and rectifying the crude p-tert-butyltoluene product to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product; wherein the catalyst accounts for 1% of the mass of the refined p-tert-butyltoluene; the catalyst adopts a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1;
(3) Step three: adding 100kg of crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding butyl acetate, activated carbon and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of the tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake, wherein the mass of the first filter cake is 95% of that of the crude product of the p-tert-butylbenzoic acid; wherein the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:200:1:50;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing for 20-30 minutes at normal temperature, and then filtering to obtain a second filter cake; drying the second filter cake to obtain refined p-tert-butylbenzoic acid; the mass of butyl acetate in this step was 1% of the mass of butyl triacetate in the step.
In the second step, the temperature in the reaction kettle is 85 ℃ and the pressure is 0.5 megapascals.
The p-tert-butylbenzoic acid prepared in this example had a purity of 99.3% by HPLC and a toluene content of 0.
Example 3
In embodiment 3 of the present application, the method comprises the following steps:
(1) Step one: 180kg of toluene, 70kg of isobutene and 5kg of concentrated sulfuric acid are sequentially added into a reaction kettle to react for 10-15 hours to obtain a crude p-tert-butyltoluene product, and the crude p-tert-butyltoluene product is rectified to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product; wherein the catalyst accounts for 0.8% of the mass of the refined p-tert-butyltoluene; the catalyst adopts a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1;
(3) Step three: adding 100kg of crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding butyl acetate, activated carbon and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of the tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake, wherein the mass of the first filter cake is 95% of that of the crude product of the p-tert-butylbenzoic acid; wherein the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:220:0.8:30;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing for 20-30 minutes at normal temperature, and then filtering to obtain a second filter cake; drying the second filter cake to obtain refined p-tert-butylbenzoic acid; the mass of butyl acetate in this step was 1% of the mass of butyl triacetate in the step.
In the second step, the temperature in the reaction kettle is 80 ℃ and the pressure is 0.3 megapascals.
The p-tert-butylbenzoic acid prepared in this example had a purity of 99.7% by HPLC and a toluene content of 0.
Comparative example 1
Comparative example 1 of the present application comprises the steps of:
(1) Step one: 180kg of toluene, 70kg of isobutene and 5kg of concentrated sulfuric acid are sequentially added into a reaction kettle to react for 10-15 hours to obtain a crude p-tert-butyltoluene product, and the crude p-tert-butyltoluene product is rectified to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product; wherein the catalyst accounts for 0.8% of the mass of the refined p-tert-butyltoluene; the catalyst adopts a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1;
(3) Step three: adding 100kg of crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding ethyl acetate, activated carbon and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of the tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake, wherein the mass of the first filter cake is 92% of that of the crude product of the p-tert-butylbenzoic acid; wherein the mass ratio of the crude p-tert-butylbenzoic acid to the ethyl acetate to the activated carbon to the purified water is 100:220:0.8:30;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, adding ethyl acetate, washing for 20-30 minutes at normal temperature, and filtering to obtain a second filter cake; drying the second filter cake to obtain refined p-tert-butylbenzoic acid; the mass of ethyl acetate in this step was 1% of the mass of ethyl triacetate in the step.
In the second step, the temperature in the reaction kettle is 80 ℃ and the pressure is 0.3 megapascals.
The p-tert-butylbenzoic acid prepared in this example had a purity of 97.3% by HPLC and a toluene content of 0, and it was found that ethyl acetate was used instead of butyl acetate, compared with example 3, and toluene was not re-introduced so that no toluene residue was detected, but the purification purity was insufficient.
Comparative example 2
Comparative example 1 of the present application comprises the steps of:
(1) Step one: 180kg of toluene, 70kg of isobutene and 5kg of concentrated sulfuric acid are sequentially added into a reaction kettle to react for 10-15 hours to obtain a crude p-tert-butyltoluene product, and the crude p-tert-butyltoluene product is rectified to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product; wherein the catalyst accounts for 0.8% of the mass of the refined p-tert-butyltoluene; the catalyst adopts a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1;
(3) Step three: adding 100kg of crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding ethyl acetate and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of the tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake, wherein the mass of the first filter cake is 92% of that of the crude product of the p-tert-butylbenzoic acid; wherein the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:220:30;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing for 20-30 minutes at normal temperature, and then filtering to obtain a second filter cake; drying the second filter cake to obtain refined p-tert-butylbenzoic acid; the mass of butyl acetate in this step was 1% of the mass of butyl triacetate in the step.
In the second step, the temperature in the reaction kettle is 80 ℃ and the pressure is 0.3 megapascals.
The purity of the p-tert-butylbenzoic acid fine product prepared in this example was 98.3% by HPLC, and the toluene content was 0.1%, and compared with example 3, it was found that no activated carbon was added, toluene remained in the test, and the purity was inferior to that of the p-tert-butylbenzoic acid fine product in example 3.
It will be evident to those skilled in the art that the application is not limited to the details of the foregoing illustrative embodiments, and that the present application may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive, the scope of the application being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (10)
1. The production process of the p-tert-butylbenzoic acid product with low toluene residue is characterized by comprising the following steps: (1) step one: toluene, isobutene and concentrated sulfuric acid are added into a reaction kettle according to the mass fraction ratio of 18-20:7-8:4-5, the reaction is carried out for 10-15 hours, a crude p-tert-butyltoluene product is obtained, and the crude p-tert-butyltoluene product is rectified to obtain a refined p-tert-butyltoluene product;
(2) Step two: adding the refined p-tert-butyltoluene obtained in the step one and a catalyst into a reaction kettle, introducing oxygen to react, and centrifuging the reacted product to obtain a crude p-tert-butylbenzoic acid product;
(3) Step three: adding crude p-tert-butylbenzoic acid into a reaction kettle, and sequentially adding butyl acetate, activated carbon and purified water; then heating to 50-60 ℃ to completely dissolve the crude product of tert-butylbenzoic acid, continuously stirring for 20-30 minutes, cooling, crystallizing and filtering to obtain a first filter cake;
(4) Step four: adding the first filter cake into a reaction kettle, adding purified water, stirring, then adding butyl acetate, washing for 20-30 minutes at normal temperature, and then filtering to obtain a second filter cake; and drying the second filter cake to obtain refined p-tert-butylbenzoic acid.
2. The process for producing a p-tert-butylbenzoic acid product having a low toluene residue according to claim 1, wherein: in the first step, toluene, isobutene and concentrated sulfuric acid are mixed according to a mass fraction ratio of 18:7:5.
3. The process for producing a p-tert-butylbenzoic acid product having a low toluene residue according to claim 1, wherein: the catalyst in the second step is a mixture of cobalt acetate and manganese acetate; the mass ratio of the cobalt acetate to the manganese acetate is 1:1.
4. The process for producing p-tert-butylbenzoic acid product with low toluene residue as in claim 3, wherein the mass ratio of p-tert-butyltoluene fine product to catalyst in step two is 100:0.5-1.
5. The process for producing p-tert-butylbenzoic acid product having low toluene residue according to claim 4, wherein the mass ratio of p-tert-butyltoluene fine product to catalyst in step two is 100:0.8.
6. The process for producing a p-tert-butylbenzoic acid product having a low toluene residue according to claim 1, wherein: in the third step, the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:200-220:0.8-1:20-50.
7. The production process of the p-tert-butylbenzoic acid product with low toluene residue as in claim 6, wherein in the third step, the mass ratio of the crude p-tert-butylbenzoic acid to the butyl acetate to the activated carbon to the purified water is 100:220:0.8:30.
8. The process for producing a p-tert-butylbenzoic acid product having a low toluene residue according to claim 1, wherein: the mass of the butyl acetate added in the fourth step is 0.8-1% of the mass of the butyl acetate added in the third step.
9. The process for producing a p-tert-butylbenzoic acid product having a low toluene residue according to claim 1, wherein: in the second step, the temperature in the reaction kettle is 80-85 ℃ and the pressure is 0.3-0.5 megapascals.
10. The process for producing a p-tert-butylbenzoic acid product having a low toluene residue according to claim 9, wherein: in the second step, the temperature in the reaction kettle is 80 ℃ and the pressure is 0.3 megapascals.
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