CN116574003A - Method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution - Google Patents
Method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution Download PDFInfo
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- CN116574003A CN116574003A CN202310487089.8A CN202310487089A CN116574003A CN 116574003 A CN116574003 A CN 116574003A CN 202310487089 A CN202310487089 A CN 202310487089A CN 116574003 A CN116574003 A CN 116574003A
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- Prior art keywords
- acrylic acid
- aqueous solution
- crude
- purity
- extractant
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 102
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940011051 isopropyl acetate Drugs 0.000 claims abstract description 10
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001555 benzenes Chemical class 0.000 claims abstract description 5
- 239000008096 xylene Substances 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 10
- 238000011084 recovery Methods 0.000 abstract description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 description 31
- 239000012071 phase Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- 238000001514 detection method Methods 0.000 description 6
- 238000007599 discharging Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing high-purity acrylic acid from a crude acrylic acid aqueous solution, and belongs to the technical field of acrylic acid purification. The invention utilizes the extractant composed of isopropyl acetate, benzene and benzene derivatives (toluene or xylene) to extract the crude acrylic acid aqueous solution, thereby leading the extract to be rich in acrylic acid, reducing the types and the content of impurities in the extract phase and obviously improving the recovery rate and the purity of the acrylic acid.
Description
Technical Field
The invention belongs to the technical field of acrylic acid purification, and particularly relates to a method for preparing high-purity acrylic acid from a crude acrylic acid aqueous solution.
Background
Acrylic acid is an important chemical raw material, and can be used as a monomer of a polymer to synthesize thousands of polymers. At present, propylene is industrially oxidized in a gas phase under the action of a catalyst, water is used for obtaining an acrylic acid aqueous solution after cooling, and finally the acrylic acid aqueous solution is purified to obtain an acrylic acid product. Wherein the mass concentration of acrylic acid in the acrylic acid aqueous solution is 25-50%, and formaldehyde, acrolein, propionic acid, acetone, maleic acid, acrylic acid dimer and the like are also contained,
the current industrial purification method of the crude acrylic acid aqueous solution is an azeotropic method and an extraction method, specifically, toluene and water and acetic acid in the crude acrylic acid aqueous solution are azeotroped to separate the water and the acetic acid of the acrylic acid aqueous solution. This technique has high energy consumption and still cannot obtain high purity acrylic acid.
The current extraction method for extracting the crude acrylic acid aqueous solution has the following problems:
1. the extraction temperature is high, the extraction is incomplete at room temperature, and the great economic loss is caused;
2. various impurities still exist in the extract liquid obtained after extraction, and a rectifying tower cannot be adopted to obtain high-purity acrylic acid.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for preparing high-purity acrylic acid from a crude acrylic acid aqueous solution. The purification process has low energy consumption, and the purity of the obtained acrylic acid product is up to more than 98%.
The invention is realized by adopting the following technical scheme:
the method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution comprises extracting crude acrylic acid aqueous solution at room temperature with extractant, standing for layering, and collecting organic phase to obtain extract rich in acrylic acid; finally, introducing the extract into a rectifying tower for rectification, and obtaining high-purity acrylic acid at the bottom of the rectifying tower;
the extractant is prepared by mixing isopropyl acetate and benzene derivatives according to a volume ratio of 1-6:1-2:0-2, wherein the benzene derivatives are toluene or xylene.
Preferably, the volume ratio of the extractant to the crude acrylic acid aqueous solution is 0.7-2:1.
Preferably, the room temperature is 10-20 ℃.
Preferably, the extract contains acrylic acid, an extractant and acetic acid.
Preferably, the purity of the acrylic acid collected after the rectification treatment is greater than 98%.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides an extractant for purifying an acrylic acid aqueous solution, which consists of isopropyl acetate, dimethylbenzene and methylbenzene, can extract acrylic acid from the aqueous solution, reduces the types and the content of impurities in an extraction phase, and remarkably improves the recovery rate of the acrylic acid.
The invention has low energy consumption, is convenient for industrialized implementation and has higher economic value.
Drawings
FIG. 1 is a schematic diagram of the structure of the extraction column of the present invention.
Detailed Description
The following detailed description of the present invention provides for a more complete understanding of the objects, features and advantages of the present invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Example 1
A method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution comprises the following specific steps:
the upper end and the lower end of an extraction tower are respectively filled with a crude acrylic acid aqueous solution (the mass concentration of the detected acrylic acid is 38.9%) and an extractant, wherein the extractant is formed by mixing isopropyl acetate, benzene and toluene according to the volume ratio of 1.5:1:1;
and simultaneously controlling the volume ratio of the extractant to the crude acrylic acid aqueous solution in the extraction tower to be 1.8:1.
Extracting at room temperature for no more than 50min;
standing for layering, and collecting an upper oil phase, namely an extraction phase, to obtain an extraction liquid rich in acrylic acid; the lower water phase is the raffinate phase.
And (3) introducing the extract into a rectifying tower for rectification, discharging acrylic acid from the bottom of the rectifying tower, and collecting the acrylic acid, wherein the detection purity is 98.5%, and the acrylic acid recovery rate is 91%.
Example 2
A method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution comprises the following specific steps:
the upper end and the lower end of an extraction tower are respectively filled with a crude acrylic acid aqueous solution (the mass concentration of the detected acrylic acid is 38.9%) and an extractant, wherein the extractant is formed by mixing isopropyl acetate, benzene and dimethylbenzene according to the volume ratio of 1:1:2;
and simultaneously controlling the volume ratio of the extractant to the crude acrylic acid aqueous solution in the extraction tower to be 0.8:1.
Extracting at room temperature for no more than 60min;
standing for layering, and collecting an upper oil phase, namely an extraction phase, to obtain an extraction liquid rich in acrylic acid; the lower water phase is the raffinate phase.
And (3) introducing the extract into a rectifying tower for rectification, discharging acrylic acid from the bottom of the rectifying tower, and collecting the acrylic acid, wherein the detection purity is 98.8%, and the acrylic acid recovery rate is 95%.
Example 3
A method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution comprises the following specific steps:
the upper end and the lower end of an extraction tower are respectively filled with a crude acrylic acid aqueous solution (the mass concentration of the detected acrylic acid is 38.9%) and an extractant, wherein the extractant is formed by mixing isopropyl acetate, benzene and dimethylbenzene according to the volume ratio of 2:2:1;
and simultaneously controlling the volume ratio of the extractant to the crude acrylic acid aqueous solution in the extraction tower to be 1.1:1.
Extracting at room temperature for no more than 60min;
standing for layering, and collecting an upper oil phase, namely an extraction phase, to obtain an extraction liquid rich in acrylic acid; the lower water phase is the raffinate phase.
And (3) introducing the extract into a rectifying tower for rectification, discharging acrylic acid from the bottom of the rectifying tower, and collecting the acrylic acid, wherein the detection purity is 99.0%, and the acrylic acid recovery rate is 96%.
Example 4
A method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution comprises the following specific steps:
the upper end and the lower end of an extraction tower are respectively filled with a crude acrylic acid aqueous solution (the mass concentration of the detected acrylic acid is 38.9%) and an extractant, wherein the extractant is formed by mixing isopropyl acetate, benzene and toluene according to the volume ratio of 2.7:2:1;
and simultaneously controlling the volume ratio of the extractant to the crude acrylic acid aqueous solution in the extraction tower to be 1.8:1.
Extracting at room temperature for no more than 50min;
standing for layering, and collecting an upper oil phase, namely an extraction phase, to obtain an extraction liquid rich in acrylic acid; the lower water phase is the raffinate phase.
And (3) introducing the extract into a rectifying tower for rectification, discharging acrylic acid from the bottom of the rectifying tower, and collecting the acrylic acid, wherein the detection purity is 99.2%, and the recovery rate of the acrylic acid is 98%.
Comparative example 1
A method for purifying crude acrylic acid aqueous solution comprises the following specific steps:
the upper end and the lower end of an extraction tower are respectively filled with a crude acrylic acid aqueous solution (the mass concentration of the detected acrylic acid is 38.9%) and an extractant, wherein the extractant is formed by mixing isopropyl acetate and dimethylbenzene according to the volume ratio of 9:1;
and simultaneously controlling the volume ratio of the extractant to the crude acrylic acid aqueous solution in the extraction tower to be 30:1.
Extracting at room temperature for 50min;
standing for layering, and collecting an upper oil phase, namely an extraction phase, to obtain an extraction liquid containing acrylic acid; the lower water phase is the raffinate phase.
And (3) introducing the extract into a rectifying tower for rectification, discharging the acrylic acid from the bottom of the rectifying tower, and collecting the acrylic acid, wherein the detection purity is 83.2%, and the acrylic acid recovery rate is 72.9%.
Comparative example 2
A method for purifying crude acrylic acid aqueous solution comprises the following specific steps:
the upper end and the lower end of an extraction tower are respectively filled with a crude acrylic acid aqueous solution (the mass concentration of the acrylic acid is detected to be 38.9%) and an extractant, wherein the extractant is isopropyl acetate;
and simultaneously controlling the volume ratio of the extractant to the crude acrylic acid aqueous solution in the extraction tower to be 30:1.
Extracting at room temperature for 50min;
standing for layering, and collecting an upper oil phase, namely an extraction phase, to obtain an extraction liquid containing acrylic acid; the lower water phase is the raffinate phase.
And (3) introducing the extract into a rectifying tower for rectification, discharging the acrylic acid from the bottom of the rectifying tower, and collecting the acrylic acid, wherein the detection purity is 73.4%, and the acrylic acid recovery rate is 61.5%.
The foregoing examples illustrate only a few embodiments of the invention and are described in detail herein without thereby limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (5)
1. The method for purifying the crude acrylic acid aqueous solution is characterized in that the crude acrylic acid aqueous solution is extracted at room temperature by using an extracting agent, and an organic phase is collected after standing and layering, so as to obtain an extract rich in acrylic acid; finally, introducing the extract into a rectifying tower for rectification, and obtaining high-purity acrylic acid at the bottom of the rectifying tower;
the extractant is prepared by mixing isopropyl acetate and benzene derivatives according to a volume ratio of 1-6:1-2:0-2, wherein the benzene derivatives are toluene or xylene.
2. The method for purifying an aqueous solution of crude acrylic acid according to claim 1, wherein the volume ratio of the extractant to the aqueous solution of crude acrylic acid is 0.7 to 2:1.
3. The method for purifying an aqueous solution of crude acrylic acid according to claim 1, wherein the room temperature is 10 to 20 ℃.
4. The method for purifying an aqueous solution of crude acrylic acid as claimed in claim 1, wherein the extract contains acrylic acid, an extractant and acetic acid.
5. The method for purifying an aqueous solution of crude acrylic acid as claimed in claim 1, wherein the purity of the acrylic acid collected after the rectification treatment is more than 98%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310487089.8A CN116574003A (en) | 2023-05-04 | 2023-05-04 | Method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310487089.8A CN116574003A (en) | 2023-05-04 | 2023-05-04 | Method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116574003A true CN116574003A (en) | 2023-08-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310487089.8A Pending CN116574003A (en) | 2023-05-04 | 2023-05-04 | Method for preparing high-purity acrylic acid from crude acrylic acid aqueous solution |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116574003A (en) |
-
2023
- 2023-05-04 CN CN202310487089.8A patent/CN116574003A/en active Pending
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