CN117800880A - Method for synthesizing 4,4' -biphenyl disulfonic acid - Google Patents
Method for synthesizing 4,4' -biphenyl disulfonic acid Download PDFInfo
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- CN117800880A CN117800880A CN202311611809.3A CN202311611809A CN117800880A CN 117800880 A CN117800880 A CN 117800880A CN 202311611809 A CN202311611809 A CN 202311611809A CN 117800880 A CN117800880 A CN 117800880A
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- China
- Prior art keywords
- dichloroethane
- acid
- synthesizing
- biphenyl
- sulfuric acid
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- ABSXMLODUTXQDJ-UHFFFAOYSA-N 4-(4-sulfophenyl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=C(S(O)(=O)=O)C=C1 ABSXMLODUTXQDJ-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 42
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims abstract description 33
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000012071 phase Substances 0.000 claims abstract description 21
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 14
- 239000004305 biphenyl Substances 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 10
- 238000004321 preservation Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 10
- 238000000605 extraction Methods 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
- 238000006277 sulfonation reaction Methods 0.000 description 7
- 239000002184 metal Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000005791 algae growth Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- -1 arylsulfonyl chloride Chemical compound 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 4,4' -benzene disulfonic acid, which belongs to the technical field of fine chemical engineering and comprises the following steps: adding biphenyl into a three-neck flask, heating to 80 ℃, dropwise adding concentrated sulfuric acid, heating to 160 ℃ after the dropwise adding is finished, and continuing to perform heat preservation reaction for 1h at 160 ℃. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. And (3) distilling the dichloroethane phase under reduced pressure, and drying to obtain the pure 4,4' -biphenyl disulfonic acid. The method is simple to operate, simple and convenient to post-treat, effectively reduces the separation difficulty, and improves the purity of the product.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a method for synthesizing 4,4' -biphenyl disulfonic acid.
Background
4,4' -benzenedisulfonic acid is a chemical substance widely used in the industrial and agricultural fields. Biphenyl disulfonic acid is an effective water treatment agent that can be used to prevent scale and algae growth to keep water clean. It can be used in feed water and industrial circulating water systems. The metal rust inhibitor has good metal rust inhibition capability, and can be used for preparing metal rust inhibitors to protect metal surfaces from oxidation and corrosion. Can be used as an additive of dyes and bleaching agents in textile industry, and has excellent dyeing and bleaching performances. Because of its good carbonate solubility and complexing properties, it can be used in the preparation of cleaners and detergents for removing stains, deposits and scale. Is a good chemical product.
The literature reports that the synthesis method of 4,4' -benzene disulfonic acid mainly comprises the following two methods: (1) Sulfur trioxide sulfonation method: the liquid phase or gas phase sulfur trioxide gas is used for sulfonation reaction, the process flow of the sulfur trioxide sulfonation is shorter, the product purity is high, and the liquid sulfur trioxide sulfonation is suitable for the sulfonation of liquid aromatic hydrocarbon which is more stable and is not easy to react. (2) chlorosulfonic acid sulfonation method: the arylsulfonic acid and arylsulfonyl chloride are prepared from excess chlorosulfonic acid. (3) Sulfonation is carried out using excess sulfuric acid or fuming sulfuric acid.
Disclosure of Invention
This section is intended to outline some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section as well as in the description of the invention and in the title of the invention, which may not be used to limit the scope of the invention.
Therefore, the invention aims to provide a method for synthesizing 4,4' -biphenyl disulfonic acid, which is simple to operate, simple and convenient in post-treatment separation, effectively reduces the separation difficulty and improves the purity of the product.
In order to solve the technical problems, the invention provides a method for synthesizing 4,4' -biphenyl disulfonic acid, which adopts the following technical scheme: the method comprises the following specific steps:
s1: adding biphenyl into a three-neck flask, heating to 70-100 ℃, dropwise adding concentrated sulfuric acid, heating to 160 ℃ after the dropwise adding, and continuously preserving heat for reaction for 0.5-3 h at 85-160 ℃;
s2: after the reaction is finished, cooling to below 80 ℃, adding dichloroethane into the system, extracting and separating liquid, separating out the lower inorganic phase sulfuric acid, and separating out the upper dichloroethane organic phase for later use;
s3: and (3) distilling the dichloroethane phase under reduced pressure, and drying to obtain the pure 4,4' -biphenyl disulfonic acid.
Optionally, the molar ratio of biphenyl to concentrated sulfuric acid in the step S1 is 1:2 to 5.
Optionally, the sulfuric acid dropping temperature in the step S1 is 80 ℃.
Optionally, the duration of dropwise adding sulfuric acid in the step S1 is kept between 0.5 and 3 hours.
Optionally, the heat preservation duration in the step S1 is 1h.
Optionally, the amount of dichloroethane in step S2 is 2 to 5 times the amount of biphenyl.
In summary, the present invention includes at least one of the following beneficial effects:
1. the solvent dichloroethane introduced by the invention reduces the problem of product caking in the cooling process, and the operation is simpler, more convenient and safer.
2. On the premise of ensuring the yield, the invention improves the purity of the product, avoids complex purification steps, and ensures that the reaction is easier to be amplified.
Detailed Description
The present invention will be described in further detail below.
A method for synthesizing 4,4' -biphenyl disulfonic acid comprises the following specific steps:
s1: adding biphenyl into a three-neck flask, heating to 70-100 ℃, dropwise adding concentrated sulfuric acid, heating to 160 ℃ after the dropwise adding, and continuously preserving heat for reaction for 0.5-3 h at 85-160 ℃;
s2: after the reaction is finished, cooling to below 80 ℃, adding dichloroethane into the system, extracting and separating liquid, separating out the lower inorganic phase sulfuric acid, and separating out the upper dichloroethane organic phase for later use;
s3: and (3) distilling the dichloroethane phase under reduced pressure, and drying to obtain the pure 4,4' -biphenyl disulfonic acid.
Example 1
To a three-necked flask, biphenyl (0.2 mol,30.9 g) was added, the temperature was raised to 80℃and concentrated sulfuric acid (1.01 mol,100.01 g) was added dropwise over 1 hour, the temperature was raised to 160℃after the completion of the addition, and the reaction was continued at 160℃for 1 hour with heat preservation. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. The dichloroethane phase is distilled under reduced pressure and dried to obtain pure 4,4' -biphenyl disulfonic acid with the yield of 94 percent and the purity of 99.5 percent.
Example 2
To a three-necked flask, biphenyl (0.2 mol,30.9 g) was added, the temperature was raised to 90℃and concentrated sulfuric acid (1.01 mol,100.01 g) was added dropwise over 1 hour, the temperature was raised to 160℃after the completion of the addition, and the reaction was continued at 160℃for 1 hour with heat preservation. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. The dichloroethane phase is distilled under reduced pressure and dried to obtain pure 4,4' -biphenyl disulfonic acid with the yield of 94.5 percent and the purity of 99.4 percent.
Example 3
To a three-necked flask, biphenyl (0.2 mol,30.9 g) was added, the temperature was raised to 90℃and concentrated sulfuric acid (1.01 mol,100.01 g) was added dropwise over 1 hour, the temperature was raised to 160℃after the completion of the addition, and the reaction was continued at 160℃for 2 hours with heat preservation. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. The dichloroethane phase is distilled under reduced pressure and dried to obtain pure 4,4' -biphenyl disulfonic acid with the yield of 96.3 percent and the purity of 99.6 percent.
Example 4
To a three-necked flask, biphenyl (0.2 mol,30.9 g) was added, the temperature was raised to 90℃and concentrated sulfuric acid (1.01 mol,100.01 g) was added dropwise over 2 hours, the temperature was raised to 160℃after the completion of the addition, and the reaction was continued at 160℃for 2 hours with heat preservation. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. The dichloroethane phase is distilled under reduced pressure and dried to obtain pure 4,4' -biphenyl disulfonic acid with the yield of 94.1 percent and the purity of 99.3 percent.
Example 5
To a three-necked flask, biphenyl (0.2 mol,30.9 g) was added, the temperature was raised to 90℃and concentrated sulfuric acid (0.8 mol,78.4 g) was added dropwise over 1 hour, the temperature was raised to 160℃after the completion of the dropwise addition, and the reaction was continued at 160℃for 2 hours with heat preservation. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. The dichloroethane phase is distilled under reduced pressure and dried to obtain pure 4,4' -biphenyl disulfonic acid with the yield of 92.1 percent and the purity of 99.2 percent.
Example 6
To a three-necked flask, biphenyl (0.2 mol,30.9 g) was added, the temperature was raised to 80℃and concentrated sulfuric acid (1.01 mol,100.01 g) was added dropwise over 1 hour, the temperature was raised to 160℃after the completion of the addition, and the reaction was continued at 160℃for 2 hours with heat preservation. After the reaction is finished, the temperature is reduced to below 80 ℃, dichloroethane is added into the system, the lower layer inorganic phase sulfuric acid is separated through extraction and liquid separation, and the upper layer dichloroethane organic phase is separated for standby. The dichloroethane phase is distilled under reduced pressure and dried to obtain pure 4,4' -biphenyl disulfonic acid with the yield of 96.3 percent and the purity of 99.6 percent.
The above embodiments are not intended to limit the scope of the present invention, so: all equivalent changes in structure, shape and principle of the invention should be covered in the scope of protection of the invention.
Claims (7)
1. A method for synthesizing 4,4' -biphenyl disulfonic acid, which is characterized by comprising the following steps: the method comprises the following specific steps:
s1: adding biphenyl into a three-neck flask, heating to 70-100 ℃, dropwise adding concentrated sulfuric acid, heating to 160 ℃ after the dropwise adding, and continuously preserving heat for reaction for 0.5-3 h at 85-160 ℃;
s2: after the reaction is finished, cooling to below 80 ℃, adding dichloroethane into the system, extracting and separating liquid, separating out the lower inorganic phase sulfuric acid, and separating out the upper dichloroethane organic phase for later use;
s3: and (3) distilling the dichloroethane phase under reduced pressure, and drying to obtain the pure 4,4' -biphenyl disulfonic acid.
2. A method for synthesizing 4,4' -biphenyldisulfonic acid as in claim 1, wherein: the molar ratio of biphenyl to concentrated sulfuric acid in the step S1 is 1:2 to 5.
3. A method for synthesizing 4,4' -biphenyldisulfonic acid as in claim 1, wherein: the sulfuric acid dropping temperature in the step S1 is 80 ℃.
4. A method for synthesizing 4,4' -biphenyldisulfonic acid as in claim 1, wherein: and in the step S1, the time length for dropwise adding sulfuric acid is kept between 0.5 and 3 hours.
5. A method for synthesizing 4,4' -biphenyldisulfonic acid as in claim 1, wherein: and in the step S1, the temperature of the thermal insulation reaction is kept at 85-130 ℃.
6. A method for synthesizing 4,4' -biphenyldisulfonic acid as in claim 1, wherein: and in the step S1, the heat preservation time is 1h.
7. A method for synthesizing 4,4' -biphenyldisulfonic acid as in claim 1, wherein: the amount of dichloroethane in the step S2 is 2 to 5 times of the amount of biphenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311611809.3A CN117800880A (en) | 2023-11-29 | 2023-11-29 | Method for synthesizing 4,4' -biphenyl disulfonic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311611809.3A CN117800880A (en) | 2023-11-29 | 2023-11-29 | Method for synthesizing 4,4' -biphenyl disulfonic acid |
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| CN202311611809.3A Pending CN117800880A (en) | 2023-11-29 | 2023-11-29 | Method for synthesizing 4,4' -biphenyl disulfonic acid |
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| Country | Link |
|---|---|
| CN (1) | CN117800880A (en) |
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- 2023-11-29 CN CN202311611809.3A patent/CN117800880A/en active Pending
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