CN115947674B - Production process of isophthalic acid-5-sodium sulfonate - Google Patents
Production process of isophthalic acid-5-sodium sulfonate Download PDFInfo
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- CN115947674B CN115947674B CN202211637981.1A CN202211637981A CN115947674B CN 115947674 B CN115947674 B CN 115947674B CN 202211637981 A CN202211637981 A CN 202211637981A CN 115947674 B CN115947674 B CN 115947674B
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 68
- 239000011734 sodium Substances 0.000 title claims abstract description 52
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title abstract description 32
- 238000002425 crystallisation Methods 0.000 claims abstract description 81
- 230000008025 crystallization Effects 0.000 claims abstract description 81
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 53
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 30
- 238000005119 centrifugation Methods 0.000 claims abstract description 24
- 238000001035 drying Methods 0.000 claims abstract description 15
- 239000007789 gas Substances 0.000 claims description 73
- 238000010521 absorption reaction Methods 0.000 claims description 69
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 46
- 238000001816 cooling Methods 0.000 claims description 41
- 238000003756 stirring Methods 0.000 claims description 41
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 36
- 239000008367 deionised water Substances 0.000 claims description 33
- 229910021641 deionized water Inorganic materials 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 29
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 238000010438 heat treatment Methods 0.000 claims description 24
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 24
- 239000012943 hotmelt Substances 0.000 claims description 19
- 238000002844 melting Methods 0.000 claims description 19
- 239000012452 mother liquor Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 15
- 239000001569 carbon dioxide Substances 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000011221 initial treatment Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000001105 regulatory effect Effects 0.000 claims description 8
- 239000010413 mother solution Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000005087 graphitization Methods 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 239000011148 porous material Substances 0.000 claims description 5
- 238000004321 preservation Methods 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 claims description 2
- 150000002531 isophthalic acids Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 238000010979 pH adjustment Methods 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 230000001276 controlling effect Effects 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000002699 waste material Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- HTXMGVTWXZBZNC-UHFFFAOYSA-N 3,5-bis(methoxycarbonyl)benzenesulfonic acid Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(S(O)(=O)=O)=C1 HTXMGVTWXZBZNC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000002920 hazardous waste Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical group COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 238000002834 transmittance Methods 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a production process of isophthalic acid-5-sodium sulfonate, and belongs to the field of isophthalic acid-5-sodium sulfonate. The production process of the isophthalic acid-5-sodium sulfonate comprises the following steps: sulfonation, neutralization, primary thermosol, primary crystallization, primary centrifugation, secondary thermosol, secondary crystallization, secondary centrifugation and drying. According to the production process of the isophthalic acid-5-sodium sulfonate, the prepared isophthalic acid-5-sodium sulfonate can obtain high purity and high yield, meanwhile, the product quality is effectively stabilized, the high quality is further realized, and meanwhile, the chromaticity index of the isophthalic acid-5-sodium sulfonate is improved.
Description
Technical Field
The invention relates to the field of isophthalic acid-5-sodium sulfonate, in particular to a production process of isophthalic acid-5-sodium sulfonate.
Background
Isophthalic acid-5-sulfonic acid sodium salt, also known as: 5- (sodium sulfo) iso-titanic acid, english code 5-SSIPA, is mainly used as water-soluble paint additive and important dyeing modifier for producing cation dyeable polyester, and can also be used as intermediate for producing medicines or pesticides, etc.
The isophthalic acid-5-sodium sulfonate is less than isophthalic acid dimethyl ester-5-sodium Sulfonate (SIPM) by two methyl ester groups, and is prepared by using isophthalic acid as a raw material, and directly neutralizing and refining after sulfonation without an esterification step. In the production of polyester using dimethyl isophthalate-5-Sulfonate (SIPM), dimethyl isophthalate-5-Sulfonate (SIPM) is first subjected to transesterification with ethylene glycol prior to the polymerization step, and dimethyl isophthalate-5-Sulfonate (SIPM) is converted to diethylene glycol isophthalate-5-Sulfonate (SIPE) and methanol is simultaneously produced. The polyester is produced by using isophthalic acid-5-sodium sulfonate, the transesterification reaction can be omitted, so that the polymerization step can be directly carried out by using isophthalic acid-5-sodium sulfonate, and methanol is not generated in the process. Therefore, isophthalic acid-5-sodium sulfonate (5-SSIPA) is used as a modifier to replace dimethyl isophthalate-5-sodium Sulfonate (SIPM) for the production of polyester, so that the process flow can be simplified, the reaction equipment can be saved, the public engineering construction can be reduced, the occupied area of production projects can be reduced, the production cost of polyester enterprises can be greatly reduced, and the environmental pollution in the production process can be reduced.
However, the inventor found that the existing production process of isophthalic acid-5-sodium sulfonate can obtain higher product purity, but in the industrial mass production process, the product quality is unstable, the superior product rate and yield index of the prepared isophthalic acid-5-sodium sulfonate are not ideal, and the superior product rate of isophthalic acid-5-sodium sulfonate cannot be ensured while realizing high purity and high yield. Furthermore, the poor chromaticity of the isophthalic acid-5-sodium sulfonate prepared by the existing production process can lead to the quality of downstream products, and the chromaticity index of the product needs to be further improved.
Chinese patent CN103992250a discloses a process for preparing dimethyl isophthalate-5-sodium sulfonate, in order to achieve ideal product purity and chromaticity index, the process steps of extraction, back extraction, adsorption and impurity removal are set up after the esterification process step in the technical scheme of the patent, which not only has long process flow, but also has many production equipments; in addition, new substances are introduced in the extraction and back extraction processes, so that the subsequent refining difficulty is increased, and the refining energy consumption is high.
Meanwhile, the inventor also discovers that in the existing production process of isophthalic acid-5-sodium sulfonate, 98% concentrated sulfuric acid is needed to be used as absorption acid for absorbing the sulfonated tail gas in the sulfonation process of isophthalic acid, but when the equivalent percentage concentration of sulfuric acid reaches 120%, the sulfuric acid cannot be continuously used as absorption acid for absorbing the sulfonated tail gas, and a certain amount of impurities such as isophthalic acid, pigment and the like exist in the absorption acid, so that the absorption acid can be used as hazardous waste treatment only; the waste liquid treatment device not only needs to be replaced frequently, but also has large waste liquid production amount and high hazardous waste treatment cost.
Disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a production process of isophthalic acid-5-sodium sulfonate, which can obtain high purity and yield of isophthalic acid-5-sodium sulfonate, has stable product quality, can realize high superior product rate of isophthalic acid-5-sodium sulfonate, and can improve chromaticity index of the product; further, the problems of frequent replacement of waste acid absorption, large production amount and high hazardous waste treatment cost in the existing production process of the isophthalic acid-5-sodium sulfonate are solved.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a production process of isophthalic acid-5-sodium sulfonate comprises the following steps: sulfonation, neutralization, primary thermosol, primary crystallization, primary centrifugation, secondary thermosol, secondary crystallization, secondary centrifugation and drying.
Mixing the sulfonated isophthalic acid and fuming sulfuric acid, and reacting for 3-4 hours at the temperature of 100-130 ℃ under the stirring condition; then continuously heating to 160-180 ℃, and carrying out heat preservation reaction for 2-3 hours to obtain a sulfonate;
the neutralization is carried out, the pH value of the sulfonate is regulated to 6.8-7.2, and then the neutralization centrifuge is used for preparing the neutralization centrifuge;
the neutralized centrifugate is subjected to primary thermosol, primary crystallization, primary centrifugation, secondary thermosol, secondary crystallization, secondary centrifugation and drying to obtain the isophthalic acid-5-sodium sulfonate.
Preferably, in the sulfonation, the molar ratio of isophthalic acid to fuming sulfuric acid is 1:1.2-1.3;
the fuming sulfuric acid is 60-65wt% fuming sulfuric acid.
Further, in the sulfonation process, the sulfonation tail gas is treated by adopting absorption acid;
the absorption acid is a mixture of fuming sulfuric acid with the concentration of 120% and fuming sulfuric acid with the concentration of 65%;
the weight ratio of the fuming sulfuric acid with the concentration of 120% to the fuming sulfuric acid with the concentration of 65% is 1:6.
The neutralization is carried out, the pH value is regulated to 6.8-7.2 after the sulfonate is uniformly mixed with a preset amount of deionized water, the mixture is stirred for a period of time, and then natural cooling and centrifugal separation are carried out, thus obtaining a neutralization centrifugate and a neutralization mother solution; carrying out primary thermosol on the neutralization centrifugal objects;
the neutralization mother solution is evaporated and concentrated to 35-40% of the original volume, and after the neutralization concentrated solution is prepared, primary hot melting is carried out.
Preferably, the weight ratio of the sulfonate to the deionized water is 1:1.5-2.5;
in the process of regulating the pH value, the temperature of the material in the neutralization kettle is kept within the range of 25-35 ℃.
The primary hot-melt, the neutralization centrifugate and the neutralization concentrated solution are mixed with the primary hot-melt solution, and the primary hot-melt is prepared by heating to 60-90 ℃ at the heating rate of 0.5-1 ℃/min under the stirring condition, and preserving heat and stirring for a period of time;
the volume ratio of the neutralization concentrated solution to the primary hot solution is 1:4-6;
the primary hot solution is deionized water or secondary crystallization mother liquor obtained in the secondary crystallization step.
The primary crystallization and primary thermosol prepared by primary thermosol are cooled to 60-65 ℃, and the primary thermosol is stirred for 1-2h after heat preservation; cooling to 40-45 ℃, preserving heat and stirring for 1-2 h; cooling to 20-25deg.C, maintaining the temperature and standing for 2-4 hr to obtain primary crystal;
and (3) carrying out primary centrifugation on the primary crystal to obtain a primary crystal centrifugate.
The secondary hot melting and primary centrifugation are carried out to prepare a primary crystallization centrifugate, and the primary crystallization centrifugate is mixed with deionized water; then contacting with a preset amount of modified activated carbon, heating to 85-95 ℃, preserving heat, stirring for a period of time, and filtering to obtain filtrate, thus obtaining a secondary thermosol;
the volume ratio of the primary crystallization centrifuge to deionized water is 1:6-8;
the volume ratio of the modified activated carbon to the deionized water is 0.2-0.3:1.
The modified activated carbon is prepared by modifying the activated carbon through primary treatment and secondary treatment;
the primary treatment is supercritical carbon dioxide treatment;
the temperature of the supercritical carbon dioxide treatment is 40-50 ℃ and the pressure is 9-12MPa;
the secondary treatment is activated carbon after primary treatment by liquid nitrogen impregnation;
the particle size of the active carbon is 50-80 meshes, and the specific surface area is 800-1000m 2 Per G, pore diameter of 1-3nm, graphitization degree G value by XRD65-70%.
The secondary crystallization is carried out, the temperature of the secondary thermosol prepared by the secondary thermosol is reduced to 60-65 ℃, and the secondary thermosol is kept at the temperature and stirred for 1-2 hours; cooling to 40-45 ℃, preserving heat and stirring for 1-2 h; cooling to 20-25 ℃, preserving heat and standing for 2-4h to obtain secondary crystals;
secondary crystallization centrifugate is obtained after secondary centrifugation of the secondary crystallization;
and (3) drying the secondary crystallization centrifugate at the temperature of 100-105 ℃ until the moisture content is less than 0.2wt% to obtain the isophthalic acid-5-sodium sulfonate.
Compared with the prior art, the invention has the beneficial effects that:
(1) According to the production process of the isophthalic acid-5-sodium sulfonate, a specific sulfonation process is arranged, and specific sulfonation tail gas treatment is arranged in the sulfonation step; recycling the neutralization concentrated solution to primary hot melting; setting a primary hot melting, a primary crystallization, a primary centrifugation, a secondary hot melting, a secondary crystallization and a secondary centrifugation of a specific process and flow; setting specific activated carbon treatment in the secondary hot-melting step; the prepared isophthalic acid-5-sodium sulfonate can obtain high purity and high yield, effectively stabilize the product quality, further realize high quality and improve the chromaticity index of the isophthalic acid-5-sodium sulfonate; meanwhile, the problems that the waste acid absorbed by the sulfonated tail gas needs to be replaced frequently, the production amount is large and the waste treatment cost is high in the existing production process of the isophthalic acid-5-sodium sulfonate can be effectively solved.
(2) The conversion rate of isophthalic acid is 98.6-98.9%, the purity of the prepared isophthalic acid-5-sodium sulfonate can reach 99.49-99.62%, the yield can reach 92.7-93.8%, and the high-grade product rate is 98-88%.
(3) According to the production process of the isophthalic acid-5-sodium sulfonate, the saponification value of the prepared isophthalic acid-5-sodium sulfonate is 417.8-418.1mgKOH/g, the chromaticity of platinum and cobalt (5 wt% aqueous solution) is 8-9, the 450nm transmittance (5 wt% aqueous solution) is 92.5-92.9%, and the moisture content is 0.17-0.18wt%.
(4) According to the production process of isophthalic acid-5-sodium sulfonate, on the premise of ensuring the absorption effect on sulfonated tail gas, the production of absorption waste acid is eliminated, the treatment cost of the absorption waste acid as dangerous waste is saved, and the production cost is saved; according to measurement and calculation, each ton of isophthalic acid-5-sodium sulfonate can save 420 yuan of treatment cost, and the economic benefit is further improved.
Detailed Description
Specific embodiments of the present invention will now be described in order to provide a clearer understanding of the technical features, objects and effects of the present invention.
Example 1
A production process of isophthalic acid-5-sodium sulfonate comprises the following specific process steps:
the sulfonation is carried out, a preset amount of isophthalic acid and fuming sulfuric acid are put into a sulfonation kettle, the temperature is raised to 100 ℃ under the stirring condition of 30rpm, and the reaction is carried out for 3 hours; then continuously heating to 160 ℃, preserving heat for 2 hours, and naturally cooling to obtain the sulfonate.
Wherein the molar ratio of isophthalic acid to fuming sulfuric acid is 1:1.2.
The oleum is 60wt% oleum.
In the sulfonation process, the produced sulfonation tail gas is led into a first tail gas absorption tank through a pipeline, and the sulfonation tail gas is discharged after being absorbed by absorption acid in the first tail gas absorption tank. Wherein the absorption acid in the first tail gas absorption tank is fuming sulfuric acid with the concentration of 98 percent.
When the equivalent percent concentration of sulfur trioxide in the absorption acid in the first tail gas absorption tank reaches 120%, introducing the sulfonated tail gas into the second tail gas absorption tank, and discharging the sulfonated tail gas after the sulfonated tail gas is absorbed by the absorption acid in the second tail gas absorption tank. Wherein the absorption acid in the second tail gas absorption tank is fuming sulfuric acid with the concentration of 98 percent.
And meanwhile, uniformly mixing the absorbing acid with the equivalent percent concentration of sulfur trioxide reaching 120% in the first tail gas absorbing tank with fuming sulfuric acid with the concentration of 65% according to the weight ratio of 1:6, and reintroducing the mixture into the first tail gas absorbing tank to be used as the absorbing acid.
Similarly, when the equivalent percent concentration of sulfur trioxide in the absorption acid in the second tail gas absorption tank reaches 120%, introducing the sulfonated tail gas into the first tail gas absorption tank for tail gas absorption. And meanwhile, uniformly mixing the absorbing acid with the equivalent percent concentration of sulfur trioxide reaching 120% in the second tail gas absorption tank with fuming sulfuric acid with the concentration of 65% according to the weight ratio of 1:6, and reintroducing the mixture into the second tail gas absorption tank to be used as the absorbing acid.
The first tail gas absorbing tank and the second tail gas absorbing tank are connected in parallel, and are used for one time.
The neutralization is carried out, the sulfonate is led into a neutralization kettle, a preset amount of deionized water is added under the stirring condition, and the stirring is continued for 20min after the addition of the deionized water is completed; then adding sodium hydroxide to adjust the pH value to 6.8, continuously stirring for 2 hours, and naturally cooling to 25 ℃; and then adopting a centrifugal speed of 5000rpm to centrifuge for 20min to obtain a neutralization centrifugate and a neutralization mother liquor. The neutralized centrifugate is put into a primary hot-melting kettle for primary hot-melting; the neutralized mother solution is put into an evaporation kettle, evaporated to 35% of the original volume in vacuum, and the neutralized concentrated solution is prepared and is introduced into a primary thermosol kettle for primary thermosol.
Wherein the weight ratio of the sulfonate to the deionized water is 1:1.5.
And in the process of regulating the pH value by adopting sodium hydroxide, the temperature of the materials in the neutralization kettle is kept within the range of 25-35 ℃.
The primary hot-melt is carried out, the primary hot-melt solution is put into a primary hot-melt kettle, mixed with a neutralization centrifuge and a neutralization concentrated solution, heated to 60 ℃ at a heating rate of 0.5 ℃/min under the stirring condition of 20rpm, continuously stirred for 30min, and the primary hot-melt is prepared and is led into a primary crystallization kettle.
Wherein the volume ratio of the neutralization concentrated solution to the primary hot solution is 1:4.
The primary hot solution is deionized water or secondary crystallization mother liquor.
The primary crystallization is carried out, the materials in the primary crystallization kettle are naturally cooled to 60 ℃, the temperature is kept, and the stirring is carried out for 1h at 10 rpm; controlling the cooling rate to be 0.2 ℃/min, cooling to 40 ℃, preserving heat, stirring for 1h at 3rmp, controlling the cooling rate to be 0.3 ℃/min, cooling to 20 ℃, preserving heat and standing for 2h, thus obtaining the primary crystal.
The primary centrifugation adopts a centrifugal speed of 5000rpm for 20min to prepare a primary crystallization centrifugate and a primary crystallization mother liquor; and (5) putting the primary crystallization centrifugate into a secondary thermosol kettle for secondary thermosol.
And (3) the secondary thermosol is carried out, deionized water is put into a secondary thermosol kettle, mixed with primary crystal centrifugate, added with a preset amount of modified active carbon under the stirring condition of 20rpm, then heated to 85 ℃ at the heating rate of 0.5 ℃/min, kept at the temperature, stirred for 30min at 100rpm, filtered to remove solid matters, and the filtrate is reserved, thus obtaining the secondary thermosol, and the secondary thermosol is led into the secondary crystallization kettle.
Wherein, the volume ratio of the primary crystallization centrifugate to the deionized water is 1:6.
The volume ratio of the modified activated carbon to the deionized water is 0.2:1.
The modified activated carbon is prepared by modifying by the following method:
1) One-time treatment
Putting the dried activated carbon into a high-pressure reaction kettle, introducing carbon dioxide, heating to a carbon dioxide supercritical state, and preserving heat and pressure for 5min; cooling and decompressing to obtain the active carbon after one-time treatment.
Wherein the supercritical carbon dioxide state temperature is 40 ℃ and the pressure is 9MPa.
The particle size of the activated carbon is 50 meshes, and the specific surface area is 800m 2 and/G, pore diameter of 1nm, graphitization degree G value of 65% measured by XRD.
2) Secondary treatment
Mixing the activated carbon after primary treatment with 1.2 times of liquid nitrogen, preserving heat and standing until the liquid nitrogen is completely evaporated at 20 ℃, then heating to 105 ℃, and preserving heat and performing heat treatment for 3 hours to obtain the modified activated carbon.
The secondary crystallization is carried out, materials in the secondary crystallization kettle are naturally cooled to 60 ℃, and the temperature is kept and the stirring is carried out for 1h at 10 rpm; controlling the cooling rate to be 0.2 ℃/min, cooling to 40 ℃, preserving heat, stirring for 1h at 3rmp, controlling the cooling rate to be 0.3 ℃/min, cooling to 20 ℃, preserving heat and standing for 2h, thus obtaining the secondary crystal.
The secondary centrifugation adopts a centrifugal speed of 6000rpm for 30min to prepare secondary crystallization centrifugate and secondary crystallization mother liquor; wherein, the secondary crystallization centrifugate is put into a dryer for drying; the secondary crystallization mother liquor is recycled to the primary hot melting and is used as the primary hot solution.
And drying the secondary crystallization centrifugate at the temperature of 100 ℃ until the moisture content is less than 0.2 weight percent to prepare the isophthalic acid-5-sodium sulfonate.
Example 2
A production process of isophthalic acid-5-sodium sulfonate comprises the following specific process steps:
the sulfonation is carried out, a preset amount of isophthalic acid and fuming sulfuric acid are put into a sulfonation kettle, the temperature is raised to 120 ℃ under the stirring condition of 40rpm, and the heat preservation reaction is carried out for 3.5 hours; then continuously heating to 170 ℃, preserving heat for 2.5h, and naturally cooling to obtain the sulfonate.
Wherein the molar ratio of isophthalic acid to fuming sulfuric acid is 1:1.25.
The oleum is 64wt% oleum.
In the sulfonation process, the produced sulfonation tail gas is led into a first tail gas absorption tank through a pipeline, and the sulfonation tail gas is discharged after being absorbed by absorption acid in the first tail gas absorption tank. Wherein the absorption acid in the first tail gas absorption tank is fuming sulfuric acid with the concentration of 98 percent.
When the equivalent percent concentration of sulfur trioxide in the absorption acid in the first tail gas absorption tank reaches 120%, introducing the sulfonated tail gas into the second tail gas absorption tank, and discharging the sulfonated tail gas after the sulfonated tail gas is absorbed by the absorption acid in the second tail gas absorption tank. Wherein the absorption acid in the second tail gas absorption tank is fuming sulfuric acid with the concentration of 98 percent.
And meanwhile, uniformly mixing the absorbing acid with the equivalent percent concentration of sulfur trioxide reaching 120% in the first tail gas absorbing tank with fuming sulfuric acid with the concentration of 65% according to the weight ratio of 1:6, and reintroducing the mixture into the first tail gas absorbing tank to be used as the absorbing acid.
Similarly, when the equivalent percent concentration of sulfur trioxide in the absorption acid in the second tail gas absorption tank reaches 120%, introducing the sulfonated tail gas into the first tail gas absorption tank for tail gas absorption. And meanwhile, uniformly mixing the absorbing acid with the equivalent percent concentration of sulfur trioxide reaching 120% in the second tail gas absorption tank with fuming sulfuric acid with the concentration of 65% according to the weight ratio of 1:6, and reintroducing the mixture into the second tail gas absorption tank to be used as the absorbing acid.
The first tail gas absorbing tank and the second tail gas absorbing tank are connected in parallel, and are used for one time.
The neutralization is carried out, the sulfonate is led into a neutralization kettle, a preset amount of deionized water is added under the stirring condition, and the stirring is continued for 30min after the addition of the deionized water is completed; then adding sodium hydroxide to adjust the pH value to 7.0, continuously stirring for 2.5 hours, and naturally cooling to 28 ℃; and then adopting a centrifugal speed of 5500rpm to centrifuge for 25min to obtain a neutralization centrifugate and a neutralization mother liquor. The neutralized centrifugate is put into a primary hot-melting kettle for primary hot-melting; the neutralized mother solution is put into an evaporation kettle, evaporated to 35% of the original volume in vacuum, and the neutralized concentrated solution is prepared and is introduced into a primary thermosol kettle for primary thermosol.
Wherein the weight ratio of the sulfonate to the deionized water is 1:2.
And in the process of regulating the pH value by adopting sodium hydroxide, the temperature of the materials in the neutralization kettle is kept within the range of 25-35 ℃.
The primary hot-melt is carried out, the primary hot-melt solution is put into a primary hot-melt kettle, mixed with a neutralization centrifuge and a neutralization concentrated solution, heated to 80 ℃ at a heating rate of 0.7 ℃/min under the stirring condition of 30rpm, continuously stirred for 40min, and the primary hot-melt is prepared and is led into a primary crystallization kettle.
Wherein the volume ratio of the neutralization concentrated solution to the primary hot solution is 1:5.
The primary hot solution is deionized water or secondary crystallization mother liquor.
The primary crystallization is carried out, the materials in the primary crystallization kettle are naturally cooled to 62 ℃, the temperature is kept, and the stirring is carried out for 1.5h at 15 rpm; the cooling rate is controlled to be 0.25 ℃/min, the temperature is reduced to 42 ℃, the temperature is kept, 5rmp is stirred for 1.5h, the cooling rate is controlled to be 0.4 ℃/min, the temperature is reduced to 22 ℃, the temperature is kept for 3h, and the primary crystal is prepared.
The primary centrifugation adopts a centrifugal speed of 5500rpm for 25min to prepare a primary crystallization centrifugate and a primary crystallization mother liquor; and (5) putting the primary crystallization centrifugate into a secondary thermosol kettle for secondary thermosol.
And (3) the secondary thermosol is carried out, deionized water is put into a secondary thermosol kettle, mixed with the primary crystal centrifugate, added with a preset amount of modified active carbon under the stirring condition of 40rpm, then heated to 90 ℃ at the heating rate of 0.7 ℃/min, kept at the temperature, stirred for 40min at 150rpm, filtered to remove solid matters, and the filtrate is reserved, thus obtaining the secondary thermosol, and the secondary thermosol is led into the secondary crystallization kettle.
Wherein, the volume ratio of the primary crystallization centrifugate to the deionized water is 1:7.
The volume ratio of the modified activated carbon to the deionized water is 0.25:1.
The modified activated carbon is prepared by modifying by the following method:
1) One-time treatment
Putting the dried activated carbon into a high-pressure reaction kettle, introducing carbon dioxide, heating to a carbon dioxide supercritical state, and preserving heat and pressure for 8min; cooling and decompressing to obtain the active carbon after one-time treatment.
Wherein the supercritical carbon dioxide state temperature is 45 ℃ and the pressure is 11MPa.
The particle size of the activated carbon is 70 meshes, and the specific surface area is 900m 2 and/G, pore diameter of 2nm, graphitization degree G value of 70% measured by XRD.
2) Secondary treatment
Mixing the activated carbon after primary treatment with 1.25 times of liquid nitrogen, preserving heat and standing until the liquid nitrogen is completely evaporated at 25 ℃, then heating to 110 ℃, and preserving heat and performing heat treatment for 5 hours to obtain the modified activated carbon.
The secondary crystallization is carried out, the materials in the secondary crystallization kettle are naturally cooled to 62 ℃, the temperature is kept, and the stirring is carried out for 1.5h at 15 rpm; controlling the cooling rate to be 0.25 ℃/min, cooling to 42 ℃, preserving heat, stirring for 1.5h at 5rmp, controlling the cooling rate to be 0.4 ℃/min, cooling to 22 ℃, preserving heat and standing for 3h, thus obtaining the secondary crystal.
The secondary centrifugation adopts a centrifugal speed of 6500rpm for 35min to prepare secondary crystallization centrifugate and secondary crystallization mother liquor; wherein, the secondary crystallization centrifugate is put into a dryer for drying; the secondary crystallization mother liquor is recycled to the primary hot melting and is used as the primary hot solution.
And drying, namely drying the secondary crystallization centrifugate at the temperature of 105 ℃ until the moisture content is less than 0.2 weight percent to obtain the isophthalic acid-5-sodium sulfonate.
Example 3
A production process of isophthalic acid-5-sodium sulfonate comprises the following specific process steps:
the sulfonation is carried out, a preset amount of isophthalic acid and fuming sulfuric acid are put into a sulfonation kettle, the temperature is raised to 130 ℃ under the stirring condition of 60rpm, and the reaction is carried out for 4 hours; then continuously heating to 180 ℃, preserving heat for 3 hours, and naturally cooling to obtain the sulfonate.
Wherein the molar ratio of isophthalic acid to fuming sulfuric acid is 1:1.3.
The oleum is 65wt% oleum.
In the sulfonation process, the produced sulfonation tail gas is led into a first tail gas absorption tank through a pipeline, and the sulfonation tail gas is discharged after being absorbed by absorption acid in the first tail gas absorption tank. Wherein the absorption acid in the first tail gas absorption tank is fuming sulfuric acid with the concentration of 98 percent.
When the equivalent percent concentration of sulfur trioxide in the absorption acid in the first tail gas absorption tank reaches 120%, introducing the sulfonated tail gas into the second tail gas absorption tank, and discharging the sulfonated tail gas after the sulfonated tail gas is absorbed by the absorption acid in the second tail gas absorption tank. Wherein the absorption acid in the second tail gas absorption tank is fuming sulfuric acid with the concentration of 98 percent.
And meanwhile, uniformly mixing the absorbing acid with the equivalent percent concentration of sulfur trioxide reaching 120% in the first tail gas absorbing tank with fuming sulfuric acid with the concentration of 65% according to the weight ratio of 1:6, and reintroducing the mixture into the first tail gas absorbing tank to be used as the absorbing acid.
Similarly, when the equivalent percent concentration of sulfur trioxide in the absorption acid in the second tail gas absorption tank reaches 120%, introducing the sulfonated tail gas into the first tail gas absorption tank for tail gas absorption. And meanwhile, uniformly mixing the absorbing acid with the equivalent percent concentration of sulfur trioxide reaching 120% in the second tail gas absorption tank with fuming sulfuric acid with the concentration of 65% according to the weight ratio of 1:6, and reintroducing the mixture into the second tail gas absorption tank to be used as the absorbing acid.
The first tail gas absorbing tank and the second tail gas absorbing tank are connected in parallel, and are used for one time.
The neutralization is carried out, the sulfonate is led into a neutralization kettle, a preset amount of deionized water is added under the stirring condition, and the stirring is continued for 40min after the addition of the deionized water is completed; then adding sodium hydroxide to adjust the pH value to 7.2, continuously stirring for 3 hours, and naturally cooling to 30 ℃; and then adopting a centrifugal speed of 6000rpm to centrifuge for 30min to obtain a neutralization centrifugate and a neutralization mother liquor. The neutralized centrifugate is put into a primary hot-melting kettle for primary hot-melting; the neutralized mother solution is put into an evaporation kettle, evaporated in vacuum to 40% of the original volume, and a neutralized concentrated solution is prepared and is introduced into a primary thermosol kettle for primary thermosol.
Wherein the weight ratio of the sulfonate to the deionized water is 1:2.5.
And in the process of regulating the pH value by adopting sodium hydroxide, the temperature of the materials in the neutralization kettle is kept within the range of 25-35 ℃.
The primary hot-melt is put into a primary hot-melt kettle, mixed with a neutralization centrifuge and a neutralization concentrated solution, heated to 90 ℃ at a heating rate of 1 ℃/min under the stirring condition of 60rpm, continuously stirred for 60min, and finally the primary hot-melt is obtained and is led into a primary crystallization kettle.
Wherein the volume ratio of the neutralization concentrated solution to the primary hot solution is 1:6.
The primary hot solution is deionized water or secondary crystallization mother liquor.
The primary crystallization is carried out, the materials in the primary crystallization kettle are naturally cooled to 65 ℃, and the temperature is kept and the stirring is carried out for 2 hours at 20 rpm; controlling the cooling rate to 0.3 ℃/min, cooling to 45 ℃, preserving heat, stirring for 2h at 6rmp, controlling the cooling rate to 0.5 ℃/min, cooling to 25 ℃, preserving heat and standing for 4h, thus obtaining the primary crystal.
The primary centrifugation adopts a centrifugal speed of 6000rpm for 30min to prepare a primary crystallization centrifugate and a primary crystallization mother liquor; and (5) putting the primary crystallization centrifugate into a secondary thermosol kettle for secondary thermosol.
And (3) the secondary thermosol is carried out, deionized water is put into a secondary thermosol kettle, mixed with the primary crystal centrifugate, a predetermined amount of modified active carbon is put under the stirring condition of 60rpm, then the temperature is raised to 95 ℃ at the heating rate of 1 ℃/min, the temperature is kept, the stirring time of 200rpm is 60min, then solid matters are filtered and filtered, and filtrate is reserved, thus obtaining the secondary thermosol, and the secondary thermosol is led into the secondary crystallization kettle.
Wherein, the volume ratio of the primary crystallization centrifugate to the deionized water is 1:8.
The volume ratio of the modified activated carbon to the deionized water is 0.3:1.
The modified activated carbon is prepared by modifying by the following method:
1) One-time treatment
Putting the dried activated carbon into a high-pressure reaction kettle, introducing carbon dioxide, heating to a carbon dioxide supercritical state, and maintaining the temperature and pressure for 10min; cooling and decompressing to obtain the active carbon after one-time treatment.
Wherein the supercritical carbon dioxide state is at 50 ℃ and the pressure is 12MPa.
The particle size of the activated carbon is 80 meshes, and the specific surface area is 1000m 2 and/G, pore diameter of 3nm, graphitization degree G value of 70% measured by XRD.
2) Secondary treatment
Mixing the activated carbon after primary treatment with 1.3 times of liquid nitrogen, preserving heat and standing until the liquid nitrogen is completely evaporated at the temperature of 30 ℃, then heating to 115 ℃, and preserving heat for 6 hours to obtain the modified activated carbon.
The secondary crystallization is carried out, the materials in the secondary crystallization kettle are naturally cooled to 65 ℃, and the temperature is kept and the stirring is carried out for 2 hours at 20 rpm; controlling the cooling rate to be 0.3 ℃/min, cooling to 45 ℃, preserving heat, stirring for 2h at 6rmp, controlling the cooling rate to be 0.5 ℃/min, cooling to 25 ℃, preserving heat and standing for 4h, thus obtaining the secondary crystal.
The secondary centrifugation adopts a centrifugal speed of 7000rpm for 40min to prepare secondary crystallization centrifugate and secondary crystallization mother liquor; wherein, the secondary crystallization centrifugate is put into a dryer for drying; the secondary crystallization mother liquor is recycled to the primary hot melting and is used as the primary hot solution.
And drying, namely drying the secondary crystallization centrifugate at the temperature of 105 ℃ until the moisture content is less than 0.2 weight percent to obtain the isophthalic acid-5-sodium sulfonate.
Comparative example 1
The technical scheme of the embodiment 2 is adopted, and the difference is that: 1) In the sulfonation step, 98% fuming sulfuric acid is used as absorption acid, when the equivalent percent concentration of sulfur trioxide in the absorption acid reaches 120%, the absorption acid is led out to dangerous waste treatment, and 98% fuming sulfuric acid is led in again to be used as new absorption acid. 2) The steps of primary thermosol, primary crystallization and primary centrifugation are omitted.
Comparative example 2
The technical scheme of the embodiment 2 is adopted, and the difference is that: in the secondary hot melting step, the active carbon which is of the same specification and is not subjected to primary treatment and secondary treatment is adopted to replace the modified active carbon for secondary hot melting treatment.
The indexes of the isophthalic acid-5-sodium sulfonate prepared in the examples 1-3 and the comparative examples 1-2 are detected; and compares the superior product specifications to calculate the superior product rate. Wherein, the specification of the isophthalic acid-5-sodium sulfonate superior product is as follows: the purity is more than or equal to 99.0%, the saponification value is 415-421mgKOH/g, the chromaticity of platinum and cobalt (5 wt% aqueous solution) is less than or equal to 12, and the moisture content is less than or equal to 0.2%.
The specific detection results are as follows:
the percentages used in the present invention are mass percentages unless otherwise indicated.
Finally, it should be noted that: the foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (3)
1. A process for producing isophthalic acid-5-sodium sulfonate, which is characterized by comprising the following steps: sulfonation, neutralization, primary thermosol, primary crystallization, primary centrifugation, secondary thermosol, secondary crystallization, secondary centrifugation and drying;
mixing the sulfonated isophthalic acid and fuming sulfuric acid, and reacting for 3-4 hours at the temperature of 100-130 ℃ under the stirring condition; then continuously heating to 160-180 ℃, and carrying out heat preservation reaction for 2-3 hours to obtain a sulfonate;
in the sulfonation, the molar ratio of isophthalic acid to fuming sulfuric acid is 1:1.2-1.3;
the fuming sulfuric acid is 60-65wt% fuming sulfuric acid;
in the sulfonation process, the sulfonation tail gas is treated by absorbing acid;
the absorption acid is a mixture of fuming sulfuric acid with the concentration of 120% and fuming sulfuric acid with the concentration of 65%;
the weight ratio of the fuming sulfuric acid with the concentration of 120% to the fuming sulfuric acid with the concentration of 65% is 1:6;
the neutralization is carried out, the pH value of the sulfonate is regulated to 6.8-7.2, and then the sulfonate is centrifuged to obtain a neutralized centrifuge;
the neutralized centrifugate is subjected to primary thermosol, primary crystallization, primary centrifugation, secondary thermosol, secondary crystallization, secondary centrifugation and drying to obtain isophthalic acid-5-sodium sulfonate;
the neutralization is carried out, the sulfonate is led into a neutralization kettle, after being uniformly mixed with a preset amount of deionized water, the pH value is regulated to 6.8-7.2, after being continuously stirred for a period of time, natural cooling and centrifugal separation are carried out, and the neutralization centrifugate and the neutralization mother solution are obtained;
the weight ratio of the sulfonate to the deionized water is 1:1.5-2.5;
evaporating and concentrating the neutralization mother liquor to 35-40% of the original volume to obtain a neutralization concentrated solution;
the primary hot-melt, the neutralization centrifugate and the neutralization concentrated solution are mixed with the primary hot-melt solution, and the primary hot-melt is prepared by heating to 60-90 ℃ at the heating rate of 0.5-1 ℃/min under the stirring condition, and preserving heat and stirring for a period of time;
the volume ratio of the neutralization concentrated solution to the primary hot solution is 1:4-6;
the primary hot solution is deionized water or secondary crystallization mother liquor obtained in the secondary crystallization step;
the primary crystallization and primary thermosol prepared by primary thermosol are cooled to 60-65 ℃, and the primary thermosol is stirred for 1-2h after heat preservation; cooling to 40-45 ℃, preserving heat and stirring for 1-2 h; cooling to 20-25deg.C, maintaining the temperature and standing for 2-4 hr to obtain primary crystal;
the primary crystallization centrifugate is prepared by primary centrifugation;
the secondary hot melting, the primary crystallization centrifugate is mixed with deionized water, then is contacted with a preset amount of modified activated carbon, is heated to 85-95 ℃, is kept warm and stirred for a period of time, and is filtered to obtain filtrate, thus obtaining a secondary hot melting substance;
the volume ratio of the primary crystallization centrifuge to deionized water is 1:6-8;
the volume ratio of the modified activated carbon to the deionized water is 0.2-0.3:1;
the modified activated carbon is prepared by modifying the activated carbon through primary treatment and secondary treatment;
the primary treatment is supercritical carbon dioxide treatment;
the temperature of the supercritical carbon dioxide treatment is 40-50 ℃ and the pressure is 9-12MPa;
the secondary treatment is activated carbon after primary treatment by liquid nitrogen impregnation;
the particle size of the activated carbon is 50-80 meshes, the specific surface area is 800-1000m < 2 >/G, the pore diameter is 1-3nm, and the graphitization degree G value measured by XRD is 65-70%.
2. The process for producing sodium isophthalic acid-5-sulfonate according to claim 1, wherein the temperature of the material in the neutralization tank is maintained within a range of 25 to 35 ℃ during the neutralization and pH adjustment.
3. The process for producing isophthalic acid-5-sodium sulfonate according to claim 1, wherein the secondary crystallization is carried out, the temperature of the secondary hot melt is reduced to 60-65 ℃, and the secondary hot melt is kept at a temperature and stirred for 1-2 hours; cooling to 40-45 ℃, preserving heat and stirring for 1-2 h; cooling to 20-25 ℃, preserving heat and standing for 2-4h to obtain secondary crystals;
secondary crystallization centrifugate is obtained after secondary centrifugation of the secondary crystallization;
and (3) drying the secondary crystallization centrifugate at the temperature of 100-105 ℃ until the moisture content is less than 0.2wt% to obtain the isophthalic acid-5-sodium sulfonate.
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