CN1244523C - Sulfonation process for producing dye dispersant and concrete water reducing agent - Google Patents
Sulfonation process for producing dye dispersant and concrete water reducing agent Download PDFInfo
- Publication number
- CN1244523C CN1244523C CN 03153000 CN03153000A CN1244523C CN 1244523 C CN1244523 C CN 1244523C CN 03153000 CN03153000 CN 03153000 CN 03153000 A CN03153000 A CN 03153000A CN 1244523 C CN1244523 C CN 1244523C
- Authority
- CN
- China
- Prior art keywords
- sulfonation
- azeotropic solvent
- aromatic hydrocarbon
- reducing agent
- dye dispersant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000006277 sulfonation reaction Methods 0.000 title claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 9
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000004568 cement Substances 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003350 kerosene Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002699 waste material Substances 0.000 abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000009833 condensation Methods 0.000 abstract description 5
- 230000005494 condensation Effects 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for producing a dye dispersant and a concrete water reducer by using aromatic hydrocarbon, which is characterized in that the aromatic hydrocarbon and concentrated sulfuric acid are mixed for sulfonation reaction, the molar ratio of the aromatic hydrocarbon to the concentrated sulfuric acid is 1: 0.9-1.3, and an azeotropic solvent is added in the sulfonation process, so that water generated by sulfonation is removed from a reaction system through azeotropy. Due to the addition of the azeotropic solvent,the water generated by sulfonation is discharged out of the reaction system in time to ensure complete sulfonation reaction, the prior purpose of realizing complete sulfonation by adopting excessive sulfuric acid is changed, and Na can be obtained by the sulfonation process and the procedures of hydrolysis, condensation and the like2SO4The product with the content of 1-10 percent improves the yield of the product, reduces the production of waste residue, improves the production benefit and reduces the pollution of the waste residue to the environment.
Description
Technical field
The present invention relates to make the method for dye dispersant and cement water reducing agent production about aromatic hydrocarbon.
Background technology
Traditional aromatic hydrocarbon is made the method for dye dispersant and cement water reducing agent manufacturing: aromatic hydrocarbon obtains dispersion agent through sulfonation, hydrolysis, condensation, neutralization, filtration, drying, and also drying does not manufacture liquid product.Its technology weak point: use the excessive vitriol oil that aromatic ring is carried out sulfonation in process of production, in and the time for removing these unnecessary SO
4 2-, add Ca (OH)
2, making it to generate sedimentary vitriol, this technology has also produced a large amount of CaSO when removal influences the product quality metal-salt
4In waste residue, owing to contain a large amount of synthetic active substances in the waste residue, thus reduced product yield, the more important thing is that the processing of waste residue and waste residue causes the pollution of environment.
Summary of the invention
The objective of the invention is to overcome the shortcoming of prior art, the process for sulfonation that provides a kind of production dye dispersant that has improved and cement water reducing agent to produce, utilize present method production dye dispersant and cement water reducing agent can significantly improve product yield, reduce or eliminate the generation of waste residue.
The present invention mixes aromatic hydrocarbon and carries out sulfonation reaction with the vitriol oil, the mol ratio that is characterized in the aromatic hydrocarbon and the vitriol oil is 1: 0.9～1.3, and in sulfonation process, adds azeotropic solvent, makes sulfonation generate water and shifts out reaction system through azeotropic.
Above-mentioned process for sulfonation makes sulfonation generate water and in time discharges reaction system owing to add azeotropic solvent, guarantees that sulfonation reaction is complete, changes and adopts excess sulfuric acid to realize complete sulfonated purpose in the past.
Through above-mentioned process for sulfonation, enter operations such as hydrolysis, condensation again, can obtain Na
2SO
4The product of content in 1%～10% scope improved the yield of product, and reduces waste residue production, improves productivity effect, reduces the pollution of waste residue to environment.
Azeotropic solvent among the present invention can be hexanaphthene or ethylene dichloride or Benzene Chloride or kerosene or its arbitrary combination.
Be effectively control reaction, azeotropic solvent of the present invention adopts the dropping method to add in the sulfonation reaction still; When sulfonation acidity reaches prescribed value, then stop to drip.
Specific embodiment
Example one: produce the 1100kg dye dispersant
Take by weighing the 600kg methylnaphthalene respectively, 98% vitriol oil 450kg.
The methylnaphthalene and the vitriol oil are dropped into the sulfonation reaction still, be warming up to 160 ℃, drip the azeotropic solvent of being made up of hexanaphthene and Benzene Chloride, react after 2 hours, acidity is 20 ± 1% o'clock, stops to drip azeotropic solvent.The azeotropic solvent that steams enters water-and-oil separator, and azeotropic solvent recycles, and sour water is discharged after neutralizing treatment.The material of sulfonation reaction still adds formaldehyde condensation after 3～6 hours more in proportion after hydrolysis, add the 30%NaOH aqueous solution, and adjusting pH value is 7～8, and drying gets product 1100kg, and every index is as follows:
Outward appearance: pale yellow powder
Scatter coefficient: 101～102%
PH value: 7～8
Heat-resistant stability: 5 grades
Water content: 4.5～4.9%
Na
2SO
4Content: 1.0～5.0%
Calcium ions and magnesium ions content: 0.02～0.03%
Example two: produce the 1200kg cement water reducing agent
Take by weighing the 600kg NAPTHALENE FLAKES. (INDUSTRIAL GRADE respectively, 98% vitriol oil 550kg.
The NAPTHALENE FLAKES. (INDUSTRIAL GRADE and the vitriol oil are dropped into the sulfonation reaction still respectively, stir, be warming up to 165 ℃, drip the mixture of azeotropic solvent ethylene dichloride and Benzene Chloride and kerosene, the entrainer cooling back that steams flows into oil-water separation tank, and azeotropic solvent recycles, and sour water discharges after neutralizing.After the insulation reaction 3 hours, surveying sulfonation acidity is 22 ± 1% o'clock, stops to drip azeotropic solvent.Sulfonation reaction still material dripped formaldehyde condensation 4～6 hours after hydrolysis, in and the time add 30% NaOH, 580～650kg, adjusting pH value is 7.5～8.0, the 1200kg product.Every index is as follows:
Outward appearance: light brown powder
Surface tension: 69.0mN/m
Na
2SO
4Content: 1～5%
PH value: 7.5～8.0
Flowing degree of net paste of cement: 225～230mm
Cl
-Content:＜0.5%
Above-mentioned azeotropic solvent also can be the mixture of ethylene dichloride and kerosene; Or the mixture of dichlorobenzene and hexanaphthene, kerosene; Or the mixture of trichloroethane and hexanaphthene; Or the mixture of hexanaphthene and trichloroethane, trichlorobenzene, kerosene.
Claims (4)
1, the process for sulfonation of dye dispersant and cement water reducing agent production, aromatic hydrocarbon mixed with the vitriol oil carry out sulfonation reaction, it is characterized in that aromatic hydrocarbon and vitriolic mol ratio are 1: 0.9～1.3, and in sulfonation process, add azeotropic solvent, make sulfonation generate water and shift out reaction system through azeotropic.
2,, it is characterized in that described azeotropic solvent is hexanaphthene or ethylene dichloride or Benzene Chloride or kerosene or its any two or more mixture according to the described technology of claim 1.
3,, it is characterized in that described azeotropic solvent adds in the reactor with the dropping method according to the described technology of claim 2.
4,, it is characterized in that when sulfonation acidity reaches prescribed value, stopping to drip azeotropic solvent according to the described technology of claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03153000 CN1244523C (en) | 2003-09-09 | 2003-09-09 | Sulfonation process for producing dye dispersant and concrete water reducing agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03153000 CN1244523C (en) | 2003-09-09 | 2003-09-09 | Sulfonation process for producing dye dispersant and concrete water reducing agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1522995A CN1522995A (en) | 2004-08-25 |
| CN1244523C true CN1244523C (en) | 2006-03-08 |
Family
ID=34287067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03153000 Expired - Fee Related CN1244523C (en) | 2003-09-09 | 2003-09-09 | Sulfonation process for producing dye dispersant and concrete water reducing agent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1244523C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104446097A (en) * | 2014-11-14 | 2015-03-25 | 浙江建研科之杰新材料有限公司 | Preparation method of dye dispersant and concrete naphthalene water reducer |
| CN105175289A (en) * | 2015-10-09 | 2015-12-23 | 江苏瑞燕橡塑助剂有限公司 | Aromatic hydrocarbon sulfonation method |
| CN108948787B (en) * | 2018-08-30 | 2020-08-28 | 浙江嘉成化工有限公司 | Dye dispersant and preparation method thereof |
-
2003
- 2003-09-09 CN CN 03153000 patent/CN1244523C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1522995A (en) | 2004-08-25 |
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Granted publication date: 20060308 Termination date: 20120909 |