CN101585786B - Method of using SO<3>-air mixture to produce alkylphenol sulfonic acid and salts thereof via film sulfonator sulfonated alkylphenol - Google Patents
Method of using SO<3>-air mixture to produce alkylphenol sulfonic acid and salts thereof via film sulfonator sulfonated alkylphenol Download PDFInfo
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- CN101585786B CN101585786B CN2009100321001A CN200910032100A CN101585786B CN 101585786 B CN101585786 B CN 101585786B CN 2009100321001 A CN2009100321001 A CN 2009100321001A CN 200910032100 A CN200910032100 A CN 200910032100A CN 101585786 B CN101585786 B CN 101585786B
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- alkylphenol
- air mixture
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- sulfonic acid
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Abstract
A method of using SO3-air mixture to produce alkylphenol sulfonic acid and salts thereof through sulfonating the alkylphenol via a film sulfonator belongs to sulphonate preparing technology field. The invention uses alkylphenol as raw material, and uses the SO3-air mixture to sulfonate the raw material via the film sulfonator to obtain alkylphenol sulfonic acid, and uses alkaline solution such as NaOH to neutralize thealkylphenol sulfonic acid to obtain alkylphenol sulphonate. The alkylphenol used is a alkylphenol containing one or two C1-C20 straight-chain or branched chain alkyl. The alkylphenol sulfonic acid and salt thereof prepared by the method has high sulphonation rate, low free oil content, low inorganic salt content and producing no spend acid, which is no corrosion to equipments and helpful for environmental protection.
Description
Technical field
The present invention relates to a kind of SO of using
3The method that-air mixture is produced alkyl phenol sulfonic and salt thereof through the film sulfonator sulfonated alkylphenol belongs to the sulphonate preparing technical field.This sulfonic acid and salt thereof can also can be used as the dye well pharmaceutical intermediate as tensio-active agent or the important source material of producing tensio-active agent.
Technical background
Play an important role in sulfonating reaction process and the Technology in Modern chemical field.Sulfoacid compound and alkyl sodium sulfate ester cpds are one of present consumption maximum, most widely used AS kind.
The sulfonation production technology is at home and abroad all developed rapidly at present.Adoptable method of sulfonating mainly contains SO in the industry
3Sulfonation method, concentrated acid sulfonation method, oleum method of sulfonation, chlorsulfonic acid sulfonation method etc.
Since the 1950's, all be devoted to SO both at home and abroad
3The research of sulfonation technology, and obtained remarkable progress.The process for sulfonation that develops at present has multiple, like gaseous state SO
3Sulfonation method, liquid SO
3Sulfonation method, SO
3-solvent sulfonation method and SO
3Complex compound location sulfonation method.Gaseous state SO
3Sulfonation method mainly is to use SO
3-air mixture is made sulphonating agent, and its advantage is: do not generate water, SO
3Consumption can be near theoretical consumption, reaction is fast, " three wastes " are few, no spent acid produces, and is little to equipment corrosion, helps environment protection, so technology is advanced, the state of the art height is applied in industry, becomes consistent in the world advanced process for sulfonation of generally acknowledging.Gaseous state SO
3Sulfonation method is again to use SO in the falling film type sulphonator
3The sulfonation reaction that-air mixture carries out industry member the most is good.
China introduces the first cover SO since early 1980s
3Since the gas membrane type xanthator, in nearly 30 years course, China SO
3Gas membrane type sulfonation technology keeps the high speed development impetus always.At present; Various film sulfonation reactors and other key equipments, instrument realize production domesticization basically; Multiple industrial sulfonated product is produced in success on various film sulfonation reactors; Like sulfonated petro-leum (PS), alkyl benzene sulphonate(ABS) (LBS), heavy alkylbenzene sulfonic acid (HLBS), fatty alcohol sulfate salt (K-12), polyoxyethylene alkyl ether sulfate salt (AES), sulfonated (AOS), MES (MES) etc., but Shang Weijian adopts SO
3-air mixture is produced the report of alkyl phenol sulfonate through the film sulfonator sulfonated alkylphenol.Patent CN 1239477C once disclosed a kind of with the method for chlorsulfonic acid at organic solvent phase discontinuous formula sulfonation phenols; But the main sulfonated of this patent is the dihydric phenol or the UVNUL MS-40 phenol derivatives of short chain; It is lower that the sulphonated phenol of producing reclaims productive rate; Need to consume a large amount of organic solvents, and through neutralization the very high disadvantage of inorganic salt content is arranged with the sulphonated phenol product of chlorsulfonic acid process for sulfonation production.
Summary of the invention
The present invention proposes a kind of SO of using
3-air mixture is produced the method for alkyl phenol sulfonic and salt thereof through the film sulfonator sulfonated alkylphenol.The alkyl phenol sulfonic that this preparation method produces and the sulphonation rate of salt is high, free oil content is low, inorganic salt content is low, no spent acid generation, little to equipment corrosion, help environment protection.
The general molecular formula of this alkyl phenol sulfonic and salt thereof is following:
M is H, basic metal, ammonium or amido in the formula; R
1Be C
1～C
20The straight or branched alkyl; R
2Be H or C
1～C
20The straight or branched alkyl.
Technical scheme of the present invention: the preparation method of a kind of alkyl phenol sulfonic and salt thereof, use SO
3-air mixture is through the film sulfonator sulfonated alkylphenol, and step is:
A) with alkylphenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With the alkylphenol mol ratio be 1.0～1.5: 1, SO
3SO in the-air mixture
3Volumetric concentration is 2%～8%; Sulfonation temperature is 20～80 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 0～2 hour down in 20～80 ℃, obtains alkyl phenol sulfonic;
Used alkylphenol is for containing 1 or 2 C
1～C
20The alkylphenol of straight or branched alkyl;
B) add water in He in the still, add alkyl phenol sulfonic and liquid caustic soda, under 20～80 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain alkyl phenol sulfonic salt brine solution or slip; Wherein said alkali is mineral alkali or organic bases.
In the step a), the sulfonation reaction temperature is 30～60 ℃, SO
3With the alkylphenol mol ratio be 1.05～1.3: 1, SO
3SO in the-air mixture
3Volumetric concentration is 3%～5%, and digestion time is 0.5～1 hour.
In the step b), the neutralization reaction temperature is 30～60 ℃, and described mineral alkali is NaOH, KOH or NH
4OH; Described organic bases is monoethanolamine, diethylolamine, trolamine or tetraalkylammonium hydroxide.
Beneficial effect of the present invention: the alkyl phenol sulfonic and the salt thereof of the inventive method preparation, used alkylphenol is for containing 1 or 2 C
1～C
20The alkylphenol of straight or branched alkyl, sulphonation rate is high, free oil content is low, inorganic salt content is low, no spent acid generation, little to equipment corrosion, help environment protection.
Embodiment
Embodiment 1: the preparation of cresols potassium sulfonate
With cresols and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With the cresols mol ratio be 1.05: 1, SO
3SO in the-air mixture
3Volumetric concentration is 3%; Sulfonation temperature is 30 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wears out half a hour down in sulfonation temperature, obtains cresols sulfonic acid; In with still in adding technology water, add cresols sulfonic acid and potassium hydroxide solution, under 30 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 50% cresols potassium sulfonate.
The preparation of embodiment 2:2-sec-butyl phenol ammonium sulphonate
With 2-sec-butyl phenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With 2-sec-butyl phenol mol ratio be 1.3: 1, SO
3SO in the-air mixture
3Volumetric concentration is 4%; Sulfonation temperature is 40 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 45 minutes down in sulfonation temperature, obtains 2-sec-butyl phenol sulfonic acid; In with still in adding technology water, add 2-sec-butyl phenol sulfonic acid and mass concentration and be 28% solution of ammonium hydroxide, under 40 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 50% 2-sec-butyl phenol ammonium sulphonate.
Embodiment 3: to the preparation of special tert-pentyl phenol sulfonic acid monoethanolamine salt
Will be to special tert-pentyl phenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3Be 1.1: 1 to special tert-pentyl phenol mol ratio, SO
3SO in the-air mixture
3Volumetric concentration is 5%; Sulfonation temperature is 50 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 1 hour down in sulfonation temperature, obtains special tert-pentyl phenol sulfonic acid; In with still in adding technology water, add special tert-pentyl phenol sulfonic acid and monoethanolamine, under 50 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 60% to special tert-pentyl phenol sulfonic acid monoethanolamine salt.
Embodiment 4: the preparation of octyl phenol sodium sulfonate
With octyl phenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With the octyl phenol mol ratio be 1.1: 1, SO
3SO in the-air mixture
3Volumetric concentration is 4%; Sulfonation temperature is 50 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 45 minutes down in sulfonation temperature, obtains octyl phenol sulfonic acid; In with still in adding technology water, add octyl phenol sulfonic acid and sodium hydroxide solution, under 50 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 50% octyl phenol sodium sulfonate.
Embodiment 5: the preparation of NP sodium sulfonate
With NP and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With the NP mol ratio be 1.05: 1, SO
3SO in the-air mixture
3Volumetric concentration is 5%; Sulfonation temperature is 40 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 30 minutes down in sulfonation temperature, obtains NP sulfonic acid; In with still in adding technology water, add NP sulfonic acid and sodium hydroxide solution, under 50 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 50% NP sodium sulfonate.
Embodiment 6: the preparation of dodecyl natrium phenolsulfonicum
With 4-dodecylphenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With the 4-dodecylphenol mol ratio be 1.1: 1, SO
3SO in the-air mixture
3Volumetric concentration is 4%; Sulfonation temperature is 50 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 45 minutes down in sulfonation temperature, obtains 4-dodecylphenol sulfonic acid; In with still in adding technology water, add 4-dodecylphenol sulfonic acid and sodium hydroxide solution, under 40 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 50% dodecyl natrium phenolsulfonicum.
Embodiment 7: the preparation of a pentadecyl phenol sulfonic acid diethanolamine salt
With pentadecyl phenol and SO between fused
3-air mixture measures respectively to be squeezed in the film sulfonator, wherein SO
3With the 4-dodecylphenol mol ratio be 1.2: 1, SO
3SO in the-air mixture
3Volumetric concentration is 3%; Sulfonation temperature is 60 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 1 hour down in sulfonation temperature, obtains a pentadecyl phenol sulfonic acid; In with still in adding technology water, pentadecyl phenol sulfonic acid and diethylolamine between adding carry out neutralization reaction under 40 ℃, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 30% between pentadecyl phenol sulfonic acid diethanolamine salt.
Embodiment 8: the preparation of hexadecyl potassium phenolsulfonate
With hexadecyl phenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With hexadecyl phenol mol ratio be 1.1: 1, SO
3SO in the-air mixture
3Volumetric concentration is 5%; Sulfonation temperature is 50 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 45 minutes down in sulfonation temperature, obtains hexadecyl phenol sulfonic acid; In with still in adding technology water, add hexadecyl phenol sulfonic acid and potassium hydroxide solution, under 60 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 50% hexadecyl potassium phenolsulfonate.
Embodiment 9: the preparation of binonylphenol sulfonic acid triethanolamine salt
With binonylphenol and SO
3-air mixture measures respectively to be squeezed in the film sulfonator, wherein SO
3With the binonylphenol mol ratio be 1.3: 1, SO
3SO in the-air mixture
3Volumetric concentration is 5%; Sulfonation temperature is 80 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 1 hour down in sulfonation temperature, obtains binonylphenol sulfonic acid; In with still in adding technology water, add binonylphenol sulfonic acid and trolamine, under 60 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7～9, obtain mass concentration and be 40% binonylphenol sulfonic acid trolamine.
Claims (4)
1. the preparation method of alkyl phenol sulfonic and salt thereof is characterized in that using SO
3-air mixture must be made alkyl phenol sulfonic through the film sulfonator sulfonated alkylphenol, obtains alkyl phenol sulfonate with the liquid caustic soda neutralization again,
The general molecular formula of this alkyl phenol sulfonic and salt thereof is:
M is H, basic metal, ammonium or amido in the formula; R
1Be C
1-C
20The straight or branched alkyl, R
2Be H or C
1-C
20The straight or branched alkyl;
Step is:
A) with alkylphenol and SO
3-air mixture is metered into respectively in the film sulfonator, wherein SO
3With the alkylphenol mol ratio be 1.0-1.5: 1, SO
3SO in the-air mixture
3Volumetric concentration is 2%-8%; Sulfonation temperature is 20-80 ℃, and sulfonation reaction is instantaneous successive reaction; Reaction product is behind gas-liquid separator, and liquid portion gets into aging still and wore out 0-2 hour down in 20-80 ℃, obtains alkyl phenol sulfonic;
B) add water in He in the still, add alkyl phenol sulfonic and liquid caustic soda, under 20-80 ℃, carry out neutralization reaction, stirred 2 hours, make product pH value reach 7-9, obtain alkyl phenol sulfonic salt brine solution or slurry; Wherein said alkali is mineral alkali or organic bases.
2. the preparation method of alkyl phenol sulfonic according to claim 1 and salt thereof is characterized in that in the step a), and the sulfonation reaction temperature is 30-60 ℃, 8O
3With the alkylphenol mol ratio be 1.05-1.3: 1, SO
3SO in the-air mixture
3Volumetric concentration is 3%-5%; Digestion time is 0.5-1 hour.
3. the preparation method of alkyl phenol sulfonic according to claim 1 and salt thereof is characterized in that in the step b), and the neutralization reaction temperature is 30-60 ℃.
4. the preparation method of alkyl phenol sulfonic according to claim 1 and salt thereof is characterized in that in the step b), and described mineral alkali is NaOH, KOH or NH
4OH; Described organic bases is monoethanolamine, diethylolamine, trolamine or tetraalkylammonium hydroxide.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100321001A CN101585786B (en) | 2009-07-09 | 2009-07-09 | Method of using SO<3>-air mixture to produce alkylphenol sulfonic acid and salts thereof via film sulfonator sulfonated alkylphenol |
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|---|---|---|---|
| CN2009100321001A CN101585786B (en) | 2009-07-09 | 2009-07-09 | Method of using SO<3>-air mixture to produce alkylphenol sulfonic acid and salts thereof via film sulfonator sulfonated alkylphenol |
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| Publication Number | Publication Date |
|---|---|
| CN101585786A CN101585786A (en) | 2009-11-25 |
| CN101585786B true CN101585786B (en) | 2012-05-23 |
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| CN2009100321001A Active CN101585786B (en) | 2009-07-09 | 2009-07-09 | Method of using SO<3>-air mixture to produce alkylphenol sulfonic acid and salts thereof via film sulfonator sulfonated alkylphenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093551B (en) * | 2010-12-10 | 2012-11-21 | 江南大学 | Method for preparing alkylphenol polyether sulfate |
| CN106431994B (en) * | 2016-09-09 | 2018-02-02 | 江南大学 | Use SO3The method that air membrane-type sulfonation prepares alkyl dimethyl benzyl sulfobetaines |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468938A (en) * | 1966-10-21 | 1969-09-23 | Gaf Corp | Method of preparing sulfonated hydroxybenzophenone |
| US3697573A (en) * | 1970-05-05 | 1972-10-10 | Chevron Res | Linear alkylphenol sulfate-sulfonate phosphate-free detergent actives |
| US5072034A (en) * | 1988-07-20 | 1991-12-10 | Basf Aktiengesellschaft | Preparation of 4-alkoxy-2-hydroxybenzophenone-5-sulfonic acids |
| CN1143064A (en) * | 1996-07-12 | 1997-02-19 | 天津大学 | Method for sulfonating liquid state organics by gas phase sulfur trioxide and its equipment |
| US5919975A (en) * | 1996-05-31 | 1999-07-06 | Witco Corporation | Aromatic and aliphatic sulfonates and properties and applications thereof |
| US6384271B1 (en) * | 2001-05-04 | 2002-05-07 | E.I. Du Pont De Nemours And Company | Sulfonation, sulfation and sulfamation |
| CN1556792A (en) * | 2001-09-22 | 2004-12-22 | �����ѧ��˾ŷ�ֹ�˾ | Sulphonation of phenols |
-
2009
- 2009-07-09 CN CN2009100321001A patent/CN101585786B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468938A (en) * | 1966-10-21 | 1969-09-23 | Gaf Corp | Method of preparing sulfonated hydroxybenzophenone |
| US3697573A (en) * | 1970-05-05 | 1972-10-10 | Chevron Res | Linear alkylphenol sulfate-sulfonate phosphate-free detergent actives |
| US5072034A (en) * | 1988-07-20 | 1991-12-10 | Basf Aktiengesellschaft | Preparation of 4-alkoxy-2-hydroxybenzophenone-5-sulfonic acids |
| US5919975A (en) * | 1996-05-31 | 1999-07-06 | Witco Corporation | Aromatic and aliphatic sulfonates and properties and applications thereof |
| CN1143064A (en) * | 1996-07-12 | 1997-02-19 | 天津大学 | Method for sulfonating liquid state organics by gas phase sulfur trioxide and its equipment |
| US6384271B1 (en) * | 2001-05-04 | 2002-05-07 | E.I. Du Pont De Nemours And Company | Sulfonation, sulfation and sulfamation |
| CN1556792A (en) * | 2001-09-22 | 2004-12-22 | �����ѧ��˾ŷ�ֹ�˾ | Sulphonation of phenols |
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Effective date of registration: 20211111 Address after: 225400 No. 11 Zha South Road, Taixing Economic Development Zone, Taizhou City, Jiangsu Province Patentee after: Taixing Lingfei Chemical Technology Co., Ltd Address before: School of chemistry and materials engineering, Jiangnan University, 1800 Lihu Avenue, Wuxi, Jiangsu 214122 Patentee before: Jiangnan University |