CN103265460A - Alkyl diphenyl ether sulfonate and preparation method thereof - Google Patents
Alkyl diphenyl ether sulfonate and preparation method thereof Download PDFInfo
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- CN103265460A CN103265460A CN201310231134XA CN201310231134A CN103265460A CN 103265460 A CN103265460 A CN 103265460A CN 201310231134X A CN201310231134X A CN 201310231134XA CN 201310231134 A CN201310231134 A CN 201310231134A CN 103265460 A CN103265460 A CN 103265460A
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Abstract
The invention relates to a preparation method of a novel anionic surfactant alkyl diphenyl ether sulfonate. The preparation method specifically comprises the steps of: with diphenyl ether and alpha-olefin as main raw materials, in the presence of solid acid catalyst, preserving heat for 1-5 hours under the temperature condition of 80-180 DEG C to produce an intermediate product alkyl diphenyl ether, then adding an inert organic solvent and a sulfonating agent for sulfonating at 0-80 DEG C to produce alkyl diphenyl ether sulfonic acid, and adding an alkali neutralizing agent for neutralizing till the PH value is 6.5-7.5, so as to produce alkyl diphenyl ether sulfonate.
Description
Technical field
The invention belongs to chemical and make the field, be specifically related to a kind of alkyl diphenyl ether sulfonate and preparation method thereof.
Background technology
Alkyl diphenyl ether sulfonate mainly is divided into alkyl diphenyl ether monosulfonate, alkyl diphenyl ether disulfonate, two alkyl diphenyl ether disulfonate, domestic enterprise uses the whole dependence on import of these series product at present, the domestic composition problem that does not still have actual this product of solution does not have homemade goods yet and appears on the market.I address this problem by the effort more than 1 year, and the actual superior finished product of effect that synthesized.Through and external imported product relatively, surface tension when concentration 0.1%, all in the 29-31 dynes per centimeter, import substitutes fully.Product has extensive use at industrial circles such as oil production, textile printing and dyeing, latex processing.Product synthetic aspect, at present, when aromatic hydrocarbon carries out alkylation, alkylation adopts hydrochloric ether more, alkene and Fatty Alcohol(C12-C14 and C12-C18) are alkylating reagent, with preparation alkylation catalysts such as aluminum chloride and hydrochloric acid, but this method technology is loaded down with trivial details, by product is many, the catalyst treatment cost is big, and when Fatty Alcohol(C12-C14 and C12-C18) or alkene were done alkylation as alkylating reagent, also useful sulfuric acid was done alkylation catalyst, but it is big to do the catalyzer requirement with sulfuric acid, serious to equipment corrosion, and in alkylation process, easily cause the sulfonation in advance of phenyl ether, cause the alkylation difficulty, by product increases thus, and sulfuric acid sepn process complexity in the purification process after alkylation finishes takes time and effort, and sewage quantity is big.It is alkylation catalyst that the present invention adopts sulfonated styrene diethylene benzene copoly mer, has avoided the appeal problem, the alkylation quickness and high efficiency that becomes, and cleaning is a kind of very good processing method.
Summary of the invention
Goal of the invention: problem to be solved by this invention provides a kind of anion surfactant of import substitution like product, a kind of alkyl diphenyl ether sulfonate and preparation method thereof, and the present invention specifically realizes goal of the invention as follows:
(1) 1-10mol phenyl ether and 1-5mol a-alkene are dropped into the alkylated reaction still.(2) catalyst solid acid is dropped into reactor, and progressively be warmed up to 80-180 ℃, under this temperature condition, be incubated 1-5 hour, to reaction end.(3) will go up step product filtering solid acid catalyst.
(4) will go up step (3) filtrate high temperature rectifying or underpressure distillation, get 270-350 ℃ of cut, be the intermediate product alkyl diphenyl ether.(5) will go up step (4) alkyl diphenyl ether and send into the sulfonation still, again inert organic solvents be put into the sulfonation still, and progressively add the 1-10mol sulphonating agent and be incubated sulfonation 1-5 hour at 0-80 ℃ then.(6) add water 10-60% stirring in above-mentioned (5) product, static acid out divides after the layering and removes the spent acid water layer then, and oil reservoir is alkyl diphenyl ether sulfonic acid and ORGANIC SOLVENT MIXTURES.(7) the mixture decompression of above-mentioned (6) is heated up in a steamer except inert organic solvents, get the alkyl diphenyl ether sulfonic acid.(8) add water and add alkaline neutraliser 1-3mol to above-mentioned (7) gained alkyl diphenyl ether sulfonic acid and be neutralized to the mixture that pH value 6.5-7.5 gets alkyl diphenyl ether sulfonate and a small amount of insolubles.(9) above-mentioned (8) gained material is filtered, the filtering insolubles to desired content, gets light yellow finished product alkyl diphenyl ether sulfonate product to the filtrate thin up;
Effect of the present invention and benefit are:
(1) aspect synthetic technology: adopting sulfonated styrene diethylene benzene copoly mer is catalyzer, the alkylation still corrosion of having avoided sulfuric acid to bring as alkylation catalyst, and avoided production of by-products, and can remove by filter catalyzer, convenient and swift.(2) aspect economic benefit: substituted the like product of a large amount of imports, reduced the interests loss of national industry, and because the buying of production domesticization back becomes convenient, improved production and operation efficient.(3) aspect product performance: this excellent product performance, both had anti-strong acid, highly basic, properties such as inorganic salt, surface tension can reach the 29-31 dynes per centimeter when concentration 0.1%, and have remarkable emulsifying property, and cheap, and cost performance is good.Product also alternative commercially available alkylphenol polyoxyethylene, sodium alkyl benzene sulfonate, alkyl sodium sulfonate, fatty alcohol-polyoxyethylene ether in industrial circles such as oil production, textile printing and dyeing, latex processing, metal processing, surface cleaning.Aspect emulsification, dispersing property, acid-and base-resisting, inorganic salt, high-temperature behavior, be that present commercially available alkylphenol polyoxyethylene, sodium alkyl benzene sulfonate, fatty alcohol-polyoxyethylene ether etc. are wetting, the 2-10 of dispersion, emulsification class tensio-active agent doubly.When increasing substantially product stability in use and effect, reduce usage quantity significantly, reduced use cost, reduced the environmental pollution index because using tensio-active agent to cause simultaneously;
Embodiment is further illustrated the present invention below by embodiment, and this embodiment only is the present invention is described and never limits the present invention:
Embodiment 1
In reactor, add about 300 grams of phenyl ether, add about 168 gram C numbers and be 12 a-alkene, and add sulfonated styrene diethylene benzene copoly mer about 14 the gram, progressively temperature control is at 80-180 ℃, be incubated 1-5 hour, to reaction end, the sulfonated styrene diethylene benzene copoly mer of elimination, the underpressure distillation of heating, get the 270-350 cut, rectifying liquid is sent into the sulfonation still, add sherwood oil 200 grams and begin to drip 120 oleums, 400 grams in rectifying liquid, temperature control is at 0-80 ℃, reacted 1-5 hour, add water about 30% and stirred 0.5 hour, static acid out is treated to divide after the layering and is gone spent acid (can apply mechanically with the dense oleum of height when turning sour next sulfonation, to reduce discharge of wastewater), divide remove spent acid after, heat up in a steamer except sherwood oil, add water again and add liquid caustic soda and be neutralized to pH value 6.5-7.5 with a small amount of lime, filter, the filtrate moisturizing is about 45% to finished product content, gets about 1200 grams of disodium 4-dodecyl-2,4 '-oxydibenzenesulfonate finished product, reaches more than 99% with the a-alkene rate of collecting;
Embodiment 2
In reactor, add about 680 grams of phenyl ether, add about 336 gram C numbers and be 12 a-alkene, and add about 16 grams of sulfonated styrene diethylene benzene copoly mer, progressively temperature control is at 80-180 ℃, be incubated 1-5 hour, to reaction end, the sulfonated styrene diethylene benzene copoly mer of elimination, the underpressure distillation of heating, get the 270-350 cut, rectifying liquid is sent into the sulfonation still, in rectifying liquid, add methylene dichloride 100 grams, and begin to drip chlorsulfonic acid 235 grams, temperature control is at 0-80 ℃, and extract HCl gas simultaneously out, and finish reaction 1 hour, be warming up to 50 ℃, survey terminal point, after terminal point arrived, methylene dichloride was extracted in decompression out, added water and add liquid caustic soda to be neutralized to pH value 6.5-7.5 with a small amount of lime, filter, the filtrate moisturizing is about 45% to finished product content, gets about 1580 grams of two disodium 4-dodecyl-2,4 '-oxydibenzenesulfonate finished products, reaches more than 99% with the a-alkene rate of collecting;
Embodiment 3
In reactor, add about 300 grams of phenyl ether, add about 112 gram C numbers and be 8 a-alkene, and add sulfonated styrene diethylene benzene copoly mer about 14 the gram, progressively temperature control is at 80-180 ℃, be incubated 1-5 hour, to reaction end, the sulfonated styrene diethylene benzene copoly mer of elimination, the underpressure distillation of heating, get the 270-350 cut, rectifying liquid is sent into the sulfonation still, add sherwood oil 200 grams and begin to drip 120 oleums, 400 grams in rectifying liquid, temperature control is at 0-80 ℃, reacted 1-5 hour, add water about 30% and stirred 0.5 hour, static acid out is treated to divide after the layering and is gone spent acid (can apply mechanically with the dense oleum of height when turning sour next sulfonation, to reduce discharge of wastewater), divide remove spent acid after, heat up in a steamer except sherwood oil, add water again and add liquid caustic soda and be neutralized to pH value 6.5-7.5 with a small amount of lime, filter, the filtrate moisturizing is about 45% to finished product content, gets about 1100 grams of octyl phenyl ether sodium disulfonate finished product, reaches more than 99% with the a-alkene rate of collecting;
Embodiment 4
In reactor, add about 300 grams of phenyl ether, add about 168 gram C numbers and be 12 a-alkene, and add sulfonated styrene diethylene benzene copoly mer about 14 the gram, progressively temperature control is at 80-180 ℃, be incubated 1-5 hour, to reaction end, the sulfonated styrene diethylene benzene copoly mer of elimination, the underpressure distillation of heating, get the 270-350 cut, rectifying liquid is sent into the sulfonation still, add sherwood oil 200 grams and begin to drip 120 oleums, 100 grams in rectifying liquid, temperature control is at 0-80 ℃, reacted 1-5 hour, add water about 30% and stirred 0.5 hour, static acid out is treated to divide after the layering and is gone spent acid (can apply mechanically with the dense oleum of height when turning sour next sulfonation, to reduce discharge of wastewater), divide remove spent acid after, heat up in a steamer except sherwood oil, add water again and add liquid caustic soda and be neutralized to pH value 6.5-7.5 with a small amount of lime, filter, the filtrate moisturizing is about 45% to finished product content, gets about 970 grams of dodecyl phenyl ether sodium monosulfate finished product, reaches more than 99% with the a-alkene rate of collecting;
Embodiment 5
In reactor, add about 300 grams of phenyl ether, add about 253 gram C numbers and be 18 a-alkene, and add sulfonated styrene diethylene benzene copoly mer about 14 the gram, progressively temperature control is at 80-180 ℃, be incubated 1-5 hour, to reaction end, the sulfonated styrene diethylene benzene copoly mer of elimination, the underpressure distillation of heating, get the 270-350 cut, rectifying liquid is sent into the sulfonation still, add sherwood oil 200 grams and begin to drip 120 oleums, 400 grams in rectifying liquid, temperature control is at 0-80 ℃, reacted 1-5 hour, add water about 30% and stirred 0.5 hour, static acid out is treated to divide after the layering and is gone spent acid (can apply mechanically with the dense oleum of height when turning sour next sulfonation, to reduce discharge of wastewater), divide remove spent acid after, heat up in a steamer except sherwood oil, add water again and add liquid caustic soda and be neutralized to pH value 6.5-7.5 with a small amount of lime, filter, the filtrate moisturizing is about 45% to finished product content, gets about 1390 grams of octadecyl phenyl ether sodium disulfonate finished product, reaches more than 99% with the a-alkene rate of collecting;
Embodiment 6
In reactor, add about 300 grams of phenyl ether, add about 168 gram C numbers and be 12 a-alkene, and add sulfonated styrene diethylene benzene copoly mer about 4 the gram, progressively temperature control is at 80-180 ℃, be incubated 1-5 hour, to reaction end, the sulfonated styrene diethylene benzene copoly mer of elimination, the underpressure distillation of heating, get the 270-350 cut, rectifying liquid is sent into outer circulation stir the coordinated type reactor, and add sherwood oil 300 grams, start recycle pump, slowly in external circulation line, import sulphur trioxide 162 grams, and open the external circulation line refrigerating unit simultaneously, temperature control reacted 1-5 hour in 0-80 ℃, surveyed terminal point, after terminal point arrives, decompression extracts sherwood oil, 30 ℃ add the water hydrolysis after aging after, add the aqueous solution neutralization that contains trolamine 206 grams, be neutralized to pH value 6.5-7.5, moisturizing is about 45% to finished product content, gets about 1554 grams of dodecyl phenyl ether disulfonic acid triethanolamine salt finished product, reaches more than 99% with the a-alkene rate of collecting.
Claims (10)
1. alkyl diphenyl ether sulfonate and preparation method thereof, it is characterized in that, the preparation method comprises the steps and processing condition: (1) drops into the alkylated reaction still with 1-10mol phenyl ether and 1-5mol a-alkene, (2) catalyst solid acid is dropped into reactor, and progressively be warmed up to 80-180 ℃, under this temperature condition, be incubated 1-5 hour, to reaction end, (3) will go up step (2) product filtering solid acid catalyst, (4) will go up step (3) filtrate high temperature rectifying or underpressure distillation, get 270-350 ℃ of cut, be the intermediate product alkyl diphenyl ether, (5) will go up step (4) alkyl diphenyl ether and send into the sulfonation still, inert organic solvents is put into the sulfonation still again, progressively added the 1-10mol sulphonating agent and be incubated sulfonation 1-5 hour at 0-80 ℃ then, (6) add water 10-60% stirring in above-mentioned (5) product, static acid out then, divide after the layering and remove the spent acid water layer, oil reservoir is alkyl diphenyl ether sulfonic acid and ORGANIC SOLVENT MIXTURES
(7) the mixture decompression of above-mentioned (6) is heated up in a steamer except inert organic solvents, get the alkyl diphenyl ether sulfonic acid, (8) add water and add alkaline neutraliser 1-3mol to above-mentioned (7) gained alkyl diphenyl ether sulfonic acid and be neutralized to the mixture that pH value 6.5-7.5 gets alkyl diphenyl ether sulfonate and a small amount of insolubles, (9) above-mentioned (8) gained material is filtered, the filtering insolubles, to desired content, get light yellow finished product alkyl diphenyl ether sulfonate product to the filtrate thin up.
2. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: main raw material is: phenyl ether, a-alkene, sulphonating agent, alkaline neutraliser, and a-alkene wherein can be that the C number is 3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18 a-alkene.
3. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof is characterized in that: the synthesis material phenyl ether: a-alkene: sulphonating agent: the molar ratio of alkaline neutraliser is: 1-10: 1-5: 1-10: 1-3.
4. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described sulphonating agent comprises sulfuric acid, chlorsulfonic acid, thionamic acid, sulphur trioxide.
5. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described alkaline neutraliser is mineral alkali: sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate, lime etc. or organic amine series organic bases: trolamine, diethanolamine, thanomin, ammoniacal liquor, monomethylamine, dimethylamine, Trimethylamine 99, etc.
6. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described solid acid catalyst can be sulfonated styrene diethylene benzene copoly mer, tosic acid, toluenesulphonic acids, methylsulphonic acid, and ingredient proportion is the 1-40% of a-alkene and phenyl ether total amount.
7. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: sulfonic group can be ortho position, a position or the contraposition at Sauerstoffatom in the product structure, sulfonic number can be 1-2.
8. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof is characterized in that: the alkyl in the product structure can be two alkyl or monoalkyl, can be normal chain alkyl or isomery alkyl, can be in ortho position, a position or the contraposition of Sauerstoffatom.
9. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described inert organic solvents can be trichloromethane, methylene dichloride, 1,2-ethylene dichloride, 1,1,2,2 ,-tetrachloroethane, Nitromethane 99Min., trieline, tetracol phenixin, o-nitroethylbenzene, oil of mirbane, nitrotoluene, orthodichlorobenzene, sherwood oil etc., consumption is the 1-200% of material total amount.
10. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: finished product is that the pH value scope is at light yellowish brown or the light yellow liquid of 6.5-7.5.
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Cited By (6)
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| CN106699613A (en) * | 2016-11-10 | 2017-05-24 | 广东锦昱材料科技有限公司 | Efficient bifunctional anionic surfactant sodium alkyl diphenyl ether disulfonate taking trimeric butene as raw material |
| CN109293534A (en) * | 2018-09-19 | 2019-02-01 | 中国日用化学研究院有限公司 | A kind of preparation method and device of alkyl diphenyl ether sulfonate |
| CN109387600A (en) * | 2018-10-31 | 2019-02-26 | 广东丽臣奥威实业有限公司 | The measurement method of effective component in a kind of α olefin sulfonate product |
| CN111454130A (en) * | 2020-04-20 | 2020-07-28 | 中国日用化学研究院有限公司 | Process for preparing alkyl diphenyl ether by catalyzing reaction of olefin and diphenyl ether with solid acid |
| KR20200141849A (en) * | 2019-06-11 | 2020-12-21 | 금호석유화학 주식회사 | A method for manufacturing anionic surfactants |
| CN113861082A (en) * | 2021-11-12 | 2021-12-31 | 上海昶法新材料有限公司 | Method for synthesizing alkyl diphenyl ether disulfonic acid sodium by micro-channel reactor |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106699613A (en) * | 2016-11-10 | 2017-05-24 | 广东锦昱材料科技有限公司 | Efficient bifunctional anionic surfactant sodium alkyl diphenyl ether disulfonate taking trimeric butene as raw material |
| CN109293534A (en) * | 2018-09-19 | 2019-02-01 | 中国日用化学研究院有限公司 | A kind of preparation method and device of alkyl diphenyl ether sulfonate |
| CN109293534B (en) * | 2018-09-19 | 2021-10-12 | 中国日用化学研究院有限公司 | Preparation method and device of alkyl diphenyl ether sulfonate |
| CN109387600A (en) * | 2018-10-31 | 2019-02-26 | 广东丽臣奥威实业有限公司 | The measurement method of effective component in a kind of α olefin sulfonate product |
| KR20200141849A (en) * | 2019-06-11 | 2020-12-21 | 금호석유화학 주식회사 | A method for manufacturing anionic surfactants |
| KR102213048B1 (en) * | 2019-06-11 | 2021-02-08 | 금호석유화학 주식회사 | A method for manufacturing anionic surfactants |
| CN111454130A (en) * | 2020-04-20 | 2020-07-28 | 中国日用化学研究院有限公司 | Process for preparing alkyl diphenyl ether by catalyzing reaction of olefin and diphenyl ether with solid acid |
| CN113861082A (en) * | 2021-11-12 | 2021-12-31 | 上海昶法新材料有限公司 | Method for synthesizing alkyl diphenyl ether disulfonic acid sodium by micro-channel reactor |
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Application publication date: 20130828 |