CN115947935A - Allyl-terminated fatty alcohol polyoxyethylene ether and SO 3 Process for preparing fatty alcohol ether sulfonate by reaction - Google Patents
Allyl-terminated fatty alcohol polyoxyethylene ether and SO 3 Process for preparing fatty alcohol ether sulfonate by reaction Download PDFInfo
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Abstract
The invention discloses allyl-terminated fatty alcohol-polyoxyethylene ether and SO 3 The process for preparing the fatty alcohol ether sulfonate by the reaction comprises the following steps: SO (SO) 3 The dry air mixed gas enters the top of a membrane type sulfonator after being filtered, simultaneously, the allyl-terminated fatty alcohol-polyoxyethylene ether also enters the top of the sulfonator, circulating water is introduced into a jacket of the sulfonator to remove reaction heat release, and a sulfonated product leaves from the bottom of the sulfonator to finish the sulfonation reaction; the sulfonation product is a mixture of sulfonic acid and sultone; then neutralizing the sulfonated product with alkali solution, reacting sulfonic acid with alkali to generate corresponding sulfonate, finally hydrolyzing, and reacting sultone with alkali to obtain fatty alcohol ether sulfonate. The invention has the advantages of easily obtained raw materials, simple preparation process and high conversion rate, and the obtained product does not need to be extractedPure, can utilize the existing large-scale sulfonation device to carry out industrial production, and is safe and environment-friendly.
Description
Technical Field
The invention relates to a process for preparing an anionic surfactant fatty alcohol ether sulfonate by reacting allyl-terminated fatty alcohol-polyoxyethylene ether with sulfur trioxide gas, belonging to the field of preparation of anionic surfactants.
Background
The surfactant is known as industrial monosodium glutamate, and is widely applied to the fields of civil washing, personal care, mineral flotation, industrial cleaning, oilfield exploitation and the like. For certain high-temperature and high-mineralization environments, such as the fields of oil exploitation, industrial cleaning and the like, more severe requirements are put on the surfactant. Traditional anionic surfactants, such as alkylbenzenesulfonate (LAS), alpha-olefinsulfonate (AOS), have good temperature resistance, but poor hard water resistance; fatty alcohol polyoxyethylene ether sulfate (AES) is one of the most used anionic surfactants in the daily chemical industry, has good hard water resistance, but the sulfate bond in the molecule is unstable at high temperature and is easy to decompose, and the use in a high-temperature environment is limited. Therefore, the development of the anionic surfactant which is salt-resistant and high-temperature-resistant is of great significance.
The fatty alcohol ether sulfonate is an anionic-nonionic surfactant containing EO groups and sulfonic groups in molecules, has the characteristics of temperature resistance of the anionic surfactant and salt tolerance of the nonionic surfactant, and has great application prospects in extreme environments such as high temperature (more than 100 ℃), high salt (NaCl concentration more than 200 g/L) and the like. The surfactant has strong controllability of molecular structure, and can meet the requirements of different environments by adjusting the structure.
Synthesis method of fatty alcohol ether sulfonateMainly including a sulfate group conversion method, a sulfoalkylation method, an olefin addition method, a sulfite sulfonation method and the like. US4226807 proposes that alkyl alcohol ether sulfonate is obtained by reacting alkyl alcohol polyoxyethylene ether as raw material with KOH as catalyst and sodium isethionate at 180-190 deg.C under vacuum. N is introduced during the reaction 2 When the inert gas is used for removing the byproduct water, foams are generated in the reaction process, the conversion rate is only 70-80%, and the reaction is difficult to control. The preparation method comprises the steps of taking octyl phenol polyoxyethylene ether as a raw material, firstly reacting with thionyl chloride to obtain an intermediate, and synthesizing the octyl phenol polyoxyethylene ether sulfonate by taking sodium sulfite, a mixture of sodium sulfite and sodium bisulfite and potassium sulfite as sulfonating agents respectively, wherein the final yield is only 82.6%. The acidic waste gases HCl and SO are generated in the synthesis process 2 The environment is polluted, the equipment is corroded, and the industrial production is difficult to realize. Chinese patent (publication No. CN 101979426A) uses fatty alcohol (alkylphenol) polyoxyethylene ether as a raw material, and firstly undergoes allylation to obtain an allyl-terminated fatty alcohol polyoxyethylene ether intermediate, and sodium sulfite and sodium bisulfite (1. After the reaction is finished, a large amount of inorganic salt remains and needs to be removed by an organic solvent.
Chinese patent CN112680208A discloses a preparation process of oleyl alcohol ether sulfonate/sulfate, wherein the raw material molecules contain terminal alcoholic hydroxyl and internal olefin double bonds which respectively correspond to sulfation reaction and sulfonation reaction, and the sulfonation of the double bonds is the sulfonation of the internal olefin double bonds; the sulfonated intermediate is mainly beta-sultone; in addition, the raw material of the oleyl alcohol polyoxyethylene ether, namely oleyl alcohol, is relatively few in domestic resources, basically depends on import and is high in price.
Aiming at the defects of the technology, the invention provides a novel preparation process of fatty alcohol ether sulfonate.
Disclosure of Invention
The invention aims to provide allyl-terminated fatty alcohol-polyoxyethylene ether and SO 3 A process for preparing fatty alcohol ether sulfonate by reaction. The aliphatic alcohol ether sulfonate prepared by the invention contains EO groups and sulfonic acid groups simultaneously, and has the characteristics of temperature resistance and salt resistance. SO used in the invention 3 The membrane type sulfonation process is the most economical and efficient means for introducing sulfonic acid groups into molecules.
In the invention, SO is used 3 The alcohol ether sulfonate is a sulfonating agent and is prepared by reacting with allyl-terminated fatty alcohol-polyoxyethylene ether, the side reaction of the process is less, and the process belongs to a typical atom economic reaction; the process is continuous production, can be produced by using the existing industrialized sulfonation device, has high product purity, does not need to purify the product, and has high production efficiency and low cost. Compared with the prior patent application CN112680208A, the raw material adopted by the invention is allyl-terminated fatty alcohol-polyoxyethylene ether, and double bonds positioned at terminal positions are reacted. From the aspect of reaction, the two reactions are different, the prior technical scheme is that the sulfonation/sulfation reactions are both carried out, the sulfonation of a double bond is internal olefin sulfonation, the sulfonation of terminal olefin is carried out, a sulfonation intermediate is beta-sultone firstly, and then the beta-sultone and alkenyl sulfonic acid are rearranged, and the reaction mechanisms involved in the two reactions are completely different; the raw material oleyl alcohol of oleyl alcohol polyoxyethylene ether in the original patent application depends on import, and the raw material related to the invention has wide source and lower cost than the former.
The invention provides a preparation process of fatty alcohol ether sulfonate, which comprises the following specific steps:
SO 3 the method comprises the following steps of filtering dry air mixed gas, enabling the filtered dry air mixed gas to enter the top of a membrane type sulfonator, enabling allyl-terminated fatty alcohol-polyoxyethylene ether to enter the top of the sulfonator, enabling circulating water to be introduced into a jacket of the sulfonator to remove reaction heat, enabling a sulfonated product (a mixture of sulfonic acid and sultone) to leave from the bottom of the sulfonator to finish a sulfonation reaction, neutralizing the sulfonated product with an alkali solution, enabling the sulfonic acid and alkali to react to generate corresponding sulfonate, and finally performing hydrolysis (reaction of sultone and alkali) to obtain fatty alcohol ether sulfonate.
The allyl-terminated fatty alcohol-polyoxyethylene ether has the following structural formula:
wherein R is alkyl and the carbon chain is C 8 To C 18 One or any mixture of a plurality of the components; n =1 to 10.
In the invention, the allyl-terminated fatty alcohol polyoxyethylene ether and SO 3 Carrying out addition reaction to generate beta-sultone, quickly rearranging the beta-sultone into alkenyl sulfonic acid and gamma-sultone, namely, a sulfonated product leaving a sulfonator is a mixture of sulfonic acid and sultone, then neutralizing with alkali, carrying out neutralization reaction on the alkenyl sulfonic acid and the alkali to generate corresponding salt, finally hydrolyzing, and reacting the sultone and the alkali to generate corresponding sulfonate to obtain the target product, namely the fatty alcohol ether sulfonate. The reaction mechanism is shown in figure 3.
The product fatty alcohol ether sulfonate in the preparation process is a mixture of the following substances:
wherein R is alkyl and the carbon chain is C 8 To C 18 One or any mixture of a plurality of the components; m is alkali metal, including one of sodium, potassium and lithium.
In the preparation process, the process conditions are as follows: SO (SO) 3 In dry air mixture, SO 3 The volume ratio of the SO to the air is 2.5-4.0: 100 3 The mol ratio of the allyl-terminated fatty alcohol to the allyl-terminated fatty alcohol-polyoxyethylene ether is 1.00-1.10: 1, the temperature of the water jacket of the sulfonator is 20-70 ℃, the hydrolysis temperature is 90-150 ℃, and the hydrolysis time is 30-240 min.
SO as described above 3 In dry air mixture, SO 3 Is prepared from sulfur by combustion or liquid SO 3 Prepared by an evaporation method.
The alkali is one of sodium hydroxide, potassium hydroxide and lithium hydroxide.
The invention has the beneficial effects that:
(1) The method has the advantages of easily available raw materials, simple preparation process, high conversion rate, no need of purification of the obtained product, capability of utilizing the existing large-scale sulfonation device for industrial production, safety and environmental protection.
(2) The obtained sulfonate product can be used for being compatible with traditional anionic surfactant alkyl benzene sulfonate and alpha-olefin sulfonate, and the salt tolerance of an alkyl benzene sulfonate and alpha-olefin sulfonate compound system is improved;
(3) The fatty alcohol ether sulfonate obtained is compatible with the cationic surfactant, and the oil/water interfacial tension can be reduced to be ultralow (< 0.01 mN/m).
Drawings
FIG. 1 is an infrared spectrum of a raw material allyl-terminated fatty alcohol polyoxyethylene ether;
FIG. 2 is an infrared spectrum of a fatty alcohol ether sulfonate as a product obtained in example 2;
FIG. 3 shows allyl-terminated fatty alcohol polyoxyethylene ether and SO 3 A mechanism diagram for preparing fatty alcohol ether sulfonate through reaction.
Description of the preferred embodiment
The present invention is further illustrated by, but is not limited to, the following examples.
Example 1:
allyl-terminated isooctanol polyoxyethylene ether (n = 1) and SO obtained by the sulfur-burning method 3 Dry air reaction of mixed gases, SO 3 Volume ratio of air/SO 4.0% 3 The ratio of the allyl end capping isooctyl alcohol polyoxyethylene ether to the mole number is 1.00:1, the temperature of the circulating water of a sulfonator jacket is 20 ℃, a sulfonated product is neutralized by a lithium hydroxide solution, and the sulfonated product is hydrolyzed for 90min at 110 ℃ to obtain the fatty alcohol ether sulfonic acid lithium aqueous solution. The product had an unreacted content of 3.1% (based on 100% total solids) and a lithium sulfate content of 0.8% (based on 100% total solids).
And (3) performance testing: 0.5% of the fatty alcohol ether sulfonate is clarified in 200g/L NaCl solution in 1g/L CaCl 2 The solution is clear. The product was heated at 150 ℃ for 72h without decomposition. The prepared fatty alcohol ether sulfonate and dodecyl trimethyl ammonium chloride are compounded in a mass ratio of 6/4 (the total mass concentration is 0.2 percent), and then the interfacial tension between the fatty alcohol ether sulfonate and the kerosene is ultra-low<0.01 mN/m), interfacial tension test conditions: at a temperature of 50 ℃ toAnd preparing a surfactant solution by using the ionized water.
Example 2:
allyl end-capped Natural 12-14 alcohol (12 alcohol/14 alcohol mass ratio 75/25) polyoxyethylene ether (n = 7) with liquid SO 3 SO obtained by evaporation 3 Dry air reaction of mixed gases, SO 3 Volume ratio of air 3.0%, SO 3 The mol ratio of the allyl end capping natural 12-14 alcohol polyoxyethylene ether is 1.08:1, the temperature of the circulating water of a sulfonator jacket is 40 ℃, sulfonated products are neutralized by potassium hydroxide solution, and hydrolysis is carried out for 30min at 150 ℃, so as to obtain the fatty alcohol ether potassium sulfonate water solution. The unreacted content of the product was 3.6% (based on 100% total solids) and the sodium sulfate content was 1.0% (based on 100% total solids).
The infrared spectrums of the raw material allyl-terminated fatty alcohol-polyoxyethylene ether and the product fatty alcohol ether sulfonate are respectively shown in figures 1 and 2. FIG. 2 at 3480cm -1 The characteristic absorption peaks of hydroxyl groups appear at 1044 and 1226cm -1 Two new absorption peaks appear, and-SO 3 The Na characteristic absorption peaks coincide, indicating successful preparation of the product.
And (3) performance testing: 0.5% of the fatty alcohol ether sulfonate is clarified in 200g/L NaCl solution and in 10g/L CaCl 2 The solution is clear, and can meet the requirements of most application occasions. The fatty alcohol ether sulfonate and C 14-16 The alpha-sodium alkenyl sulfonate is compounded in a NaCl solution of 180g/L in a mass ratio of 5/5 (the total mass concentration is 0.5 percent) for clarification, so that the content of C is improved 14-16 Salt tolerance of sodium alpha-alkenyl sulfonate (0.5% C) 14-16 Sodium alpha-alkenyl sulfonate was cloudy in a 70g/L NaCl solution). The product was heated at 150 ℃ for 72h without decomposition. The interface tension between the prepared fatty alcohol ether sulfonate and the didecyl dimethyl ammonium chloride after being compounded by 4/6 (mass ratio, total mass concentration is 0.2 percent) and the kerosene can be ultra-low<0.01 mN/m), interfacial tension test conditions: the temperature is 50 ℃, and a surfactant solution is prepared from 50g/L NaCl solution.
Example 3:
allyl-terminated 16-18 alcohol (16 alcohol/18 alcohol mass ratio 60/40) polyoxyethylene ether (n = 5) with passing liquid SO 3 By evaporation to obtainObtained SO 3 Dry air reaction of mixed gases, SO 3 Air volume ratio 2.5%, SO 3 The mol ratio of the allyl end capping 16-18 alcohol polyoxyethylene ether is 1.10:1, the temperature of the circulating water of a sulfonator jacket is 70 ℃, a sulfonated product is neutralized by a sodium hydroxide solution, and the sulfonated product is hydrolyzed for 240min at 90 ℃ to obtain a fatty alcohol ether sodium sulfonate aqueous solution. The unreacted content of the product was 6.0% (based on 100% total solids) and the sodium sulfate content was 1.5% (based on 100% total solids).
And (4) performance testing: 1.0% of the fatty alcohol ether sulfonate was clarified in 200g/L NaCl solution in 10g/L CaCl 2 The solution is clear. The product was heated at 150 ℃ for 72h without decomposition. The prepared fatty alcohol ether sulfonate and dodecyl betaine are compounded according to the proportion of 7/3 (mass ratio, total mass concentration is 0.2 percent), the interfacial tension between the fatty alcohol ether sulfonate and the dodecyl betaine and kerosene is 0.05 mN/m, and the interfacial tension test conditions are as follows: the temperature is 50 ℃, and deionized water is used for preparing a surfactant solution.
Example 4:
allyl-terminated polyoxyethylene n-decanol ether (n = 10) with SO obtained by the combustion sulphur method 3 Dry air reaction of mixed gases, SO 3 Volume ratio of air/3.5%, SO 3 The mol ratio of the allyl end capping n-decyl alcohol polyoxyethylene ether is 1.10:1, the temperature of the circulating water of a sulfonator jacket is 50 ℃, a sulfonated product is neutralized by a sodium hydroxide solution, and the sulfonated product is hydrolyzed for 60min at 130 ℃ to obtain a fatty alcohol ether sodium sulfonate aqueous solution. The unreacted content of the product was 7.5% (based on 100% total solids) and the sodium sulfate content was 1.4% (based on 100% total solids).
And (4) performance testing: 0.5% of the fatty alcohol ether sulfonate is clarified in 200g/L NaCl solution and in 10g/L CaCl 2 The solution is clear. The product was heated at 150 ℃ for 72h without decomposition. The prepared fatty alcohol ether sulfonate and the dioctyl dimethyl ammonium chloride are compounded in a mass ratio of 6/4 (the total mass concentration is 0.2 percent), and the interfacial tension between the fatty alcohol ether sulfonate and the kerosene can reach ultra low<0.01 mN/m), interfacial tension test conditions: the temperature is 50 ℃, and 100g/L NaCl solution is used for preparing the surfactant solution.
Example 5:
allyl-terminated isomeric tridecanol polyoxy-alcoholVinyl ether (n = 6) and SO obtained by a sulfur combustion process 3 Dry air reaction of mixed gases, SO 3 Volume ratio of/air 4.0%, SO 3 The mole ratio of the allyl-terminated isomeric tridecanol polyoxyethylene ether is 1.05:1, the temperature of the circulating water of the sulfonator jacket is 50 ℃, the sulfonated product is neutralized by sodium hydroxide solution, and the hydrolysis is carried out for 100min at 120 ℃, thus obtaining the sodium fatty alcohol ether sulfonate aqueous solution. The unreacted content of the product was 5.5% (based on 100% total solids) and the sodium sulfate content was 0.7% (based on 100% total solids).
And (4) performance testing: 0.5% of the fatty alcohol ether sulfonate is clarified in 200g/L NaCl solution in 10g/L CaCl 2 The solution is clear. The product was heated at 150 ℃ for 72h without decomposition. The prepared fatty alcohol ether sulfonate/hexadecyl betaine/lauryl polyoxyethylene ether (EO = 9) is compounded in a mass ratio of 4/2/4 (the total mass concentration is 0.2 percent), and then the interfacial tension between the fatty alcohol ether sulfonate/hexadecyl betaine/lauryl polyoxyethylene ether and kerosene can reach ultralow<0.01 mN/m), interfacial tension test conditions: the temperature is 50 ℃, and a surfactant solution is prepared from 50g/L NaCl solution.
Example 6:
allyl-terminated n-octanol polyoxyethylene ether (n = 5) with SO obtained by the combustion sulfur process 3 Dry air reaction of mixed gases, SO 3 Volume ratio of/air 3.0%, SO 3 The mol ratio of the allyl end capping n-octyl alcohol polyoxyethylene ether is 1.08:1, the temperature of the circulating water of the sulfonator jacket is 30 ℃, the sulfonated product is neutralized by potassium hydroxide solution, and the product is hydrolyzed for 180min at 90 ℃ to obtain the potassium alcohol ether sulfonate aqueous solution. The unreacted content of the product was 4.0% (based on 100% total solids) and the sodium sulfate content was 0.8% (based on 100% total solids).
And (3) performance testing: 0.5% of the fatty alcohol ether sulfonate is clarified in 200g/L NaCl solution and in 10g/L CaCl 2 The solution is clear. The fatty alcohol ether sulfonate and sodium dodecyl benzene sulfonate complex system is clarified in 100g/L NaCl solution according to a mass ratio of 4/6, so that the salt tolerance of the sodium dodecyl benzene sulfonate is improved, and the sodium dodecyl benzene sulfonate is turbid in 15g/L NaCl solution). The product was heated at 150 ℃ for 72h without decomposition.
Claims (9)
1. Allyl-terminated fatty alcohol-polyoxyethylene ether and SO 3 The process for preparing the fatty alcohol ether sulfonate by the reaction is characterized by comprising the following steps:
SO 3 the dry air mixed gas enters the top of a membrane type sulfonator after being filtered, simultaneously, the allyl-terminated fatty alcohol-polyoxyethylene ether also enters the top of the sulfonator, circulating water is introduced into a jacket of the sulfonator to remove reaction heat release, and a sulfonated product leaves from the bottom of the sulfonator to finish the sulfonation reaction; the sulfonation product is a mixture of sulfonic acid and sultone;
then neutralizing the sulfonated product with alkali solution, reacting sulfonic acid with alkali to generate corresponding sulfonate, and finally hydrolyzing, wherein sultone reacts with alkali to obtain fatty alcohol ether sulfonate.
2. The allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate by reaction is characterized by comprising the following steps: the allyl end-capped fatty alcohol-polyoxyethylene ether has the following structural formula:
wherein R is alkyl and the carbon chain is C 8 To C 18 One or any mixture of a plurality of the components; n =1 to 10.
3. The allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate by reaction is characterized by comprising the following steps: the resulting product fatty alcohol ether sulfonate is a mixture of:
wherein R is alkyl and the carbon chain is C 8 To C 18 One or a mixture of any of the above; m is an alkali metal, including sodium, potassium, lithiumTo one of (1).
4. The allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate through reaction is characterized by comprising the following steps: SO (SO) 3 In dry air mixture, SO 3 The volume ratio of the SO to the air is 2.5-4.0: 100 3 The mol ratio of the allyl-terminated fatty alcohol to the allyl-terminated fatty alcohol-polyoxyethylene ether is 1.00-1.10: 1.
5. the allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate through reaction is characterized by comprising the following steps: the temperature of the sulfonator jacket water is 20-70 ℃.
6. The allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate by reaction is characterized by comprising the following steps: the hydrolysis temperature is 90-150 ℃, and the hydrolysis time is 30-240 min.
7. The allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate by reaction is characterized by comprising the following steps: the SO 3 In dry air mixture, SO 3 Is prepared from sulfur by combustion or liquid SO 3 Prepared by an evaporation method.
8. The allyl-terminated fatty alcohol-polyoxyethylene ether and SO of claim 1 3 The process for preparing the fatty alcohol ether sulfonate by reaction is characterized by comprising the following steps: the alkali is one of sodium hydroxide, potassium hydroxide and lithium hydroxide.
9. The use of a fatty alcohol ether sulfonate prepared by the process of any one of claims 1 to 8 in oil field exploitation.
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