CN111807996A - Sulfonation method of fatty alcohol-polyoxyethylene ether - Google Patents
Sulfonation method of fatty alcohol-polyoxyethylene ether Download PDFInfo
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
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Abstract
The invention relates to a sulfonation method of fatty alcohol-polyoxyethylene ether, which mainly solves the problem of high content of dioxane in a sulfonation product in the prior art.
Description
Technical Field
The invention relates to a method for sulfonating fatty alcohol-polyoxyethylene ether.
Background
The molecular end of the fatty alcohol-polyoxyethylene ether has hydroxyl, and the hydroxyl can react with a sulfonating agent to convert the fatty alcohol-polyoxyethylene ether into fatty alcohol-polyoxyethylene ether sulfate in a sulfonation reactor. In order to increase the requirements of stability and the like of sulfonated products, the obtained fatty alcohol-polyoxyethylene ether sulfate can be further subjected to alkali neutralization and the like to obtain products with various specifications and requirements. The sulfonating agent is sulfur trioxide, and the sulfonation reactor may be any one or a combination of a stirred bubble reactor, a membrane reactor (wherein the membrane reactor may be either a rising film or a falling film), and a jet reactor, but is most commonly a membrane reactor, and more commonly a falling film reactor.
In the process of producing fatty alcohol polyoxyethylene ether sulfate by sulfonating fatty alcohol polyoxyethylene ether, generation of dioxane is caused for various reasons, and the dioxane is harmful impurity, and in order to reduce the content of the dioxane in production, vacuumizing and heating are adopted to remove the dioxane in the follow-up process so as to reduce the content of the dioxane, but the removal of the dioxane in a vacuum and heating mode can generate larger energy consumption.
In the prior art, CN106397276A reports that the mixture of fatty alcohol polyoxyethylene ether sulfate, fatty alcohol polyoxyethylene ether sulfate alkali metal salt or fatty alcohol polyoxyethylene ether ammonium sulfate and fatty alcohol polyoxyethylene ether is used as an organic material for sulfonation reaction, so as to reduce the chromaticity of a sulfonated product, thereby reducing the usage amount of subsequent decolorizing agent hydrogen peroxide, but does not relate to the technical problem of how to reduce the generation of dioxane in the sulfonation process.
Disclosure of Invention
The invention aims to solve the technical problem that the side reaction of generating the dioxane in the sulfonation process of the fatty alcohol polyoxyethylene ether in the prior art seriously causes the content of harmful impurity dioxane in the fatty alcohol sulfate, and provides a novel sulfonation method of the fatty alcohol polyoxyethylene ether.
In order to solve the technical problems, the technical scheme of the invention is as follows:
the sulfonation method of fatty alcohol-polyoxyethylene ether comprises the step of enabling an organic material and a sulfonating agent to react in a sulfonation reactor to obtain a sulfonated product, wherein the organic material comprises fatty alcohol-polyoxyethylene ether and an organic carbonyl compound, and the molecules of the carbonyl compound contain carboxylic ester bonds or carboxylic amide bonds.
The organic carbonyl compound is added into fatty alcohol polyoxyethylene ether to be used as an organic material for sulfonation reaction, and the content of the dioxane in the obtained sulfonated product is obviously lower than that in the sulfonated product which is not added with the organic carbonyl compound and only takes the fatty alcohol polyoxyethylene ether as the organic material.
In the above technical solution, preferably, the ratio of the organic carbonyl compound to the organic material is more than 0 and less than 0.1 by weight.
In the above embodiment, as non-limiting examples of the ratio of the organic carbonyl compound to the organic material, for example, but not limited to, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.015, 0.02, 0.025, 0.03, 0.035, 0.04, 0.045, 0.05, 0.055, 0.06, 0.065, 0.07, 0.075, 0.08, 0.085, 0.09, 0.095, etc. can be given.
In the above technical solution, when the ratio of the organic carbonyl compound to the organic material is greater than 0 and less than 0.009, the effect of reducing dioxane becomes more obvious as the addition amount of the organic carbonyl compound increases; however, from the viewpoint of obtaining a stable low level of dioxane and not excessively increasing the amount of the organic carbonyl compound added, the ratio of the organic carbonyl compound to the organic material is preferably 0.015 to 0.090.
In the above technical scheme, preferably, the fatty alcohol-polyoxyethylene ether is in accordance with the following structural formula I:
R1(OCH2CH2)nOH, structural formula I;
wherein R is1Is selected from C8-C18 aliphatic hydrocarbon groups, and n is more than 0 and less than 10.
In the above technical solutions, it is preferred that the carbonyl compound corresponds to the following structural formula II:
wherein R is2Is aliphatic hydrocarbon radical of C8-C20, R3Is methyl or H, R4Is H or a group of the formula III:
wherein R is5Is H or methyl.
In the above technical scheme, R1 and R2 are independently selected from linear hydrocarbon groups or hydrocarbon groups having a branched chain.
In the above schemes, R1 and R2 are independently primary or secondary hydrocarbyl groups, but primary hydrocarbyl groups are preferred.
In the above technical scheme, R2 is selected from saturated hydrocarbon group or unsaturated hydrocarbon group, preferably alkyl.
In the above technical scheme, as a non-limiting example, R1 and R2 are each independently a C8 hydrocarbon group, a C9 hydrocarbon group, a C10 hydrocarbon group, a C11 hydrocarbon group, a C12 hydrocarbon group, a C13 hydrocarbon group, a C14 hydrocarbon group, a C15 hydrocarbon group, a C16 hydrocarbon group, a C17 hydrocarbon group, a C18 hydrocarbon group, or the like.
R in the embodiments of the present invention is merely for comparison1Are all 1-dodecyl, R2Are each 1-undecyl, R3And R5Are all H.
In the above technical solution, n may be, for example, but not limited to, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, and the like, as non-limiting examples. For the sake of comparison, all of the embodiments of the present invention have n of 3.
In the above technical solution, the sulfonating agent may be at least one of fuming sulfuric acid, sulfur trioxide, chlorosulfonic acid and sulfamic acid, but preferably the sulfonating agent is sulfur trioxide.
In the above technical solution, preferably, the sulfur trioxide is used in a form diluted with a gaseous diluent.
In the above technical solution, preferably, the gaseous diluent is air or nitrogen.
In the above technical solution, it is preferable that sulfur trioxide accounts for 0.1 to 10% by weight of the total weight of sulfur trioxide and the gaseous diluent, and sulfur trioxide may account for 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, and so on by way of non-limiting example, of the total weight of sulfur trioxide and the gaseous diluent.
In the technical scheme, the molar ratio of the sulfonating agent to the organic material is preferably 1.01-1.03. In the present invention, the mole number of the organic material in the mole ratio of the sulfonating agent to the organic material is calculated by the mole number of the hydroxyl group contained therein.
In the above technical scheme, the sulfonation reactor is preferably a stirred bubbling reactor, a membrane reactor or a jet reactor. More preferably a membrane reactor, most preferably a falling film reactor in a membrane reactor.
In order to achieve comparable technical effects, the specific embodiment of the invention adopts a multi-tube falling film reactor manufactured by Ballestra, Italy, wherein each reaction tube is 6 meters high, the inner diameter of the reaction tube is 25.4mm, each reaction tube adopts upper and lower sections for cooling, and a tube for cooling SO is arranged above all the reaction tubes3And air, said organic material being fed using an annular gap.
Once the form and size of the reactor are determined, the skilled person can rationally select the feed rate of the organic material and achieve the technical effect of the invention of comparably reducing the amount of dioxane in the sulfonated product. For example, for the reactor employed in the embodiments of the present invention, the feed rate of the organic material, expressed as the average feed rate per reaction tube, may be, but is not limited to, 10 to 60 kg/hour, as non-limiting examples of feed rate point values, such as, but not limited to, 10 kg/hour, 20 kg/hour, 30 kg/hour, 40 kg/hour, 50 kg/hour, 60 kg/hour, and the like. In order to achieve comparable results in the examples and comparative examples, the feed rate of the organic material described in the examples or of the fatty alcohol polyoxyethylene ether in the comparative examples was 30 kg/h.
In the above technical scheme, the reaction temperature is preferably 40-50 ℃, for example, but not limited to 41 ℃, 42 ℃, 43 ℃, 44 ℃, 45 ℃, 46 ℃, 47 ℃, 48 ℃, 49 ℃ and the like.
It is known to those skilled in the art that the main component of the sulfonated product obtained from the reactor is fatty alcohol polyoxyethylene ether sulfate, which is easily hydrolyzed due to its high acidity, and in order to reduce the tendency of hydrolysis and to increase the storage stability, it is usually necessary to neutralize with a base, for example, with an aqueous solution of sodium hydroxide, to produce a sulfonated product based on sodium fatty alcohol polyoxyethylene ether sulfate, and the like. The invention may therefore also include subsequent steps as are well known in the art. For example, the method of the present invention comprises a step of neutralizing fatty alcohol-polyoxyethylene ether sulfate with an aqueous solution of sodium hydroxide to obtain sodium fatty alcohol-polyoxyethylene ether sulfate after sulfonation in a sulfonator.
In the specific embodiment of the invention, the sulfonated product of sodium sulfate salt obtained by neutralizing with sodium hydroxide aqueous solution is used as the analysis sample for testing. The method for measuring the content of the dioxane in the analysis sample is carried out according to a standard addition method specified in 7.2.1 in GB/T26388-2011 gas chromatography for measuring the residual amount of the dioxane in the surfactant.
The invention is further illustrated by the following specific embodiments:
Detailed Description
[ example 1 ]
Step 1, obtaining organic materials
And uniformly mixing the lauric acid monoethanolamide and the lauryl polyoxyethylene (3) ether according to the weight ratio of the lauric acid monoethanolamide to the lauryl polyoxyethylene (3) ether of 0.005 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). It was determined that the sulfonated product obtained in step 3 contained 23 mg dioxane per kg.
For comparison, the main process conditions and test results are listed in table 1.
[ example 2 ]
The main difference from the example 1 is that lauric acid diethanolamide is used to replace lauric acid monoethanolamide, which is specifically as follows:
step 1, obtaining organic materials
And (3) uniformly mixing the dodecanoic acid diethanolamide and the dodecanol polyoxyethylene (3) ether according to the weight ratio of the dodecanoic acid diethanolamide to the dodecanol polyoxyethylene (3) ether of 0.005 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). It was determined that the sulfonated product obtained in step 3 contained 31 mg dioxane per kg.
For comparison, the main process conditions and test results are listed in table 1.
[ example 3 ]
Step 1, obtaining organic materials
And uniformly mixing the lauric acid monoethanolamide and the lauryl polyoxyethylene (3) ether according to the weight ratio of the lauric acid monoethanolamide to the lauryl polyoxyethylene (3) ether of 0.002 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). The amount of dioxane was measured to be 38 mg per kg of the sulfonated product obtained in step 3.
For comparison, the main process conditions and test results are listed in table 1.
[ example 4 ]
Step 1, obtaining organic materials
And uniformly mixing the lauric acid monoethanolamide and the lauryl polyoxyethylene (3) ether according to the weight ratio of the lauric acid monoethanolamide to the lauryl polyoxyethylene (3) ether of 0.009 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). The amount of dioxane was measured to be 19 mg per kg of the sulfonated product obtained in step 3.
For comparison, the main process conditions and test results are listed in table 1.
[ example 5 ]
Step 1, obtaining organic materials
And uniformly mixing the lauric acid monoethanolamide and the lauryl polyoxyethylene (3) ether according to the weight ratio of the lauric acid monoethanolamide to the lauryl polyoxyethylene (3) ether of 0.015 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). The amount of dioxane was measured to be 16 mg per kg of the sulfonated product obtained in step 3.
For comparison, the main process conditions and test results are listed in table 1.
[ example 6 ]
Step 1, obtaining organic materials
And uniformly mixing the lauric acid monoethanolamide and the lauryl polyoxyethylene (3) ether according to the weight ratio of the lauric acid monoethanolamide to the lauryl polyoxyethylene (3) ether of 0.050 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). It was determined that the sulfonated product obtained in step 3 contained 17 mg dioxane per kg.
For comparison, the main process conditions and test results are listed in table 1.
[ example 7 ]
Step 1, obtaining organic materials
And uniformly mixing the lauric acid monoethanolamide and the lauryl polyoxyethylene (3) ether according to the weight ratio of the lauric acid monoethanolamide to the lauryl polyoxyethylene (3) ether of 0.090 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). The amount of dioxane was measured to be 16 mg per kg of the sulfonated product obtained in step 3.
For comparison, the main process conditions and test results are listed in table 1.
[ COMPARATIVE EXAMPLE 1 ]
The main difference from the example 1 is that the organic material does not contain organic carbonyl compounds, specifically:
step 1, obtaining organic materials
The lauryl polyoxyethylene (3) ether is used directly as the organic material for sulfonation as described in step 2 below.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The sulfonated product in the form of sulfonate is neutralized to pH 8 with 15% by weight aqueous sodium hydroxide solution to give a sulfonated product in the form of sodium salt, which is stabilized at 55 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). It was determined that 67 mg dioxane was present per kg sulfonated product from step 3.
For comparison, the main process conditions and test results are listed in table 1.
[ COMPARATIVE EXAMPLE 2 ]
The difference from the example 1 is that n-dodecyl polyoxyethylene (3) ether ammonium sulfate is used for replacing dodecanoic acid monoethanolamide, and specifically:
step 1, obtaining organic materials
And uniformly mixing the ammonium n-dodecyl polyoxyethylene (3) ether sulfate and the lauryl polyoxyethylene (3) ether according to the weight ratio of the ammonium n-dodecyl polyoxyethylene (3) ether sulfate to the lauryl polyoxyethylene (3) ether of 0.005 to obtain the organic material.
Step 2, sulfonation in a sulfonation reactor
Introducing the organic material and sulfur trioxide dry air mixed gas with the sulfur trioxide content of 4% from the top of a sulfonation reactor, wherein the feeding speed of the organic material is 30 kg/h, the feeding molar ratio of sulfur trioxide to the organic material is 1.03, and the temperature of the sulfonation reaction is 45 ℃. After the sulfonation reaction is finished, the sulfonated product is obtained in the form of sulfonate ester, and then:
step 3, neutralization of sulfonate ester
The above sulfonated product in the form of sulfonate was neutralized with an aqueous solution of sodium hydroxide having a weight concentration of 15% to pH 8 to obtain a sulfonated product in the form of sodium salt at a neutralization temperature of 56 ℃.
Step 4, analysis and characterization of sulfonated products
And (4) measuring the content of the dioxane in the sulfonated product obtained in the step (3). It was determined that the sulfonated product obtained in step 3 contained 63 mg dioxane per kg.
For comparison, the main process conditions and test results are listed in table 1.
TABLE 1
In addition: the main difference from example 1 is that the organic feed does not contain organic carbonyl compounds;
#: the difference from example 1 is that ammonium n-dodecylpolyoxyethylene3 ether sulfate is used instead of the dodecanoic acid monoethanolamide.
Claims (10)
1. The sulfonation method of fatty alcohol-polyoxyethylene ether comprises the step of enabling an organic material and a sulfonating agent to react in a sulfonation reactor to obtain a sulfonated product, wherein the organic material comprises fatty alcohol-polyoxyethylene ether and an organic carbonyl compound, and the molecules of the carbonyl compound contain carboxylic ester bonds or carboxylic amide bonds.
2. The sulfonation process of claim 1, wherein the fatty alcohol-polyoxyethylene ether has the following structural formula I:
R1(OCH2CH2)nOH, structural formula I;
wherein R is1Is selected from C8-C18 aliphatic hydrocarbon groups, and n is more than 0 and less than 10.
3. The sulfonation process of claim 1, characterized in that said carbonyl compound corresponds to the following formula II:
wherein R is2Is aliphatic hydrocarbon radical of C8-C20, R3Is methyl or H, R4Is H or a group of the formula III:
wherein R is5Is H or methyl.
4. The sulfonation process of claim 1, characterized in that said sulfonating agent is sulfur trioxide.
5. The sulfonation process of claim 4, characterized in that the sulfur trioxide is used in a form diluted with a gaseous diluent.
6. Sulfonation process according to claim 5, characterized in that the gaseous diluent is air or nitrogen.
7. The sulfonation process of claim 5, wherein sulfur trioxide is present in an amount of 0.1 to 10% by weight based on the total weight of sulfur trioxide and gaseous diluent.
8. The sulfonation process of claim 1, wherein the molar ratio of the sulfonating agent to the organic material is 1.01 to 1.03.
9. The sulfonation process of claim 1, wherein the sulfonation reactor is a stirred bubble reactor, a membrane reactor or a jet reactor.
10. The sulfonation method according to claim 1, wherein the reaction temperature is 40 to 50 ℃.
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