CN106117090B - The Asymmetric Gemini surfactants of sulfonic group containing carboxyl and its microwave preparation - Google Patents
The Asymmetric Gemini surfactants of sulfonic group containing carboxyl and its microwave preparation Download PDFInfo
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- CN106117090B CN106117090B CN201610429668.7A CN201610429668A CN106117090B CN 106117090 B CN106117090 B CN 106117090B CN 201610429668 A CN201610429668 A CN 201610429668A CN 106117090 B CN106117090 B CN 106117090B
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- acid diester
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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Abstract
The present invention relates to the Asymmetric Gemini surfactants of sulfonic group containing carboxyl and its microwave preparation.It is rarely reported with the research of microwave-hydrothermal method synthetic surfactant.Fatty monoethanol amide sulfosuccinic acid diester is made using fatty monoethanol amide maleic acid diester, lauryl sulfosuccinate acid esters disodium salt and sodium hydrogensulfite in the present invention, chloroacetic acid solution is added dropwise, it is transferred to high flux micro-wave digestion/extraction/synthetic work station reaction, neutralize, obtain one kind and contain carboxyl-sulfonic group Asymmetric Gemini surfactants.The present invention is raw material based on natural acid cheap and easy to get, the Asymmetric Gemini surfactants of sulfonic group containing carboxyl prepared using microwave method avoid raw material in conventional oil bath heating response time length, severe reaction conditions, reaction easily distil, raw material and the shortcomings of oxidation reaction easily occurs for product, product color is poor, there is good market applicability.
Description
Technical field
The present invention relates to a kind of surfactant, and in particular to one kind is lived containing carboxyl-sulfonic group dissymmetric Gemini surface
Property agent and its microwave preparation.
Background technology
With science and technology, industrial production and multidisciplinary cross-cutting continuous development, the application meeting of surfactant
It is increasingly wider, numerous aspects such as production and living can be associated with, as green chemical concept and people's environmental consciousness strengthen, surface is lived
Property agent is also imparted with higher performance requirement.Now, Gemini surface active is arisen at the historic moment, Gemini surface active due to
Its unique structure, good biological degradability, excellent surface-active turn into the research emphasis of related work person.Sulfonate type
Gemini surface active is a kind of very important anionic type Gemini surface active agent, and it has high surface, very
Water solubility well, wetability, dispersiveness, resistance to acids and bases are also greatly improved, so Sulfonic Gemini Surfactants
It will be applied in multiple fields.
Microwave is a kind of uhf electromagnetic wave of generally existing.Nowadays, microwave technology has been introduced by chemical field more than 40
Year, in recent years, in numerous synthetic methods, microwave-hydrothermal method is gradually shown one's talent.Compared with conventional method, microwave process for synthesizing
Have the advantages that heat utilization rate height, mild condition, firing rate be fast and uniform, non-thermal microwave effect.Therefore, microwave hydrothermal
Method has been to be concerned by more and more people.But use the research of microwave-hydrothermal method synthetic surfactant actually rare.
The content of the invention
Prepared it is an object of the invention to provide one kind containing carboxyl-sulfonic group Asymmetric Gemini surfactants and its microwave
Method.
The technical solution adopted in the present invention is：
Microwave preparation containing carboxyl-sulfonic group Asymmetric Gemini surfactants, it is characterised in that：
Realized by following steps：
Step 1：Prepare fatty monoethanol amide sulfosuccinic acid diester：
The fatty monoethanol amide maleic acid diester of 9.3-10.8 mass parts is weighed, adds in three-necked flask, uses quality
Its pH is neutralized to 7 by the sodium hydroxide solution that fraction is 40%, adds 3.1-4.3 mass parts lauryl sulfosuccinates acid esters two
Sodium salt；
The sodium hydrogensulfite of 2.2-2.4 mass parts is weighed, and is made into 30% solution of sodium bisulfite and is added drop-wise to three
In mouth flask, system is set to stir in 70-80 DEG C of water-bath；Reactant is transferred in microwave dissolver in temperature 140
DEG C -180 DEG C, reaction 40-90min obtains fatty monoethanol amide sulfosuccinic acid diester under conditions of power 600W；
Step 2：Preparation contains carboxyl-sulfonic group Asymmetric Gemini surfactants：
The monoxone of 3.4-4.2 mass parts is weighed, is made into 30% solution, and its solution is adjusted into pH to 7 with sodium hydroxide；
After chloroacetic acid solution is added dropwise into the fat acid single ethanol amide sulfosuccinic acid diester of 18.36-22.44 mass parts,
Regulation system pH to 7, stirs；
Reactant is transferred to high flux micro-wave digestion/extraction/70-90 DEG C, power 600w of synthetic work stand control temperature, instead
90-120min is answered, its pH is surveyed at interval of 20min and adjusts to 7, obtain one kind and contain carboxyl-sulfonic group dissymmetric Gemini surface
Activating agent.
In step 1, fatty monoethanol amide maleic acid diester is selected from lauric acid/dodecanoic acid single ethanol amide maleic acid diester, oil
Sour single ethanol amide maleic acid diester, stearic acid monoethanolamide maleic acid diester, rapeseed oil single ethanol amide maleic acid diester.
Live on surface made from microwave preparation as mentioned containing carboxyl-sulfonic group Asymmetric Gemini surfactants
Property agent.
The present invention has advantages below：
The present invention is using high flux micro-wave digestion/extraction/synthetic work station using microwave method in fatty monoethanol amide
On maleic acid diester, hydrophilic groups and sulfonic group are introduced, is made and contains carboxyl-sulfonic group Asymmetric Gemini surfactants
Intermediate, sulphonation rate can reach 85%, and tertiary-aminated yield is up to 80%.This method avoids the conventional oil bath heating response time
In length, severe reaction conditions, reaction raw material easily distil, raw material and the shortcomings of oxidation reaction easily occurs for product, product color is poor,
With good market applicability.
Embodiment
With reference to embodiment, the present invention will be described in detail.
The present invention utilizes microwave-hydrothermal method, using lauric acid/dodecanoic acid single ethanol amide and maleic mono-ester as raw material, is prepared into surface
Surfactant intermediate lauric acid/dodecanoic acid single ethanol amide maleic acid diester, and sulfonation, tertiary-aminated, introducing hydrophilic radical are carried out to dibasic acid esters,
It is prepared into and a kind of of good performance contains carboxyl-sulfonic group Asymmetric Gemini surfactants.
The present invention is using high flux micro-wave digestion/extraction/synthetic work station using microwave method in fatty monoethanol amide
On maleic acid diester, introduce hydrophilic groups and sulfonic group, its reaction equation are：
Specifically realized by following steps：
Step 1：Prepare fatty monoethanol amide sulfosuccinic acid diester：
The fatty monoethanol amide maleic acid diester of 9.3-10.8 mass parts is weighed, adds in three-necked flask, uses quality
Its pH is neutralized to 7 by the sodium hydroxide solution that fraction is 40%, adds 3.1-4.3 mass parts lauryl sulfosuccinates acid esters two
Sodium salt；
The sodium hydrogensulfite of 2.2-2.4 mass parts is weighed, and is made into 30% solution of sodium bisulfite and is added drop-wise to three
In mouth flask, system is set to stir in 70-80 DEG C of water-bath；Reactant is transferred in microwave dissolver in temperature 140
DEG C -180 DEG C, reaction 40-90min obtains fatty monoethanol amide sulfosuccinic acid diester under conditions of power 600W；
Step 2：Preparation contains carboxyl-sulfonic group Asymmetric Gemini surfactants：
The monoxone of 3.4-4.2 mass parts is weighed, is made into 30% solution, and its solution is adjusted into pH to 7 with sodium hydroxide；
After chloroacetic acid solution is added dropwise into the fat acid single ethanol amide sulfosuccinic acid diester of 18.36-22.44 mass parts,
Regulation system pH to 7, stirs；
Reactant is transferred to high flux micro-wave digestion/extraction/70-90 DEG C, power 600w of synthetic work stand control temperature, instead
90-120min is answered, its pH is surveyed at interval of 20min and adjusts to 7, obtain one kind and contain carboxyl-sulfonic group dissymmetric Gemini surface
Activating agent.
In step 1, fatty monoethanol amide maleic acid diester is selected from lauric acid/dodecanoic acid single ethanol amide maleic acid diester, oil
Sour single ethanol amide maleic acid diester, stearic acid monoethanolamide maleic acid diester, rapeseed oil single ethanol amide maleic acid diester.
Embodiment 1：
Step 1：The fatty monoethanol amide maleic acid diester of 9.8 mass parts is weighed, with 40% sodium hydroxide solution
Its pH is neutralized to 7, adds 3.3 mass parts lauryl sulfosuccinate acid esters disodium salts.Weigh the bisulfite of 2.2 mass parts
Sodium, and be made into 30% solution of sodium bisulfite and be added drop-wise in three-necked flask, make system in 70-80 DEG C of water-bath
Stir.Reactant is transferred in microwave dissolver the reaction 90min under conditions of 170 DEG C of temperature, power 600W and obtains fat
Fat acid single ethanol amide sulfosuccinic acid diester.
Step 2：Weigh the monoxone of 3.7 mass parts, be made into 30% solution, and by its solution with sodium hydroxide adjust pH to
7.Body is adjusted after above-mentioned 30% chloroacetic acid solution to be added dropwise to the fat acid single ethanol amide sulfosuccinic acid diester of 20.44 mass parts
It is pH to 7, stirs.Reactant is transferred to high flux micro-wave digestion/extraction/90 DEG C of synthetic work stand control temperature, power
600w, 120min is reacted, survey its pH at interval of 20min and adjust to 7, obtain one kind and contain carboxyl-sulfonic group dissymmetric Gemini
Surfactant.
In step 1, fatty monoethanol amide is lauric acid/dodecanoic acid single ethanol amide maleic acid diester.
Embodiment 2：
Step 1：The fatty monoethanol amide maleic acid diester of 10.8 mass parts is weighed, with 40% sodium hydroxide solution
Its pH is neutralized to 7, adds 4.3 mass parts lauryl sulfosuccinate acid esters disodium salts.Weigh the bisulfite of 2.4 mass parts
Sodium, and be made into 30% solution of sodium bisulfite and be added drop-wise in three-necked flask, stir system in 80 DEG C of water-bath
Uniformly.Reactant is transferred in microwave dissolver the reaction 60min under conditions of 180 DEG C of temperature, power 600W and obtains aliphatic acid
Single ethanol amide sulfosuccinic acid diester.
Step 2：Weigh the monoxone of 3.8 mass parts, be made into 30% solution, and by its solution with sodium hydroxide adjust pH to
7.Above-mentioned 30% chloroacetic acid solution is added dropwise to regulation system after the fat acid single ethanol amide sulfosuccinic acid diester of 19.6 mass parts
PH to 7, stirs.Reactant is transferred to high flux micro-wave digestion/extraction/85 DEG C of synthetic work stand control temperature, power
600w, 100min is reacted, survey its pH at interval of 20min and adjust to 7, obtain one kind and contain carboxyl-sulfonic group dissymmetric Gemini
Surfactant.
In step 1, fatty monoethanol amide is oleic monoethanolamide maleic acid diester.
Embodiment 3：
Step 1：The fatty monoethanol amide maleic acid diester of 9.3 mass parts is weighed, with 40% sodium hydroxide solution
Its pH is neutralized to 7, adds 3.3 mass parts lauryl sulfosuccinate acid esters disodium salts.Weigh the sulfurous acid of 2.25 mass parts
Hydrogen sodium, and be made into 30% solution of sodium bisulfite and be added drop-wise in three-necked flask, stir system in 75 DEG C of water-bath
Mix uniformly.Reactant is transferred in microwave dissolver the reaction 90min under conditions of 160 DEG C of temperature, power 600W and obtains fat
Sour single ethanol amide sulfosuccinic acid diester.
Step 2：Weigh the monoxone of 3.4 mass parts, be made into 30% solution, and by its solution with sodium hydroxide adjust pH to
7.Body is adjusted after above-mentioned 30% chloroacetic acid solution to be added dropwise to the fat acid single ethanol amide sulfosuccinic acid diester of 18.36 mass parts
It is pH to 7, stirs.Reactant is transferred to high flux micro-wave digestion/extraction/75 DEG C of synthetic work stand control temperature, power
600w, 90min is reacted, survey its pH at interval of 20min and adjust to 7, obtain one kind and contain carboxyl-sulfonic group dissymmetric Gemini
Surfactant.
In step 1, fatty monoethanol amide is that stearic acid monoethanolamide or rapeseed oil single ethanol amide maleic acid are double
Ester.
The structure detection result of fatty monoethanol amide maleic acid diester is as follows：
Infrared detections：3444.24 cm-1Place may be sample adsorption water-OH absworption peak；2925 cm-1、2854
cm-1For the antisymmetry and symmetrical stretching vibration absworption peak of methyl and methylene;1601cm-1For acid amides and carboxylate absorption peak；
1735 cm-1For the carbonyl absorption peak of ester；1400cm-1 The cm of carboxylate radical characteristic peak 1240-1、1174 cm-1For-C-O-C- not
The absworption peak of symmetrical stretching vibration；1116 cm-1With 1047 cm-1It is SO3Stretching vibration absworption peak.
Present disclosure is not limited to cited by embodiment, and those of ordinary skill in the art are by reading description of the invention
And any equivalent conversion taken technical solution of the present invention, it is that claim of the invention is covered.
Claims (1)
1. the microwave preparation containing carboxyl-sulfonic group Asymmetric Gemini surfactants, it is characterised in that：
Realized by following steps：
Step 1：Prepare fatty monoethanol amide sulfosuccinic acid diester：
The fatty monoethanol amide maleic acid diester of 9.3-10.8 mass parts is weighed, adds in three-necked flask, uses mass fraction
Its pH is neutralized to 7 for 40% sodium hydroxide solution, adds 3.1-4.3 mass parts lauryl sulfosuccinate acid esters disodium salts；
The sodium hydrogensulfite of 2.2-2.4 mass parts is weighed, and is made into 30% solution of sodium bisulfite and is added drop-wise to three mouthfuls of burnings
In bottle, system is set to stir in 70-80 DEG C of water-bath；By reactant be transferred in microwave dissolver 140 DEG C of temperature-
180 DEG C, reaction 40-90min obtains fatty monoethanol amide sulfosuccinic acid diester under conditions of power 600W；
Step 2：Preparation contains carboxyl-sulfonic group Asymmetric Gemini surfactants：
The monoxone of 3.4-4.2 mass parts is weighed, is made into 30% solution, and its solution is adjusted into pH to 7 with sodium hydroxide；
After chloroacetic acid solution is added dropwise into the fat acid single ethanol amide sulfosuccinic acid diester of 18.36-22.44 mass parts, regulation
System pH to 7, stirs；
Reactant is transferred to high flux micro-wave digestion/extraction/70-90 DEG C, power 600w of synthetic work stand control temperature, reacted
90-120min, survey its pH at interval of 20min and adjust to 7, obtain a kind of containing carboxyl-sulfonic group dissymmetric Gemini surface work
Property agent；
In step 1, fatty monoethanol amide maleic acid diester is selected from lauric acid/dodecanoic acid single ethanol amide maleic acid diester, oleic acid list
Glycollic amide maleic acid diester, stearic acid monoethanolamide maleic acid diester, rapeseed oil single ethanol amide maleic acid diester.
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