CN105481730A - Method for preparing rice-bran oleic monoethanol amide monosulfosuccinate - Google Patents
Method for preparing rice-bran oleic monoethanol amide monosulfosuccinate Download PDFInfo
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- CN105481730A CN105481730A CN201410517358.1A CN201410517358A CN105481730A CN 105481730 A CN105481730 A CN 105481730A CN 201410517358 A CN201410517358 A CN 201410517358A CN 105481730 A CN105481730 A CN 105481730A
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Abstract
The invention discloses a method for preparing rice-bran oleic monoethanol amide monosulfosuccinate. The method comprises the following processing steps: (A) carrying out an amidation reaction: adding rice-bran methyl oleate, monoethanolamine and DMF into a reactor, adding a composite catalyst into the reactor, introducing nitrogen into the reactor for protection, heating the reactor to the temperature of 100-150 DEG C, and carrying out a stirring reaction, so as to obtain rice-bran oleic monoethanol amide; (B) carrying out an esterification reaction: heating the rice-bran oleic monoethanol amide so as to melt the rice-bran oleic monoethanol amide, repeatedly adding ground maleic anhydride and a catalyst, maintaining a system at the constant temperature of 60-85 DEG C, heating the system to the temperature of 90 DEG C after feeding ends, and ending a reaction until the acid number of the system is not lowered any more; and (C) carrying out a sulfonation reaction: subjecting monoester to sulfonation with an aqueous solution of sodium sulfite immediately, and carrying out a reaction for 1-2 hours at the temperature of about 90 DEG C. According to the method disclosed by the invention, the operation is simple and convenient, the conversion ratio is high, and the cost is low; and the prepared product is aqueous, has excellent surface activation energy and is low in toxicity, easy in biodegradation and safe and environment-friendly in use.
Description
Technical field
The present invention relates to a kind of preparation method of oleic acid disodium ole amide monoethanolamine sulfosuccinate, belong to surfactant field.
Background technology
China first produces meter great Guo in the world, produces paddy 1.7 hundred million more than t and rice bran 8,500,000 more than t per year, rice bran oil-containing 16% ~ 25%.Although the domestic utilization to Rice pollard oil has 3O many kinds, and has developed 5O many kinds abroad, external all of certain scale in oil and fat chemical especially.And China utilizes not to the Rice pollard oil as regenerative raw materials, wide material sources, cheap readily biodegradable, resource is wasted.Utilize fatty acid methyl ester for raw material, the sulfosuccinate series of surfactants ROMS of synthesizing new.This series of surfactants is that recent domestic studies more new variety, has excellent surfactivity, and synthesis is easily, little to human body skin, eye irritation, and readily biodegradable, can be widely used in daily chemical products, be high-grade environment-friendly type tensio-active agent.Existing Oleum Cocois is the product of raw material at home, but due to lack of material, cost is higher, and output is restricted, non-widespread use.Rice pollard oil is cheap and easy to get, in order to synthesize ROMS, not only deepen the comprehensive utilization of Rice pollard oil, also can expand the raw material sources of sulfosuccinate series product, reduce costs, can scale operation and application, can be used as non-harmful liquid washing agent and replace other to the disadvantageous anion surfactant of environment.
Summary of the invention
Goal of the invention: the defect existed for prior art, the invention provides a kind of synthesis technique and simplifies easy to operate, the preparation method of the oleic acid disodium ole amide monoethanolamine sulfosuccinate that transformation efficiency is high.
For achieving the above object, a kind of preparation method of oleic acid disodium ole amide monoethanolamine sulfosuccinate, comprises following technological step:
A, amidate action: by oleic acid methyl esters, monoethanolamine and DMF add in reactor, add composite catalyst, logical nitrogen protection, is heated to 100 ~ 150 DEG C, stirring reaction 6 ~ 10h, recycling design, with acetone purified reaction product, obtains oleic acid single ethanol amide;
B, esterification: oleic acid single ethanol amide is added and carries out heat fused in the reactor, logical people's nitrogen protection, then maleic anhydride and the catalyzer of porphyrize is repeatedly added while stirring on a small quantity, maintenance system constant temperature 60 ~ 85 DEG C, after reinforced end, be warming up to 90 DEG C, termination reaction when reacting that acid number no longer reduces to system;
The monoesters that C, sulfonation reaction: step B generates carries out sulfonation with sodium sulfite aqueous solution immediately, and at about 90 DEG C reaction 1h ~ 2h, product is light yellow clear thick liquid oleic acid disodium ole amide monoethanolamine sulfosuccinate, and pH is 7.
In described steps A, the mol ratio of oleic acid methyl esters and monoethanolamine is 1:1.2.
In described steps A, composite catalyst is EDC (EDCI), 1-hydroxy benzo triazole (HOBt), the mixture of sodium ethylate.
In described step B, catalyzer is tosic acid.
In described step C, the mol ratio of monoesters and S-WAT is 1:1.2.
Described step C sulfite sodium is made into the aqueous solution that massfraction is 15% ~ 20%.
Method of the present invention is easy and simple to handle, and transformation efficiency is high, and cost is low;
Product prepared by the inventive method is water-based, and have excellent interfacial energy, toxicity is little, readily biodegradable, use safety environmental protection.
Specific embodiment
By the following examples the present invention is further explained:
Embodiment 1
A, amidate action: by 1mol oleic acid methyl esters, 1.05mol monoethanolamine and 500mlDMF add in reactor, add 4g composite catalyst: EDC (EDCI), 1-hydroxy benzo triazole (HOBt), the mixture of sodium ethylate, logical nitrogen protection, is heated to 110 DEG C, stirring reaction 8h, recycling design, with acetone purified reaction product, obtain oleic acid single ethanol amide, yield 95.7%;
B, esterification: made for steps A oleic acid single ethanol amide is added and carries out heat fused in the reactor, logical people's nitrogen protection, then 0.96mol maleic anhydride and the 1.6g tosic acid of porphyrize is repeatedly added while stirring on a small quantity, maintenance system constant temperature 60 ~ 85 DEG C, after reinforced end, be warming up to 90 DEG C, termination reaction when reacting that acid number no longer reduces to system;
The monoesters that C, sulfonation reaction: step B generates carries out sulfonation with sodium sulfite aqueous solution immediately, the mol ratio of monoesters and S-WAT is 1:1.05, S-WAT is made into the aqueous solution that massfraction is 15% ~ 20%, at about 90 DEG C reaction 1.5h, product is light yellow clear thick liquid oleic acid disodium ole amide monoethanolamine sulfosuccinate, and pH is 7.
Embodiment 2
A, amidate action: by 1mol oleic acid methyl esters, 1.1mol monoethanolamine and 500mlDMF add in reactor, add 4.2g composite catalyst: EDC (EDCI), 1-hydroxy benzo triazole (HOBt), the mixture of sodium ethylate, logical nitrogen protection, is heated to 110 DEG C, stirring reaction 8h, recycling design, with acetone purified reaction product, obtain oleic acid single ethanol amide, yield 96.1%;
B, esterification: made for steps A oleic acid single ethanol amide is added and carries out heat fused in the reactor, logical people's nitrogen protection, then 0.961mol maleic anhydride and the 1.6g tosic acid of porphyrize is repeatedly added while stirring on a small quantity, maintenance system constant temperature 60 ~ 85 DEG C, after reinforced end, be warming up to 90 DEG C, termination reaction when reacting that acid number no longer reduces to system;
The monoesters that C, sulfonation reaction: step B generates carries out sulfonation with sodium sulfite aqueous solution immediately, the mol ratio of monoesters and S-WAT is 1:1.05, S-WAT is made into the aqueous solution that massfraction is 15% ~ 20%, at about 90 DEG C reaction 1.5h, product is light yellow clear thick liquid oleic acid disodium ole amide monoethanolamine sulfosuccinate, and pH is 7.
Embodiment 3
A, amidate action: by 1mol oleic acid methyl esters, 1.15mol monoethanolamine and 500mlDMF add in reactor, add 4.4g composite catalyst: EDC (EDCI), 1-hydroxy benzo triazole (HOBt), the mixture of sodium ethylate, logical nitrogen protection, is heated to 110 DEG C, stirring reaction 6h, recycling design, with acetone purified reaction product, obtain oleic acid single ethanol amide, yield 96.7%;
B, esterification: made for steps A oleic acid single ethanol amide is added and carries out heat fused in the reactor, logical people's nitrogen protection, then 0.967mol maleic anhydride and the 1.6g tosic acid of porphyrize is repeatedly added while stirring on a small quantity, maintenance system constant temperature 60 ~ 85 DEG C, after reinforced end, be warming up to 90 DEG C, termination reaction when reacting that acid number no longer reduces to system;
The monoesters that C, sulfonation reaction: step B generates carries out sulfonation with sodium sulfite aqueous solution immediately, the mol ratio of monoesters and S-WAT is 1:1.05, S-WAT is made into the aqueous solution that massfraction is 15% ~ 20%, at about 90 DEG C reaction 1.5h, product is light yellow clear thick liquid oleic acid disodium ole amide monoethanolamine sulfosuccinate, and pH is 7.
Claims (6)
1. a preparation method for oleic acid disodium ole amide monoethanolamine sulfosuccinate, is characterized in that, comprises following processing step:
A, amidate action: by oleic acid methyl esters, monoethanolamine and DMF add in reactor, add composite catalyst, logical nitrogen protection, is heated to 100 ~ 150 DEG C, stirring reaction 6 ~ 10h, recycling design, with acetone purified reaction product, obtains oleic acid single ethanol amide;
B, esterification: oleic acid single ethanol amide is added and carries out heat fused in the reactor, logical people's nitrogen protection, then maleic anhydride and the catalyzer of porphyrize is repeatedly added while stirring on a small quantity, maintenance system constant temperature 60 ~ 85 DEG C, after reinforced end, be warming up to 90 DEG C, termination reaction when reacting that acid number no longer reduces to system;
The monoesters that C, sulfonation reaction: step B generates carries out sulfonation with sodium sulfite aqueous solution immediately, and at about 90 DEG C reaction 1h ~ 2h, product is light yellow clear thick liquid oleic acid disodium ole amide monoethanolamine sulfosuccinate, and pH is 7.
2. the preparation method of a kind of oleic acid disodium ole amide monoethanolamine sulfosuccinate as claimed in claim 1, is characterized in that the mol ratio of oleic acid methyl esters and monoethanolamine in steps A is 1:1.2.
3. the preparation method of a kind of oleic acid disodium ole amide monoethanolamine sulfosuccinate as claimed in claim 1, it is characterized in that in steps A, composite catalyst is EDC, 1-hydroxy benzo triazole, the mixture of sodium ethylate.
4. the preparation method of a kind of oleic acid disodium ole amide monoethanolamine sulfosuccinate as claimed in claim 1, is characterized in that in step B, catalyzer is tosic acid.
5. the preparation method of a kind of oleic acid disodium ole amide monoethanolamine sulfosuccinate as claimed in claim 1, is characterized in that the mol ratio of monoesters and S-WAT in step C is 1:1.2.
6. the preparation method of a kind of oleic acid disodium ole amide monoethanolamine sulfosuccinate as claimed in claim 1, is characterized in that step C sulfite sodium is made into the aqueous solution that massfraction is 15% ~ 20%.
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| CN201410517358.1A CN105481730A (en) | 2014-09-30 | 2014-09-30 | Method for preparing rice-bran oleic monoethanol amide monosulfosuccinate |
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| CN201410517358.1A CN105481730A (en) | 2014-09-30 | 2014-09-30 | Method for preparing rice-bran oleic monoethanol amide monosulfosuccinate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111378119A (en) * | 2020-03-25 | 2020-07-07 | 云浮循环经济工业园协同创新研究院 | Ethylene oxide derivative with branched chain and tetrasulfonic acid group structure, method and application |
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2014
- 2014-09-30 CN CN201410517358.1A patent/CN105481730A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111378119A (en) * | 2020-03-25 | 2020-07-07 | 云浮循环经济工业园协同创新研究院 | Ethylene oxide derivative with branched chain and tetrasulfonic acid group structure, method and application |
| CN111378119B (en) * | 2020-03-25 | 2023-03-10 | 云浮循环经济工业园协同创新研究院 | Ethylene oxide derivative with branched chain and tetrasulfonic acid group structure, method and application |
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