CN106588706A - Method for synthesizing methyl ricinoleate ethoxylate sulfonate - Google Patents
Method for synthesizing methyl ricinoleate ethoxylate sulfonate Download PDFInfo
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- CN106588706A CN106588706A CN201610996808.9A CN201610996808A CN106588706A CN 106588706 A CN106588706 A CN 106588706A CN 201610996808 A CN201610996808 A CN 201610996808A CN 106588706 A CN106588706 A CN 106588706A
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- Prior art keywords
- ethoxylate
- castor oil
- oil acid
- acid formicester
- sulfonates
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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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
The invention relates to a method for synthesizing methyl ricinoleate ethoxylate sulfonate. The method comprises the steps of adding methyl ricinoleate ethoxylate, sodium bisulfite, a catalyst, deionized water and low carbon alcohol into a reactor, carrying out a reaction with violent stirring, carrying out distilling at reduced pressure after the reaction ends so as to remove water and the low carbon alcohol, carrying out dissolving by using excessive anhydrous ethanol so as to remove unreacted sodium bisulfite and produced sodium sulfite, and carrying out distilling at reduced pressure to remove ethanol, thereby obtaining the product, wherein the mole ratio of methyl ricinoleate ethoxylate to sodium bisulfite is 1: (1.5 to 2.5), the use level of the catalyst is 1.5% to 2.5% the mass of methyl ricinoleate ethoxylate, and the mass ratio of the low carbon alcohol to the deionized water to methyl ricinoleate ethoxylate is (0.9 to 3): (0.9 to 3): 1. The method has the advantages that the synthesis process is simple and safe, and waste acids and waste alkalis cannot be generated.
Description
Technical field
The present invention relates to a kind of preparation method of anion surfactant, relates in particular to a kind of castor oil acid formicester
The synthetic method of ethoxylate sulfonates.
Background technology
In the last few years, as people are to environmental problem pay attention to day by day, develop new environmental protection Mobyneb surface and live
Property agent is increasingly subject to people's attention.Castor oil acid formicester ethoxylate is a kind of typical nonionic surfactant,
With low cost, be readily biodegradable, Environmental compatibility is good and little to skin irritation the features such as.Its molecular structure compares
It is special, compare with common Fatty acid methyl ester ethoxylate, on side chain many one similar to AEO
Structure, in addition intramolecular also have a carbon-carbon double bond, therefore suffer from the extensive concern of people.
Ethoxylates of Castor Oil sulfonate/Ethoxylates of Castor Oil sulfate is with castor oil acid
Formicester ethoxylate is raw material, with SO 3 sulfonated, then with alkali and obtaining.Because sulfonic group can be with ester appended
α hydrogen, it is also possible to replace the end hydrogen of side chain APEO, so sulfonate and sulfate can be generated.The castor-oil plant that reaction is obtained
Methyl oleate ethoxylate sulfonates/Ethoxylates of Castor Oil sulfate has low bubble property, emulsifying capacity is strong, go
Dirty power is strong, the advantages of easily rinse (Li Jie, Yang Xiaoyi, Sun Yongqiang, intelligence is vertical to fly. Ethoxylates of Castor Oil sulfonate/sulphur
The synthesis of hydrochlorate and physical and chemical performance [J]. printing and dyeing assistant, 2016,34 (4):7-10.).
With castor oil acid formicester ethoxylate as raw material, can with sodium hydrogensulfite Direct Sulfonation in the presence of catalyst
To obtain a kind of new anion surfactant ----castor oil acid formicester ethoxylate sulfonates, sodium hydrogensulfite adds
Into on intramolecular carbon-carbon double bond, the preparation method of this kind of surfactant at home and abroad has not been reported.
The content of the invention
The invention aims to provide a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates.
The molecular structural formula of the raw material castor oil acid formicester ethoxylate that the present invention is provided is as follows：
Wherein：X+y=15-20
It is as follows that the present invention is synthesized route：
The synthetic method of the anion surfactant castor oil acid formicester ethoxylate sulfonates that the present invention is provided, bag
Include following steps：
Castor oil acid formicester ethoxylate, sodium hydrogensulfite, catalyst, deionized water, low-carbon alcohols are added to into reaction
In device, under strong agitation, 60-80 DEG C is heated to, reacts 6-8h；Wherein castor oil acid formicester ethoxylate and sodium hydrogensulfite
Mol ratio be 1:1.5-2.5；The consumption of catalyst for castor oil acid formicester ethoxylation amount of substance 1.5-2.5%, low-carbon (LC)
The mass ratio of alcohol, deionized water and castor oil acid formicester ethoxylate is 0.9-3：0.9-3:1, after reaction terminates, decompression is steamed
Water and low-carbon alcohols are gone in distillation, and with excessive anhydrous alcohol solution, heat filtering removes unreacted sodium hydrogensulfite and the Asia for generating
Sodium sulphate, vacuum distillation removes ethanol and obtains product.
In above-mentioned reaction, the average adduct number of castor oil acid formicester ethoxylate ethylene oxide is 15-20, intramolecular
Containing undersaturated carbon-carbon double bond, because sodium hydrogensulfite addition is on intramolecular carbon-carbon double bond, so castor oil acid formicester second
Carbon-carbon double bond is not contained in epoxide compound sulfonate.
Catalyst in above-mentioned reaction is azodiisobutyronitrile.
Low-carbon alcohols in above-mentioned reaction are the alcohol of some short carbon chains such as methyl alcohol, ethanol, propyl alcohol, isopropanol or butanol.
The mol ratio of castor oil acid formicester ethoxylate and sodium hydrogensulfite is preferably 1 in above-mentioned reaction:1.8-2.2；
The consumption of catalyst is preferably the 1.9-2.3% of the quality of castor oil acid formicester ethoxylate, low-carbon alcohols, deionized water and castor
The mass ratio of sesame oil acid formicester ethoxylate is preferably 0.9-1.5：0.9-1.5:1.
Product in above-mentioned reaction is castor oil acid formicester ethoxylate sulfonates and castor oil acid formicester ethoxylation
The mixture of thing, is analyzed to product and may certify that and synthesized castor oil acid formicester ethoxylate sulfonates.By product point
From castor oil acid formicester ethoxylate sulfonates are obtained, castor oil acid formicester ethoxylate is recycled.
First sodium hydrogensulfite can be dissolved in deionized water in advance in above-mentioned reaction, then by castor oil acid formicester second
Epoxide compound, catalyst and low-carbon alcohols are added in ionized water, are so conducive to that what is reacted to be smoothed out.
It is an object of the invention to synthesize a kind of new anion surfactant castor oil acid formicester ethoxylate sulphur
Hydrochlorate, it is the anion surfactant that a kind of special anion-nonionic combines, and intramolecular has three hydrophilic group senses
Group, is obtained by sodium hydrogensulfite and the direct addition of castor oil acid formicester ethoxylate, and the position of addition is intramolecular
Carbon-carbon double bond.
The present invention has the advantage that compared with prior art：
1 has synthesized a kind of new sulfosalt surfactant, there is multiple hydrophilic functional groups, with low bubble property, easily rinse,
The advantages of alkali resistance is strong.
It is 2-in-1 into process is simple safety, and spent acid and salkali waste will not be produced.
Description of the drawings
Fig. 1 is the infrared spectrum after the castor oil acid formicester ethoxylate sulfonates purification of present invention synthesis
In Fig. 1,1178cm-1,1034cm-1,620cm-1And 519cm-1The absworption peak at place represents that intramolecular has sulfonic group sense
Group, 717cm-1Absworption peak be carbon-carbon double bond absworption peak because also have residual castor oil acid formicester ethoxylate do not have
Remove.
Specific embodiment
Present invention employs following method of testing：(1) determined by infrared spectrum and contain in product sulfonate functional groups.
(2) anionic surfactant concentration is determined using diphasic titration.(3) determine product iodine number, and with castor oil acid formicester
Ethoxylate iodine number is contrasted, and determines sodium hydrogensulfite addition on intramolecular carbon-carbon double bond by the way that calculating is final.
Embodiment 1
By 50g (0.051mol) castor oil acid formicester ethoxylate, (mean molecule quantity 976, X mean values are flat for 10.9, Y
Average is 4.2, and iodine number is 26.1g/100g), 100g deionized waters, 100g isopropanols, 8g (0.077mol) sodium hydrogensulfites with
And 1.1g azodiisobutyronitriles are added in the four-hole boiling flask of 500ml, 80 DEG C are heated to, react 6.5h.After reaction terminates, rotation
Evaporate and remove water and isopropanol, with excessive anhydrous alcohol solution, heat filtering removes unreacted sodium hydrogensulfite with generation
Sodium sulfite, rotary evaporation removes ethanol and obtains product.Product leading indicator is as follows：(1) iodine number is 22.1g/100g；(2) castor
The mass fraction of sesame oil acid formicester ethoxylate sodium sulfonate is 14.7%.
Embodiment 2
By 30g (0.030mol) castor oil acid formicester ethoxylate, (mean molecule quantity 976, X mean values are flat for 10.9, Y
Average is 4.2, and iodine number is 26.1g/100g), 60g deionized waters, 60g ethanol, 4.8g (0.046mol) sodium hydrogensulfites and
0.6g azodiisobutyronitriles are added in the four-hole boiling flask of 250ml and (sodium hydrogensulfite are dissolved in advance deionized water before charging
In), 78 DEG C are heated to, react 6h.After reaction terminates, rotary evaporation removes water and ethanol, with excessive anhydrous alcohol solution, heat
Unreacted sodium hydrogensulfite and the sodium sulfite for generating are filtered to remove, rotary evaporation removes ethanol and obtains product.Product is main
Index is as follows：(1) iodine number is 21.6g/100g；(2) mass fraction of castor oil acid formicester ethoxylate sodium sulfonate is
17.9%.
Embodiment 3
By 30g (0.026mol) castor oil acid formicester ethoxylate, (mean molecule quantity 1151, X mean values are 13.2, Y
Mean value is 5.9, and iodine number is 22.5g/100g), 55g deionized waters, 55g methyl alcohol, 5.4g (0.052mol) sodium hydrogensulfites with
And 0.5g azodiisobutyronitriles are added in the four-hole boiling flask of 250ml, 60 DEG C are heated to, react 8h.After reaction terminates, rotation is steamed
Send out and remove water and methyl alcohol, with excessive anhydrous alcohol solution, heat filtering removes unreacted sodium hydrogensulfite and the sulfurous for generating
Sour sodium, rotary evaporation removes ethanol and obtains product.Product leading indicator is as follows：(1) iodine number is 18.5g/100g；(2) castor oil
The mass fraction of sour formicester ethoxylate sodium sulfonate is 18.9%.
Embodiment 4
By 30g (0.026mol) castor oil acid formicester ethoxylate, (mean molecule quantity 1151, X mean values are 13.2, Y
Mean value is 5.9, and iodine number is 22.5g/100g), 80g deionized waters, 80g isopropanols, 6.5g (0.064mol) sodium hydrogensulfite
And 0.4g azodiisobutyronitriles be added in the four-hole boiling flask of 500ml (charging before sodium hydrogensulfite be dissolved in advance from
In sub- water), 78 DEG C are heated to, react 6h.After reaction terminates, rotary evaporation removes water and isopropanol, with excessive absolute ethyl alcohol
Dissolving, heat filtering removes unreacted sodium hydrogensulfite and the sodium sulfite for generating, and rotary evaporation removes ethanol and obtains product.Produce
Thing leading indicator is as follows：(1) iodine number is 17.6g/100g；(2) mass fraction of castor oil acid formicester ethoxylate sodium sulfonate
For 20.4%.
Embodiment 5
By 30g (0.029mol) castor oil acid formicester ethoxylate, (mean molecule quantity 1037, X mean values are 11.9, Y
Mean value is 4.5, and iodine number is 25g/100g), 70g deionized waters, 70g ethanol, 6g (0.058mol) sodium hydrogensulfites and
0.7g azodiisobutyronitriles are added in the four-hole boiling flask of 500ml, are heated to 75 DEG C, react 6.5h.After reaction terminates, rotation is steamed
Send out and remove water and ethanol, with excessive anhydrous alcohol solution, heat filtering removes unreacted sodium hydrogensulfite and the sulfurous for generating
Sour sodium, rotary evaporation removes ethanol and obtains product.Product leading indicator is as follows：(1) iodine number is 18.4g/100g；(2) castor oil
The mass fraction of sour formicester ethoxylate sodium sulfonate is 24.2%.
Embodiment 6
By 30g (0.029mol) castor oil acid formicester ethoxylate, (mean molecule quantity 1037, X mean values are 11.9, Y
Mean value is 4.5, and iodine number is 25g/100g), 90g deionized waters, 90g isopropanols, 6g (0.058mol) sodium hydrogensulfites and
0.7g azodiisobutyronitriles are added in the four-hole boiling flask of 500ml, are heated to 80 DEG C, react 6.5h.After reaction terminates, rotation is steamed
Send out and remove water and isopropanol, with excessive anhydrous alcohol solution, heat filtering removes unreacted sodium hydrogensulfite and the Asia for generating
Sodium sulphate, rotary evaporation removes ethanol and obtains product.Product leading indicator is as follows：(1) iodine number is 18.8g/100g；(2) castor-oil plant
The mass fraction of oleic acid formicester ethoxylate sodium sulfonate is 23.1%.
Embodiment 7
By 30g (0.029mol) castor oil acid formicester ethoxylate, (mean molecule quantity 1037, X mean values are 11.9, Y
Mean value is 4.5, and iodine number is 24.6g/100g), 30g deionized waters, 30g ethanol, 6g (0.058mol) sodium hydrogensulfites and
0.7g azodiisobutyronitriles are added in the four-hole boiling flask of 250ml, are heated to 78 DEG C and (sodium hydrogensulfite are dissolved in advance before charging
In deionized water), 7h is reacted.After reaction terminates, rotary evaporation removes water and ethanol, with excessive anhydrous alcohol solution, heat
Unreacted sodium hydrogensulfite and the sodium sulfite for generating are filtered to remove, rotary evaporation removes ethanol and obtains product.Product is main
Index is as follows：(1) iodine number is 18.2g/100g；(2) mass fraction of castor oil acid formicester ethoxylate sodium sulfonate is
25.2%.
Claims (7)
1. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates, it is characterised in that comprise the steps：
Castor oil acid formicester ethoxylate, sodium hydrogensulfite, catalyst, deionized water, low-carbon alcohols are added in reactor,
Under strong agitation, 60-80 DEG C is heated to, reacts 6-8h；Wherein castor oil acid formicester ethoxylate and sodium hydrogensulfite rubs
You are than being 1:1.5-2.5；The consumption of catalyst is the 1.5-2.5% of castor oil acid formicester ethoxylation amount of substance, and low-carbon alcohols are gone
The mass ratio of ionized water and castor oil acid formicester ethoxylate is 0.9-3：0.9-3:1, after reaction terminates, vacuum distillation is removed
Water and low-carbon alcohols, with excessive anhydrous alcohol solution, heat filtering removes unreacted sodium hydrogensulfite and the sodium sulfite for generating,
Vacuum distillation removes ethanol and obtains product.
2. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates as claimed in claim 1, it is characterised in that
The molecular structural formula of raw material castor oil acid formicester ethoxylate is as follows：
Wherein：X+y=15-20.
3. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates as claimed in claim 1, it is characterised in that
Catalyst is azodiisobutyronitrile.
4. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates as claimed in claim 1, it is characterised in that
Low-carbon alcohols are methyl alcohol, ethanol, propyl alcohol, isopropanol or butanol.
5. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates as claimed in claim 1, it is characterised in that
The mol ratio of castor oil acid formicester ethoxylate and sodium hydrogensulfite is preferably 1:1.8-2.2；The consumption of catalyst is preferably
The 1.9-2.3% of the quality of castor oil acid formicester ethoxylate, low-carbon alcohols, deionized water and castor oil acid formicester ethoxylation
The mass ratio of thing is preferably 0.9-1.5：0.9-1.5:1.
6. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates as claimed in claim 1, it is characterised in that
First sodium hydrogensulfite dissolved in deionized water in advance, then by castor oil acid formicester ethoxylate, catalyst and low-carbon alcohols
In adding ionized water.
7. a kind of synthetic method of castor oil acid formicester ethoxylate sulfonates as claimed in claim 1, it is characterised in that
Product is the mixture of castor oil acid formicester ethoxylate sulfonates and castor oil acid formicester ethoxylate, and product is separated
Castor oil acid formicester ethoxylate sulfonates are obtained, castor oil acid formicester ethoxylate is recycled.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484450A (en) * | 2018-03-29 | 2018-09-04 | 中国日用化学研究院有限公司 | The synthetic method of oleic acid disodium salt |
| CN116041229A (en) * | 2023-02-21 | 2023-05-02 | 太原理工大学 | Castor oil-based sulfonate anionic surfactant and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484450A (en) * | 2018-03-29 | 2018-09-04 | 中国日用化学研究院有限公司 | The synthetic method of oleic acid disodium salt |
| CN116041229A (en) * | 2023-02-21 | 2023-05-02 | 太原理工大学 | Castor oil-based sulfonate anionic surfactant and preparation method thereof |
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