CN106946840B - Two glycerol monoacetals of one kind and its preparation method and application - Google Patents
Two glycerol monoacetals of one kind and its preparation method and application Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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Abstract
The invention discloses a kind of two glycerol monoacetals and its preparation method and application.The two glycerol monoacetal, uses lewis acid for catalyst, does not use any solvent, two glycerol of catalysis and carbon atom number as 4 ~ 16 representative examples of saturated aliphatic aldehyde generation acetalation and prepares two glycerol monoacetals；The molar ratio of the representative examples of saturated aliphatic aldehyde and two glycerol is 1:(0.2 ~ 5).Two glycerol monoacetal of gained has good surface-active property: the ability for reducing aqueous solution surface tension is strong, and foaming abundancy, emulsifying effectiveness is good, alkaline-resisting, stability in hard water is good.
Description
Technical field
The present invention relates to a kind of two glycerol monoacetals and its preparation method and application, belong to technical field of fine.
Background technique
Biodiesel is effective complementarity energy under existing energy frame.With the extensive use of biodiesel, by-product
The utilization of object glycerol becomes urgent problem.Because the methanol being added in production process makes the glycerol benefit of this part
With being restricted, so being converted into the chemicals of high added value by the methods of oxidation, hydrogenation, etherificate, esterification, condensation.
Two glycerol are the polyol ethers of hydroxyl containing there are four that two molecule glycerol are obtained by itself etherificate, are the low of glycerol
One of poly- product.Due to the presence of polyhydroxy so that its cosmetics, food emulsifying agent and in terms of
There is application.
Two glycerol and aldehydes or ketones can also occur acetalation or ketal reaction synthesizing new, there is potential using value
Substance.For two glycerol tool there are four hydroxyl, the carrying out with two hydroxyls of the aldehydes or ketones property of can choose react generation cyclic acetal, and
Retain other two hydroxyl, generates the product of two glycerol monoacetals.
Two glycerol of acidic catalyst Catalyzed by p-Toluenesulfonic Acid and carbonyls (aldehyde are described in patent WO 9412489A1
Or ketone) acetalation or two glycerol monoacetal of ketal reaction synthetic product or two glycerol single ketals occur under DMF solvent, and will
Product is applied to the property in detergent and detergent compounding.Two glycerol monoacetals of above-mentioned reaction or two glycerol single ketals
Selectivity is low, and organic acid is added as catalyst and organic solvent, reacts not easy to operate, unfriendly to environment.
Two glycerol and aldehyde pass through acetalation and easily form two glycerol, two acetal, and two glycerol, two acetal is that four hydroxyls are complete
The product of portion's acetalation, reduces the hydrophilic nmature of molecule, to limit its application on surfactant.
Summary of the invention
The present invention is intended to provide a kind of two glycerol monoacetals and preparation method thereof, two glycerol and carbon atom number are 4~16
The two glycerol monoacetals that representative examples of saturated aliphatic aldehyde is synthesized by acetalation have potential application value as surfactant.
The present invention provides a kind of two glycerol monoacetals, different with dividing for four kinds shown in following (I), (II), (III), (IV)
The mixture of structure body:
Wherein R is C3~C15Straight chained alkyl.
Above-mentioned two glycerol monoacetal, wherein the R is preferably C5~C11Straight chained alkyl.
The present invention provides a kind of preparation methods of the described in any item two glycerol monoacetals of claims 1 or 2, using road
Lewis acid is catalyst, does not use any solvent, and the representative examples of saturated aliphatic aldehyde that two glycerol of catalysis are 4~16 with carbon atom number contracts
Aldehyde reaction prepares two glycerol monoacetals；The molar ratio of the representative examples of saturated aliphatic aldehyde and two glycerol is 1:(0.2~5), preferably
Molar ratio is 1:(0.2~2).
Above-mentioned preparation method the following steps are included:
(1) representative examples of saturated aliphatic aldehyde is mixed with two glycerol, using aldehyde as benchmark object, lewis acid is added as catalyst, stirs
It mixes and is warming up to 50~220 DEG C, react 1~12 hour；
(2) after reaction, two glycerol are chromatographed to obtain through washing, extraction, washing removing catalyst, drying, vacuum concentration, column
Monoacetal product.
In above-mentioned preparation method, the mass ratio of the aldehyde and lewis acid catalyst is 1:(0.002~1).
In above-mentioned preparation method, the lewis acid catalyst is zinc chloride, barium chloride, magnesium chloride, calcium chloride, chlorination
One of iron, aluminium chloride, copper chloride or frerrous chloride.
In above-mentioned preparation method, in the step (2), after reaction, adopts and be washed with distilled water, ethyl acetate extraction,
Saturated sodium carbonate solution washing removes catalyst, dry using anhydrous sodium sulfate, uses petroleum ether and ethyl alcohol volume ratio (10-
30): 1 column chromatographs to obtain two glycerol monoacetals.
In above-mentioned preparation method, the acetalation equation are as follows:
Wherein R is C3~C15Straight chained alkyl.
Reaction principle: representative examples of saturated aliphatic aldehyde and two glycerine reactions, under the action of lewis acid, metal ion can be selected
Property have an effect with hydroxyl, to generate reaction intermediate, occupy the hydroxy position of a part, the hydroxyl of exposure another part
Base, thus the aldehyde property of can choose react with two glycerol, generate two glycerol monoacetals.
The present invention provides application of the above-mentioned two glycerol monoacetal in surfactant.
Beneficial effects of the present invention:
The present invention be under solvent-free system by two glycerol of Lewis acid catalyst and carbon atom number be 4~16 it is full
Two glycerol monoacetals are prepared by acetalation with aliphatic aldehyde, the ability that product reduces aqueous solution surface tension is strong, foam
Abundant, emulsifying effectiveness is good, alkaline-resisting, stability in hard water is good.
Detailed description of the invention
Fig. 1 is the FT-IR infrared spectroscopy for the two glycerol monoacetals that embodiment 1 is prepared.
Fig. 2 is the aqueous solution surface tension curve for the two glycerol monoacetals that embodiment 3 is prepared.
Specific embodiment
The present invention is further illustrated below by embodiment, but is not limited to following embodiment.
Embodiment 1:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press n-octaldehyde afterwards: n-octaldehyde 4.92g is added in two glycerol=1:1.3 (molar ratio, similarly hereinafter), according to n-octaldehyde: zinc chloride=1:
Zinc chloride catalyst 0.20g is added in 0.04 (mass ratio, similarly hereinafter), and under nitrogen atmosphere, stirring is warming up to 100 DEG C, reacts 4 hours
After be cooled to room temperature, gained reaction solution through water washing, ethyl acetate extraction, saturated sodium carbonate solution washing remove catalyst, nothing
Aqueous sodium persulfate is dry, is concentrated in vacuo, and obtains two glycerol acetonide lists after being chromatographed with petroleum ether and ethyl alcohol (volume ratio 20:1, similarly hereinafter) column
Octanal, yield 81.2%.
Infrared spectrum characterization is carried out to product, the infrared spectroscopy of product is as shown in Figure 1.In 3441cm-1It is the spy of free OH
Levy absorption peak, 2924cm-1、22853cm-1、1456cm-1、1418cm-1It is CH3、CH2Stretching vibration peak, 11123cm-1With
1045cm-1For the characteristic peak of C-O-C structure, 724cm-1It is CH in long-chain methylene2Stretching vibration peak, 812cm-1It is hexa-atomic
The characteristic peak of cyclic ketal, 951cm-1It is the characteristic peak of five-membered ring acetal.
It is 276 that mass spectrum, which measures molecular weight of product,.
Embodiment 2:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press n-butanal afterwards: n-butanal 7.20g is added in two glycerol=1:0.5, according to n-butanal: protochloride is added in frerrous chloride=1:0.5
Iron catalyst 3.60g, under nitrogen atmosphere, stirring are warming up to 50 DEG C, and reaction is cooled to room temperature after 12 hours, gained reaction solution warp
Water washing, ethyl acetate extraction, saturated sodium carbonate solution washing remove catalyst, anhydrous sodium sulfate drying, vacuum concentration, use stone
Two glycerol acetonide only son's aldehyde, yield 85.3% are obtained after oily ether and ethyl alcohol (10:1) column chromatography.Mass spectrum measures molecular weight of product
220。
Embodiment 3:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press n-hexyl aldehyde afterwards: n-hexyl aldehyde 3.33g is added in two glycerol=1:1.5, according to n-hexyl aldehyde: magnesium chloride=1:0.07 (mass ratio, under
Magnesium chloride catalyst 0.23g is added together), under nitrogen atmosphere, stirring is warming up to 80 DEG C, and reaction is cooled to room temperature after 2 hours, institute
Reaction solution through water washing, ethyl acetate extraction, that saturated sodium carbonate solution washing removes catalyst, anhydrous sodium sulfate is dry, true
Sky concentration obtains two glycerol acetonide list hexanals, yield 86.6% after being chromatographed with petroleum ether and ethyl alcohol (17:1) column.
It is 248 that mass spectrum, which measures molecular weight of product,.
Embodiment 4:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press positive lauric aldehyde afterwards: positive lauric aldehyde 1.84g is added in two glycerol=1:5, according to positive lauric aldehyde: chlorination is added in barium chloride=1:0.1
Titanate catalyst 0.18g, under nitrogen atmosphere, stirring are warming up to 150 DEG C, and reaction is cooled to room temperature after 6 hours, gained reaction solution warp
Water washing, ethyl acetate extraction, saturated sodium carbonate solution washing remove catalyst, anhydrous sodium sulfate drying, vacuum concentration, use stone
Two glycerol acetonide list lauric aldehydes, yield 79.3% are obtained after oily ether and ethyl alcohol (25:1) column chromatography.
It is 332 that mass spectrum, which measures molecular weight of product,.
Embodiment 5:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press n-capric aldehyde afterwards: n-capric aldehyde 3.90g is added in two glycerol=1:2, according to n-capric aldehyde: chlorination calcium treating is added in calcium chloride=1:0.3
Agent 1.17g, under nitrogen atmosphere, stirring are warming up to 120 DEG C, and reaction is cooled to room temperature after 4 hours, and gained reaction solution is through washing
It washs, ethyl acetate extraction, saturated sodium carbonate solution washing removing catalyst, anhydrous sodium sulfate drying, vacuum concentration, uses petroleum ether
Two glycerol acetonide list capraldehyde, yield 80.7% are obtained with after ethyl alcohol (19:1) column chromatography.
It is 304 that mass spectrum, which measures molecular weight of product,.
Embodiment 6:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press valeraldehyde afterwards: valeraldehyde 21.50g is added in two glycerol=1:0.2, according to valeraldehyde: iron chloride is added in iron chloride=1:0.002
Catalyst 0.043g, under nitrogen atmosphere, stirring are warming up to 70 DEG C, and reaction is cooled to room temperature after 9 hours, and gained reaction solution is through water
Washing, ethyl acetate extraction, saturated sodium carbonate solution washing remove catalyst, anhydrous sodium sulfate drying, vacuum concentration, use petroleum
Two glycerol acetonide list valerals, yield 77.5% are obtained after ether and ethyl alcohol (15:1) column chromatography.
It is 234 that mass spectrum, which measures molecular weight of product,.
Embodiment 7:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press positive undecalactone afterwards: positive undecalactone 3.53g is added in two glycerol=1:3, according to positive undecalactone: chlorine is added in aluminium chloride=1:0.006
Change Al catalysts 0.021g, under nitrogen atmosphere, stirring is warming up to 200 DEG C, and reaction is cooled to room temperature after 3 hours, gained reaction
Liquid removes catalyst, anhydrous sodium sulfate drying, vacuum concentration through water washing, ethyl acetate extraction, saturated sodium carbonate solution washing,
Two glycerol acetonide list undecalactones, yield 76.4% are obtained after being chromatographed with petroleum ether and ethyl alcohol (27:1) column.
It is 360 that mass spectrum, which measures molecular weight of product,.
Embodiment 8:
Two glycerol 8.30g are added in the three neck round bottom flask that electromagnetic heater, condenser pipe, nitrogen ingress pipe are housed, so
Press positive hexadecanoyl afterwards: hexadecanoyl 2.86g is added in two glycerol=1:4.2, according to positive hexadecanoyl: chlorination is added in copper chloride=1:0.08
Copper catalyst 0.23g, under nitrogen atmosphere, stirring are warming up to 220 DEG C, and reaction is cooled to room temperature after 5 hours, gained reaction solution warp
Water washing, ethyl acetate extraction, saturated sodium carbonate solution washing remove catalyst, anhydrous sodium sulfate drying, vacuum concentration, use stone
Two glycerol acetonide list hexadecanoyls, yield 74.1% are obtained after oily ether and ethyl alcohol (30:1) column chromatography.
It is 388 that mass spectrum, which measures molecular weight of product,.
Embodiment 9: performance detection
1, surface tension properties:
The surface tension and critical micelle concentration (cmc) of surfactant solution are used with Wilhelmy platinum sheet
The measurement of KrussK100 surface tension instrument.With reference to GB/T22237-2008, in the measurements, Dosimat is utilizedTMDosimeter Xiang Chuhan
There is the solution for the surfactant for increasing 1ml0.6g/L in the container of 60ml deionized water, is then sufficiently stirred, extracts 1mL's
Solution measures the surface tension of generated solution to guarantee to measure liquid in containers constancy of volume, and 6s reads a data, measurement
It one minute, is finally averaged.Method more than each concentration point repeats.Sample test structure such as Fig. 2 institute of embodiment 3
Show.The critical micell solubility of the sample of embodiment 3 in aqueous solution is 3 × 10-4Mol/L, the surface under critical micelle concentration
Power γcmc=30mN/m.
2, foam properties
1 gained sample of embodiment is chosen, is compared with technical grade AEO-3 (contrast sample) in the prior art.
Roche foam method is improved according to national standard GB/T7462-94, test concentrations are 1g/L at 25 DEG C.1 sample of embodiment
Initial foam height and 5min foam height be 250mL and 200mL respectively.The initial foam height of comparative sample AEO-3 and
5min foam height is respectively 50mL and 30mL.Test concentrations are 1g/L, the initial foam height of 1 sample of embodiment at 40 DEG C
It is 300mL and 250mL respectively with 5min foam height.The initial foam height and 5min foam height of comparative sample AEO-3 is distinguished
For 80mL and 40mL.The result shows that the sample from the embodiment of the present invention 1, excellent in room temperature and 40 DEG C of foam properties.
3, the alkali resistance test under sodium hydroxide solution
To sample obtained by embodiment 1, embodiment 4 and embodiment 5 and with AEO-3's in the prior art (technical grade)
Alkali resistance comparison.
Sodium hydroxide alkali resistance test: respectively using the sodium hydroxide solution of 2.5wt%, 5wt% or 7.5wt% (with matter
Meter), sample of the embodiment of the present invention and contrast sample obtained by the 0.1%wt of used aqueous slkali is added, stirs 10min
Afterwards, it stands for 24 hours, observes the state of solution.The results are shown in Table 1.
Table 1
| Sample | 2.5% | 5% | 7.5% |
| Contrast sample AEO-3 | It is uniformly muddy | It is uneven muddy | It is uneven muddy |
| Embodiment 1 | It is unchanged | It is unchanged | It is uniformly muddy |
| Embodiment 4 | It is unchanged | It is uniformly muddy | It is uniformly muddy |
| Embodiment 5 | It is unchanged | It is uniformly muddy | It is uniformly muddy |
Unchanged in table 1: solution and original solution are without significant change.
Uniformly muddy: solution is more muddy than original solution, and uniformly.
Uneven muddy: solution has obvious layering or substance to be precipitated compared with original solution.
Seen from table 1, when the sample introduction of embodiment 1 is 2.5% and 5%, solution is unchanged；It is in additional amount
It is become cloudy when 7.5%.When the sample introduction of embodiment 4 and 5 is 2.5%, solution is unchanged；It is 5% and 7.5% in additional amount
When become cloudy.On the contrary, comparative sample AEO-3 becomes cloudy when additional amount is 2.5wt%, there is white under conditions of 5% and 7.5%
Insoluble matter is precipitated.The result shows that showing significantly excellent alkali resistance effect from sample of the invention compared with AEO-3.
4, hard water resistance test
It is compared to sample obtained by embodiment 1, embodiment 4 and embodiment 5 and with the hard water resistance property of comparative sample AEO-3.
Hard water resistance test: using the hard water (with calcium carbonate) of 1200ppm, 1800ppm or 2400ppm respectively, and institute is added
Sample of the embodiment of the present invention and contrast sample obtained by the 0.1%wt of the hard water used after stirring 10min, stand for 24 hours, see
Examine the state of solution.It the results are shown in Table shown in 2.
Table 2
| Sample | 1200ppm | 1800ppm | 2400ppm |
| Comparative sample AEO-3 | It is uniformly muddy | It is uniformly muddy | It is uneven muddy |
| Embodiment 1 | It is unchanged | It is unchanged | It is uniformly muddy |
| Embodiment 4 | It is unchanged | It is uniformly muddy | It is uniformly muddy |
| Embodiment 5 | It is unchanged | It is uniformly muddy | It is uniformly muddy |
Unchanged in table 2: solution and original solution are without significant change.
Uniformly muddy: solution is more muddy than original solution, and uniformly.
It is uneven muddy: to there is obvious layering or substance to be precipitated.
As can be seen from Table 2, solution is unchanged when the sample introduction of embodiment 1 is 1200ppm and 1800ppm；In additional amount
To be become cloudy when 2400ppm.When the sample introduction of embodiment 4 and 5 is 1200ppm, solution is unchanged；It is in additional amount
It is become cloudy when 1800ppm and 2400ppm.On the contrary, AEO-3 becomes cloudy when additional amount is 1200ppm and 1800ppm,
There is white insoluble matter to be precipitated under 2400ppm.The result shows that being shown significantly excellent from sample of the invention compared with AEO-3
Hard water resistance effect.
5, emulsifying capacity is tested
To sample obtained by preparation embodiment 1, embodiment 4 and embodiment 5 and with the AEO-3 of comparison in atoleine
Emulsifying capacity comparison.
Emulsifying capacity test: being added the obtained embodiment sample or comparative sample sample of pure water 2wt%, then adds respectively
Enter the atoleine of 10wt%, 30wt%, 50wt% of pure water, ultrasonic 10min stands 2h, observes the state of lotion.As a result
As shown in table 3.
Table 3
| Sample | 10% | 30% | 50% |
| Comparative sample AEO-3 | It is white homogeneous | It is white homogeneous | Creaming of emulsion |
| Embodiment 1 | It is white homogeneous | It is white homogeneous | It is white homogeneous |
| Embodiment 4 | It is white homogeneous | It is white homogeneous | It is white homogeneous |
| Embodiment 5 | It is white homogeneous | It is white homogeneous | It is white homogeneous |
In table 3, white is homogeneous: lotion is the phase of white uniformity；
Creaming of emulsion: lotion is obviously divided into two-phase.
Seen from table 3, when other conditions are identical, the sample and comparative sample of each embodiment are 10% and 30% in additional amount
When, it can be formed with base oil white homogeneous；When each embodiment and the water additional amount of comparative sample AEO-3 are 50%, embodiment
Sample still be able to be formed with atoleine white homogeneous, but comparative sample and atoleine can not form the homogeneous of white, appearance
Two-phase is significantly layered.It can be seen that emulsifying property of each embodiment sample than AEO-3 is good.
Claims (5)
1. a kind of preparation method of two glycerol monoacetals, it is characterised in that: use lewis acid for catalyst, without using any molten
The representative examples of saturated aliphatic aldehyde that agent, two glycerol of catalysis and carbon atom number are 4 ~ 16 occurs acetalation and prepares two glycerol monoacetals；Institute
The molar ratio for stating representative examples of saturated aliphatic aldehyde and two glycerol is 1:(0.2 ~ 5)；
The lewis acid catalyst is zinc chloride, barium chloride, magnesium chloride, calcium chloride, iron chloride, aluminium chloride, copper chloride or chlorine
Change one of ferrous iron；
The two glycerol monoacetal is following (I), (II), (III), four kinds of isomers shown in (IV) it is mixed
Close object:
Wherein R is C3 ~ C15 Straight chained alkyl.
2. the preparation method of two glycerol monoacetal according to claim 1, it is characterised in that: wherein R is C5 ~ C11It is straight
Alkyl group.
3. the preparation method of two glycerol monoacetal according to claim 1, it is characterised in that: the following steps are included:
(1) representative examples of saturated aliphatic aldehyde is mixed with two glycerol, using aldehyde as benchmark object, lewis acid is added as catalyst, stirring rises
Temperature is reacted 1 ~ 12 hour to 50 ~ 220 DEG C；
(2) after reaction, it chromatographs through washing, extraction, washing removing catalyst, drying, vacuum concentration, column and to obtain the contracting of two glycerol lists
Aldehyde product.
4. the preparation method of two glycerol monoacetal according to claim 3, it is characterised in that: the representative examples of saturated aliphatic aldehyde with
The molar ratio of two glycerol is 1:0.2 ~ 2, and the mass ratio of aldehyde and lewis acid catalyst is 1:0.002 ~ 1.
5. the preparation method of two glycerol monoacetal according to claim 3, it is characterised in that: in the step (2), reaction
After, it adopts and is washed with distilled water, ethyl acetate extraction, saturated sodium carbonate solution washing remove catalyst, use anhydrous slufuric acid
Sodium is dry, chromatographs to obtain two glycerol monoacetals using the volume ratio 10-30:1 column of petroleum ether and ethyl alcohol.
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