CN1134445C - Method for preparing dibenzyl sorbitol - Google Patents
Method for preparing dibenzyl sorbitol Download PDFInfo
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- CN1134445C CN1134445C CNB991099141A CN99109914A CN1134445C CN 1134445 C CN1134445 C CN 1134445C CN B991099141 A CNB991099141 A CN B991099141A CN 99109914 A CN99109914 A CN 99109914A CN 1134445 C CN1134445 C CN 1134445C
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- sorbitol
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- sorbyl alcohol
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Abstract
The present invention belongs to a method for preparing dibenzylidene sorbitol, which uses sorbitol and benzaldehyde as raw materials and uses hexane as solvents. The sorbitol is dewatered beforehand, and a condensation reaction is carried out for the sorbitol in a reactor provided with a stirring device under the condition of nitrogen protection at the reaction temperature of 65 to 75 DEG C for 2.5 to 3.5 hours; in this way, the dibenzylidene sorbitol of which the purity is above 90% is prepared, and the yield of the dibenzylidene sorbitol is larger than 80%. About 0.3% of the dibenzylidene sorbitol is added to linear low-density polyethylene to reduce haze degree by above 50%, and a small amount of the dibenzylidene sorbitol is added to benzene to solidify the benzene in 10 minutes.
Description
The invention belongs to the Sorbitol dibenzal preparation method of (being called for short DBS).
Sorbitol dibenzal is that condensation under the condition of acid catalyst forms by phenyl aldehyde and sorbyl alcohol.Because aldolization is the liquid liquid-liquid heterogeneous reaction, reaction has reversibility, and reaction solvent plays gelification to resultant, causes and stirs difficulty, and the dispersiveness of reaction mass descends, and produces side reaction, and ultimate yield descends, and the reaction times prolongs.The method that Chinese patent 92113390.1 discloses the synthetic method employing that is entitled as a kind of polyolefine clearing additive is to make catalyzer with sulfuric acid, with N, water-soluble solvent such as dinethylformamide or N-Methyl pyrrolidone and lower alcohol is as hybrid reaction promotor, use the cyclohexane give solvent, with 70% weight technical grade sorbyl alcohol and phenyl aldehyde is raw material, 75 ℃ of reflux temperatures react 5～6 hours through acetone refining, and the preparation yield reaches 60% Sorbitol dibenzal.Since moisture more in the raw material sorbyl alcohol, be unfavorable for reacting and carry out, the reaction times is prolonged, productive rate reduces.
The preparation method who the purpose of this invention is to provide a kind of Sorbitol dibenzal, it is raw material that this method adopts sorbyl alcohol and phenyl aldehyde, and sorbyl alcohol is dewatered in advance, hexane is a solvent, adopt the vitriol oil to make catalyzer, add reaction promotor, through reflux, aldolization is fully carried out, the dry Sorbitol dibenzal that gets, yield are more than 80%, and method of the present invention shortens the reaction times, the yield height, cost is low.
In order to achieve the above object, the present invention adopts 70% weight ratio technical grade sorbitol aqueous solution, dehydration in advance, it is raw material that benzoic acid content is lower than 1% weight ratio phenyl aldehyde, the vitriol oil is made catalyzer, N, and dinethylformamide is made reaction promotor, hexane is a solvent, because the hexane boiling point is low, but the double as dewatering agent, and the whipping appts that the present invention adopts is general frame-anchor-tiltedly starch agitator, low whipping speed is operation in the 150-200 rev/min of scope, in temperature is under 65～75 ℃, and sorbyl alcohol dewaters in advance its concentration is reached more than 85%, and product does not need through refining, wash out unreacted reactant with general tap water, dry then getting final product.
The present invention adopts 70% weight ratio technical grade sorbitol aqueous solution; it is raw material that benzoic acid content is lower than 1% weight ratio phenyl aldehyde; hexane is a solvent; three's weight ratio is 1: 0.88～1.17: 9.16～12.8; specific embodiment is that frame-anchor-tiltedly starch agitator is being housed; thermometer; the liquid liquid cooling is coagulated and is added 70% weight ratio sorbitol aqueous solution in the reactor of separator; hexane solvent; in temperature is under 65～75 ℃; water content is lower than 15% to the sorbyl alcohol; the N that under nitrogen protection, adds the 5-20% weight ratio then; dinethylformamide; add phenyl aldehyde; add the vitriol oil of the 1.0-1.5% of sorbyl alcohol weight, under 65～75 ℃ of temperature, react, in time water is taken out of through the liquid liquid/gas separator; in the hexane Returning reacting system; react after 2.5～3.5 hours, in alkali lye and an acidic catalyst, be washed till neutrality with tap water; filter after drying; promptly get the Sorbitol dibenzal of the white powder of purity more than 90%, yield is more than 80%.
The present invention is raw material owing to directly use 70% weight ratio technical grade sorbitol aqueous solution and benzoic acid content to be lower than 1% weight ratio phenyl aldehyde, with hexane or raffinate oil replacement hexanaphthene or heptane, cost is reduced, and do not adopt dewatering agent in the technological process in addition, promptly solvent plays dewatering agent simultaneously.Product need not made with extra care, and washes out unreacted reactant with general tap water.The DBS that adopts the present invention's preparation is as the polyolefin plastics additive, has that consumption is few, effective, the characteristics of safety non-toxic.
The Sorbitol dibenzal of the present invention's preparation can be made the transparence additive of polyolefin polymer, when plastic product formings such as polyethylene and polypropylene, adds the mist degree that a small amount of Sorbitol dibenzal can reduce plastics, enhances the transparency; Be convenient to reclaim and guarantee safety as the solidifying agent of oil plant; In coating, can do anti-settling and conciliate the change agent; In caking agent, make tackifier, separate the change agent; In printing ink, separate and become agent, dispersion agent; In daily use chemicals and medical supplies, also has extensive use.
Embodiment provided by the invention is as follows:
Embodiment 1:
Add 10.5 gram 70% weight ratio sorbyl alcohol and 120 ml n-hexanes in that frame-anchor-tiltedly starch agitator, thermometer, profit are housed in condensation divides the 250ml reactor of device, about 1 hour of 70 ℃ of following reflux are divided 1.5 milliliters of water outlets.Under nitrogen protection, add 3.0 milliliters of N successively then, dinethylformamide, 7.4 milliliters and 0.15 milliliter vitriol oil of phenyl aldehyde.Under 75 ℃, react after 3.0 hours, add the alkali lye termination reaction, be washed till neutrality with tap water, dry that Sorbitol dibenzal 12.6 restrains through vacuum drying oven, fusing point is 210-216 ℃, yield is 95.2%.
Embodiment 2:
Divide in the 250ml reactor of device from condensation in that frame-anchor-tiltedly starch agitator, thermometer, liquid liquid are housed, add 10.5 gram 70% weight ratio sorbyl alcohol and 120 ml n-hexanes, about 1 hour of 70 ℃ of following reflux are divided 1.5 milliliters of water outlets.Under nitrogen protection; add 3.0 milliliters of N successively; dinethylformamide, 6.2 milliliters and 0.15 milliliter vitriol oil of phenyl aldehyde; under 75 ℃, react after 3.0 hours, add the alkali lye termination reaction; be washed till neutrality with tap water; dry that Sorbitol dibenzal 9.7 restrains through vacuum drying oven, fusing point is 206-210 ℃, and yield is 86.0%.
Embodiment 3:
Divide in the 250ml reactor of device from condensation in that frame-anchor-tiltedly starch agitator, thermometer, liquid liquid are housed, add 10.5 grams, 70% weight ratio sorbyl alcohol, 120 ml n-hexanes successively, about 1 hour of 70 ℃ of following reflux are divided 1.5 milliliters of water outlets.Under nitrogen protection; add 3.0 milliliters of N successively; dinethylformamide, 8.2 milliliters and 0.15 milliliter vitriol oil of phenyl aldehyde; under 75 ℃, react after 3.0 hours, add the alkali lye termination reaction; be washed till neutrality with tap water; dry that Sorbitol dibenzal 12.0 restrains through vacuum drying oven, fusing point is 210-216 ℃, and yield is 82.0%.
Embodiment 4:
Divide in the 1000ml reactor of device from condensation in that frame-anchor-tiltedly starch agitator, thermometer, liquid liquid are housed, add 40.5 grams, 70% weight ratio sorbyl alcohol, 400 ml n-hexanes successively, about 1 hour of 70 ℃ of following reflux are divided 6.0 milliliters of water outlets.Under nitrogen protection; add 12.0 milliliters of N successively; dinethylformamide, 30.0 milliliters and 0.60 milliliter vitriol oil of phenyl aldehyde; under 75 ℃, react after 3.0 hours, add the alkali lye termination reaction; be washed till neutrality with tap water; dry that Sorbitol dibenzal 43.4 restrains through vacuum drying oven, fusing point is 204-210 ℃, and yield is 82.0%.
Claims (1)
1. the preparation method of a Sorbitol dibenzal; it is characterized in that adopting 70% weight ratio technical grade sorbitol aqueous solution; it is raw material that benzoic acid content is lower than 1% weight ratio phenyl aldehyde; hexane is a solvent; three's weight ratio is 1: 0.88～1.17: 9.16～12.8; specific embodiment is that frame-anchor-tiltedly starch agitator is being housed; thermometer; the liquid liquid cooling is coagulated and is added 70% weight ratio sorbitol aqueous solution in the reactor of separator; hexane solvent; 65～75 ℃ of reflux temperature; water content is lower than 15% to the sorbyl alcohol; then under nitrogen protection; with the raw material sorbyl alcohol is benchmark; add 5～20% weight ratio N respectively; dinethylformamide; add phenyl aldehyde; 1.0～1.5% the vitriol oil that adds sorbyl alcohol weight; under 65～75 ℃ of temperature, react; in time water is taken out of through the liquid liquid/gas separator; in the hexane Returning reacting system; react after 2.5～3.5 hours; in alkali lye and an acidic catalyst; be washed till neutrality with tap water; filter after drying, promptly get the Sorbitol dibenzal of the white powder of purity more than 90%, yield is more than 80%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB991099141A CN1134445C (en) | 1999-06-23 | 1999-06-23 | Method for preparing dibenzyl sorbitol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB991099141A CN1134445C (en) | 1999-06-23 | 1999-06-23 | Method for preparing dibenzyl sorbitol |
Publications (2)
| Publication Number | Publication Date |
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| CN1290679A CN1290679A (en) | 2001-04-11 |
| CN1134445C true CN1134445C (en) | 2004-01-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB991099141A Expired - Fee Related CN1134445C (en) | 1999-06-23 | 1999-06-23 | Method for preparing dibenzyl sorbitol |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101423520B (en) * | 2008-12-08 | 2010-12-22 | 中国科学院新疆理化技术研究所 | Method for synthesizing dibenzylidene sorbitol and dibenzylidene eutrit |
| CN107033866B (en) * | 2015-07-13 | 2020-12-11 | 中国石油化工股份有限公司 | Thick oil emulsifying viscosity reducer and preparation method and application thereof |
| CN106076411B (en) * | 2016-07-07 | 2018-05-29 | 清华大学 | A kind of sulfuric acid catalysis compound and the application in gasoline alkylate is produced |
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1999
- 1999-06-23 CN CNB991099141A patent/CN1134445C/en not_active Expired - Fee Related
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