CN104987284A - Organic nonlinear optical compound chalcone dibromide synthetic method - Google Patents
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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Abstract
The invention discloses an organic nonlinear optical compound chalcone dibromide synthetic method. The method comprises the steps of conducting aldol reaction under the solvent-free alkaline condition with acetophenone and benzaldehyde as raw materials, so that alpha, beta- unsaturated chalcone is obtained; adding alpha, beta- unsaturated chalcone obtained in the first step and bromine into an organic solvent for addition reaction, so that chalcone dibromide is obtained. According to the method, raw materials are easy to obtain, price is low, alpha, beta- unsaturated chalcone is obtained through aldol reaction under the solvent-free alkaline condition, cost is low, and atom economic benefits are high; dichloroethane or dichloromethane serves as the organic solvent which is better than carbon tetrachloride, dichloroethane is easy to recover so that cost can be further reduced, the toxicity of dichloromethane is low so that great harm to people can not be caused, and environment friendliness is realized.
Description
Technical field
The present invention relates to nlo compound synthesis technical field, particularly relate to a kind of synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone.
Background technology
Organic non-linear compound has unique conjugated pi electron polarization system, produce when Charger transfer larger non-linear, in the non-linear behaviour that this compounds shows in nonlinear optics, photodamage resistant and response speed etc., be far superior to inorganic materials.
Cinnamophenone and derivative thereof are by the product that cross aldol condensation occurs between aromatic aldehyde ketone.Cinnamophenone is present in occurring in nature, is the precursor of synthesis flavones in plant materials, has important pharmacological action.Chalcone derivative is a kind of novel organic non linear optical material, has larger non-linear optical effect, frequency multiplication is effective, anti-optical damage.This analog derivative is often used as novel screen protection and liquid crystal display material.Dibromo phenyl styryl ketone has larger non-linear optical effect, visible ray and near ultraviolet region have compared with number transparency range, there is certain use value, may be used in high resolution lithography glue, and in blue light OLED, there is huge application potential.
Dibromo phenyl styryl ketone, chemistry 2,3-bis-bromo-1,3-phenylbenzene-1-acetone by name.This compound is the pressed powder of white, water insoluble, is slightly soluble in alcohols, is soluble in ethyl acetate.Its structure is following as shown:
At present conventional synthetic route be with methyl phenyl ketone simple and easy to get and phenyl aldehyde for raw material, carry out aldol condensation in the basic conditions, generate α, β-unsaturated cinnamophenone.Use bromine by obtained 2,3-bis-bromo-1, the 3-phenylbenzene-1-acetone of addition reaction.Synthetic route as shown in the formula:
In current production technology, the solvent that the aldol reaction of methyl phenyl ketone and phenyl aldehyde often adopts is ethanol, and cost of material is high, and last handling process not easily reclaims.In the bromine addition reaction of second step, general employing tetracol phenixin is solvent.Tetracol phenixin toxicity is large, by national strict management and control, extremely unfriendly to environment, is not suitable for suitability for industrialized production.
Summary of the invention
Based on the technical problem that background technology exists, the present invention proposes a kind of synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone, raw material is easy to get, low price, in alkalescence, obtain generating α through aldol condensation under condition of no solvent, β-unsaturated cinnamophenone, cost is low, atom economy high efficiency, adopt ethylene dichloride or methylene dichloride as organic solvent, be better than tetracol phenixin, wherein ethylene dichloride is easy to reclaim, greatly reduce cost further, and the toxicity of methylene dichloride is hypotoxicity, excessive harm can not be caused to human body, and it is environmentally friendly.
The synthetic method of a kind of nonlinear optical organic compound dibromo phenyl styryl ketone that the present invention proposes, comprises the steps:
S1, with methyl phenyl ketone and phenyl aldehyde for raw material, under solvent-free alkaline condition, carry out aldol condensation obtain α, β-unsaturated cinnamophenone;
S2, α, β-unsaturated cinnamophenone and bromine added in organic solvent and carries out addition reaction and obtain dibromo cinnamophenone.
The chemical equation of the preparation method of dibromo cinnamophenone of the present invention is:
Preferably, in S1, solvent-free alkaline condition is solid sodium hydroxide.
Preferably, in S1, the mol ratio of methyl phenyl ketone, phenyl aldehyde and sodium hydroxide is 1:1-1.3:1.2-1.5, such as 1:1.2:1.3,1:1.1-1.25:1.2-1.4,1:1.23:1.34, is preferably 1:1.1:1.25.
Preferably, in S1, the temperature of aldol reaction is 55-60 DEG C, such as 55.5 DEG C, 55-58 DEG C, 59 DEG C, 59.8 DEG C.
Preferably, in S1, the time of aldol reaction is 7-10h, such as 7.2h, 7.6h, 8-9h, 9.8h.
Preferably, the concrete operations of S1 are: by methyl phenyl ketone, phenyl aldehyde and solid sodium hydroxide in molar ratio for 1:1-1.3:1.2-1.5 adds in reaction vessel, be warming up to 55-60 DEG C, and insulation 7-10h obtains mixture, then purify and obtain α, β-unsaturated cinnamophenone.
Preferably, in S1, the concrete operations of purification are: in mixture, add deionized water carry out cancellation reaction, be cooled to 10-15 DEG C in cancellation reaction process, separate out solid, suction filtration, filter cake is washed to neutrality and obtains the first material after stirring 3-4h; By the first material ethanol room temperature making beating 1-1.2h of 95%, filter, filter cake vacuum-drying is obtained α, β-unsaturated cinnamophenone.
Preferably, in the purification of S1, vacuum drying temperature is 35-40 DEG C, such as 36 DEG C, 36.3 DEG C, 37 DEG C, 37.7 DEG C, 38-40 DEG C, 39 DEG C, be preferably 40 DEG C.
Preferably, in the purification of S1, the mass ratio of deionized water and methyl phenyl ketone is 3-5:1, such as 3.3:1,3.8:1,4:1,4.2:1,4.6:1,4.8:1.
Preferably, in the purification of S1, the ethanol of 95% and the mass ratio of methyl phenyl ketone are 1-2:1, such as 1:1,1.1:1,1.3:1,1.4:1,1.5:1,1.6:1,1.7-1.9:1, are preferably 1.2:1.
Preferably, in S2, the mol ratio of α, β-unsaturated cinnamophenone and bromine is 1:1-1.5, such as 1:1.1,1:1.2-1.3,1:1.4-1.45,1:1.48, is preferably 1:1.08.
Preferably, in S2, the mass ratio of α, β-unsaturated cinnamophenone and organic solvent is 1:3-5, such as 1:3.2-3.6,1:4,1:4.3-4.7,1:4.8,1:4.9, is preferably 1:4.5.
Preferably, organic solvent is methylene dichloride or ethylene dichloride.
Preferably, the concrete operations of S2 are: the α obtained by S1, β-unsaturated cinnamophenone and organic solvent drop in reaction vessel, be cooled to 0-5 DEG C, in the reaction vessel containing α, β-unsaturated cinnamophenone and organic solvent, drip bromine, in dropping process, temperature is 0-20 DEG C, then rise to room temperature, stir 6-8h; Work as α, during β-unsaturated cinnamophenone content≤0.5%, add saturated sodium sulfite aqueous solution, filter, by filtrate stratification, take off a layer solution, distillation obtains the pressed powder of white; The pressed powder of white is added in the ethanol of 95% and pull an oar, filter, filter cake vacuum-drying is obtained dibromo cinnamophenone.
Preferably, in S2, the mass ratio of sodium sulfite saturated aqueous solution and bromine is 0.3-0.6:1, such as 0.32-0.38:1,0.4:1,0.43:1,0.46-0.49:1, is preferably 0.5:1.
Preferably, in S2, the mass ratio of the ethanol of 95% and α, β-unsaturated cinnamophenone is 1.5-2:1, such as 1.52-1.64:1,1.7:1,1.75-1.9:1, is preferably 1.8:1.
Preferably, in S2, vacuum drying temperature is 35-40 DEG C, such as 36 DEG C, 36.3 DEG C, 37 DEG C, 37.7 DEG C, 38-40 DEG C, 39 DEG C, be preferably 40 DEG C.
Room temperature in the present invention is 20-25 DEG C.
Making beating is the method for purifying substance, and determine according to the nature difference of impurity and material, solvent material being put into not easily dissolved product stirs, and filters, reach the effect that purifying products is refining after the impurities dissolves being soluble in solvent.
In the purification process of S1, slowly should add deionized water, and slow cooling.
In S2, slowly should drip bromine, more slowly be warming up to room temperature, then slowly add saturated sodium sulfite aqueous solution.
In the present invention, S1 synthesizes the α obtained, and the liquid phase purity of β-unsaturated cinnamophenone can reach the liquid phase purity that more than 98.5%, S2 synthesizes the dibromo cinnamophenone obtained can reach more than 99%.
The present invention with methyl phenyl ketone and phenyl aldehyde for raw material, cheaply, be easy to get, in alkalescence, obtain generating α through aldol condensation under condition of no solvent, β-unsaturated cinnamophenone, cost is low, atom economy high efficiency, and α, when the double bond of β-unsaturated cinnamophenone carries out bromination, the present invention proposes a kind of synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone, raw material is easy to get, low price, in alkalescence, obtain generating α through aldol condensation under condition of no solvent, β-unsaturated cinnamophenone, cost is low, atom economy high efficiency, adopt ethylene dichloride or methylene dichloride as organic solvent, be better than tetracol phenixin, wherein ethylene dichloride is easy to reclaim, greatly reduce cost further, and the toxicity of methylene dichloride is hypotoxicity, excessive harm can not be caused to human body, and it is environmentally friendly.
Research display, a lot of reaction does not need solvent just can carry out well, this means may no longer need to improve reaction efficiency by selective solvent in organic synthesis, if and aldol reaction of the present invention is without de-water mitigation, then there is the Atom economy of 100%, meet the definition of Green Chemistry completely.
Embodiment
Below, by specific embodiment, technical scheme of the present invention is described in detail.
Embodiment 1
Add in reaction vessel by molar part by 1 part of methyl phenyl ketone, 1 part of phenyl aldehyde and 1.5 parts of solid sodium hydroxides, be warming up to 55 DEG C, insulation 10h obtains mixture; In mixture, add deionized water carry out cancellation reaction, in cancellation reaction process, be cooled to 10 DEG C, separate out solid, suction filtration after stirring 4h, filter cake is washed to neutrality and obtains the first material; By the first material ethanol room temperature making beating 1h of 95%, filter, filter cake vacuum-drying is obtained α, β-unsaturated cinnamophenone, wherein the mass ratio of deionized water and methyl phenyl ketone is 5:1, and the ethanol of 95% and the mass ratio of methyl phenyl ketone are 1:1, and wherein vacuum drying temperature is 40 DEG C.
Drop in reaction vessel by the α that 1 part of S1 obtains by molar part, β-unsaturated cinnamophenone and ethylene dichloride, be cooled to 0 DEG C, in the reaction vessel containing α, β-unsaturated cinnamophenone and ethylene dichloride, drip 1.5 parts of bromines, in dropping process, temperature is 0 DEG C, then rise to room temperature, stir 8h; Work as α, during β-unsaturated cinnamophenone content≤0.5%, add saturated sodium sulfite aqueous solution, filter, by filtrate stratification, take off a layer solution, distillation obtains the pressed powder of white; The pressed powder of white is added in the ethanol of 95% and pull an oar, filter, filter cake vacuum-drying is obtained dibromo cinnamophenone, wherein α, the mass ratio of β-unsaturated cinnamophenone and ethylene dichloride is 1:3, and the mass ratio of sodium sulfite saturated aqueous solution and bromine is 0.6:1, the ethanol of 95% and α, the mass ratio of β-unsaturated cinnamophenone is 1.5:1, and vacuum drying temperature is 40 DEG C.
Embodiment 2
Add in reaction vessel by molar part by 1 part of methyl phenyl ketone, 1.1 parts of phenyl aldehydes and 1.25 parts of solid sodium hydroxides, be warming up to 57 DEG C, insulation 8.5h obtains mixture; In mixture, add deionized water carry out cancellation reaction, in cancellation reaction process, be cooled to 12 DEG C, separate out solid, suction filtration after stirring 3.5h, filter cake is washed to neutrality and obtains the first material; By the first material ethanol room temperature making beating 1.1h of 95%, filter, filter cake vacuum-drying is obtained α, β-unsaturated cinnamophenone, wherein the mass ratio of deionized water and methyl phenyl ketone is 4:1, and the ethanol of 95% and the mass ratio of methyl phenyl ketone are 1.2:1, and wherein vacuum drying temperature is 40 DEG C.
Drop in reaction vessel by the α that 1 part of S1 obtains by molar part, β-unsaturated cinnamophenone and methylene dichloride, be cooled to 2 DEG C, in the reaction vessel containing α, β-unsaturated cinnamophenone and methylene dichloride, drip 1.08 parts of bromines, in dropping process, temperature is 10 DEG C, then rise to room temperature, stir 7h; Work as α, during β-unsaturated cinnamophenone content≤0.5%, add saturated sodium sulfite aqueous solution, filter, by filtrate stratification, take off a layer solution, distillation obtains the pressed powder of white; The pressed powder of white is added in the ethanol of 95% and pull an oar, filter, filter cake vacuum-drying is obtained dibromo cinnamophenone, wherein α, the mass ratio of β-unsaturated cinnamophenone and methylene dichloride is 1:4.5, and the mass ratio of sodium sulfite saturated aqueous solution and bromine is 0.5:1, the ethanol of 95% and α, the mass ratio of β-unsaturated cinnamophenone is 1.8:1, and vacuum drying temperature is 40 DEG C.
Embodiment 3
Add in reaction vessel by molar part by 1 part of methyl phenyl ketone, 1.3 parts of phenyl aldehydes and 1.2 parts of solid sodium hydroxides, be warming up to 60 DEG C, insulation 7h obtains mixture; In mixture, add deionized water carry out cancellation reaction, in cancellation reaction process, be cooled to 15 DEG C, separate out solid, suction filtration after stirring 3h, filter cake is washed to neutrality and obtains the first material; By the first material ethanol room temperature making beating 1.2h of 95%, filter, filter cake vacuum-drying is obtained α, β-unsaturated cinnamophenone, wherein the mass ratio of deionized water and methyl phenyl ketone is 3:1, and the ethanol of 95% and the mass ratio of methyl phenyl ketone are 2:1, and wherein vacuum drying temperature is 35 DEG C.
Drop in reaction vessel by the α that 1 part of S1 obtains by molar part, β-unsaturated cinnamophenone and methylene dichloride, be cooled to 5 DEG C, in the reaction vessel containing α, β-unsaturated cinnamophenone and methylene dichloride, drip 1 part of bromine, in dropping process, temperature is 20 DEG C, then rise to room temperature, stir 6h; Work as α, during β-unsaturated cinnamophenone content≤0.5%, add saturated sodium sulfite aqueous solution, filter, by filtrate stratification, take off a layer solution, distillation obtains the pressed powder of white; The pressed powder of white is added in the ethanol of 95% and pull an oar, filter, filter cake vacuum-drying is obtained dibromo cinnamophenone, wherein α, the mass ratio of β-unsaturated cinnamophenone and methylene dichloride is 1:5, and the mass ratio of sodium sulfite saturated aqueous solution and bromine is 0.3:1, the ethanol of 95% and α, the mass ratio of β-unsaturated cinnamophenone is 2:1, and vacuum drying temperature is 35 DEG C.
Embodiment 4
In advance 100g sodium hydroxide is ground to powdery, then 240g methyl phenyl ketone, 234g phenyl aldehyde and 100g powdered sodium hydroxide is positioned in the first reaction vessel and stirs, be then warmed up to 55 DEG C, then obtain mixture at 55-60 DEG C of insulation 7h; In mixture, slowly add 1000g deionized water, then slow cooling to 10 DEG C, separate out solid, suction filtration after stirring 3h, be washed to neutrality and obtain the first material; First material is added in the second reaction vessel, add 400g 95% ethanol again, room temperature making beating 1h, filter, filter cake vacuum-drying is obtained 362g flaxen α, β-unsaturated cinnamophenone crystal, yield is 87%, liquid phase purity reaches 99.2%, and wherein vacuum drying temperature is 40 DEG C, and the vacuum drying time is 5h.
200g α, β-unsaturated cinnamophenone and 1000g ethylene dichloride are placed in the 3rd reaction vessel stir, are then cooled to 0 DEG C, then slowly drip 161g bromine, within 2 hours, dropwise, be slowly warming up to room temperature, insulation 6h, liquid phase follows the tracks of reaction process, works as α, β-unsaturated cinnamophenone content≤0.5%, slowly add the sodium sulfite aqueous solution that 90g is saturated, filter, by filtrate stratification, take off a layer solution, distillation obtains the pressed powder of white; The pressed powder of white is added in 360g 95% ethanol and pull an oar, filter, filter cake vacuum-drying is obtained the dibromo cinnamophenone solid of 218g white, yield is 61.7%, liquid phase purity is 99.2%, and wherein vacuum drying temperature is 40 DEG C, and the vacuum drying time is 5h.
The above; be only the present invention's preferably embodiment; but protection scope of the present invention is not limited thereto; anyly be familiar with those skilled in the art in the technical scope that the present invention discloses; be equal to according to technical scheme of the present invention and inventive concept thereof and replace or change, all should be encompassed within protection scope of the present invention.
Claims (10)
1. a synthetic method for nonlinear optical organic compound dibromo phenyl styryl ketone, is characterized in that, comprise the steps:
S1, with methyl phenyl ketone and phenyl aldehyde for raw material, under solvent-free alkaline condition, carry out aldol reaction obtain α, β-unsaturated cinnamophenone;
S2, the α obtained by S1, β-unsaturated cinnamophenone and bromine add in organic solvent and carry out addition reaction and obtain dibromo cinnamophenone.
2. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to claim 1, it is characterized in that, in S1, solvent-free alkaline condition is solid sodium hydroxide; Preferably, in S1, the mol ratio of methyl phenyl ketone, phenyl aldehyde and sodium hydroxide is 1:1-1.3:1.2-1.5, is preferably 1:1.1:1.25.
3. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to claim 1 or 2, it is characterized in that, in S1, the temperature of aldol reaction is 55-60 DEG C; Preferably, in S1, the time of aldol reaction is 7-10h.
4. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to any one of claim 1-3, it is characterized in that, the concrete operations of S1 are: by methyl phenyl ketone, phenyl aldehyde and solid sodium hydroxide in molar ratio for 1:1-1.3:1.2-1.5 adds in reaction vessel, be warming up to 55-60 DEG C, insulation 7-10h obtains mixture, then purify and obtain α, β-unsaturated cinnamophenone; Preferably, in S1, the concrete operations of purification are: in mixture, add deionized water carry out cancellation reaction, be cooled to 10-15 DEG C in cancellation reaction process, separate out solid, suction filtration, filter cake is washed to neutrality and obtains the first material after stirring 3-4h; By the first material ethanol room temperature making beating 1-1.2h of 95%, filter, filter cake vacuum-drying is obtained α, β-unsaturated cinnamophenone; Preferably, in the purification of S1, vacuum drying temperature is 35-40 DEG C, is preferably 40 DEG C.
5. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to claim 4, it is characterized in that, in the purification of S1, the mass ratio of deionized water and methyl phenyl ketone is 3-5:1; Preferably, in the purification of S1, the ethanol of 95% and the mass ratio of methyl phenyl ketone are 1-2:1, are preferably 1.2:1.
6. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to any one of claim 1-5, it is characterized in that, in S2, the mol ratio of α, β-unsaturated cinnamophenone and bromine is 1:1-1.5, is preferably 1:1.08.
7. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to any one of claim 1-6, it is characterized in that, in S2, the mass ratio of α, β-unsaturated cinnamophenone and organic solvent is 1:3-5, is preferably 1:4.5; Preferably, organic solvent is methylene dichloride or ethylene dichloride.
8. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to any one of claim 1-7, it is characterized in that, the concrete operations of S2 are: the α obtained by S1, β-unsaturated cinnamophenone and organic solvent drop in reaction vessel, are cooled to 0-5 DEG C, to containing α, bromine is dripped in the reaction vessel of β-unsaturated cinnamophenone and organic solvent, in dropping process, temperature is 0-20 DEG C, then rises to room temperature, stirs 6-8h; Work as α, during β-unsaturated cinnamophenone content≤0.5%, add saturated sodium sulfite aqueous solution, filter, by filtrate stratification, take off a layer solution, distillation obtains the pressed powder of white; The pressed powder of white is added in the ethanol of 95% and pull an oar, filter, filter cake vacuum-drying is obtained dibromo cinnamophenone.
9. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to any one of claim 1-8, it is characterized in that, in S2, the mass ratio of sodium sulfite saturated aqueous solution and bromine is 0.3-0.6:1, is preferably 0.5:1; Preferably, in S2, the mass ratio of the ethanol of 95% and α, β-unsaturated cinnamophenone is 1.5-2:1, is preferably 1.8:1.
10. the synthetic method of nonlinear optical organic compound dibromo phenyl styryl ketone according to any one of claim 1-9, it is characterized in that, in S2, vacuum drying temperature is 35-40 DEG C, is preferably 40 DEG C.
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| CN107935831A (en) * | 2017-12-06 | 2018-04-20 | 福州大学 | A kind of method of mantoquita catalysis aldol reaction |
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