CN109180454A - A kind of preparation method of parahydroxyben-zaldehyde - Google Patents
A kind of preparation method of parahydroxyben-zaldehyde Download PDFInfo
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- CN109180454A CN109180454A CN201810774561.5A CN201810774561A CN109180454A CN 109180454 A CN109180454 A CN 109180454A CN 201810774561 A CN201810774561 A CN 201810774561A CN 109180454 A CN109180454 A CN 109180454A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C45/64—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 functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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Abstract
The present invention provides a kind of preparation methods of parahydroxyben-zaldehyde, the removal of impurities of the preparation of preparation, intermediate II, the preparation of parahydroxyben-zaldehyde, parahydroxyben-zaldehyde solution including intermediate compound I, parahydroxyben-zaldehyde solution five steps of purification.Synthesis technology simple specification of the present invention, production technology and production procedure are easily grasped, while effectively raising parahydroxyben-zaldehyde production job specification, effectively raise the utilization rate to p-methyl phenol raw material, by a hydration ammonia as the reactant with p-methyl phenol raw material, not only p-methyl phenol reaction is more rapid, more sufficiently, and generating after reacting is that ammonium sulfate impurity is more easy to handle, the purifying technique of parahydroxyben-zaldehyde is increased in the preparation process of parahydroxyben-zaldehyde, the purity for the parahydroxyben-zaldehyde prepared can effectively be improved.
Description
Technical field
The present invention relates to a kind of preparation methods of parahydroxyben-zaldehyde, belong to chemical technology field.
Background technique
Parahydroxyben-zaldehyde is the important intermediate of organic synthesis, is widely used in medicine, fragrance, plating, food and pesticide
Equal fine chemical products.The demand of parahydroxyben-zaldehyde international market is significantly increased in recent years, and price rises steadily, and China is to hydroxyl
Although benzaldehyde manufacturer has more than ten, but factory still uses traditional phenol (formaldehyde) method mostly, not only PARA FORMALDEHYDE PRILLS(91,95)
Utilization rate it is not high, and the parahydroxyben-zaldehyde purity prepared is also not ideal enough, therefore is badly in need of a kind of high usage high-purity
Parahydroxyben-zaldehyde preparation method.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation methods of parahydroxyben-zaldehyde, to solve the prior art
The problems such as existing preparation process complexity and lower production efficiency.
In order to solve the above-mentioned technical problem, The technical solution adopted by the invention is as follows:
A kind of preparation method of parahydroxyben-zaldehyde, which is characterized in that the preparation method packet of the parahydroxyben-zaldehyde
Include following steps:
1) preparation of intermediate compound I: p-methyl phenol solution is placed in quartz reaction kettle, is then added to quartz reaction kettle
Excessive 50~64% (NH3) H2O solution and suitable catalyzed methanol solution for reaction, maintains the temperature at
In 8~16 DEG C, under strong illumination, be stirred 70~90min using agitating device, obtain intermediate compound I, methanol solution and
(NH3) mixed solution of H2O.
2) mixed solution of intermediate compound I, methanol solution and (NH3) H2O the preparation of intermediate II: are obtained to step 1)
In be continually fed into concentration be 90~98% oxygen, stir 2-4h of the mixed solution with agitating device while being passed through oxygen lateral dominance,
Obtain the mixed solution of intermediate II, methanol solution and (NH3) H2O.
3) preparation of parahydroxyben-zaldehyde: in 4~8 DEG C of low temperature environment, to intermediate II, the first obtained in step 2)
It is passed through 60~78% sulfuric acid solution in the mixed solution of alcoholic solution and (NH3) H2O, while being passed through sulfuric acid solution lateral dominance with stirring
It mixes device and stirs 2~4h of the mixed solution, obtain the mixing of parahydroxyben-zaldehyde, sulfuric acid, methanol solution and (NH3) H2O
Solution.
4) removal of impurities of parahydroxyben-zaldehyde solution: by step 3) parahydroxyben-zaldehyde, sulfuric acid, methanol solution and
(NH3) mixed solution of H2O is heated to 72~82 DEG C, and after stirring 70~90min, methanol solution volatilizees completely to be obtained to hydroxyl
The mixed solution of benzaldehyde, sulfuric acid and (NH3) H2O is passed through in 92~98% C2H2O6 solution into the solution, is utilized
20~30min is mixed in agitating device, is subsequently placed in 4~8 DEG C of low temperature environment, stands 60~80min, has been layered to it
Entirely, upper layer (NH3) H2O and sulfuric acid solution are toppled over into discharge, leaves parahydroxyben-zaldehyde and the mixed liquor of C2H2O6.
5) purification of parahydroxyben-zaldehyde solution: the mixed liquor that step 4) obtains parahydroxyben-zaldehyde and C2H2O6 is placed in
3~6h in fractionating column, C2H2O6 volatilize completely obtains the parahydroxyben-zaldehyde solution of high-purity.
Further, the oxygen being passed through in the step 2) is at least 12~16 times of intermediate compound I molal weight.
Further, the molar ratio of the concentrated sulfuric acid being passed through and intermediate II is 2:1 in the step 3).
Further, the step 1), step 2), step 3), the mixing speed of agitating device in step 4) are 25-
50r/min
Further, the methanol in step (2) is the aqueous solution that concentration is not less than 75%, and the sodium hydroxide is concentration
Aqueous solution or sodium hydrate particle not less than 80%.
Realize the chemical equation of above-mentioned synthesis parahydroxyben-zaldehyde are as follows:
The utility model has the advantages that compared with prior art, the present invention has the advantage that
Synthesis technology simple specification of the present invention, production technology and production procedure are easily grasped, and are being effectively raised to hydroxyl
While benzaldehyde production job specification, the utilization rate to p-methyl phenol raw material is effectively raised, passes through a water
Ammonia is closed as the reactant with p-methyl phenol raw material, not only p-methyl phenol reaction is more rapid, more sufficiently, and reacts
Generating afterwards is that ammonium sulfate impurity is more easy to handle, and the purification of parahydroxyben-zaldehyde is increased in the preparation process of parahydroxyben-zaldehyde
Technique can effectively improve the purity for the parahydroxyben-zaldehyde prepared.
Detailed description of the invention
Fig. 1 is process flow chart of the invention.
Specific embodiment
According to following embodiments, the present invention may be better understood.However, as it will be easily appreciated by one skilled in the art that real
It applies content described in example and is merely to illustrate the present invention, without sheet described in detail in claims should will not be limited
Invention.
Embodiment 1
A kind of preparation method of parahydroxyben-zaldehyde as shown in Figure 1, includes the following steps:
1) preparation of intermediate compound I: p-methyl phenol solution is placed in quartz reaction kettle, is then added to quartz reaction kettle
Excessive 50~64% (NH3) H2O solution and suitable catalyzed methanol solution for reaction, maintains the temperature at
In 8~16 DEG C, under strong illumination, be stirred 70~90min using agitating device, obtain intermediate compound I, methanol solution and
(NH3) mixed solution of H2O.
2) mixed solution of intermediate compound I, methanol solution and (NH3) H2O the preparation of intermediate II: are obtained to step 1)
In be continually fed into concentration be 90~98% oxygen, stir mixed solution 2h with agitating device while being passed through oxygen lateral dominance, obtain
Obtain the mixed solution of intermediate II, methanol solution and (NH3) H2O.
3) preparation of parahydroxyben-zaldehyde: in 4~8 DEG C of low temperature environment, to intermediate II, the first obtained in step 2)
It is passed through 60~78% sulfuric acid solution in the mixed solution of alcoholic solution and (NH3) H2O, while being passed through sulfuric acid solution lateral dominance with stirring
It mixes device and stirs mixed solution 2h, the mixing for obtaining parahydroxyben-zaldehyde, sulfuric acid, methanol solution and (NH3) H2O is molten
Liquid.
4) removal of impurities of parahydroxyben-zaldehyde solution: by step 3) parahydroxyben-zaldehyde, sulfuric acid, methanol solution and
(NH3) mixed solution of H2O is heated to 72~82 DEG C, and after stirring 70~90min, methanol solution volatilizees completely to be obtained to hydroxyl
The mixed solution of benzaldehyde, sulfuric acid and (NH3) H2O is passed through in 92~98% C2H2O6 solution into the solution, is utilized
20~30min is mixed in agitating device, is subsequently placed in 4~8 DEG C of low temperature environment, stands 60~80min, has been layered to it
Entirely, upper layer (NH3) H2O and sulfuric acid solution are toppled over into discharge, leaves parahydroxyben-zaldehyde and the mixed liquor of C2H2O6.
5) purification of parahydroxyben-zaldehyde solution: the mixed liquor that step 4) obtains parahydroxyben-zaldehyde and C2H2O6 is placed in
3h in fractionating column, C2H2O6 volatilize completely obtains the parahydroxyben-zaldehyde solution of high-purity.
In the present embodiment, the oxygen being passed through in the step 2) is at least 12 times of intermediate compound I molal weight.
In the present embodiment, the molar ratio of the concentrated sulfuric acid and intermediate II that are passed through in the step 3) is 2:1.
In the present embodiment, the step 1), step 2), step 3), the mixing speed of agitating device in step 4) are
30r/min。
In the present embodiment, the methanol in step (2) is the aqueous solution that concentration is not less than 75%, and the sodium hydroxide is dense
Degree is not less than 80% aqueous solution or sodium hydrate particle.
Embodiment 2
Such as a kind of preparation method of parahydroxyben-zaldehyde of Fig. 1 comprising following steps:
(1) preparation of intermediate compound I: p-methyl phenol solution is placed in quartz reaction kettle, is then added to quartz reaction kettle
Enter excessive 50~64% (NH3) H2O solution and suitable catalyzed methanol solution for reaction, keeps temperature
In 8~16 DEG C, under strong illumination, be stirred 70~90min using agitating device, obtain intermediate compound I, methanol solution with
And the mixed solution of (NH3) H2O.
2) mixed solution of intermediate compound I, methanol solution and (NH3) H2O the preparation of intermediate II: are obtained to step 1)
In be continually fed into concentration be 90~98% oxygen, stir mixed solution 3h with agitating device while being passed through oxygen lateral dominance, obtain
Obtain the mixed solution of intermediate II, methanol solution and (NH3) H2O.
3) preparation of parahydroxyben-zaldehyde: in 4~8 DEG C of low temperature environment, to intermediate II, the first obtained in step 2)
It is passed through 60~78% sulfuric acid solution in the mixed solution of alcoholic solution and (NH3) H2O, while being passed through sulfuric acid solution lateral dominance with stirring
It mixes device and stirs mixed solution 3h, the mixing for obtaining parahydroxyben-zaldehyde, sulfuric acid, methanol solution and (NH3) H2O is molten
Liquid.
4) removal of impurities of parahydroxyben-zaldehyde solution: by step 3) parahydroxyben-zaldehyde, sulfuric acid, methanol solution and
(NH3) mixed solution of H2O is heated to 72~82 DEG C, and after stirring 70~90min, methanol solution volatilizees completely to be obtained to hydroxyl
The mixed solution of benzaldehyde, sulfuric acid and (NH3) H2O is passed through in 92~98% C2H2O6 solution into the solution, is utilized
20~30min is mixed in agitating device, is subsequently placed in 4~8 DEG C of low temperature environment, stands 60~80min, has been layered to it
Entirely, upper layer (NH3) H2O and sulfuric acid solution are toppled over into discharge, leaves parahydroxyben-zaldehyde and the mixed liquor of C2H2O6.
5) purification of parahydroxyben-zaldehyde solution: the mixed liquor that step 4) obtains parahydroxyben-zaldehyde and C2H2O6 is placed in
4h in fractionating column, C2H2O6 volatilize completely obtains the parahydroxyben-zaldehyde solution of high-purity.
In the present embodiment, the oxygen being passed through in the step 2) is at least 14 times of intermediate compound I molal weight.
In the present embodiment, the molar ratio of the concentrated sulfuric acid and intermediate II that are passed through in the step 3) is 2:1.
In the present embodiment, the step 1), step 2), step 3), the mixing speed of agitating device in step 4) are
40r/min
In the present embodiment, the methanol in step (2) is the aqueous solution that concentration is not less than 75%, and the sodium hydroxide is dense
Degree is not less than 80% aqueous solution or sodium hydrate particle.
Embodiment 3
As shown in Figure 1, a kind of preparation method of parahydroxyben-zaldehyde, includes the following steps:
1) preparation of intermediate compound I: p-methyl phenol solution is placed in quartz reaction kettle, is then added to quartz reaction kettle
Excessive 50~64% (NH3) H2O solution and suitable catalyzed methanol solution for reaction, maintains the temperature at
In 8~16 DEG C, under strong illumination, be stirred 70~90min using agitating device, obtain intermediate compound I, methanol solution and
(NH3) mixed solution of H2O.
2) mixed solution of intermediate compound I, methanol solution and (NH3) H2O the preparation of intermediate II: are obtained to step 1)
In be continually fed into concentration be 90~98% oxygen, stir mixed solution 2.5h with agitating device while being passed through oxygen lateral dominance,
Obtain the mixed solution of intermediate II, methanol solution and (NH3) H2O.
3) preparation of parahydroxyben-zaldehyde: in 4~8 DEG C of low temperature environment, to intermediate II, the first obtained in step 2)
It is passed through 60~78% sulfuric acid solution in the mixed solution of alcoholic solution and (NH3) H2O, while being passed through sulfuric acid solution lateral dominance with stirring
It mixes device and stirs mixed solution 2.5h, the mixing for obtaining parahydroxyben-zaldehyde, sulfuric acid, methanol solution and (NH3) H2O is molten
Liquid.
4) removal of impurities of parahydroxyben-zaldehyde solution: by step 3) parahydroxyben-zaldehyde, sulfuric acid, methanol solution and
(NH3) mixed solution of H2O is heated to 72~82 DEG C, and after stirring 70~90min, methanol solution volatilizees completely to be obtained to hydroxyl
The mixed solution of benzaldehyde, sulfuric acid and (NH3) H2O is passed through in 92~98% C2H2O6 solution into the solution, is utilized
20~30min is mixed in agitating device, is subsequently placed in 4~8 DEG C of low temperature environment, stands 60~80min, has been layered to it
Entirely, upper layer (NH3) H2O and sulfuric acid solution are toppled over into discharge, leaves parahydroxyben-zaldehyde and the mixed liquor of C2H2O6.
5) purification of parahydroxyben-zaldehyde solution: the mixed liquor that step 4) obtains parahydroxyben-zaldehyde and C2H2O6 is placed in
3.5h in fractionating column, C2H2O6 volatilize completely obtains the parahydroxyben-zaldehyde solution of high-purity.
In the present embodiment, the oxygen being passed through in the step 2) is at least 15 times of intermediate compound I molal weight.
In the present embodiment, the molar ratio of the concentrated sulfuric acid and intermediate II that are passed through in the step 3) is 2:1.
In the present embodiment, the step 1), step 2), step 3), the mixing speed of agitating device in step 4) are
50r/min
In the present embodiment, the methanol in step (2) is the aqueous solution that concentration is not less than 75%, and the sodium hydroxide is dense
Degree is not less than 80% aqueous solution or sodium hydrate particle.
The utility model has the advantages that compared with prior art, the present invention has the advantage that
Synthesis technology simple specification of the present invention, production technology and production procedure are easily grasped, and are being effectively raised to hydroxyl
While benzaldehyde production job specification, the utilization rate to p-methyl phenol raw material is effectively raised, passes through a water
Ammonia is closed as the reactant with p-methyl phenol raw material, not only p-methyl phenol reaction is more rapid, more sufficiently, and reacts
Generating afterwards is that ammonium sulfate impurity is more easy to handle, and the purification of parahydroxyben-zaldehyde is increased in the preparation process of parahydroxyben-zaldehyde
Technique can effectively improve the purity for the parahydroxyben-zaldehyde prepared.
The above shows and describes the basic principles and main features of the present invention and the advantages of the present invention.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
Claims (4)
1. the preparation method of kind of parahydroxyben-zaldehyde, which is characterized in that the preparation method of the parahydroxyben-zaldehyde includes such as
Lower step:
The preparation of intermediate compound I: p-methyl phenol solution is placed in quartz reaction kettle, is then added to quartz reaction kettle excessive
For 50~64% (NH3) the H2O solution and suitable catalyzed methanol solution of reaction, 8~16 are maintained the temperature at
In DEG C, under strong illumination, be stirred 70~90min using agitating device, obtain intermediate compound I, methanol solution and
(NH3) mixed solution of H2O；
The preparation of intermediate II: it obtains in the mixed solution of intermediate compound I, methanol solution and (NH3) H2O to step 1) to hold
The continuous concentration that is passed through is 90~98% oxygen, 2-4h of the mixed solution is stirred with agitating device while being passed through oxygen lateral dominance, in acquisition
The mixed solution of mesosome II, methanol solution and (NH3) H2O；
The preparation of parahydroxyben-zaldehyde: in 4~8 DEG C of low temperature environment, the intermediate II that is obtained into step 2, methanol solution
And it is passed through 60~78% sulfuric acid solution in the mixed solution of (NH3) H2O, while being passed through sulfuric acid solution lateral dominance agitating device
2~4h of the mixed solution is stirred, the mixed solution of parahydroxyben-zaldehyde, sulfuric acid, methanol solution and (NH3) H2O are obtained；
The removal of impurities of parahydroxyben-zaldehyde solution: by parahydroxyben-zaldehyde, sulfuric acid, methanol solution and (NH3) in step 3)
The mixed solution of H2O is heated to 72~82 DEG C, after stirring 70~90min, methanol solution volatilize completely obtain parahydroxyben-zaldehyde,
The mixed solution of sulfuric acid and (NH3) H2O is passed through in 92~98% C2H2O6 solution into the solution, is filled using stirring
20~30min of mixing is set, is subsequently placed in 4~8 DEG C of low temperature environment, 60~80min is stood, it completely to its layering, will
Upper layer (NH3) H2O and sulfuric acid solution topple over discharge, leave parahydroxyben-zaldehyde and the mixed liquor of C2H2O6；
The purification of parahydroxyben-zaldehyde solution: the mixed liquor that step 4) obtains parahydroxyben-zaldehyde and C2H2O6 is placed in fractionating column
Interior 3~6h, C2H2O6 volatilize completely obtains the parahydroxyben-zaldehyde solution of high-purity.
2. according to preparation method described in claim 1, which is characterized in that the oxygen being passed through in the step 2 is at least intermediate
12~16 times of I molal weight.
3. according to preparation method described in claim 1, which is characterized in that the concentrated sulfuric acid and intermediate II being passed through in the step 3)
Molar ratio be 2:1.
4. according to preparation method described in claim 1, which is characterized in that the step 1), step 2, step 3), in step 4)
Agitating device mixing speed be 25-50r/min.
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| CN102531860A (en) * | 2011-12-29 | 2012-07-04 | 衢州学院 | Method for catalyzing oxosynthesis of parahydroxyben-zaldehyde by using stratified material |
| CN105820042A (en) * | 2016-02-03 | 2016-08-03 | 嘉兴市金利化工有限责任公司 | Production technology of p-hydroxy benzaldehyde and production system thereof |
| CN106554256A (en) * | 2016-06-27 | 2017-04-05 | 宁夏海诚电化信息科技有限公司 | A kind of hydroxy benzaldehyde production technology |
| CN106986755A (en) * | 2017-05-11 | 2017-07-28 | 杭州师范大学 | A kind of method that photocatalysis prepares parahydroxyben-zaldehyde |
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2018
- 2018-07-16 CN CN201810774561.5A patent/CN109180454A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101462933A (en) * | 2009-01-14 | 2009-06-24 | 中北大学 | Method and equipment for synthesizing p-hydroxybenzene formaldehyde by catalytic oxidation |
| CN102115435A (en) * | 2010-01-04 | 2011-07-06 | 张大男 | Synthesis method of parahydroxybenzaldehyde |
| CN102531860A (en) * | 2011-12-29 | 2012-07-04 | 衢州学院 | Method for catalyzing oxosynthesis of parahydroxyben-zaldehyde by using stratified material |
| CN105820042A (en) * | 2016-02-03 | 2016-08-03 | 嘉兴市金利化工有限责任公司 | Production technology of p-hydroxy benzaldehyde and production system thereof |
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Application publication date: 20190111 |