CN117902968A - Preparation method of alpha-hexyl cinnamaldehyde - Google Patents
Preparation method of alpha-hexyl cinnamaldehyde Download PDFInfo
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- CN117902968A CN117902968A CN202311730976.XA CN202311730976A CN117902968A CN 117902968 A CN117902968 A CN 117902968A CN 202311730976 A CN202311730976 A CN 202311730976A CN 117902968 A CN117902968 A CN 117902968A
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- octanal
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- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 title claims abstract description 24
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000001414 (2E)-2-(phenylmethylidene)octanal Substances 0.000 title claims abstract description 22
- 229940072717 alpha-hexylcinnamaldehyde Drugs 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims abstract description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000011084 recovery Methods 0.000 claims abstract description 4
- 238000004821 distillation Methods 0.000 claims abstract description 3
- 239000012046 mixed solvent Substances 0.000 claims description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 239000012071 phase Substances 0.000 claims description 18
- 239000012074 organic phase Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 230000001502 supplementing effect Effects 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 18
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 10
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of organic synthesis, and particularly discloses a preparation method of alpha-hexyl cinnamaldehyde; under the protection of nitrogen, tertiary butanol, ethanol and water are used as solvents, potassium hydroxide and PEG-400 are used as catalysts, benzaldehyde and n-octanal are used for reaction for 6 hours at 60 ℃, and then the fractions at 175-176 ℃ are obtained after extraction, acidolysis, solvent recovery, drying and reduced pressure distillation. According to the invention, tertiary butanol is added in the solvent, so that the condensation of n-octyl aldehyde and the product alpha-hexyl cinnamaldehyde can be effectively prevented due to the steric hindrance effect, and the synthesis yield is effectively improved; the invention can recycle the water phase in the solvent and the water phase in the acidolysis solution through process adjustment, thereby greatly reducing the discharge of wastewater.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of alpha-hexyl cinnamaldehyde.
Background
Alpha-hexyl cinnamaldehyde has fresh and sweet jasmine fragrance and is widely applied to the food and cosmetic industry. Ding Desheng et al, incorporated by reference, "practical synthetic fragrances", and methods for their synthesis are described in Shanghai science and technology Press, 1991. The method uses potassium hydroxide as a catalyst and ethanol as a solvent to synthesize the alpha-hexyl cinnamaldehyde, but the yield is only about 40 percent.
Disclosure of Invention
The invention provides a preparation method of alpha-hexyl cinnamaldehyde, which can improve the yield, and the water phase in the synthesis process can be recycled, so that the discharge of waste liquid is reduced.
In order to achieve the above object, the present invention adopts the following technical scheme: the preparation method of the alpha-hexyl cinnamaldehyde comprises the following steps:
s1, uniformly mixing a mixed solvent containing tertiary butanol, ethanol and water with a catalyst, heating, adding benzaldehyde, and dropwise adding n-octanal for reaction;
S2, cooling the reaction liquid, standing for liquid separation, extracting an organic phase in an aqueous phase, combining the organic phases, adding acid liquor, and recycling an organic solvent during acidolysis;
S3, cooling the feed liquid after recovering the organic solvent, standing for liquid separation, extracting an organic phase in an aqueous phase, combining the organic phases, performing drying treatment, performing reduced pressure distillation (the pressure is 2x10 3 Pa), and collecting a fraction at 175-176 ℃ to obtain the alpha-hexyl cinnamaldehyde.
Further, tertiary butanol, ethanol and water in the S1 are mixed according to a volume ratio of 1:1-3:2-4; the catalyst is formed by mixing PEG-400 and KOH according to the mass ratio of 1:1.3.
Further, the mass ratio of benzaldehyde to n-octanal in S1 is 1:1.1; the weight ratio of n-octanal to the solvent is 1:3-5; the weight ratio of the catalyst to the mixed solvent is 1:7-1:9.
Further, the solvent and the catalyst in S1 are heated to 60 ℃ after being uniformly mixed, and the reaction temperature in S1 is 60 ℃ for 6 hours.
Further, the extractant in S2 and S3 is diethyl ether; the acid liquor in S2 is dilute sulfuric acid, and the pH value is adjusted to 2-3 by adding the dilute sulfuric acid during acidolysis.
Further, the mass concentration of the dilute sulfuric acid was 0.8%.
Further, the extractant diethyl ether is recovered in S2 at a temperature between 30 and 45 ℃, and ethanol and tertiary butanol are recovered at a temperature between 45 and 95 ℃. The recovered tertiary butanol and ethanol are combined with the aqueous phase after separation in S2.
Further, the water phase separated in the step S2 is supplemented with corresponding components and then circularly sleeved in the step S1 to serve as a solvent and a catalyst.
Further, the water phase separated in the step S3 is circularly sleeved in the acid liquor of the step S2 after supplementing corresponding components.
Further, the organic phase in S3 was dried with a molecular sieve and distilled under reduced pressure of 2X10 3 Pa.
The invention has the following beneficial effects:
1. according to the invention, tertiary butanol is added in the solvent, so that the condensation of n-octyl aldehyde and the product alpha-hexyl cinnamaldehyde can be effectively prevented due to the steric hindrance effect, the synthesis yield can be effectively improved, and obvious economic benefits can be brought to enterprises.
2. According to the invention, after the reaction is finished, the water phase is separated out, sulfuric acid is added for acidolysis, the separated water phase can be recycled, and the water phase after sulfuric acid acidolysis is added in the later stage can be recycled, so that the discharge of wastewater is greatly reduced.
3. The invention can recycle the solvent during acidolysis, thereby reducing energy consumption.
4. The synthesis method provided by the invention is simple and convenient to operate, does not need complex production equipment, has low investment and high recovery rate, and is suitable for industrial production.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention.
All n-octanal in the following examples had a purity of 95% and benzaldehyde had a purity of 99.9%.
Example 1
The preparation method of the alpha-hexyl cinnamaldehyde comprises the following specific steps:
The reactor was purged with nitrogen, air was purged from the reactor, 5400g of the mixed solvent (t-butanol, ethanol, water in a volume ratio of 1:2:3) and 678g of the catalyst (PEG-400 to KOH in a mass ratio of 1:1.3) were added to the reactor, and stirring was started. The temperature was raised to 60℃and 1166.15g of benzaldehyde was added thereto, followed by dropwise addition of 10mol of n-octanal (1349.68 g, completed in 40 minutes) with stirring. The temperature was kept at 60℃and the reaction was continued with stirring for 6 hours. Regulating the temperature of the circulating water to 30 ℃, stirring and cooling to below 40 ℃, stopping stirring, standing and separating liquid.
Extracting the water phase with 1/2 volume diethyl ether for 3 times to obtain water phase A, mixing the extracted organic phases with the organic phase A to obtain camera A, and adding 0.8% dilute sulfuric acid under stirring to pH value of 3.
Heating to about 100deg.C, respectively collecting diethyl ether at 30-45deg.C and solvent (tert-butanol and ethanol) at 45-95deg.C under stirring; continuously stirring and refluxing for 30min, regulating the temperature of a circulating pump to 30 ℃, stirring and cooling to below 40 ℃, stopping stirring, standing, separating liquid, extracting the water phase with diethyl ether for 3 times to obtain a water phase B, combining the organic phases to obtain the organic phase B, drying the organic phase B with a molecular sieve, and distilling under reduced pressure (2 x10 3 Pa) to collect fractions at 175-176 ℃ to obtain 1817.0g of alpha-hexyl cinnamaldehyde, wherein the yield is 84%, and the content is 95.2%.
Example 2
The same as in example 1, but wherein the amount of n-octanal is 1mol, the weight ratio of the catalyst to the mixed solvent is 1:7; the mixed solvent is formed by mixing tert-butanol, ethanol and water according to the volume ratio of 1:1:2, and the weight ratio of n-octanal to the mixed solvent is 1:3.
To obtain 166.57g of alpha-hexyl cinnamaldehyde, the yield is 77 percent, and the content is 95.1 percent.
Example 3
The same as in example 1, but wherein the amount of n-octanal is 0.5mol, the weight ratio of the catalyst to the mixed solvent is 1:9; the mixed solvent is formed by mixing tert-butanol, ethanol and water according to the volume ratio of 1:3:4, and the weight ratio of n-octanal to the mixed solvent is 1:5.
87.61G of alpha-hexyl cinnamaldehyde is obtained, the yield is 81.0 percent, and the content is 95.3 percent.
Example 4
As in example 1, the amount of n-octanal is 20mol; the weight ratio of the catalyst to the mixed solvent is 1:8; the mixed solvent is formed by mixing tertiary butanol, ethanol and water according to the volume ratio of 1:2:3; the weight ratio of the n-octanal to the mixed solvent is 1:4.
To obtain 3625.09g of alpha-hexyl cinnamaldehyde, the yield is 83.79 percent, and the content is 94.9 percent.
Example 5
As in example 1, the amount of n-octanal is 0.2mol, and the weight ratio of the catalyst to the mixed solvent is 1:8; the mixed solvent is formed by mixing tertiary butanol, ethanol and water according to the volume ratio of 1:2:3; the weight ratio of the n-octanal to the mixed solvent is 1:4. The yields of α -hexyl cinnamic aldehyde are shown in Table 1.
The aqueous phase A and the aqueous phase B of this example were recycled. Adding ethanol, tertiary butanol, potassium hydroxide and PEG-400 into the water phase A until the corresponding content (namely, the weight ratio of the mixed solvent to the catalyst is 8:1, the volume ratio of the tertiary butanol, the ethanol and the water in the mixed solvent is 1:2:3, and the weight ratio of the PEG-400 to the KOH in the catalyst is 1:1.3), and recycling the water phase A; and the water phase B is supplemented with concentrated sulfuric acid until the sulfuric acid content is 0.8%, and the concentrated sulfuric acid is recycled. The results of recycling the multi-time recovery are shown in the following table 1.
TABLE 1
As can be seen from Table 1, after 7 applications of the aqueous phase, the yield of α -hexyl cinnamaldehyde was not affected.
Comparative example 1:
The same as in example 1, but wherein the amount of n-octanal is 0.1mol, the weight ratio of the catalyst to the mixed solvent is 1:8; the mixed solvent is formed by mixing ethanol and water according to the volume ratio of 1:1, and the weight ratio of n-octanal to the mixed solvent is 1:4.
8.70G of alpha-hexyl cinnamaldehyde is obtained, and the yield is 40.2%.
Comparative example 2
The same as in example 1, but wherein the amount of n-octanal is 0.1mol, the weight ratio of the catalyst to the mixed solvent is 1:8; the mixed solvent is formed by mixing isobutanol, ethanol and water according to the volume ratio of 1:2:3, and the weight ratio of n-octanal to the mixed solvent is 1:4.
10.37G of alpha-hexyl cinnamic aldehyde is obtained, and the yield is 47.9 percent.
Comparative example 3
The same as in example 1, but wherein the amount of n-octanal is 0.1mol, the weight ratio of the catalyst to the mixed solvent is 1:8; the mixed solvent is formed by mixing tert-amyl alcohol, ethanol and water according to the volume ratio of 1:2:3, and the weight ratio of n-octyl aldehyde to the mixed solvent is 1:4.
13.83G of alpha-hexyl cinnamaldehyde is obtained, and the yield is 63.9%.
As can be seen from the comparative example, when there is no t-butanol in the reaction system, the yield is greatly reduced; when tert-butanol is exchanged for isobutanol or tert-amyl alcohol, which have a steric effect, the yield is significantly reduced. It is shown that tertiary butanol can be used in the reaction system to achieve the best effect.
The above examples describe preferred embodiments of the present invention, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (10)
1. The preparation method of the alpha-hexyl cinnamaldehyde is characterized by comprising the following steps of:
s1, uniformly mixing a mixed solvent containing tertiary butanol, ethanol and water with a catalyst, heating, adding benzaldehyde, and dropwise adding n-octanal for reaction;
S2, cooling the reaction liquid, standing for liquid separation, extracting an organic phase in an aqueous phase, combining the organic phases, adding acid liquor, and recycling an organic solvent during acidolysis;
S3, cooling the feed liquid after the recovery of the organic solvent, standing for liquid separation, extracting an organic phase in an aqueous phase, combining the organic phases for drying treatment, and then carrying out reduced pressure distillation to obtain the alpha-hexyl cinnamaldehyde.
2. The method of manufacturing according to claim 1, characterized in that: the tertiary butanol, ethanol and water in the S1 are mixed according to the volume ratio of 1:1-3:2-4; the catalyst is formed by mixing PEG-400 and KOH according to the mass ratio of 1:1.3.
3. The method of manufacturing according to claim 1, characterized in that: the weight ratio of the catalyst to the mixed solvent in the step S1 is 1:7-1:9; the weight ratio of n-octanal to the solvent is 1:3-5; the mass ratio of the benzaldehyde to the n-octanal is 1:1.1.
4. The preparation method according to any one of claims 1 to 3, characterized in that: and (2) uniformly mixing the solvent and the catalyst in the step S1, and heating to 60 ℃, wherein the reaction temperature in the step S1 is 60 ℃ and the time is 6 hours.
5. The method of manufacturing according to claim 1, characterized in that: the extractant in S2 and S3 is diethyl ether; the acid liquor in S2 is dilute sulfuric acid, and the pH value is adjusted to 2-3 by adding the dilute sulfuric acid during acidolysis.
6. The method of manufacturing according to claim 5, wherein: the mass concentration of the dilute sulfuric acid is 0.8%.
7. The method of manufacturing according to claim 5, wherein: s2, recovering extractant diethyl ether at 30-45 ℃ and recovering tertiary butanol and ethanol at 45-95 ℃; and (3) mixing the recovered tertiary butanol and ethanol with the water phase separated in the step S2 for recycling.
8. The method of manufacturing according to claim 1, characterized in that: and S2, supplementing corresponding components to the water phase after the liquid separation in the step S2, and circularly sleeving the water phase in the step S1.
9. The method of manufacturing according to claim 8, wherein: and S3, supplementing corresponding components into the water phase after the liquid separation in the step S2, and circularly sleeving the water phase into the acid liquid in the step S.
10. The method of manufacturing according to claim 1, characterized in that: and S3, drying the organic phase by using a molecular sieve, distilling under reduced pressure, wherein the pressure is 2x10 3 Pa, and collecting fractions at 175-176 ℃ to obtain the alpha-hexyl cinnamaldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311730976.XA CN117902968A (en) | 2023-12-15 | 2023-12-15 | Preparation method of alpha-hexyl cinnamaldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311730976.XA CN117902968A (en) | 2023-12-15 | 2023-12-15 | Preparation method of alpha-hexyl cinnamaldehyde |
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| CN117902968A true CN117902968A (en) | 2024-04-19 |
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| CN202311730976.XA Pending CN117902968A (en) | 2023-12-15 | 2023-12-15 | Preparation method of alpha-hexyl cinnamaldehyde |
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- 2023-12-15 CN CN202311730976.XA patent/CN117902968A/en active Pending
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