CN105198720A - Production line for synthesizing raspberry ketone from natural equivalent anisic aldehyde - Google Patents
Production line for synthesizing raspberry ketone from natural equivalent anisic aldehyde Download PDFInfo
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- CN105198720A CN105198720A CN201510716600.2A CN201510716600A CN105198720A CN 105198720 A CN105198720 A CN 105198720A CN 201510716600 A CN201510716600 A CN 201510716600A CN 105198720 A CN105198720 A CN 105198720A
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- raspberry ketone
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- anisic aldehyde
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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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Abstract
The invention discloses a production line for synthesizing raspberry ketone from a natural equivalent anisic aldehyde. The production line comprises, sequentially connected, a raw material storage tank, a condensation reaction kettle, a hydrogenation reaction kettle, a demethylating reaction kettle, a crude raspberry ketone distillation and collection tower, a primary crystallization tank, a re-crystallization tank, a centrifuge and a drying and crushing system. The final product is obtained through the following steps: allowing anisic aldehyde to go through the condensation reaction kettle and the hydrogenation reaction kettle, carrying out a demethylating reaction to obtain crude raspberry ketone, directly transferring the crude raspberry ketone to a crude raspberry ketone distillation and collection tower, carrying out primary crystallization, allowing the primary crystallized material to go through the re-crystallization tank, centrifuging, and drying, and the synthesis time shortens to 2d from original 4d. The reaction time is short, so the production line has the advantages of few byproducts and high total yield.
Description
Technical field
The present invention relates to the production line of spices, be specifically related to a kind of production line being synthesized raspberry ketone by natural equivalent anisic aldehyde.
Background technology
Raspberry ketone is the main aromatic components of Fructus Rubi, there is the fragrant fragrance of characteristic hesperidium and the fragrance of Fructus Rubi, the spices of a large amount of a kind of quiet and tastefully laid out fruital used both at home and abroad, be widely used in makeup and food, but also for the synthesis of medicine, dyestuff, this is external is agriculturally a kind of attractant.Because its fragrance is excellent, large usage quantity, price is higher, so the research of various countries to raspberry ketone and analogue thereof is all paid much attention to.Because its content in raspberry is extremely low, this just determine be difficult to from Fructus Rubi isolated go out raspberry ketone, raspberry ketone in the middle of existing obtains mainly through synthesizing, its synthetic method mainly contains following 4 kinds, as adopted the synthetic method etc. of the synthetic method of phenol and methyl vinyl ketone, phenol and butanolone.
(1) synthetic route of phenol and methyl vinyl ketone, in O ~ 3 DEG C, carries out alkylated reaction under strong acid catalyst, reacts about 2 hours.Be neutralized to certain DH value with alkali, then through extraction, underpressure distillation, the operation such as recrystallization obtains raspberry ketone product, and yield is 69%.The raw material methyl vinyl ketone preparation used in this technique is comparatively complicated, and toxicity is larger.Phenol and methyl vinyl ketone carry out alkylation, and traditional technology uses the strong acid such as phosphoric acid, sulfuric acid as catalyzer, also can bring the problem such as environmental pollution and equipment corrosion.
(2) synthetic route of phenol and butanolone, this operational path is using phenol and 4-butanols-2-ketone as raw material, under acid catalysis, carry out alkylated reaction.Use raw material butanol ketone, the methyl vinyl ketone using toxicity larger can be avoided.But the volatile water of 4-butanols-2-ketone generates ethylene methacrylic ketone, can produce resinoid by product in reaction.And this reaction also will be carried out under strong acid and cold condition, there is the problems such as equipment corrosion, environmental pollution and aftertreatment difficulty equally.At the water-soluble acid as catalyst of use, yield is 45 ~ 62%, and uses cation exchange resin as catalyst, and yield is 67 ~ 70%.
(3) to the synthetic route of methoxy-benzyl chlorine and methyl aceto acetate, this route be by methyl aceto acetate p-methoxybenzyl chloride a-alkyl replace after, carry out keto-acid decomposition and obtain 4-p-methoxyphenyl .2. butanone ether bond rupture under concentrated hydrobromic acid effect, finally generate 4-(4-hydroxyphenyl)-2-butanone, yield is 63%.Under Hydrogen bromide effect, methoxyl group fracture not exclusively, makes to isolate raspberry ketone very difficult.In addition, Hydrogen bromide needs expensive instrument with being separated of bromoalkane.
(4) p-Hydroxybenzaldehyde and acetone carry out Claisen-Schrnidt condensation, the synthetic route of hydrogenating reduction, this operational path carries out Claisen-Schmidt condensation with p-Hydroxybenzaldehyde and acetone, then hydrogenating reduction, then the raspberry ketone obtaining desired purity through the aftertreatment such as underpressure distillation and recrystallization.The feature of this technique is that product yield is high, and aroma quality is good, sufficient raw.But a large amount of alkali, acid to be used in this synthesis, the problem such as equipment corrosion, contaminate environment can be brought.
The technique of above-mentioned synthesis raspberry ketone, or there is environmental pollution problem, or there is toxic side effect, or there is the low defect of yield.
Summary of the invention
Technical problem to be solved by this invention is to provide the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde that a kind of yield is high, the reaction times is short.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows:
A kind of production line being synthesized raspberry ketone by natural equivalent anisic aldehyde, comprise material storaging tank, also comprise the condensation reaction still, hydrogenation reaction cauldron, alcohol recycle distillation tower, demethylating reaction still, primary crystallization tank, recrystallization tank, whizzer and the drying and crushing system that connect successively, the outlet of described material storaging tank is connected with the import of condensation reaction still.
Such scheme is preferred, is also connected with p-methoxy benzyl acetone and hangs white oil reaction unit between hydrogenation reaction cauldron and demethylating reaction still.Hang white oil reaction unit at p-methoxy benzyl acetone and add acetic acid dilution, the reaction times (reaction times shortened to 3 hours from original 24 hours) of demethylation process can be shortened greatly, reduce the generation of byproduct simultaneously.
Such scheme is preferred, hangs between white oil reaction unit be also connected with hay tank at hydrogenation reaction cauldron and p-methoxy benzyl acetone.Catalyzer in the recyclable hydrogenation of filtration unit, such process can reduce the waste of material, reduces production cost.
Such scheme is preferred, and the outlet of described hay tank is also connected with the import of hydrogenation reaction cauldron, and the outlet of alcohol recycle distillation tower is also connected with the import of hydrogenation reaction cauldron.The catalyzer reclaimed and alcohol are sent in hydrogenation reaction cauldron and are directly utilized.
Such scheme is preferred, collects between tower be connected with acid recovery distillation tower at demethylating reaction still and thick raspberry ketone distillation, and white oil reaction unit is also hung in the outlet of acid recovery distillation tower import with p-methoxy benzyl acetone is connected.
Such scheme is preferred, is also connected with the thick oily reaction unit of methylene acetone between condensation reaction still and hydrogenation reaction cauldron.
Such scheme is preferred, between condensation reaction still and the thick oily reaction unit of methylene acetone, be also connected with thick oil wash neutralising arrangement and solvent recuperation distillation tower in turn.
Such scheme is preferred, and the outlet of described solvent recuperation distillation tower is also connected with the import of thick oil wash neutralising arrangement.The toluene that solvent recuperation distillation tower is regained directly sends into thick oil wash neutralising arrangement as thinner, reaches the object of workout cost.
Such scheme is preferred, between condensation reaction still and thick oil wash neutralising arrangement, be also connected with stratification device.
Such scheme is preferred, is also connected with the distillation of thick raspberry ketone and collects tower between demethylating reaction still and primary crystallization tank.
Compared with prior art, production line of the present invention, from condensation reaction still, hydrogenation reaction cauldron, then after demethylating reaction obtains thick raspberry ketone, directly arrive the distillation of thick raspberry ketone and collect tower, then carry out primary crystallization, recrystallization tank, centrifugal and drying obtain the finished product, single sintering gets off, and the time shortened to 2 days from original 4 days, and due to the reaction times short, by product is few, and total recovery is high; In addition, whole production line has overlaps retrieving arrangement more, and as solvent recuperation distillation tower, hay tank etc., the material of recovery is directly sent in corresponding reaction unit by it, reduces production cost, also reduces environmental pollution.
Accompanying drawing explanation
Fig. 1 is the schematic flow sheet of one embodiment of the present invention.
Number in the figure is: 1, material storaging tank; 2, condensation reaction still; 3, stratification device; 4, thick oil wash neutralising arrangement; 5, solvent recuperation distillation tower; 6, the thick oily reaction unit of methylene acetone; 7, hydrogenation reaction cauldron; 8, hay tank; 9, alcohol recycle distillation tower; 10, p-methoxy benzyl acetone hangs white oil reaction unit; 11, demethylating reaction still; 12, acid recovery distillation tower; 13, tower is collected in thick raspberry ketone distillation; 14, primary crystallization tank; 15, recrystallization tank; 16, whizzer; 17, drying and crushing system.
Embodiment
The present invention a kind ofly synthesizes the production line of raspberry ketone by natural equivalent anisic aldehyde, comprises that the material storaging tank 1, condensation reaction still 2, stratification device 3, thick oil wash neutralising arrangement 4, solvent recuperation distillation tower 5, the thick oily reaction unit 6 of methylene acetone, hydrogenation reaction cauldron 7, hay tank 8, alcohol recycle distillation tower 9, the p-methoxy benzyl acetone that connect successively hang white oil reaction unit 10, tower 13, primary crystallization tank 14, recrystallization tank 15, whizzer 16 and drying and crushing system 17 are collected in demethylating reaction still 11, acid recovery distillation tower 12, thick raspberry ketone distillation.Wherein, the outlet of described hay tank 8 is also connected with the import of hydrogenation reaction cauldron 7, the outlet of alcohol recycle distillation tower 9 is also connected with the import of hydrogenation reaction cauldron 7, white oil reaction unit 10 is also hung in the outlet of acid recovery distillation tower 12 import with p-methoxy benzyl acetone is connected, and the outlet of described solvent recuperation distillation tower 5 is also connected with the import of thick oil wash neutralising arrangement 4.
When producing, raw material natural equivalent anisic aldehyde, buck and acetone being put into condensation reaction still 2 and carries out condensation reaction; After reaction terminates, reactant is sent into stratification device 3 and carry out layered shaping, lower floor's alkali lye is sent in buck hold tank; Reactant after leaving standstill then is sent in thick oil wash neutralising arrangement 4, adds acetum simultaneously, toluene solution washs in thick oil wash neutralising arrangement 4; Reactant after washing neutralization is sent in solvent recuperation distillation tower 5, and reclaim the toluene in reactant, the toluene of recovery directly can pass in thick oil wash neutralising arrangement 4 and again utilize; Then by thick for methylene acetone oily reaction unit 6, add alcohol simultaneously and dilute; Send in hydrogenation reaction cauldron 7 again, catalytic hydrogenating reduction prepares Anisylacetone stoste; After having reacted, send into hay tank 8, reclaim catalyzer, the catalyzer of recovery directly can pass in hydrogenation apparatus and again utilize; Anisylacetone stoste after filtering then sends into alcohol recycle distillation tower 9, and carry out Distillation recovery to the alcohol that the inside is contained, the alcohol of recovery directly can pass in hydrogenation reaction cauldron 7 and again utilize, and obtains Anisylacetone simultaneously; Anisylacetone is then sent into p-methoxy benzyl acetone and is hung in white reaction unit, and extra-high vacuum is distilled the Anisylacetone collected and hung white oil and add acetic acid dilution, to accelerate the reaction times, reduces the generation of by product; Then the Anisylacetone after being diluted by acetic acid hangs white oil and sends in demethylating reaction still 11, and adds Hydrogen bromide and react, obtained thick raspberry ketone; Then will react stoste and send into Distillation recovery acid in acid recovery distillation tower 12 together with thick raspberry ketone, restored acid directly can pass into p-methoxy benzyl acetone and hang in white oil reaction unit 10 and again utilize; Thick raspberry ketone and other reaction material are then sent into the distillation of thick raspberry ketone and are collected in tower 13, and the thick product of raspberry ketone is collected in distillation; The thick product of the raspberry ketone obtained is sent in primary crystallization tank 14, and add toluene and carry out preliminary purification, and then feeding recrystallization tank 15, whizzer 16 are purified further successively, finally send into drying and crushing system 17 and carry out drying and crushing process, obtained raspberry ketone product.
Claims (10)
1. one kind is synthesized the production line of raspberry ketone by natural equivalent anisic aldehyde, comprise material storaging tank (1), it is characterized in that: also comprise the condensation reaction still (2), hydrogenation reaction cauldron (7), alcohol recycle distillation tower (9), demethylating reaction still (11), primary crystallization tank (14), recrystallization tank (15), whizzer (16) and the drying and crushing system (17) that connect successively, the outlet of described material storaging tank (1) is connected with the import of condensation reaction still (2).
2. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 1, is characterized in that: between hydrogenation reaction cauldron (7) and demethylating reaction still (11), be also connected with p-methoxy benzyl acetone hang white oil reaction unit (10).
3. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 2, is characterized in that: hang between white oil reaction unit (10) at hydrogenation reaction cauldron (7) and p-methoxy benzyl acetone and be also connected with hay tank (8).
4. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 3, it is characterized in that: the outlet of described hay tank (8) is also connected with the import of hydrogenation reaction cauldron (7), the outlet of alcohol recycle distillation tower (9) is also connected with the import of hydrogenation reaction cauldron (7).
5. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 2, it is characterized in that: collect between tower (13) at demethylating reaction still (11) and the distillation of thick raspberry ketone and be connected with acid recovery distillation tower (12), white oil reaction unit (10) is also hung in the outlet of acid recovery distillation tower (12) import with p-methoxy benzyl acetone is connected.
6. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 1, is characterized in that: between condensation reaction still (2) and hydrogenation reaction cauldron (7), be also connected with the thick oily reaction unit (6) of methylene acetone.
7. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 6, is characterized in that: between condensation reaction still (2) and the thick oily reaction unit of methylene acetone (6), be also connected with thick oil wash neutralising arrangement (4) and solvent recuperation distillation tower (5) in turn.
8. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 7, is characterized in that: the outlet of described solvent recuperation distillation tower (5) is also connected with the import of thick oil wash neutralising arrangement (4).
9. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 6, is characterized in that: between condensation reaction still (2) and thick oil wash neutralising arrangement (4), be also connected with stratification device (3).
10. the production line being synthesized raspberry ketone by natural equivalent anisic aldehyde according to claim 1, is characterized in that: between demethylating reaction still (11) and primary crystallization tank (14), be also connected with the distillation of thick raspberry ketone collect tower (13).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510716600.2A CN105198720A (en) | 2015-10-29 | 2015-10-29 | Production line for synthesizing raspberry ketone from natural equivalent anisic aldehyde |
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| CN201510716600.2A CN105198720A (en) | 2015-10-29 | 2015-10-29 | Production line for synthesizing raspberry ketone from natural equivalent anisic aldehyde |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1478768A (en) * | 2003-06-30 | 2004-03-03 | 刘孝民 | Synthesis of raspberry ketone |
| WO2007083071A2 (en) * | 2006-01-23 | 2007-07-26 | Institut National De La Recherche Agronomique - Inra | Process for preparing a precursor of an aromatic compound by biosynthesis |
| CN101717328A (en) * | 2009-09-14 | 2010-06-02 | 广西万山香料有限责任公司 | New method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde |
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2015
- 2015-10-29 CN CN201510716600.2A patent/CN105198720A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1478768A (en) * | 2003-06-30 | 2004-03-03 | 刘孝民 | Synthesis of raspberry ketone |
| WO2007083071A2 (en) * | 2006-01-23 | 2007-07-26 | Institut National De La Recherche Agronomique - Inra | Process for preparing a precursor of an aromatic compound by biosynthesis |
| CN101717328A (en) * | 2009-09-14 | 2010-06-02 | 广西万山香料有限责任公司 | New method for synthesizing raspberry ketone by using natural equivalent anisic aldehyde |
Non-Patent Citations (1)
| Title |
|---|
| 徐冬青等: "《天然等同物覆盆子酮的合成工艺研究》", 《化学研究与应用》 * |
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