CN106631787A - Production method of eugenyl acetate - Google Patents
Production method of eugenyl acetate Download PDFInfo
- Publication number
- CN106631787A CN106631787A CN201710076018.3A CN201710076018A CN106631787A CN 106631787 A CN106631787 A CN 106631787A CN 201710076018 A CN201710076018 A CN 201710076018A CN 106631787 A CN106631787 A CN 106631787A
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- China
- Prior art keywords
- eugenol
- acetic anhydride
- reaction
- production method
- product
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Abstract
The invention discloses a production method of eugenyl acetate. The method comprises the following steps of (1) removing water from a reaction kettle and a backflow device of the reaction kettle to ensure the water content in a system to be lower than 500 PPm; (2) adding eugenol and acetic anhydride into the reaction kettle according to the proportion; performing stirring; (3) adding an organic alkali catalyst into the reaction kettle; (4) raising the temperature to the reaction temperature; performing reaction for 1.5 to 10h; (5) after the reaction is completed, lowering the temperature of the reaction liquid; (6) performing reduced pressure distillation to obtain a product. By using the production method of eugenyl acetate for production, the product yield is about 90 percent; the product purity is 99.0 percent or higher; the product is colorless to light yellow liquid, the soft clove breath is realized; the product yield is high; the purity is high; the quality is high; the production process is simple; the industrial production can be easily realized; the cost is low; meanwhile, waste water and solid waste cannot be generated in the production process.
Description
Technical field
The present invention relates to Acetyl eugenol technical field, more particularly to a kind of Acetyl eugenol production method.
Background technology
Acetyl eugenol, with soft cloves like fragrance, is mainly used in preparing the pungent fragrant class perfume of vanilla, jam and mixing
Material.Can be used for being configured to floral type daily essence, spicy flavoring essence, it can also be used to cloves shampoo, spicy seasoning material etc.
In commodity, increase the fragrance of perfumed article or cover the miscellaneous taste of perfumed article, improve the local flavor of product, make our life more
Plus it is rich and varied.
At present Acetyl eugenol synthesizes mainly with acetic anhydride and eugenol as raw material, Jing acylation reactions and obtain.But it is existing
With the presence of Acetyl eugenol production technology feed stock conversion it is low, the problems such as have waste water, solid waste to produce in production process.
The content of the invention
In consideration of it, it is an object of the invention to provide a kind of Acetyl eugenol production method, to realize improving returning for product
Yield and purity, it is to avoid the generation of waste water, solid waste etc..
A kind of Acetyl eugenol production method of the present invention, it is characterised in that：Comprise the following steps：
1) by reactor and its reflux eliminating water, it is ensured that water content is less than 500PPm in system；
2) proportionally eugenol, acetic anhydride added in reactor, and is stirred；
3) organic alkali catalyst is added into reactor；
4) reaction temperature is warming up to, 1.5-10h is reacted；
5) after the completion of reaction, reacting liquid temperature is reduced；
6) vacuum distillation obtains product；
Purity ＞ 99.0% of the eugenol, acetic anhydride and organic alkali catalyst, moisture ＜ 0.5%；
The step 2) in eugenol and acetic anhydride mol ratio be 1: 1-1: 10；
The step 3) in organic alkali catalyst be：Triethylene diamine, DBU, DBN, DMAP, pyridine, N-methylmorpholine, four
Methyl ethylenediamine, TMG, triethylamine, propylamine, isopropylamine, 1,3- propane diamine, 1,2- propane diamine, para-aminophenol, ortho-aminotoluene,
N-BuLi, LDA, KHMDS, NaHMDS, at least one in potassium tert-butoxide, and sodium tert-butoxide；
The step 4) in reaction temperature control at 50-200 DEG C.
Further, the step 2) in eugenol and acetic anhydride mol ratio be 1: 1-1: 8.
Further, the step 4) in reaction temperature control at 60-150 DEG C.
Beneficial effects of the present invention：
A kind of Acetyl eugenol production method of the present invention, 90% or so, product purity is 99.0% for its product yield
More than, product is colourless to slightly yellow liquid, and with soft cloves breath, product yield is high, and purity is high, and quality is good；And it is raw
Production. art is simple, easily realizes industrialized production, low cost；Waste water, solid waste are not produced in production process simultaneously.
Specific embodiment
With reference to embodiment, the invention will be further described.
Embodiment one：The present embodiment Acetyl eugenol production method, comprises the following steps：
1) by reactor and its reflux eliminating water, it is ensured that water content is less than 500PPm in system；
2) proportionally eugenol, acetic anhydride added in reactor, and is stirred, wherein eugenol and acetic anhydride rub
, than being 1: 1, in this step when eugenol and acetic anhydride mol ratio are higher than 1, eugenol conversion ratio is not high, and the product for obtaining is or not you
Meet the requirements, ratio is less than 10, and acetic anhydride consumption is excessive, can not be recycled again, causes wastage of material；This step is adopted
Eugenol and acetic anhydride mol ratio can improve conversion rate of products to 98% for 1: 1；
3) organic alkali catalyst is added into reactor, organic alkali catalyst is triethylene diamine in the present embodiment, certainly
In different embodiments, organic alkali catalyst can also be：Triethylene diamine, DBU, DBN, DMAP, pyridine, N-methylmorpholine, four
Methyl ethylenediamine, TMG, triethylamine, propylamine, isopropylamine, 1,3- propane diamine, 1,2- propane diamine, para-aminophenol, ortho-aminotoluene,
N-BuLi, LDA, KHMDS, NaHMDS, one or more in potassium tert-butoxide, and sodium tert-butoxide；
4) it is warming up to reaction temperature in reaction temperature, this step to select at 200 DEG C, reacts 1.5h；Temperature mistake in this step
Low reaction speed is slow, and conversion ratio is low, and temperature crosses high impurity content increase；It it is 50-200 DEG C in reaction temperature, the reaction time is
Synthesized under the conditions of 1.5-10h, obtained Acetyl eugenol content more than 99.0%；
5) after the completion of reaction, reacting liquid temperature is reduced；
6) vacuum distillation obtains product.
Purity ＞ 99.0% of eugenol described in the present embodiment, acetic anhydride and organic alkali catalyst, moisture ＜ 0.5%；
The present embodiment Acetyl eugenol production method, its product yield 90% or so, product purity 99.0% with
On, for colourless to weak yellow liquid, with soft cloves breath, product yield is high, and purity is high, and quality is good for product；And produce
Process is simple, easily realizes industrialized production, low cost；Waste water, solid waste are not produced in production process simultaneously.
Embodiment two：The present embodiment Acetyl eugenol production method, comprises the following steps：
1) by reactor and its reflux eliminating water, it is ensured that water content is less than 500PPm in system；
2) proportionally eugenol, acetic anhydride added in reactor, and is stirred, wherein eugenol and acetic anhydride rub
, than being 1: 8, in this step when eugenol and acetic anhydride mol ratio are higher than 1, eugenol conversion ratio is not high, and the product for obtaining is or not you
Meet the requirements, ratio is less than 10, and acetic anhydride consumption is excessive, can not be recycled again, causes wastage of material；This step is adopted
Eugenol and acetic anhydride mol ratio can improve conversion rate of products to 99% for 1: 8；
3) organic alkali catalyst is added into reactor, organic alkali catalyst is N-methylmorpholine in the present embodiment, certainly
In different embodiments, organic alkali catalyst can also be：Triethylene diamine, DBU, DBN, DMAP, pyridine, N-methylmorpholine, four
Methyl ethylenediamine, TMG, triethylamine, propylamine, isopropylamine, 1,3- propane diamine, 1,2- propane diamine, para-aminophenol, ortho-aminotoluene,
N-BuLi, LDA, KHMDS, NaHMDS, one or more in potassium tert-butoxide, and sodium tert-butoxide；
4) it is warming up to reaction temperature in reaction temperature, this step to select at 50 DEG C, reacts 10h；Temperature is too low in this step
Reaction speed is slow, and conversion ratio is low, and temperature crosses high impurity content increase；It it is 50-200 DEG C in reaction temperature, the reaction time is 1.5-
Synthesized under the conditions of 10h, obtained Acetyl eugenol content more than 99.0%；
5) after the completion of reaction, reacting liquid temperature is reduced；
6) vacuum distillation obtains product.
Purity ＞ 99.0% of eugenol described in the present embodiment, acetic anhydride and organic alkali catalyst, moisture ＜ 0.5%；
The present embodiment Acetyl eugenol production method, its product yield 90% or so, product purity 99.0% with
On, for colourless to weak yellow liquid, with soft cloves breath, product yield is high, and purity is high, and quality is good for product；And produce
Process is simple, easily realizes industrialized production, low cost；Waste water, solid waste are not produced in production process simultaneously.
Embodiment three：The present embodiment Acetyl eugenol production method, comprises the following steps：
1) by reactor and its reflux eliminating water, it is ensured that water content is less than 500PPm in system；
2) proportionally eugenol, acetic anhydride added in reactor, and is stirred, wherein eugenol and acetic anhydride rub
, than being 1: 10, in this step when eugenol and acetic anhydride mol ratio are higher than 1, eugenol conversion ratio is not high, the product for obtaining for you
Undesirable, ratio is less than 10, and acetic anhydride consumption is excessive, can not be recycled again, causes wastage of material；This step is adopted
With eugenol and acetic anhydride mol ratio conversion rate of products can be improved to 99% for 1: 10；
3) organic alkali catalyst is added into reactor, organic alkali catalyst is propylamine in the present embodiment, certainly in difference
In embodiment, organic alkali catalyst can also be：Triethylene diamine, DBU, DBN, DMAP, pyridine, N-methylmorpholine, tetramethyl second
Diamines, TMG, triethylamine, propylamine, isopropylamine, 1,3- propane diamine, 1,2- propane diamine, para-aminophenol, ortho-aminotoluene, normal-butyl
Lithium, LDA, KHMDS, NaHMDS, one or more in potassium tert-butoxide, and sodium tert-butoxide；
4) it is warming up to reaction temperature in reaction temperature, this step to select at 150 DEG C, reacts 3h；Temperature is too low in this step
Reaction speed is slow, and conversion ratio is low, and temperature crosses high impurity content increase；It it is 50-200 DEG C in reaction temperature, the reaction time is 1.5-
Synthesized under the conditions of 10h, obtained Acetyl eugenol content more than 99.0%；
5) after the completion of reaction, reacting liquid temperature is reduced；
6) vacuum distillation obtains product.
Purity ＞ 99.0% of eugenol described in the present embodiment, acetic anhydride and organic alkali catalyst, moisture ＜ 0.5%；
The present embodiment Acetyl eugenol production method, its product yield 90% or so, product purity 99.0% with
On, for colourless to weak yellow liquid, with soft cloves breath, product yield is high, and purity is high, and quality is good for product；And produce
Process is simple, easily realizes industrialized production, low cost；Waste water, solid waste are not produced in production process simultaneously.
Finally illustrate, above example is only unrestricted to illustrate technical scheme, although with reference to compared with
Good embodiment has been described in detail to the present invention, it will be understood by those within the art that, can be to the skill of the present invention
Art scheme is modified or equivalent, and without deviating from the objective and scope of technical solution of the present invention, it all should cover at this
In the middle of the right of invention.
Claims (3)
1. a kind of Acetyl eugenol production method, it is characterised in that：Comprise the following steps：
1) by reactor and its reflux eliminating water, it is ensured that water content is less than 500PPm in system；
2) proportionally eugenol, acetic anhydride added in reactor, and is stirred；
3) organic alkali catalyst is added into reactor；
4) reaction temperature is warming up to, 1.5-10h is reacted；
5) after the completion of reaction, reacting liquid temperature is reduced；
6) vacuum distillation obtains product；
Purity ＞ 99.0% of the eugenol, acetic anhydride and organic alkali catalyst, moisture ＜ 0.5%；
The step 2) in eugenol and acetic anhydride mol ratio be 1: 1-1: 10；
The step 3) in organic alkali catalyst be：Triethylene diamine, DBU, DBN, DMAP, pyridine, N-methylmorpholine, tetramethyl
Ethylenediamine, TMG, triethylamine, propylamine, isopropylamine, 1,3- propane diamine, 1,2- propane diamine, para-aminophenol, ortho-aminotoluene, positive fourth
Base lithium, LDA, KHMDS, NaHMDS, at least one in potassium tert-butoxide, and sodium tert-butoxide；
The step 4) in reaction temperature control at 50-200 DEG C.
2. Acetyl eugenol production method according to claim 1, it is characterised in that：The step 2) in eugenol and
Acetic anhydride mol ratio is 1: 1-1: 8.
3. Acetyl eugenol production method according to claim 1, it is characterised in that：The step 4) in reaction temperature
Control is at 60-150 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710076018.3A CN106631787A (en) | 2017-02-10 | 2017-02-10 | Production method of eugenyl acetate |
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| CN201710076018.3A CN106631787A (en) | 2017-02-10 | 2017-02-10 | Production method of eugenyl acetate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112125799A (en) * | 2020-10-14 | 2020-12-25 | 重庆欣欣向荣精细化工有限公司 | Production method of vanillin isobutyrate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1365364A (en) * | 1999-07-29 | 2002-08-21 | 克鲁普顿公司 | Blocked phenolic silanes |
-
2017
- 2017-02-10 CN CN201710076018.3A patent/CN106631787A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1365364A (en) * | 1999-07-29 | 2002-08-21 | 克鲁普顿公司 | Blocked phenolic silanes |
Non-Patent Citations (3)
| Title |
|---|
| ANU BHARDWAJ, ET AL.: "Larvicidal and Structure-Activity Studies of Natural Phenylpropanoids and Their Semisynthetic Derivatives against the Tobacco Armyworm Spodoptera litura (Fab.) (Lepidoptera： Noctuidae)", 《CHEMISTRY & BIODIVERSITY》 * |
| JIANGLEI QIN, ET AL.: "Use of eugenol and rosin as feedstocks for biobased epoxy resins and study of curing and performance properties", 《POLYMER INTERNATIONAL》 * |
| SATISH K. PANDEY, ET AL.: "Structure-activity relationships of monoterpenes and acetyl derivatives against Aedes aegypti (Diptera: Culicidae) larvae", 《PEST MANAGEMENT SCIENCE》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112125799A (en) * | 2020-10-14 | 2020-12-25 | 重庆欣欣向荣精细化工有限公司 | Production method of vanillin isobutyrate |
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