CN103524340A - Isopentene acetate and preparation method thereof - Google Patents
Isopentene acetate and preparation method thereof Download PDFInfo
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- CN103524340A CN103524340A CN201210232041.4A CN201210232041A CN103524340A CN 103524340 A CN103524340 A CN 103524340A CN 201210232041 A CN201210232041 A CN 201210232041A CN 103524340 A CN103524340 A CN 103524340A
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- acetate
- prenyl acetate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- 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
Abstract
The invention relates to isopentene acetate and a new preparation method thereof.
Description
Technical field
The present invention relates to prenyl acetate and prepare its novel method.
Background of invention
In fragrance industry, need to prepare the novel method of perfume molecules always.Art-recognizedly to the actual consideration such as synthetic, may hinder the use of perfume molecules in commercial applications.Sometimes whether the synthetic of unpredictable appointment perfume molecules can carry out by commercial size.Therefore, fragrance industry unremitting effort is with the novel and economic method of research and development preparation perfume molecules.
Summary of the invention
The prenyl acetate that the present invention relates to be expressed from the next:
Formula I
More specifically, the present invention relates to prepare the novel method of prenyl acetate.
By reading following specification sheets, can be expressly understood these embodiments of the present invention and other embodiment.
Embodiment
Since nineteen sixty, prenyl acetate has been a kind of commercially available spices.It has fresh, green, very easily diffusion and the fruital of similar pears are adjusted, be widely used in perfumed product.Prenyl acetate also has the local flavor of strong fruity and similar sweet pears and banana.Therefore, people study and report (for example, referring to United States Patent (USP) the 7th, 612, No. 227) widely to synthetic having done of prenyl acetate.And the invention provides novelty, convenience and economic improved synthetic method.
According to the present invention, can prepare prenyl acetate by following reaction scheme, in an embodiment described reaction scheme is described in detail.Reagent all can commercially availablely be buied.
(i)
It should be appreciated by those skilled in the art that compound of the present invention has mulitiple chiral centers, thereby many isomer of claimed compound are provided.Compound as herein described comprises the isomeric mixtures of these compounds, and can by technical point well known by persons skilled in the art from these isomerss.For example, suitable technology comprises distillation and chromatography, as is called the high performance liquid chromatography, particularly silica gel column chromatography of HPLC, and gas-chromatography (GC) trapping.But commercially available prod major part provides with isomer mixture.
Particular implementation of the present invention is provided below.Other distortion of the present invention will be apparent for a person skilled in the art.Within should be appreciated that these distortion are included in the scope of the invention.In this article, except as otherwise noted, all percentage ratio is weight percentage, and g is gram, and Kg is kilogram, and L rises, and mmHg is millimeter (mm) mercury column (Hg).In an embodiment, IFF represents (the International Flavors& of International Perfume & Essence Co. of New York, United States New York; Fragrances Inc., New York, NY, USA).
example I
The preparation of prenyl acetate: add isoprene (2.54Kg) to being equipped with in three neck round-bottomed flasks of agitator and dropping funnel.Flask temperature is cooled to 0 ℃.Sodium-chlor (NaCl) is divided into 8 equal portions (every part of 100g).In flask, add first part of sodium-chlor (100g), then in 0.5 hour, add dense HCl (1.1Kg).Then approximately every 15 minutes, add other several parts of sodium-chlor, add dense HCl simultaneously.The dense HCl total amount adding is about 12Kg.This reaction aging approximately 2 hours.Organic layer (1.96Kg) is transferred to containing solid sodium carbonate (Na
2cO
3) in separating funnel (150g), obtain chloroisoamylene.Under the existence of triethylamine (Et3N), at 60 ℃ of chloroisoamylenes, further react with sodium acetate (NaOAc), obtain product prenyl acetate, under the pressure of 10mmHg, the boiling point of prenyl acetate is 60 ℃.
Or, can under the existence of catalyzer bronze (copper bronze), with the anhydrous HCl in glycol ether, replace the combination of sodium-chlor and dense HCl.
example II
The preparation of prenyl acetate: add diacetyl oxide ((CH to being equipped with in the 3L tri-neck round-bottomed flasks of agitator and feed hopper
3cOO)
2o, Ac
2o) (516g) and anhydrous sodium acetate (CH
3cOONa) (5g).Flask temperature is heated to 100 ℃.Then in 2 hours, slowly add prenol (408g), simultaneous temperature remains on 105-110 ℃.This reaction aging at least 1.5 hours, to realize maximum conversion.Reaction is cooled to 80 ℃.With the excessive diacetyl oxide of water treatment.Extract organic layer and with aqueous sodium carbonate washing, obtain thick prenyl acetate (590g).Further distillation obtains product prenyl acetate, and its boiling point under the pressure of 10mmHg is 60 ℃.
Claims (8)
1. a method of preparing prenyl acetate, said method comprising the steps of:
(i) isoprene is reacted with sodium-chlor and dense HCl, to obtain chloroisoamylene; And
(ii), under the existence of triethylamine, chloroisoamylene and acetic acid sodium reaction by step (i), obtain prenyl acetate.
2. the method for claim 1, is characterized in that, described step (i) is carried out under the temperature condition of 0 ℃.
3. the method for claim 1, is characterized in that, described step (ii) is carried out under the temperature condition of 60 ℃.
4. a method of preparing prenyl acetate, said method comprising the steps of:
(i) isoprene is reacted with the anhydrous HCl in glycol ether, to obtain chloroisoamylene; And
(ii), under the existence of triethylamine, chloroisoamylene and acetic acid sodium reaction by step (i), obtain prenyl acetate.
5. method as claimed in claim 4, is characterized in that, described step (i) is carried out under bronze existence, and described step (ii) is carried out under the temperature condition of 60 ℃.
6. a method of preparing prenyl acetate, described method comprises the step of prenol and acetic anhydride.
7. method as claimed in claim 6, is characterized in that, described method is carried out under the existence of anhydrous sodium acetate.
8. method as claimed in claim 6, is characterized in that, described method is carried out at the temperature of 105-110 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210232041.4A CN103524340A (en) | 2012-07-05 | 2012-07-05 | Isopentene acetate and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210232041.4A CN103524340A (en) | 2012-07-05 | 2012-07-05 | Isopentene acetate and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103524340A true CN103524340A (en) | 2014-01-22 |
Family
ID=49926750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210232041.4A Pending CN103524340A (en) | 2012-07-05 | 2012-07-05 | Isopentene acetate and preparation method thereof |
Country Status (1)
| Country | Link |
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| CN (1) | CN103524340A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105175219A (en) * | 2015-08-05 | 2015-12-23 | 山东成泰化工有限公司 | Synthesis method of prenyl alcohol |
| CN110590550A (en) * | 2019-09-25 | 2019-12-20 | 万香科技股份有限公司 | Synthesis method of allyl isovalerate |
| WO2023226331A1 (en) * | 2022-05-23 | 2023-11-30 | 南通雅本化学有限公司 | Method for preparing caronic acid and derivative thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036899A (en) * | 1976-01-20 | 1977-07-19 | Uop Inc. | Synthesis of prenyl chloride |
| EP0148314A1 (en) * | 1983-12-12 | 1985-07-17 | Union Camp Corporation | Hydrohalogenation of conjugated dienes in the presence of alcohols |
| EP0444742A1 (en) * | 1990-02-26 | 1991-09-04 | Shell Internationale Researchmaatschappij B.V. | Ester/alcohol synthesis |
| CN1930111A (en) * | 2004-03-25 | 2007-03-14 | 住友化学株式会社 | Preparation method for purified 3-methyl-2-butenyl acetate |
-
2012
- 2012-07-05 CN CN201210232041.4A patent/CN103524340A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036899A (en) * | 1976-01-20 | 1977-07-19 | Uop Inc. | Synthesis of prenyl chloride |
| EP0148314A1 (en) * | 1983-12-12 | 1985-07-17 | Union Camp Corporation | Hydrohalogenation of conjugated dienes in the presence of alcohols |
| EP0444742A1 (en) * | 1990-02-26 | 1991-09-04 | Shell Internationale Researchmaatschappij B.V. | Ester/alcohol synthesis |
| CN1930111A (en) * | 2004-03-25 | 2007-03-14 | 住友化学株式会社 | Preparation method for purified 3-methyl-2-butenyl acetate |
Non-Patent Citations (1)
| Title |
|---|
| STN: "AN 1977:438852", 《STN CAPLUS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105175219A (en) * | 2015-08-05 | 2015-12-23 | 山东成泰化工有限公司 | Synthesis method of prenyl alcohol |
| CN105175219B (en) * | 2015-08-05 | 2017-03-01 | 山东成泰化工有限公司 | The synthetic method of prenol |
| CN110590550A (en) * | 2019-09-25 | 2019-12-20 | 万香科技股份有限公司 | Synthesis method of allyl isovalerate |
| WO2023226331A1 (en) * | 2022-05-23 | 2023-11-30 | 南通雅本化学有限公司 | Method for preparing caronic acid and derivative thereof |
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Application publication date: 20140122 |
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