CN101260042A - Method for preparing cinnamyl acetate - Google Patents
Method for preparing cinnamyl acetate Download PDFInfo
- Publication number
- CN101260042A CN101260042A CNA2008100473584A CN200810047358A CN101260042A CN 101260042 A CN101260042 A CN 101260042A CN A2008100473584 A CNA2008100473584 A CN A2008100473584A CN 200810047358 A CN200810047358 A CN 200810047358A CN 101260042 A CN101260042 A CN 101260042A
- Authority
- CN
- China
- Prior art keywords
- cinnamyl acetate
- styryl carbinol
- cinnamyl
- temperature
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- SDOFMBGMRVAJNF-KVTDHHQDSA-N (2r,3r,4r,5r)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-KVTDHHQDSA-N 0.000 title claims abstract description 37
- WJSDHUCWMSHDCR-VMPITWQZSA-N cinnamyl acetate Natural products CC(=O)OC\C=C\C1=CC=CC=C1 WJSDHUCWMSHDCR-VMPITWQZSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract 3
- 150000004075 acetic anhydrides Chemical class 0.000 abstract 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 239000012043 crude product Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 3
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 239000004857 Balsam Substances 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 244000068485 Convallaria majalis Species 0.000 description 1
- 235000009046 Convallaria majalis Nutrition 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920006330 Styrox Polymers 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 235000020995 raw meat Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for cinnamyl acetate. The steps of the method are as follows: A) cinnamic alcohols and acetic anhydrides are mixed for reaction according to a certain mol ratio; catalysts are taken to dissolve in the acetic anhydrides, and the temperature is preserved, and the cinnamic alcohols are dropwise added; B) after the addition of the cinnamic alcohols, the temperature is kept in the range of from 40 to 50 DEG C for reaction; C) after the heat preservation, the cinnamyl acetate products are obtained by the water washing and neutralization; D) the cinnamyl acetate products obtained undergo the fraction collection under the vacuum of negative 0.096 to negative 0.1Mpa, obtaining the cinnamyl acetate finished products; the invention has the advantages of simple method, convenient operation, low material costs, high yield and no environmental pollution, and is quite suitable for the industrialized production; moreover, the yield of the production of the cinnamyl acetate is as high as 88.6 percent.
Description
Technical field
The invention belongs to chemical field, be specifically related to a kind of preparation method of cinnamyl acetate, its mainly as fragrance applications in type essence such as configuration cassia bark, apple, cherry and pineapples; Compound perfume as essence such as jacinthe, cloves, the lily of the valley, jasmine, masts.
Background technology
The cinnamyl acetate chemical name is a cinnamyl acetate, is a kind of important fine-chemical intermediate, is widely used in the production of products such as medicine, spices.The universal method of preparation cinnamyl acetate mainly contains at present: 1, adopt hot caustic solution to handle and extract acetate acid cinnamic ester in natural Styrox, white Surinam balsam, Oleum Cinnamomi, the silvery white cassie oil, it is higher that this method is produced preparation cinnamyl acetate cost, the starting material difficulty is asked, complex process, production cycle is long, and contaminate environment is serious; 2, direct esterification in the presence of the vitriol oil is reacted and is produced by cinnamic alcohol and acetate, though adopt this method production cinnamyl acetate technology simple, by product is many, and product purity is poor, and yield is low; 3, directly prepare cinnamyl acetate through acetylization reaction by styryl carbinol and diacetyl oxide, this technology is simple, and is easy to operate, but the transformation efficiency of used raw meat cinnamic alcohol is low, and product purity does not reach quality standard; 4, adopt sodium acetate and cinnamyl chlorine at N, there is time prepared in reaction cinnamyl acetate in dinethylformamide, and the raw materials used cinnamyl chlorine of this technology is poisonous and cost an arm and a leg, market supply is limited, employed solvent N, the dinethylformamide price is also relatively more expensive, and product yield has only 54%.
Summary of the invention
Purpose of the present invention overcomes above-mentioned described the deficiencies in the prior art exactly, and a kind of preparation side of cinnamyl acetate is provided.The present invention adopts diacetyl oxide and styryl carbinol, is the Preparation of Catalyst cinnamyl acetate with phosphoric acid or tosic acid, and technology is simple, and is easy to operate, and raw material is easy to get, with low cost, and the yield height, and quality is good, and is also pollution-free to environment, is very suitable for suitability for industrialized production.
To achieve these goals, the present invention by the following technical solutions, its step is
A, styryl carbinol and diacetyl oxide are 1 in molar ratio: the 1-3 reaction that feeds intake.0.5 or 1 or 2 or 3% the catalyzer (catalyzer is 85 or 88 or 92 or 98% phosphoric acid or tosic acid) of measuring by the styryl carbinol quality is dissolved in the diacetyl oxide, stir, holding temperature is controlled at 20 or 24 or 28 or 32 or 37 or 42 or 45 ℃ and drips styryl carbinol, and the styryl carbinol dropping time is 5 or 6 or 7 hours.
B, styryl carbinol dropwise, and temperature remains on 40 or 44 or 48 or 50 ℃ of reactions 1 or 2 hour.
C, the insulation finish through washing neutralize the cinnamyl acetate crude product.
The cinnamyl acetate crude product of D, gained is collected the cinnamyl acetate finished product in 140 or 148 or 156 or 162 or 170 or 174 ℃ under decompression-0.096--0.1Mpa condition.
The inventive method is easily gone, and technology is simple, and production cost is low, and is pollution-free, stable and reliable product quality, and raw material is easy to get, and is highly suitable for suitability for industrialized production, and producing the cinnamyl acetate yield can be up to 88.6% (in styryl carbinol).
Embodiment
Embodiment 1:
0.7g85% phosphoric acid or tosic acid are dissolved in 150g (1.47mol) diacetyl oxide stir, maintain the temperature at 20 or 24 or 28 or 32 or 37 or 42 or 45 ℃ and drip styryl carbinol 134g (1.0mol), the styryl carbinol dropping time is 5 or 6 or 7 hours.Styryl carbinol dropwises and remains on 40 or 44 or 48 or 50 ℃ of reactions 1 or 2 hour.The insulation finish through washing neutralize the cinnamyl acetate crude product.The cinnamyl acetate of gained is collected cinnamyl acetate finished product 143.4g, yield 82.4% in 170-174 ℃ under decompression-0.096Mpa condition.Product purity reaches 98.4%.
Embodiment 2
1.4g88% phosphoric acid or tosic acid are dissolved in 102g (1.0mol) diacetyl oxide stir, maintain the temperature at 20 or 22 or 26 or 30 or 35 or 40 or 45 ℃ and drip styryl carbinol 134g (1.0mol), the styryl carbinol dropping time is 5 or 6 or 7 hours.Styryl carbinol dropwises and remains on 40 or 43 or 47 or 50 ℃ of reactions 1 or 2 hour.The insulation finish through washing neutralize the cinnamyl acetate crude product.The cinnamyl acetate of gained is collected cinnamyl acetate finished product 148.0g, yield 84.1% in 162-166 ℃ under decompression-0.098Mpa condition.Product purity reaches 98.5%.
Embodiment 3
2.7g92% phosphoric acid or tosic acid are dissolved in 204g (2mol) diacetyl oxide stir, maintain the temperature at 20 or 23 or 27 or 31 or 39 or 43 or 45 ℃ and drip styryl carbinol 134g (1.0mol), the styryl carbinol dropping time is 5 or 6 or 7 hours.Styryl carbinol dropwises and remains on 40 or 45 or 49 or 50 ℃ of reactions 1 or 2 hour.The insulation finish through washing neutralize the cinnamyl acetate crude product.The cinnamyl acetate of gained is collected cinnamyl acetate finished product 151.7g, yield 86.2% in 154-157 ℃ under decompression-0.099Mpa condition.Product purity reaches 98.5%.
Embodiment 4
4.0g98% phosphoric acid or tosic acid are dissolved in 306g (3mol) diacetyl oxide stir, maintain the temperature at 20 or 25 or 29 or 34 or 38 or 41 or 45 ℃ and drip styryl carbinol 134g (1.0mol), the styryl carbinol dropping time is 5 or 6 or 7 hours.Styryl carbinol dropwises and remains on 40 or 42 or 46 or 50 ℃ of reactions 1 or 2 hour.The insulation finish through washing neutralize the cinnamyl acetate crude product.The cinnamyl acetate of gained is collected cinnamyl acetate finished product 157.8g, yield 89.7% in 140-144 ℃ under decompression-0.1Mpa condition.Product purity reaches 98.7%.
Claims (1)
1, a kind of preparation method of cinnamyl acetate the steps include:
A, styryl carbinol and diacetyl oxide are 1 in molar ratio: the 1-3 reaction that feeds intake, be dissolved in the diacetyl oxide by the catalyzer of measuring of the 0.5-3% of styryl carbinol quality, and stir, the temperature of insulation is controlled at 20-45 ℃ and drips styryl carbinol, and the styryl carbinol dropping time is 5-7 hour;
B, styryl carbinol dropwise, and temperature remains on 40-50 ℃ of reaction 1 or 2 hour;
C, the insulation finish through washing neutralize the cinnamyl acetate article;
D, with the cinnamyl acetate article of gained under vacuum-0.096--0.1Mpa, the cut of collecting 140-174 ℃ gets the cinnamyl acetate finished product;
Described catalyzer is that concentration is phosphoric acid or the tosic acid of 85-98%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810047358A CN100595185C (en) | 2008-04-17 | 2008-04-17 | Method for preparing cinnamyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810047358A CN100595185C (en) | 2008-04-17 | 2008-04-17 | Method for preparing cinnamyl acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101260042A true CN101260042A (en) | 2008-09-10 |
| CN100595185C CN100595185C (en) | 2010-03-24 |
Family
ID=39960778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810047358A Expired - Fee Related CN100595185C (en) | 2008-04-17 | 2008-04-17 | Method for preparing cinnamyl acetate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100595185C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101591243B (en) * | 2009-05-11 | 2012-06-20 | 江苏省原子医学研究所 | Method for preparing acetic acid phenolic ester by catalyzing bisphosphonates |
| CN105104922A (en) * | 2015-07-23 | 2015-12-02 | 江西省添美食品有限公司 | Additive used for quick-frozen pastries |
-
2008
- 2008-04-17 CN CN200810047358A patent/CN100595185C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101591243B (en) * | 2009-05-11 | 2012-06-20 | 江苏省原子医学研究所 | Method for preparing acetic acid phenolic ester by catalyzing bisphosphonates |
| CN105104922A (en) * | 2015-07-23 | 2015-12-02 | 江西省添美食品有限公司 | Additive used for quick-frozen pastries |
| CN105104922B (en) * | 2015-07-23 | 2018-09-07 | 帅兵 | A kind of additive for quick-frozen pastry |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100595185C (en) | 2010-03-24 |
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| Date | Code | Title | Description |
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| C06 | Publication | ||
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: HUBEI YUANCHENG PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: WUHAN HEZHONG BIO-CHEMICAL MANUFATURE CO., LTD. Effective date: 20111107 |
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| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 430064 WUHAN, HUBEI PROVINCE TO: 432100 XIAOGAN, HUBEI PROVINCE |
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| TR01 | Transfer of patent right |
Effective date of registration: 20111107 Address after: 432100, Hubei province Xiaogan City Industrial Park Road Patentee after: Hubei Yuancheng Pharmaceutical Co., Ltd. Address before: 430064, No. 201, 1000 street, Wuchang District, Hubei, Wuhan (No. 496, Zhongshan Road) Patentee before: Wuhan Hezhong Bio-chemical Manufature Co., Ltd. |
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| C56 | Change in the name or address of the patentee |
Owner name: HUBEI YUANCHENG SAICHUANG TECHNOLOGY CO., LTD. Free format text: FORMER NAME: HUBEI YUANCHENG PHARMACEUTICAL CO., LTD. |
|
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 432100, Hubei province Xiaogan City Industrial Park Road Patentee after: HUBEI YUANCHENG PHARMACEUTICAL CO., LTD. Address before: 432100, Hubei province Xiaogan City Industrial Park Road Patentee before: Hubei Yuancheng Pharmaceutical Co., Ltd. |
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20100324 Termination date: 20160417 |
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| CF01 | Termination of patent right due to non-payment of annual fee |