CN101735058A - Synthesis method of phenoxy acetic acid allyl ester - Google Patents
Synthesis method of phenoxy acetic acid allyl ester Download PDFInfo
- Publication number
- CN101735058A CN101735058A CN200810159965A CN200810159965A CN101735058A CN 101735058 A CN101735058 A CN 101735058A CN 200810159965 A CN200810159965 A CN 200810159965A CN 200810159965 A CN200810159965 A CN 200810159965A CN 101735058 A CN101735058 A CN 101735058A
- Authority
- CN
- China
- Prior art keywords
- acetic acid
- phenoxy acetic
- acid
- allyl ester
- synthesis method
- 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.)
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- VUFZVGQUAVDKMC-UHFFFAOYSA-N Allyl phenoxyacetate Chemical compound C=CCOC(=O)COC1=CC=CC=C1 VUFZVGQUAVDKMC-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000001308 synthesis method Methods 0.000 title claims abstract description 7
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 26
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims abstract description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 238000003756 stirring Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000003729 cation exchange resin Substances 0.000 claims description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910000831 Steel Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 239000010959 steel Substances 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 229940023913 cation exchange resins Drugs 0.000 claims description 2
- 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 2
- 238000000034 method Methods 0.000 abstract description 8
- 238000005516 engineering process Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 238000003889 chemical engineering Methods 0.000 abstract 1
- 239000000110 cooling liquid Substances 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- 230000002950 deficient Effects 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of chemical engineering and in particular relates to a synthesis method of phenoxy acetic acid allyl ester. Phenoxy acetic acid and allyl alcohol are adopted to generate the phenoxy acetic acid allyl ester under the action of an acid catalyst. The method has easy obtained raw materials with low price, simple process flow and advanced technology and adopts continuous type production, and waste water generated in the process flow can be recycled and used as a cooling liquid or used for recovering tail gas to obtain muriatic acid, thereby saving the production cost. The yield of the method reaches higher than 97 percent, and the method meets the requirements on nature, environmental protection and health of the social subject.
Description
Technical field
The invention belongs to chemical technology field, relate in particular to a kind of synthesis method of phenoxy acetic acid allyl ester.
Background technology
Allyl phenoxyacetate molecular formula: C
11H
12O
3, molecular weight: 192.22, outward appearance is a liquid, has the fruit fragrance of pineapple sample, and with the honey aromatic, and is extremely fresh and be rich in natural sense, the fragrant component as fruital, blue or green perfume (or spice) and lavandula angustifolia can produce natural sense true to nature.Not only be applied to medicine industry, be applied to fields such as cosmetic industry, food, tobacco widely.There is the processing step complexity in the common process, the bad control of processing condition, and the not high defective of yield.
Summary of the invention
The present invention has overcome above-mentioned technical defective, and purpose is to provide a kind of synthesis method of phenoxy acetic acid allyl ester.
Adopt phenoxy acetic acid and vinylcarbinol under the effect of an acidic catalyst, to generate allyl phenoxyacetate.Wherein the concrete steps of synthesizing allyl phenoxyacetate are:
(1) in glassed steel reaction vessels, adds phenoxy acetic acid, vinylcarbinol, benzene, storng-acid cation exchange resin, wherein 290～320 parts, 150～180 parts vinylcarbinols of phenoxy acetic acid, 250～280 parts of benzene, 5～15 parts of storng-acid cation exchange resins;
(2) stirring is warming up to 80～103 ℃ and is back to anhydrous generation, and stirring velocity is 8hr;
(3) filtration catalizer (recovery set is used);
(4) boil off benzene and excessive vinylcarbinol under the normal pressure;
(5) cut of 144～146 ℃/1.2Kpa is collected in underpressure distillation, obtains allyl phenoxyacetate.
Strong-acid ion exchange resin is sulfuric acid, tosic acid, sulfonic acid etc.
Beneficial effect is: raw material of the present invention is easy to get, cheap, and technical process is simple, and advanced technology adopts continous way production, can be used as refrigerating fulid behind the waste water reclamation that produces in the technological process and uses or be used to reclaim tail gas, obtains hydrochloric acid, saved production cost.Yield is up to 97% more than, and presses close to the requirement of the main body of the society for " natural, environmental protection, health ".
Embodiment
Further specify the present invention below by embodiment.
Embodiment 1
In the 2000L glassed steel reaction vessels, add the 290Kg phenoxy acetic acid, 250Kg benzene, the 150Kg vinylcarbinol, the 6Kg storng-acid cation exchange resin, stirring is warming up to 80 ℃ and is back to anhydrous generation, and stirring velocity is 8hr, filtration catalizer (recovery set is used), boil off benzene and excessive vinylcarbinol under the normal pressure, the cut of 144～146 ℃/1.2Kpa is collected in underpressure distillation again, and yield reaches 97.3%.
Embodiment 2
In the 2000L glassed steel reaction vessels, add the 310Kg phenoxy acetic acid, 270Kg benzene, the 165Kg vinylcarbinol, the 9Kg storng-acid cation exchange resin, stirring is warming up to 95 ℃ and is back to anhydrous generation, and stirring velocity is 8hr, filtration catalizer (recovery set is used), boil off benzene and excessive vinylcarbinol under the normal pressure, the cut of 144～146 ℃/1.2Kpa is collected in underpressure distillation again, and yield reaches 97.9%.
Embodiment 3
In the 2000L glassed steel reaction vessels, add the 320Kg phenoxy acetic acid, 280Kg benzene, the 180Kg vinylcarbinol, the 15Kg storng-acid cation exchange resin, stirring is warming up to 103 ℃ and is back to anhydrous generation, and stirring velocity is 8hr, filtration catalizer (recovery set is used), boil off benzene and excessive vinylcarbinol under the normal pressure, the cut of 144～146 ℃/1.2Kpa is collected in underpressure distillation again, and yield reaches 97.5%.
Claims (2)
1. synthesis method of phenoxy acetic acid allyl ester, it is characterized in that: concrete steps are:
(1) in glassed steel reaction vessels, adds phenoxy acetic acid, vinylcarbinol, benzene, storng-acid cation exchange resin, wherein 290～320 parts, 150～180 parts vinylcarbinols of phenoxy acetic acid, 250～280 parts of benzene, 5～15 parts of storng-acid cation exchange resins;
(2) stirring is warming up to 80～103 ℃ and is back to anhydrous generation, and stirring velocity is 8hr;
(3) filtration catalizer (recovery set is used);
(4) boil off benzene and excessive vinylcarbinol under the normal pressure;
(5) cut of 144～146 ℃/1.2Kpa is collected in underpressure distillation, obtains allyl phenoxyacetate.
2. synthesis method of phenoxy acetic acid allyl ester as claimed in claim 1 is characterized in that: described storng-acid cation exchange resin is sulfuric acid, tosic acid, sulfonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810159965A CN101735058A (en) | 2008-11-14 | 2008-11-14 | Synthesis method of phenoxy acetic acid allyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810159965A CN101735058A (en) | 2008-11-14 | 2008-11-14 | Synthesis method of phenoxy acetic acid allyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101735058A true CN101735058A (en) | 2010-06-16 |
Family
ID=42459148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810159965A Pending CN101735058A (en) | 2008-11-14 | 2008-11-14 | Synthesis method of phenoxy acetic acid allyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101735058A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180491A (en) * | 2018-10-29 | 2019-01-11 | 淮安万邦香料工业有限公司 | A kind of synthetic method of pineapple ether |
-
2008
- 2008-11-14 CN CN200810159965A patent/CN101735058A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180491A (en) * | 2018-10-29 | 2019-01-11 | 淮安万邦香料工业有限公司 | A kind of synthetic method of pineapple ether |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20100616 |