CN102001941B - Method for synthesizing 3,3-dimethyl-4-pentenoic acid methyl ester - Google Patents
Method for synthesizing 3,3-dimethyl-4-pentenoic acid methyl ester Download PDFInfo
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- CN102001941B CN102001941B CN2010106168864A CN201010616886A CN102001941B CN 102001941 B CN102001941 B CN 102001941B CN 2010106168864 A CN2010106168864 A CN 2010106168864A CN 201010616886 A CN201010616886 A CN 201010616886A CN 102001941 B CN102001941 B CN 102001941B
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- Prior art keywords
- dimethyl
- methyl ester
- acid methyl
- pentenoic acid
- product
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- MKLKDUHMZCIBSJ-UHFFFAOYSA-N methyl 3,3-dimethylpent-4-enoate Chemical compound COC(=O)CC(C)(C)C=C MKLKDUHMZCIBSJ-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title abstract description 10
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 12
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- 238000010189 synthetic method Methods 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 238000012423 maintenance Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- -1 isoamyl enol Chemical class 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 3,3-dimethyl-4-pentenoic acid methyl ester, which comprises the following steps of: I) at the temperature of between 0 and 40 DEG C, uniformly mixing trimethyl orthoacetate, a catalyst and isoamyl enol in a molar ratio of 1:(0.0005-0.02):(0.1-0.5) in a reactor by stirring, and reacting for 0.2 to 2 hours to generate synthetic feed liquid of the 3,3-dimethyl-4-pentenoic acid methyl ester; and II) removing a byproduct of methanol and the excessive trimethyl orthoacetate from the synthetic feed liquid of the 3,3-dimethyl-4-pentenoic acid methyl ester obtained in the step I), rectifying the remaining materials to obtain a 3,3-dimethyl-4-pentenoic acid methyl ester product. The method for synthesizing the 3,3-dimethyl-4-pentenoic acid methyl ester has high reaction speed, short cycle, less byproduct of tar, high reaction yield of over 88 percent, high product content of over 99.5 percent and concise process, and is suitable for industrial production.
Description
Technical field
The present invention relates to a kind of synthetic method of compound, be specifically related to a kind of synthetic method of 3,3-dimethyl-4-pentenoic acid methyl ester.
Background technology
3,3-dimethyl-4-pentenoic acid methyl ester, chemical name are 3,3 dimethyl-4-amylene-4 acid methyl ester, and sterling is water white transparency, have the liquid of specific stimulation smell.Be dissolved in ethanol, ethyl acetate, the organic solvents such as ether, water insoluble; Structural formula:
3,3-dimethyl-4-pentenoic acid methyl ester is a kind of important industrial chemicals, it not only is used in general organic synthesis, in the chemistry of pesticide industrial aspect, a kind of intermediate as synthetic fluorine, chlorine, bromine three major types pyrethroid pesticide, occupy important position, take the lead in the beginning of the seventies realizing suitability for industrialized production by Britain prompt sharp Kanggong department.
Synthetic the carried out literature review of document " study on the synthesis of 3,3-dimethyl-4-pentenoic acid methyl ester " (agricultural chemicals 09 phase in 1996) to 3,3-dimethyl-4-pentenoic acid methyl ester.Existing intermittently synthesis technique, be all under heating condition, by dripping wherein a kind of raw material, reacts, and removes simultaneously methyl alcohol and the excessive trimethyl orthoacetate of by-product, then by high temperature, reset and obtain the product 3,3-dimethyl-4-pentenoic acid methyl ester.Process operation is loaded down with trivial details, and long reaction time, material, owing to being heated for a long time, cause rectifying tar many, and product yield is the 65-85% left and right only.CN200610048136 has mentioned a kind of 3,3-dimethyl-4-pentenoic acid methyl ester pressurization synthesis technique, can improve yield to 88%, but equipment requirements is higher, and there is certain potential safety hazard in suitability for industrialized production.
Summary of the invention
The object of the invention is to provide intermittently synthetic method of a kind of 3,3-dimethyl-4-pentenoic acid methyl ester,, because technological process is simple, is fit to the industrialization safety in production, and quality product, yield are higher.
Above-mentioned purpose of the present invention is achieved through the following technical solutions:
A kind of synthetic method of 3,3-dimethyl-4-pentenoic acid methyl ester is provided, comprises the following steps:
I) under 0-40 ℃, trimethyl orthoacetate, catalyzer and the prenol mol ratio by 1:0.0005-0.02:0.1-0.5 is uniformly mixed in reactor, reaction 0.2-2 hour, generate the synthetic feed liquid of 3,3-dimethyl-4-pentenoic acid methyl ester;
II) remove step I) methyl alcohol and the excessive trimethyl orthoacetate of by-product in the synthetic feed liquid of the 3,3-dimethyl-4-pentenoic acid methyl ester that obtains, clout obtains the 3,3-dimethyl-4-pentenoic acid methyl ester product by rectifying.
Step I) described catalyzer is 85% phosphoric acid, anhydrous phosphoric acid, propionic acid, phenylformic acid or tosic acid; Preferred anhydrous phosphoric acid.
Step I) described reactor is preferably with the tank reactor of knockout tower and stirring.
Step II) the described methyl alcohol of the by-product in the synthetic feed liquid of 3,3-dimethyl-4-pentenoic acid methyl ester and the process of excessive trimethyl orthoacetate of removing, the 3-5 hour that preferably first material heated up, make final temperature reach 140-160 ℃, and then keep temperature 1-5 hour.
Compared with prior art, characteristics of the present invention are that the operant response process is simple, and are with short production cycle, and by product tar is few, and reaction yield is more than 88%, and product content is more than 99.5%, and technique is succinct, are fit to suitability for industrialized production.
In this explanation, content % is weight fraction if no special instructions.
Embodiment
Below with the form of embodiment, explain in detail technical scheme of the present invention and effect, but the present invention is not limited to following examples.
Following % content all refers to massfraction without specified otherwise.
Embodiment 1
under 20 ℃ of room temperatures in proportion with trimethyl orthoacetate 1200kg(10kmol), anhydrous phosphoric acid 1.2kg (0.0122 kmol) and prenol 86kg(1kmol) drop in the 2000L tank reactor, be connected to the filler knockout tower of Φ 400 * 6000 on still, stir and mixed in 1 hour, open reacting kettle jacketing steam, the methyl alcohol and the excessive trimethyl orthoacetate that heat up and remove by-product by knockout tower, take off 3-4 hour still temperature to 145 ℃, and holding temperature 2 hours is constant, reaction finishes, clout obtains the 3,3-dimethyl-4-pentenoic acid methyl ester product by rectifying, gas chromatographic analysis content 99.59%, yield 90%.
Embodiment 2
In proportion trimethyl orthoacetate 1200kg, phenylformic acid 1.2kg and prenol 90kg are dropped in the 2000L tank reactor under 30 ℃ of room temperatures, be connected to the filler knockout tower of Φ 400 * 6000 on still, stir and mixed in 0.2 hour, open reacting kettle jacketing steam, the methyl alcohol and the excessive trimethyl orthoacetate that heat up and remove by-product by knockout tower, take off 3-5 hour still temperature to 150 ℃, and holding temperature 1 hour is constant, reaction finishes, clout obtains the 3,3-dimethyl-4-pentenoic acid methyl ester product by rectifying, gas chromatographic analysis content 99.33%, yield 88%.
Embodiment 3
In proportion trimethyl orthoacetate 900kg, anhydrous phosphoric acid 0.9kg and prenol 86kg are dropped in the 2000L tank reactor under 10 ℃ of room temperatures, be connected to the filler knockout tower of Φ 400 * 6000 on still, stir and mixed in 1.5 hours, open reacting kettle jacketing steam, the methyl alcohol and the excessive trimethyl orthoacetate that heat up and remove by-product by knockout tower, take off 3-5 hour still temperature to 140 ℃, and holding temperature 2 hours is constant, reaction finishes, clout obtains the 3,3-dimethyl-4-pentenoic acid methyl ester product by rectifying, gas chromatographic analysis content 99.5%, yield 89.9%.
Embodiment 4
In proportion trimethyl orthoacetate 1000kg, tosic acid 0.9kg and prenol 86kg are dropped in the 2000L tank reactor under 5 ℃ of room temperatures, be connected to the filler knockout tower of Φ 400 * 6000 on still, stir and mixed in 2 hours, open reacting kettle jacketing steam, the methyl alcohol and the excessive trimethyl orthoacetate that heat up and remove by-product by knockout tower, take off 3-5 hour still temperature to 150 ℃, and holding temperature 4 hours is constant, reaction finishes, clout obtains the 3,3-dimethyl-4-pentenoic acid methyl ester product by rectifying, gas chromatographic analysis content 99.45%, yield 88.1%.
Claims (4)
1. the synthetic method of a 3,3-dimethyl-4-pentenoic acid methyl ester comprises the following steps:
I) under 0-40 ℃, trimethyl orthoacetate, catalyzer and the prenol mol ratio by 1:0.0005-0.02:0.1-0.5 is uniformly mixed in reactor, reaction 0.2-2 hour, generate the synthetic feed liquid of 3,3-dimethyl-4-pentenoic acid methyl ester;
II) first with step I) the material intensification 3-5 hour that obtains, make final temperature reach 140-160 ℃, and then maintenance temperature 1-5 hour, remove thus step I) methyl alcohol and the excessive trimethyl orthoacetate of by-product in the synthetic feed liquid of the 3,3-dimethyl-4-pentenoic acid methyl ester that obtains, clout obtains the 3,3-dimethyl-4-pentenoic acid methyl ester product by rectifying.
2. the synthetic method of 3,3-dimethyl-4-pentenoic acid methyl ester claimed in claim 1, it is characterized in that: step I) described catalyzer is 85% phosphoric acid, anhydrous phosphoric acid, propionic acid, phenylformic acid or tosic acid.
3. the synthetic method of 3,3-dimethyl-4-pentenoic acid methyl ester claimed in claim 2, it is characterized in that: described catalyzer is anhydrous phosphoric acid.
4. the synthetic method of 3,3-dimethyl-4-pentenoic acid methyl ester claimed in claim 1, it is characterized in that: step I) described reactor is the tank reactor with knockout tower and stirring.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010106168864A CN102001941B (en) | 2010-12-31 | 2010-12-31 | Method for synthesizing 3,3-dimethyl-4-pentenoic acid methyl ester |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010106168864A CN102001941B (en) | 2010-12-31 | 2010-12-31 | Method for synthesizing 3,3-dimethyl-4-pentenoic acid methyl ester |
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| CN102001941A CN102001941A (en) | 2011-04-06 |
| CN102001941B true CN102001941B (en) | 2013-11-13 |
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| CN2010106168864A Active CN102001941B (en) | 2010-12-31 | 2010-12-31 | Method for synthesizing 3,3-dimethyl-4-pentenoic acid methyl ester |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102557934A (en) * | 2012-01-17 | 2012-07-11 | 山东高新润农化学有限公司 | Method for continuously synthesizing 3,3-dimethyl-4-pentenoic acid methylester |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041343A1 (en) * | 1980-06-02 | 1981-12-09 | Ici Australia Limited | A process for the synthesis of gamma-unsaturated carboxylic acid esters |
| CN1907947A (en) * | 2006-08-09 | 2007-02-07 | 淄博万昌科技发展有限公司 | Method of preparing 3,3-dimethyl-4-pentenoic acid methyl ester with industrial scale |
| CN101157608A (en) * | 2007-11-20 | 2008-04-09 | 敖枝平 | Method for preparing 4-pentenoic acid |
| CN101565372A (en) * | 2008-04-21 | 2009-10-28 | 南通天泽化工有限公司 | Preparation process of 3,3-dimethyl-4-pentenoic acid methyl ester |
| CN201482477U (en) * | 2009-06-23 | 2010-05-26 | 南通天泽化工有限公司 | Stirrer for 3,3-dimethyl-4-pentenoic acid methyl ester aerogenesis kettle |
-
2010
- 2010-12-31 CN CN2010106168864A patent/CN102001941B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041343A1 (en) * | 1980-06-02 | 1981-12-09 | Ici Australia Limited | A process for the synthesis of gamma-unsaturated carboxylic acid esters |
| CN1907947A (en) * | 2006-08-09 | 2007-02-07 | 淄博万昌科技发展有限公司 | Method of preparing 3,3-dimethyl-4-pentenoic acid methyl ester with industrial scale |
| CN101157608A (en) * | 2007-11-20 | 2008-04-09 | 敖枝平 | Method for preparing 4-pentenoic acid |
| CN101565372A (en) * | 2008-04-21 | 2009-10-28 | 南通天泽化工有限公司 | Preparation process of 3,3-dimethyl-4-pentenoic acid methyl ester |
| CN201482477U (en) * | 2009-06-23 | 2010-05-26 | 南通天泽化工有限公司 | Stirrer for 3,3-dimethyl-4-pentenoic acid methyl ester aerogenesis kettle |
Non-Patent Citations (3)
| Title |
|---|
| 张钟宪.化工过程开发概论.《化工过程开发概论》.首都师范大学出版社,2005,(第1版), * |
| 贲亭酸甲酯的合成研究;邹军等;《农药》;19960925;第35卷(第9期);第8-9、20页 * |
| 邹军等.贲亭酸甲酯的合成研究.《农药》.1996,第35卷(第9期), |
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