CN1365963A - Process for preparing 3-bromopropionic acid - Google Patents
Process for preparing 3-bromopropionic acid Download PDFInfo
- Publication number
- CN1365963A CN1365963A CN 01108052 CN01108052A CN1365963A CN 1365963 A CN1365963 A CN 1365963A CN 01108052 CN01108052 CN 01108052 CN 01108052 A CN01108052 A CN 01108052A CN 1365963 A CN1365963 A CN 1365963A
- Authority
- CN
- China
- Prior art keywords
- hydrogen bromide
- bromopropionic acid
- acid
- reaction
- bromopropionic
- 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.)
- Pending
Links
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing beta-bromopropionic acid features that the acrylic acid is reacted on hydrogen bromide in grammol ratio of 1:(0.35-0.5) at 30-120 deg.C under the chromatographic control. Its reaction formula is CH2=CHCOOH+HBr-BrCH2COOH. Its advantages are simple operation, high output rate, and less environmental pollution.
Description
The invention relates to a preparation method of 3-bromopropionic acid.
The 3-bromopropionic acid is a chemical intermediate with wide application. The derivatives such as ester, acyl halide, amide and the like can be synthesized by taking the derivatives as starting raw materials; the active group bromine can perform a series of reactions and is mainly used in the fields of pesticides, medicines and the like. Such as fluazifop-p-butyl, furalaxyl and the like which are pesticides.
The synthesis of 3-bromopropionic acid mainly comprises two methods of acrylonitrile addition hydrolysis and 2-cyanoethanol halohydrolysis (handbook of fine organic chemical raw materials and intermediates, edited by Xuke, published by the chemical industry Press 1998).
The acrylonitrile addition hydrolysis reaction is as follows:
in the reaction, acrylonitrile is dropped into boiling hydrobromic acid, reflux reaction, cooling, filtering out water solution, extracting solid with solvent, filtering out solid, desolventizing filtrate and distilling to obtain the product. In the reaction process, equipment is seriously corroded due to higher temperature (130 ℃); and the operation is cumbersome.
The 2-cyanoethanol halohydrolysis reaction is as follows:
the reaction process is similar to the addition hydrolysis of acrylonitrile, and the problems of serious corrosion, complex operation and the like exist, and the raw materials are expensive.
The invention aims to provide a preparation method of 3-bromopropionic acid, which is simple and convenient to operate, has small influence on the environment and can realize industrial production.
The invention adopts a method for adding acrylic acid and hydrogen bromide, and the reaction formula is as follows:
1. the hydrogen bromide may be in different forms, and may be in the form of a gas or an aqueous solution. The production process has the best environmental compatibility and economy when gaseous hydrogen bromide is used.
2. The ratio of acrylic acid to hydrogen bromide is 1: 0.5-1: 3.5 (molar ratio, the same applies below), preferably 1: 1-1: 2.5; the temperature range is 30-120 ℃, wherein the optimal temperature is 50-65 ℃.
3. The process adopts chromatographic control.
The invention is further described below by way of examples.
The first embodiment is as follows: a stirrer, a thermometer and a vent (tail gas absorption) are arranged in a 5000ml reaction kettle, 3040 g (48 percent and 18 gram molecules) of hydrobromic acid and 655 g (99.00 percent and 9 gram molecules) of acrylic acid are added, the temperature is raised to 60 ℃, the reaction is kept for 4 hours, after the heat preservation is finished, the mixture is cooled, filtered and dried, 1278.6 g of 3-bromopropionic acid is obtained, the content is 98.00 percent, and the yield is 91.00 percent.
Example two: a stirrer, a thermometer, a gas inlet pipe and a vent (tail gas absorption) are arranged in a 1000ml reaction kettle, 364 g (99.00 percent and 5 g molecules) of acrylic acid is added, the temperature is raised to 50 ℃, hydrogen bromide gas is introduced, the temperature is controlled to be 50-65 ℃ in the process of introducing the hydrogen bromide gas, the ventilation quantity is about 530 g (6.5 g molecules), and after the reaction is finished, air is introduced to drive away excessive hydrogen bromide; sampling analysis shows that the content of the 3-bromopropionic acid is 96.70 percent, the yield is 751.6 g, and the yield is 95.00 percent.
Claims (5)
1. A preparation method of 3-bromopropionic acid is characterized by comprising the following steps:
the reaction is as follows: addition of acrylic acid to hydrogen bromide;
the reaction formula is as follows:
the ratio of acrylic acid to hydrogen bromide was: 1: 0.5-1: 3.5 (molar ratio, the same below);
the reaction temperature is as follows: 30 to 120 ℃.
2. A process for the preparation of 3-bromopropionic acid as claimed in claim 1, wherein the optimum ratio of acrylic acid to hydrogen bromide is: 1: 1 to 1: 2.5.
3. The process for producing 3-bromopropionic acid according to claim 1, wherein the optimum reaction temperature is: 50-65 ℃.
4. A process for the preparation of 3-bromopropionic acid as claimed in claim 1, wherein the hydrogen bromide is in a form selected from a gas and an aqueous solution.
5. A process for the production of 3-bromopropionic acid as claimed in claims 1 and 4, characterized in that the production process is most environmentally compatible and economical when gaseous hydrogen bromide is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01108052 CN1365963A (en) | 2001-01-18 | 2001-01-18 | Process for preparing 3-bromopropionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01108052 CN1365963A (en) | 2001-01-18 | 2001-01-18 | Process for preparing 3-bromopropionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1365963A true CN1365963A (en) | 2002-08-28 |
Family
ID=4656941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01108052 Pending CN1365963A (en) | 2001-01-18 | 2001-01-18 | Process for preparing 3-bromopropionic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1365963A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159614A (en) * | 2011-12-14 | 2013-06-19 | 中化蓝天集团有限公司 | Method for preparing 3-fluoropropionic acid |
| CN104447346A (en) * | 2014-12-09 | 2015-03-25 | 曲阜德禄生物科技有限公司 | Method for preparing 3-nitropropionic acid |
-
2001
- 2001-01-18 CN CN 01108052 patent/CN1365963A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159614A (en) * | 2011-12-14 | 2013-06-19 | 中化蓝天集团有限公司 | Method for preparing 3-fluoropropionic acid |
| CN104447346A (en) * | 2014-12-09 | 2015-03-25 | 曲阜德禄生物科技有限公司 | Method for preparing 3-nitropropionic acid |
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|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |