CN105886557A - Preparation method of phenoxypropionic acid - Google Patents
Preparation method of phenoxypropionic acid Download PDFInfo
- Publication number
- CN105886557A CN105886557A CN201510702135.7A CN201510702135A CN105886557A CN 105886557 A CN105886557 A CN 105886557A CN 201510702135 A CN201510702135 A CN 201510702135A CN 105886557 A CN105886557 A CN 105886557A
- Authority
- CN
- China
- Prior art keywords
- preparation
- hours
- seed
- propionic acid
- phenoxy propionic
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 241000238633 Odonata Species 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- AQIHDXGKQHFBNW-ZCFIWIBFSA-N (2r)-2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-ZCFIWIBFSA-N 0.000 claims description 3
- 238000010564 aerobic fermentation Methods 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000003795 desorption Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000002054 inoculum Substances 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 238000001179 sorption measurement Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 2
- 238000001514 detection method Methods 0.000 claims 1
- 238000005374 membrane filtration Methods 0.000 claims 1
- 229910052573 porcelain Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- SXERGJJQSKIUIC-SSDOTTSWSA-N (2r)-2-phenoxypropanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC=C1 SXERGJJQSKIUIC-SSDOTTSWSA-N 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000000855 fermentation Methods 0.000 abstract description 2
- 230000004151 fermentation Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 6
- 239000004009 herbicide Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 241000235342 Saccharomycetes Species 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GXEMMZPHKGLVPF-UHFFFAOYSA-N 2-hydroxy-2-phenoxypropanoic acid Chemical compound OC(=O)C(O)(C)OC1=CC=CC=C1 GXEMMZPHKGLVPF-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a preparation method of phenoxypropionic acid. The phenoxypropionic acid is prepared from R-2-phenoxypropionic acid through fermentation by virtue of candida-1. The preparation method disclosed by the invention is low in content of by-products and high in yield; and the purity of a finished product (the phenoxypropionic acid) can achieve 99.5% or above.
Description
Technical field
The present invention relates to the preparation method of a kind of R-4-hydroxyl-2-phenoxy propionic acid, belong to the synthesis system of pesticide intermediate
Standby technical field.
Background technology
China is a large agricultural country, and the consumption of agricultural chemicals is very big, and herbicide is as the important set of modern agricultural systemof production
Point, it is means the most reliable, most economical in farmland weeding technology.But, traditional herbicide is because its toxicity is big, efficiency is low, use
Dose is big, effect on environment is the most progressively eliminated very greatly.Therefore, herbicide is had higher requirement by modern: efficiently,
Low toxicity.The most in succession develop a series of herbicide such as diphenyl ether and phenoxy propionic acid class, sulfonylureas and imidazolone type, contain
The ureas of pyridine ring, pyridazine class etc..Phenoxy propionic acid compounds has efficiently, low toxicity, herbicidal spectrum wide, selectivity is high, use the phase
Long, to the succession crop feature such as safely, be one of performance is best up to now herbicide.
The method that existing R-4-hydroxyl-2-phenoxy propionic acid typically uses chemical synthesis, its course of reaction generates a large amount of secondary
Product, and be difficult to remove, have a strong impact on purification and the productivity of target product；Some method reaction time is long, and total recovery is on the low side；
Also some method needs to use catalyst, severe reaction conditions, and production cost is high, is not suitable for industrial production.
Summary of the invention
In order to solve above technical problem, the invention provides and a kind of utilize microbe fermentation method to prepare phenoxy propionic acid
Method.
The preparation method of the present invention is as follows:
Take false dragonfly silk yeast-1 bacterial classification, access in malt extract medium and carry out shake flask training under conditions of temperature 37 ± 1 DEG C
Supporting 8～24 hours preparation seed liquor, the seed liquor after cultivating accesses first class seed pot and cultivates 24 hours, adds secondary seed afterwards
Tank is cultivated 24 hours, and its training method is that conventional saccharomycete is cultivated.
Taking R-2-phenoxy propionic acid and be configured to 25-30% solution, the inoculum concentration by 10% accesses false-1 two grade of kind of dragonfly silk yeast
Sub-liquid, 35-38 DEG C of aerobic fermentation 3-5 days, rear add hydrochloric acid acidifying, tunes pH value is 2.0-3.0, and efficient liquid phase detects R-4-hydroxyl
After base-2-phenoxy propionic acid purity is more than 90%, first with ceramic membrane filter, activated carbon decolorizing, then bag type filtering machine filtration, macropore
Resin adsorption, after ammoniacal liquor desorption, 0.22 μm organic film secondary filter, rear condensing crystallizing, centrifugal drying.
Described false dragonfly silk saccharomycete-1 is self-sizing bacterial classification, and its preserving number is CGMCC No.10734.
The present invention uses false dragonfly silk yeast-1 bacterium of oneself seed selection, prepares R-4-with R-2-phenoxy propionic acid for fermenting raw materials
Hydroxyl-2-phenoxy propionic acid, whole process byproduct is few, pollutes few, and yield is high, be prepared as the purity of product up to 99.5% with
On.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is further illustrated.
Embodiment 1
Take false dragonfly silk yeast-1 bacterial classification, access in malt extract medium and carry out shake flask training under conditions of temperature 37 ± 1 DEG C
Supporting 8～24 hours preparation seed liquor, the seed liquor after cultivating accesses first class seed pot and cultivates 24 hours, adds secondary seed afterwards
Tank is cultivated 24 hours, and its training method is that conventional saccharomycete is cultivated.
Taking R-2-phenoxy propionic acid and be configured to 25-30% solution, the inoculum concentration by 10% accesses false-1 two grade of kind of dragonfly silk yeast
Sub-liquid, 35-38 DEG C of aerobic fermentation 3-5 days, rear add hydrochloric acid acidifying, tunes pH value is 2.0-3.0, and efficient liquid phase detects R-4-hydroxyl
After base-2-phenoxy propionic acid purity is more than 90%, first with ceramic membrane filter, activated carbon decolorizing, then bag type filtering machine filtration, macropore
Resin adsorption, after ammoniacal liquor desorption, 0.22 μm organic film secondary filter, rear condensing crystallizing, centrifugal drying.It is pure that efficient liquid phase detects it
Degree is 99.8%.
Claims (1)
1. the preparation method of a phenoxy propionic acid, it is characterised in that comprise the steps: to take false dragonfly silk yeast-1 bacterial classification, connect
Enter malt extract medium is carried out under conditions of temperature 37 ± 1 DEG C Shaking culture 8～24 hours preparation seed liquor, after cultivating
Seed liquor access first class seed pot and cultivate 24 hours, the rear secondary seed tank that accesses is further cultured for 24 hours；Take R-2-phenoxy group third
Acid is configured to 25-30% solution, and the inoculum concentration by 10% accesses secondary seed solution, 35-38 DEG C of aerobic fermentation 3-5 days, adds salt afterwards
Acid acidifying, tune pH value is 2.0-3.0, after efficient liquid phase detection R-4-hydroxyl-2-phenoxy propionic acid purity is more than 90%, first with pottery
Porcelain membrane filtration, activated carbon decolorizing, then bag type filtering machine filter, macroporous resin adsorption, and after ammoniacal liquor desorption, 0.22 μm organic film is accurate
Filter, rear condensing crystallizing, centrifugal drying.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510702135.7A CN105886557A (en) | 2015-10-27 | 2015-10-27 | Preparation method of phenoxypropionic acid |
| CN201610676250.6A CN106119305B (en) | 2015-10-27 | 2016-08-17 | A kind of preparation method of phenoxy propionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510702135.7A CN105886557A (en) | 2015-10-27 | 2015-10-27 | Preparation method of phenoxypropionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105886557A true CN105886557A (en) | 2016-08-24 |
Family
ID=57002857
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510702135.7A Pending CN105886557A (en) | 2015-10-27 | 2015-10-27 | Preparation method of phenoxypropionic acid |
| CN201610676250.6A Active CN106119305B (en) | 2015-10-27 | 2016-08-17 | A kind of preparation method of phenoxy propionic acid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610676250.6A Active CN106119305B (en) | 2015-10-27 | 2016-08-17 | A kind of preparation method of phenoxy propionic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN105886557A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108486209A (en) * | 2018-03-22 | 2018-09-04 | 浙江工业大学 | A kind of method of high-flux fast screening high yield R-2- (4- hydroxyphenoxies) propionic acid bacterial strain |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3910024A1 (en) * | 1989-03-28 | 1990-10-11 | Basf Ag | METHOD FOR THE FERMENTATIVE PRODUCTION OF 2- (4-HYDROXIPENOXI-) PROPIONIC ACID |
| CN102020554A (en) * | 2010-11-12 | 2011-04-20 | 西北师范大学 | Synthesis method of 2-[4-(hydroxyphenoxy)] propionic acid |
-
2015
- 2015-10-27 CN CN201510702135.7A patent/CN105886557A/en active Pending
-
2016
- 2016-08-17 CN CN201610676250.6A patent/CN106119305B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108486209A (en) * | 2018-03-22 | 2018-09-04 | 浙江工业大学 | A kind of method of high-flux fast screening high yield R-2- (4- hydroxyphenoxies) propionic acid bacterial strain |
| CN108486209B (en) * | 2018-03-22 | 2022-03-18 | 浙江工业大学 | Method for rapidly screening (R) -2- (4-hydroxyphenoxy) propionic acid producing strains in high flux |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106119305B (en) | 2019-07-09 |
| CN106119305A (en) | 2016-11-16 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160824 |