CN116425611A - Preparation method of meta-diphenylacetone and diphacinone sodium salt - Google Patents
Preparation method of meta-diphenylacetone and diphacinone sodium salt Download PDFInfo
- Publication number
- CN116425611A CN116425611A CN202310397318.7A CN202310397318A CN116425611A CN 116425611 A CN116425611 A CN 116425611A CN 202310397318 A CN202310397318 A CN 202310397318A CN 116425611 A CN116425611 A CN 116425611A
- Authority
- CN
- China
- Prior art keywords
- lactate
- solution
- preparation
- meta
- sodium salt
- 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 17
- TURJLPVZRPWSJO-UHFFFAOYSA-N sodium;2-(2,2-diphenylacetyl)inden-2-ide-1,3-dione Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)[C-]1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 TURJLPVZRPWSJO-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims abstract description 8
- -1 phenyl Grignard reagent Chemical class 0.000 claims abstract description 7
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 6
- RQKXFLUAQLDHMO-UHFFFAOYSA-N 1,1-diphenylpropane-1,2-diol Chemical compound C=1C=CC=CC=1C(O)(C(O)C)C1=CC=CC=C1 RQKXFLUAQLDHMO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006297 dehydration reaction Methods 0.000 claims abstract 3
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 8
- 229960001826 dimethylphthalate Drugs 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- DBNWBEGCONIRGQ-UHFFFAOYSA-N 1,1-diphenylpropan-2-one Chemical compound C=1C=CC=CC=1C(C(=O)C)C1=CC=CC=C1 DBNWBEGCONIRGQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 230000003113 alkalizing effect Effects 0.000 claims description 2
- 229940116333 ethyl lactate Drugs 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 claims 1
- 229940057867 methyl lactate Drugs 0.000 claims 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 claims 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical compound CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JYGLAHSAISAEAL-UHFFFAOYSA-N Diphenadione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JYGLAHSAISAEAL-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229960000267 diphenadione Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910000951 Aluminide Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 231100000086 high toxicity Toxicity 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- WFFZGYRTVIPBFN-UHFFFAOYSA-N 3h-indene-1,2-dione Chemical class C1=CC=C2C(=O)C(=O)CC2=C1 WFFZGYRTVIPBFN-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- UYNAFHNUGOEVFE-UHFFFAOYSA-M [Cl-].C1CCOC1.[Mg+]C1=CC=CC=C1 Chemical compound [Cl-].C1CCOC1.[Mg+]C1=CC=CC=C1 UYNAFHNUGOEVFE-UHFFFAOYSA-M 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VAFHGNONYSDSKH-UHFFFAOYSA-N ethyl 2-hydroxypropanoate oxolane Chemical compound C(C)OC(C(O)C)=O.O1CCCC1 VAFHGNONYSDSKH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 238000005887 phenylation reaction Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940124547 specific antidotes Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of organic synthetic chemistry and also belongs to the field of pesticides, and particularly relates to a preparation method of meta-diphenylacetone and diphacinone sodium salt. The invention provides a preparation method of vinylidene acetone, which comprises the following steps: carrying out format reaction on a phenyl Grignard reagent solution and a lactate solution to obtain 1, 1-diphenyl-1, 2-propanediol, namely an intermediate 1; and (3) carrying out dehydration reaction on the intermediate 1 and sulfuric acid solution to obtain the meta-diphenyl acetone. The invention can provide the preparation method of the vinylidene acetone, which has the advantages of convenient operation, simplified process, high yield, low production cost, less three wastes, environmental friendliness and convenient industrialized production.
Description
The application is a divisional application of 14 days of 2017, 06 month, 201710446450.7 and entitled "preparation process method of efficient environment-friendly diphacinone sodium salt".
Technical Field
The invention belongs to the field of organic synthetic chemistry and also belongs to the field of pesticides, and particularly relates to a preparation method of meta-diphenylacetone and diphacinone sodium salt.
Background
The diphacinone sodium salt (CAS: 42721-99-3) belongs to indandione compounds, is an anticoagulant rodenticide, has a much larger multiple oral toxicity than acute oral toxicity, and therefore has obvious cumulative toxicity effect, good deratization effect and specific antidote Vk1, is relatively safe to people and animals, and is widely popularized.
The early synthetic route of diphacinone sodium salt is mainly that diphacinone is obtained by brominating or chloridizing from phenylpropionic acid, then is phenylated, is cyclized with dimethyl phthalate, is acidified to obtain diphacinone, and then is converted into diphacinone sodium salt, and the technological route is as follows:
upjohn, USA, uses the method of phenylacetone bromination; the Moscow university report reports that the reaction was driven by chlorination with sub-chloride instead of liquid bromine. The process route is longer, so the production cost is high, the yield is low, a large amount of wastewater can be generated in the process route, and the damage to equipment is large.
In order to overcome the defects, a new process route is developed, namely, starting from acetone, monochloroacetone is generated by primary chlorination, then 1.1-trichloroacetone is obtained by secondary chlorination, 1.1-trichloroisopropanol is obtained by reduction, and then the partial diphenyl acetone is generated by phenylation, and finally the diphacin sodium salt is obtained by cyclization, wherein the reaction process route is as follows:
the process route has low price of raw materials, is easy to obtain, is improved compared with the process obtained in the early stage, but the route is still longer; the chlorine is used, the danger is high, the requirements and the damage to equipment are high, and particularly when 1.1.1-trichloroacetone is prepared, the side reaction is relatively high, the product purity is low, and the purification is not easy; the aluminum isopropoxide, aluminum trichloride and the like are used in a large amount, and the wastewater is large and does not meet the environmental protection requirement.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the preparation method of the sodium salt of the vinylidene fluoride and the diphacinone, which has the advantages of convenient operation, simplified process, high yield, low production cost, less three wastes, environmental friendliness and convenient industrial production.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the preparation process of efficient environment friendly diphacinone sodium salt includes the following steps:
the method comprises the following steps:
step one: phenyl grignard reagent reacts with lactate to generate 1, 1-diphenyl-1, 2-propanediol, namely an intermediate 1;
step two: dehydrating the intermediate 1 obtained in the step one in sulfuric acid, and synthesizing to obtain the meta-diphenyl acetone;
step three: condensing the meta-diphenyl acetone obtained in the first step with dimethyl phthalate, then alkalizing with sodium hydroxide, and finally obtaining diphacinone sodium salt.
Due to the application of the technical scheme, the invention has the following beneficial technical effects: the technical scheme has the advantages of short process route, simplified production steps, higher efficiency, simple and easily obtained raw materials, low production cost and low price; in addition, raw materials such as chlorine or liquid bromine which have high requirements on equipment and are greatly damaged are avoided, and meanwhile, high-toxicity benzene-obtaining reagents, aluminides and the like are not used, so that the method is safer and more environment-friendly.
Due to the application of the technical scheme, the invention has the following beneficial technical effects: the technical scheme has the advantages of short process route, simplified production steps, higher efficiency, simple and easily obtained raw materials, low production cost and low price; in addition, raw materials such as chlorine or liquid bromine which have high requirements on equipment and are greatly damaged are avoided, and meanwhile, high-toxicity benzene-obtaining reagents, aluminides and the like are not used, so that the method is safer and more environment-friendly.
Drawings
The present invention will be described in further detail with reference to specific examples.
Fig. 1 is a schematic diagram of the preparation steps of the diphacinone sodium salt according to the present invention.
Detailed Description
The invention will be described in further detail with reference to the accompanying drawings and specific examples.
1. Preparation of meta-diphenylpropanone
Test materials:
| name of the name | Molecular weight | Feeding amount | Molar ratio of | Purity of |
| Sodium methoxide | 54.02 | 21g | 1.3 | 30％ |
| Dimethyl phthalate | 194.18 | 19g | 1.02 | 99％ |
| Meta-diphenylpropanone | 210.27 | 20g | 1 | 95％ |
| Toluene (toluene) | 92.14 | 250ml | ||
| Water and its preparation method | 2000ml | |||
| Sodium hydroxide | / |
The test steps are as follows:
1. introducing nitrogen into a dry three-neck flask with a capacity of 2000 ml, replacing the flask back and forth for three times, then adding 600 ml of phenyl magnesium chloride tetrahydrofuran solution with a concentration of 1.6mol/L, placing the solution in an ice-water bath, and controlling the internal temperature to be about 0 ℃;
2. dropwise adding an ethyl lactate-tetrahydrofuran solution, 82.5 ml of ethyl lactate and 100 ml of tetrahydrofuran under stirring, removing the ice bath after the dropwise adding is finished, replacing the ice bath with an oil bath, slowly heating to a reflux temperature, and refluxing for 2 hours;
3. the oil bath was removed, cooled to 0 ℃ with ice water, and a 10% dilute hydrochloric acid solution (approximately 1.8 moles, 165 ml of concentrated hydrochloric acid and 400 ml of water) was added dropwise with rapid stirring;
4. separating, separating an organic layer, washing an aqueous phase twice with 150 ml of dichloromethane, combining the organic phases, drying and concentrating;
5. adding 20% sulfuric acid (75 ml of concentrated sulfuric acid+225 ml of water by volume) into the obtained concentrated phase, heating to 90 ℃ and refluxing for 3-4 hours, and separating liquid;
6. adding 100 ml of water into the organic phase, adjusting pH to 7 by using liquid alkali, washing with water, and concentrating the obtained organic phase to obtain a viscous product;
7. methanol is recrystallized to obtain white solid, namely the meta-diphenyl acetone.
2. Preparation of diphacinone sodium salt
Test materials:
| name of the name | Molecular weight | Feeding amount | Molar ratio of | Purity of |
| Sodium methoxide | 54.02 | 21g | 1.3 | 30％ |
| Dimethyl phthalate | 194.18 | 19g | 1.02 | 99％ |
| Meta-diphenylpropanone | 210.27 | 20g | 1 | 95％ |
| Toluene (toluene) | 92.14 | 250ml | ||
| Water and its preparation method | 2000ml | |||
| Hydrogen oxidationSodium salt | / |
The test steps are as follows:
1. setting up a distillation device in a 500 milliliter three-mouth bottle with a mechanical stirring device;
2. adding 21 g of sodium methoxide and 100 ml of toluene, stirring, removing methanol at normal pressure, forming milky sodium methoxide suspension after methanol removal, and cooling to below 100 ℃;
3. with stirring, the mixture was poured into a solution of dimethyl phthalate and toluene (dimethyl phthalate 19 g and 50 ml toluene);
4. heating to internal temperature of 110 ℃, slowly dropwise adding the solution of the vinylidene acetone and the toluene (20 g of the vinylidene acetone and 100 ml of toluene) for about 3-4 hours, controlling the internal temperature of 110 ℃, evaporating a small amount of methanol midway, and preserving the temperature of 110 ℃ for 1 hour after dropwise adding;
5. cooling to 80 ℃, adding 25 ml of 2% alkaline water, stirring for 30 minutes at 80 ℃, cooling to 20 ℃, filtering, rinsing a filter cake with water, pumping and drying to finally obtain the diphacinone sodium salt.
The foregoing is merely a specific application example of the present invention, and the protection scope of the present invention is not limited in any way. All technical schemes formed by equivalent transformation or equivalent substitution fall within the protection scope of the invention.
Claims (8)
1. A preparation method of the partial diphenyl acetone is characterized by comprising the following steps:
dripping lactate solution into phenyl Grignard reagent solution at 0deg.C, and heating for reflux; the phenyl Grignard reagent in the phenyl Grignard reagent solution is phenyl magnesium chloride;
after the reflux is completed, dropwise adding a dilute hydrochloric acid solution at the temperature of 0 ℃ for first liquid separation treatment to obtain a first organic phase;
carrying out first concentration on the first organic phase to obtain 1, 1-diphenyl-1, 2-propanediol, namely an intermediate 1;
carrying out dehydration reaction on the intermediate 1 and sulfuric acid solution, and then carrying out second liquid separation treatment to obtain a second organic phase;
washing the second organic phase with water and concentrating the second organic phase to obtain the partial diphenyl acetone;
2. the preparation method according to claim 1, wherein the solvent of the phenyl grignard reagent solution is tetrahydrofuran, and the molar concentration is 1.6mol/L.
3. The method of claim 1, wherein the lactate in the lactate solution is ethyl lactate, methyl lactate, propyl lactate, isopropyl lactate or butyl lactate.
4. A method according to claim 1 or 3, wherein the solvent of the lactate solution is tetrahydrofuran; the volume ratio of the lactate to the tetrahydrofuran in the lactate solution is 82.5:100.
5. the method of claim 1, wherein the reflux time is 2 hours.
6. The method of claim 1, wherein the sulfuric acid solution has a concentration of 20%.
7. The method according to claim 1 or 6, wherein the dehydration reaction is carried out at a temperature of 90 ℃ for 3 to 4 hours.
8. The preparation method of the efficient environment-friendly diphacinone sodium salt is characterized by comprising the following steps:
the process according to any one of claims 1 to 7, wherein the process comprises preparing the product of the process to obtain the product of the process;
after condensation reaction of the meta-diphenyl acetone and dimethyl phthalate, alkalizing the meta-diphenyl acetone and dimethyl phthalate by sodium hydroxide to obtain the diphacinone sodium salt;
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310397318.7A CN116425611A (en) | 2017-06-14 | 2017-06-14 | Preparation method of meta-diphenylacetone and diphacinone sodium salt |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310397318.7A CN116425611A (en) | 2017-06-14 | 2017-06-14 | Preparation method of meta-diphenylacetone and diphacinone sodium salt |
| CN201710446450.7A CN107253906A (en) | 2017-06-14 | 2017-06-14 | A kind of high-efficiency environment friendly diphacinone-Na process of preparing |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710446450.7A Division CN107253906A (en) | 2017-06-14 | 2017-06-14 | A kind of high-efficiency environment friendly diphacinone-Na process of preparing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116425611A true CN116425611A (en) | 2023-07-14 |
Family
ID=60023260
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710446450.7A Pending CN107253906A (en) | 2017-06-14 | 2017-06-14 | A kind of high-efficiency environment friendly diphacinone-Na process of preparing |
| CN202310397318.7A Pending CN116425611A (en) | 2017-06-14 | 2017-06-14 | Preparation method of meta-diphenylacetone and diphacinone sodium salt |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710446450.7A Pending CN107253906A (en) | 2017-06-14 | 2017-06-14 | A kind of high-efficiency environment friendly diphacinone-Na process of preparing |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN107253906A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111875484B (en) * | 2020-07-24 | 2021-04-23 | 张家港九力新材料科技有限公司 | Continuous production process of metadiphenylacetone |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091090C (en) * | 1999-04-09 | 2002-09-18 | 单承仪 | Process for synthesizing refined diphacinone |
| CN1089084C (en) * | 1999-07-27 | 2002-08-14 | 叶定岳 | Process for preparing sodium diphacinone from purified meta-diphenylpropanone |
-
2017
- 2017-06-14 CN CN201710446450.7A patent/CN107253906A/en active Pending
- 2017-06-14 CN CN202310397318.7A patent/CN116425611A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN107253906A (en) | 2017-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109232178B (en) | Novel method for preparing high-purity hydroxytyrosol | |
| CN106008295B (en) | A kind of preparation method of the alkylthio group toluene of 2 halo 6 | |
| CN108715574A (en) | A method of synthesis '-biphenyl diphenol | |
| CN103880676B (en) | A kind of preparation method of dodecyl nipagin ester | |
| CN116425611A (en) | Preparation method of meta-diphenylacetone and diphacinone sodium salt | |
| CN107473948B (en) | Synthetic method for preparing 3, 5-dichloro-2-pentanone from ethyl acetoacetate | |
| CN108947800B (en) | Synthesis method of (1S) -4, 5-dimethoxy-1- (carbonylaminomethyl) benzocyclobutane | |
| CN102516133A (en) | Preparation method of methanesulfonic acid derivative | |
| CN109320468B (en) | Method for mild preparation of benzo [ a ] phenazine compound | |
| CN103319316A (en) | Green preparation method of dihydroxy dibutyl ether | |
| CN104326989B (en) | The preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine | |
| CN104447433A (en) | Method for synthesizing 3,5-dibromoparatoluensulfonyl chloride | |
| JP2009512630A (en) | Preparation method of epoxy compound and aldehyde | |
| CN112707807B (en) | Preparation method of 4, 5-difluorophthalic acid | |
| CN109485564B (en) | Novel method for preparing bifenthrin | |
| CN108069832B (en) | Preparation method of 2,3,5, 6-tetrafluorophenol | |
| CN109912396B (en) | Synthetic method of 3-bromo-4-fluorobenzaldehyde | |
| CN112142579A (en) | Preparation process of 2-hydroxy-4-methoxybenzophenone | |
| CN107473951A (en) | A kind of 1,3 indandione sodium salt preparation methods | |
| US2513140A (en) | 3-thienylacetic acid | |
| CN102557947B (en) | Method for preparing 5-bromoacetylsalicylic acid methyl ester | |
| CN110452097B (en) | Preparation method of 1-hydroxypyrene | |
| CN109438360B (en) | Preparation method of creatinine | |
| CN107501069B (en) | Preparation method of diphacinone sodium salt | |
| CN108017610B (en) | Preparation method of vitamin E |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |