CN102442922A - Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction - Google Patents
Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction Download PDFInfo
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- CN102442922A CN102442922A CN2011102465300A CN201110246530A CN102442922A CN 102442922 A CN102442922 A CN 102442922A CN 2011102465300 A CN2011102465300 A CN 2011102465300A CN 201110246530 A CN201110246530 A CN 201110246530A CN 102442922 A CN102442922 A CN 102442922A
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- BFAROIHYSUNBOT-UHFFFAOYSA-N CCOCN(C(CCl)=O)c1ccccc1 Chemical compound CCOCN(C(CCl)=O)c1ccccc1 BFAROIHYSUNBOT-UHFFFAOYSA-N 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N CCc1cccc(C)c1N(COCC)C(CCl)=O Chemical compound CCc1cccc(C)c1N(COCC)C(CCl)=O VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- SMINYPCTNJDYGK-UHFFFAOYSA-N CCc1cccc(C)c1NC(CCl)=O Chemical compound CCc1cccc(C)c1NC(CCl)=O SMINYPCTNJDYGK-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N O=C(CCl)Nc1ccccc1 Chemical compound O=C(CCl)Nc1ccccc1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the technical field of organic synthesis and particularly relates to a method for carrying out a chloromethyl alkyl ether nitrogen-alkylation reaction by taking powder alkali with specified granularity as an acid-binding agent. Compared with a method for taking corresponding aqueous water as the acid-binding agent, the method disclosed by the invention has the characteristics of simleness, convenience and high yield. The method comprises the following steps of: dispersing acid amide and the power alkali as the acid-binding agent into a solvent, wherein in a reaction system, the concentration of the acid amide is 100-300mg/Ml and the mol ratio of the acid amide to the acid-binding agent is (1:1.5)-(1:3); controlling the temperature of the reaction system to be 10-20DEG C; dropping chloromethyl alkyl ether by stirring, wherein the mol ratio of the acid amide to the chloromethyl alkyl ether is (1:1)-(1:2); after dropping, controlling the temperature of the reaction system not to be higher than 30DEG C and reacting for 10-30 minutes; reacting at the temperature of 30-40DEG C for 15-30 minutes and finishing reaction; and adding water for washing a product to dissolve the generated salt; and after liquid separation, concentrating an organic phase to obtain alkoxy methylene-substituted acid amide.
Description
Technical field
The invention belongs to technical field of organic synthesis; Be specifically related to a kind of powder alkali that adopts specified particle size and carry out the method for the azane glycosylation reaction of chloromethyl alkyl oxide as acid binding agent; Compare as the method for acid binding agent with the aqueous solution of corresponding alkali, the inventive method has easy, the characteristics that productive rate is high.
Background technology
The chloromethyl alkyl oxide is one type of very active organic synthesis reagent, and common have chloromethyl methyl ether, chloromethyl ethyl ether, chloromethyl propyl ether and a chloromethyl n-butyl ether etc.Be widely used in all kinds of organic synthesis as protection base or reaction reagent; As basic as protection, the chloromethyl methyl ether is to use maximum hydroxyl protecting groups, generally under alkaline condition; Chloromethyl methyl ether and oxy-compound reaction, the hydroxyl behind the one-tenth ether obtains protection.Removing of this protection base is under acidic conditions, and example hydrochloric acid exists down, sloughs the protection base, and hydroxyl dissociates out again.
Frequent and amides reaction all contains the substituted methylene radical structure of alkoxyl group in the chemical structure like weedicide acetochlor, Butachlor technical 92 etc. as reaction reagent.Its preparation is that raw material and corresponding amide reaction realize with the chloromethyl alkyl oxide.Acid binding agent common in this reaction is sodium hydride, yellow soda ash, salt of wormwood, sodium hydroxide, Pottasium Hydroxide etc., in these acid binding agents, and the acid binding agent that sodium hydroxide is the most cheap beyond doubt, the application in industrial production is also extensive.Traditional synthesis technique adopts the acid binding agent of the sodium hydroxide (mass percent is 50%) of high density as reaction; The mass percent of general commercially available liquid caustic soda (being sodium hydroxide solution) is 42%; Add solid sodium hydroxide before use; The high density liquid caustic soda that is made into mass percent about 50% earlier reacts again, joins the alkali operation during this promptly produces.
For guaranteeing to react completely; Usually need to add big excessive sodium hydroxide, the mol ratio of acid amides and sodium hydroxide is generally about 1: 6, the sodium hydroxide of the big volume low-concentration of reaction residue; Can produce a large amount of pollutents on the industrial production, the consumption that reduces alkali is the target that this synthesis technique is pursued always.
The method that some bibliographical informations minimizing alkali consumptions have been arranged at present is like (Jilin Institute of Chemical Technology journal, 2001 such as Zhang Fusheng; 18; P14-16) condensation process in the acetochlor production is improved, using mass percent is that alternative 47% sodium hydroxide solution of 42% sodium hydroxide solution directly is used for producing, and has reduced the operation of compounding high concentration alkali; But Synthesis conversion is undesirable, and joint alkali effect is also not obvious.The problem that alkali charge is big is one of technology difficult problem of large weedicides such as the synthetic acetochlor of monochloromethyl-ether method, Butachlor technical 92.
Summary of the invention
The purpose of this invention is to provide a kind of method, it is to adopt the acid binding agent of the powder alkali of specified particle size as chloromethyl alkyl oxide azane glycosylation reaction, in order to improve the service efficiency of acid binding agent.
Reaction expression of the present invention is following:
R in the formula
1, R
2Represent substituting groups such as hydrogen, methyl, ethyl, propyl group, sec.-propyl, chlorine, bromine, nitro, R
3Representing the alkyl substituent of 1～6 carbon, can be that the straight chained alkyl substituting group also can be the branched-chain alkyl substituting group.
The method of powder alkali of in chloromethyl alkyl oxide azane glycosylation reaction, using of the present invention as acid binding agent; At first be that acid amides (1) and powder alkali acid binding agent (3) are distributed in an amount of solvent; Like toluene, YLENE, hexane, sherwood oil, ether, chloroform, methylene dichloride etc.; The concentration of acid amides is 100mg/mL～300mg/mL in the reaction system; The control temperature of reaction system is 10～20 ℃, stirs down and drips chloromethyl alkyl oxide (2), and the mol ratio of acid amides and chloromethyl alkyl oxide is 1: 1～1: 2; Dropwise back control temperature of reaction system and be not higher than 30 ℃, reaction 10～30min, and then under 30～40 ℃ of temperature, react 15～30min, reaction is accomplished; Add the salt dissolving that the water washing product makes generation, organic phase concentrates and obtains the substituted acid amides of alkoxyl group methylene radical (4) behind the separatory.
The mol ratio of used acid amides of the present invention and acid binding agent is 1: 1.5～1: 3, and optimum molar ratio is 1: 1.8～1: 2.
Powder alkali is the powder that is processed to less than 40 purpose sodium hydroxide, Pottasium Hydroxide, yellow soda ash or salt of wormwood, and the optimum grain-diameter scope is 60～100 orders, and concrete working method is seen embodiment 1.Powder alkali acid binding agent can directly use; Also can be scattered in the inert solvent earlier and re-use; Inert solvent commonly used is toluene, YLENE, hexane, sherwood oil, ether, chloroform, methylene dichloride etc.; The mass concentration that is dispersed in the powder alkali acid binding agent in the inert solvent is 1%～80%, and the righttest mass concentration is 20%～30%.
The present invention adopts and carries out the azane glycosylation reaction less than 40 purpose powder alkali as acid binding agent, has the following advantages:
(1) compare as acid binding agent with the alkaline solution of identical mol ratio, present method can be brought up to productive rate more than 95% from 80%.
(2) compare with traditional method, the mol ratio of acid amides and alkali was reduced to minimum 1: 1.5 by 1: 6, and the acid amides that conversionization is 1 mole only consumes 1 mole alkali, and the residue alkali number significantly reduced after reaction was accomplished, and helped reducing the discharging of salkali waste.
(3) powder alkali feeds intake and has littler volume of material than liquid base, can improve the load that feeds intake of reaction vessel, improves plant factor.
(4) because the acid binding agent consumption reduces 4～5 times, the also corresponding reduction of production cost.
Embodiment
Control Example 1:6 times of quantity of fluid alkali is as the synthetic acetochlor of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, mass concentration is 50% aqueous sodium hydroxide solution 18g (0.23mol), stirs to add acid amides 8g (0.04mol) down; 15 ℃ of temperature; Stir down and drip chloromethyl ethyl ether 4.9g (0.05mol), controlled temperature is not higher than 30 ℃, about 15min of time; Continue insulation at 35 ℃ of reaction 20min, reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate acetochlor 9.7g (0.036mol), purity 95%, productive rate 90%.
Control Example 2:2 times of quantity of fluid alkali is as the synthetic acetochlor of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, mass concentration is 50% aqueous sodium hydroxide solution 6g (0.07mol), stirs to add acid amides 8g (0.04mol) down; 15 ℃ of temperature; Stir down and drip chloromethyl ethyl ether 4.9g (0.05mol), controlled temperature is not higher than 30 ℃, about 15min of time; Continue insulation at 35 ℃ of reaction 20min, reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate acetochlor, raw material transforms fully, separates residue acid amides raw material 0.9g, straight product 8.16g, productive rate 80% through silica gel column chromatography.
Embodiment 1: the preparation of powder alkali
The preparation of powder alkali has two kinds of methods, and the one, ball milled directly adds ball mill with solid alkali, is ground into suitable granularity, sieves, and keeps the powder alkali below 40 orders, and is subsequent use; The 2nd, liquid phase method joins solid alkali in the solvent, and like YLENE, toluene etc., mass ratio is a solid alkali: solvent=1: 10～1: 1, and adopt high-speed emulsifying machine (DE-100L type) to shear pulverizing, sealing was subsequent use after particle diameter was lower than 40 orders.
Embodiment 2:2 doubly measures powder alkali as the synthetic acetochlor of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 3g (0.07mol, 60～100 orders); Stir adding acid amides 8g (0.04mol) down, 15 ℃ of temperature stir and drip chloromethyl ethyl ether 4.9g (0.05mol) down; Controlled temperature is not higher than 30 ℃; About 15min of time continues insulation at 35 ℃ of reaction 20min, and reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate acetochlor 10.2g (0.038mol), purity 96%, productive rate 96%.
Embodiment 3:1.5 doubly measures powder alkali as the synthetic acetochlor of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 2.3g (0.057mol, 60～100 orders); Stir adding acid amides 8g (0.04mol) down, 15 ℃ of temperature stir and drip chloromethyl ethyl ether 4.9g (0.05mol) down; Controlled temperature is not higher than 30 ℃; About 15min of time continues insulation at 35 ℃ of reaction 20min, and reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate acetochlor, acid amides raw material residue 0.8%, quality product 10g, purity 96%, productive rate 95%.
Embodiment 4:3 doubly measures powder alkali as the synthetic acetochlor of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 3g (0.11mol, 60～100 orders); Stir adding acid amides 8g (0.04mol) down, 15 ℃ of temperature stir and drip chloromethyl ethyl ether 4.9g (0.05mol) down; Controlled temperature is not higher than 30 ℃; About 15min of time continues insulation at 35 ℃ of reaction 20min, and reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate acetochlor 10.2g (0.038mol), purity 96%, productive rate 96%.
Embodiment 5:2 doubly measures powder alkali as the synthetic Butachlor technical 92 of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 2.84g (0.07mol) stirs adding acid amides 8g (0.04mol) down; 15 ℃ of temperature; Stir down and drip chloromethyl ethyl ether 5.9g (0.05mol), controlled temperature is not higher than 30 ℃, about 15min of time; Continue insulation at 35 ℃ of reaction 20min, reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate Butachlor technical 92 11g (0.034mol), purity 96%, productive rate 95%.
Embodiment 6:2 doubly measures powder alkali as the synthetic Butachlor technical 92 of acid binding agent, and solvent is an ether
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add ether 30ml, solid sodium hydroxide powder 2.84g (0.07mol) stirs adding acid amides 8g (0.04mol) down; 15 ℃ of temperature; Stir down and drip chloromethyl ethyl ether 5.9g (0.05mol), controlled temperature is not higher than 30 ℃, about 15min of time; Continue insulation at 35 ℃ of reaction 20min, reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate Butachlor technical 92 11g (0.034mol), purity 96%, productive rate 95%.
Embodiment 7: powdered sodium carbonate is as the synthetic Butachlor technical 92 of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add toluene 30ml, solid sodium carbonate powder 7.5g (0.07mol) stirs adding acid amides 8g (0.04mol) down; 15 ℃ of temperature; Stir down and drip chloromethyl ethyl ether 5.9g (0.05mol), controlled temperature is not higher than 30 ℃, about 15min of time; Continue insulation at 35 ℃ of reaction 20min, reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate Butachlor technical 92 11g (0.034mol), purity 96%, productive rate 95%.
Embodiment 8:2 doubly measures powder alkali (being dispersed in the solvent) as the synthetic Butachlor technical 92 of acid binding agent
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 20ml, solid sodium hydroxide powder 2.84g (0.07mol, 60-100 order; Be dispersed in the 10mL YLENE), stir adding acid amides 8g (0.04mol) down, 15 ℃ of temperature; Stir down and drip chloromethyl ethyl ether 5.9g (0.05mol), controlled temperature is not higher than 30 ℃, about 15min of time; Continue insulation at 35 ℃ of reaction 20min, reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate product Butachlor technical 92 11g (0.034mol), purity 96%, productive rate 95%.
Embodiment 9:2 doubly measures powder alkali as the synthetic unsubstituted acid amides (R of acid binding agent
1=R
2=H)
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 3g (0.07mol, 60-100 order); Stir adding acid amides 6.8g (0.04mol) down, 15 ℃ of temperature stir and drip chloromethyl ethyl ether 4.9g (0.05mol) down; Controlled temperature is not higher than 30 ℃; About 15min of time continues insulation at 35 ℃ of reaction 20min, and reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate no substituted amide 8.7g (0.038mol), purity 95%, productive rate 97%.
Embodiment 10:2 doubly measures powder alkali as the synthetic amide chloride (R of acid binding agent
1=R
2=Cl)
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 3g (0.07mol, 60～100 orders); Stir adding acid amides 9.5g (0.04mol) down, 15 ℃ of temperature stir and drip chloromethyl ethyl ether 4.9g (0.05mol) down; Controlled temperature is not higher than 30 ℃; About 15min of time continues insulation at 35 ℃ of reaction 20min, and reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate no substituted amide 11.3g (0.038mol), purity 95%, productive rate 96%.
Embodiment 11:2 doubly measures powder alkali as the synthetic dinitrobenzene substituted amide (R of acid binding agent
1=R
2=NO
2)
In having the 100ml three-necked flask of TM, constant pressure funnel, mechanical stirrer, add YLENE 30ml, solid sodium hydroxide powder 3g (0.07mol, 60～100 orders); Stir adding acid amides 10.4g (0.04mol) down, 15 ℃ of temperature stir and drip chloromethyl ethyl ether 4.9g (0.05mol) down; Controlled temperature is not higher than 30 ℃; About 15min of time continues insulation at 35 ℃ of reaction 20min, and reaction is accomplished.Add the 10ml water washing, separatory, organic phase concentrate no substituted amide 12.1g (0.038mol), purity 96%, productive rate 96%.
Claims (9)
1. in chloromethyl alkyl oxide azane glycosylation reaction, use the method for powder alkali as acid binding agent for one kind, its step is following:
1) at first be that acid amides (1) and powder alkali acid binding agent (3) are distributed in the solvent, the concentration of acid amides is 100mg/mL～300mg/mL in the reaction system, and the mol ratio of acid amides and acid binding agent is 1: 1.5～1: 3;
2) the control temperature of reaction system is 10～20 ℃, stirs down and drips chloromethyl alkyl oxide (2), and the mol ratio of acid amides and chloromethyl alkyl oxide is 1: 1～1: 2;
3) dropwise back control temperature of reaction system and be not higher than 30 ℃, reaction 10～30min; And then under 30～40 ℃ of temperature, react 15～30min, reaction is accomplished;
4) add the salt dissolving that the water washing product makes generation, organic phase concentrates and obtains the substituted acid amides of alkoxyl group methylene radical (4) behind the separatory; Its reaction formula is following,
R
1, R
2Be hydrogen, methyl, ethyl, propyl group, sec.-propyl, chlorine, bromine or nitro substituent; R
3It is the alkyl substituent of 1～6 carbon.
2. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 1, it is characterized in that: solvent is toluene, YLENE, hexane, sherwood oil, ether, chloroform or methylene dichloride.
3. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 1, it is characterized in that: powder alkali is the powder that is processed to less than 40 purpose sodium hydroxide, Pottasium Hydroxide, yellow soda ash or salt of wormwood.
4. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 1, it is characterized in that: the optimum size scope of powder alkali is 60～100 orders.
5. a kind of method of in chloromethyl alkyl oxide azane glycosylation reaction, using powder alkali as acid binding agent as claimed in claim 1, it is characterized in that: powder alkali acid binding agent directly uses, or is scattered in the inert solvent and uses.
6. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 5, it is characterized in that: inert solvent is toluene, YLENE, hexane, sherwood oil, ether, chloroform or methylene dichloride.
7. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 5, it is characterized in that: the mass concentration that is dispersed in powder alkali acid binding agent in the inert solvent is between 1%～80%.
8. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 7, it is characterized in that: the mass concentration that is dispersed in powder alkali acid binding agent in the inert solvent is 20%～30%.
9. a kind of method of powder alkali as acid binding agent of in chloromethyl alkyl oxide azane glycosylation reaction, using as claimed in claim 1, it is characterized in that: the mol ratio of acid amides and acid binding agent is: 1: 1.8～1: 2.
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| CN2011102465300A CN102442922A (en) | 2011-08-26 | 2011-08-26 | Method for taking powder alkali as acid-binding agent in chloromethyl alkyl ether nitrogen-alkylation reaction |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106674041A (en) * | 2016-12-19 | 2017-05-17 | 马鞍山中创环保科技有限公司 | Preparation method of acetochlor by employing ion exchange fiber as industrial acid-binding agent |
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| CN87101526A (en) * | 1987-03-31 | 1988-11-23 | 化工部沈阳化工研究院 | A kind of method of synthetic Butachlor technical 92 |
| US4919709A (en) * | 1983-01-25 | 1990-04-24 | Ciba-Geigy Corporation | N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2,6-dimethylaniline as herbicide |
| US5002606A (en) * | 1981-10-16 | 1991-03-26 | Ciba-Geigy Corporation | Optically active N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline as herbicide |
| CN101367746A (en) * | 2008-10-07 | 2009-02-18 | 南京工业大学 | Novel method for synthesis of (S)-propisochlor |
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2011
- 2011-08-26 CN CN2011102465300A patent/CN102442922A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412855A (en) * | 1972-02-07 | 1983-11-01 | Ciba-Geigy Corporation | 2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2",6"-dimethyl-acetanilide as long term weed killers |
| US5002606A (en) * | 1981-10-16 | 1991-03-26 | Ciba-Geigy Corporation | Optically active N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline as herbicide |
| US4919709A (en) * | 1983-01-25 | 1990-04-24 | Ciba-Geigy Corporation | N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2,6-dimethylaniline as herbicide |
| CN87101526A (en) * | 1987-03-31 | 1988-11-23 | 化工部沈阳化工研究院 | A kind of method of synthetic Butachlor technical 92 |
| CN101367746A (en) * | 2008-10-07 | 2009-02-18 | 南京工业大学 | Novel method for synthesis of (S)-propisochlor |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106674041A (en) * | 2016-12-19 | 2017-05-17 | 马鞍山中创环保科技有限公司 | Preparation method of acetochlor by employing ion exchange fiber as industrial acid-binding agent |
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Application publication date: 20120509 |