CN106278969A - A kind of method of green syt 1 isothiocyanic acid base 2 chlorine 2 propylene - Google Patents
A kind of method of green syt 1 isothiocyanic acid base 2 chlorine 2 propylene Download PDFInfo
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- CN106278969A CN106278969A CN201610671412.7A CN201610671412A CN106278969A CN 106278969 A CN106278969 A CN 106278969A CN 201610671412 A CN201610671412 A CN 201610671412A CN 106278969 A CN106278969 A CN 106278969A
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- acid base
- chloro
- propene
- isothiocyanic acid
- rhodanate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
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Abstract
A kind of method that the invention discloses green syt 1 isothiocyanic acid base 2 chlorine 2 propylene, comprises the following steps: a) by rhodanate compounds and 2, and 3 dichloropropylenes are added to the water, temperature reaction；This rhodanate compounds is one or more the compositions in the salt compounds such as sodium rhodanate, ammonium thiocyanate, potassium thiocyanate and Calcium rhodanate；B), after having reacted, cooling is filtered；C) filter cake organic solvent drip washing；D) filtrate stratification, water layer is applied mechanically, and obtains the bed of material；E), after bed of material recycling design, decompression distillation obtains finished product.The present invention uses one kettle way to be directly synthesized high-quality 1 isothiocyanic acid base 2 chlorine 2 propylene.After having reacted, filtering out the salt that reaction generates, after filtrate layering, water layer can be applied mechanically the most repeatedly.Produce almost without waste water, provide new thinking for synthesizing 1 isothiocyanic acid base 2 chlorine 2 propylene green production, with ammonium chloride and potassium chloride etc. in the filter cake additionally reclaimed after synthesis, so the filter cake reclaimed can be as fertilizer, the discharge of minimizing solid waste.
Description
Technical field
The present invention relates to 1-isothiocyanic acid base-2-chloro-2-propene synthesis field, specifically a kind of green syt 1-different sulfur cyanogen
The method of acidic group-2-chloro-2-propene.
Background technology
1-isothiocyanic acid base-2-chloro-2-propene, its English name is: 2-chloro-3-isothiocyanato-
Prop-1-ene, CAS NO.: 14214-31-4, colourless liquid.
1-isothiocyanic acid base-2-chloro-2-propene is synthetic pesticide Diacloden, clothianidin, MTI-446, medicine ritonavir
Important intermediate.At present, the pesticides application such as Diacloden, clothianidin and MTI-446 is extensive, and the market demand increases year by year.Therefore
Intermediate 1-isothiocyanic acid base-2-chloro-2-propene also has high application prospect.
The synthetic method of the 1-isothiocyanic acid base-2-chloro-2-propene that present stage is main is:
Patent CN1401646 and CN201110356519 are with water as solvent, but reaction needs to add phase transfer catalysis
Agent, adds production cost；And reaction temperature is too low, causes reaction not exclusively, or the response time is long, causes yield
Low, product quality is low.And post processing is washed, or is directly discharged to Non-aqueous processing station and causes substantial amounts of waste water to produce, and has very
Big environmental protection pressure.
Patent is also with water as solvent, is simultaneously introduced phase transfer catalyst and potassium iodide, some other patent or document
In, generally use the organic solvents such as acetonitrile, acetone or ethanol to do reaction dissolvent, but these reactions are owing to organic solvent is to sulfur
The dissolubility of cyanate compounds is limited, although causing adding phase transfer catalyst, reaction effect is the most undesirable.Yield is low,
Quality is bad.Even some method also needs to extra high temperature to carry out isomerization, causes operation complexity.Therefore find one to produce
Product content is high, and yield is high, and the 1-isothiocyanic acid base-2-chloro-2-propene preparation method that waste water is few has the highest realistic meaning.
Summary of the invention
A kind of method that it is an object of the invention to provide green syt 1-isothiocyanic acid base-2-chloro-2-propene, to solve
The problem proposed in above-mentioned background technology.
For achieving the above object, the present invention provides following technical scheme:
A kind of method of green syt 1-isothiocyanic acid base-2-chloro-2-propene, comprises the following steps:
A) by rhodanate compounds and 2,3-dichloropropylene is added to the water, temperature reaction；This rhodanate compounds is
One or more compositions in the salt compounds such as sodium rhodanate, ammonium thiocyanate, potassium thiocyanate and Calcium rhodanate；
B), after having reacted, solid-liquid separation after cooling, is carried out；
C) filter cake organic solvent drip washing；
D) filtrate stratification, water layer is applied mechanically, and obtains the bed of material；
E), after bed of material recycling design, decompression distillation obtains finished product；
F) water layer is applied mechanically the most repeatedly, or by applying mechanically again after alkali or acid for adjusting pH value, or use solvent extraction.
As the further scheme of the present invention: step a) 2,3-dichloropropylene is 1:1.3-1 with the part by weight of water:
10.0；The amount of 2,3-dichloropropylene and the material of rhodanate compounds is than for 1:1.2-1:6.0.
As the further scheme of the present invention: the temperature heated up in step a) is 80-110 DEG C.
As the further scheme of the present invention: step b) has been reacted cooling temperature and has been 20-60 DEG C.
As the further scheme of the present invention: in step c), the organic solvent of drip washing filter cake is 1,2-dichloroethanes, second
Acetoacetic ester, toluene, chloroform, chlorobenzene or dichloromethane.
As the further scheme of the present invention: the organic solvent of drip washing filter cake and 2,3-dichloropropylene in step c)
Mass ratio is 0.5-0.7:1.
As the further scheme of the present invention: in step e), distillage temperature is 60-78 DEG C.
As the further scheme of the present invention: step f) acid is respectively hydrochloric acid, sulphuric acid or nitric acid；Alkali is sodium hydroxide, hydrogen
Potassium oxide, calcium hydroxide, sodium bicarbonate, sodium carbonate or potassium carbonate.
As the further scheme of the present invention: in step f), water layer uses solvent extraction, solvent for use is 1,2-bis-chloroethene
Alkane, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane.
As the further scheme of the present invention: step f) also includes the filter cake having reclaimed extraction operation.
Compared with prior art, the invention has the beneficial effects as follows:
The present invention uses one kettle way to be directly synthesized high-quality 1-isothiocyanic acid base-2-chloro-2-propene.After having reacted, filter out anti-
The salt that should generate, after filtrate layering, water layer can be applied mechanically the most repeatedly.Produce almost without waste water, for synthesis 1-isothiocyanic acid
Base-2-chloro-2-propene green produces and provides new thinking.With a large amount of ammonium chloride and chlorine in the filter cake additionally reclaimed after synthesis
Change potassium etc., so the filter cake reclaimed as fertilizer, can reduce the discharge of solid waste.
Detailed description of the invention
Below in conjunction with the embodiment of the present invention, the technical scheme in the embodiment of the present invention is clearly and completely described,
Obviously, described embodiment is only a part of embodiment of the present invention rather than whole embodiments.Based in the present invention
Embodiment, the every other embodiment that those of ordinary skill in the art are obtained under not making creative work premise, all
Belong to the scope of protection of the invention.
Embodiment 1
In the embodiment of the present invention, a kind of method of green syt 1-isothiocyanic acid base-2-chloro-2-propene, comprise the following steps:
A) by rhodanate compounds and 2,3-dichloropropylene is added to the water, and is warmed up to 80 DEG C and reacts, 2,3-dichloros third
Alkene is 1:1.3 with the part by weight of water；The amount of 2,3-dichloropropylene and the material of rhodanate compounds is than for 1:1.2；Its
In, this rhodanate compounds is the combination of sodium rhodanate, ammonium thiocyanate and potassium thiocyanate, and sodium rhodanate, ammonium thiocyanate
Extracting weight with potassium thiocyanate is random combine, and the weight after combination is the required total amount mating above-mentioned amount ratio.
B), after having reacted, carry out solid-liquid separation after cooling to 20 DEG C again, obtain filter cake；
C) filter cake organic solvent drip washing, and organic solvent and 2, the mass ratio of 3-dichloropropylene is 0.5:1, drip washing filter cake
Organic solvent is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane；
D) filtrate stratification, water layer is applied mechanically, and obtains the bed of material；
E), after bed of material recycling design, decompression distillation obtains finished product, and the temperature of distillage is 60 DEG C；
F) water layer is applied mechanically the most repeatedly, or by applying mechanically again after alkali or acid for adjusting pH value, or use solvent extraction, acid
It is respectively hydrochloric acid, sulphuric acid or nitric acid；Alkali is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium bicarbonate, sodium carbonate or potassium carbonate,
Solvent for use is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane.Finally reclaim recovery and complete extraction
It is taken as the filter cake of industry.
Embodiment 2
In the embodiment of the present invention, a kind of method of green syt 1-isothiocyanic acid base-2-chloro-2-propene, comprise the following steps:
A) by rhodanate compounds and 2,3-dichloropropylene is added to the water, and is warmed up to 95 DEG C and reacts, 2,3-dichloros third
Alkene is 1:5.65 with the part by weight of water；The amount of 2,3-dichloropropylene and the material of rhodanate compounds is than for 1:3.6；Its
In, this rhodanate compounds is the combination of sodium rhodanate, ammonium thiocyanate and potassium thiocyanate, and sodium rhodanate, ammonium thiocyanate
Extracting weight with potassium thiocyanate is random combine, and the weight after combination is the required total amount mating above-mentioned amount ratio.
B), after having reacted, carry out solid-liquid separation after cooling to 40 DEG C again, obtain filter cake；
C) filter cake organic solvent drip washing, and organic solvent and 2, the mass ratio of 3-dichloropropylene is 0.6:1, drip washing filter cake
Organic solvent is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane；
D) filtrate stratification, water layer is applied mechanically, and obtains the bed of material；
E), after bed of material recycling design, decompression distillation obtains finished product, and the temperature of distillage is 69 DEG C；
F) water layer is applied mechanically the most repeatedly, or by applying mechanically again after alkali or acid for adjusting pH value, or use solvent extraction, acid
It is respectively hydrochloric acid, sulphuric acid or nitric acid；Alkali is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium bicarbonate, sodium carbonate or potassium carbonate,
Solvent for use is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane.Finally reclaim recovery and complete extraction
It is taken as the filter cake of industry.
Embodiment 3
In the embodiment of the present invention, a kind of method of green syt 1-isothiocyanic acid base-2-chloro-2-propene, comprise the following steps:
A) by rhodanate compounds and 2,3-dichloropropylene is added to the water, and is warmed up to 110 DEG C and reacts, 2,3-dichloros third
Alkene is 1:10.0 with the part by weight of water；The amount of 2,3-dichloropropylene and the material of rhodanate compounds is than for 1:6.0；Its
In, this rhodanate compounds is the combination of sodium rhodanate, ammonium thiocyanate and potassium thiocyanate, and sodium rhodanate, ammonium thiocyanate
Extracting weight with potassium thiocyanate is random combine, and the weight after combination is the required total amount mating above-mentioned amount ratio.
B), after having reacted, carry out solid-liquid separation after cooling to 60 DEG C again, obtain filter cake；
C) filter cake organic solvent drip washing, and organic solvent and 2, the mass ratio of 3-dichloropropylene is 0.7:1, drip washing filter cake
Organic solvent is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane；
D) filtrate stratification, water layer is applied mechanically, and obtains the bed of material；
E), after bed of material recycling design, decompression distillation obtains finished product, and the temperature of distillage is 78 DEG C；
F) water layer is applied mechanically the most repeatedly, or by applying mechanically again after alkali or acid for adjusting pH value, or use solvent extraction, acid
It is respectively hydrochloric acid, sulphuric acid or nitric acid；Alkali is sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium bicarbonate, sodium carbonate or potassium carbonate,
Solvent for use is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or dichloromethane.Finally reclaim recovery and complete extraction
It is taken as the filter cake of industry.
Embodiment 4
By 250.0g sodium rhodanate, it is added in 180.0g water, is subsequently adding 2,3-dichloropropylene 166.5g, then heats to
105 DEG C of reactions.Insulation reaction 3 hours.It is cooled to 30 DEG C, has solid to separate out, filter, solid-liquid separation.Solid 50.0g bis-chloroethene
Alkane drip washing.Filtrate stratification.Water layer is applied mechanically.Bed of material recovered under reduced pressure dichloroethanes, the dichloroethanes of recovery applies mechanically, material in still
Intensification distillation obtains product 1-isothiocyanic acid base-2-chloro-2-propylene, 185.0g, content 99.6%, yield 92.5%.
Embodiment 5
By 121.6g rhodanate compounds, it is added in embodiment 4 water layer, is subsequently adding 2,3-dichloropropylene 166.5g, so
After be warming up to 105 DEG C of reactions.Insulation reaction 5 hours.It is cooled to 30 DEG C, has solid to separate out, filter, solid-liquid separation.Solid is real
Execute the dichloromethane reclaimed in example 4 and mend dichloromethane 70.0g drip washing altogether with new.Filtrate stratification.Water layer is applied mechanically.The bed of material subtracts
Pushing back receipts dichloromethane, the dichloromethane of recovery is applied mechanically, and in still, the material distillation that heats up again obtains product 1-isothiocyanic acid base-2-
Chloro-2-propylene, 192.0g, content 99.5%, yield 96.0%.
Embodiment 6
By 121.6g sodium rhodanate, it is added in embodiment 2 water layer, is subsequently adding 2,3-dichloropropylene 166.5g, then heats to
100 DEG C of reactions.Insulation reaction 5 hours.It is cooled to 30 DEG C, has solid to separate out, filter, solid-liquid separation.Solid returns with in embodiment 2
The dichloroethanes drip washing received.Filtrate stratification.Water layer is applied mechanically.Bed of material recovered under reduced pressure dichloroethanes, the dichloroethanes set of recovery
With, in still, the material distillation that heats up again obtains product 1-isothiocyanic acid base-2-chloro-2-propylene, 180.0g, content 99.2%, yield
90.0%。
Embodiment 7
250.0g ammonium thiocyanate is added in 180.0g water, is subsequently adding 2,3-dichloropropylene 166.5g, then heats to 105
DEG C reaction.Insulation reaction 3 hours.It is cooled to 30 DEG C, has solid to separate out, filter, solid-liquid separation.Solid 50.0g dichloroethanes
Drip washing.Filtrate stratification.Water layer 50.0g dichloroethanes extracts, and extraction dichloroethanes is incorporated to the bed of material, and water layer is down applied mechanically.
Bed of material recovered under reduced pressure dichloroethanes, the dichloroethanes of recovery applies mechanically, and in still, material intensification distillation obtains product 1-isothiocyanic acid
Base-2-chloro-2-propylene, 190.0g, content 99.6%, yield 95.0%.
Embodiment 8
60g ammonium thiocyanate and 60g potassium thiocyanate are added in embodiment 7 water layer, are subsequently adding 2,3-dichloropropylene 166.5g, so
After be warming up to 105 DEG C of reactions.Insulation reaction 5 hours.It is cooled to 30 DEG C, has solid to separate out, filter, solid-liquid separation.Solid is real
Execute the dichloromethane reclaimed in example 4 and mend dichloromethane 70.0g drip washing altogether with new.Filtrate stratification.Water layer is applied mechanically.The bed of material subtracts
Pushing back receipts dichloromethane, the dichloromethane of recovery is applied mechanically, and in still, the material distillation that heats up again obtains product 1-isothiocyanic acid base-2-
Chloro-2-propylene, 180.0g, content 99.3%, yield 90.0%.
For field technique personnel, it is clear that the invention is not restricted to the details of above-mentioned one exemplary embodiment, and without departing substantially from this
In the case of the spirit or essential attributes of invention, it is possible to realize the present invention in other specific forms.Therefore, no matter from which point
From the point of view of, embodiment all should be regarded as exemplary, and be nonrestrictive, the scope of the present invention is by claims
It not that described above limits, it is intended that all changes fallen in the implication of equivalency and scope of claim are included
In the present invention.
Although moreover, it will be appreciated that this specification is been described by according to embodiment, but the most each embodiment only wraps
Containing an independent technical scheme, this narrating mode of description is only that for clarity sake those skilled in the art should
Description can also be formed those skilled in the art through appropriately combined as an entirety, the technical scheme in each embodiment
May be appreciated other embodiments.
Claims (10)
1. the method for a green syt 1-isothiocyanic acid base-2-chloro-2-propene, it is characterised in that comprise the following steps:
A) by rhodanate compounds and 2,3-dichloropropylene is added to the water, temperature reaction；This rhodanate compounds is
One or more compositions in sodium rhodanate, ammonium thiocyanate, potassium thiocyanate and Calcium rhodanate；
B), after having reacted, solid-liquid separation after cooling, is carried out；
C) filter cake organic solvent drip washing；
D) filtrate stratification, water layer is applied mechanically, and obtains the bed of material；
E), after bed of material recycling design, decompression distillation obtains finished product.
F) water layer is applied mechanically the most repeatedly, or by applying mechanically again after alkali or acid for adjusting pH value, or use solvent extraction.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, the temperature heated up in step a) is 80-110 DEG C.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, step a) 2,3-dichloropropylene is 1:1.3-1:10.0 with the part by weight of water；2,3-dichloropropylene and Hydrogen thiocyanate salt
The amount of the material of compound is than for 1:1.2-1:6.0.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, step b) is reacted cooling temperature and has been 20-60 DEG C.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, in step c), the organic solvent of drip washing filter cake is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or two
Chloromethanes.
6. according to the method for a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene described in claim 1 or 4, its feature
Being, the organic solvent and 2 of drip washing filter cake in step c), the mass ratio of 3-dichloropropylene is 0.5-0.7:1.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, in step e), distillage temperature is 60-78 DEG C.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, in step f), acid is respectively hydrochloric acid, sulphuric acid or nitric acid；Alkali be sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium bicarbonate,
Sodium carbonate or potassium carbonate.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, in step f) water layer use solvent extraction, solvent for use is 1,2-dichloroethanes, ethyl acetate, toluene, chloroform, chlorobenzene or
Person's dichloromethane.
The method of a kind of green syt 1-isothiocyanic acid base-2-chloro-2-propene the most according to claim 1, its feature exists
In, step f) also includes the filter cake having reclaimed extraction operation.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110240555A (en) * | 2019-06-24 | 2019-09-17 | 宁夏贝利特生物科技有限公司 | A kind of synthetic method of 1- isothiocyanic acid base -2- chloro-2-propene |
| CN110498754A (en) * | 2018-10-19 | 2019-11-26 | 湖北中迅长青科技有限公司 | A kind of environment-friendly preparation method thereof of isothiocyano compound |
| CN110835325A (en) * | 2018-08-15 | 2020-02-25 | 海利尔药业集团股份有限公司 | Method for treating and recycling clothianidin production wastewater |
| CN111808005A (en) * | 2020-07-23 | 2020-10-23 | 岳阳景嘉化工有限公司 | Continuous synthesis method of 2-chloro-3-isothiocyanic acid-1-propylene |
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| EP0761649A2 (en) * | 1995-09-12 | 1997-03-12 | Takeda Chemical Industries, Ltd. | Process for producing isothiocyanate derivatives |
| EP1728787A1 (en) * | 2004-03-22 | 2006-12-06 | Toyo Kasei Kogyo Company Limited | Process for purification of 2-chloro-5-chloromethyl -1,3-thiazole |
| CN103502210A (en) * | 2011-04-26 | 2014-01-08 | 拜耳知识产权有限责任公司 | Process for preparing 2-chloroallyl thiocyanate and 2-chloroallyl isothiocyanate |
| CN105175298A (en) * | 2015-08-04 | 2015-12-23 | 山东省农药科学研究院 | Synthesis and refining method of thiamethoxam intermediate 2-chloroallyl isothiocyanate |
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| EP0761649A2 (en) * | 1995-09-12 | 1997-03-12 | Takeda Chemical Industries, Ltd. | Process for producing isothiocyanate derivatives |
| EP1728787A1 (en) * | 2004-03-22 | 2006-12-06 | Toyo Kasei Kogyo Company Limited | Process for purification of 2-chloro-5-chloromethyl -1,3-thiazole |
| CN103502210A (en) * | 2011-04-26 | 2014-01-08 | 拜耳知识产权有限责任公司 | Process for preparing 2-chloroallyl thiocyanate and 2-chloroallyl isothiocyanate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110835325A (en) * | 2018-08-15 | 2020-02-25 | 海利尔药业集团股份有限公司 | Method for treating and recycling clothianidin production wastewater |
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| CN110498754B (en) * | 2018-10-19 | 2021-02-23 | 湖北中迅长青科技有限公司 | Preparation method of isothiocyanato compound |
| CN110240555A (en) * | 2019-06-24 | 2019-09-17 | 宁夏贝利特生物科技有限公司 | A kind of synthetic method of 1- isothiocyanic acid base -2- chloro-2-propene |
| CN111808005A (en) * | 2020-07-23 | 2020-10-23 | 岳阳景嘉化工有限公司 | Continuous synthesis method of 2-chloro-3-isothiocyanic acid-1-propylene |
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| CN106278969B (en) | 2018-09-04 |
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