CN107474012A - A kind of preparation method of Nylar - Google Patents
A kind of preparation method of Nylar Download PDFInfo
- Publication number
- CN107474012A CN107474012A CN201710789103.4A CN201710789103A CN107474012A CN 107474012 A CN107474012 A CN 107474012A CN 201710789103 A CN201710789103 A CN 201710789103A CN 107474012 A CN107474012 A CN 107474012A
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- CN
- China
- Prior art keywords
- nylar
- preparation
- degree
- chloropyridines
- phenoxy
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- 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.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
Abstract
The present invention relates to a kind of preparation method of Nylar, using 4 phenoxy phenyls as Material synthesis intermediate 1（4 phenoxy-phenoxies）2 propyl alcohol, intermediate without isolation, directly Nylar are synthesized after toluene solvant processing with 2 chloropyridines.The advantage of the invention is that：The route and method are simple, and condition is gentleer, and simplify operating procedure, improve reaction yield, are more beneficial for industrialized production, and synthesis total recovery has reached 85.5%（In terms of POP）, active compound content >=97%.
Description
Technical field
The invention belongs to agrochemicals field, more particularly to a kind of preparation method of Nylar.
Background technology
Nylar is a kind of insect growth regulator, IGR with juvenile hormone activity, is opened from Japan toward friendly KCC
Hair.It is high except having to whitefly in bt cotton, greenhouse whitefly available for the agricultural pests for preventing and treating Homoptera, Thysanoptera, Diptera, Lepidoptera
It is active outer, have to agricultural pests such as scale insect, black peach aphid, prodenia litura, the colorado potato bugs such as pear psyllid, Red Garden a red-spotted lizard good
Prevention effect.
As the whole world is increasingly paid attention to environmental protection, the demand of less toxic, efficient, environment-friendly insecticide increases year by year
Add, high poison, high residue, the pesticide species big to eco-environmental impact will be eliminated, the Nylar substitute outstanding as one
Kind, its research and development has good prospect, it will brings huge Social benefit and economic benefit.
And the synthetic method of existing Nylar, method are all cumbersome, reaction condition is more violent.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of method is simple, the system of the relatively mild insecticide Nylar of condition
Preparation Method.
In order to solve the above technical problems, the technical scheme is that：A kind of preparation method of Nylar, its innovative point exist
In with 4- phenoxy phenyls（Abbreviation POP）For Material synthesis intermediate 1-（4- phenoxy-phenoxies）2- propyl alcohol（Abbreviation PPP）,
Intermediate without isolation, directly synthesizes Nylar, its step is as follows after toluene solvant processing with 2- chloropyridines：
(1) potassium hydroxide and water are put into four-hole boiling flask, 4- phenoxy phenyls is slowly added into after stirring and dissolving, is heated to 60 DEG C
Ice bath cools to 10 degree of dropwise addition expoxy propane afterwards, continues the h of insulation reaction 4 in 10-20 degree, to terminal；
(2) toluene is added, is warming up to 50 degree of branch vibration layers, potassium hydroxide is added, stirring, is heated to 80 degree, 2- chloropyridines are added dropwise,
Continue insulation reaction to terminal, separate oil reservoir, be washed to neutrality, precipitation, residue recrystallizes to obtain white crystal with absolute methanol.
The reaction equation of above-mentioned steps is as follows：
。
Further, the 4- phenoxy phenyls in the step (1) are industrial goods, and expoxy propane is pure for chemistry.
Further, the 2- chloropyridines in the step (2) are industrial goods, and methanol is pure for chemistry, and white crystal is pyrrole third
Ether, 48.0~49.0 DEG C of its fusing point, yield 85.5%, content 97.2%.
Further, the potassium hydroxide in the step (1) or step (2) is industrial goods.
The advantage of the invention is that：It is without isolation, molten in toluene as Material synthesis intermediate PPP, intermediate PPP using POP
Nylar directly is synthesized with 2- chloropyridines after agent processing, the route and method are simple, and condition is gentleer, and simplify operation step
Suddenly, reaction yield is improved, is more beneficial for industrialized production, synthesis total recovery has reached 85.5%（In terms of POP）, active compound content
≥97%。
Embodiment
The following examples can make professional and technical personnel that the present invention be more fully understood, but therefore not send out this
It is bright to be limited among described scope of embodiments.
A kind of preparation method of Nylar, with 4- phenoxy phenyls（Abbreviation POP）For Material synthesis intermediate 1-（4- benzene oxygen
Phenoxyl）2- propyl alcohol（Abbreviation PPP）, intermediate PPP without isolation, toluene solvant processing after directly synthesized with 2- chloropyridines
Nylar, its step are as follows：
（1）32.08 g (0.55 mo1) potassium hydroxide and 300 mL water, stirring and dissolving are put into 1000 mL four-hole boiling flask
After be slowly added into 93 g (0.5 mo1) 4- phenoxy phenyls, after being heated to 60 DEG C ice bath cool to 10 degree dropwise addition 31.9g (0.55
Mo1) expoxy propane, the h of insulation reaction 4 is continued in 10-20 degree, to terminal；
（2）Toluene 400ml is added, is warming up to 50 degree of branch vibration layers, 32.08g (0.55 mo1) potassium hydroxide is added, stirring, adds
62.4 g (0.55mo1) 2- chloropyridines are added dropwise to 80 degree in heat, continue insulation reaction to terminal, separate oil reservoir, be washed to neutrality,
Precipitation, residue recrystallize to obtain white crystal, 48.0~49.0 DEG C of 141.2g fusing points, yield 85.5%, content with absolute methanol
97.2%。
The general principle and principal character and advantages of the present invention of the present invention has been shown and described above.The skill of the industry
For art personnel it should be appreciated that the present invention is not limited to the above embodiments, described in above-described embodiment and specification is explanation
The principle of the present invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these
Changes and improvements all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent thereof.
Claims (4)
- A kind of 1. preparation method of Nylar, it is characterised in that, using 4- phenoxy phenyls as Material synthesis intermediate 1-（4- benzene Epoxide phenoxy group）2- propyl alcohol, intermediate without isolation, directly Nylar are synthesized after toluene solvant processing with 2- chloropyridines, its Step is as follows:(1) potassium hydroxide and water are put into four-hole boiling flask, 4- phenoxy phenyls is slowly added into after stirring and dissolving, is heated to 60 DEG C Ice bath cools to 10 degree of dropwise addition expoxy propane afterwards, continues the h of insulation reaction 4 in 10-20 degree, to terminal；(2) toluene is added, is warming up to 50 degree of branch vibration layers, potassium hydroxide is added, stirring, is heated to 80 degree, 2- chloropyridines are added dropwise, Continue insulation reaction to terminal, separate oil reservoir, be washed to neutrality, precipitation, residue recrystallizes to obtain white crystal with absolute methanol.
- 2. the preparation method of Nylar according to claim 1, it is characterised in that:4- phenoxy groups in the step (1) Phenol is industrial goods, and expoxy propane is pure for chemistry.
- 3. the preparation method of Nylar according to claim 1, it is characterised in that:2- chloropyridines in the step (2) For industrial goods, methanol is pure for chemistry, and white crystal is Nylar, 48.0~49.0 DEG C of its fusing point, yield 85.5%, content 97.2%。
- 4. the preparation method of Nylar according to claim 1, it is characterised in that:In the step (1) or step (2) Potassium hydroxide be industrial goods.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710789103.4A CN107474012A (en) | 2017-09-05 | 2017-09-05 | A kind of preparation method of Nylar |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710789103.4A CN107474012A (en) | 2017-09-05 | 2017-09-05 | A kind of preparation method of Nylar |
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| CN107474012A true CN107474012A (en) | 2017-12-15 |
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| CN201710789103.4A Pending CN107474012A (en) | 2017-09-05 | 2017-09-05 | A kind of preparation method of Nylar |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503471A (en) * | 2018-11-23 | 2019-03-22 | 江苏龙灯化学有限公司 | A kind of crystal form of Nylar and its preparation method and application |
| CN111909081A (en) * | 2019-05-07 | 2020-11-10 | 江苏龙灯化学有限公司 | Method for purifying pyriproxyfen technical, product obtained by method and application of pyriproxyfen technical |
| CN112724075A (en) * | 2020-12-31 | 2021-04-30 | 上海科利生物医药有限公司 | Preparation method of pyriproxyfen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1650709A (en) * | 2005-01-18 | 2005-08-10 | 上海应用技术学院 | Preparation method of pyriproxyfen |
-
2017
- 2017-09-05 CN CN201710789103.4A patent/CN107474012A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1650709A (en) * | 2005-01-18 | 2005-08-10 | 上海应用技术学院 | Preparation method of pyriproxyfen |
Non-Patent Citations (2)
| Title |
|---|
| 何锡辉等: "蚊蝇醚的合成工艺研究", 《西华大学学报·自然科学版》 * |
| 高永红等: "蚊蝇醚的合成方法改进", 《化学世界》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503471A (en) * | 2018-11-23 | 2019-03-22 | 江苏龙灯化学有限公司 | A kind of crystal form of Nylar and its preparation method and application |
| CN109503471B (en) * | 2018-11-23 | 2022-08-26 | 江苏龙灯化学有限公司 | Crystal form of pyriproxyfen, preparation method and application thereof |
| CN111909081A (en) * | 2019-05-07 | 2020-11-10 | 江苏龙灯化学有限公司 | Method for purifying pyriproxyfen technical, product obtained by method and application of pyriproxyfen technical |
| CN111909081B (en) * | 2019-05-07 | 2024-01-09 | 江苏龙灯化学有限公司 | Method for purifying pyriproxyfen technical, product obtained by method and application of pyriproxyfen technical |
| CN112724075A (en) * | 2020-12-31 | 2021-04-30 | 上海科利生物医药有限公司 | Preparation method of pyriproxyfen |
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Application publication date: 20171215 |