CN104356017B - A kind of method of solvent-free acylated synthesis isopropyl methoxalamine - Google Patents
A kind of method of solvent-free acylated synthesis isopropyl methoxalamine Download PDFInfo
- Publication number
- CN104356017B CN104356017B CN201410673466.8A CN201410673466A CN104356017B CN 104356017 B CN104356017 B CN 104356017B CN 201410673466 A CN201410673466 A CN 201410673466A CN 104356017 B CN104356017 B CN 104356017B
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- CN
- China
- Prior art keywords
- isopropyl methoxalamine
- solvent
- alkali
- amidogen ether
- vacuum dehydration
- 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.)
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003513 alkali Substances 0.000 claims abstract description 14
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000018044 dehydration Effects 0.000 claims abstract description 11
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 5
- 239000001099 ammonium carbonate Substances 0.000 claims description 5
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- JJEJDZONIFQNHG-UHFFFAOYSA-N [C+4].N Chemical compound [C+4].N JJEJDZONIFQNHG-UHFFFAOYSA-N 0.000 claims description 2
- BKVHNXUUAWSELQ-UHFFFAOYSA-N [Cl].ClCC(=O)Cl Chemical compound [Cl].ClCC(=O)Cl BKVHNXUUAWSELQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 3
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
A kind of method that the invention discloses solvent-free acylated synthesis isopropyl methoxalamine, it is characterised in that amidogen ether, alkali, water and chloracetyl chloride react in a kettle. and obtain the thick product of isopropyl methoxalamine, it is not necessary to solvent；The thick product of isopropyl methoxalamine passes through washing in settling tank, then obtains isopropyl methoxalamine product through vacuum dehydration still vacuum dehydration.Wherein, amidogen ether: alkali: the concentration ratio of chloracetyl chloride is 1: 1.1: 1.05, reaction temperature 25 DEG C 45 DEG C.The present invention is by using amidogen ether, alkali, water and chloracetyl chloride, and solvent-free acylated synthesis isopropyl methoxalamine, not only production process is simple, and can reduce cost and reduce pollution.
Description
Technical field
The present invention relates to herbicide field, a kind of solvent-free acylated synthesis isopropyl first
The method of grass amine.
Background technology
The method of traditional synthesis isopropyl methoxalamine commonly uses organic solvent, and subsequent processes is complicated,
Cost is high, it is big to pollute, and is unfavorable for industrial production.
The most how to provide a kind of method producing isopropyl methoxalamine, it is not necessary to use solvent, production process letter
Single, and can to reduce cost and reducing and pollute be those skilled in the art's problems of needing solution badly.
Summary of the invention
In view of this, a kind of method that the invention provides solvent-free acylated synthesis isopropyl methoxalamine, it is not necessary to
Using solvent, not only production process is simple, and can reduce cost and reduce pollution.
For achieving the above object, the present invention provides following technical scheme:
A kind of method of solvent-free acylated synthesis isopropyl methoxalamine, it is characterised in that amidogen ether, alkali, water and
Chloracetyl chloride reacts in a kettle. and obtains the thick product of isopropyl methoxalamine, it is not necessary to solvent；Isopropyl methoxalamine is thick
Product passes through washing in settling tank, then obtains isopropyl methoxalamine product through vacuum dehydration still vacuum dehydration.
Wherein, amidogen ether: alkali: the concentration ratio of chloracetyl chloride is 1: 1.1: 1.05, reaction temperature 25 DEG C-45 DEG C.
Preferably, in the method for above-mentioned a kind of solvent-free acylated synthesis isopropyl methoxalamine, alkali can be carbon
At least one in acid sodium, sodium acid carbonate, potassium carbonate, saleratus, carbon ammonium, ammonium hydrogen carbonate.
The present invention is by using amidogen ether, alkali, water and chloracetyl chloride, solvent-free acylated synthesis isopropyl methoxalamine
Method, not only production process is simple, and can reduce cost and reducing and pollute.
Accompanying drawing explanation
In order to be illustrated more clearly that the embodiment of the present invention or technical scheme of the prior art, below will be to reality
Execute the required accompanying drawing used in example or description of the prior art to be briefly described, it should be apparent that below,
Accompanying drawing in description is only embodiments of the invention, for those of ordinary skill in the art, not
On the premise of paying creative work, it is also possible to obtain other accompanying drawing according to the accompanying drawing provided.
Fig. 1 accompanying drawing is the schematic diagram of isopropyl methoxalamine building-up process in the present invention.
Detailed description of the invention
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out
Clearly and completely describe, it is clear that described embodiment is only a part of embodiment of the present invention, and
It is not all, of embodiment.Based on the embodiment in the present invention, those of ordinary skill in the art are not doing
Go out the every other embodiment obtained under creative work premise, broadly fall into the scope of protection of the invention.
The embodiment of the invention discloses a kind of employing amidogen ether, alkali, water and chloracetyl chloride, solvent-free acylated conjunction
The method becoming isopropyl methoxalamine, not only production process is simple, and can reduce cost and reduce pollution.
Please refer to accompanying drawing 1, for the schematic diagram of isopropyl methoxalamine building-up process in the present invention, specifically include:
Amidogen ether, alkali, water and chloracetyl chloride react in a kettle. and obtain the thick product of isopropyl methoxalamine, it is not necessary to solvent；
The thick product of isopropyl methoxalamine passes through washing in settling tank, then obtains different through vacuum dehydration still vacuum dehydration
Methoxalamine product.Wherein, amidogen ether: alkali: the concentration ratio of chloracetyl chloride is 1: 1.1: 1.05, reaction temperature
Spend 25 DEG C-45 DEG C.
In order to optimize technique scheme further, alkali can be sodium carbonate, sodium acid carbonate, potassium carbonate,
At least one in saleratus, ammonium carbonate, ammonium hydrogen carbonate.
In order to optimize technique scheme further, prepare the following 3 kinds of production methods of example:
One, in 250ml flask, amidogen ether (40g, 0.1894mol) is added, addition sodium carbonate (11.2g,
0.1042mol), add water 11.1g, stirring, dropping chloracetyl chloride (22.7g, 0.1988mol), drip
Adding complete continuation to stir 10 minutes, chemical examination obtains conversion ratio 99.5%, is subsequently adding the washing of 30g water, quiet
Putting and point fall upper water, lower organic layer vacuum dehydration, obtain isopropyl methoxalamine 54g, productivity is 98.5%,
G/C content 98%.
Two, in 250ml flask, amidogen ether (40g, 0.1894mol) is added, addition sodium acid carbonate (17.7g,
0.2083mol), add water 11.1g, stirring, dropping chloracetyl chloride (22.7g, 0.1988mol), drip
Add complete continuation to stir 10 minutes, chemically examine conversion ratio 99.5%, be subsequently adding the washing of 30g water, standing point
Fall upper water, lower organic layer vacuum dehydration, obtain isopropyl methoxalamine 54g, productivity 98%, G/C content
98%.
Three, in 250ml flask, amidogen ether (40g, 0.1894mol) is added, addition ammonium carbonate (10g,
0.1041mol), add water 11.1g, stirring, dropping chloracetyl chloride (22.7g, 0.1988mol), drip
Add complete continuation to stir 10 minutes, chemically examine conversion ratio 99.5%, be subsequently adding the washing of 30g water, standing point
Falling upper water, lower organic layer vacuum dehydration, obtain isopropyl methoxalamine 52.7g, productivity 95%, GC contains
Amount 97%
In this specification, each embodiment uses the mode gone forward one by one to describe, and each embodiment stresses
Being the difference with other embodiments, between each embodiment, identical similar portion sees mutually.
For device disclosed in embodiment, owing to it corresponds to the method disclosed in Example, so describing
Fairly simple, relevant part sees method part and illustrates.
Described above to the disclosed embodiments, makes professional and technical personnel in the field be capable of or uses
The present invention.Multiple amendment to these embodiments will be aobvious and easy for those skilled in the art
See, generic principles defined herein can without departing from the spirit or scope of the present invention,
Realize in other embodiments.Therefore, the present invention is not intended to be limited to the embodiments shown herein,
And it is to fit to the widest scope consistent with principles disclosed herein and features of novelty.
Claims (2)
1. the method for a solvent-free acylated synthesis isopropyl methoxalamine, it is characterised in that amidogen ether, alkali, water and chlorine
Chloroacetic chloride reacts in a kettle. and obtains the thick product of isopropyl methoxalamine, it is not necessary to solvent；Isopropyl methoxalamine slightly produces
Product pass through washing in settling tank, then obtain isopropyl methoxalamine product through vacuum dehydration still vacuum dehydration.
Wherein, amidogen ether: alkali: the concentration ratio of chloracetyl chloride is 1: 1.1: 1.05, reaction temperature 25 DEG C-45 DEG C.
The method of a kind of solvent-free acylated synthesis isopropyl methoxalamine the most according to claim 1, its feature exists
In, alkali can be in sodium carbonate, sodium acid carbonate, potassium carbonate, saleratus, carbon ammonium, ammonium hydrogen carbonate
At least one.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410673466.8A CN104356017B (en) | 2014-11-21 | 2014-11-21 | A kind of method of solvent-free acylated synthesis isopropyl methoxalamine |
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| CN201410673466.8A CN104356017B (en) | 2014-11-21 | 2014-11-21 | A kind of method of solvent-free acylated synthesis isopropyl methoxalamine |
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| CN104356017A CN104356017A (en) | 2015-02-18 |
| CN104356017B true CN104356017B (en) | 2016-08-24 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4317916A (en) * | 1979-04-16 | 1982-03-02 | Ciba-Geigy Corporation | Process for producing N-substituted-N-acetyl-2,6-dialkyl-anilines |
| CN102887832A (en) * | 2012-09-29 | 2013-01-23 | 西安近代化学研究所 | Method for synthesizing chloroacetamide compound with large steric hindrance by water phase reaction |
-
2014
- 2014-11-21 CN CN201410673466.8A patent/CN104356017B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4317916A (en) * | 1979-04-16 | 1982-03-02 | Ciba-Geigy Corporation | Process for producing N-substituted-N-acetyl-2,6-dialkyl-anilines |
| CN102887832A (en) * | 2012-09-29 | 2013-01-23 | 西安近代化学研究所 | Method for synthesizing chloroacetamide compound with large steric hindrance by water phase reaction |
Non-Patent Citations (1)
| Title |
|---|
| 精异丙草胺的合成研究;张海滨;《农药科学与管理》;20111231;第32卷(第1期);26-29 * |
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Effective date of registration: 20180103 Address after: 256600 Shandong province Binzhou City foreshore City Qin Yong Xin Road south southeast of Taiwan Patentee after: Shandong Qiao Chang Modern Agriculture Co., Ltd. Address before: 256600 new Yongxin Road south side of Binzhou City, Shandong Province Patentee before: Qiaochang Chemical Co., Ltd., Shandong |
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