CN1204646A - New alpha-phenoxy-alkanols, their methods of preparation and their applications - Google Patents
New alpha-phenoxy-alkanols, their methods of preparation and their applications Download PDFInfo
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- CN1204646A CN1204646A CN 98103149 CN98103149A CN1204646A CN 1204646 A CN1204646 A CN 1204646A CN 98103149 CN98103149 CN 98103149 CN 98103149 A CN98103149 A CN 98103149A CN 1204646 A CN1204646 A CN 1204646A
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- phenoxy
- alkanols
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- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000005591 Pendimethalin Substances 0.000 claims description 11
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 claims description 2
- OIFLWVQOCMMZHG-UHFFFAOYSA-N 3-ethyl-3-(3-ethylpentan-3-yloxy)pentane Chemical group CCC(CC)(CC)OC(CC)(CC)CC OIFLWVQOCMMZHG-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 238000005576 amination reaction Methods 0.000 description 4
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- -1 3,4-dimethyl-phenoxy Chemical group 0.000 description 1
- FERLPLQHWHHCFN-UHFFFAOYSA-N C1(=CC(=C(C=C1)C)C)O.[N+](=O)([O-])C1=CC(=CC=C1)[N+](=O)[O-] Chemical compound C1(=CC(=C(C=C1)C)C)O.[N+](=O)([O-])C1=CC(=CC=C1)[N+](=O)[O-] FERLPLQHWHHCFN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
New alpha -phenoxy-alkanols represented by the general formula (I) in which R1 and R2, which may be identical or different, represent a hydrogen atom or the CH3 radical, and their stereoisomers of R,S conformation when they contain at least one asymmetric carbon.
Description
The present invention relates to new alpha-phenoxy-alkanols.
The present invention also relates to prepare the method for these new alpha-phenoxy-alkanols and they application as synthetic intermediate, in particular for preparation pendimethalin, this is a kind ofly to belong to 2, the selective herbicide of 6-dinitroaniline.
This new alpha-phenoxy-alkanols of the present invention, when they contain at least one unsymmetrical carbon, their R, S conformation stereoisomerism body and function general formula
Expression, wherein, R
1And R
2Can be identical or different, expression hydrogen atom or CH
3Group.
According to the alpha-phenoxy-alkanols method that is used to prepare formula I of the present invention, it is characterized in that 2,6-dinitrobenzene-3, the 4-xylenol be selected from ethylene oxide, propylene oxide and 2, the rudimentary ethylene oxide reaction of 3-butylene oxide ring.
2,6-dinitrobenzene-3,4-xylenol can adopt any known nitrated technology by Industrial products 3, the preparation of 4-xylenol.
Pendimethalin can be by 3 of formula I, and 4-dimethyl phenoxy-alkanol goes out to send preparation, and the compound of formula I can obtain as mentioned above.
For this reason,
-or make 2, and 6-dinitrobenzene-3,4-dimethyl-phenoxy group-alkanol carries out amination reaction, particularly carries out amination reaction with 3-aminopentane auxiliary agent,
-or making 3,4-dimethyl-phenoxy group-alkanol carries out the nitrification derivative that nitration reaction amination subsequently forms like this, particularly carries out amination reaction with 3-aminopentane auxiliary agent.
By the following explanation of doing in addition and easily the indefiniteness example of embodiment will understand the present invention better.
The alpha-phenoxy-alkanols of formula 1 is by means of 2,6-dinitrobenzene-3, the prepared in reaction of the rudimentary oxyethane of addition on the 4-xylenol.
This addition reaction can be carried out in inert organic solvents.
This inert solvent is from selecting to good the group down: aliphatic alkanes, especially hexane, heptane, octane, nonane and dodecane, chlorinated derivatives; Especially methylene dichloride, 1,2-ethylene dichloride, chloroform, trieline and zellon; Dialkyl ether, especially diethyl-and dipropyl-ether and dibutyl ether; Preferred aromatic solvent, especially benzene, toluene and dimethylbenzene.
During reaction the quantity of solvent of Shi Yonging is not a key point.
This addition reaction is carried out not existing under the solvent, can be obtained higher productivity like this.
This addition reaction is carried out in-40～300 ℃ temperature range, and preferred-20～200 ℃, more preferably-10～150 ℃.
This reaction can under atmospheric pressure be carried out or carry out under spontaneous oxyethane pressure.
This reaction is preferably carried out depressing by the oxyethane branch that adds a kind of rare gas element control, especially can carry out under the pressure of argon gas or nitrogen control.
This reaction is preferably carried out under 1～100 atmospheric total pressure, more preferably at 1～25 normal atmosphere, more more preferably total pressure less than 10 normal atmosphere.
3---1
The mol ratio of the employed relatively phenol of employed oxyethane is 1～100, and is preferred 1～20, more preferably 1～5.
The consumption of oxyethane is preferably 1～10mol/mol, more preferably 1～2mol/mol, most preferably 1～1.2mol/mol.
This reaction can not exist or carries out in the presence of catalyzer at catalyzer; Preferably use alkaline catalysts, be selected from uncle's type aliphatic amine and especially be selected from Trimethylamine 99, methyl-diethyl-amine and triethylamine; Uncle's aniline, especially xylidine and Diethyl Aniline; Cyclammonium class, especially pyridine and imidazoles; Also can use alkali, especially soda, potash and lime.
Catalyzer is pressed catalytic amount and is used, and is 10ppm～10000ppm and preferred 50～1000ppm with respect to the consumption of used phenol weight promptly.
These conditions of addition reaction have guaranteed that necessity and time enough are to obtain the phenol conversion greater than 99%; When needs more during high purity, the reaction times can correspondingly prolong and the alpha-phenoxy-alkanols quality that do not cause forming becomes bad.
In an embodiment according to the present invention, the alpha-phenoxy-alkanols that obtains like this has about 99% purity, and is necessary and guaranteed that fully purity is greater than 97% and there is not the preparation of the commercial pendimethalin of nitrosamine; In the preparation of this pendimathlin, can use any known nucleophilic substitution technology.
Like this, easily and synthetic expediently according to alpha-phenoxy-alkanols of the present invention and that represent by formula I phenol derivatives that can sell from market or that obtain easily.
These alpha-phenoxy-alkanols are economically and expediently synthetic important intermediate that contain the selective herbicide of pendimethalin.
The Another application of these alpha-phenoxy-alkanols is based on the following fact: by reacting with ammonia, primary amine or secondary amine, they can be used to prepare important synthesis intermediates-2,6-dinitrobenzene-3,4-xylidine.
α-2,6-dinitrobenzene-3, the preparation of 4-dimethyl-phenoxy group-alkanol and they are used to prepare pendimethalin and can represent with following reaction scheme:
Embodiment 1
The alpha-phenoxy-alkanols of preparation formula I
With 2 of 4g (18.8mmol) 99.9%, 6-dinitrobenzene-3,4-xylenol are packed in the 100ml autoclave, add 1,2 epoxy prapane and 3 alkaline catalystss of 2.21g (38mmol) 99%.Device closed increase nitrogen pressure to 3bar.Elevated temperature to 100 ℃ then; Reaction is monitored with thin layer chromatograph; After 3 hours, the phenol residual quantity is less than 1% and stopped reaction 100 ℃ of insulations.
To room temperature, 5.10g (productive rate 100%) red-brown product is collected in step-down with reactor cooling, and it comprises
-70% 1-(2,6-dinitrobenzene-3,4-dimethyl-phenoxy group)-2-propane and
-30% 2-(2,6-dinitrobenzene-3,4-dimethyl-phenoxy group)-1-propane.
These two kinds of isomer need not separate, because they all are the precursors of pendimethalin.Embodiment 2
A kind of alpha-phenoxy-alkanols with formula I prepares pendimethalin
With 26.0g (97.0mmol) two kind (2 according to embodiment 1 preparation, 6-dinitrobenzene-3,4-dimethyl-phenoxy group)-mixture of propane puts in the three-necked bottle that agitator, thermometer, reflux exchanger and feed hopper are housed, and adds 59.5g (687mmol) 3-aminopentane then in 10 minutes.
Under refluxing, reacted 14 hours at 90 ℃; Reaction process is monitored with thin layer chromatograph; Stopped reaction after ether disappears.
Unreacted excess of ammonia base-3-pentane is under atmospheric pressure distilled, under atmospheric pressure pass through, carry out the aminating reaction operation once more in case recovery back amino-3-pentane can circulate at 90 ℃.
Add 100ml dimethylbenzene then, after with 50ml hydro-thermal washing secondary, under reduced pressure distill dimethylbenzene.
After these dimethylbenzene evaporate fully, collect the pendimethalin of 26.4g (being productive rate 95%) purity 97%.Embodiment 3
A kind of alpha-phenoxy-alkanols with formula I prepares pendimethalin
With 25.0g (92.5mmol) two kind (2 according to embodiment 1 preparation, 6-dinitrobenzene-3,4-dimethyl-phenoxy group)-mixture of propane puts in the stainless steel autoclave that is equiped with agitator and thermometer, adds 40.3g (462mmol) 3-aminopentane at 90 ℃ in 30 minutes then.
Under refluxing under 2 normal atmosphere,, 100 ℃ of reactions 2 hours, reacted 3 hours at 130 ℃ at last then 90 ℃ of reactions 3 hours; Reaction process is monitored with thin layer chromatograph; Stopped reaction after ether disappears.
With the reactor decompression, distillation under atmospheric pressure separates unreacted excess of ammonia base-3-propane then; The latter 90 ℃ by and can in ensuing operation, circulate.
Then 100ml dimethylbenzene is added in the reactor,, under reduced pressure distill dimethylbenzene then with 50ml hydro-thermal washing secondary.
After these dimethylbenzene evaporate fully, collect the pendimethalin of 26.4g (being productive rate 98%) purity 96.4%.
Claims (10)
1, the new alpha-phenoxy-alkanols of representing with logical formula I,
Wherein, R
1And R
2Can be identical or different, expression hydrogen atom or CH
3Group and when they contain at least one unsymmetrical carbon their R, S conformation steric isomer.
2, the method for alpha-phenoxy-alkanols of preparation claim 1 is characterized in that 2,6-dinitrobenzene-3, the 4-xylenol be selected from ethylene oxide, propylene oxide and 2, the rudimentary ethylene oxide reaction of 3-butylene oxide ring.
3, according to the method for claim 2, it is characterized in that reacting is to carry out in-40～300 ℃ temperature range, preferred-20～200 ℃, more preferably-10～150 ℃.
4, according to the method one of in claim 2 and 3, it is characterized in that reaction is to carry out under 1～100 atmospheric total pressure, more preferably at 1～25 normal atmosphere, more more preferably total pressure less than 10 normal atmosphere.
5, according to the method one of in the claim 2～4, it is characterized in that the mol ratio of the employed relatively phenol of employed oxyethane is 1～100, preferred 1～20, more preferably 1～5.
6, according to the method one of in the claim 2～5, it is characterized in that this is reflected at a kind of alkaline catalysts and carries out under existing, alkaline catalysts is selected from uncle's type aliphatic amine and especially is selected from Trimethylamine 99, methyl-diethyl-amine and triethylamine; Uncle's aniline, especially xylidine and Diethyl Aniline; Cyclammonium class, especially pyridine and imidazoles.
7,, it is characterized in that the catalyst consumption ratio is 10ppm～10000ppm and preferred 50～1000ppm according to the method for claim 6.
8,, it is characterized in that reacting and be under the condition that does not have solvent, to carry out according to the method one of in the claim 2～7.
9, according to the method one of in the claim 2～7, it is characterized in that reacting in a kind of inert organic solvents and carry out, this inert solvent is selected from: aliphatic hydrocrbon, especially hexane, heptane, octane, nonane and dodecane; Chlorinated derivatives, especially methylene dichloride, 1,2-ethylene dichloride, chloroform, trieline and zellon; Dialkyl ether, especially diethyl-and dipropyl-ether and dibutyl ether; Preferred aromatic solvent, especially benzene, toluene and dimethylbenzene.
10, according to the application in preparation pendimethalin of the alpha-phenoxy-alkanols of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 98103149 CN1204646A (en) | 1997-07-02 | 1998-07-02 | New alpha-phenoxy-alkanols, their methods of preparation and their applications |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9708361 | 1997-07-02 | ||
| CN 98103149 CN1204646A (en) | 1997-07-02 | 1998-07-02 | New alpha-phenoxy-alkanols, their methods of preparation and their applications |
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| Publication Number | Publication Date |
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| CN1204646A true CN1204646A (en) | 1999-01-13 |
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603558A (en) * | 2011-01-20 | 2012-07-25 | 赣南师范学院 | Surface-active substance taking 4-nitro-2',5-dichloro salicylanilide as matrix and preparation technology of surface-active substance |
-
1998
- 1998-07-02 CN CN 98103149 patent/CN1204646A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603558A (en) * | 2011-01-20 | 2012-07-25 | 赣南师范学院 | Surface-active substance taking 4-nitro-2',5-dichloro salicylanilide as matrix and preparation technology of surface-active substance |
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