CN1046940C - Process for preparing alpha-triazolyl-pinacolone - Google Patents
Process for preparing alpha-triazolyl-pinacolone Download PDFInfo
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- CN1046940C CN1046940C CN96101759A CN96101759A CN1046940C CN 1046940 C CN1046940 C CN 1046940C CN 96101759 A CN96101759 A CN 96101759A CN 96101759 A CN96101759 A CN 96101759A CN 1046940 C CN1046940 C CN 1046940C
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- Prior art keywords
- pinacolone
- oxazolone
- triazole
- alkali
- organic solvent
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- 238000004519 manufacturing process Methods 0.000 title description 9
- 239000003513 alkali Substances 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical class CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 triazole salt Chemical class 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 238000004090 dissolution Methods 0.000 claims 1
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 abstract description 20
- 238000000034 method Methods 0.000 abstract description 18
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 abstract description 13
- 239000002699 waste material Substances 0.000 abstract description 7
- 238000006482 condensation reaction Methods 0.000 abstract description 3
- 239000012043 crude product Substances 0.000 abstract description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002912 waste gas Substances 0.000 abstract 1
- 239000002351 wastewater Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000003852 triazoles Chemical class 0.000 description 10
- 125000001425 triazolyl group Chemical group 0.000 description 8
- MBGXGIRUXKTQIN-UHFFFAOYSA-N CC(C(C)(C)C)=O.[Cl] Chemical compound CC(C(C)(C)C)=O.[Cl] MBGXGIRUXKTQIN-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 5
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000009776 industrial production Methods 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- ULSAJQMHTGKPIY-UHFFFAOYSA-N 1-chloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CCl ULSAJQMHTGKPIY-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 230000000361 pesticidal effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 description 1
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 description 1
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000005985 Paclobutrazol Substances 0.000 description 1
- CNFMJLVJDNGPHR-UKTHLTGXSA-N Triapenthenol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1CCCCC1 CNFMJLVJDNGPHR-UKTHLTGXSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UYXAHRLPUPVSNJ-UHFFFAOYSA-N sodium;2h-triazole Chemical compound [Na].C=1C=NNN=1 UYXAHRLPUPVSNJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention provides a method for preparing alpha-triazolyl-pinacolone. 1, 2, 4-triazazole reacts with alkali with the existence of organic solvent to generate triazole salt; the triazole salt and halogenated pinacolone have a condensation reaction in organic solvent to generate oxazolone. The method enhances the yield of 1H-oxazolone, increases the purity, reduces the cost and reduces the pollution from waste water, waste residue and waste gas. The method is suitable for industrial preparation. The yield of 1H-oxazolone can reach 93.8%, and the purity of crude products can reach 92%.
Description
The present invention relates to the preparation of alpha-triazolyl Pinacolone.
Alpha-triazolyl Pinacolone (abbreviation oxazolone) has two kinds of isomer: 1-(1H-1,2,4-triazol-1-yl)-3,3-dimethyl butyrate-2-ketone (being called for short the 1H-oxazolone) and 1-(4H-1,2,4-triazole-4-yl)-3,3-dimethyl butyrate-2-ketone (being called for short the 4H-oxazolone).In oxazolone preparation, the 1H-oxazolone is a primary product with practical value, and the 4H-oxazolone then is not wish the by product that occurs.The 1H-oxazolone itself has good biological activity, thereby can be used as the sterilant application.Yet the 1H-oxazolone be the more important thing is the important intermediate as organic products, particularly triazole species agricultural chemicals (as paclobutrazol, uniconazole, triapenthenol, the strain azoles that contracts, alkene azoles alcohol, diclobutrazol etc.).The production practice of above-mentioned Pesticidal products prove, the preparation of oxazolone is an important techniques key to the production of whole Pesticidal products, make great efforts to improve the yield and the purity of the 1H-oxazolone in the oxazolone preparation, to the quality that improves Pesticidal products, reduce production costs, reduce three-waste pollution, all have crucial practical significance.
The preparation method of oxazolone sums up following three kinds: (1) Pinacolone, triazole and sulfur oxychloride reaction (Timmler, H.et al., Ger.Offen.2431407,1976); (2) the bromo Pinacolone in the presence of sodium Metal 99.5 or sodium alkoxide with the reaction of triazole (et al., Ger.Offen.DE 3335767,1985 for Elbe, H.L.); (3) the chloro Pinacolone in the presence of acid binding agent such as salt of wormwood with the reaction (Ger.Offen.DE 3144670,1983 for Ekbe, H.L.et al.) of triazole.In above-mentioned three kinds of methods, method (1) is though raw materials used Pinacolone ratio method (2), (3) are simple, because yield is low, and inconvenient operation, practical value is little.Method (2) though yield increase, raw materials used bromo Pinacolone, sodium Metal 99.5 or sodium alkoxide etc., the industrial production cost is too high, operational condition is also harsh, so also seldom be used for industrial production.Method (3) is used a chlorine Pinacolone that cheaply is easy to get and has been replaced the bromo Pinacolone, has replaced sodium Metal 99.5 or sodium alkoxide with the cheaper salt of wormwood of price, so be better than method (1) and (2) on the whole.But still there is more shortcoming in this method: first, under the given condition of this method, chloro Pinacolone and triazole are directly carried out condensation reaction, because the reactive behavior of reactant itself is strong inadequately, so that the yield of product (1H-oxazolone) is all lower, generally have only about 72%, thick product is as purification processes not, and its purity has only 70-80%.The second, adopt salt of wormwood to make acid binding agent, price height, consumption are big, thus the three wastes particularly waste residue (contain KHCO
3, KCl etc.) growing amount also big.Require in addition salt of wormwood strict anhydrous and this to certain fineness (more than 300 orders), otherwise can significantly reduce product yield.The 3rd, used acetone, ethyl acetate etc. are solvent volatile, that the rate of recovery is low, price is higher, and be therefore not only uneconomical but also dangerous on industrial production.The 4th, because above-mentioned shortcoming has caused the raising of oxazolone production cost.
The purpose of this invention is to provide a kind of new improved method for preparing the alpha-triazolyl Pinacolone.The present invention can overcome existing methods shortcoming in the above-mentioned document.The present invention is operational path and the method that adopts the synthetic oxazolone of two-step approach, promptly at first in organic solvent, make triazole and highly basic (as NaOH, KOH etc.) effect, generate triazolium salt (as sodium salt) under the condition of heating, triazolium salt generates oxazolone with the reaction of halo Pinacolone more then.
The present invention is with 1,2, and 4-triazole and alkali (sodium hydroxide or potassium hydroxide) react the generation triazolium salt in the presence of organic solvent, and triazolium salt and halo Pinacolone carry out condensation reaction and generate oxazolone in organic solvent.Used alkali is NaOH preferably, used halo Pinacolone is bromo Pinacolone and chloro Pinacolone, a chlorine Pinacolone preferably, the used molar ratio of above-mentioned reaction is: triazole: a chlorine Pinacolone: alkali=1～1.5: 1: 1～1.5, and wherein optimum molar ratio is 1.05: 1: 1.05.Organic solvent is the lower aliphatic alcohols, as methyl alcohol, ethanol, propyl alcohol etc., and arene, as benzene, chloro benzene,toluene,xylene etc., halogenated alkane is as 1,2-ethylene dichloride, trichloroethane etc., wherein optimum is toluene.
The temperature that the present invention prepares triazole sodium salt is 60-120 ℃, and optimum temperature is 100～111 ℃; Oxazolone synthetic temperature is 25-95 ℃, and optimum temperature is 70-75 ℃.The oxazolone synthetic reaction times is 3～8 hours, and the optimum time is 4～5 hours.
The advantage of this method is: (1) since with the triazolium salt (as sodium salt) of chlorine Pinacolone reaction reactive behavior height more than triazole, institute is so that the reaction of generation oxazolone becomes is more prone to carry out.And the preparation of triazolium salt is very easy to, and almost is to obtain triazolium salt quantitatively.In addition, triazole becomes triazolium salt, makes to generate to pay to produce the minimizing of 4H-oxazolone.Owing to fundamentally improved the activity of oxazolone building-up reactions, and improved the condition that the 1H-oxazolone generates, so improved the yield (high this 93.8%) and the purity (crude product purity reaches 92%) of 1H-oxazolone significantly.(2) because employing is cheap and easy to get, molecular weight is little, the strong alkali (as NaOH) of alkalescence has replaced the Anhydrous potassium carbonate that price is expensive, molecular weight big, alkalescence is weak, so not only improved the activity of oxazolone building-up reactions, and the actual amount of alkali significantly reduces, thereby quantity of three wastes (particularly pay and produce waste residue) also correspondingly significantly reduces.The NaOH that price is low, consumption is few uses, and will inevitably make the reduction of oxazolone production cost.(3) owing to adopt price is low, the rate of recovery is high toluene etc. to make solvent, to replace price height, volatile, acetone that the rate of recovery is low, ethyl acetate etc., not only helping successful reaction carries out, and helps lowering production cost, makes production operation safer.(4) this method is as using K
2CO
3Require the anhydrous and fineness of the strictness of raw material like that, thereby operate simple and easyly, be suitable for industrial production.
Because above-mentioned advantage, the characteristics that the inventive method prepares oxazolone are high product yield and purity to be arranged, low production cost and three-waste pollution.
The present invention has outstanding substantive distinguishing features and beneficial effect can be embodied from following embodiment, but whether the present invention is imposed any restrictions.
Embodiment 1
Adding 21 gram concentration are 20% aqueous sodium hydroxide solution (containing NaOH 0.105mol) in the 250ml reaction flask, 7.63 gram (0.105mol) 1,2, and the 4-triazole stirs, complete molten back adding 100ml toluene.Heat temperature raising, reflux dewatered in four hours to temperature be 111 ℃.Finish postcooling to 60～65 ℃ of dehydration add 14.4 gram (0.10mol) chlorine Pinacolones, and stirring heating heats up, and keeps 70～75 ℃ of reactions 4-5 hour.Reaction is cooled to room temperature after finishing.Carry out suction filtration then, twice (2 * 10ml) of toluene wash of filter cake, merging filtrate, decompression precipitation eliminate solvent, residuum is light yellow or pale brown look oily matter, and very fast crystallization is solidified after the cooling, obtains 17.20 gram oxazolone crude products after drying, through gas Chromatographic Determination, 1H-oxazolone content is 92.25%, and the 4H-oxazolone is 2.03%, and the yield of 1H-oxazolone is 93.89% (in a chlorine Pinacolone).(1H-oxazolone and 4H-oxazolone are purified after fusing point test, ultimate analysis and
1H NMR gives structure authentication).
Embodiment 2～12
Adopt different reaction feed ratio and different alkali and solvents, all the other operational conditions are identical with embodiment 1, and experimental result sees Table 1.Table 1 is oxazolone content and the yield that obtains under different feed ratio, alkali and the solvent spare part.
Table 1
| Embodiment | Mole number feeds intake | Solvent | Oxazolone | ||||
| One chlorine Pinacolone (content: 98.67%) | Triazole content: 〉=95% | NaOH(a) KOH(b) | Content (%) | Yield (%) 1H-body | |||
| The 1H-body | The 4H-body | ||||||
| 2 | 0.10 | 0.105 | 0.105(b) | Toluene | 92.14 | 2.11 | 93.41 |
| 3 | 0.10 | 0.10 | 0.10(a) | Toluene | 93.01 | 1.89 | 92.78 |
| 4 | 0.10 | 0.105 | 0.10(a) | Toluene | 92.55 | 2.13 | 93.01 |
| 5 | 0.10 | 0.105 | 0.105(a) | Benzene | 88.01 | 2.29 | 87.31 |
| 6 | 0.10 | 0.105 | 0.105(b) | Benzene | 88.94 | 1.78 | 86.88 |
| 7 | 0.10 | 0.105 | 0.10(a) | Benzene | 87.35 | 2.44 | 86.49 |
| 8 | 0.10 | 0.10 | 0.10(a) | Benzene | 88.02 | 2.51 | 86.31 |
| 9 | 0.10 | 0.10 | 0.11(a) | Toluene | 89.04 | 2.23 | 89.12 |
| 10 | 0.10 | 0.105 | 0.105(a) | Dimethylbenzene | 90.10 | 2.47 | 91.33 |
| 11 | 0.10 | 0.105 | 0.105(a) | Methyl alcohol | 84.01 | 2.44 | 84.24 |
| 12 | 0.10 | 0.105 | 0.105(a) | Ethanol | 86.38 | 2.17 | 95.86 |
Claims (4)
1. the preparation method of an alpha-triazolyl Pinacolone is characterized in that it is through following step:
(1) with 1,2,4-triazole and alkali mixed dissolution heat in organic solvent, and 60～120 ℃ were refluxed 2～6 hours, finish postcooling to 60～65 ℃ of dehydration;
(2) add a halogen Pinacolone, reacted 4～5 hours down at 70～75 ℃;
(3) be cooled to room temperature, filter, filtrate decompression is sloughed the crystallization of solvent postcooling, dries, and is product;
The material mole proportioning of described reaction is: 1,2, and 4-triazole: a halogen Pinacolone: alkali=1～1.5: 1: 1～1.5; Described organic solvent can be lower aliphatic alcohols, arene or halogenated alkane.
2. according to the described preparation method of claim 1, it is characterized in that described material mole proportioning is: 1,2,4-triazole: a halogen Pinacolone: alkali=1.05: 1: 1.05.
3. according to the described preparation method of claim 1, it is characterized in that described organic solvent is a toluene.
4. according to the described preparation method of claim 1, it is characterized in that described alkali is sodium hydroxide or potassium hydroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96101759A CN1046940C (en) | 1996-02-14 | 1996-02-14 | Process for preparing alpha-triazolyl-pinacolone |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96101759A CN1046940C (en) | 1996-02-14 | 1996-02-14 | Process for preparing alpha-triazolyl-pinacolone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1137038A CN1137038A (en) | 1996-12-04 |
| CN1046940C true CN1046940C (en) | 1999-12-01 |
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| CN96101759A Expired - Fee Related CN1046940C (en) | 1996-02-14 | 1996-02-14 | Process for preparing alpha-triazolyl-pinacolone |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105037282A (en) * | 2015-05-25 | 2015-11-11 | 张家港市振方化工有限公司 | Triazolyl pinacolone purification method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4642385A (en) * | 1985-11-19 | 1987-02-10 | Mobay Corporation | Preparation of monochloropinacolone |
| US4970320A (en) * | 1990-01-24 | 1990-11-13 | Mobay Corporation | Preparation of phenoxy-triazolyl-pinacol-ones |
-
1996
- 1996-02-14 CN CN96101759A patent/CN1046940C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4642385A (en) * | 1985-11-19 | 1987-02-10 | Mobay Corporation | Preparation of monochloropinacolone |
| US4970320A (en) * | 1990-01-24 | 1990-11-13 | Mobay Corporation | Preparation of phenoxy-triazolyl-pinacol-ones |
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| Publication number | Publication date |
|---|---|
| CN1137038A (en) | 1996-12-04 |
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