CN1296362C - Process for preparing dimethomoph - Google Patents
Process for preparing dimethomoph Download PDFInfo
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- CN1296362C CN1296362C CNB2003101127266A CN200310112726A CN1296362C CN 1296362 C CN1296362 C CN 1296362C CN B2003101127266 A CNB2003101127266 A CN B2003101127266A CN 200310112726 A CN200310112726 A CN 200310112726A CN 1296362 C CN1296362 C CN 1296362C
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- dimethomorph
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- morpholine
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- 238000004519 manufacturing process Methods 0.000 title description 6
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims abstract description 23
- 239000005761 Dimethomorph Substances 0.000 claims abstract description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000009413 insulation Methods 0.000 claims abstract description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 10
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 8
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000006227 byproduct Substances 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- GMLREHXYJDLZOU-LEPYJNQMSA-N 3-Acetylmorphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GMLREHXYJDLZOU-LEPYJNQMSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 239000002699 waste material Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 239000008096 xylene Substances 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 239000012965 benzophenone Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- -1 Morpholine Diacetyl oxide Dimethylbenzene Acetyl morphine Chemical compound 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- QNBTYORWCCMPQP-NBVRZTHBSA-N (E)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C\C(=O)N1CCOCC1 QNBTYORWCCMPQP-NBVRZTHBSA-N 0.000 description 1
- 241000894006 Bacteria Species 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
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- AWXXNBQGZBENFO-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1.C1COCCN1 AWXXNBQGZBENFO-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method for preparing dimethomoph, which comprises the following steps that in preparing acetyl morpholine, xylene and acetic anhydride are stirred at normal temperature, morpholine is dropped; after the drop is finished, the temperature is slowly enhanced to 110 DEG C for 5 hours of back flow and thermal insulation; after the back flow and the heat preservation are finished, the byproduct of acetic acid is obtained by the exsolution of a still kettle; a residual part in the kettle is the intermediate body of acetyl morpholine; the content is 99%, and the yield is not smaller than 90.2%. In preparing dimethomorph, xylene, E-phenyl ketone and sodium amide are added in a reaction kettle; acetyl morpholine is dropped when the materials are stirred and the temperature is enhanced to 100 DEG C; after the drop is finished and the temperature is enhanced to 110 DEG C, the thermal insulation is 2 hours after the back flow is finished; after the thermal insulation is finished and the temperature is reduced to 80 DEG C, spent lye is separated by a wash kettle; xylene is recovered by the still kettle after the spent lye is washed to neutrality; the dimethomorph is obtained by centrifugal drying; the content is not smaller than 95%, and the yield is not smaller than 76.6%. Because the present invention adopts sodium amide to replace sodium tert-butoxide of the traditional technology, the reaction speed is largely enhanced. The original more than ten hours are shortened to 2 hours, and the productive efficiency is largely enhanced.
Description
Technical field
The present invention relates to a kind of pesticide production technology, be specifically related to a kind of preparation method of dimethomorph.
Background technology
Dimethomorph is comparatively ideal high-efficiency broad spectrum morpholine series bactericidal agent, and to the Oomycete on grape, potato and the tomato, especially Peronosporaceae and phytophthora bacterium have higher sterilizing power, are used to prevent and treat the hemorrhagic disease with purpura mildew and the late blight of potato etc.Characteristics such as it is few to have consumption, and the lasting period is long, and is safe in utilization, good market prospects.
The molecular formula of this compound: C
21H
22ClNO
4
English common name: dimethomorph;
CAS accession number: 110488-70-5;
Chemical name: (E, Z) 4-[3-(4-chloro-phenyl-)-3-(3, the 4-Dimethoxyphenyl) acryloyl] morpholine; (E, Z) 4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl) acryloyl] morpholine;
Other Chinese: peace gram;
Structural formula:
Physico-chemical property:
This product is a clear crystal, 127～148 ℃ of fusing points, (Z)-169.2～170.2 ℃ on isomer, (E)-and 135.7～137.5 ℃ on isomer, vapour pressure 24nPa (20 ℃).Solvability (20～23 ℃): water 50mg/L, acetone 15g (Z)/L, 88g (E)/L, pimelinketone 27g (Z)/L, methylene dichloride 315 (Z) g/L, dimethyl formamide 40g (Z)/L, 272 (E)/L, hexane 0.04g (E)/L, methyl alcohol, toluene 7g (Z)/L.Stability: more than the in the dark stable 5d, daylight [only (Z) has sterilizing ability] (E)-isomer and (Z)-isomer change; Hydrolysis is very slow.881034369.X, Chinese patent application files such as 89103376.9 disclose the synthetic method of series compounds such as dimethomorph.These class methods are to react in the presence of alkali with acetyl morphine employing 3,4-dimethoxy-(being called for short the E-benzophenone), and alkali wherein adopts tertiary alcohol sodium.In the reaction times that these class methods are required 8～12 hours, relatively waste time and energy.
Summary of the invention
The object of the invention is the synthetic method of conventional art is improved, and improves its speed of response, to enhance productivity.It is simultaneously, domestic that what generally adopt at present is that the synthesis technique of starting raw material can pollute surrounding enviroment with the pyrocatechol; The method that the application provides can overcome this pollution, and changes into the E-benzophenone as starting raw material, and the preparation method of production dimethomorph (or its water dispersible granules) pollutes to reduce, and promotes the quality of product.
The method steps of finishing the foregoing invention purpose is as follows:
Diacetyl oxide and 1,4 one morpholine (morpholine) synthesis of acetyl morpholine;
Acetyl morphine and 3, the 4-dimethoxy-4 ' '-chloro-benzophenone (being called for short the E-benzophenone) synthetic dimethomorph in the presence of sodium amide.
More than Fan Ying chemical equation is as follows:
In above-described the production method more specifically step be:
The preparation of acetyl morphine:
To drip and finish slowly to be warmed up to 110 ℃ through the dimethylbenzene and the diacetyl oxide agitation and dropping morpholine at normal temperatures of metering, insulation 5 hours refluxes, finish the back and cross still kettle precipitation and by-product acetic acid, lingering section is the intermediate acetyl morphine, content 99%, yield 〉=90.2% in the still.
The preparation of dimethomorph:
In reactor, drop into dimethylbenzene, E-benzophenone and sodium amide, when being warming up to 100 ℃, stirring drips acetyl morphine, dropwise and be warming up to 110 ℃, back insulation 2 hours refluxes, cross after insulation finishes to be cooled to 80 ℃ and go into to wash still and tell waste lye, be washed to neutral back then and cross still kettle and reclaim dimethylbenzene, get dimethomorph through centrifugal drying, content 〉=95%, yield 〉=76.6%.
Because adopt sodium amide to substitute the sodium tert-butoxide in the conventional art, this programme has improved speed of response significantly, the reaction times with needing more than ten hour originally, shorten to 2 hours, improved production efficiency significantly.Though sodium amide has wherein resolved into ammonia and sodium hydroxide after reaction, in fact sodium amide has played the effect of catalyzer in reaction; Can think that this catalyzer finishes the result that water decomposition is met in the back in reaction, its concrete reaction mechanism is still needed and will further be studied.
This process using be to be starting raw material with the E-benzophenone, greatly reduce influence to surrounding enviroment, by control, make dimethomorph synthetic yield reach 76.6% simultaneously to middle production process, be up to 80%.
Description of drawings
Fig. 1 is the dimethomorph technological process block-diagram.
Embodiment
Embodiment 1, with reference to Fig. 1:
The preparation of acetyl morphine:
In enamel reaction still, drop into dimethylbenzene and diacetyl oxide through metering, open the water coolant stirring and drip the morpholine of suction header tank in advance at normal temperatures, drip and finish slowly to be warmed up to 110 ℃, the insulation that refluxes finished the back in 5 hours and crosses still kettle precipitation and by-product acetic acid, lingering section is the intermediate acetyl morphine in the still, content 99%, yield 〉=90.2%
The synthetic summary sheet of acetyl morphine
| Lot number | Drop into | Output | Yield | ||||||
| Morpholine | Diacetyl oxide | Dimethylbenzene | Acetyl morphine | ||||||
| kg | ％ | kg | ％ | kg | ％ | kg | ％ | ％ | |
| 0101 | 100 | 99 | 129 | 99 | 200 | Grade oil | 135 | 99 | 91 |
| 0102 | 100 | 99 | 129 | 99 | 200 | Grade oil | 132 | 99 | 89.5 |
| 0103 | 100 | 99 | 129 | 99 | 200 | Grade oil | 134 | 99 | 90.5 |
| 0104 | 100 | 99 | 129 | 99 | 200 | Grade oil | 136 | 99 | 91.5 |
| 0105 | 100 | 99 | 129 | 99 | 200 | Grade oil | 134 | 99 | 90.5 |
| 0106 | 100 | 99 | 129 | 99 | 200 | Grade oil | 132 | 99 | 89.0 |
| 0107 | 100 | 99 | 129 | 99 | 200 | Grade oil | 133.5 | 99 | 90.1 |
| 0108 | 100 | 99 | 129 | 99 | 200 | Grade oil | 135 | 99 | 91 |
| Add up to | 800 | 1032 | 160 | 1071.5 | |||||
| Average content | 99％ | ||||||||
| Average yield | 90.4％ | ||||||||
The preparation of dimethomorph:
In reactor, drop into dimethylbenzene, E-benzophenone and sodium amide, stirring drips the acetyl morphine of suction header tank in advance when being warming up to 100 ℃, dropwise and be warming up to the back insulation 2 hours that refluxes, going into to wash still excessively after insulation finishes to be cooled to 80 ℃ divides waste lye to water treatment station, be washed to neutral back then and cross still kettle recovery dimethylbenzene, get dimethomorph through centrifugal drying, content 〉=95%, yield 〉=76.6%.
The synthetic summary sheet of dimethomorph
| Lot number | Drop into | Output | Yield | ||||||||
| The E benzophenone | Acetyl morphine | Sodium amide | Dimethylbenzene | Dimethomorph | |||||||
| kg | ％ | kg | ％ | kg | ％ | kg | ％ | kg | ％ | ％ | |
| 0101 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 86.5 | 97.8 | 77.0 |
| 0102 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 87.6 | 98.2 | 78.3 |
| 0103 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 85.8 | 98.0 | 76.5 |
| 0104 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 87.7 | 97.5 | 77.8 |
| 0105 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 88.4 | 97.2 | 78.2 |
| 0106 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 87.6 | 98.5 | 78.5 |
| 0107 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 85.4 | 98.2 | 76.3 |
| 0108 | 80 | 98 | 51.2 | 99 | 10 | 98 | 300 | Grade oil | 87.9 | 97.4 | 77.9 |
| Add up to | 640 | 410 | 80 | 240 | 681.5 | 100 | |||||
| Average content | 97.85％ | ||||||||||
| Average yield | 76.6％ | ||||||||||
The major equipment table look-up
| Device name | Specification | Quantity |
| Enamel reaction still | 1000L | 2 |
| Enamel reaction still | 2000L | 3 |
| Vacuum pump | Flush-type | 3 |
| Whizzer | 1000 | 1 |
| Gas chromatograph | 6800A | 1 |
| Liquid is thought chromatographic instrument | 1 | |
| Boiler | 2 tons | 1 |
| Stainless Steel Condenser | 6m 2 | 5 |
| Glass condenser | 1.5m 2 | 4 |
| Vacuum drier | 1500L | 1 |
| Pottery four-hole altar | 300-1000 | 0.08 |
The invention is not restricted to these disclosed embodiments, the present invention will cover the scope described in the patent claims, and the various modification of claim scope and equivalence variation.
Claims (2)
1, a kind of preparation method of dimethomorph, step is as follows:
Diacetyl oxide and 1,4 one oxaza hexane synthesis of acetyl morpholine;
Acetyl morphine and 3, the 4-dimethoxy-4 ' '-chloro-benzophenone synthetic dimethomorph in the presence of sodium amide.
According to the preparation method of the described dimethomorph of claim 1, it is characterized in that 2, step is more specifically:
The preparation of acetyl morphine:
To drip and finish slowly to be warmed up to 110 ℃ through the dimethylbenzene and the diacetyl oxide agitation and dropping morpholine at normal temperatures of metering, insulation 5 hours refluxes, finish the back and cross still kettle precipitation and by-product acetic acid, lingering section is the intermediate acetyl morphine, content 99%, yield 〉=90.2% in the still;
The preparation of dimethomorph:
In reactor, drop into dimethylbenzene, 3, the 4-dimethoxy-4 ' '-chloro-benzophenone and sodium amide, when being warming up to 100 ℃, stirring drips acetyl morphine, dropwise and be warming up to after 110 ℃ of backflows insulation 2 hours, cross after insulation finishes to be cooled to 80 ℃ and go into to wash still and tell waste lye, be washed to neutral back then and cross still kettle and reclaim dimethylbenzene, get dimethomorph through centrifugal drying, content 〉=95%, yield 〉=76.6%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2003101127266A CN1296362C (en) | 2003-12-23 | 2003-12-23 | Process for preparing dimethomoph |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2003101127266A CN1296362C (en) | 2003-12-23 | 2003-12-23 | Process for preparing dimethomoph |
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| CN1631884A CN1631884A (en) | 2005-06-29 |
| CN1296362C true CN1296362C (en) | 2007-01-24 |
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| CNB2003101127266A Expired - Fee Related CN1296362C (en) | 2003-12-23 | 2003-12-23 | Process for preparing dimethomoph |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101647447B (en) * | 2009-07-06 | 2012-07-04 | 东莞市瑞德丰生物科技有限公司 | Sterilizing composition |
| CN108047164B (en) * | 2018-02-01 | 2019-12-31 | 山东瑞博龙化工科技股份有限公司 | Utilization method of recovered morpholine in production process of acryloyl morpholine |
| CN118483344A (en) * | 2022-10-17 | 2024-08-13 | 浙江圣兆药物科技股份有限公司 | Liquid chromatography detection method for trace acetic anhydride in glacial acetic acid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1020727C (en) * | 1987-06-11 | 1993-05-19 | 国际壳牌研究有限公司 | Preparation method of 3- (4-chlorphenyl) -3- (3, 4-dimethoxyphenyl) acrylic acid acyl morpholine |
| CN1025497C (en) * | 1988-05-25 | 1994-07-20 | 国际壳牌研究有限公司 | Improved method for preparing 3- (4-chlorphenyl) -3- (3, 4-dimethoxyphenyl) acryloyl morpholine |
| CN1035553C (en) * | 1992-07-10 | 1997-08-06 | 国际壳牌研究有限公司 | New process for the preparation of 3,3-diaryl acrylic acid amides |
| CN1301697A (en) * | 1999-12-29 | 2001-07-04 | 王现全 | Process for preparing 3,3-diaryl acrylyl morpholine |
-
2003
- 2003-12-23 CN CNB2003101127266A patent/CN1296362C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1020727C (en) * | 1987-06-11 | 1993-05-19 | 国际壳牌研究有限公司 | Preparation method of 3- (4-chlorphenyl) -3- (3, 4-dimethoxyphenyl) acrylic acid acyl morpholine |
| CN1025497C (en) * | 1988-05-25 | 1994-07-20 | 国际壳牌研究有限公司 | Improved method for preparing 3- (4-chlorphenyl) -3- (3, 4-dimethoxyphenyl) acryloyl morpholine |
| CN1035553C (en) * | 1992-07-10 | 1997-08-06 | 国际壳牌研究有限公司 | New process for the preparation of 3,3-diaryl acrylic acid amides |
| CN1301697A (en) * | 1999-12-29 | 2001-07-04 | 王现全 | Process for preparing 3,3-diaryl acrylyl morpholine |
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| CN1631884A (en) | 2005-06-29 |
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