HU194538B - Continuous process for production of 1-/methil-thio/-acetaldoxim-n-methil-carbamate /methomil/ - Google Patents
Continuous process for production of 1-/methil-thio/-acetaldoxim-n-methil-carbamate /methomil/ Download PDFInfo
- Publication number
- HU194538B HU194538B HU841262A HU126284A HU194538B HU 194538 B HU194538 B HU 194538B HU 841262 A HU841262 A HU 841262A HU 126284 A HU126284 A HU 126284A HU 194538 B HU194538 B HU 194538B
- Authority
- HU
- Hungary
- Prior art keywords
- reactor
- methyl isocyanate
- temperature
- reaction
- methyl
- Prior art date
Links
- 238000010924 continuous production Methods 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 239000005916 Methomyl Substances 0.000 abstract description 12
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 abstract description 12
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- AGVHWUQIIQHFCW-DUXPYHPUSA-N (ne)-n-(2-methylsulfanylethylidene)hydroxylamine Chemical compound CSC\C=N\O AGVHWUQIIQHFCW-DUXPYHPUSA-N 0.000 abstract description 2
- 239000012948 isocyanate Substances 0.000 abstract description 2
- 150000002513 isocyanates Chemical class 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract 1
- 238000010923 batch production Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 9
- -1 dialkylcarbamoyl chloride Chemical compound 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- TYEVWCPZVQACAE-ARJAWSKDSA-N methyl (1z)-n-hydroxyethanimidothioate Chemical compound CS\C(C)=N/O TYEVWCPZVQACAE-ARJAWSKDSA-N 0.000 description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- KGGVGTQEGGOZRN-SNAWJCMRSA-N (ne)-n-butylidenehydroxylamine Chemical compound CCC\C=N\O KGGVGTQEGGOZRN-SNAWJCMRSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZXWNFKKVGPYFRR-UHFFFAOYSA-N 3-ethenyl-2-methylpyridine Chemical compound CC1=NC=CC=C1C=C ZXWNFKKVGPYFRR-UHFFFAOYSA-N 0.000 description 1
- 239000010963 304 stainless steel Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/243—Tubular reactors spirally, concentrically or zigzag wound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48049783A | 1983-03-30 | 1983-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU194538B true HU194538B (en) | 1988-02-29 |
Family
ID=23908189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU841262A HU194538B (en) | 1983-03-30 | 1984-03-29 | Continuous process for production of 1-/methil-thio/-acetaldoxim-n-methil-carbamate /methomil/ |
Country Status (8)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924354A (zh) * | 2012-10-23 | 2013-02-13 | 海利贵溪化工农药有限公司 | 一种灭多威的合成方法 |
| JP6086250B2 (ja) * | 2014-04-25 | 2017-03-01 | 大陽日酸株式会社 | 気液反応方法及びアミノシランの製造方法 |
| CN111377843B (zh) * | 2020-04-02 | 2022-03-18 | 湖南海利常德农药化工有限公司 | 一种灭多威的制备方法 |
| CN111450791B (zh) * | 2020-05-08 | 2023-04-18 | 河南金鹏化工有限公司 | 一种异氰酸甲酯生产灭多威的连续化工艺及装置 |
| CN112125829A (zh) * | 2020-09-28 | 2020-12-25 | 山东华阳农药化工集团有限公司 | 降低杂质1，3-二甲基脲含量的高纯度灭多威生产方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459866A (en) * | 1967-08-31 | 1969-08-05 | James B Buchanan | Hydroxamate carbamates as nematocides |
-
1984
- 1984-03-14 CA CA000449567A patent/CA1216304A/en not_active Expired
- 1984-03-29 EP EP84302169A patent/EP0121420B1/en not_active Expired
- 1984-03-29 AT AT84302169T patent/ATE24175T1/de active
- 1984-03-29 JP JP59059657A patent/JPS59184154A/ja active Granted
- 1984-03-29 IL IL71400A patent/IL71400A/xx not_active IP Right Cessation
- 1984-03-29 DE DE8484302169T patent/DE3461636D1/de not_active Expired
- 1984-03-29 ZA ZA842364A patent/ZA842364B/xx unknown
- 1984-03-29 HU HU841262A patent/HU194538B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0121420A1 (en) | 1984-10-10 |
| DE3461636D1 (en) | 1987-01-22 |
| ZA842364B (en) | 1984-11-28 |
| IL71400A0 (en) | 1984-06-29 |
| IL71400A (en) | 1987-10-30 |
| JPS59184154A (ja) | 1984-10-19 |
| JPS6230985B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-07-06 |
| ATE24175T1 (de) | 1986-12-15 |
| CA1216304A (en) | 1987-01-06 |
| EP0121420B1 (en) | 1986-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7230130B2 (en) | Process for preparing methylenedianiline and methylenebis (phenylisocyanate) | |
| EP0126300B1 (de) | Mehrstufenverfahren zur Herstellung von 3-Isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat | |
| EP0126299B1 (de) | Mehrstufenverfahren zur Herstellung von Hexamethylen-diisocyanat-1,6 und/oder isomeren aliphatischen Diisocyanaten mit 6 Kohlenstoffatomen im Alkylenrest | |
| US20050038282A1 (en) | Process for producing alkyl nitrite | |
| EP3546468B1 (de) | Verfahren zur herstellung alkoxysilangruppen-haltiger isocyanate | |
| LU83896A1 (fr) | Procede de preparation d'urethanes aromatiques | |
| US2480088A (en) | Process of producing carbamyl chlorides | |
| HU194538B (en) | Continuous process for production of 1-/methil-thio/-acetaldoxim-n-methil-carbamate /methomil/ | |
| US5523452A (en) | Process for preparing dimethyl carbonate | |
| JPH0432807B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4178448A (en) | Process for preparing herbicidal triazines | |
| US3957868A (en) | Process for preparing urea from ammonia and carbon dioxide | |
| KR100785431B1 (ko) | 멜라민 제조 방법 | |
| DE69423910T2 (de) | Verfahren zur herstellung von difluormethan und 1,1,1,2-tetrafluorethan | |
| JPH06298701A (ja) | 蟻酸メチルの製法 | |
| US4647661A (en) | Method of preparing ω-lactams, in particular caprolactam | |
| JPH06122667A (ja) | ３−シアノ−３，５，５−トリメチルシクロヘキサノンの連続的製造方法 | |
| US4283545A (en) | Process for the preparation of 1,2,4-triazole | |
| JPS59101441A (ja) | モノ−ニトロ芳香族化合物の製造方法 | |
| US4328369A (en) | Process for the production of 2,6-dinitro-N-alkyl-anilines | |
| US5041691A (en) | Aldol condensation of nitroparaffins | |
| US6794549B2 (en) | Continuous adiabatic process for nitrating chlorobenzene | |
| US3959392A (en) | Process for preparing chlorohydroquinone | |
| US5118487A (en) | Process for producing chlorosulfonyl isocyanate | |
| US3356675A (en) | Production of caprolactam from cyclohexanoyl compounds |