CA1216304A - Continuous process for the production of methomyl - Google Patents
Continuous process for the production of methomylInfo
- Publication number
- CA1216304A CA1216304A CA000449567A CA449567A CA1216304A CA 1216304 A CA1216304 A CA 1216304A CA 000449567 A CA000449567 A CA 000449567A CA 449567 A CA449567 A CA 449567A CA 1216304 A CA1216304 A CA 1216304A
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- accordance
- temperature
- methomyl
- mixture
- 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.)
- Expired
Links
- 239000005916 Methomyl Substances 0.000 title claims abstract description 23
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 title claims abstract description 21
- 238000010924 continuous production Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 238000004064 recycling Methods 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- AGVHWUQIIQHFCW-DUXPYHPUSA-N (ne)-n-(2-methylsulfanylethylidene)hydroxylamine Chemical compound CSC\C=N\O AGVHWUQIIQHFCW-DUXPYHPUSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 abstract description 2
- 150000002513 isocyanates Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000010923 batch production Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001069 nematicidal effect Effects 0.000 description 3
- 238000011112 process operation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- -1 methyl thioacetal Chemical class 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical class CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000010963 304 stainless steel Substances 0.000 description 1
- 241000982822 Ficus obtusifolia Species 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 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
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000013022 venting Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48049783A | 1983-03-30 | 1983-03-30 | |
| US480,497 | 1983-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1216304A true CA1216304A (en) | 1987-01-06 |
Family
ID=23908189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000449567A Expired CA1216304A (en) | 1983-03-30 | 1984-03-14 | Continuous process for the production of methomyl |
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 AT AT84302169T patent/ATE24175T1/de active
- 1984-03-29 EP EP84302169A patent/EP0121420B1/en not_active Expired
- 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 HU HU841262A patent/HU194538B/hu unknown
- 1984-03-29 ZA ZA842364A patent/ZA842364B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0121420A1 (en) | 1984-10-10 |
| IL71400A0 (en) | 1984-06-29 |
| JPS59184154A (ja) | 1984-10-19 |
| DE3461636D1 (en) | 1987-01-22 |
| ZA842364B (en) | 1984-11-28 |
| JPS6230985B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-07-06 |
| HU194538B (en) | 1988-02-29 |
| ATE24175T1 (de) | 1986-12-15 |
| EP0121420B1 (en) | 1986-12-10 |
| IL71400A (en) | 1987-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |