DE2206167C3 - Herstellung von herbicid wirksamen 3-(Halogenphenyl)-1,1 -dialkylharnstoffen - Google Patents
Herstellung von herbicid wirksamen 3-(Halogenphenyl)-1,1 -dialkylharnstoffenInfo
- Publication number
- DE2206167C3 DE2206167C3 DE2206167A DE2206167A DE2206167C3 DE 2206167 C3 DE2206167 C3 DE 2206167C3 DE 2206167 A DE2206167 A DE 2206167A DE 2206167 A DE2206167 A DE 2206167A DE 2206167 C3 DE2206167 C3 DE 2206167C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- amine
- solvent
- halogen
- isocyanate
- 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
- 125000005059 halophenyl group Chemical group 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 210000002700 urine Anatomy 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- 235000019441 ethanol Nutrition 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000012452 mother liquor Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- XANZVOMCLKMKMV-UHFFFAOYSA-N 3,4-dichloroaniline;hydrochloride Chemical compound Cl.NC1=CC=C(Cl)C(Cl)=C1 XANZVOMCLKMKMV-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- -1 isocyanate salt Chemical class 0.000 description 5
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- DVMXUBXASQPMOI-UHFFFAOYSA-N 1-methyl-1-propan-2-ylurea Chemical compound CC(C)N(C)C(N)=O DVMXUBXASQPMOI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00164478A US3850986A (en) | 1971-07-20 | 1971-07-20 | Solvent-free process for 3-(halophenyl)-1,1-dialkyl ureas |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2206167A1 DE2206167A1 (de) | 1973-03-08 |
| DE2206167B2 DE2206167B2 (de) | 1973-12-13 |
| DE2206167C3 true DE2206167C3 (de) | 1974-07-18 |
Family
ID=22594672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206167A Expired DE2206167C3 (de) | 1971-07-20 | 1972-02-09 | Herstellung von herbicid wirksamen 3-(Halogenphenyl)-1,1 -dialkylharnstoffen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3850986A (enExample) |
| DE (1) | DE2206167C3 (enExample) |
| FR (1) | FR2146713A5 (enExample) |
| GB (1) | GB1336977A (enExample) |
| IL (1) | IL38719A (enExample) |
| MY (1) | MY7500191A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105294504A (zh) * | 2015-10-20 | 2016-02-03 | 安徽广信农化股份有限公司 | 一种敌草隆的合成方法 |
| CN105294503B (zh) * | 2015-10-20 | 2017-09-12 | 安徽广信农化股份有限公司 | 一种敌草隆的提纯工艺 |
| CN107129445A (zh) * | 2017-06-07 | 2017-09-05 | 江苏蓝丰生物化工股份有限公司 | 一种敌草隆的合成方法 |
| EP4556462A1 (de) | 2023-11-17 | 2025-05-21 | LANXESS Deutschland GmbH | Verfahren zur herstellung von substituierten phenylharnstoffderivaten |
-
1971
- 1971-07-20 US US00164478A patent/US3850986A/en not_active Expired - Lifetime
-
1972
- 1972-02-08 IL IL38719A patent/IL38719A/en unknown
- 1972-02-09 DE DE2206167A patent/DE2206167C3/de not_active Expired
- 1972-02-21 FR FR7205728A patent/FR2146713A5/fr not_active Expired
- 1972-03-06 GB GB1035972A patent/GB1336977A/en not_active Expired
-
1975
- 1975-12-30 MY MY191/75A patent/MY7500191A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL38719A0 (en) | 1972-04-27 |
| MY7500191A (en) | 1975-12-31 |
| FR2146713A5 (enExample) | 1973-03-02 |
| US3850986A (en) | 1974-11-26 |
| GB1336977A (en) | 1973-11-14 |
| DE2206167B2 (de) | 1973-12-13 |
| DE2206167A1 (de) | 1973-03-08 |
| IL38719A (en) | 1974-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |