IL38719A - Solvent-free process for the preparation of 3 -) lupenyl (- 1, 1 - dialkyl urea - Google Patents
Solvent-free process for the preparation of 3 -) lupenyl (- 1, 1 - dialkyl ureaInfo
- Publication number
- IL38719A IL38719A IL38719A IL3871972A IL38719A IL 38719 A IL38719 A IL 38719A IL 38719 A IL38719 A IL 38719A IL 3871972 A IL3871972 A IL 3871972A IL 38719 A IL38719 A IL 38719A
- Authority
- IL
- Israel
- Prior art keywords
- temperature
- amine
- methyl
- maintained
- reactor
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 title claims description 14
- 150000003672 ureas Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims description 26
- 239000000376 reactant Substances 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 19
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000010923 batch production Methods 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 description 16
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- -1 Isocyanate Amine Chemical class 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical group CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- XANZVOMCLKMKMV-UHFFFAOYSA-N 3,4-dichloroaniline;hydrochloride Chemical compound Cl.NC1=CC=C(Cl)C(Cl)=C1 XANZVOMCLKMKMV-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 229960003887 dichlorophen Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000001953 recrystallisation Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| IL38719A0 IL38719A0 (en) | 1972-04-27 |
| IL38719A true IL38719A (en) | 1974-10-22 |
Family
ID=22594672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38719A IL38719A (en) | 1971-07-20 | 1972-02-08 | Solvent-free process for the preparation of 3 -) lupenyl (- 1, 1 - dialkyl urea |
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 |
| DE2206167C3 (de) | 1974-07-18 |
| GB1336977A (en) | 1973-11-14 |
| DE2206167B2 (de) | 1973-12-13 |
| DE2206167A1 (de) | 1973-03-08 |
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