DE2411009C3 - - Google Patents
Info
- Publication number
- DE2411009C3 DE2411009C3 DE19742411009 DE2411009A DE2411009C3 DE 2411009 C3 DE2411009 C3 DE 2411009C3 DE 19742411009 DE19742411009 DE 19742411009 DE 2411009 A DE2411009 A DE 2411009A DE 2411009 C3 DE2411009 C3 DE 2411009C3
- Authority
- DE
- Germany
- Prior art keywords
- temperature
- reaction mixture
- urea
- reaction
- heated
- 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
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 239000004202 carbamide Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N 1,3-di(propan-2-yl)urea Chemical compound CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- AWHORBWDEKTQAX-UHFFFAOYSA-N 1,3-dipropylurea Chemical compound CCCNC(=O)NCCC AWHORBWDEKTQAX-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZYBZYDVRLQSWGG-UHFFFAOYSA-N 2,2-dimethyloct-7-enoic acid Chemical compound OC(=O)C(C)(C)CCCCC=C ZYBZYDVRLQSWGG-UHFFFAOYSA-N 0.000 description 1
- JQUFXTGKSYBEPD-UHFFFAOYSA-N 2-methoxyethylazanium;chloride Chemical compound Cl.COCCN JQUFXTGKSYBEPD-UHFFFAOYSA-N 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742411009 DE2411009B2 (de) | 1974-03-07 | 1974-03-07 | Verfahren zur Herstellung von 1,3-Dialkylharnstoffen |
| CH51375A CH592613A5 (enrdf_load_stackoverflow) | 1974-03-07 | 1975-01-16 | |
| GB843175A GB1489699A (en) | 1974-03-07 | 1975-02-28 | Process for the production of 1,3-dialkyl and di-(alkoxyalkyl)ureas |
| AT165475A AT343127B (de) | 1974-03-07 | 1975-03-04 | Verfahren zur herstellung von 1,3-dialkylharnstoffen |
| FR7506855A FR2263233B1 (enrdf_load_stackoverflow) | 1974-03-07 | 1975-03-05 | |
| NL7502673A NL7502673A (nl) | 1974-03-07 | 1975-03-06 | Werkwijze voor de bereiding van 1,3-dialkylurea. |
| BE154135A BE826437A (fr) | 1974-03-07 | 1975-03-07 | Procede pour fabriquer des 1,3-dialkyl-urees |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742411009 DE2411009B2 (de) | 1974-03-07 | 1974-03-07 | Verfahren zur Herstellung von 1,3-Dialkylharnstoffen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2411009A1 DE2411009A1 (de) | 1975-09-11 |
| DE2411009B2 DE2411009B2 (de) | 1976-01-08 |
| DE2411009C3 true DE2411009C3 (enrdf_load_stackoverflow) | 1976-08-19 |
Family
ID=5909412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742411009 Granted DE2411009B2 (de) | 1974-03-07 | 1974-03-07 | Verfahren zur Herstellung von 1,3-Dialkylharnstoffen |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT343127B (enrdf_load_stackoverflow) |
| BE (1) | BE826437A (enrdf_load_stackoverflow) |
| CH (1) | CH592613A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2411009B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2263233B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1489699A (enrdf_load_stackoverflow) |
| NL (1) | NL7502673A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844962A1 (de) * | 1978-10-16 | 1980-04-30 | Basf Ag | Verfahren zur herstellung von symmetrischen 1,3-disubstituierten harnstoffen |
| AT394715B (de) * | 1990-08-14 | 1992-06-10 | Chemie Linz Gmbh | Verfahren zur n-alkylierung von harnstoffen |
| GB9312881D0 (en) * | 1993-06-22 | 1993-08-04 | Jefferson Roger L | Boiler treatment and novel compounds therfor |
| US5985968A (en) * | 1997-11-17 | 1999-11-16 | Air Products And Chemicals, Inc. | Surface tension reduction with N,N-dialkyl ureas |
-
1974
- 1974-03-07 DE DE19742411009 patent/DE2411009B2/de active Granted
-
1975
- 1975-01-16 CH CH51375A patent/CH592613A5/xx not_active IP Right Cessation
- 1975-02-28 GB GB843175A patent/GB1489699A/en not_active Expired
- 1975-03-04 AT AT165475A patent/AT343127B/de not_active IP Right Cessation
- 1975-03-05 FR FR7506855A patent/FR2263233B1/fr not_active Expired
- 1975-03-06 NL NL7502673A patent/NL7502673A/xx not_active Application Discontinuation
- 1975-03-07 BE BE154135A patent/BE826437A/xx not_active IP Right Cessation
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