DE1125419B - Verfahren zur Herstellung von 1, 3-Bis-(ªÏ-carboxyalkyl)-harnstoffen - Google Patents
Verfahren zur Herstellung von 1, 3-Bis-(ªÏ-carboxyalkyl)-harnstoffenInfo
- Publication number
- DE1125419B DE1125419B DEJ18647A DEJ0018647A DE1125419B DE 1125419 B DE1125419 B DE 1125419B DE J18647 A DEJ18647 A DE J18647A DE J0018647 A DEJ0018647 A DE J0018647A DE 1125419 B DE1125419 B DE 1125419B
- Authority
- DE
- Germany
- Prior art keywords
- bis
- carboxyalkyl
- parts
- ureas
- acid
- 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.)
- Pending
Links
- 235000013877 carbamide Nutrition 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 11
- 150000003672 ureas Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000004202 carbamide Substances 0.000 claims description 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- 150000001450 anions Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008240 homogeneous mixture Substances 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- 238000009833 condensation Methods 0.000 description 14
- 230000005494 condensation Effects 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical group CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- -1 1-carboxydecyl Chemical group 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- QFRURJKLPJVRQY-UHFFFAOYSA-N 3-Aminopentanoic acid Chemical compound CCC(N)CC(O)=O QFRURJKLPJVRQY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000010626 work up procedure 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
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1125419X | 1959-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1125419B true DE1125419B (de) | 1962-03-15 |
Family
ID=4558856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ18647A Pending DE1125419B (de) | 1959-09-30 | 1960-08-31 | Verfahren zur Herstellung von 1, 3-Bis-(ªÏ-carboxyalkyl)-harnstoffen |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1125419B (enrdf_load_stackoverflow) |
| NL (2) | NL121510C (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE855551C (de) * | 1942-05-13 | 1952-11-13 | Knoll Ag | Verfahren zur Herstellung von Mono- bzw. symmetrischem Dimethylharnstoff |
-
0
- NL NL256364D patent/NL256364A/xx unknown
- NL NL121510D patent/NL121510C/xx active
-
1960
- 1960-08-31 DE DEJ18647A patent/DE1125419B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE855551C (de) * | 1942-05-13 | 1952-11-13 | Knoll Ag | Verfahren zur Herstellung von Mono- bzw. symmetrischem Dimethylharnstoff |
Also Published As
| Publication number | Publication date |
|---|---|
| NL121510C (enrdf_load_stackoverflow) | |
| NL256364A (enrdf_load_stackoverflow) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0014884B1 (de) | Verfahren zur Aufarbeitung von ammoniumsulfathaltigem Abwasser | |
| DE2517054C2 (de) | Verfahren zur Herstellung von Nicotinsäureamid | |
| CH418332A (de) | Verfahren zur Herstellung von Acylierungsprodukten der phosphorigen Säure mit mindestens 2 Phosphoratomen im Molekül | |
| DE2835450C3 (de) | Verfahren zur Herstellung von 3,3-Bis-(4-dimethylaminophenyl)-6-dimethylaminophthalid (Kristallviolettlacton) | |
| DE1125419B (de) | Verfahren zur Herstellung von 1, 3-Bis-(ªÏ-carboxyalkyl)-harnstoffen | |
| DE2202204C2 (de) | Verfahren zur Herstellung von 2-Mercaptobenzimidazol | |
| EP0050290B1 (de) | Verfahren zur Herstellung von Alkalisalzen der Imidodisulfonsäure | |
| DE1768937A1 (de) | Verfahren zur Herstellung von Nitrilotriacetonitril | |
| DE1493910C3 (de) | Verfahren zur Herstellung von Nitrilotriacetonitril | |
| AT224646B (de) | Verfahren zur Herstellung von 1,3-Bis(ω-carboxyalkyl)-harnstoffen | |
| DE656349C (de) | Verfahren zur Herstellung von Aminonitrilen | |
| DE2738709C2 (de) | Verfahren zur Herstellung von Amidosulfonsäure | |
| AT229876B (de) | Verfahren zur Herstellung von sehr reinem Melamin | |
| DE891259C (de) | Verfahren zur Hydrolyse von Hydantoinen | |
| DE319368C (de) | Verfahren zur Darstellung von Paraldehyd | |
| DE2435167B2 (de) | Verfahren zur Gewinnung von Guanidincarbonat aus verdünnten, wäßrigen Lösungen | |
| DE645725C (de) | Herstellung von Alkalinitraten aus Alkalichloriden und Salpetersaeure | |
| DE933865C (de) | Verfahren zur Herstellung von 2-Aminothiazol | |
| AT252274B (de) | Verfahren zur kontinuierlichen Herstellung von Kaliumbicarbonat | |
| DE535850C (de) | Verfahren zur Herstellung von Ammonsalzen aus ª‡-Oxysaeuren | |
| AT228770B (de) | Verfahren zur Herstellung von ω-Caprolactam | |
| DE554235C (de) | Verfahren zur Darstellung von 2,7-Dioxynaphthalin-3,6-dicarbonsaeure | |
| AT352097B (de) | Verfahren zur herstellung von cyanformamid aus cyanwasserstoff und sauerstoff | |
| AT229332B (de) | Verfahren zur Herstellung von Ammoniumchlorid | |
| DE867091C (de) | Verfahren zur Herstellung von Guanidinsalzen |