DE2049294C3 - Verfahren zur Herstellung eines im wesentlichen aus Biuret bestehenden Produkts - Google Patents
Verfahren zur Herstellung eines im wesentlichen aus Biuret bestehenden ProduktsInfo
- Publication number
- DE2049294C3 DE2049294C3 DE2049294A DE2049294A DE2049294C3 DE 2049294 C3 DE2049294 C3 DE 2049294C3 DE 2049294 A DE2049294 A DE 2049294A DE 2049294 A DE2049294 A DE 2049294A DE 2049294 C3 DE2049294 C3 DE 2049294C3
- Authority
- DE
- Germany
- Prior art keywords
- urea
- biuret
- ether
- glycol
- diether
- 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
- 238000000034 method Methods 0.000 title claims description 22
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 title claims description 20
- 230000008569 process Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000004202 carbamide Substances 0.000 claims description 29
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- -1 Glycol ethers Chemical class 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WNVQBUHCOYRLPA-UHFFFAOYSA-N triuret Chemical compound NC(=O)NC(=O)NC(N)=O WNVQBUHCOYRLPA-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 description 1
- AETIPHBKCCVQJU-UHFFFAOYSA-N 1-ethoxy-2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethane Chemical compound CCOCCOCCOCCOCCOCCOCCOCC AETIPHBKCCVQJU-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010061380 Therapeutic reaction time decreased Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07C273/1872—Preparation of compounds comprising a -N-C(O)-N-C(O)-N- moiety
- C07C273/1881—Preparation of compounds comprising a -N-C(O)-N-C(O)-N- moiety from urea
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 |
|---|---|---|---|
| US86520869A | 1969-10-09 | 1969-10-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2049294A1 DE2049294A1 (de) | 1971-04-22 |
| DE2049294B2 DE2049294B2 (de) | 1973-04-26 |
| DE2049294C3 true DE2049294C3 (de) | 1973-11-22 |
Family
ID=25344949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2049294A Expired DE2049294C3 (de) | 1969-10-09 | 1970-10-07 | Verfahren zur Herstellung eines im wesentlichen aus Biuret bestehenden Produkts |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT308134B (enExample) |
| BE (1) | BE757245A (enExample) |
| CS (1) | CS154671B2 (enExample) |
| DE (1) | DE2049294C3 (enExample) |
| ES (1) | ES384309A1 (enExample) |
| FR (1) | FR2065102A5 (enExample) |
| GB (1) | GB1324277A (enExample) |
| HU (1) | HU162951B (enExample) |
| NL (1) | NL7014831A (enExample) |
| PL (1) | PL81096B1 (enExample) |
| ZA (1) | ZA706628B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100798109B1 (ko) | 2006-08-11 | 2008-01-28 | 주식회사 제이앤드제이 캐미칼 | 뷰렛 및 시아누르산의 제조 방법 및 그 제조 장치 |
-
0
- BE BE757245D patent/BE757245A/xx unknown
-
1970
- 1970-09-29 ZA ZA706628*A patent/ZA706628B/xx unknown
- 1970-10-07 DE DE2049294A patent/DE2049294C3/de not_active Expired
- 1970-10-07 ES ES384309A patent/ES384309A1/es not_active Expired
- 1970-10-07 FR FR7036145A patent/FR2065102A5/fr not_active Expired
- 1970-10-08 PL PL1970143825A patent/PL81096B1/pl unknown
- 1970-10-08 GB GB4793470A patent/GB1324277A/en not_active Expired
- 1970-10-08 CS CS680370A patent/CS154671B2/cs unknown
- 1970-10-08 AT AT909170A patent/AT308134B/de not_active IP Right Cessation
- 1970-10-09 HU HUCE788A patent/HU162951B/hu unknown
- 1970-10-09 NL NL7014831A patent/NL7014831A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS154671B2 (enExample) | 1974-04-30 |
| FR2065102A5 (enExample) | 1971-07-23 |
| AT308134B (de) | 1973-06-25 |
| GB1324277A (en) | 1973-07-25 |
| BE757245A (fr) | 1971-04-08 |
| NL7014831A (enExample) | 1971-04-14 |
| HU162951B (enExample) | 1973-05-28 |
| ES384309A1 (es) | 1973-04-16 |
| DE2049294B2 (de) | 1973-04-26 |
| ZA706628B (en) | 1971-10-27 |
| PL81096B1 (enExample) | 1975-08-30 |
| DE2049294A1 (de) | 1971-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |