DE2152550C3 - Verfahren zur Herstellung eines vorwiegend Biuret enthaltenden Gemisches von Autokondensationsprodukten des Harnstoffes - Google Patents
Verfahren zur Herstellung eines vorwiegend Biuret enthaltenden Gemisches von Autokondensationsprodukten des HarnstoffesInfo
- Publication number
- DE2152550C3 DE2152550C3 DE2152550A DE2152550A DE2152550C3 DE 2152550 C3 DE2152550 C3 DE 2152550C3 DE 2152550 A DE2152550 A DE 2152550A DE 2152550 A DE2152550 A DE 2152550A DE 2152550 C3 DE2152550 C3 DE 2152550C3
- Authority
- DE
- Germany
- Prior art keywords
- urea
- biuret
- heating
- products
- mixture
- 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
- 239000004202 carbamide Substances 0.000 title claims description 44
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 38
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000047 product Substances 0.000 claims description 40
- 239000007788 liquid Substances 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 241000282849 Ruminantia Species 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000012188 paraffin wax Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- WNVQBUHCOYRLPA-UHFFFAOYSA-N triuret Chemical compound NC(=O)NC(=O)NC(N)=O WNVQBUHCOYRLPA-UHFFFAOYSA-N 0.000 claims description 7
- 229920000877 Melamine resin Polymers 0.000 claims description 6
- 238000007792 addition Methods 0.000 claims description 6
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 claims description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- VYKGZYAKGHXTNC-UHFFFAOYSA-N 2-nonyl-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1(CCCCCCCCC)CO1 VYKGZYAKGHXTNC-UHFFFAOYSA-N 0.000 claims 1
- 101150049168 Nisch gene Proteins 0.000 claims 1
- 208000000260 Warts Diseases 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 210000003298 dental enamel Anatomy 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000012263 liquid product Substances 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 239000000523 sample Substances 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 201000010153 skin papilloma Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
- 210000004767 rumen Anatomy 0.000 description 10
- 239000012530 fluid Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 231100001225 mammalian toxicity Toxicity 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000037 vitreous enamel Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- 206010016717 Fistula Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- -1 myristyl dimethyl benzyl ammonium chloride cyanuric acid Chemical compound 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing 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
- C07C273/1872—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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
- A23K50/15—Feeding-stuffs specially adapted for particular animals for ruminants containing substances which are metabolically converted to proteins, e.g. ammonium salts or urea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Birds (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA707156A ZA707156B (en) | 1970-10-21 | 1970-10-21 | Auto-condensation products of urea |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2152550A1 DE2152550A1 (de) | 1972-04-27 |
| DE2152550B2 DE2152550B2 (de) | 1974-11-14 |
| DE2152550C3 true DE2152550C3 (de) | 1975-06-26 |
Family
ID=25562617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2152550A Expired DE2152550C3 (de) | 1970-10-21 | 1971-10-21 | Verfahren zur Herstellung eines vorwiegend Biuret enthaltenden Gemisches von Autokondensationsprodukten des Harnstoffes |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS516052B1 (enrdf_load_stackoverflow) |
| AU (1) | AU451816B2 (enrdf_load_stackoverflow) |
| CA (1) | CA976189A (enrdf_load_stackoverflow) |
| DE (1) | DE2152550C3 (enrdf_load_stackoverflow) |
| ES (1) | ES396245A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2113063A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1324738A (enrdf_load_stackoverflow) |
| NL (1) | NL142951B (enrdf_load_stackoverflow) |
| ZA (1) | ZA707156B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| 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 |
| EP3995488A1 (en) | 2020-11-06 | 2022-05-11 | Casale Sa | Process for producing feed-grade urea |
| EP4285735A1 (en) * | 2022-06-03 | 2023-12-06 | Yara International ASA | Use of a mixture of urea, biuret and minor n-containing compounds created during biuret prouction as a dietary npn-source in a ruminant feed supplement composition |
| EP4478895A1 (en) * | 2022-02-17 | 2024-12-25 | Yara International ASA | A mixture of urea, biuret and n-containing by-products created during biuret production as a dietary non-protein nitrogen-source for ruminants and uses thereof |
| EP4230056A1 (en) * | 2022-02-17 | 2023-08-23 | Yara International ASA | Use of a ruminant feed supplement composition as a non-protein nitrogen source to improve rumen fermentation, the productivity and performance of the ruminant animals and the enteric methane emission |
| EP4512251A1 (en) * | 2023-08-23 | 2025-02-26 | Yara International ASA | Ruminant feed additive compositions having methane inhibition properties |
| WO2025040777A1 (en) * | 2023-08-23 | 2025-02-27 | Yara International Asa | Method for producing solid particles comprising urea, biuret, and n-containing compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB830114A (en) * | 1957-06-18 | 1960-03-09 | Stamicarbon | Process of preparing biuret from urea |
| BR6687256D0 (pt) * | 1966-02-24 | 1973-12-26 | E Kamlet | Fertilizantes nitrogenados e processo para fazer os mesmo |
-
1970
- 1970-10-21 ZA ZA707156A patent/ZA707156B/xx unknown
-
1971
- 1971-10-13 GB GB4767771A patent/GB1324738A/en not_active Expired
- 1971-10-15 AU AU34682/71A patent/AU451816B2/en not_active Expired
- 1971-10-20 CA CA125,683A patent/CA976189A/en not_active Expired
- 1971-10-21 FR FR7137866A patent/FR2113063A5/fr not_active Expired
- 1971-10-21 DE DE2152550A patent/DE2152550C3/de not_active Expired
- 1971-10-21 JP JP7183644A patent/JPS516052B1/ja active Pending
- 1971-10-21 ES ES71396245A patent/ES396245A1/es not_active Expired
- 1971-10-21 NL NL717114489A patent/NL142951B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA707156B (en) | 1972-06-28 |
| JPS516052B1 (enrdf_load_stackoverflow) | 1976-02-25 |
| GB1324738A (en) | 1973-07-25 |
| AU3468271A (en) | 1973-04-19 |
| CA976189A (en) | 1975-10-14 |
| ES396245A1 (es) | 1974-04-16 |
| NL7114489A (enrdf_load_stackoverflow) | 1972-04-25 |
| NL142951B (nl) | 1974-08-15 |
| DE2152550B2 (de) | 1974-11-14 |
| AU451816B2 (en) | 1974-08-22 |
| FR2113063A5 (enrdf_load_stackoverflow) | 1972-06-23 |
| DE2152550A1 (de) | 1972-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |