CA1258189A - Triazone fertilizer and method of making - Google Patents
Triazone fertilizer and method of makingInfo
- Publication number
- CA1258189A CA1258189A CA000488768A CA488768A CA1258189A CA 1258189 A CA1258189 A CA 1258189A CA 000488768 A CA000488768 A CA 000488768A CA 488768 A CA488768 A CA 488768A CA 1258189 A CA1258189 A CA 1258189A
- Authority
- CA
- Canada
- Prior art keywords
- triazone
- urea
- ammonia
- compounds
- compound
- 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
- 239000003337 fertilizer Substances 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 158
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 136
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 97
- 239000004202 carbamide Substances 0.000 claims abstract description 78
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 72
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000000376 reactant Substances 0.000 claims abstract description 42
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- KQVLODRFGIKJHZ-UHFFFAOYSA-N methylenediurea Chemical compound NC(=O)NCNC(N)=O KQVLODRFGIKJHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000010438 heat treatment Methods 0.000 claims abstract description 28
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 16
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 16
- 150000003672 ureas Chemical class 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- 239000007787 solid Substances 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 14
- UZZLUFRHLWXBAH-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(tetrazol-1-yl)propane-1,3-diol Chemical compound OCC(CO)(CO)N1C=NN=N1 UZZLUFRHLWXBAH-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 42
- -1 compound methylene diurea compound Chemical class 0.000 claims description 33
- 239000000047 product Substances 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 29
- 239000007795 chemical reaction product Substances 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims description 4
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims description 4
- KNEVEAGWWYBVNM-UHFFFAOYSA-N 3-methyltriazin-4-one Chemical compound CN1N=NC=CC1=O KNEVEAGWWYBVNM-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 4
- 239000003518 caustics Substances 0.000 abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 description 57
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 150000001299 aldehydes Chemical class 0.000 description 20
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 17
- 229950005308 oxymethurea Drugs 0.000 description 17
- 238000007792 addition Methods 0.000 description 13
- 229960004011 methenamine Drugs 0.000 description 13
- 235000019256 formaldehyde Nutrition 0.000 description 10
- 229960004279 formaldehyde Drugs 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 229920001807 Urea-formaldehyde Polymers 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001547070 Eriodes Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000007799 dermal corrosion Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ZUTJDJAXWKOOOI-UHFFFAOYSA-N ethylene diurea Chemical compound NC(=O)NCCNC(N)=O ZUTJDJAXWKOOOI-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 231100000108 skin corrosion Toxicity 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C9/00—Fertilisers containing urea or urea compounds
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C9/00—Fertilisers containing urea or urea compounds
- C05C9/02—Fertilisers containing urea or urea compounds containing urea-formaldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G5/00—Fertilisers characterised by their form
- C05G5/20—Liquid fertilisers
- C05G5/23—Solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Fertilizers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US644,975 | 1984-08-28 | ||
| US06/644,975 US4554005A (en) | 1984-08-28 | 1984-08-28 | Triazone fertilizer and method of making |
| US75780785A | 1985-07-22 | 1985-07-22 | |
| US757,807 | 1985-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1258189A true CA1258189A (en) | 1989-08-08 |
Family
ID=27094599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000488768A Expired CA1258189A (en) | 1984-08-28 | 1985-08-15 | Triazone fertilizer and method of making |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU588824B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1258189A (enrdf_load_stackoverflow) |
| DE (1) | DE3530329A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2569685B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2164929B (enrdf_load_stackoverflow) |
| IT (1) | IT1201351B (enrdf_load_stackoverflow) |
| NL (1) | NL8502239A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017156464A1 (en) * | 2016-03-11 | 2017-09-14 | Oms Investments, Inc. | Iron-supplemented fertilizer |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6632262B2 (en) * | 2000-08-22 | 2003-10-14 | Georgia-Pacific Resins, Inc. | Controlled release urea-formaldehyde liquid fertilizer resins |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2826500A (en) * | 1954-12-30 | 1958-03-11 | Hercules Powder Co Ltd | Use of cationic-modified urea-formaldehyde resins in the manufacture of wet strengthpaper |
| GB976713A (en) * | 1961-08-18 | 1964-12-02 | Swift & Co | Improvements in or relating to stable urea-formaldehyde suspensions |
| US3462256A (en) * | 1966-10-31 | 1969-08-19 | Allied Chem | Process for producing urea-formaledhyde aqueous concentrates |
| DD115566A1 (enrdf_load_stackoverflow) * | 1974-02-04 | 1975-10-12 | ||
| US4244727A (en) * | 1979-02-07 | 1981-01-13 | Ashland Oil, Inc. | Urea-formaldehyde solution for foliar fertilization |
| US4304588A (en) * | 1980-05-05 | 1981-12-08 | Moore Jr William P | Foliar feed compositions |
| AU552437B2 (en) * | 1981-11-09 | 1986-05-29 | Liqui-Box Corp. | Coupling and valve assembly for a liquid dispenser |
-
1985
- 1985-08-13 NL NL8502239A patent/NL8502239A/nl not_active Application Discontinuation
- 1985-08-15 CA CA000488768A patent/CA1258189A/en not_active Expired
- 1985-08-24 DE DE19853530329 patent/DE3530329A1/de active Granted
- 1985-08-27 GB GB08521313A patent/GB2164929B/en not_active Expired
- 1985-08-27 FR FR858512761A patent/FR2569685B1/fr not_active Expired - Lifetime
- 1985-08-27 IT IT09486/85A patent/IT1201351B/it active
- 1985-08-28 AU AU46897/85A patent/AU588824B2/en not_active Ceased
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017156464A1 (en) * | 2016-03-11 | 2017-09-14 | Oms Investments, Inc. | Iron-supplemented fertilizer |
| US11208360B2 (en) | 2016-03-11 | 2021-12-28 | Oms Investments, Inc. | Iron-supplemented fertilizer |
| US11905225B2 (en) | 2016-03-11 | 2024-02-20 | Oms Investments, Inc. | Iron-supplemented fertilizer |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3530329A1 (de) | 1986-05-15 |
| IT8509486A0 (it) | 1985-08-27 |
| FR2569685A1 (fr) | 1986-03-07 |
| AU588824B2 (en) | 1989-09-28 |
| AU4689785A (en) | 1986-03-06 |
| GB8521313D0 (en) | 1985-10-02 |
| IT1201351B (it) | 1989-01-27 |
| GB2164929B (en) | 1988-05-11 |
| DE3530329C2 (enrdf_load_stackoverflow) | 1991-12-19 |
| NL8502239A (nl) | 1986-03-17 |
| FR2569685B1 (fr) | 1991-03-29 |
| GB2164929A (en) | 1986-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |