TWI614229B - 亞異丁基雙脲之製法 - Google Patents
亞異丁基雙脲之製法 Download PDFInfo
- Publication number
- TWI614229B TWI614229B TW102126107A TW102126107A TWI614229B TW I614229 B TWI614229 B TW I614229B TW 102126107 A TW102126107 A TW 102126107A TW 102126107 A TW102126107 A TW 102126107A TW I614229 B TWI614229 B TW I614229B
- Authority
- TW
- Taiwan
- Prior art keywords
- diurea
- fertilizer
- item
- isobutyl
- phase transfer
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 79
- QFHMNFAUXJAINK-UHFFFAOYSA-N [1-(carbamoylamino)-2-methylpropyl]urea Chemical compound NC(=O)NC(C(C)C)NC(N)=O QFHMNFAUXJAINK-UHFFFAOYSA-N 0.000 title description 3
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 claims abstract description 76
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000004202 carbamide Substances 0.000 claims abstract description 53
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 29
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims abstract description 14
- 238000005580 one pot reaction Methods 0.000 claims abstract description 4
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims abstract description 4
- 239000003337 fertilizer Substances 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 235000015097 nutrients Nutrition 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- 235000013619 trace mineral Nutrition 0.000 claims description 8
- 239000011573 trace mineral Substances 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 239000011814 protection agent Substances 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000006482 condensation reaction Methods 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 2,2,6-trimethylcyclohexyl Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 241000282849 Ruminantia Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000282817 Bovidae Species 0.000 description 2
- 241000282994 Cervidae Species 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- CZAUMIGWDFREBR-UHFFFAOYSA-N (6-methyl-2-oxo-1,3-diazinan-4-yl)urea Chemical compound CC1CC(NC(N)=O)NC(=O)N1 CZAUMIGWDFREBR-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- JMTNOKRGERWNME-UHFFFAOYSA-L 6-[dimethyl-[4-(2,2,6-trimethylcyclohexyl)butan-2-yl]azaniumyl]hexyl-dimethyl-[4-(2,2,6-trimethylcyclohexyl)butan-2-yl]azanium;dichloride Chemical compound [Cl-].[Cl-].CC1CCCC(C)(C)C1CCC(C)[N+](C)(C)CCCCCC[N+](C)(C)C(C)CCC1C(C)CCCC1(C)C JMTNOKRGERWNME-UHFFFAOYSA-L 0.000 description 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
- 241000282979 Alces alces Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 244000303258 Annona diversifolia Species 0.000 description 1
- 235000002198 Annona diversifolia Nutrition 0.000 description 1
- 241000282815 Antilocapra americana Species 0.000 description 1
- 241000283726 Bison Species 0.000 description 1
- 241001416153 Bos grunniens Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000282836 Camelus dromedarius Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 241000282818 Giraffidae Species 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241001416177 Vicugna pacos Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- QRRWWGNBSQSBAM-UHFFFAOYSA-N alumane;chromium Chemical compound [AlH3].[Cr] QRRWWGNBSQSBAM-UHFFFAOYSA-N 0.000 description 1
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- ZUTJDJAXWKOOOI-UHFFFAOYSA-N ethylene diurea Chemical class NC(=O)NCCNC(N)=O ZUTJDJAXWKOOOI-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
- WNVQBUHCOYRLPA-UHFFFAOYSA-N triuret Chemical class NC(=O)NC(=O)NC(N)=O WNVQBUHCOYRLPA-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07C273/1854—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 by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—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 by reactions not involving the formation of the N-C(O)-N- moiety from urea
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C9/00—Fertilisers containing urea or urea compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Fertilizers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ??12005353.3 | 2012-07-23 | ||
| EP12005353 | 2012-07-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201422563A TW201422563A (zh) | 2014-06-16 |
| TWI614229B true TWI614229B (zh) | 2018-02-11 |
Family
ID=49304022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102126107A TWI614229B (zh) | 2012-07-23 | 2013-07-22 | 亞異丁基雙脲之製法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9340495B2 (en:Method) |
| EP (1) | EP2874996B1 (en:Method) |
| CN (1) | CN104507908B (en:Method) |
| AR (1) | AR091863A1 (en:Method) |
| IN (1) | IN2014DN10324A (en:Method) |
| TW (1) | TWI614229B (en:Method) |
| WO (1) | WO2014016745A1 (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106242765A (zh) * | 2016-08-05 | 2016-12-21 | 河南工业大学 | 异丁叉二脲保水缓释肥料的制备方法 |
| WO2018197991A1 (en) | 2017-04-24 | 2018-11-01 | Sabic Global Technologies B.V. | Urea condensation compositions and methods of making the same |
| US11964924B2 (en) | 2018-07-23 | 2024-04-23 | Sabic Global Technologies B.V. | Spherical urea-aldehyde condensate fertilizers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322528A (en) * | 1960-08-30 | 1967-05-30 | Hamamoto Masao | Fertilizer compositions consisting of isobutylidene-diurea and method of using |
| US3962329A (en) * | 1973-11-05 | 1976-06-08 | Basf Aktiengesellschaft | Manufacture of granular isobutylidenediurea |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1146080B (de) | 1960-08-30 | 1963-03-28 | Mitsubishi Chem Ind | Kondensationsprodukte aus Harnstoff und Aldehyden enthaltende Duengemittel |
| GB1069526A (en) | 1963-07-19 | 1967-05-17 | Hoechst Ag | Condensation products of urea and aldehydes and process for making them |
| US3326665A (en) * | 1963-07-19 | 1967-06-20 | Hoechst Ag | Process for the manufacture of granular urea-aldehyde fertilizer |
| GB1099643A (en) | 1964-05-27 | 1968-01-17 | Mitsubishi Chem Ind | Preparation of alkylidene diureas |
| DE1618128A1 (de) | 1967-03-30 | 1970-11-12 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isobutylidendiharnstoff |
| DE1905834C3 (de) | 1969-02-06 | 1972-11-09 | Basf Ag | Verfahren zur Vermeidung des Staubens und Zusammenbackens von Salzen bzw.Duengemitteln |
| US4062890A (en) | 1975-05-23 | 1977-12-13 | Swift Agricultural Chemicals Corporation | Process for manufacture of isobutylidene diurea |
| DD142044A1 (de) | 1979-02-12 | 1980-06-04 | Juergen Freiberg | Verfahren zur herstellung von alkylidendiharnstoffen |
| AT394715B (de) * | 1990-08-14 | 1992-06-10 | Chemie Linz Gmbh | Verfahren zur n-alkylierung von harnstoffen |
| US5169954A (en) * | 1990-08-14 | 1992-12-08 | Chemie Linz Gesellschaft M.B.H. | Process for the N-alkylation of ureas |
| DE4128828A1 (de) | 1991-08-30 | 1993-03-04 | Basf Ag | Ammonium- oder harnstoffhaltige duengemittel und verfahren zu ihrer herstellung |
| DE4302860A1 (de) * | 1993-01-22 | 1994-08-04 | Chemie Linz Deutschland | N-Cyclische und N,N'dicyclische Harnstoffe |
| AT400566B (de) * | 1993-01-22 | 1996-01-25 | Chemie Linz Gmbh | Verwendung und verfahren zur herstellung von n-cyclischen und n,n'-dicyclischen harnstoffen |
| DE19603739A1 (de) | 1996-02-02 | 1997-08-07 | Basf Ag | Granulatmischungen bestehend aus umhüllten und nicht-umhüllten Düngemittelgranulaten |
| DE19631764A1 (de) | 1996-08-06 | 1998-02-12 | Basf Ag | Neue Nitrifikationsinhibitoren sowie die Verwendung von Polysäuren zur Behandlung von Mineraldüngemitteln die einen Nitrifikationsinhibitor enthalten |
| CN101041593A (zh) * | 2007-03-16 | 2007-09-26 | 汉枫缓释肥料（上海）有限公司 | 一种缓释氮肥及其制造方法 |
| CN101759481B (zh) * | 2009-11-20 | 2012-05-16 | 山东金正大生态工程股份有限公司 | 一种高塔缓释复合肥料及其制备方法 |
-
2013
- 2013-07-18 EP EP13773356.4A patent/EP2874996B1/en active Active
- 2013-07-18 CN CN201380039066.5A patent/CN104507908B/zh active Active
- 2013-07-18 US US14/415,039 patent/US9340495B2/en active Active
- 2013-07-18 WO PCT/IB2013/055928 patent/WO2014016745A1/en active Application Filing
- 2013-07-18 IN IN10324DEN2014 patent/IN2014DN10324A/en unknown
- 2013-07-22 TW TW102126107A patent/TWI614229B/zh active
- 2013-07-23 AR ARP130102604A patent/AR091863A1/es active IP Right Grant
-
2016
- 2016-01-15 US US14/996,416 patent/US20160130221A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322528A (en) * | 1960-08-30 | 1967-05-30 | Hamamoto Masao | Fertilizer compositions consisting of isobutylidene-diurea and method of using |
| US3962329A (en) * | 1973-11-05 | 1976-06-08 | Basf Aktiengesellschaft | Manufacture of granular isobutylidenediurea |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201422563A (zh) | 2014-06-16 |
| WO2014016745A1 (en) | 2014-01-30 |
| US20160130221A1 (en) | 2016-05-12 |
| IN2014DN10324A (en:Method) | 2015-08-07 |
| AU2013294659B2 (en) | 2015-12-24 |
| US20150183729A1 (en) | 2015-07-02 |
| CN104507908B (zh) | 2017-06-23 |
| EP2874996B1 (en) | 2019-11-20 |
| CN104507908A (zh) | 2015-04-08 |
| US9340495B2 (en) | 2016-05-17 |
| EP2874996A1 (en) | 2015-05-27 |
| AU2013294659A1 (en) | 2015-01-15 |
| AR091863A1 (es) | 2015-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2007334242B2 (en) | Extended-release urea-based granular fertilizer | |
| AU2013395556B2 (en) | Method and liquid compound that improves the efficiency of ammoniacal nitrogenated fertilisers and the ammonium present in the ground | |
| CN108473383A (zh) | 含n-正丁基硫代磷酰三胺加合物和反应产物的组合物 | |
| TWI614229B (zh) | 亞異丁基雙脲之製法 | |
| CN111448175A (zh) | 基于磷酸的烷醇胺盐的新型磷肥 | |
| CN110691772B (zh) | 脲缩合组合物及其制备方法 | |
| CN106278764B (zh) | 一种制备含有微胶囊型肥料增效剂的复合肥的方法及其制得的复合肥 | |
| JP5805742B2 (ja) | 緩効性液状肥料及びその製造方法 | |
| AU2013294659B9 (en) | Process for the preparation of isobutylidene diurea | |
| CN119768383A (zh) | 通过脱碳并利用硫酸钙生产氮、钾、硫养分 | |
| CN101734968A (zh) | 一种生产硫基复合肥的方法 | |
| RU2808272C2 (ru) | Смесь, включающая азотсодержащее удобрение, ингибитор нитрификации и композицию, включающую первичные и/или вторичные алкил- и/или алкиленмоноамины | |
| RU2808271C2 (ru) | Способ получения композиции удобрения, содержащей ингибитор нитрификации dmpsa, путем добавления dmpsa или её солей в расплав удобрения | |
| EP4317121B1 (en) | Process for obtaining a fertilizer composition comprising a dmpsa nitrification inhibitor via adding dmpsa salts into the fertilizer melt | |
| EP4416120A1 (en) | Method for producing a potassium-containing fertilizer with a low content of water-insoluble material | |
| WO2025186742A1 (en) | Production of nitrogen, potassium, sulfur nutrient through de-carbonization and utilization of calcium sulfate | |
| WO2024003864A1 (en) | Methods for preparation of ca nutrient to support carbon neutrality | |
| WO2020127870A1 (en) | Process for obtaining a fertilizer composition comprising a dmpsa nitrification inhibitor via adding dmpsa or the salts thereof into the fertilizer melt | |
| CN102351587A (zh) | 利用亚氨基二乙腈及其废母液生产高效肥的方法 | |
| BG111063A (bg) | Комплексен течен тор |