JP2019504845A - 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 - Google Patents
高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 Download PDFInfo
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- JP2019504845A JP2019504845A JP2018539990A JP2018539990A JP2019504845A JP 2019504845 A JP2019504845 A JP 2019504845A JP 2018539990 A JP2018539990 A JP 2018539990A JP 2018539990 A JP2018539990 A JP 2018539990A JP 2019504845 A JP2019504845 A JP 2019504845A
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- urea
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- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 102
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 150000001412 amines Chemical class 0.000 claims abstract description 55
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000000411 inducer Substances 0.000 claims abstract description 38
- 229910002090 carbon oxide Inorganic materials 0.000 claims abstract description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims description 43
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 38
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 33
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 31
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 22
- 239000004202 carbamide Substances 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 10
- JUENUKVUHZSJQM-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;urea Chemical compound NC(N)=O.NCCNCCN JUENUKVUHZSJQM-UHFFFAOYSA-N 0.000 claims description 3
- OSIBRFXOURCHFT-UHFFFAOYSA-N 2-aminoethanol;carbamic acid Chemical compound NCCO.NC(O)=O OSIBRFXOURCHFT-UHFFFAOYSA-N 0.000 claims description 2
- 229940031098 ethanolamine Drugs 0.000 claims 6
- 235000013877 carbamide Nutrition 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- -1 cyclic secondary amine Chemical class 0.000 description 20
- 239000005977 Ethylene Substances 0.000 description 18
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 12
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000006268 reductive amination reaction Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000008040 ionic compounds Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 3
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 2
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000005891 transamination reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WMGHTDYMKSKOJP-UHFFFAOYSA-N 1,4-diaminobutan-2-yl carbamate Chemical group NCCC(CN)OC(N)=O WMGHTDYMKSKOJP-UHFFFAOYSA-N 0.000 description 1
- MUFOUZQZXUBRKW-UHFFFAOYSA-N 1-(2-aminoethylamino)ethyl carbamate Chemical compound C(N)(=O)OC(C)NCCN MUFOUZQZXUBRKW-UHFFFAOYSA-N 0.000 description 1
- GEMPJWWBTUXRBX-UHFFFAOYSA-N 2,2-diaminoethylurea Chemical compound NC(CNC(=O)N)N GEMPJWWBTUXRBX-UHFFFAOYSA-N 0.000 description 1
- HVOBSBRYQIYZNY-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethanol Chemical group NCCNCCNCCO HVOBSBRYQIYZNY-UHFFFAOYSA-N 0.000 description 1
- OCKYRUXIGBXXSZ-UHFFFAOYSA-N 2-piperazin-1-ylethane-1,1-diamine Chemical compound NC(N)CN1CCNCC1 OCKYRUXIGBXXSZ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001715 carbamic acids Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011985 exploratory data analysis Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- TWOKQHDORBJKRS-UHFFFAOYSA-N n'-[2-[2-(ethylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CCNCCNCCNCCN TWOKQHDORBJKRS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Chemical group 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940066765 systemic antihistamines substituted ethylene diamines Drugs 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- 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
- C07C273/1809—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 with formation of the N-C(O)-N moiety
-
- 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
- C07C273/1809—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 with formation of the N-C(O)-N moiety
- C07C273/1836—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 with formation of the N-C(O)-N moiety from derivatives of carbamic acid
-
- 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
-
- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/02—Polyureas
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
1モルのAEEAを、1モルの尿素と、オートクレーブ中で、170℃で0.5時間反応させた。以下のGC分析は、AEEAの93%がUAEEAに転換されたことを示した。オートクレーブを通気させた後、1.2モルのEDAおよび0.2モルの尿素を添加し、その後、温度を280℃まで上昇させ、5時間一定に保持した。この反応混合物のGC−分析は、2.1%のL−TETAおよび27.5%のUTETA(すなわち、3つの異なるUTETA類の合計)を示した。
3モルのEDA、1モルのAEEAおよび1.65モルの尿素を、密閉圧力容器中で、280℃で2時間反応させた。反応混合物のGC分析は、2.9%のL−TETAおよび11.6%のUTETA(すなわち、3つの異なるUTETA類の合計)を示した。室温へ冷却した後、混合物を、次いで、4gのNaOHおよび20gの水を用いて、200℃で1時間加水分解した。GC−FID分析(水を含まない)は、液相が9.1%のL−TETAおよび2%のUTETA類を含有することを示した。
1モルのAEEA、1モルのEUおよび2モルのEDAを、密閉圧力容器中で、300℃で6時間反応させた。反応混合物のGC分析は、2.4%のL−TETAおよび18.8%のUTETA(すなわち、3つの異なるUTETA類の合計)を示した。
1モルのAEEAおよび1.1モルの尿素を、密閉圧力容器中で、170℃で1.5時間反応させた。反応容器を、次いで室温へ冷却し、この温度で蓋を取り外し、1モルのEUを添加した。次いで、再び蓋を閉じた容器を280℃まで加熱し、この温度で5時間保持した。
1モルのUAEEA、1.7モルのEUおよび0.3モルのEDAを、密閉圧力容器中で、270℃で5時間反応させた。GC−FID分析は、40.7%のL−TETA(UTETA類)の尿素前駆体を示した。試料は加水分解しなかった。
DETAを、モル当量が0.5から2.0の範囲のCMEAと、密閉圧力容器中で、275℃で4時間反応させた。CMEAは、エタノールアミンとCO源の2つの役割を果たし、CO/アミンおよびエタノールアミン/アミンの比は、CMEA/DETAの比と等しい。主成分の重量分率は生成物混合物のGC−FID分析によって決定され、それらのCO含有誘導体を含む高級エチレンアミンの収率が、CMEA/DETA比に伴って上昇することを明らかに示す。全ての比において、テトラミン(TETA)が大部分を占める。CMEAと初期に形成されたTETAの間の逐次反応を想定して予測されるように、より高い比において、ペンタアミンおよびペンタアミンより高級のエチレンアミン(≧TEPA)の相対量は増加する。
[1]
酸化炭素誘導剤の存在下でエタノールアミン官能性化合物、アミン官能性化合物を反応させることによって、式NH 2 −(C 2 H 4 −NH−) p H(式中、pは、少なくとも3である)のエチレンアミンまたはその誘導体(ここで、1つまたは複数の−NH−C 2 H 4 −NH−単位は、環状エチレン尿素単位
[2]
酸化炭素誘導剤とアミン官能性化合物のモル比が、0.7:1から20:1の間である、上記[1]に記載の方法。
[3]
前記エタノールアミン官能性化合物および前記酸化炭素誘導剤が、カルバメート付加物を用いて、少なくとも部分的に1つの化合物として添加される、上記[1]または[2]に記載の方法。
[4]
前記アミン官能性化合物および前記酸化炭素誘導剤が、尿素付加物を用いて、少なくとも部分的に1つの化合物として添加される、上記[1]から[3]のいずれか一項に記載の方法。
[5]
前記エタノールアミン官能性化合物が、式OH−(C 2 H 4 −NH−) q H(式中、qは少なくとも1である)のものであり、
前記アミン官能性化合物が、式NH 2 −(C 2 H 4 −NH−) r H(式中、rは少なくとも1である)のものであって、
q+rの合計は少なくとも3であり、任意選択的に1つまたは複数のqまたはr単位は、環状エチレン尿素、または環状エチレンカルバメート単位として存在してもよい、
上記[1]から[4]のいずれか一項に記載の方法。
[6]
次に、得られた環状エチレン尿素をその対応するエチレンアミンへ変換するステップが行われる、上記[1]から[5]のいずれか一項に記載の方法。
[7]
前記エタノールアミン官能性化合物が、AEEA(アミノエチルエタノールアミン)、CAEEA(アミノエチルエタノールアミンのカルバメート)、UAEEA(アミノエチルエタノールアミンの尿素)またはそれらの混合物であり、
前記アミン官能性化合物が、EDA(エチレンジアミン)、EU(エチレン尿素)またはそれらの混合物である、上記[1]から[6]のいずれか一項に記載の方法。
[8]
AEEA、UAEEA+CAEEAとEDA+EUの比が、1と等しいか、または1より大きい、上記[7]に記載の方法。
[9]
前記エタノールアミン官能性化合物が、MEA(モノエタノールアミン)、CMEA(モノエタノールアミンのカルバメート)またはそれらの混合物であり、
前記アミン官能性化合物が、DETA(ジエチレントリアミン)、UDETA(ジエチレントリアミンの尿素)またはそれらの混合物である、上記[1]から[6]のいずれか一項に記載の方法。
[10]
MEA+CMEAとDETA+UDETAの比が、1より大きく、好ましくは、2より大きい、上記[9]に記載の方法。
[11]
前記エタノールアミン官能性化合物が、MEA、CMEAまたはそれらの混合物であり、
前記アミン官能性化合物が、EDA、EUまたはそれらの混合物である、上記[1]から[6]のいずれか一項に記載の方法。
[12]
MEA+CMEAとEDA+EUの比が、2より大きく、好ましくは、3より大きい、上記[11]に記載の方法。
Claims (12)
- 酸化炭素誘導剤の存在下でエタノールアミン官能性化合物、アミン官能性化合物を反応させることによって、式NH2−(C2H4−NH−)pH(式中、pは、少なくとも3である)のエチレンアミンまたはその誘導体(ここで、1つまたは複数の−NH−C2H4−NH−単位は、環状エチレン尿素単位
- 酸化炭素誘導剤とアミン官能性化合物のモル比が、0.7:1から20:1の間である、請求項1に記載の方法。
- 前記エタノールアミン官能性化合物および前記酸化炭素誘導剤が、カルバメート付加物を用いて、少なくとも部分的に1つの化合物として添加される、請求項1または2に記載の方法。
- 前記アミン官能性化合物および前記酸化炭素誘導剤が、尿素付加物を用いて、少なくとも部分的に1つの化合物として添加される、請求項1から3のいずれか一項に記載の方法。
- 前記エタノールアミン官能性化合物が、式OH−(C2H4−NH−)qH(式中、qは少なくとも1である)のものであり、
前記アミン官能性化合物が、式NH2−(C2H4−NH−)rH(式中、rは少なくとも1である)のものであって、
q+rの合計は少なくとも3であり、任意選択的に1つまたは複数のqまたはr単位は、環状エチレン尿素、または環状エチレンカルバメート単位として存在してもよい、
請求項1から4のいずれか一項に記載の方法。 - 次に、得られた環状エチレン尿素をその対応するエチレンアミンへ変換するステップが行われる、請求項1から5のいずれか一項に記載の方法。
- 前記エタノールアミン官能性化合物が、AEEA(アミノエチルエタノールアミン)、CAEEA(アミノエチルエタノールアミンのカルバメート)、UAEEA(アミノエチルエタノールアミンの尿素)またはそれらの混合物であり、
前記アミン官能性化合物が、EDA(エチレンジアミン)、EU(エチレン尿素)またはそれらの混合物である、請求項1から6のいずれか一項に記載の方法。 - AEEA、UAEEA+CAEEAとEDA+EUの比が、1と等しいか、または1より大きい、請求項7に記載の方法。
- 前記エタノールアミン官能性化合物が、MEA(モノエタノールアミン)、CMEA(モノエタノールアミンのカルバメート)またはそれらの混合物であり、
前記アミン官能性化合物が、DETA(ジエチレントリアミン)、UDETA(ジエチレントリアミンの尿素)またはそれらの混合物である、請求項1から6のいずれか一項に記載の方法。 - MEA+CMEAとDETA+UDETAの比が、1より大きく、好ましくは、2より大きい、請求項9に記載の方法。
- 前記エタノールアミン官能性化合物が、MEA、CMEAまたはそれらの混合物であり、
前記アミン官能性化合物が、EDA、EUまたはそれらの混合物である、請求項1から6のいずれか一項に記載の方法。 - MEA+CMEAとEDA+EUの比が、2より大きく、好ましくは、3より大きい、請求項11に記載の方法。
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EP3414222B1 (en) | 2016-02-12 | 2021-09-01 | Nouryon Chemicals International B.V. | Process for preparing higher ethylene amines |
BR112018014270B1 (pt) | 2016-02-12 | 2022-10-11 | Akzo Nobel Chemicals International B.V. | Processo de preparação de etilenoaminas |
EP3555041B1 (en) * | 2016-12-15 | 2022-02-02 | Nouryon Chemicals International B.V. | Process for manufacturing ethylene amines |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5869847A (ja) * | 1981-09-30 | 1983-04-26 | ユニオン カーバイド コーポレーシヨン | ポリアルキレンポリアミンの製造法 |
US4387249A (en) * | 1981-12-18 | 1983-06-07 | The Dow Chemical Company | Process for the manufacture of diethylenetriamine |
US5491263A (en) * | 1993-12-21 | 1996-02-13 | The Dow Chemical Company | Aminoethylation process for production of substituted ethylene diamines |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2613212A (en) * | 1950-10-26 | 1952-10-07 | Rohm & Haas | Imidazolidone derivatives |
US2812333A (en) | 1954-09-27 | 1957-11-05 | Union Carbide Corp | Process for the preparation of 1-(2-hydroxyethyl) imidazolidine-2 |
CH478180A (de) | 1966-11-07 | 1969-09-15 | Francis Dr Pascoe Peter | Verfahren zur Herstellung von Polyäthylenaminen |
GB1510538A (en) | 1974-06-22 | 1978-05-10 | Bayer Ag | Colourless triethylene tetramine and tetraethylene pentamine |
US4123462A (en) | 1976-01-07 | 1978-10-31 | Union Carbide Corporation | Amination process using nickel-rhenium catalysts |
JPS5538329A (en) * | 1978-09-13 | 1980-03-17 | Toyo Soda Mfg Co Ltd | Preparation of polyethylenepolyamine |
US4503250A (en) * | 1981-09-30 | 1985-03-05 | Union Carbide Corporation | Preparation of polyalkylene polyamines |
IT1159074B (it) | 1982-06-24 | 1987-02-25 | Stoppani Luigi Spa | Composto di addizione fra menadione e tiamina a reciproca stabilizzazione |
NL8204546A (nl) | 1982-11-23 | 1984-06-18 | Akzo Nv | Werkwijze voor het winnen van ethyleenamines uit waterige oplossing. |
JPS59161338A (ja) | 1983-03-04 | 1984-09-12 | Toyo Soda Mfg Co Ltd | エチレンアミン類炭酸塩水溶液からエチレンアミン類を得る方法 |
US4684729A (en) | 1983-07-15 | 1987-08-04 | The Dow Chemical Company | Polyethylene polypiperazine compositions |
JPS60120842A (ja) | 1983-12-03 | 1985-06-28 | Toyo Soda Mfg Co Ltd | エチレンアミン類炭酸塩からエチレンアミン類を得る方法 |
JPS60126248A (ja) | 1983-12-09 | 1985-07-05 | Toyo Soda Mfg Co Ltd | エチレンアミン類炭酸塩水溶液の脱炭酸方法 |
EP0222934A1 (en) | 1985-09-11 | 1987-05-27 | The Dow Chemical Company | Process for preparation of polyalkylenepolyamines |
US4758354A (en) | 1985-12-12 | 1988-07-19 | General Technology Applications, Inc. | Separation process |
DE3744120A1 (de) | 1987-12-24 | 1989-07-06 | Basf Ag | Verfahren zur herstellung von 1,3-dialkyl-2-imidazolidinonen |
US5011999A (en) * | 1989-02-23 | 1991-04-30 | The Dow Chemical Company | Process of preparing non-cyclic polyalkylenepolyamines employing group VB metal catalysts |
US5112984A (en) | 1990-09-20 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the preparation of cyclic nitrogen-containing compounds |
US5262534A (en) | 1990-09-20 | 1993-11-16 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the preparation of nonaromatic cyclic nitrogen-containing compounds |
US5399706A (en) * | 1993-03-02 | 1995-03-21 | H. B. Fuller Licensing & Financing, Inc. | Imidazolidinone diamine and derivatives thereof |
US5364971A (en) | 1993-08-25 | 1994-11-15 | Texaco Chemical Inc. | Decolorization of polyethylene polyamines using ruthenium |
JPH1045682A (ja) | 1996-08-05 | 1998-02-17 | Tosoh Corp | 高品位ポリエチレンポリアミン類の製造方法 |
DE10335991A1 (de) | 2003-08-01 | 2005-02-24 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
FR2912148B1 (fr) | 2007-02-07 | 2009-04-10 | Arkema France | Materiau polymere de type styrene / anhydride, greffe ayant des proprietes ameliorees |
CN101675025B (zh) | 2007-03-01 | 2015-04-08 | 巴斯夫欧洲公司 | 制备四亚乙基五胺的方法 |
KR20090122435A (ko) * | 2007-03-01 | 2009-11-30 | 바스프 에스이 | Eddn을 사용하여 teta를 제조하는 신규 방법 |
BRPI0914042A2 (pt) | 2008-10-06 | 2015-11-03 | Union Carbide Chem Plastic | processo para a produção de uma ou mais etilenoaminas por uma reação de transaminação |
BRPI0914016A2 (pt) | 2008-10-06 | 2015-07-28 | Union Carbide Chem Plastic | Método para preparar uma triamina cíclica |
CN102224129B (zh) | 2008-10-06 | 2015-02-11 | 联合碳化化学品及塑料技术公司 | 制备乙撑胺的方法 |
US8459941B2 (en) | 2009-06-15 | 2013-06-11 | General Electric Company | Mechanical joint for a gas turbine engine |
CA2785028C (en) | 2009-12-21 | 2018-01-16 | Schlumberger Canada Limited | Hydrogen bonding material for oilfield application |
FR2955105B1 (fr) * | 2010-01-11 | 2012-04-20 | Arkema France | Procede de preparation d'aminoethyl imidazolidone ou de son thiocarbonyle |
CN101870679A (zh) * | 2010-06-03 | 2010-10-27 | 华东理工大学 | N-(2-氨乙基)-2-咪唑烷酮的制备方法 |
EP2812280A4 (en) | 2012-01-20 | 2016-03-30 | Univ Texas | MIXTURES OF AMINES WITH PIPERAZINE FOR CO2 DETECTION |
CN103333323B (zh) * | 2013-06-13 | 2015-09-02 | 武汉市科达云石护理材料有限公司 | 高韧性高活性环氧树脂固化剂及其制备方法 |
BR112018014270B1 (pt) | 2016-02-12 | 2022-10-11 | Akzo Nobel Chemicals International B.V. | Processo de preparação de etilenoaminas |
WO2017137529A1 (en) | 2016-02-12 | 2017-08-17 | Akzo Nobel Chemicals International B.V. | Process to convert cyclic alkylene ureas into their corresponding alkylene amines |
EP3414222B1 (en) | 2016-02-12 | 2021-09-01 | Nouryon Chemicals International B.V. | Process for preparing higher ethylene amines |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5869847A (ja) * | 1981-09-30 | 1983-04-26 | ユニオン カーバイド コーポレーシヨン | ポリアルキレンポリアミンの製造法 |
US4387249A (en) * | 1981-12-18 | 1983-06-07 | The Dow Chemical Company | Process for the manufacture of diethylenetriamine |
US5491263A (en) * | 1993-12-21 | 1996-02-13 | The Dow Chemical Company | Aminoethylation process for production of substituted ethylene diamines |
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