JP2009196991A - イソシアネートの製造方法 - Google Patents
イソシアネートの製造方法 Download PDFInfo
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- JP2009196991A JP2009196991A JP2009029230A JP2009029230A JP2009196991A JP 2009196991 A JP2009196991 A JP 2009196991A JP 2009029230 A JP2009029230 A JP 2009029230A JP 2009029230 A JP2009029230 A JP 2009029230A JP 2009196991 A JP2009196991 A JP 2009196991A
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- phosgene
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- hydrogen chloride
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 53
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title abstract description 35
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 333
- 239000002904 solvent Substances 0.000 claims abstract description 201
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 178
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 167
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 164
- 238000000034 method Methods 0.000 claims abstract description 100
- 239000007789 gas Substances 0.000 claims abstract description 63
- 150000001412 amines Chemical class 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 239000007788 liquid Substances 0.000 claims abstract description 47
- 239000007791 liquid phase Substances 0.000 claims abstract description 24
- 238000009833 condensation Methods 0.000 claims description 79
- 230000005494 condensation Effects 0.000 claims description 73
- 230000036961 partial effect Effects 0.000 claims description 63
- 230000008569 process Effects 0.000 claims description 53
- 238000011084 recovery Methods 0.000 claims description 52
- 239000012071 phase Substances 0.000 claims description 45
- 239000006096 absorbing agent Substances 0.000 claims description 41
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 abstract description 14
- 230000000717 retained effect Effects 0.000 abstract description 3
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- 238000010521 absorption reaction Methods 0.000 description 116
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 62
- 238000000926 separation method Methods 0.000 description 27
- 239000007859 condensation product Substances 0.000 description 24
- 238000012856 packing Methods 0.000 description 23
- 239000012267 brine Substances 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 239000002250 absorbent Substances 0.000 description 16
- 230000002745 absorbent Effects 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 238000004821 distillation Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- -1 and in some cases Chemical compound 0.000 description 9
- 238000010586 diagram Methods 0.000 description 9
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- 238000005406 washing Methods 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000005868 electrolysis reaction Methods 0.000 description 7
- 238000011144 upstream manufacturing Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000011261 inert gas Substances 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002912 waste gas Substances 0.000 description 4
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000006056 electrooxidation reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- DNMWKVLCHRNMFF-UHFFFAOYSA-N 1,5,5-trimethylcyclohexane-1,3-diamine Chemical compound CC1(C)CC(N)CC(C)(N)C1 DNMWKVLCHRNMFF-UHFFFAOYSA-N 0.000 description 1
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- 150000004999 2,4-diaminotoluenes Chemical class 0.000 description 1
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
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- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 235000006545 Ziziphus mauritiana Nutrition 0.000 description 1
- 240000000038 Ziziphus mauritiana Species 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CZEPJJXZASVXQF-ZETCQYMHSA-N ethyl (2s)-2,6-diaminohexanoate Chemical compound CCOC(=O)[C@@H](N)CCCCN CZEPJJXZASVXQF-ZETCQYMHSA-N 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- DQWFTGPZPKZMAB-UHFFFAOYSA-N undecane-1,6,11-triamine Chemical compound NCCCCCC(N)CCCCCN DQWFTGPZPKZMAB-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/03—Preparation from chlorides
- C01B7/035—Preparation of hydrogen chloride from chlorides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01B—MEASURING LENGTH, THICKNESS OR SIMILAR LINEAR DIMENSIONS; MEASURING ANGLES; MEASURING AREAS; MEASURING IRREGULARITIES OF SURFACES OR CONTOURS
- G01B11/00—Measuring arrangements characterised by the use of optical techniques
- G01B11/02—Measuring arrangements characterised by the use of optical techniques for measuring length, width or thickness
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】適当なアミンをホスゲンと反応させ、それによって得られたガス混合物を凝縮させ、それによって得られた液相をストリッピングし、こうして液体の形で保持された溶剤を、アミンとホスゲンとの反応に戻す。
【効果】選択可能な方法の場合には、循環路中での溶剤の全体量は、同じままであり、塩化水素を精製するための溶剤の量は、適当に選択されたその後の処理がこうして必要とされる場合には、さらに増加させることができる。
【選択図】なし
Description
a)少なくとも1つのアミンをホスゲンと溶剤の存在下に反応させ、こうして相応するイソシアネートおよび場合によっては溶剤を含有する液状の流れ、ならびに塩化水素、ホスゲン、溶剤、および低沸点物および不活性物質を含有するガス状の流れを形成させ、
b)塩化水素、ホスゲン、溶剤、ならびに低沸点物および不活性物質を含有するガス状の流れを部分凝縮によって分離し、こうして液相とガス相を形成させ、実質的に溶剤、ホスゲンおよび塩化水素から構成されている液相を回収塔の塔頂部に案内し、実質的に塩化水素、ホスゲン、ガス状の流れの質量に対して30質量%以下、有利に10質量%以下の濃度の溶剤、ならびに低沸点物および不活性物質を含有するガス状の流れを回収塔の塔頂部に案内し;
c)実質的に溶剤、ホスゲンおよび塩化水素から構成されている、工程b)で回収塔中に導入された液相を、溶剤相とガス相とに分離し、この場合この溶剤相は、液体の形で回収塔の底部から除去され、および底部の液体流の質量に対して0.1質量%未満、有利に0.01質量%未満、特に有利に0.001質量%未満のホスゲン濃度を有し、ガス相は、前記塔の塔頂部から除去され、およびホスゲン、塩化水素、低沸点物および不活性物質、ならびに気相の質量に対して30質量%未満、有利に10質量%未満、特に有利に5質量%未満の濃度の溶剤を含有し;
d)工程c)で形成された溶剤相を工程a)でのホスゲン化反応に返送し;
e)工程c)で形成されたガス相を吸収装置中に導入し、この吸収装置中でガス相中に含有されたホスゲンを、工程a)でのホスゲン化反応に使用された溶剤と同じ溶剤中に吸収し、それによってホスゲン溶液の質量に対して20〜80質量%、有利に50〜80質量%のホスゲン濃度を有するホスゲン溶液を形成させ;
f)場合によっては工程e)で得られたホスゲン溶液を付加的なホスゲンと混合し、濃縮されたホスゲン溶液を形成させ;
および
g)工程e)で形成されたホスゲン溶液または工程f)で形成された濃縮されたホスゲン溶液を工程a)でのホスゲン化反応に返送する。
h)工程b)、e)およびe)で形成されたガス状の蒸気を合わせ、塩化水素流の質量に対して0.5質量%以下、有利に0.2質量%以下、特に有利に0.1質量%以下の濃度のホスゲンを含有する塩化水素流を形成させる。
a)イソシアネートの製造およびそれによって実施される、塩化水素、ホスゲン、溶剤、および低沸点物および不活性物質を含有する流れの分離を、本発明による方法によって実施し、この場合この流れは、脂肪族アミンまたは芳香族アミンとホスゲンとの反応で形成され、公知技術水準に相応する反応段階で相応するイソシアネートを生じる。そのために、この分離を二段階の部分凝縮によって実施し、この場合この部分凝縮の第1段階からの凝縮生成物は、供給原料として回収塔の塔頂部から導入され、回収塔の塔底生成物は、新しい溶剤タンクにフィードバックされ、回収塔の塔頂部の蒸気は、部分凝縮の第1段落に再び返送され、第1の部分凝縮からの蒸気の全部は、第2の部分凝縮に供給され、その後にホスゲンとクロロベンゼンとは向流で部分的に等温吸収され、引続き残りのホスゲンとクロロベンゼンとは向流で断熱吸収され、最終的に低ホスゲン型塩化水素流(low-phosgene hydrogen chloride stream)および低溶剤型塩化水素流(low-solvent hydrogen chloride stream)からの残りのクロロベンゼンは、後凝縮される。このような方法は、上記したように図2に関する。
Claims (8)
- 次の工程:
a)少なくとも1つのアミンをホスゲンと溶剤の存在下に反応させ、こうして相応するイソシアネートおよび場合によっては溶剤を含有する液状の流れ、ならびに塩化水素、ホスゲン、溶剤、および低沸点物および不活性物質を含有するガス状の流れを形成させ、
b)塩化水素、ホスゲン、溶剤、ならびに低沸点物および不活性物質を含有するガス状の流れを部分凝縮によって分離し、こうして液相とガス相を形成させ、この場合回収塔の塔頂部に案内される液相は、実質的に溶剤、ホスゲンおよび塩化水素から構成されており、ガス状の流れは、実質的に塩化水素、ホスゲン、低沸点物および不活性物質、ならびにガス状の流れの質量に対して30質量%以下の溶剤を含有し;
c)実質的に溶剤、ホスゲンおよび塩化水素から構成されている、工程b)で回収塔中に導入された液相を、溶剤相とガス相とに分離し、この場合この溶剤相は、液体の形で回収塔の底部から除去され、および底部の液体流の質量に対して0.1質量%未満のホスゲン濃度を有し、ガス相は、前記塔の塔頂部から除去され、およびホスゲン、塩化水素、低沸点物および不活性物質、ならびに気相の質量に対して30質量%未満の溶剤を含有し;
d)工程c)で形成された溶剤相を工程a)でのホスゲン化反応に返送し;
e)工程c)で形成されたガス相を吸収装置中に導入し、この吸収装置中でガス相中に含有されたホスゲンを、工程a)でのホスゲン化反応に使用された溶剤と同じ溶剤中に吸収し、それによってホスゲン溶液の質量に対して20〜80質量%のホスゲン濃度を有するホスゲン溶液を形成させ;
f)場合によっては工程e)で得られたホスゲン溶液を付加的なホスゲンと混合し、濃縮されたホスゲン溶液を形成させ;
g)工程e)で形成されたホスゲン溶液または工程f)で形成された濃縮されたホスゲン溶液を工程a)でのホスゲン化反応に返送することを有することを特徴とする、イソシアネートの製造法。 - 工程e)でガス相を1回または数回部分凝縮し、その後にガス相を吸収部に導入する、請求項1記載の方法。
- 付加的に、
h)工程b)、c)およびe)で形成されたガス状の蒸気を合わせ、塩化水素流の質量に対して0.5質量%以下の濃度のホスゲンを含有する塩化水素流を形成させる、請求項1記載の方法。 - 生じる塩化水素流は、塩化水素流の質量に対して0.2質量%以下の濃度のホスゲンを含有する、請求項3記載の方法。
- 生じる塩化水素流は、塩化水素流の質量に対して0.1質量%以下の濃度のホスゲンを含有する、請求項3記載の方法。
- a)ホスゲン化反応を液相中で実施する、請求項1記載の方法。
- 少なくとも一部分のアミンを最初に工程d)に返送される溶剤相と混合し、次に生じるアミン溶液を工程a)でホスゲン化反応に導入する、請求項6記載の方法。
- 少なくとも一部分のホスゲンを最初に工程d)に返送される溶剤相と混合し、次に生じるホスゲン溶液を工程a)でホスゲン化反応に導入する、請求項6記載の方法。
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BRPI0900468A2 (pt) | 2009-10-06 |
CN101514172B (zh) | 2014-12-17 |
US7645900B2 (en) | 2010-01-12 |
DE102008009761A1 (de) | 2009-08-27 |
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