JP5264489B2 - 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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- JP5264489B2 JP5264489B2 JP2008529589A JP2008529589A JP5264489B2 JP 5264489 B2 JP5264489 B2 JP 5264489B2 JP 2008529589 A JP2008529589 A JP 2008529589A JP 2008529589 A JP2008529589 A JP 2008529589A JP 5264489 B2 JP5264489 B2 JP 5264489B2
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 44
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 73
- 150000001412 amines Chemical class 0.000 claims abstract description 68
- 238000002156 mixing Methods 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 47
- 230000008569 process Effects 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims description 83
- 239000007789 gas Substances 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 239000012071 phase Substances 0.000 description 24
- -1 aliphatic diamines Chemical class 0.000 description 17
- 239000002904 solvent Substances 0.000 description 12
- 238000010791 quenching Methods 0.000 description 11
- 230000000171 quenching effect Effects 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- JMFCAIUTSABFDU-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O JMFCAIUTSABFDU-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-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
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CVGYTOLNWAMTRJ-UHFFFAOYSA-N N=C=O.N=C=O.CCCCC(C)C(C)(C)C Chemical compound N=C=O.N=C=O.CCCCC(C)C(C)(C)C CVGYTOLNWAMTRJ-UHFFFAOYSA-N 0.000 description 1
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 description 1
- SZKGLHFDOIYOSN-UHFFFAOYSA-N N=C=O.NC(Cl)=O Chemical class N=C=O.NC(Cl)=O SZKGLHFDOIYOSN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical class COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical class NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
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Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/30—Injector mixers
- B01F25/31—Injector mixers in conduits or tubes through which the main component flows
- B01F25/313—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit
- B01F25/3132—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit by using two or more injector devices
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/30—Injector mixers
- B01F25/31—Injector mixers in conduits or tubes through which the main component flows
- B01F25/313—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit
- B01F25/3132—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit by using two or more injector devices
- B01F25/31322—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit by using two or more injector devices used simultaneously
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/30—Injector mixers
- B01F25/31—Injector mixers in conduits or tubes through which the main component flows
- B01F25/313—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit
- B01F25/3133—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced in the centre of the conduit characterised by the specific design of the injector
- B01F25/31332—Ring, torus, toroidal or coiled configurations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/40—Static mixers
- B01F25/42—Static mixers in which the mixing is affected by moving the components jointly in changing directions, e.g. in tubes provided with baffles or obstructions
- B01F25/43—Mixing tubes, e.g. wherein the material is moved in a radial or partly reversed direction
- B01F25/433—Mixing tubes wherein the shape of the tube influences the mixing, e.g. mixing tubes with varying cross-section or provided with inwardly extending profiles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/40—Static mixers
- B01F25/42—Static mixers in which the mixing is affected by moving the components jointly in changing directions, e.g. in tubes provided with baffles or obstructions
- B01F25/43—Mixing tubes, e.g. wherein the material is moved in a radial or partly reversed direction
- B01F25/433—Mixing tubes wherein the shape of the tube influences the mixing, e.g. mixing tubes with varying cross-section or provided with inwardly extending profiles
- B01F25/4335—Mixers with a converging-diverging cross-section
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/26—Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(n+1)ホスゲン流及びnアミン流は、一般に、反応器の一端における混合ユニットを通じて反応器内に供給される。アミン流は2個のホスゲン流の間の環状間隙を通じて高速で供給される。全てのホスゲン流及びアミン流は環状間隙を通じて導入される。間に位置し、隣接するホスゲン流及びアミン流が導入される環状間隙は、好ましくは、それらの区域の重心が直線上に位置しているもの、特に好ましくは、それらの領域の重心が1つのポイントと一致するものである。
反応空間は、ホスゲン、アミン、必要であれば不活性媒体と混合された気体状の混合物の混合(一般的に反応の開始により同時に起こる)が主に実施される混合空間を、前部領域に含む。次いで、本質的に、反応、及び多くても副次的な程度の混合のみが、反応空間の後部で実施される。
−第二に、長さL2を有する区域、
−第三に、長さL3を有する区域、それに続き、
−第四に、内部置換体を有しない管型反応器を表わし、急冷に続く、長さL4を有する区域(以下を参照)。
更に、Fは、平均速度が、一般的に250m/秒未満、好ましくは240m/秒未満、特に好ましくは230m/秒未満、非常に好ましくは220m/秒未満、特には210m/秒未満であるように選択される。
Claims (27)
- イソシアネートを製造するにあたり、対応するアミンとホスゲンとを、場合により、少なくとも1種の不活性媒体の存在下で、気相において反応させることによりイソシアネートを製造する方法において、1つの反応器において、nアミン流をn+1ホスゲン流と反応させ、その際、nは少なくとも1の正の整数であり、全てのアミン及びホスゲン流が、それぞれ混合のための環状間隙を介して反応器中に導入される方法。
- イソシアネートが、1,6−ジイソシアナトヘキサン、1−イソシアナト−3,3,5−トリメチル−5−(イソシアナトメチル)シクロヘキサン、4,4’−ジ(イソシアナトシクロヘキシル)メタン及びトルイレンジイソシアネート異性体混合物からなる群から選択される、請求項1記載の方法。
- 窒素、ヘリウム、アルゴン、クロロベンゼン、クロロトルエン、o−ジクロロベンゼン、トルエン、キシレン、クロロナフタレン、デカヒドロナフタレン、二酸化炭素及び一酸化炭素からなる群から選択される少なくとも1種の不活性媒体が存在する、請求項1又は2記載の方法。
- アミン又はホスゲンに対する不活性媒体のガス量が、0.0001超〜30である、請求項3記載の方法。
- 方法における温度が200〜600℃である、請求項1から4までのいずれか1項記載の方法。
- ホスゲンとアミノ基とのモル比が1.1:1〜20:1に設定される、請求項1から5までのいずれか1項記載の方法。
- 外壁で最外部の流れとして、かつ最内部の流れとして、それぞれ1つのホスゲン流が反応器に導入される、請求項1から6までのいずれか1項記載の方法。
- それぞれの外部のホスゲン流の面積と、アミン流の面積と、それぞれの隣接する内部ホスゲン流の面積との比が0.3〜5:1:0.3〜5である、請求項1から7までのいずれか1項記載の方法。
- ホスゲン流の全面積に対するアミン流の全面積の比が0.00002を超え、5未満である、請求項1から8までのいずれか1項記載の方法。
- 個々の出発材料が、混合装置中で20〜400m/秒の流速で反応器中に運搬される、請求項1から9までのいずれか1項記載の方法。
- 前記反応が実施される反応器が、環状間隙空間である、請求項1から10までのいずれか1項記載の方法。
- 前記反応器が、その内部に容積体を有し、環状間隙空間を形成する、請求項10記載の方法。
- 前記容積体が、反応器に沿って、0の直径まで狭まる、請求項11記載の方法。
- 反応器の流通面積が、反応器の通過の間に変化しない、請求項10記載の方法。
- 反応器の流通面積が、反応器の通過の間に第一の区域で拡大し、それに続く第二の区域で一定に維持される、請求項10記載の方法。
- 反応器の流通面積が、反応器の通過の間に第一の区域で一定に維持され、第二の区域で拡大し、第3の区域で一定に維持される、請求項10記載の方法。
- 反応器の流通面積が、反応器の通過の間に第一の区域で一定に維持され、第二の区域で縮小し、第三の区域で拡大し、第四の区域で一定に維持される、請求項10記載の方法。
- 反応器の流通面積が、反応器の通過の間に第一の区域で縮小し、第二の区域で拡大し、第三の区域で一定に維持される、請求項10記載の方法。
- 反応器の流通面積が、反応器の通過の間に第一の区域で縮小し、第二の区域で一定に維持され、第三の区域で拡大し、第四の区域で一定に維持される、請求項10記載の方法。
- 反応混合物の平均接触時間が0.001秒〜5秒未満である、請求項1から19までのいずれか1項記載の方法。
- 前記反応器中の流れが、10を超えるボーデンシュタイン数を有する、請求項1から20までのいずれか1項記載の方法。
- 前記反応混合物の流れが、少なくとも2300のレイノルズ数を有する、請求項1から21までのいずれか1項記載の方法。
- 出発材料の混合が99%の度合いまで起こる空間におけるアミンの変換が15%以下である、請求項1から22までのいずれか1項記載の方法。
- アミン流が、そのつど2個のホスゲン流の間を通じて供給される、請求項1から23までのいずれか1項記載の方法。
- 少なくとも1個の管型反応器を含むイソシアネート製造装置であって、その一端面が、お互いの周辺に環状様式に配置された(アミン流をn、ホスゲン流をn+1)の環状間隙を備え、nは少なくとも1の正の整数であり、そのうち、1つおきの環状間隙は、供給流のための少なくとも1個の供給導管と連結しており、それらの間に位置する環状間隙は、他の供給流のための少なくとも1個の供給導管と連結しており、その際、環状間隙は、端面で反応器の長軸の周囲に同心円状に配置されており、その中央に、管型反応器に突出し反応器の長軸の周囲に配置された容積体が位置し、その際、容積体の外径及び管型反応器の内径が反応空間を取り囲むイソシアネート製造装置。
- アミン流が、そのつど2個のホスゲン流の間を通じて供給される、請求項25記載の装置。
- 気相ホスゲン化における、請求項25又は26記載の装置の使用。
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JP5460327B2 (ja) * | 2006-11-07 | 2014-04-02 | ビーエーエスエフ ソシエタス・ヨーロピア | イソシアネートの製造方法 |
DE102006058633A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
EP2188248A1 (de) * | 2007-08-30 | 2010-05-26 | Basf Se | Verfahren zur herstellung von isocyanaten |
JP2010536911A (ja) | 2007-08-30 | 2010-12-02 | ビーエーエスエフ ソシエタス・ヨーロピア | イソシアネートの製造法 |
DE102007056511A1 (de) | 2007-11-22 | 2009-05-28 | Bayer Materialscience Ag | Verfahren zur Herstellung aromatischer Diisocyanate in der Gasphase |
EP2307356B1 (de) | 2008-07-23 | 2012-06-06 | Basf Se | Verfahren zur herstellung von isocyanaten |
PL2349986T3 (pl) | 2008-10-15 | 2013-09-30 | Basf Se | Sposób wytwarzania izocyjanianów |
JP5771528B2 (ja) | 2008-11-07 | 2015-09-02 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | イソシアネートの製造方法 |
WO2010063665A1 (de) | 2008-12-03 | 2010-06-10 | Basf Se | Verfahren zur herstellung von isocyanaten |
DE102008061686A1 (de) | 2008-12-11 | 2010-06-17 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
DE102008063991A1 (de) | 2008-12-19 | 2010-06-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
JP5771535B2 (ja) | 2009-03-06 | 2015-09-02 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | イソシアネートの製造方法および製造装置 |
US8759568B2 (en) | 2009-04-08 | 2014-06-24 | Basf Se | Process for preparing isocyanates |
DE102009032414A1 (de) * | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
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US9321720B2 (en) * | 2010-10-14 | 2016-04-26 | Basf Se | Process for preparing isocyanates |
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WO2016042125A1 (de) | 2014-09-19 | 2016-03-24 | Covestro Deutschland Ag | Verfahren zur herstellung von 1,5-pentandiisocyanat in der gasphase |
EP3271432B1 (de) | 2015-03-16 | 2019-07-31 | Covestro Deutschland AG | Polyisocyanatzusammensetzung auf basis von 1,5-pentamethylendiisocyanat |
US10428174B2 (en) | 2015-04-21 | 2019-10-01 | Covestro Deutschland Ag | Polyisocyanate mixture based on 1,5-diisocyanatopentane |
KR20180018533A (ko) | 2015-06-12 | 2018-02-21 | 코베스트로 도이칠란트 아게 | 디이소시아네이트의 기체 상 제조 방법 |
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