JP5599130B2 - トルエンジイソシアネートの製造方法 - Google Patents
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- JP5599130B2 JP5599130B2 JP2007150682A JP2007150682A JP5599130B2 JP 5599130 B2 JP5599130 B2 JP 5599130B2 JP 2007150682 A JP2007150682 A JP 2007150682A JP 2007150682 A JP2007150682 A JP 2007150682A JP 5599130 B2 JP5599130 B2 JP 5599130B2
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- Prior art keywords
- toluenediamine
- tda
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims abstract description 75
- 150000003997 cyclic ketones Chemical class 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000000746 purification Methods 0.000 claims abstract description 9
- 238000004821 distillation Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 238000000926 separation method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 5
- JLSSJCNIHJCNNL-UHFFFAOYSA-N 2-(aminomethyl)cyclohex-2-en-1-one Chemical class NCC1=CCCCC1=O JLSSJCNIHJCNNL-UHFFFAOYSA-N 0.000 claims description 4
- XGJTVHAGMWPDKV-UHFFFAOYSA-N 2-(aminomethyl)cyclohexan-1-one Chemical class NCC1CCCCC1=O XGJTVHAGMWPDKV-UHFFFAOYSA-N 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- ZMBQZWCDYKGVLW-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-diamine Chemical compound CC1(N)C=CC=CC1N ZMBQZWCDYKGVLW-UHFFFAOYSA-N 0.000 claims 1
- PZKPUGIOJKNRQZ-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,3-diamine Chemical compound CC1(N)CC(N)=CC=C1 PZKPUGIOJKNRQZ-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 22
- 239000000047 product Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 8
- 238000005192 partition Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 238000005698 Diels-Alder reaction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical class CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-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
- FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000003419 tautomerization reaction Methods 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
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- LKTNAAYQZJAXCJ-UHFFFAOYSA-N 2-methylcyclohex-2-en-1-one Chemical class CC1=CCCCC1=O LKTNAAYQZJAXCJ-UHFFFAOYSA-N 0.000 description 1
- CZSSKBQAJULWPY-UHFFFAOYSA-N 2-undecylsulfanylacetic acid Chemical compound CCCCCCCCCCCSCC(O)=O CZSSKBQAJULWPY-UHFFFAOYSA-N 0.000 description 1
- IITQJMYAYSNIMI-UHFFFAOYSA-N 3-Methyl-2-cyclohexen-1-one Chemical compound CC1=CC(=O)CCC1 IITQJMYAYSNIMI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- -1 diphenylmethane series isocyanates Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N n-(2-methylphenyl)nitramide Chemical compound CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000004998 toluenediamines Chemical class 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
a)ジニトロトルエンを触媒の存在下で水素化して、粗製トルエンジアミン混合物を得ること、
b)該粗製トルエンジアミン混合物を精製して、トルエンジアミンの100質量%に対して0.1質量%未満の全量の環状ケトンを含有するトルエンジアミンを得ること、及び
c)b)で形成された、トルエンジアミンの100質量%に対して0.1質量%未満の全量の環状ケトンを含有するトルエンジアミンをホスゲン化して、トルエンジイソシアネートを得ること
を含む。
第1表に示される環状ケトンの量を含有するトルエンジアミン(TDA)5.4t/hを、工業的なTDI製造方法でホスゲン化した。ホスゲン化は、多孔板塔中で70〜125℃の温度で実施した。純粋なTDIは、溶剤を分離除去し、粗製TDIを140〜160℃の温度で段階的に蒸留することによって得られた。最終蒸留工程は、充填隔壁塔中で実施し、その中で高沸点物を濃縮し、それを底部で分離除去し、そして入口流(inlet stream)中に含まれる低沸点物の大部分を濃縮し、それを頂部で分離除去した。高沸点物を、後続の蒸発による濃縮によってプロセスから排出した;該低沸点物は溶剤回路中に返送した。
フラクションA:撹拌槽中で25バールの圧力でジニトロトルエンを水素化することによって製造された。使用される触媒はニッケル触媒であった。TDA反応の下流にある蒸留による分離シーケンスにおいて、水、低沸点物及びo−TDAを粗生成物から分離した。
第2表に示される環状ケトンの量を含有するトルエンジアミン(TDA)10.5t/hを、工業的なTDI製造方法でホスゲン化した。ホスゲン化は、多孔板塔中で70〜125℃の温度で実施した。純粋なTDIは、溶剤を分離除去し、粗製TDIを140〜180℃の温度で段階的に蒸留することによって得られた。最終蒸留工程は、充填塔中で実施し、その中で高沸点物を濃縮し、それを底部で分離除去し、そして入口流中に含まれる低沸点物の幾らかを濃縮し、それを頂部で分離除去した。高沸点物を、後続の蒸発による濃縮によってプロセスから排出した;頂部で分離除去された低沸点物を溶剤回路中に返送した。
Claims (4)
- トルエンジイソシアネートの製造方法において:
a)ジニトロトルエンを触媒の存在下で水素化して、粗製トルエンジアミン混合物を得ること、
b)該粗製トルエンジアミン混合物を精製して、トルエンジアミンの100質量%に対して0.1質量%未満の全量の、アミノメチルシクロヘキサノン類及びアミノメチルシクロへキセノン類からなる群から選択される環状ケトンを含有するトルエンジアミンを得ること、及び
c)トルエンジアミンの100質量%に対して0.1質量%未満の全量の環状ケトンを含有するトルエンジアミンをホスゲン化して、トルエンジイソシアネートを得ること
を含み、
工程a)が120〜180℃の温度、20〜40バールの水素圧、及び0.5〜4時間の滞留時間で実施され、かつ、触媒が、ドープされた若しくはドープされていないラネーニッケル触媒、ドープされた若しくはドープされていない、担持体に固定されたニッケル触媒、および担持体に固定されかつ1若しくはそれより多くの貴金属で負荷された貴金属触媒からなる群から選択され、および
工程b)が、反応水、低沸点物、オルト−トルエンジアミン及び場合により溶剤を、まず粗製トルエンジアミン混合物から部分的に若しくは完全に分離し、次いで高沸点物及び環状ケトンを、部分的に若しくは完全に、蒸留器、凝縮器及び少なくとも3つの理論段を有するストリッピング帯域を有する蒸留塔を用いてメタ−トルエンジアミンから分離し、その際、その分離は、50〜2000ミリバールの頂部絶対圧、140〜320℃の頂部温度、及び底部温度260℃未満で実施される、前記製造方法。 - 前記精製工程b)が、高沸点物が分離される工程を有する多工程蒸留において実施される、請求項1記載の製造方法。
- 工程a)で形成されるトルエンジアミン混合物中の環状ケトンの全含量が、工程b)において25%より多い量だけ減少される、請求項1又は2に記載の製造方法。
- 工程a)が、付加的な溶剤を使用して、又は使用せずに液相で実施される、請求項1〜3いずれか1項に記載の製造方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/448,265 US8030522B2 (en) | 2006-06-07 | 2006-06-07 | Process for the production of toluene diisocyanate |
US11/448265 | 2006-06-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007326857A JP2007326857A (ja) | 2007-12-20 |
JP5599130B2 true JP5599130B2 (ja) | 2014-10-01 |
Family
ID=38335704
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007150682A Expired - Fee Related JP5599130B2 (ja) | 2006-06-07 | 2007-06-06 | トルエンジイソシアネートの製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US8030522B2 (ja) |
EP (1) | EP1864969B1 (ja) |
JP (1) | JP5599130B2 (ja) |
KR (1) | KR101443907B1 (ja) |
CN (1) | CN101085750B (ja) |
AT (1) | ATE520652T1 (ja) |
ES (1) | ES2369572T3 (ja) |
PL (1) | PL1864969T3 (ja) |
PT (1) | PT1864969E (ja) |
TW (1) | TW200806613A (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2060560B1 (en) * | 2007-11-14 | 2016-04-13 | Covestro Deutschland AG | Preparation of light-colored isocyanates |
DE102007056511A1 (de) * | 2007-11-22 | 2009-05-28 | Bayer Materialscience Ag | Verfahren zur Herstellung aromatischer Diisocyanate in der Gasphase |
CN101774948B (zh) * | 2010-03-01 | 2012-10-17 | 甘肃银达化工有限公司 | 连续制备甲苯二异氰酸酯的方法 |
EP2872481B1 (de) | 2012-07-11 | 2016-08-24 | Covestro Deutschland AG | Verfahren zur aufarbeitung von destillationsrückständen aus der isocyanatherstellung |
HUE040552T2 (hu) | 2013-03-12 | 2019-03-28 | Covestro Deutschland Ag | Eljárás rendkívül tiszta TDI-trimerizátumok elõállítására |
WO2014139873A1 (de) | 2013-03-12 | 2014-09-18 | Bayer Materialscience Ag | Verfahren zur herstellung von farbhellen tdi-polyisocyanaten |
EP2915802A1 (de) | 2014-03-03 | 2015-09-09 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyarylaminanlagerungsprodukten, Polyarylanlagerungsprodukte und ihre Verwendung |
KR102039089B1 (ko) | 2016-12-15 | 2019-11-26 | 한화케미칼 주식회사 | 톨루엔디이소시아네이트 정제 방법 |
CN108623463A (zh) * | 2018-06-06 | 2018-10-09 | 福建省东南电化股份有限公司 | 一种甲苯二异氰酸酯生产甲苯硝化工序二返一管优化改进系统 |
CN110105248B (zh) * | 2019-05-31 | 2021-07-20 | 上海应用技术大学 | 一种甲苯二异氰酸酯的制备方法 |
WO2023241927A1 (en) | 2022-06-14 | 2023-12-21 | Basf Se | Process for recovering raw materials from a polyurethane material |
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DE1260092B (de) | 1963-12-23 | 1968-02-01 | Dr Med Ludwig Zwehl | Sitz- und Liegemoebel |
DE3607665A1 (de) * | 1986-03-08 | 1987-09-10 | Bayer Ag | Verfahren zur aufarbeitung waessriger aminloesungen |
DE4142769A1 (de) * | 1991-12-23 | 1993-06-24 | Bayer Hispania Ind S A | Verfahren zur herstellung von isocyanaten und aufarbeitung des rueckstandes |
DE4230098C1 (ja) * | 1992-09-09 | 1993-06-03 | Bayer Ag, 5090 Leverkusen, De | |
DE19528781A1 (de) * | 1995-08-04 | 1997-02-06 | Bayer Ag | Verfahren zur Herstellung von Toluylendiisocyanat, spezielle Gemische aus Toluylendiamin und Wasser und deren Verwendung zur Herstellung von Toluylendiisocyanat |
EP0816333A1 (de) | 1996-06-26 | 1998-01-07 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Lösungen eines oder mehrerer Isocynate, die keine nennenswerten Mengen an farbgebenden Komponenten aufweisen, sowie die Verwendung der so erhaltenen Isocyanate |
DE19711447A1 (de) | 1997-03-19 | 1998-09-24 | Basf Ag | Verfahren zur Herstellung von Isocyanaten mit heller Farbe |
EP1137623B1 (de) * | 1998-12-12 | 2003-06-04 | Basf Aktiengesellschaft | Verfahren zur herstellung von aminen |
DE19909168A1 (de) * | 1999-03-03 | 2000-09-07 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19928741A1 (de) | 1999-06-23 | 2000-12-28 | Basf Ag | Helle Isocyanate, Verfahren zu deren Herstellung und deren Verwendung |
IT1318602B1 (it) * | 2000-06-29 | 2003-08-27 | Enichem Spa | Procedimento per la produzione di ammine aromatiche. |
CN1194962C (zh) * | 2000-12-29 | 2005-03-30 | K·S·T·公司 | 连续制备甲苯二异氰酸酯的方法及其装置 |
DE10129233A1 (de) * | 2001-06-19 | 2003-01-02 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
DE10222968A1 (de) * | 2002-05-23 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
EP1371633A1 (en) * | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
EP1371634A1 (en) * | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate |
EP1413571B1 (en) * | 2002-10-22 | 2006-08-23 | Bayer MaterialScience AG | Process for the purification of toluenediisocyanate incorporating a dividing-wall distillation column for the final purification |
DE10260093A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
DE102004001456A1 (de) * | 2004-01-08 | 2005-08-11 | Basf Ag | Verfahren zur destillativen Aufbereitung von Toluylendiamin |
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CN101085750A (zh) | 2007-12-12 |
EP1864969A1 (en) | 2007-12-12 |
US20070287857A1 (en) | 2007-12-13 |
EP1864969B1 (en) | 2011-08-17 |
ATE520652T1 (de) | 2011-09-15 |
KR101443907B1 (ko) | 2014-09-23 |
ES2369572T3 (es) | 2011-12-02 |
CN101085750B (zh) | 2013-06-19 |
JP2007326857A (ja) | 2007-12-20 |
TW200806613A (en) | 2008-02-01 |
US8030522B2 (en) | 2011-10-04 |
PT1864969E (pt) | 2011-10-17 |
PL1864969T3 (pl) | 2012-01-31 |
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