CA2320477A1 - Method for the production of methylenedi(phenylamine) and methylenedi(phenyl isocyanate) - Google Patents
Method for the production of methylenedi(phenylamine) and methylenedi(phenyl isocyanate) Download PDFInfo
- Publication number
- CA2320477A1 CA2320477A1 CA002320477A CA2320477A CA2320477A1 CA 2320477 A1 CA2320477 A1 CA 2320477A1 CA 002320477 A CA002320477 A CA 002320477A CA 2320477 A CA2320477 A CA 2320477A CA 2320477 A1 CA2320477 A1 CA 2320477A1
- Authority
- CA
- Canada
- Prior art keywords
- formaldehyde
- aniline
- reaction mixture
- mdi
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 title abstract 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 224
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 117
- 239000011541 reaction mixture Substances 0.000 claims abstract description 73
- 239000003377 acid catalyst Substances 0.000 claims abstract description 43
- 238000002156 mixing Methods 0.000 claims abstract description 29
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 14
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 14
- 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 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 33
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 7
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 238000005191 phase separation Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- 210000000056 organ Anatomy 0.000 abstract 1
- 238000005496 tempering Methods 0.000 abstract 1
- 229960004279 formaldehyde Drugs 0.000 description 48
- 235000019256 formaldehyde Nutrition 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- -1 poly(oxymethylene) Polymers 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000008098 formaldehyde solution Substances 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 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
- CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- CIICLJLSRUHUBY-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxy]phenol Chemical compound CC(C)(C)OC1=CC=C(O)C=C1 CIICLJLSRUHUBY-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical class NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 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 1
- 238000009826 distribution Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000007620 mathematical function Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001256 stainless steel alloy Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- 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
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)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19804915.3 | 1998-02-07 | ||
| DE19804915A DE19804915A1 (de) | 1998-02-07 | 1998-02-07 | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| PCT/EP1999/000472 WO1999040059A1 (de) | 1998-02-07 | 1999-01-26 | Verfahren zur herstellung von methylendi(phenylamin) und methylendi (phenylisocyanat) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2320477A1 true CA2320477A1 (en) | 1999-08-12 |
Family
ID=7856961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320477A Abandoned CA2320477A1 (en) | 1998-02-07 | 1999-01-26 | Method for the production of methylenedi(phenylamine) and methylenedi(phenyl isocyanate) |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US6433219B1 (enExample) |
| EP (2) | EP1053222B1 (enExample) |
| JP (2) | JP4731684B2 (enExample) |
| KR (1) | KR100555814B1 (enExample) |
| CN (2) | CN1151119C (enExample) |
| AU (1) | AU2621799A (enExample) |
| BR (1) | BR9907634A (enExample) |
| CA (1) | CA2320477A1 (enExample) |
| DE (3) | DE19804915A1 (enExample) |
| ES (2) | ES2234969T3 (enExample) |
| MX (1) | MXPA00007646A (enExample) |
| PT (2) | PT1270544E (enExample) |
| WO (1) | WO1999040059A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6720455B2 (en) | 2001-08-24 | 2004-04-13 | Bayer Aktiengesellschaft | Process for the production of polyisocyanates of the diphenylmethane series with a reduced color value |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19804915A1 (de) * | 1998-02-07 | 1999-08-12 | Basf Ag | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| DE10031540A1 (de) * | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Herstellung eines aromatischen Polyamingemisches |
| DE10111337A1 (de) * | 2001-03-08 | 2002-09-12 | Basf Ag | Verfahren zur Herstellung von MDI, insbesondere von 2.4'-MDI |
| DE10211021A1 (de) | 2002-03-13 | 2003-09-25 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10222968A1 (de) * | 2002-05-23 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE10238995A1 (de) * | 2002-08-20 | 2004-02-26 | Basf Ag | Gasphasenphosgenierung bei moderaten Drücken |
| DE10260093A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
| DE10260082A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
| DE10331772A1 (de) * | 2003-07-11 | 2005-02-03 | Basf Ag | Verfahren zur Herstellung von Diaminodiarylmethanen |
| DE10333929A1 (de) * | 2003-07-25 | 2005-02-24 | Bayer Materialscience Ag | Herstellung von Mischungen von Di- und Polyisocyanaten der Diphenylmethanreihe mit hohen Gehalten an 4,4'-Methylendiphenyldiisocyanat und 2,4'-Methylendiphenyldiisocyanat |
| DE10347438A1 (de) * | 2003-10-13 | 2005-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102004005319A1 (de) * | 2004-02-04 | 2005-08-25 | Bayer Materialscience Ag | Verfahren zur Herstellung von hochreinem 2,4'-Methylendiphenyldiisocyanat |
| DE102004032416A1 (de) * | 2004-07-05 | 2006-02-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyaminen der Diphenylmethanreihe bei niedriger Protonierung |
| DE102004052370A1 (de) * | 2004-10-28 | 2006-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102005014244A1 (de) * | 2005-03-30 | 2006-10-05 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102005014846A1 (de) * | 2005-03-30 | 2006-10-05 | Basf Ag | MDI Herstellung mittels Flüssigphasen- und Gasphasenphosgenierung |
| JP2012233004A (ja) * | 2005-04-04 | 2012-11-29 | Mitsui Chemicals Inc | ポリイソシアネート製造設備およびポリイソシアネート製造方法 |
| JP2006312619A (ja) * | 2005-04-04 | 2006-11-16 | Mitsui Chemicals Polyurethanes Inc | ポリイソシアネート製造設備およびポリイソシアネート製造方法 |
| JP4739798B2 (ja) * | 2005-04-05 | 2011-08-03 | 三井化学株式会社 | ポリイソシアネート連続製造装置 |
| JP4938007B2 (ja) * | 2005-05-30 | 2012-05-23 | ハンツマン・インターナショナル・エルエルシー | ジフェニルメタン系ポリイソシアネートの製造法 |
| DE102005055189A1 (de) * | 2005-11-19 | 2007-05-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von 4,4'-Diphenylmethandiisocyanat |
| WO2007065767A1 (en) * | 2005-12-08 | 2007-06-14 | Huntsman International Llc | Process for preparing diaminodiphenylmethanes |
| DE102006004047A1 (de) * | 2006-01-28 | 2007-08-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102006004041A1 (de) * | 2006-01-28 | 2007-08-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| CN101528678B (zh) | 2006-10-26 | 2014-03-19 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| WO2008055898A1 (de) * | 2006-11-07 | 2008-05-15 | Basf Se | Verfahren zur herstellung von isocyanaten |
| KR101544219B1 (ko) * | 2007-01-08 | 2015-08-12 | 바스프 에스이 | 디페닐메탄디아민의 제조 방법 |
| KR100888733B1 (ko) | 2007-03-28 | 2009-03-17 | 금호미쓰이화학 주식회사 | 폴리메틸렌 폴리페닐 폴리아민의 제조방법 |
| CN101279923B (zh) * | 2007-04-06 | 2010-08-25 | 宁波万华聚氨酯有限公司 | 一种制备多亚甲基多苯基多胺的方法 |
| EP2014641A3 (en) * | 2007-06-06 | 2009-03-18 | Huntsman International Llc | Process for preparing mixtures of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates |
| KR101538180B1 (ko) | 2007-06-12 | 2015-07-22 | 바스프 에스이 | 염 용액으로부터 무기산을 회수하는 방법 |
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| JP3037065B2 (ja) * | 1994-05-26 | 2000-04-24 | 三井化学株式会社 | メチレン架橋ポリフェニレンポリイソシアネートの製造方法 |
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-
1998
- 1998-02-07 DE DE19804915A patent/DE19804915A1/de not_active Withdrawn
-
1999
- 1999-01-26 PT PT02022029T patent/PT1270544E/pt unknown
- 1999-01-26 KR KR1020007008609A patent/KR100555814B1/ko not_active Expired - Lifetime
- 1999-01-26 JP JP2000530491A patent/JP4731684B2/ja not_active Expired - Fee Related
- 1999-01-26 CA CA002320477A patent/CA2320477A1/en not_active Abandoned
- 1999-01-26 CN CNB998027669A patent/CN1151119C/zh not_active Expired - Lifetime
- 1999-01-26 US US09/601,097 patent/US6433219B1/en not_active Expired - Lifetime
- 1999-01-26 EP EP99906202A patent/EP1053222B1/de not_active Expired - Lifetime
- 1999-01-26 PT PT99906202T patent/PT1053222E/pt unknown
- 1999-01-26 BR BR9907634-9A patent/BR9907634A/pt not_active Application Discontinuation
- 1999-01-26 AU AU26217/99A patent/AU2621799A/en not_active Abandoned
- 1999-01-26 ES ES02022029T patent/ES2234969T3/es not_active Expired - Lifetime
- 1999-01-26 ES ES99906202T patent/ES2198894T3/es not_active Expired - Lifetime
- 1999-01-26 DE DE59905323T patent/DE59905323D1/de not_active Expired - Lifetime
- 1999-01-26 EP EP02022029A patent/EP1270544B1/de not_active Expired - Lifetime
- 1999-01-26 DE DE59911344T patent/DE59911344D1/de not_active Expired - Lifetime
- 1999-01-26 WO PCT/EP1999/000472 patent/WO1999040059A1/de not_active Ceased
- 1999-01-26 CN CNB2004100317075A patent/CN1266124C/zh not_active Expired - Lifetime
-
2000
- 2000-08-04 MX MXPA00007646 patent/MXPA00007646A/es unknown
-
2002
- 2002-05-21 US US10/152,489 patent/US6831192B2/en not_active Expired - Lifetime
-
2004
- 2004-05-11 US US10/843,046 patent/US7230130B2/en not_active Expired - Lifetime
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2010
- 2010-08-04 JP JP2010175044A patent/JP5449082B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6720455B2 (en) | 2001-08-24 | 2004-04-13 | Bayer Aktiengesellschaft | Process for the production of polyisocyanates of the diphenylmethane series with a reduced color value |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1266124C (zh) | 2006-07-26 |
| US20020132953A1 (en) | 2002-09-19 |
| US20050014975A1 (en) | 2005-01-20 |
| DE59911344D1 (de) | 2005-01-27 |
| EP1053222B1 (de) | 2003-05-02 |
| JP2010270147A (ja) | 2010-12-02 |
| CN1290245A (zh) | 2001-04-04 |
| CN1151119C (zh) | 2004-05-26 |
| ES2198894T3 (es) | 2004-02-01 |
| ES2234969T3 (es) | 2005-07-01 |
| EP1053222A1 (de) | 2000-11-22 |
| DE19804915A1 (de) | 1999-08-12 |
| KR20010040725A (ko) | 2001-05-15 |
| EP1270544B1 (de) | 2004-12-22 |
| CN1532189A (zh) | 2004-09-29 |
| KR100555814B1 (ko) | 2006-03-03 |
| MXPA00007646A (es) | 2001-04-01 |
| AU2621799A (en) | 1999-08-23 |
| JP2002502838A (ja) | 2002-01-29 |
| PT1053222E (pt) | 2003-09-30 |
| DE59905323D1 (de) | 2003-06-05 |
| US7230130B2 (en) | 2007-06-12 |
| EP1270544A1 (de) | 2003-01-02 |
| BR9907634A (pt) | 2000-11-14 |
| PT1270544E (pt) | 2005-05-31 |
| US6433219B1 (en) | 2002-08-13 |
| WO1999040059A1 (de) | 1999-08-12 |
| JP4731684B2 (ja) | 2011-07-27 |
| JP5449082B2 (ja) | 2014-03-19 |
| US6831192B2 (en) | 2004-12-14 |
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