ES2234969T3 - Procedimiento para la obtencion metilendi (fenilamina)y metilendi (fenilisocianato). - Google Patents
Procedimiento para la obtencion metilendi (fenilamina)y metilendi (fenilisocianato).Info
- Publication number
- ES2234969T3 ES2234969T3 ES02022029T ES02022029T ES2234969T3 ES 2234969 T3 ES2234969 T3 ES 2234969T3 ES 02022029 T ES02022029 T ES 02022029T ES 02022029 T ES02022029 T ES 02022029T ES 2234969 T3 ES2234969 T3 ES 2234969T3
- Authority
- ES
- Spain
- Prior art keywords
- formaldehyde
- aniline
- reaction mixture
- temperature
- reaction
- 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.)
- Expired - Lifetime
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 52
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 172
- 239000011541 reaction mixture Substances 0.000 claims abstract description 55
- 239000003377 acid catalyst Substances 0.000 claims abstract description 29
- 238000002156 mixing Methods 0.000 claims abstract description 17
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 14
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 210000000056 organ Anatomy 0.000 claims abstract description 9
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010924 continuous production Methods 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 230000003068 static effect Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000005496 tempering Methods 0.000 abstract description 4
- 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 49
- 238000009434 installation Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 14
- 150000002513 isocyanates Chemical class 0.000 description 13
- -1 poly (oxymethylene) Polymers 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000000178 monomer Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920001228 polyisocyanate Polymers 0.000 description 8
- 239000005056 polyisocyanate Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000008098 formaldehyde solution Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- VULHYRAYXYTONQ-UHFFFAOYSA-N n-phenylmethanimine Chemical compound C=NC1=CC=CC=C1 VULHYRAYXYTONQ-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000000926 separation method Methods 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
- 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
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 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
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000126 substance Substances 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
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 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
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-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
- 229910000851 Alloy steel Inorganic materials 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 125000004429 atom Chemical group 0.000 description 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical group NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 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
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 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
- 239000011707 mineral Substances 0.000 description 1
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical class C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 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
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- JSUMUQNOVBYHNZ-UHFFFAOYSA-N tris(2-decylphenyl) phosphite Chemical compound CCCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCCC)OC1=CC=CC=C1CCCCCCCCCC JSUMUQNOVBYHNZ-UHFFFAOYSA-N 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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19804915A DE19804915A1 (de) | 1998-02-07 | 1998-02-07 | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| DE19804915 | 1998-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2234969T3 true ES2234969T3 (es) | 2005-07-01 |
Family
ID=7856961
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99906202T Expired - Lifetime ES2198894T3 (es) | 1998-02-07 | 1999-01-26 | Procedimiento para la obtencion de metilendi(fenilamina) y metilendi(fenilisocianato). |
| ES02022029T Expired - Lifetime ES2234969T3 (es) | 1998-02-07 | 1999-01-26 | Procedimiento para la obtencion metilendi (fenilamina)y metilendi (fenilisocianato). |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99906202T Expired - Lifetime ES2198894T3 (es) | 1998-02-07 | 1999-01-26 | Procedimiento para la obtencion de metilendi(fenilamina) y metilendi(fenilisocianato). |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US6433219B1 (enExample) |
| EP (2) | EP1053222B1 (enExample) |
| JP (2) | JP4731684B2 (enExample) |
| KR (1) | KR100555814B1 (enExample) |
| CN (2) | CN1266124C (enExample) |
| AU (1) | AU2621799A (enExample) |
| BR (1) | BR9907634A (enExample) |
| CA (1) | CA2320477A1 (enExample) |
| DE (3) | DE19804915A1 (enExample) |
| ES (2) | ES2198894T3 (enExample) |
| MX (1) | MXPA00007646A (enExample) |
| PT (2) | PT1270544E (enExample) |
| WO (1) | WO1999040059A1 (enExample) |
Families Citing this family (79)
| 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 |
| DE10141620A1 (de) | 2001-08-24 | 2003-03-06 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| 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 |
| DE102005014846A1 (de) * | 2005-03-30 | 2006-10-05 | Basf Ag | MDI Herstellung mittels Flüssigphasen- und Gasphasenphosgenierung |
| DE102005014244A1 (de) * | 2005-03-30 | 2006-10-05 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| 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 |
| 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 |
| 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 |
| ES2453145T3 (es) * | 2005-05-30 | 2014-04-04 | Huntsman International Llc | Procedimiento para la preparación de poliisocianatos de la serie difenilmetano |
| DE102005055189A1 (de) * | 2005-11-19 | 2007-05-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von 4,4'-Diphenylmethandiisocyanat |
| ES2364081T5 (es) * | 2005-12-08 | 2019-08-20 | Huntsman Int Llc | Procedimiento para preparar diaminodifenilmetanos |
| DE102006004041A1 (de) * | 2006-01-28 | 2007-08-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102006004047A1 (de) * | 2006-01-28 | 2007-08-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| WO2008049783A1 (de) | 2006-10-26 | 2008-05-02 | Basf Se | Verfahren zur herstellung von isocyanaten |
| CN101583594B (zh) * | 2006-11-07 | 2013-06-19 | 巴斯夫欧洲公司 | 生产异氰酸酯的方法 |
| JP5398546B2 (ja) * | 2007-01-08 | 2014-01-29 | ビーエーエスエフ ソシエタス・ヨーロピア | ジフェニルメタンジアミンの製造方法 |
| 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 |
| PT2167456E (pt) * | 2007-06-12 | 2012-01-05 | Basf Se | Processo para a produção de ácidos minerais a partir de soluções salinas |
| EP2042485A1 (en) | 2007-09-28 | 2009-04-01 | Huntsman International Llc | Process for fractionating a mixture of polyisocyanates |
| DE102008012037A1 (de) * | 2008-03-01 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Methylen-diphenyl-diisocyanaten |
| DE102008015123A1 (de) | 2008-03-20 | 2009-09-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| CN102046588A (zh) * | 2008-05-26 | 2011-05-04 | 巴斯夫欧洲公司 | 制备二苯基甲烷二胺的方法 |
| EP2421818B1 (de) * | 2009-04-24 | 2014-08-27 | Basf Se | Verfahren zur herstellung von farbstabilem mda und mdi |
| US8829243B2 (en) * | 2009-09-02 | 2014-09-09 | Huntsman International Llc | Method for removing methylene-bridged polyphenyl polyamines from an aqueous stream |
| KR20120093962A (ko) * | 2009-10-20 | 2012-08-23 | 바스프 에스이 | 디페닐메탄 디이소시아네이트(ｍｄｉ)의 제조 및 바람직하게는 증류에 의한 후처리 방법 |
| JP5746205B2 (ja) | 2009-12-04 | 2015-07-08 | 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 |
| PT2513038E (pt) | 2009-12-18 | 2015-03-05 | Basf Se | Processo em duas etapas para a separação económica de catalisadores homogéneos na síntese de mda |
| US20110230679A1 (en) * | 2010-03-16 | 2011-09-22 | Dow Global Technologies, Inc. | Reactive Static Mixer |
| US20110228630A1 (en) * | 2010-03-16 | 2011-09-22 | Dow Global Technologies, Inc. | Reduced Transit Static Mixer Configuration |
| US8907124B2 (en) | 2010-11-17 | 2014-12-09 | Basf Se | Process for preparing methylenedi(phenyl isocyanate) |
| BR112013012255A2 (pt) | 2010-11-17 | 2016-08-09 | Basf Se | processo para preparar di - isocianato de metileno difenila |
| EP2486975B1 (en) * | 2010-12-29 | 2015-09-23 | Wanhua Chemical Group Co., Ltd. | Fast mixing reactor and use thereof |
| KR20140037139A (ko) | 2011-05-24 | 2014-03-26 | 바스프 에스이 | 바이오매스로부터 폴리이소시아네이트의 제조 방법 |
| US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
| CN102516126A (zh) * | 2011-11-29 | 2012-06-27 | 广州秀珀化工股份有限公司 | 一种烷基取代的二苯基甲烷二异氰酸酯的制备方法 |
| US20140131275A1 (en) | 2012-11-15 | 2014-05-15 | Bayer Intellectual Property Gmbh | Process for phase separation or extraction and device suitable therefor |
| US9309184B2 (en) | 2013-04-11 | 2016-04-12 | Covestro Deutschland Ag | Method for producing diamines and polyamines of the diphenylmethane series |
| KR20150142005A (ko) | 2013-04-11 | 2015-12-21 | 코베스트로 도이칠란트 아게 | 디페닐메탄 계열의 디- 및 폴리아민의 제조 방법 |
| CN105358524B (zh) | 2013-04-24 | 2018-02-16 | 科思创德国股份公司 | 制备二苯基甲烷系列的二胺和多胺的方法 |
| WO2015197527A1 (de) * | 2014-06-24 | 2015-12-30 | Covestro Deutschland Ag | Verfahren zur herstellung von di- und polyaminen der diphenylmethanreihe |
| KR102415515B1 (ko) | 2014-06-24 | 2022-07-01 | 코베스트로 도이칠란트 아게 | 작동 중단을 갖는 화학 생성물의 제조 방법 |
| PT3160936T (pt) * | 2014-06-24 | 2021-12-29 | Covestro Intellectual Property Gmbh & Co Kg | Processo para a produção de diaminas e poliaminas da gama difenilmetano |
| JP6655559B2 (ja) * | 2014-06-24 | 2020-02-26 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ジフェニルメタン系ジアミンおよびポリアミンの製造方法 |
| KR102797879B1 (ko) | 2015-11-20 | 2025-04-22 | 코베스트로 도이칠란트 아게 | 아미노벤조산 또는 아미노벤조산 유도체의 제조 방법 |
| US11028042B2 (en) | 2016-01-20 | 2021-06-08 | Basf Se | Process for preparing an aromatic polyamine mixture |
| HUE049575T2 (hu) | 2016-06-29 | 2020-09-28 | Covestro Deutschland Ag | Eljárás anilin vagy egy anilin-származék elõállítására |
| EP3500553B1 (de) | 2016-08-17 | 2021-05-12 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung eines isocyanats und mindestens eines weiteren chemischen produkts in einem produktionsverbund |
| PT3512830T (pt) * | 2016-09-14 | 2025-03-21 | Basf Se | Processo de hidrogenação de uma mistura na presença de uma amina incolor |
| EP3558931B1 (de) | 2016-12-20 | 2022-04-20 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von aminobenzoesäure oder eines aminobenzoesäurefolgeprodukts |
| CN110088078B (zh) | 2016-12-22 | 2022-09-09 | 科思创德国股份有限公司 | 生产二苯基甲烷系列的二胺和多胺的方法 |
| US10640453B2 (en) | 2016-12-22 | 2020-05-05 | Covestro Deutschland Ag | Method of producing diamines and polyamines of the diphenylmethane series |
| WO2018114765A1 (de) | 2016-12-22 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur herstellung von di- und polyaminen der diphenylmethanreihe bei unterschiedlichen produktions-kapazitäten |
| WO2018114767A1 (de) | 2016-12-22 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur herstellung von di- und polyaminen der diphenylmethanreihe bei unterschiedlichen produktionskapazitäten |
| US11453897B2 (en) | 2018-06-07 | 2022-09-27 | Covestro Intellectual Property Gmbh & Co. Kg | Method for producing aminobenzoic acid or an aminobenzoic acid derivative product |
| BR112021001332B1 (pt) | 2018-07-27 | 2024-02-20 | Covestro Intellectual Property Gmbh & Co. Kg | Processo para preparar anilina ou um produto de conversão de anilina |
| CN110387031B (zh) * | 2019-07-12 | 2021-06-29 | 万华化学集团股份有限公司 | 一种浅色异氰酸酯制备方法 |
| CN111646927A (zh) * | 2020-06-12 | 2020-09-11 | 万华节能科技集团股份有限公司 | 阻燃二苯基甲烷二异氰酸酯的衍生物及其合成方法 |
| KR20240012559A (ko) * | 2021-05-25 | 2024-01-29 | 바스프 에스이 | 적어도 1종의 폴리이소시아네이트의 제조 방법 |
| US20240199529A1 (en) | 2021-06-02 | 2024-06-20 | Covestro Deutschland Ag | Process for preparing aniline or an aniline derivative |
| US20250223255A1 (en) | 2022-04-06 | 2025-07-10 | Covestro Deutschland Ag | Method for producing aniline or an aniline-derived product |
| CN115124431B (zh) * | 2022-06-30 | 2023-08-11 | 万华化学集团股份有限公司 | 一种低n甲基杂质含量的二苯基甲烷系列的二胺和多胺的制备方法 |
| US11542223B1 (en) | 2022-07-21 | 2023-01-03 | Covestro Llc | Process for preparing di- and polyamines of the diphenyl methane series |
| EP4345088B1 (en) | 2022-09-29 | 2025-10-22 | Covestro Deutschland AG | A process for preparing di- and polyamines of the diphenyl methane series |
| KR102893774B1 (ko) * | 2022-12-19 | 2025-12-01 | 금호미쓰이화학 주식회사 | 메틸렌디아닐린의 제조방법 |
| WO2025073928A1 (en) | 2023-10-06 | 2025-04-10 | Basf Se | Process for preparing mda |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE238042C (enExample) | ||||
| DE295628C (enExample) | ||||
| BE755243Q (fr) * | 1965-07-08 | 1971-02-01 | Upjohn Co | Procedes de fabrication d'isocyanates et de polyisocyanates |
| GB1298258A (en) * | 1970-08-07 | 1972-11-29 | Ici Ltd | Manufacture of polyamines |
| BE794328A (fr) * | 1972-01-28 | 1973-07-19 | Ici Ltd | Procede de production de polyarylamines a pont methylenique |
| DE2426116B2 (de) | 1973-06-01 | 1978-05-11 | Efim Freiburg Biller (Schweiz) | Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen |
| US4189354A (en) * | 1976-07-10 | 1980-02-19 | Bayer Aktiengesellschaft | Process for the production of diisocyanatodiphenyl methane isomers with an adjusted content of chlorine compounds |
| DE2750975A1 (de) * | 1976-11-19 | 1978-05-24 | Mobay Chemical Corp | Verfahren zur herstellung von polyaminen der diphenylmethan-reihe |
| DD238042B1 (de) * | 1985-06-05 | 1987-09-30 | Schwarzheide Synthesewerk Veb | Verfahren zur kontinuierlichen herstellung von hochwertigen aromatischen isocyanaten |
| DD295628A5 (de) | 1986-12-15 | 1991-11-07 | Basf Schwarzheide Gmbh,De | Verfahren zur diskontinuierlichen herstellung von methylendianilin/polyamingemischen |
| JP2825604B2 (ja) | 1990-04-11 | 1998-11-18 | 三井化学株式会社 | メチレン架橋されたポリアリールアミンの製造方法 |
| EP0451422A1 (en) | 1990-04-13 | 1991-10-16 | Merrell Dow Pharmaceuticals Inc. | Pharmaceutically active fluoromethyltyrosine compounds |
| DE4021712A1 (de) * | 1990-07-07 | 1992-01-09 | Basf Ag | Verfahren zur herstellung von mischungen aus diphenylmethan-diisocyanaten und polyphenol-polymethylen-polyisocyanaten mit einer verminderten iodfarbzahl |
| DE69107212T2 (de) * | 1991-10-19 | 1995-05-24 | Basf Corp | Verfahren zur Herstellung von polymerischen Methylen-dyphenylen-diisocyanaten mit verminderter Farbe und Chloridgehalt. |
| US5286760A (en) * | 1992-10-09 | 1994-02-15 | Miles, Inc. | Process for reducing impurity levels in methylene diphenyamines |
| KR0147558B1 (ko) * | 1992-10-23 | 1998-10-15 | 윤종용 | 테이프 레코더의 슬라이더 하우징 록킹장치 |
| 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 |
| CN1077099C (zh) * | 1994-11-17 | 2002-01-02 | 拜尔公司 | 制备异氰酸酯的方法 |
| DE19523851A1 (de) | 1995-06-30 | 1997-01-02 | Basf Ag | Verfahren zur Herstellung von Mischungen aus Diphenylmethan-diisocyanaten und Polyphenyl-polymethylen-polyisocyanaten mit einer verminderten Iodfarbzahl und einem reduzierten Chlorgehalt |
| DE19804915A1 (de) * | 1998-02-07 | 1999-08-12 | Basf Ag | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
-
1998
- 1998-02-07 DE DE19804915A patent/DE19804915A1/de not_active Withdrawn
-
1999
- 1999-01-26 CA CA002320477A patent/CA2320477A1/en not_active Abandoned
- 1999-01-26 JP JP2000530491A patent/JP4731684B2/ja not_active Expired - Fee Related
- 1999-01-26 DE DE59911344T patent/DE59911344D1/de not_active Expired - Lifetime
- 1999-01-26 DE DE59905323T patent/DE59905323D1/de not_active Expired - Lifetime
- 1999-01-26 ES ES99906202T patent/ES2198894T3/es not_active Expired - Lifetime
- 1999-01-26 EP EP99906202A patent/EP1053222B1/de not_active Expired - Lifetime
- 1999-01-26 KR KR1020007008609A patent/KR100555814B1/ko not_active Expired - Lifetime
- 1999-01-26 CN CNB2004100317075A patent/CN1266124C/zh not_active Expired - Lifetime
- 1999-01-26 BR BR9907634-9A patent/BR9907634A/pt not_active Application Discontinuation
- 1999-01-26 WO PCT/EP1999/000472 patent/WO1999040059A1/de not_active Ceased
- 1999-01-26 AU AU26217/99A patent/AU2621799A/en not_active Abandoned
- 1999-01-26 PT PT02022029T patent/PT1270544E/pt unknown
- 1999-01-26 EP EP02022029A patent/EP1270544B1/de not_active Expired - Lifetime
- 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 ES ES02022029T patent/ES2234969T3/es not_active Expired - Lifetime
- 1999-01-26 PT PT99906202T patent/PT1053222E/pt unknown
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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
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| KR20010040725A (ko) | 2001-05-15 |
| DE59911344D1 (de) | 2005-01-27 |
| US20020132953A1 (en) | 2002-09-19 |
| EP1053222B1 (de) | 2003-05-02 |
| US6433219B1 (en) | 2002-08-13 |
| BR9907634A (pt) | 2000-11-14 |
| EP1053222A1 (de) | 2000-11-22 |
| PT1053222E (pt) | 2003-09-30 |
| US6831192B2 (en) | 2004-12-14 |
| CN1266124C (zh) | 2006-07-26 |
| JP2010270147A (ja) | 2010-12-02 |
| CN1290245A (zh) | 2001-04-04 |
| JP5449082B2 (ja) | 2014-03-19 |
| US20050014975A1 (en) | 2005-01-20 |
| ES2198894T3 (es) | 2004-02-01 |
| CA2320477A1 (en) | 1999-08-12 |
| CN1151119C (zh) | 2004-05-26 |
| PT1270544E (pt) | 2005-05-31 |
| JP4731684B2 (ja) | 2011-07-27 |
| DE59905323D1 (de) | 2003-06-05 |
| MXPA00007646A (es) | 2001-04-01 |
| DE19804915A1 (de) | 1999-08-12 |
| WO1999040059A1 (de) | 1999-08-12 |
| EP1270544A1 (de) | 2003-01-02 |
| JP2002502838A (ja) | 2002-01-29 |
| KR100555814B1 (ko) | 2006-03-03 |
| EP1270544B1 (de) | 2004-12-22 |
| AU2621799A (en) | 1999-08-23 |
| US7230130B2 (en) | 2007-06-12 |
| CN1532189A (zh) | 2004-09-29 |
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