WO2008071564A1 - Verfahren zur herstellung von isocyanaten - Google Patents
Verfahren zur herstellung von isocyanaten Download PDFInfo
- Publication number
- WO2008071564A1 WO2008071564A1 PCT/EP2007/063070 EP2007063070W WO2008071564A1 WO 2008071564 A1 WO2008071564 A1 WO 2008071564A1 EP 2007063070 W EP2007063070 W EP 2007063070W WO 2008071564 A1 WO2008071564 A1 WO 2008071564A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- reaction
- mixing
- din
- iso
- october
- Prior art date
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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
-
- 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
Definitions
- the present invention relates to a process for the preparation of isocyanates in certain apparatuses.
- solid ureas can be formed by contact of intermediates as well as the isocyanates with the amine used. Also subsequent products of the isocyanate such as diimides and isocyanurates are often solid under the reaction conditions.
- GB 1 165831 proposes, for example, for the reaction of aromatic or aliphatic amines in the gas phase, a reaction in a stirred reactor.
- EP 289840 B1 describes carrying out a gas phase phosgenation in a reaction space without moving parts. The deposition of clogging particles is prevented here by a turbulent flow.
- EP 928785 B1 reduces the formation of solids by the use of complex microstructure mixers.
- the object of the present invention was to provide a process with which the formation of deposits in an apparatus for the preparation of isocyanates by phosgenation of amines are reduced.
- the object has been achieved by a process for the preparation of diisocyanates by reacting the corresponding amines with phosgene optionally in the presence of inert, in which the implementation takes place at least partially in an apparatus whose fluid contact surface has an average roughness Rz according to DIN EN ISO 4287 (October 1998 version) of not more than 10 microns.
- the amines may be monoamines, diamines, triamines or higher amines, preferably diamines. Accordingly, the corresponding monoisocyanates, diisocyanates, triisocyanates or higher isocyanates, preferably diisocyanates, are obtained.
- the amines and isocyanates may be aliphatic, cycloaliphatic or aromatic, preferably aliphatic or cycloaliphatic and more preferably aliphatic.
- Cycloaliphatic isocyanates are those which contain at least one cycloaliphatic ring system.
- Aliphatic isocyanates are those which have exclusively isocyanate groups attached to straight or branched chains.
- Aromatic isocyanates are those which have at least one isocyanate group bonded to at least one aromatic ring system.
- (Cyclo) aliphatic isocyanates are in the context of this application briefly for cycloaliphatic and / or aliphatic isocyanates.
- aromatic diisocyanates are preferably those having 6 to 20 carbon atoms, for example monomeric 2,4'- or 4,4'-methylene-di (phenyl isocyanate (MDI), 2,4- and / or 2,6-toluene diisocyanate (TDI), o-, m- or p-xylenediisocyanate (XDI) and 1, 5- or 1, 8-naphthyl diisocyanate (NDI).
- MDI phenyl isocyanate
- TDI 2,4- and / or 2,6-toluene diisocyanate
- XDI o-, m- or p-xylenediisocyanate
- NDI 1, 5- or 1, 8-naphthyl diisocyanate
- Diisocyanates are preferably (cyclo) aliphatic diisocyanates, particularly preferably (cyclo) aliphatic diisocyanates having 4 to 20 C atoms.
- customary diisocyanates are aliphatic diisocyanates, such as 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate, 1,6-hexamethylene diisocyanate (1,6-diisocyanatohexane), 1,8-octamethylene diisocyanate, 1,10-decamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, 1,14-tetradecamethylene diisocyanate, derivatives of lysine diisocyanate, tetramethylxylylene diisocyanate (TMXDI), trimethylhexane diisocyanate or tetra-methylhexane diisocyanate, and also 3 (or 4), 8 (or 9) -bis (isocyanatomethyl) -tricyclo [5.2.1.0 26 ] decane isomer mixtures, and also cycloaliphatic diisocyanates such as 1, 4- , 1,
- amines which can be used in a gas phase phosgenation must meet certain requirements:
- such amines can be used for the reaction to the corresponding isocyanates in which the amine, its corresponding intermediates and the corresponding isocyanates are gaseous at the reaction conditions chosen.
- Particularly suitable here are amines, in particular diamines, based on aliphatic or cycloaliphatic hydrocarbons having 2 to 18 carbon atoms.
- Examples of these are 1,5-diaminopentane, 1,6-diaminohexane, 1-amino-3,3,5-trimethyl-5-aminomethylcyclohexane (IPDA) and 4,4'-diaminodicyclohexylmethane. Preference is given to using 1,6-diaminohexane (HDA).
- aromatic amines can be used for the process according to the invention, which can be converted into the gas phase without significant decomposition.
- aromatic amines are toluenediamine (TDA), as a 2,4- or 2,6-isomer or as a mixture thereof, for example as 80:20 to 65:35 (mol / mol) mixture, diaminobenzene, 2,6-xylidine Naphthyldiamine (NDA) and 2,4'- or 4,4'-methylene (diphenylamine) (MDA) or isomer mixtures thereof.
- TDA toluenediamine
- NDA 2,4-xylidine Naphthyldiamine
- MDA 2,4'- or 4,4'-methylene
- isomer mixtures thereof Preferred among these are the diamines, more preferably 2,4- and / or 2,6-TDA.
- the compounds occurring in the course of the reaction ie starting materials (diamine and phosgene), intermediates (in particular the intermediately formed mono- and dicarbamyl chlorides), end products (diisocyanate), and optionally metered inert compounds, remain under the reaction conditions in the gas phase. Should this or other components are deposited from the gas phase, for example, on the reactor wall or other apparatus components, it can be changed by these deposits, the heat transfer or the flow through the affected components undesirable. This is especially true for occurring amine hydrochlorides, which are formed from free amino groups and hydrogen chloride (HCl), since the resulting amine hydrochlorides are easily precipitated and are difficult to re-evaporate.
- starting materials diamine and phosgene
- intermediates in particular the intermediately formed mono- and dicarbamyl chlorides
- end products diisocyanate
- optionally metered inert compounds optionally metered inert compounds
- the phosgene which can be used in the process according to the invention is subject in principle to no restrictions.
- phosgene containing less than 50 ppm of bromine and iodine, as disclosed in WO 01/00569.
- Inert are compounds which can be used as solvent in the liquid phase phosgenation or as intere admixture in the gas phase phosgenation.
- Inert means that less than 5 mol% of the solvent used per reaction passage are chemically changed in the course of the reaction, preferably less than 3 mol%, more preferably less than 2 and most preferably less than 1 mol%.
- the solvents used are chlorobenzene, o- or p-dichlorobenzene, trichlorobenzene, chlorotoluenes, chloroxylenes, chloroethylbenzene, chloronaphthalenes, chlorodiphenyls, methylene chloride, perchlorethylene, toluene, xylene, hexane, decahydronaphthalene, diethylphthalate (DEIP) and other carboxylic acid esters, such as, for example in the US
- the inert medium is a medium which is gaseous in the reaction space at the reaction temperature and does not react with the compounds occurring in the course of the reaction.
- the inert medium is generally mixed with amine and / or phosgene before the reaction, but can also be metered in separately from the educt streams.
- nitrogen, noble gases such as helium or argon, or aromatics such as chlorobenzene, chlorotoluene, o-dichlorobenzene, toluene, xylene, chloronaphthalene, decahydronaphthalene, carbon dioxide or carbon monoxide can be used.
- nitrogen and / or chlorobenzene is used as the inert medium.
- the inert medium is used in an amount such that the ratio of the gas volumes of inert medium to amine or to phosgene is more than 0.0001 to 30, preferably more than 0.01 to 15, particularly preferably more than 0.1 to 5 is.
- reaction in the gas phase is understood to mean that the conversion of the educt streams and intermediates to the products in the gaseous state react with each other and in the course of the reaction during the passage through the reaction space to at least 95%, preferably at least 98%, more preferably at least 99%, very particularly preferably at least 99.5%, in particular at least 99.8 and especially at least 99.9% remain in the gas phase.
- the starting amines are evaporated before carrying out the process according to the invention and heated to 200 0 C to 600 0 C, preferably 300 ° C to 500 0 C and optionally diluted with an inert gas or with the vapors of an inert solvent fed through the mixer to the reactor ,
- reactor is meant the technical device containing the reaction space.
- the phosgene used in the phosgenation is optionally diluted with an inert gas or with the vapors of an inert solvent to a temperature within the range of 200 ° C to 600 ° C, preferably 300 0 C to 500 ° C before carrying out the inventive method heated.
- the reaction of phosgene with amine in the reaction space in the gas phase phosgenation is generally carried out at absolute pressures of more than 0.1 bar to less than 20 bar, preferably between 0.5 bar and 15 bar, and more preferably between 0.7 and 10 bar.
- the absolute pressure is very particularly preferably between 0.7 bar and 5 bar, in particular from 0.8 to 3 bar and especially 1 to 2 bar.
- the gas phase phosgenation can also be carried out at moderate pressures of 3 to 20 bar, as described in WO 2004/026813.
- reaction of amine and phosgene in the liquid phase phosgenation generally takes place between 20 ° C and 250 0 C, preferably between 40 and 230 0 C.
- the pressure is usually between 1, 0 bar and 80 bar abs.
- the reaction of amine with phosgene takes place to a predominant part in the liquid phase.
- a gas phase which consists for example predominantly of hydrogen chloride.
- the starting compounds are first mixed with one another in at least one mixing element and then reacted in at least one reaction space.
- the reaction effluent from the reaction space is then cooled in the gas phase phosgenation to stop the reaction in a so-called "quench" by contacting it with a solvent.
- the discharge from the reaction space in the liquid phase phosgenation or the discharge from the quench in the gas phase phosgenation is then usually purified by distillation.
- the mixing of the educt streams, wherein the amine can also be used as the hydrochloride, is often carried out in a suitable special mixing device, which is characterized by low mixing times.
- the mixing time in such mixing devices is usually from 0.0001 s to 2 s, preferably from 0.0005 to 1 s, particularly preferably from 0.001 to 0.5 s, very particularly preferably from 0.005 to 0.2 s and in particular from 0.007 to 0.1 s.
- the mixing time is to be understood as meaning the time which elapses from the beginning of the mixing operation until 97.5% of the fluid elements of the resulting mixture have a mixing fraction which, based on the value of the theoretical final value of the mixture break of the resulting mixture, on reaching the state, becomes more perfect Mixture less than 2.5% of this final value of the mixture break, (for the concept of mixture break see, for example, J. Warnatz, U.Maas, RW Dibble: combustion, Springer Verlag, Berlin Heidelberg New York, 1997, 2nd edition, p. 134.)
- the mixing device used is preferably a mixing circuit, a stirring vessel, a mixing pump or a nozzle mixing device, for example coaxial mixing nozzles, Y or T mixers, or a vortex impinging jet mixing configuration, preferably a mixing circuit, a stirring vessel, a mixing pump or a nozzle mixing device.
- the speeds are between 10 and 100 m / s, preferably between 20 and 80 m / s.
- a mixing nozzle and a mixing pump is used as a mixing device.
- a mixing nozzle is used as the mixing device. It is important that both the phosgene and amine speed are introduced into the mixing nozzle. The speeds are between 10 and 100 m / s, preferably between 20 and 80 m / s.
- the pressure in the amine and phosgene feed line to the nozzle is considerably higher than in the outlet of the mixing nozzle, but usually not higher than 110 bar abs, preferably not higher than 100 bar abs, more preferably 10 to 95 bar abs and most preferably 15 up to 90 bar abs.
- the pressure at the outlet of the mixing device is between 10 and 100 bar, preferably between 15 and 80 bar, more preferably between 30 and 70 bar.
- the temperature of the discharge from the mixer is usually from 25 to 240 0 C, preferably 30-190 and particularly preferably 40-160 0 C.
- the discharge from the mixing device can before it is introduced into the reaction space with the aid of a heat exchanger to the desired there Temperature be brought.
- the reaction space may include backmixed or non-backmixed reactors, as well as reactive distillation columns.
- Backmixed reactors are, for example, stirred tanks, stirred tank cascades from 2 to 4 stirred tanks, loop reactors or unstirred tanks.
- back-mixing-free reactors are, for example, tubular reactors. This is achieved for example by the ratio of the diameter of the tubular reactor to its length or by internals, such as perforated plates, slot floors or static mixer. Preferably, the backmixing freedom is achieved by the ratio of length to diameter of the tubular reactor.
- Suitable tubular reactors are all tubes whose length to diameter ratio is greater than 5, preferably greater than 6, particularly preferably greater than 10.
- a gas phase produced during the reaction can be moved in cocurrent or countercurrent to the liquid phase.
- Reactive distillation columns are of a type known per se and have the usual installations. In principle, all standard installations are suitable as column internals, for example trays, packings and / or fillings. From the bottoms, bubble-cap trays, sieve trays, valve trays, Thormann trays and / or dual-flow trays are preferred; of the trays are those with rings, coils, calipers, Raschig, Intos or Pall rings, Barrel or Intalox saddles, Top Pak etc. or Braided preferred.
- Floors are preferably used, more preferably bubble trays.
- the mean total residence time in the reaction space in the liquid phase phosgenation is generally between 20 minutes and 18 hours, preferably between 30 minutes and 15 hours, more preferably between 50 minutes and 11 hours.
- the starting materials and, if appropriate, inert are generally mixed with one another via at least one mixing device.
- the mixing device may preferably be static mixing elements, for example a nozzle mixing device, for example coaxial mixing nozzles, Y or T mixers, jet mixers or mixing tubes.
- a nozzle mixing device for example coaxial mixing nozzles, Y or T mixers, jet mixers or mixing tubes.
- one component preferably the amine
- the other component in this case phosgene
- the reactors can be, for example, cylindrical reaction spaces without internals and without moving parts.
- a preferred embodiment for a mixing nozzle is a slot mixing nozzle, as described in the European patent application with the file number
- a particularly preferred embodiment for a mixing nozzle is an annular gap mixing nozzle, as described in International Patent Application WO 2007/028715, there especially from page 2, line 23 to page 11, line 22 and a reaction chamber as described there from page 1 1, line 26 to page 21, line 15 together with Figure 2, which is hereby incorporated by reference in the present disclosure.
- the quench can be carried out, for example, as described in EP 1403248 A1, there in particular in paragraphs [0006] to [0019] and the example together with FIGS Figures 1 to 2, which is hereby incorporated by reference in the present disclosure.
- the quench can be embodied, for example, as described in the European patent application with the file reference 06123629.5 and the filing date
- the quench can be embodied, for example, as described in the European patent application with the file reference 06123621.2 and the filing date 7.1 1.2006, there especially from page 3, line 26 to page 16, line 36 together with Example 1 and the figures, which hereby incorporated by reference present disclosure.
- the quench may be preferably carried out as described in WO 2005/123665, there especially from page 3, line 10 to page 8, line 2 and the example, which is hereby incorporated by reference into the present disclosure.
- such surfaces should have a low roughness according to the invention which has contact with the two starting materials phosgene and amine and / or with one of the intermediates of the reaction, for example the corresponding carboylchlorides, preferably those surfaces which react with both educts phosgene and amine. have contact min.
- At least the surfaces with fluid contact of the reaction space according to the invention are designed to be less rough.
- fluid includes both liquid and gas phase.
- the mixing space can be defined as the area of the reaction space in which the mixing of the educts takes place to a degree of 99%.
- the turnover in the mixing space i. the consumption of the amine used, less than 15%.
- the degree of mixing is given as the ratio of the difference between the local average mixture fraction and the initial mixture fraction before mixing to the difference between the mean final mixture fraction after mixing and the initial mixture fraction before mixing.
- the reaction space is defined as the volume in which at least 98% of the conversion, i. the consumption of the amine used takes place, preferably at least 99%, particularly preferably 99.5%, very particularly preferably 99.7%, in particular 99.9% and especially 99.99%.
- the arithmetic mean roughness Ra according to DIN EN ISO 4287 (version of October 1998), which should not be more than 1, 5 microns, preferably not more than 1, 0 and more preferably not more than 0.8 microns.
- Ra The values for Rz and, where appropriate, Ra are preferably taken off with electrical touch-editing devices. This is preferably done in accordance with DIN EN ISO 4288.
- an electrical stylus with a highly sensitive diamond stylus probes the profile along the standardized probe path. It automatically a reference line is averaged, the so-called middle line. Basically, with the device a two-dimensional detection of the approximated image of the workpiece Surface captured. The highly sensitive probe tip travels over the surface contour during the roughness measurement.
- Suitable materials for contact with the reaction mixture are e.g. Metals, such as steel, in particular alloyed steel, tantalum, nickel, nickel alloys, silver or copper, glass, ceramics, enamels or homogeneous or heterogeneous mixtures and components thereof. Preference is given to using steel apparatuses, particularly preferably reactors.
- the apparatus from corrosion-resistant materials at least partially at the thermally stressed points at which the apparatus is exposed to the reaction mixture.
- corrosion-resistant materials include in particular stainless steels and nickel wrought alloys.
- Austenitic steels are those with lattice type austenitic ( ⁇ phase) at 20 0 C. vorzugt loading they have a Cr content of 16 to 28% and a Ni content of 3.5 to 32%, and optionally proportions of S (up to 0.35%), P (up to 0.045%), Mo (up to 7%), Si (up to 4.5%), Cu (up to 4%), N (up to 0.25 %) and / or Mn (up to 10.5%), and possibly Ti (up to 0.7%) and / or Nb (up to 1%).
- the carbon content is usually below 0.15%.
- the high-alloy austenitic 18/8 chrome-nickel steels are particularly preferred.
- Austenitic-ferritic steels have a two-phase structure of ferrite and austenite with a ferrite content of approximately 60%.
- the Cr content is usually 19-28%, Ni 3.5-8%, Mo up to 4.5%, and optional proportions of Mn (up to 2%), Cu (up to 2.5%), N ( up to 0.35%), W (up to 1%), S (up to 0.015%), Si (up to 1%), and / or P (up to 0.035%).
- the carbon content is usually less than 0.05%.
- Ataurous and austenitic-ferritic materials listed in DIN-EN 10088-1, and particularly preferred are the materials 1.4539 (Falk steel), 1.4541, 1.4571 and 1.4462, and furthermore also Hastelloy A and C and zircon.
- the mentioned materials according to DIN-EN 10088 correspond approximately to the following materials according to AISI (American Iron and Steel Institute), UNS (Unified Numbering System), SS (Swedish Standard), AFNOR (Association Francaise de Normalization), BS (British Standard) and JIS (Japanese Industrial Standards):
- Stainless steels can also be nickel and nickel wrought alloys (material designations 2.4xxx according to DIN 17744: 2002-09) are used.
- these materials may contain higher proportions of cobalt, copper, iron, manganese, niobium and / or tantalum and tungsten.
- nickel-containing nickel-wrought alloys with the material designations 2.4xxx according to DIN 17744: 2002-09 can be used.
- the apparatuses with the inventively low roughness are usually produced by a multi-stage production with separating manufacturing processes.
- the first production step such as drilling, milling or turning
- further production steps can also be drilling, milling or turning, but then with changed parameters, eg a reduced feed rate (fine finishing).
- Other separating manufacturing processes such as grinding, mechanical and / or electropolishing, honing or lapping can also be used.
- rough surfaces can also be smoothed by applying methods such as coating, plating, electroplating or the like.
- the formation of deposits in the liquid-phase phosgenation and gas-phase phosgenation, preferably in the gas-phase phosgenation, can be reduced.
- the average roughness Ra for the nozzle was 1.97 ⁇ m.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07847586.0A EP2089357B1 (de) | 2006-12-11 | 2007-11-30 | Verfahren zur herstellung von isocyanaten |
JP2009540703A JP2010512364A (ja) | 2006-12-11 | 2007-11-30 | イソシアネートの製造法 |
US12/515,554 US20100048942A1 (en) | 2006-12-11 | 2007-11-30 | Process for preparing isocyanates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06125811.7 | 2006-12-11 | ||
EP06125811 | 2006-12-11 |
Publications (1)
Publication Number | Publication Date |
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WO2008071564A1 true WO2008071564A1 (de) | 2008-06-19 |
Family
ID=39148774
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/063070 WO2008071564A1 (de) | 2006-12-11 | 2007-11-30 | Verfahren zur herstellung von isocyanaten |
Country Status (6)
Country | Link |
---|---|
US (1) | US20100048942A1 (de) |
EP (1) | EP2089357B1 (de) |
JP (1) | JP2010512364A (de) |
KR (1) | KR20090088384A (de) |
CN (1) | CN101568519A (de) |
WO (1) | WO2008071564A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009542770A (ja) * | 2006-07-13 | 2009-12-03 | 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 |
DE102008063991A1 (de) | 2008-12-19 | 2010-06-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
WO2010100221A1 (de) * | 2009-03-06 | 2010-09-10 | Basf Se | Verfahren und vorrichtung zur herstellung von isocyanaten |
WO2016198404A1 (de) | 2015-06-12 | 2016-12-15 | Covestro Deutschland Ag | Verfahren zur herstellung von diisocyanaten in der gasphase |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101436181B1 (ko) * | 2006-11-07 | 2014-09-01 | 바스프 에스이 | 이소시아네이트 생산 방법 |
WO2009027232A1 (de) | 2007-08-30 | 2009-03-05 | Basf Se | Verfahren zur herstellung von isocyanaten |
EP2188248A1 (de) * | 2007-08-30 | 2010-05-26 | Basf Se | Verfahren zur herstellung von isocyanaten |
EP2200976B1 (de) | 2007-09-19 | 2011-11-23 | Basf Se | Verfahren zur herstellung von isocyanaten |
WO2009094032A1 (en) | 2008-01-25 | 2009-07-30 | Midwest Research Institute | Indirect evaporative cooler using membrane-contained, liquid desiccant for dehumidification |
EP2307356B1 (de) * | 2008-07-23 | 2012-06-06 | Basf Se | Verfahren zur herstellung von isocyanaten |
JP2012197272A (ja) * | 2011-03-09 | 2012-10-18 | Mitsubishi Chemicals Corp | 共役ジエンの製造方法 |
US9140460B2 (en) | 2013-03-13 | 2015-09-22 | Alliance For Sustainable Energy, Llc | Control methods and systems for indirect evaporative coolers |
US9140471B2 (en) | 2013-03-13 | 2015-09-22 | Alliance For Sustainable Energy, Llc | Indirect evaporative coolers with enhanced heat transfer |
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EP0928785A1 (de) * | 1998-01-09 | 1999-07-14 | Bayer Aktiengesellschaft | Verfahren zur Phosgenierung von Aminen in der Gasphase unter Einsatz von Mikrostrukturmischern |
WO2005115974A1 (de) * | 2004-05-25 | 2005-12-08 | Basf Aktiengesellschaft | Verfahren zur herstellung von isocyanaten |
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US3167395A (en) * | 1958-08-26 | 1965-01-26 | Union Carbide Corp | Resonating pulse reactor |
DE2703280A1 (de) * | 1977-01-27 | 1978-08-10 | Hoechst Ag | Verfahren zur herstellung von vinylchlorid-polymerisation |
DE3714439A1 (de) * | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
JPH0734909Y2 (ja) * | 1990-09-25 | 1995-08-09 | 日本エステル株式会社 | エステル化反応装置 |
JP2924259B2 (ja) * | 1991-04-11 | 1999-07-26 | 住友化学工業株式会社 | ナフトール類のスルフィド化合物からなる重合器内部表面の付着防止剤及び該付着防止剤を用いたビニル系単量体の重合方法 |
JP3719448B2 (ja) * | 1993-07-29 | 2005-11-24 | 三菱瓦斯化学株式会社 | 芳香族ジカルボン酸製造用酸化反応器 |
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DE10133729A1 (de) * | 2001-07-11 | 2003-01-23 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
DE10238995A1 (de) * | 2002-08-20 | 2004-02-26 | Basf Ag | Gasphasenphosgenierung bei moderaten Drücken |
DE10245704A1 (de) * | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
DE10260082A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
DE10307141A1 (de) * | 2003-02-20 | 2004-09-02 | Bayer Ag | Verfahren zur Herstellung von (Poly)isocyanaten in der Gasphase |
DE10359627A1 (de) * | 2003-12-18 | 2005-07-21 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diisocyanaten |
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2007
- 2007-11-30 EP EP07847586.0A patent/EP2089357B1/de active Active
- 2007-11-30 JP JP2009540703A patent/JP2010512364A/ja active Pending
- 2007-11-30 KR KR1020097011101A patent/KR20090088384A/ko not_active Application Discontinuation
- 2007-11-30 CN CNA2007800457585A patent/CN101568519A/zh active Pending
- 2007-11-30 WO PCT/EP2007/063070 patent/WO2008071564A1/de active Application Filing
- 2007-11-30 US US12/515,554 patent/US20100048942A1/en not_active Abandoned
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EP0928785A1 (de) * | 1998-01-09 | 1999-07-14 | Bayer Aktiengesellschaft | Verfahren zur Phosgenierung von Aminen in der Gasphase unter Einsatz von Mikrostrukturmischern |
WO2005115974A1 (de) * | 2004-05-25 | 2005-12-08 | Basf Aktiengesellschaft | Verfahren zur herstellung von isocyanaten |
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DE102008063991A1 (de) | 2008-12-19 | 2010-06-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
CN101747232B (zh) * | 2008-12-19 | 2014-01-29 | 拜耳材料科技股份有限公司 | 在气相中制备异氰酸酯的方法 |
US9365503B2 (en) | 2008-12-19 | 2016-06-14 | Covestro Deutschland Ag | Process for the preparation of isocyanates in the gas phase |
WO2010100221A1 (de) * | 2009-03-06 | 2010-09-10 | Basf Se | Verfahren und vorrichtung zur herstellung von isocyanaten |
CN102341369A (zh) * | 2009-03-06 | 2012-02-01 | 巴斯夫欧洲公司 | 用于制备异氰酸酯的方法和装置 |
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WO2016198404A1 (de) | 2015-06-12 | 2016-12-15 | Covestro Deutschland Ag | Verfahren zur herstellung von diisocyanaten in der gasphase |
Also Published As
Publication number | Publication date |
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KR20090088384A (ko) | 2009-08-19 |
JP2010512364A (ja) | 2010-04-22 |
EP2089357A1 (de) | 2009-08-19 |
CN101568519A (zh) | 2009-10-28 |
EP2089357B1 (de) | 2016-09-21 |
US20100048942A1 (en) | 2010-02-25 |
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