SE448627B - Forfarande for framstellning av aromatiska isocyanater genom karbonylering av nitroderivat i nervaro av zeoliter innehallande en aktiv metall - Google Patents

Forfarande for framstellning av aromatiska isocyanater genom karbonylering av nitroderivat i nervaro av zeoliter innehallande en aktiv metall

Info

Publication number: SE448627B
Authority: SE; Sweden
Prior art keywords: process according; catalyst; zeolite; reaction; metal
Prior art date: 1979-11-27

Application number

SE8007426A

Other languages

English (en)

Swedish (sv)

Other versions

SE8007426L (sv

Inventor

J Kervennal

Y B Tarrit

B Elleuch

Original Assignee

Rhone Poulenc Chim Base

Priority date (The priority date 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 date listed.)

1979-11-27

Filing date

1980-10-22

Publication date

1987-03-09

1980-10-22 Application filed by Rhone Poulenc Chim Base filed Critical Rhone Poulenc Chim Base

1981-05-28 Publication of SE8007426L publication Critical patent/SE8007426L/xx

1987-03-09 Publication of SE448627B publication Critical patent/SE448627B/sv

Links

239000010457 zeolite Substances 0.000 title claims description 36
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 title claims description 29
229910052751 metal Inorganic materials 0.000 title claims description 29
239000002184 metal Substances 0.000 title claims description 29
238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 6
239000012948 isocyanate Substances 0.000 title description 12
150000002513 isocyanates Chemical class 0.000 title description 12
230000006315 carbonylation Effects 0.000 title description 4
238000005810 carbonylation reaction Methods 0.000 title description 4
229910021536 Zeolite Inorganic materials 0.000 claims description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
239000003054 catalyst Substances 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 17
229910052763 palladium Inorganic materials 0.000 claims description 13
150000002828 nitro derivatives Chemical class 0.000 claims description 12
-1 aromatic nitro derivatives Chemical class 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
150000002739 metals Chemical class 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 3
230000003213 activating effect Effects 0.000 claims description 2
125000005442 diisocyanate group Chemical group 0.000 claims description 2
239000007791 liquid phase Substances 0.000 claims description 2
230000000694 effects Effects 0.000 claims 3
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 42
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 20
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 12
230000035484 reaction time Effects 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000012013 faujasite Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
229910052703 rhodium Inorganic materials 0.000 description 4
239000010948 rhodium Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
239000000126 substance Substances 0.000 description 3
RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-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
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
BSNKHEKTRWNNAC-UHFFFAOYSA-N 1,2-Bis(4-nitrophenyl)ethane Chemical group C1=CC([N+](=O)[O-])=CC=C1CCC1=CC=C([N+]([O-])=O)C=C1 BSNKHEKTRWNNAC-UHFFFAOYSA-N 0.000 description 1
IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
MOTOIPZLXGKQIX-UHFFFAOYSA-N 1,4-dinitrobenzene;nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1.[O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1 MOTOIPZLXGKQIX-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
FGCPLOGNRVKJNZ-UHFFFAOYSA-N 1-nitro-2-[2-(4-nitrophenyl)ethenyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=CC=C1[N+]([O-])=O FGCPLOGNRVKJNZ-UHFFFAOYSA-N 0.000 description 1
AXIZPDWIUAIAIV-UHFFFAOYSA-N 1-nitro-2-[2-(4-nitrophenyl)ethyl]benzene Chemical group C1=CC([N+](=O)[O-])=CC=C1CCC1=CC=CC=C1[N+]([O-])=O AXIZPDWIUAIAIV-UHFFFAOYSA-N 0.000 description 1
DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 1
CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 description 1
XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 1
PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
CLVIIRIMEIEKOQ-OWOJBTEDSA-N 4,4'-Dinitrostilbene Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 CLVIIRIMEIEKOQ-OWOJBTEDSA-N 0.000 description 1
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 1
ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000012072 active phase Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
238000004061 bleaching Methods 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
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910052663 cancrinite Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
229910052675 erionite Inorganic materials 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910001683 gmelinite Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
DDSZSJDMRGXEKQ-UHFFFAOYSA-N iron(3+);borate Chemical class [Fe+3].[O-]B([O-])[O-] DDSZSJDMRGXEKQ-UHFFFAOYSA-N 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052680 mordenite Inorganic materials 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910052665 sodalite Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 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
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/084—Y-type faujasite
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/14—Preparation of derivatives of isocyanic acid by catalytic reaction of nitro compounds with carbon monoxide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SE8007426A 1979-11-27 1980-10-22 Forfarande for framstellning av aromatiska isocyanater genom karbonylering av nitroderivat i nervaro av zeoliter innehallande en aktiv metall SE448627B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7929123A FR2470115A1 (fr)	1979-11-27	1979-11-27	Procede de fabrication d'isocyanates aromatiques par carbonylation des derives nitres en presence de zeolithes contenant un metal actif

Publications (2)

Publication Number	Publication Date
SE8007426L SE8007426L (sv)	1981-05-28
SE448627B true SE448627B (sv)	1987-03-09

Family

ID=9232114

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8007426A SE448627B (sv)	1979-11-27	1980-10-22	Forfarande for framstellning av aromatiska isocyanater genom karbonylering av nitroderivat i nervaro av zeoliter innehallande en aktiv metall

Country Status (12)

Country	Link
US (1)	US4332739A (fr)
JP (1)	JPS5687546A (fr)
BE (1)	BE886245A (fr)
CH (1)	CH645095A5 (fr)
DE (1)	DE3044156C2 (fr)
DK (1)	DK502680A (fr)
FR (1)	FR2470115A1 (fr)
GB (1)	GB2068939B (fr)
LU (1)	LU82952A1 (fr)
NL (1)	NL8006442A (fr)
NO (1)	NO151238C (fr)
SE (1)	SE448627B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11512046B2 (en)	2017-04-05	2022-11-29	Basf Se	Heterogeneous catalysts for the direct carbonylation of nitro aromatic compounds to isocyanates

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US3523966A (en) *	1966-04-01	1970-08-11	Olin Corp	Process for preparing aromatic isocyanates
GB1257932A (fr) *	1968-06-26	1971-12-22
US3828089A (en) *	1972-12-01	1974-08-06	Olin Corp	Preparation of aromatic isocyanates in fixed bed reactor
JPS5253999A (en) *	1975-10-29	1977-04-30	Sanyo Chem Ind Ltd	Metod for treating compositions containng free isocyanates
JPS5479251A (en) *	1977-12-08	1979-06-25	Mitsui Toatsu Chem Inc	Preparation of aromatic isocyanate

1979
- 1979-11-27 FR FR7929123A patent/FR2470115A1/fr active Granted
1980
- 1980-10-22 SE SE8007426A patent/SE448627B/sv not_active IP Right Cessation
- 1980-11-03 US US06/203,249 patent/US4332739A/en not_active Expired - Lifetime
- 1980-11-12 GB GB8036379A patent/GB2068939B/en not_active Expired
- 1980-11-19 NO NO803485A patent/NO151238C/no unknown
- 1980-11-19 BE BE0/202857A patent/BE886245A/fr not_active IP Right Cessation
- 1980-11-24 DE DE3044156A patent/DE3044156C2/de not_active Expired
- 1980-11-25 LU LU82952A patent/LU82952A1/fr unknown
- 1980-11-26 CH CH876180A patent/CH645095A5/fr not_active IP Right Cessation
- 1980-11-26 NL NL8006442A patent/NL8006442A/nl not_active Application Discontinuation
- 1980-11-26 DK DK502680A patent/DK502680A/da not_active Application Discontinuation
- 1980-11-27 JP JP16599280A patent/JPS5687546A/ja active Pending

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Publication number	Publication date
DE3044156C2 (de)	1982-08-26
LU82952A1 (fr)	1982-06-30
DE3044156A1 (de)	1981-06-19
GB2068939B (en)	1984-05-02
FR2470115B1 (fr)	1983-07-18
FR2470115A1 (fr)	1981-05-29
CH645095A5 (fr)	1984-09-14
JPS5687546A (en)	1981-07-16
NO803485L (no)	1981-05-29
NL8006442A (nl)	1981-07-01
NO151238B (no)	1984-11-26
GB2068939A (en)	1981-08-19
BE886245A (fr)	1981-05-19
SE8007426L (sv)	1981-05-28
DK502680A (da)	1981-05-28
US4332739A (en)	1982-06-01
NO151238C (no)	1985-03-06

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