NL7907149A - Werkwijze voor de carbonylering met groep viii edelmetaal-katalysatoren. - Google Patents

Werkwijze voor de carbonylering met groep viii edelmetaal-katalysatoren. Download PDF

Info

Publication number: NL7907149A
Authority: NL; Netherlands
Prior art keywords: carbonylation; catalyst; pressure; hydrogen; group viii
Prior art date: 1978-10-06

Application number

NL7907149A

Other languages

English (en)

Dutch (nl)

Original Assignee

Halcon Res & Dev

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.)

1978-10-06

Filing date

1979-09-26

Publication date

1980-04-09

1979-09-26 Application filed by Halcon Res & Dev filed Critical Halcon Res & Dev

1980-04-09 Publication of NL7907149A publication Critical patent/NL7907149A/nl

Links

239000003054 catalyst Substances 0.000 title claims description 73
238000005810 carbonylation reaction Methods 0.000 title claims description 44
230000006315 carbonylation Effects 0.000 title claims description 39
229910052751 metal Inorganic materials 0.000 title claims description 33
239000002184 metal Substances 0.000 title claims description 33
238000000034 method Methods 0.000 title claims description 22
230000036961 partial effect Effects 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 54
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 48
229910002091 carbon monoxide Inorganic materials 0.000 claims description 48
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 28
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 28
229910000510 noble metal Inorganic materials 0.000 claims description 27
230000008569 process Effects 0.000 claims description 15
239000010948 rhodium Substances 0.000 claims description 14
238000000926 separation method Methods 0.000 claims description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
229910052703 rhodium Inorganic materials 0.000 claims description 11
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 11
229910052763 palladium Inorganic materials 0.000 claims description 6
125000005907 alkyl ester group Chemical group 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims 1
239000000047 product Substances 0.000 claims 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 72
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
-1 acetic anhydride Chemical class 0.000 description 21
230000000694 effects Effects 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
239000007788 liquid Substances 0.000 description 12
239000011651 chromium Substances 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 9
229910052804 chromium Inorganic materials 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
238000007701 flash-distillation Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
150000002739 metals Chemical class 0.000 description 8
239000000203 mixture Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000000376 reactant Substances 0.000 description 7
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 6
GOKCJCODOLGYQD-UHFFFAOYSA-N 4,6-dichloro-2-imidazol-1-ylpyrimidine Chemical group ClC1=CC(Cl)=NC(N2C=NC=C2)=N1 GOKCJCODOLGYQD-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
229910052741 iridium Inorganic materials 0.000 description 5
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
238000011282 treatment Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
230000009849 deactivation Effects 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000001412 amines Chemical group 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
150000003949 imides Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002763 monocarboxylic acids Chemical class 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910017464 nitrogen compound Inorganic materials 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
229910052762 osmium Inorganic materials 0.000 description 2
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000010970 precious metal Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001292396 Cirrhitidae Species 0.000 description 1
USKHUHJZTHLYQK-UHFFFAOYSA-N ClP(C(=O)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound ClP(C(=O)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 USKHUHJZTHLYQK-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JTVHIRUDQBMPCB-UHFFFAOYSA-M O=C=[Rh](Cl)=C=O Chemical class O=C=[Rh](Cl)=C=O JTVHIRUDQBMPCB-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000005595 acetylacetonate group Chemical group 0.000 description 1
150000001255 actinides Chemical group 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
SZQABOJVTZVBHE-UHFFFAOYSA-N carbon monoxide;rhodium Chemical group [Rh].[Rh].[Rh].[Rh].[Rh].[Rh].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] SZQABOJVTZVBHE-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
230000008859 change Effects 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
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
125000005534 decanoate group Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
150000002835 noble gases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229920002717 polyvinylpyridine Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000012255 powdered metal Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
UGQZLDXDWSPAOM-UHFFFAOYSA-N pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone Chemical compound C1=C2C(=O)NC(=O)C2=CC2=C1C(=O)NC2=O UGQZLDXDWSPAOM-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
238000012827 research and development Methods 0.000 description 1
QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL7907149A 1978-10-06 1979-09-26 Werkwijze voor de carbonylering met groep viii edelmetaal-katalysatoren. NL7907149A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US94934478		1978-10-06
US05/949,344 US4252741A (en)	1978-10-06	1978-10-06	Carbonylation with Group VIII noble metal catalysts

Publications (1)

Publication Number	Publication Date
NL7907149A true NL7907149A (nl)	1980-04-09

Family

ID=25488946

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907149A NL7907149A (nl)	1978-10-06	1979-09-26	Werkwijze voor de carbonylering met groep viii edelmetaal-katalysatoren.

Country Status (8)

Country	Link
US (1)	US4252741A (fr)
JP (1)	JPS582216B2 (fr)
BE (1)	BE879236A (fr)
DE (1)	DE2940752C2 (fr)
FR (1)	FR2438023A1 (fr)
GB (2)	GB2033901B (fr)
IT (1)	IT1164052B (fr)
NL (1)	NL7907149A (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4358411A (en) *	1979-06-29	1982-11-09	The Halcon Sd Group, Inc.	Preparation of carbonylation products
JPS579733A (en) *	1980-06-18	1982-01-19	Mitsubishi Gas Chem Co Inc	Preparation of acetaldehyde
US4429150A (en)	1980-09-15	1984-01-31	Shell Oil Company	Manufacture of ethylidene diacetate
US4374070A (en) *	1980-11-21	1983-02-15	Eastman Kodak Company	Preparation of acetic anhydride
FR2496644A1 (fr) *	1980-12-24	1982-06-25	Rhone Poulenc Ind	Procede de preparation de l'anhydride acetique
JPS57134436A (en) *	1980-12-29	1982-08-19	Monsanto Co	Stabilization of carbonylation catalyst
DE3149094A1 (de) *	1981-12-11	1983-06-16	Hoechst Ag, 6230 Frankfurt	Verfahren zur entfernung von aceton aus reaktionsgemischen von carbonylierungsreaktionen
DE3149092A1 (de) *	1981-12-11	1983-06-16	Hoechst Ag, 6230 Frankfurt	Verfahren zur abtrennung des katalysatorsystems aus reaktionsgemischen von carbonylierungsreaktionen
JPS6016950A (ja) *	1983-07-08	1985-01-28	Daicel Chem Ind Ltd	カルボン酸無水物の製造法
JPS60199852A (ja) *	1984-03-22	1985-10-09	Daicel Chem Ind Ltd	アセチル化合物の製造方法
JPS60199853A (ja) *	1984-03-22	1985-10-09	Daicel Chem Ind Ltd	アセチル化合物の製造法
JPH066550B2 (ja) *	1984-03-23	1994-01-26	ダイセル化学工業株式会社	アセチル化合物の製法
US4578368A (en) *	1985-05-06	1986-03-25	Eastman Kodak Company	Catalyst recovery process
US4613623A (en) *	1985-07-23	1986-09-23	The United States Of America As Represented By The United States Department Of Energy	Low temperature synthesis of methyl formate
DE3811343A1 (de) *	1988-04-02	1989-10-19	Hoechst Ag	Verfahren zur herstellung von monocarbonsaeureanhydriden
GB9100216D0 (en) *	1991-01-05	1991-02-20	Bp Chem Int Ltd	Process
US5900504A (en) *	1996-02-20	1999-05-04	Eastman Chemical Company	Nickel-catalyzed carbonylation process
US5922911A (en) *	1998-04-24	1999-07-13	Eastman Chemical Company	Process for the manufacture of acetic anhydride
US6222070B1 (en)	1999-09-07	2001-04-24	Eastman Chemical Company	Method for reducing EDA in acetic anhydride production
DE60140958D1 (de) *	2001-02-13	2010-02-11	Eastman Chem Co	Verfahren zur reduzierung von eda bei der essigsäureanhydridproduktion
US7115772B2 (en) *	2002-01-11	2006-10-03	Celanese International Corporation	Integrated process for producing carbonylation acetic acid, acetic anhydride, or coproduction of each from a methyl acetate by-product stream
JP4526381B2 (ja) *	2004-12-27	2010-08-18	ダイセル化学工業株式会社	酢酸の製造方法
US7737298B2 (en) *	2006-06-09	2010-06-15	Eastman Chemical Company	Production of acetic acid and mixtures of acetic acid and acetic anhydride
US7582792B2 (en) *	2006-06-15	2009-09-01	Eastman Chemical Company	Carbonylation process
US7253304B1 (en)	2006-06-20	2007-08-07	Eastman Chemical Company	Carbonylation process
US7629491B2 (en) *	2006-06-26	2009-12-08	Eastman Chemical Company	Hydrocarboxylation process
US20090247783A1 (en) *	2008-04-01	2009-10-01	Eastman Chemical Company	Carbonylation process
EP2637998B1 (fr)	2010-11-12	2018-08-22	Eastman Chemical Company	Procédé pour le raffinage d'un mélange d'acétyles bruts
US9012683B2 (en)	2010-11-12	2015-04-21	Eastman Chemical Company	Coproduction of acetic acid and acetic anhydride
US10988432B2 (en)	2013-03-07	2021-04-27	Ineos Acetyls Uk Limited	Process for the co-production of acetic acid and acetic anhydride

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3852346A (en) *	1972-12-26	1974-12-03	Monsanto Co	Production of carboxylic acid anhydrides
US4115444A (en) *	1975-03-10	1978-09-19	Halcon International, Inc.	Process for preparing carboxylic acid anhydrides
CA1058636A (fr) *	1975-03-10	1979-07-17	Nabil Rizkalla	Procede pour la preparation d'anhydrides d'acides carboxyliques
US4002678A (en) *	1975-12-22	1977-01-11	Halcon International, Inc.	Preparation of carboxylic acid anhydrides
US4002677A (en) *	1975-12-22	1977-01-11	Halcon International, Inc.	Process for preparing carboxylic acid anhydrides

1978
- 1978-10-06 US US05/949,344 patent/US4252741A/en not_active Expired - Lifetime
1979
- 1979-09-26 NL NL7907149A patent/NL7907149A/nl not_active Application Discontinuation
- 1979-10-05 BE BE0/197502A patent/BE879236A/fr not_active IP Right Cessation
- 1979-10-05 GB GB7934674A patent/GB2033901B/en not_active Expired
- 1979-10-05 FR FR7924871A patent/FR2438023A1/fr active Granted
- 1979-10-05 IT IT50473/79A patent/IT1164052B/it active
- 1979-10-05 GB GB7934672A patent/GB2037276B/en not_active Expired
- 1979-10-06 JP JP54129360A patent/JPS582216B2/ja not_active Expired
- 1979-10-08 DE DE2940752A patent/DE2940752C2/de not_active Expired

Also Published As

Publication number	Publication date
IT1164052B (it)	1987-04-08
JPS5551036A (en)	1980-04-14
DE2940752A1 (de)	1980-04-17
IT7950473A0 (it)	1979-10-05
FR2438023B1 (fr)	1984-05-25
JPS582216B2 (ja)	1983-01-14
FR2438023A1 (fr)	1980-04-30
GB2037276B (en)	1983-02-09
GB2033901B (en)	1983-01-26
DE2940752C2 (de)	1982-11-25
US4252741A (en)	1981-02-24
GB2033901A (en)	1980-05-29
BE879236A (fr)	1980-04-08
GB2037276A (en)	1980-07-09

Legal Events

Date	Code	Title
1980-04-25	A1A	A request for search or an international-type search has been filed
1981-12-01	BB	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1985-07-01	BC	A request for examination has been filed
1988-05-02	BV	The patent application has lapsed

Publication	Publication Date	Title
US4252741A (en)	1981-02-24	Carbonylation with Group VIII noble metal catalysts
CA2345011C (fr)	2008-01-29	Carbonylation du methanol en presence d'un systeme catalytique rhodium/iridium/ion iodure
CA2060052C (fr)	2003-01-07	Extraction d'impuretes du type carbonyle dans les produits d'un procede de carboxylation
US4358411A (en)	1982-11-09	Preparation of carbonylation products
CA1058636A (fr)	1979-07-17	Procede pour la preparation d'anhydrides d'acides carboxyliques
JPS6230179B2 (fr)	1987-07-01
JPS62298549A (ja)	1987-12-25	メタノ−ルのカルボニル化による酢酸の製造における一酸化炭素供給ガスへの水素の添加
AU6527700A (en)	2001-03-26	Rhodium/inorganic iodide catalyst system for methanol carbonylation process with improved impurity profile
NL8105841A (nl)	1982-07-16	Werkwijze voor het bereiden van een carbonzuur.
JPH10175910A (ja)	1998-06-30	シクロヘキサンの酸化から得られる反応混合物を処理する方法
NL7908842A (nl)	1980-07-01	Werkwijze voor de winning van door carbonylering verkregen aceton.
US4241219A (en)	1980-12-23	Treatment of carbonylation effluent
JP3384501B2 (ja)	2003-03-10	共役ジエンのカルボニル化
NL8105842A (nl)	1982-07-16	Werkwijze voor het bereiden van een carbonzuuranhydride.
NL8006806A (nl)	1981-07-16	Werkwijze ter bereiding van azijnzuuranhydride.
NL8005234A (nl)	1981-04-06	Werkwijze voor de bereiding van een anhydride van een monocarbonzuur.
EP0556806B1 (fr)	1996-05-29	Procédé de préparation de dianhydrides biphényltétracarboxyliques
NL8202192A (nl)	1982-12-16	Werkwijze voor de bereiding van carbonzuuresters.
NL8006807A (nl)	1981-07-16	Werkwijze ter bereiding van azijnzuuranhydride.
NL8105843A (nl)	1982-07-16	Werkwijze voor het bereiden van ethylideendiacetaat.
NL7907086A (nl)	1980-04-09	Werkwijze voor de dehydratatie van methylacetaat.
NL8104231A (nl)	1982-04-16	Werkwijze voor het bereiden van aceetaldehyd.
NL7908980A (nl)	1980-07-01	Werkwijze voor het bereiden van aceetaldehyde.
JPS62209032A (ja)	1987-09-14	一価アルコ−ルの製造方法
EP1360165B1 (fr)	2009-12-30	Procede de reduction de l'ethylidene diacetate dans la production d'anhydride acetique