NL8004207A - Werkwijze voor het carbonyleren van esters en/of ethers. - Google Patents

Werkwijze voor het carbonyleren van esters en/of ethers. Download PDF

Info

Publication number: NL8004207A
Authority: NL; Netherlands
Prior art keywords: carbonylation; zone; components; reaction; methyl acetate
Prior art date: 1979-07-30

Application number

NL8004207A

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.)

1979-07-30

Filing date

1980-07-22

Publication date

1981-02-03

1980-07-22 Application filed by Halcon Res & Dev filed Critical Halcon Res & Dev

1981-02-03 Publication of NL8004207A publication Critical patent/NL8004207A/nl

Links

238000000034 method Methods 0.000 title claims description 28
150000002170 ethers Chemical class 0.000 title description 3
238000005810 carbonylation reaction Methods 0.000 claims description 71
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 68
230000006315 carbonylation Effects 0.000 claims description 53
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 40
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 35
150000002367 halogens Chemical class 0.000 claims description 35
229910052751 metal Inorganic materials 0.000 claims description 29
239000002184 metal Substances 0.000 claims description 29
238000005406 washing Methods 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 18
238000009835 boiling Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 3
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims 1
150000004075 acetic anhydrides Chemical class 0.000 claims 1
239000007789 gas Substances 0.000 description 43
239000007788 liquid Substances 0.000 description 34
239000003054 catalyst Substances 0.000 description 29
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 23
229910002091 carbon monoxide Inorganic materials 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 23
-1 acetic anhydride Chemical class 0.000 description 17
229910052739 hydrogen Inorganic materials 0.000 description 17
239000001257 hydrogen Substances 0.000 description 17
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 17
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 15
229910052740 iodine Inorganic materials 0.000 description 15
239000011630 iodine Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
150000004820 halides Chemical class 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
229910000510 noble metal Inorganic materials 0.000 description 11
239000000470 constituent Substances 0.000 description 8
150000002739 metals Chemical class 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
238000000926 separation method Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
229910052703 rhodium Inorganic materials 0.000 description 7
239000010948 rhodium Substances 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
125000004432 carbon atom Chemical group C* 0.000 description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000011651 chromium Substances 0.000 description 4
229910052741 iridium Inorganic materials 0.000 description 4
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
229910052783 alkali metal Inorganic materials 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
150000002736 metal compounds Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000002897 organic nitrogen compounds Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002090 carbon oxide Inorganic materials 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000446 fuel Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 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
239000007791 liquid phase Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
150000002903 organophosphorus compounds Chemical class 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
239000012071 phase Substances 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
239000002243 precursor Substances 0.000 description 2
238000010926 purge Methods 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
230000035484 reaction time Effects 0.000 description 2
SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-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
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
BOGVTNYNTGOONP-UHFFFAOYSA-N 3,4-dihydroxyoxolane-2,5-dione Chemical compound OC1C(O)C(=O)OC1=O BOGVTNYNTGOONP-UHFFFAOYSA-N 0.000 description 1
241000534000 Berula erecta Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
235000002918 Fraxinus excelsior Nutrition 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-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
YWHYLYDGWQNMND-UHFFFAOYSA-N [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(Cl)(C=1C=CC=CC=1)C(=O)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(Cl)(C=1C=CC=CC=1)C(=O)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YWHYLYDGWQNMND-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000005595 acetylacetonate group Chemical group 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001255 actinides Chemical group 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 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
125000003368 amide group Chemical group 0.000 description 1
150000001412 amines Chemical group 0.000 description 1
239000002956 ash Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 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
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229920002301 cellulose acetate Polymers 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
238000010924 continuous production Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000013016 damping Methods 0.000 description 1
125000005534 decanoate group Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
229910000071 diazene Inorganic materials 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
239000000945 filler Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 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
150000004678 hydrides Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
KQDHKDQCZVWIEV-UHFFFAOYSA-N isoindole-1,3-dione;pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1.C1=CC=C2C(=O)NC(=O)C2=C1 KQDHKDQCZVWIEV-UHFFFAOYSA-N 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
150000002763 monocarboxylic acids 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
125000001477 organic nitrogen group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
238000012856 packing Methods 0.000 description 1
GJYLBGHKIMDUIH-UHFFFAOYSA-N pentane-2,4-dione;rhodium Chemical compound [Rh].CC(=O)CC(C)=O GJYLBGHKIMDUIH-UHFFFAOYSA-N 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
229920000642 polymer Polymers 0.000 description 1
229920002717 polyvinylpyridine Polymers 0.000 description 1
239000012255 powdered metal Substances 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
238000011084 recovery Methods 0.000 description 1
238000004064 recycling 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
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000013589 supplement Substances 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
TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 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
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 1
239000012808 vapor phase Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000002699 waste material Substances 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
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
- 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

Landscapes

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

NL8004207A 1979-07-30 1980-07-22 Werkwijze voor het carbonyleren van esters en/of ethers. NL8004207A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/061,712 US4241219A (en)	1979-07-30	1979-07-30	Treatment of carbonylation effluent
US6171279		1979-07-30

Publications (1)

Publication Number	Publication Date
NL8004207A true NL8004207A (nl)	1981-02-03

Family

ID=22037610

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004207A NL8004207A (nl)	1979-07-30	1980-07-22	Werkwijze voor het carbonyleren van esters en/of ethers.

Country Status (9)

Country	Link
US (1)	US4241219A (fr)
JP (1)	JPS5622746A (fr)
BE (1)	BE884537A (fr)
DE (1)	DE3028934C2 (fr)
FR (1)	FR2462413B1 (fr)
GB (1)	GB2055830B (fr)
IT (1)	IT1128546B (fr)
MX (1)	MX155402A (fr)
NL (1)	NL8004207A (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5643241A (en) *	1979-09-13	1981-04-21	Mitsubishi Gas Chem Co Inc	Preparation of ethylidene diacetate
FR2489817A1 (fr) *	1980-09-11	1982-03-12	Rhone Poulenc Ind	Procede de preparation d'anhydrides d'acides carboxyliques par carbonylation
DE3107731A1 (de) *	1981-02-28	1982-09-16	Basf Ag, 6700 Ludwigshafen	Verfahren zur abtrennung organischer jod-verbindungen von carbonylierungsprodukten des methanols, methylacetates und dimethylethers
US4434240A (en)	1981-11-16	1984-02-28	The Halcon Sd Group, Inc.	Recovery of noble metal values from carbonylation residues
US4664851A (en) *	1981-12-30	1987-05-12	Shell Oil Company	Process for the co-production of carboxylic acids and carboxylic acid esters
US4434241A (en)	1982-09-27	1984-02-28	Eastman Kodak Company	Catalyst recovery process from tar from carbonylation reactions
CA1228867A (fr) *	1984-05-03	1987-11-03	Celanese Corporation	Carbonylation du methanol
RU2173314C2 (ru) *	1995-08-22	2001-09-10	Бп Кемикэлз Лимитед	Способ карбонилирования спирта и/или его реакционноспособного производного
EP2327474B1 (fr) *	2008-04-29	2018-01-10	Celanese International Corporation	Système de carbonylation de méthanol disposant d'un absorbeur à plusieurs options de solvants
BR112013011566A2 (pt) *	2010-11-12	2016-08-09	Eastman Chem Co	método para recuperar compostos contendo iodo
CA2951575A1 (fr)	2014-06-17	2015-12-23	Bp Chemicals Limited	Procede et appareil pour le traitement de degagement gazeux dans une unite de production d'acide acetique
WO2016194850A1 (fr) *	2015-06-01	2016-12-08	株式会社ダイセル	Procédé de production d'acide acétique
US20230127564A1 (en)	2020-04-01	2023-04-27	Celanese International Corporation	Processes for removing and/or reducing permanganate reducing compounds and alkyl iodides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE791577A (fr) *	1971-11-19	1973-05-17	Monsanto Co	Purification de courants d'acide carboxylique
BE793203A (fr) *	1971-12-27	1973-06-22	Monsanto Co	Production d'acides carboxyliques
US4121978A (en) *	1973-01-30	1978-10-24	Rhone-Progil	Method of separating chlorinated aliphatic hydrocarbons from mixtures thereof, by extractive distillation
US3887595A (en) *	1973-03-05	1975-06-03	Shell Oil Co	Carbonylation process
US4115444A (en) *	1975-03-10	1978-09-19	Halcon International, Inc.	Process for preparing carboxylic acid anhydrides
US4134912A (en) *	1976-11-08	1979-01-16	Halcon International, Inc.	Process for preparing carboxylic acids

1979
- 1979-07-30 US US06/061,712 patent/US4241219A/en not_active Expired - Lifetime
1980
- 1980-07-22 NL NL8004207A patent/NL8004207A/nl not_active Application Discontinuation
- 1980-07-25 IT IT49334/80A patent/IT1128546B/it active
- 1980-07-29 FR FR8016740A patent/FR2462413B1/fr not_active Expired
- 1980-07-29 BE BE0/201578A patent/BE884537A/fr not_active IP Right Cessation
- 1980-07-30 DE DE3028934A patent/DE3028934C2/de not_active Expired
- 1980-07-30 JP JP10493780A patent/JPS5622746A/ja active Pending
- 1980-07-30 MX MX183371A patent/MX155402A/es unknown
- 1980-07-30 GB GB8024910A patent/GB2055830B/en not_active Expired

Also Published As

Publication number	Publication date
BE884537A (fr)	1981-01-29
IT8049334A0 (it)	1980-07-25
DE3028934A1 (de)	1981-02-19
FR2462413B1 (fr)	1986-10-24
US4241219A (en)	1980-12-23
FR2462413A1 (fr)	1981-02-13
DE3028934C2 (de)	1984-01-19
MX155402A (es)	1988-02-29
GB2055830A (en)	1981-03-11
JPS5622746A (en)	1981-03-03
IT1128546B (it)	1986-05-28
GB2055830B (en)	1983-09-14

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1985-07-01	BA	A request for search or an international-type search has been filed
1985-08-01	BB	A search report has been drawn up
1985-08-01	BC	A request for examination has been filed
1988-03-01	BV	The patent application has lapsed

Publication	Publication Date	Title
AU647314B2 (en)	1994-03-17	Process for the purification of carboxylic acids and/or their anhydrides
KR0144154B1 (ko)	1998-07-15	아세트산 및 아세트산 무수물의 제조방법
KR100495554B1 (ko)	2005-06-16	카보닐화 공정 스트림으로부터 과망간산염 환원 화합물 및 알킬요오다이드를 제거하는 방법
EP1720821B1 (fr)	2018-12-26	Elimination des composes reducteurs de permanganate dans les circuits de carbonylation de methanol
AU2005222058B2 (en)	2011-08-18	Removal of permanganate reducing compounds from methanol carbonylation process stream
US4358411A (en)	1982-11-09	Preparation of carbonylation products
NL8004207A (nl)	1981-02-03	Werkwijze voor het carbonyleren van esters en/of ethers.
NZ585014A (en)	2011-11-25	Acetaldehyde removal from methyl acetate by distillation at elevated pressure
UA61078C2 (uk)	2003-11-17	Спосіб одержання оцтової кислоти безводним карбонілюванням
US5364822A (en)	1994-11-15	Process for the recovery of group VIII noble metals
US5834615A (en)	1998-11-10	Process for producing diaryl carbonate
JPS6247862B2 (fr)	1987-10-09
KR100206728B1 (ko)	1999-07-01	아세트산 및 물을 함유하는 조성물로 부터 아세트산의 회수방법
JP3581725B2 (ja)	2004-10-27	アセトアルデヒドとヨウ化メチルの分離方法
RU2235087C2 (ru)	2004-08-27	Способ получения уксусной кислоты и/или метилацетата и способ улучшения стабильности и/или предотвращения дезактивации катализатора при получении уксусной кислоты и/или метилацетата
JPS6318927B2 (fr)	1988-04-20
JPH07324055A (ja)	1995-12-12	無水酢酸及び酢酸の製造法
NL8104231A (nl)	1982-04-16	Werkwijze voor het bereiden van aceetaldehyd.
JPH11279116A (ja)	1999-10-12	シュウ酸ジアルキルの製造法
JP4022955B2 (ja)	2007-12-19	炭酸ジアリールエステルの製造法
US4227010A (en)	1980-10-07	Recovery of dimethyl terephthalate and intermediates from the tarry fraction of cooxidation process residue
JPH0358355B2 (fr)	1991-09-05
JPH11246490A (ja)	1999-09-14	炭酸ジアリールの製造法