ZA200102081B - Process for purification of alkyl alkanoate. - Google Patents
Process for purification of alkyl alkanoate. Download PDFInfo
- Publication number
- ZA200102081B ZA200102081B ZA200102081A ZA200102081A ZA200102081B ZA 200102081 B ZA200102081 B ZA 200102081B ZA 200102081 A ZA200102081 A ZA 200102081A ZA 200102081 A ZA200102081 A ZA 200102081A ZA 200102081 B ZA200102081 B ZA 200102081B
- Authority
- ZA
- South Africa
- Prior art keywords
- process according
- ethanol
- ethyl acetate
- bar
- distillation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 69
- 125000000217 alkyl group Chemical group 0.000 title claims description 61
- 230000008569 process Effects 0.000 title claims description 55
- 238000000746 purification Methods 0.000 title claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 271
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 256
- 238000004821 distillation Methods 0.000 claims description 86
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 238000005984 hydrogenation reaction Methods 0.000 claims description 37
- 239000000047 product Substances 0.000 claims description 34
- 239000007795 chemical reaction product Substances 0.000 claims description 32
- 239000012535 impurity Substances 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001299 aldehydes Chemical class 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000005751 Copper oxide Substances 0.000 claims description 6
- 229910000431 copper oxide Inorganic materials 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052774 Proactinium Inorganic materials 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000895 extractive distillation Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 14
- 239000007789 gas Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- -1 for example Substances 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 1
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102100038509 E3 ubiquitin-protein ligase ARIH1 Human genes 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OUGPMNMLWKSBRI-UHFFFAOYSA-N Hexyl formate Chemical compound CCCCCCOC=O OUGPMNMLWKSBRI-UHFFFAOYSA-N 0.000 description 1
- 101000808922 Homo sapiens E3 ubiquitin-protein ligase ARIH1 Proteins 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 101000800755 Naja oxiana Alpha-elapitoxin-Nno2a Proteins 0.000 description 1
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 1
- KFNNIILCVOLYIR-UHFFFAOYSA-N Propyl formate Chemical compound CCCOC=O KFNNIILCVOLYIR-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- WZECUPJJEIXUKY-UHFFFAOYSA-N [O-2].[O-2].[O-2].[U+6] Chemical compound [O-2].[O-2].[O-2].[U+6] WZECUPJJEIXUKY-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- DKSMCEUSSQTGBK-UHFFFAOYSA-N bromous acid Chemical compound OBr=O DKSMCEUSSQTGBK-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical group [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910000439 uranium oxide Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98308013A EP0992484A1 (fr) | 1998-10-01 | 1998-10-01 | Procédé |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200102081B true ZA200102081B (en) | 2002-08-13 |
Family
ID=8235087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200102081A ZA200102081B (en) | 1998-10-01 | 1999-09-29 | Process for purification of alkyl alkanoate. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6632330B1 (fr) |
| EP (2) | EP0992484A1 (fr) |
| JP (1) | JP4889859B2 (fr) |
| KR (1) | KR100581371B1 (fr) |
| AU (1) | AU6107199A (fr) |
| BR (1) | BR9914248B1 (fr) |
| CA (1) | CA2345983C (fr) |
| ES (1) | ES2276533T3 (fr) |
| GB (1) | GB2357503B (fr) |
| TW (1) | TWI239951B (fr) |
| WO (1) | WO2000020374A1 (fr) |
| ZA (1) | ZA200102081B (fr) |
Families Citing this family (122)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0990638A1 (fr) | 1998-10-01 | 2000-04-05 | Kvaerner Process Technology Limited | Procédé |
| EP0992482A1 (fr) * | 1998-10-01 | 2000-04-12 | Kvaerner Process Technology Limited | Procédé |
| GB0019245D0 (en) * | 2000-08-04 | 2000-09-27 | Bp Chem Int Ltd | Process for removing a ketone and/or aldehyde impurity |
| US7699961B2 (en) * | 2001-10-19 | 2010-04-20 | Mitsubishi Chemical Corporation | Apparatus for concentrating water-soluble organic material |
| JP5486299B2 (ja) * | 2006-04-14 | 2014-05-07 | セラニーズ・インターナショナル・コーポレーション | 標的ストリーム中のアルデヒド濃度の低減法 |
| CN101148407B (zh) * | 2007-10-16 | 2010-04-14 | 南京师范大学 | 连续侧线出料法提取酮康唑生产中乙酸乙酯的方法 |
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| CN102811990B (zh) * | 2010-08-06 | 2015-05-27 | 国际人造丝公司 | 用于与汽油或柴油燃料调合用作发动机燃料的变性燃料乙醇组合物 |
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| US9024089B2 (en) | 2011-11-18 | 2015-05-05 | Celanese International Corporation | Esterification process using extractive separation to produce feed for hydrogenolysis |
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| EP2782890A1 (fr) | 2011-11-22 | 2014-10-01 | Celanese International Corporation | Estérification d'un mélange d'éthanol et d'acide acétique pour produire une charge d'ester pour l'hydrogénolyse |
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| US9233899B2 (en) | 2011-12-22 | 2016-01-12 | Celanese International Corporation | Hydrogenation catalysts having an amorphous support |
| US8575406B2 (en) | 2011-12-22 | 2013-11-05 | Celanese International Corporation | Catalysts having promoter metals and process for producing ethanol |
| US9000234B2 (en) | 2011-12-22 | 2015-04-07 | Celanese International Corporation | Calcination of modified support to prepare hydrogenation catalysts |
| US8907139B2 (en) | 2011-12-28 | 2014-12-09 | Celanese International Corporation | Process for acetal removal in the purification of a crude ethanol product |
| US9333496B2 (en) | 2012-02-29 | 2016-05-10 | Celanese International Corporation | Cobalt/tin catalyst for producing ethanol |
| US9079172B2 (en) | 2012-03-13 | 2015-07-14 | Celanese International Corporation | Promoters for cobalt-tin catalysts for reducing alkanoic acids |
| US8455702B1 (en) | 2011-12-29 | 2013-06-04 | Celanese International Corporation | Cobalt and tin catalysts for producing ethanol |
| US8802902B2 (en) | 2011-12-30 | 2014-08-12 | Celanese International Corporation | Pressure driven distillation for ethanol production and recovery from hydrogenation process |
| WO2013103399A1 (fr) | 2012-01-06 | 2013-07-11 | Celanese International Corporation | Catalyseurs d'hydrogénation à supports modifiés au cobalt |
| US9024086B2 (en) | 2012-01-06 | 2015-05-05 | Celanese International Corporation | Hydrogenation catalysts with acidic sites |
| US8802588B2 (en) | 2012-01-23 | 2014-08-12 | Celanese International Corporation | Bismuth catalyst composition and process for manufacturing ethanol mixture |
| US9079851B2 (en) | 2012-02-01 | 2015-07-14 | Greenyug, Llc | Ethyl acetate production |
| US8729311B2 (en) | 2012-02-10 | 2014-05-20 | Celanese International Corporaton | Catalysts for converting acetic acid to acetone |
| US9050585B2 (en) | 2012-02-10 | 2015-06-09 | Celanese International Corporation | Chemisorption of ethyl acetate during hydrogenation of acetic acid to ethanol |
| US9126194B2 (en) | 2012-02-29 | 2015-09-08 | Celanese International Corporation | Catalyst having support containing tin and process for manufacturing ethanol |
| US8802903B2 (en) | 2012-03-13 | 2014-08-12 | Celanese International Corporation | Stacked bed reactor with diluents for producing ethanol |
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| US9073042B2 (en) | 2012-03-14 | 2015-07-07 | Celanese International Corporation | Acetic acid hydrogenation over a group VIII metal calcined catalyst having a secondary promoter |
| US8536383B1 (en) | 2012-03-14 | 2013-09-17 | Celanese International Corporation | Rhodium/tin catalysts and processes for producing ethanol |
| US8975452B2 (en) | 2012-03-28 | 2015-03-10 | Celanese International Corporation | Process for producing ethanol by hydrocarbon oxidation and hydrogenation or hydration |
| US8772553B2 (en) | 2012-10-26 | 2014-07-08 | Celanese International Corporation | Hydrogenation reaction conditions for producing ethanol |
| US8957262B2 (en) | 2012-11-20 | 2015-02-17 | Celanese International Corporation | Olefin hydration for hydrogenation processes |
| US9000237B2 (en) | 2012-12-20 | 2015-04-07 | Celanese International Corporation | Ethanol refining process using intermediate reboiler |
| EP2958881A4 (fr) | 2013-02-19 | 2016-12-21 | Greenyug Llc | Production d'alcools supérieurs |
| US8975451B2 (en) | 2013-03-15 | 2015-03-10 | Celanese International Corporation | Single phase ester feed for hydrogenolysis |
| US8926718B2 (en) | 2013-03-15 | 2015-01-06 | Celanese International Corporation | Thermochemically produced ethanol compositions |
| US20150075062A1 (en) * | 2013-09-13 | 2015-03-19 | Ineos Bio Sa | Alcohol compositions and a process for their production |
| US10081588B2 (en) | 2013-12-04 | 2018-09-25 | Rescurve, Llc | Production of butyl acetate from ethanol |
| US10293304B2 (en) | 2015-07-14 | 2019-05-21 | John E. Stauffer | Carbon dioxide recovery using an absorption column in combination with osmotic filters |
| US10040737B2 (en) | 2015-07-14 | 2018-08-07 | John E. Stauffer | Methanol production from methane and carbon dioxide |
| US10493397B2 (en) | 2015-07-14 | 2019-12-03 | John E. Stauffer | Carbon dioxide recovery |
| CA2994846C (fr) | 2015-08-19 | 2024-02-20 | Rescurve, Llc | Composition de catalyseurs pour la conversion d'ethanol en n-butanol et alcools a haut poids moleculaire |
| CN112079704B (zh) * | 2020-10-15 | 2022-09-13 | 苏州亚科科技股份有限公司 | 一种丁酸丁酯的制备方法及丁酸 |
| GB202208864D0 (en) | 2022-06-16 | 2022-08-10 | Johnson Matthey Davy Technologies Ltd | Process for the recovery of ethanol from crude ethyl acetate |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524899A (en) | 1946-02-08 | 1950-10-10 | Union Carbide & Carbon Corp | Purification of fatty acid esters |
| JPS5163117A (en) * | 1974-11-29 | 1976-06-01 | Mitsui Petrochemical Ind | Gisanmechiruno seizohoho |
| NL8003405A (nl) * | 1980-06-12 | 1982-01-04 | Shell Int Research | Werkwijze voor het bereiden van ethanol. |
| ZA816748B (en) * | 1980-10-01 | 1982-10-27 | Hoechst Ag | Process for the preparation of an ethyl ester |
| US4379028A (en) * | 1982-03-30 | 1983-04-05 | Lloyd Berg | Separation of ethyl acetate from ethanol and water by extractive distillation |
| DE3228500A1 (de) * | 1982-07-30 | 1984-02-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur reinigung von aldehyde, acetale und/oder ungesaettigte verbindungen enthaltenden carbonsaeureestern |
| GB8400785D0 (en) * | 1984-01-12 | 1984-02-15 | Davy Mckee Ltd | Process |
| US4569726A (en) * | 1984-07-19 | 1986-02-11 | Lloyd Berg | Process for the separation of ethyl acetate from ethanol and water by extractive distillation |
| CA1281739C (fr) * | 1985-05-10 | 1991-03-19 | Brian T. Keen | Methode pour la conversion d'alcanols primaires en leurs esters |
| US4613701A (en) * | 1985-09-19 | 1986-09-23 | Celanese Corporation | Recovery of rhodium from hydroformylation reaction product |
| DE3806304A1 (de) * | 1988-02-27 | 1989-09-07 | Basf Ag | Verfahren zur reinigung von aldehyde, acetale und/oder ungesaettigte verbindungen enthaltenden carbonsaeureestern |
| JP3160983B2 (ja) * | 1992-01-10 | 2001-04-25 | 昭和電工株式会社 | 酢酸エチルの精製方法 |
| DE4339977A1 (de) * | 1993-11-24 | 1995-06-01 | Bayer Ag | Verfahren zur Aufarbeitung der flüssigen Reaktionsprodukte aus der Cu-katalysierten Dimethylcarbonatherstellung |
| EP0990638A1 (fr) * | 1998-10-01 | 2000-04-05 | Kvaerner Process Technology Limited | Procédé |
| EP0992482A1 (fr) * | 1998-10-01 | 2000-04-12 | Kvaerner Process Technology Limited | Procédé |
-
1998
- 1998-10-01 EP EP98308013A patent/EP0992484A1/fr not_active Withdrawn
-
1999
- 1999-09-23 TW TW088116386A patent/TWI239951B/zh not_active IP Right Cessation
- 1999-09-29 KR KR1020017004052A patent/KR100581371B1/ko not_active IP Right Cessation
- 1999-09-29 AU AU61071/99A patent/AU6107199A/en not_active Abandoned
- 1999-09-29 BR BRPI9914248-1A patent/BR9914248B1/pt not_active IP Right Cessation
- 1999-09-29 JP JP2000574492A patent/JP4889859B2/ja not_active Expired - Fee Related
- 1999-09-29 GB GB0106309A patent/GB2357503B/en not_active Expired - Fee Related
- 1999-09-29 EP EP99947694A patent/EP1117630B1/fr not_active Expired - Lifetime
- 1999-09-29 ES ES99947694T patent/ES2276533T3/es not_active Expired - Lifetime
- 1999-09-29 US US09/806,112 patent/US6632330B1/en not_active Expired - Lifetime
- 1999-09-29 ZA ZA200102081A patent/ZA200102081B/en unknown
- 1999-09-29 WO PCT/GB1999/003228 patent/WO2000020374A1/fr active IP Right Grant
- 1999-09-29 CA CA002345983A patent/CA2345983C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TWI239951B (en) | 2005-09-21 |
| EP1117630B1 (fr) | 2006-11-02 |
| GB2357503B (en) | 2003-11-12 |
| KR20010075477A (ko) | 2001-08-09 |
| WO2000020374A1 (fr) | 2000-04-13 |
| ES2276533T3 (es) | 2007-06-16 |
| EP0992484A1 (fr) | 2000-04-12 |
| CA2345983A1 (fr) | 2000-04-13 |
| GB2357503A (en) | 2001-06-27 |
| CA2345983C (fr) | 2008-01-29 |
| KR100581371B1 (ko) | 2006-05-23 |
| AU6107199A (en) | 2000-04-26 |
| BR9914248B1 (pt) | 2010-09-21 |
| GB0106309D0 (en) | 2001-05-02 |
| BR9914248A (pt) | 2001-12-04 |
| JP4889859B2 (ja) | 2012-03-07 |
| EP1117630A1 (fr) | 2001-07-25 |
| JP2002526519A (ja) | 2002-08-20 |
| US6632330B1 (en) | 2003-10-14 |
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