CA1229096A - Procede d'hydrogenolyse des esters d'acides carboxyliques - Google Patents
Procede d'hydrogenolyse des esters d'acides carboxyliquesInfo
- Publication number
- CA1229096A CA1229096A CA000401903A CA401903A CA1229096A CA 1229096 A CA1229096 A CA 1229096A CA 000401903 A CA000401903 A CA 000401903A CA 401903 A CA401903 A CA 401903A CA 1229096 A CA1229096 A CA 1229096A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- process according
- mixture
- percent
- kpa
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 54
- 238000007327 hydrogenolysis reaction Methods 0.000 title abstract description 25
- 150000001733 carboxylic acid esters Chemical class 0.000 title abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 79
- 239000000203 mixture Substances 0.000 claims abstract description 75
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims abstract description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000011787 zinc oxide Substances 0.000 claims abstract description 32
- 239000005751 Copper oxide Substances 0.000 claims abstract description 16
- 229910000431 copper oxide Inorganic materials 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 97
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 239000007789 gas Substances 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- -1 aliphatic monocarboxylic acid Chemical class 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 25
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical group CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 14
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- 238000010924 continuous production Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical class CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 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 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 2
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 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
- 239000004615 ingredient Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000003901 oxalic acid esters Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OUCGJMIVSYHBEC-UHFFFAOYSA-N 2-ethylhexyl 2-ethylhexanoate Chemical compound CCCCC(CC)COC(=O)C(CC)CCCC OUCGJMIVSYHBEC-UHFFFAOYSA-N 0.000 description 1
- UKCLWLHLRSZLQC-UHFFFAOYSA-N 2-methoxyethyl 2-methoxyacetate Chemical compound COCCOC(=O)COC UKCLWLHLRSZLQC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910017518 Cu Zn Inorganic materials 0.000 description 1
- 229910017752 Cu-Zn Inorganic materials 0.000 description 1
- 229910017943 Cu—Zn Inorganic materials 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 101100229907 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GPP2 gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CXQXWHWPDDUDPI-UHFFFAOYSA-N [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O Chemical compound [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O CXQXWHWPDDUDPI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000005605 isobutyric acids Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25873381A | 1981-04-29 | 1981-04-29 | |
| US258,733 | 1981-04-29 | ||
| GB8203701 | 1982-02-09 | ||
| GB8203701 | 1982-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1229096A true CA1229096A (fr) | 1987-11-10 |
Family
ID=26281940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000401903A Expired CA1229096A (fr) | 1981-04-29 | 1982-04-28 | Procede d'hydrogenolyse des esters d'acides carboxyliques |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS58500993A (fr) |
| AU (1) | AU560590B2 (fr) |
| BR (1) | BR8207962A (fr) |
| CA (1) | CA1229096A (fr) |
| FI (1) | FI831848L (fr) |
| GB (1) | GB2116552B (fr) |
| IT (1) | IT1190783B (fr) |
| MX (1) | MX156577A (fr) |
| NL (1) | NL191438C (fr) |
| NO (1) | NO824396L (fr) |
| NZ (1) | NZ200442A (fr) |
| SE (1) | SE452154B (fr) |
| WO (1) | WO1982003854A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102076646A (zh) * | 2009-04-07 | 2011-05-25 | 戴维加工技术有限公司 | 具有第一碳链长度的脂肪醇流和具有第二碳链长度的脂肪醇流的联合生产方法 |
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3363702D1 (en) * | 1982-03-26 | 1986-07-03 | Davy Mckee London | Process for the production of ethanol |
| US4588848A (en) * | 1984-11-01 | 1986-05-13 | Air Products And Chemicals, Inc. | Synthesis of neoalkanols |
| US4593147A (en) * | 1984-11-01 | 1986-06-03 | Air Products And Chemicals, Inc. | Synthesis of neoalkanes |
| DE3510883A1 (de) * | 1985-03-26 | 1986-10-09 | Kali-Chemie Ag, 3000 Hannover | Verfahren zur herstellung von 2.2.2.-trifluoraethanol |
| US4652685A (en) * | 1985-11-15 | 1987-03-24 | General Electric Company | Hydrogenation of lactones to glycols |
| US4837368A (en) * | 1988-02-01 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds and supported catalysts therefor |
| US4837367A (en) * | 1987-08-03 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds |
| US4810807A (en) * | 1987-10-13 | 1989-03-07 | The Standard Oil Company | Hydrogenation of maleic anhydride to tetrahydrofuran |
| JP2772524B2 (ja) * | 1988-07-15 | 1998-07-02 | 東燃株式会社 | １，４‐ブタンジオールの製造方法 |
| ES2064715T3 (es) * | 1989-01-17 | 1995-02-01 | Davy Mckee London | Procedimiento para la obtencion de alcoholes grasos. |
| GB8917862D0 (en) * | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| DE3930288A1 (de) * | 1989-09-11 | 1991-03-21 | Henkel Kgaa | Kupfer-silikat-katalysator, sein herstellungsverfahren und seine verwendung |
| CA2026275C (fr) * | 1989-10-17 | 2000-12-05 | Deepak S. Thakur | Catalyseur d'hydrogenation, methode de preparation et methode d'utilisation connexes |
| JP2595358B2 (ja) * | 1989-12-07 | 1997-04-02 | 東燃株式会社 | １，４―ブタンジオールおよびテトラヒドロフランの製造方法 |
| GB9025708D0 (en) * | 1990-11-27 | 1991-01-09 | Unilever Plc | Fatty ester hydrogenation |
| DE4141220A1 (de) * | 1991-12-13 | 1993-06-17 | Basf Ag | Verfahren zur herstellung von primaeren alkoholen |
| DE4142899A1 (de) * | 1991-12-23 | 1993-06-24 | Sued Chemie Ag | Verfahren zur herstellung von alkoholen durch katalytische hydrierung von carbonsaeurealkylestern |
| DE4206750A1 (de) * | 1992-03-04 | 1993-09-09 | Hoechst Ag | Verfahren zur herstellung von alkoholen oder aminen |
| DE4233431A1 (de) * | 1992-10-05 | 1994-04-07 | Basf Ag | Verfahren zur Hydrierung von Zitronensäure |
| US5334779A (en) * | 1993-06-01 | 1994-08-02 | Eastman Kodak Company | Catalyst compositions and the use thereof in the hydrogenation of carboxylic acid esters |
| WO1995010497A1 (fr) * | 1993-10-08 | 1995-04-20 | Ube Industries, Ltd. | Procede de production d'un diol |
| GB9324823D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324784D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324782D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324752D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324753D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324785D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324786D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324783D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| DE4431220A1 (de) * | 1994-09-02 | 1996-03-07 | Bayer Ag | Verfahren zur Herstellung von Butandiol-1,4 aus Maleinsäureanhydrid |
| DE19500783A1 (de) * | 1995-01-13 | 1996-07-18 | Bayer Ag | Verfahren zur Herstellung von aliphatischen alpha,omega-Diolen |
| DE69608105T2 (de) * | 1995-06-20 | 2000-11-09 | Kao Corp., Tokio/Tokyo | Verfahren zur herstellung von einem alkohol |
| DE19711404A1 (de) * | 1997-03-19 | 1998-09-24 | Hoechst Ag | Verfahren zur Herstellung von aromatischen Alkoholen |
| DE19754788A1 (de) * | 1997-12-10 | 1999-06-17 | Bayer Ag | Verfahren zur Herstellung von aliphatischen alpha,omega-Diolen |
| US7074603B2 (en) | 1999-03-11 | 2006-07-11 | Zeachem, Inc. | Process for producing ethanol from corn dry milling |
| ES2400285T3 (es) | 1999-03-11 | 2013-04-08 | Zeachem, Inc. | Proceso para producir etanol |
| DE10207443A1 (de) | 2002-02-22 | 2003-09-04 | Bayer Ag | Verfahren und Katalysator zur Herstellung von Alkoholen |
| DE10225926A1 (de) | 2002-06-11 | 2003-12-24 | Basf Ag | Verfahren zur Herstellung von Butandiol |
| DE10225927A1 (de) | 2002-06-11 | 2003-12-24 | Basf Ag | Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese |
| MX306561B (es) | 2004-01-29 | 2013-01-09 | Zeachem Inc | Recuperacion de acidos organicos. |
| CN105936887A (zh) | 2007-03-16 | 2016-09-14 | 基因组股份公司 | 用于1,4-丁二醇和其前体生物合成的组合物和方法 |
| US7947483B2 (en) | 2007-08-10 | 2011-05-24 | Genomatica, Inc. | Methods and organisms for the growth-coupled production of 1,4-butanediol |
| GB0719251D0 (en) | 2007-10-03 | 2007-11-14 | Davy Process Techn Ltd | Process |
| EP2245137B1 (fr) | 2008-01-22 | 2017-08-16 | Genomatica, Inc. | Méthodes et organismes d'utilisation de gaz de synthèse, d'autres sources de gaz carboné et de méthanol |
| EP2252697A4 (fr) | 2008-02-07 | 2012-05-30 | Zeachem Inc | Production indirecte de butanol et d hexanol |
| EP2262901B1 (fr) | 2008-03-05 | 2018-11-21 | Genomatica, Inc. | Organismes de production d alcools primaires |
| BRPI0911759A2 (pt) | 2008-05-01 | 2019-09-24 | Genomatica Inc | microorganismo para a produção de ácido metacrílico |
| MX302494B (es) | 2008-05-07 | 2012-08-17 | Zeachem Inc | Recuperacion de acidos organicos. |
| JP5912529B2 (ja) | 2008-09-10 | 2016-04-27 | ゲノマチカ， インク． | １，４−ブタンジオールの生成のための微生物体 |
| CN102292310B (zh) | 2008-12-02 | 2014-03-26 | 得克萨斯A&M大学体系 | 从生物质生产醇和烃的备选途径 |
| WO2010127303A1 (fr) | 2009-04-30 | 2010-11-04 | Genomatica, Inc. | Organismes pour la production d'isopropanol, de n-butanol et d'isobutanol |
| CN102625846B (zh) | 2009-04-30 | 2016-08-03 | 基因组股份公司 | 用于生产1,3-丁二醇的生物 |
| CN102498215A (zh) | 2009-06-04 | 2012-06-13 | 基因组股份公司 | 生产1,4-丁二醇的微生物和相关方法 |
| US20110124911A1 (en) | 2009-08-05 | 2011-05-26 | Burk Mark J | Semi-synthetic terephthalic acid via microorganisms that produce muconic acid |
| EE200900073A (et) | 2009-09-22 | 2011-06-15 | Nordbiochem O� | Katalsaator ja meetod hdrokskarbokslhapete estrite kataltiliseks hdrogeenimiseks glkoolideks |
| BR112012009332A2 (pt) | 2009-10-23 | 2015-09-15 | Genomatica Inc | micro-organismo para a produção de anilina |
| US8530210B2 (en) | 2009-11-25 | 2013-09-10 | Genomatica, Inc. | Microorganisms and methods for the coproduction 1,4-butanediol and gamma-butyrolactone |
| EP2529011A4 (fr) | 2010-01-29 | 2015-07-15 | Genomatica Inc | Micro-organismes et procédés pour la biosynthèse de p-toluate et téréphtalate |
| EP2357037A1 (fr) | 2010-02-17 | 2011-08-17 | LANXESS Deutschland GmbH | Procédé de fabrication de catalyseurs à haute stabilité méchanique |
| US9023636B2 (en) | 2010-04-30 | 2015-05-05 | Genomatica, Inc. | Microorganisms and methods for the biosynthesis of propylene |
| US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| US8846986B2 (en) | 2011-04-26 | 2014-09-30 | Celanese International Corporation | Water separation from crude alcohol product |
| US8901358B2 (en) | 2010-07-09 | 2014-12-02 | Celanese International Corporation | Esterification of vapor crude product in the production of alcohols |
| US9150474B2 (en) | 2010-07-09 | 2015-10-06 | Celanese International Corporation | Reduction of acid within column through esterification during the production of alcohols |
| US8859827B2 (en) | 2011-11-18 | 2014-10-14 | Celanese International Corporation | Esterifying acetic acid to produce ester feed for hydrogenolysis |
| US8846988B2 (en) | 2010-07-09 | 2014-09-30 | Celanese International Corporation | Liquid esterification for the production of alcohols |
| BR112013001635A2 (pt) | 2010-07-26 | 2016-05-24 | Genomatica Inc | micro-organismo e métodos para a biossíntese de aromáticos, 2, 4-pentadienoato e 1,3-butadieno |
| US9000233B2 (en) | 2011-04-26 | 2015-04-07 | Celanese International Corporation | Process to recover alcohol with secondary reactors for hydrolysis of acetal |
| US8907141B2 (en) | 2011-04-26 | 2014-12-09 | Celanese International Corporation | Process to recover alcohol with secondary reactors for esterification of acid |
| WO2012149137A1 (fr) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Procédé de production d'éthanol à partir d'une charge d'acide acétique et d'une charge d'acétate d'éthyle recyclé |
| US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
| US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
| GB201119871D0 (en) | 2011-11-17 | 2011-12-28 | Davy Process Techn Ltd | Process |
| US8853468B2 (en) | 2011-11-18 | 2014-10-07 | Celanese International Corporation | Vapor esterification method to produce ester feed for hydrogenolysis |
| US9024089B2 (en) | 2011-11-18 | 2015-05-05 | Celanese International Corporation | Esterification process using extractive separation to produce feed for hydrogenolysis |
| 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 |
| WO2013076747A1 (fr) | 2011-11-25 | 2013-05-30 | Conser Spa | Procédé de production de 1,4-butanediol par hydrogénation de maléate de dialkyle dans une phase mixte liquide/vapeur |
| US8697802B2 (en) | 2011-11-28 | 2014-04-15 | Celanese International Corporation | Process for producing polyvinyl alcohol or a copolymer thereof |
| US9029614B2 (en) | 2011-12-14 | 2015-05-12 | Celanese International Corporation | Phasing reactor product from hydrogenating acetic acid into ethyl acetate feed to produce ethanol |
| US9051235B2 (en) | 2012-02-07 | 2015-06-09 | Celanese International Corporation | Process for producing ethanol using a molar excess of hydrogen |
| US8975452B2 (en) | 2012-03-28 | 2015-03-10 | Celanese International Corporation | Process for producing ethanol by hydrocarbon oxidation and hydrogenation or hydration |
| EP2855687B1 (fr) | 2012-06-04 | 2020-04-22 | Genomatica, Inc. | Microorganismes et procédés de production du 4-hydroxybutyrate, 1,4-butanediol et composés associés |
| CN102766021B (zh) * | 2012-07-24 | 2014-04-09 | 唐山市冀东溶剂有限公司 | 乙酸乙酯加氢连续生产乙醇的生产系统以及生产方法 |
| CN104755449B (zh) | 2012-08-31 | 2016-09-21 | 罗门哈斯公司 | 由有机酸制备醇的方法 |
| GB201218078D0 (en) | 2012-10-09 | 2012-11-21 | Davy Process Techn Ltd | Process |
| US8853469B2 (en) | 2012-11-20 | 2014-10-07 | Celanese International Corporation | Combined column for separating products of different hydrogenation reactors |
| WO2014099433A1 (fr) * | 2012-12-20 | 2014-06-26 | Archer Daniels Midland Company | Production de biocarburants à partir d'esters d'acides carboxyliques bio-dérivés |
| KR101989655B1 (ko) | 2012-12-20 | 2019-06-14 | 아처 다니엘 미드랜드 캄파니 | 생물학적으로 유래된 카르복실산 에스테르로부터의 수소화 생성물 |
| US8975451B2 (en) | 2013-03-15 | 2015-03-10 | Celanese International Corporation | Single phase ester feed for hydrogenolysis |
| WO2014176514A2 (fr) | 2013-04-26 | 2014-10-30 | Genomatica, Inc. | Micro-organismes et procédés de production du 4-hydroxybutyrate, du 1,4-butanediol, et composés associés |
| DE102013106382A1 (de) | 2013-06-19 | 2014-12-24 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Verfahren zum Herstellen von Fettalkoholen aus Fettsäuremethylester |
| US20180222831A1 (en) * | 2015-08-05 | 2018-08-09 | White Dog Labs, Inc. | Method for the production of at least one derivate of a carboxylic acid |
| GB201617698D0 (en) | 2016-10-19 | 2016-11-30 | Johnson Matthey Davy Technologies Limited | Process |
| US10435349B2 (en) | 2017-08-02 | 2019-10-08 | Eastman Chemical Company | Iron-catalyzed cross-coupling of methanol with secondary or tertiary alcohols to produce formate esters |
| US10544077B2 (en) | 2017-08-02 | 2020-01-28 | Eastman Chemical Company | Process for making formic acid utilizing higher-boiling formate esters |
| US10266466B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Iron-catalyzed transfer hydrogenation of esters to alcohols |
| US10570081B2 (en) | 2017-08-02 | 2020-02-25 | Eastman Chemical Company | Process for making formic acid utilizing lower-boiling formate esters |
| US10266467B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Synthesis of glycols via transfer hydrogenation of alpha-functional esters with alcohols |
| KR20230156824A (ko) | 2021-03-12 | 2023-11-14 | 꼰세르 엣세.삐.아. | 2개의 스테이지들에서 디알킬 말리에이트를 수소화함으로써 디알킬 숙시네이트 및 1,4-부탄디올의 공생산을 위한 공정 |
| CN113713829A (zh) * | 2021-10-09 | 2021-11-30 | 凯瑞环保科技股份有限公司 | 一种醋酸仲丁酯加氢催化剂的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2248465A (en) * | 1936-12-19 | 1941-07-08 | American Hyalsol Corp | Process for the reduction of fatty acids to alcohols |
| US2285448A (en) * | 1937-10-30 | 1942-06-09 | Du Pont | Preparation of polyhydric alcohols |
| DE1005497B (de) * | 1954-03-19 | 1957-04-04 | Dehydag Gmbh | Verfahren zur Herstellung von Alkoholen |
| BE548808A (fr) * | 1955-07-08 | 1900-01-01 | ||
| GB932991A (en) * | 1959-02-02 | 1963-07-31 | Asahi Denka Kogyo Kk | Method for producing a copper containing catalyst |
| FR1303231A (fr) * | 1961-09-01 | 1962-09-07 | Hydrierwerk Rodleben Veb | Procédé de préparation d'alcools |
| BE622053A (fr) * | 1961-09-02 | 1900-01-01 | ||
| NL292315A (fr) * | 1962-05-05 | |||
| AT257556B (de) * | 1962-11-16 | 1967-10-10 | Celanese Corp | Verfahren zur Herstellung von Alkoholen |
| DE1768313B2 (de) * | 1968-04-27 | 1977-05-18 | Henkel & Cie GmbH, 4000 Düsseldorf | Verfahren zur herstellung hoehermolekularer mehrwertiger alkohole |
| DE2455617C3 (de) * | 1974-11-23 | 1982-03-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Butandiol und/oder Tetrahydrofuran über die Zwischenstufe des γ-Butyrolactons |
| DE2613226B2 (de) * | 1976-03-27 | 1978-12-14 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur kontinuierlichen Herstellung von Fettalkoholen |
| US4112245A (en) * | 1976-08-18 | 1978-09-05 | Atlantic Richfield Company | Process for the preparation of ethylene glycol |
| BE864567A (fr) * | 1977-04-25 | 1978-07-03 | Chevron Res | Procede d'hydrogenation d'esters en acools |
| US4199479A (en) * | 1978-02-24 | 1980-04-22 | Chevron Research Company | Hydrogenation catalyst |
-
1982
- 1982-04-20 IT IT20820/82A patent/IT1190783B/it active
- 1982-04-21 AU AU83365/82A patent/AU560590B2/en not_active Ceased
- 1982-04-21 GB GB08306413A patent/GB2116552B/en not_active Expired
- 1982-04-21 JP JP57501245A patent/JPS58500993A/ja active Granted
- 1982-04-21 WO PCT/GB1982/000118 patent/WO1982003854A1/fr active Application Filing
- 1982-04-21 NL NL8220121A patent/NL191438C/xx not_active IP Right Cessation
- 1982-04-21 BR BR8207962A patent/BR8207962A/pt unknown
- 1982-04-28 CA CA000401903A patent/CA1229096A/fr not_active Expired
- 1982-04-28 NZ NZ200442A patent/NZ200442A/xx unknown
- 1982-04-29 MX MX192496A patent/MX156577A/es unknown
- 1982-12-28 NO NO824396A patent/NO824396L/no unknown
-
1983
- 1983-05-24 FI FI831848A patent/FI831848L/fi not_active Application Discontinuation
- 1983-05-30 SE SE8303027A patent/SE452154B/sv not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102076646A (zh) * | 2009-04-07 | 2011-05-25 | 戴维加工技术有限公司 | 具有第一碳链长度的脂肪醇流和具有第二碳链长度的脂肪醇流的联合生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL191438B (nl) | 1995-03-01 |
| SE8303027L (sv) | 1983-05-30 |
| BR8207962A (pt) | 1983-10-04 |
| JPH0457655B2 (fr) | 1992-09-14 |
| SE452154B (sv) | 1987-11-16 |
| AU8336582A (en) | 1982-12-07 |
| NL191438C (nl) | 1995-07-04 |
| IT1190783B (it) | 1988-02-24 |
| WO1982003854A1 (fr) | 1982-11-11 |
| IT8220820A0 (it) | 1982-04-20 |
| JPS58500993A (ja) | 1983-06-23 |
| FI831848A0 (fi) | 1983-05-24 |
| GB8306413D0 (en) | 1983-04-13 |
| NZ200442A (en) | 1985-10-11 |
| SE8303027D0 (sv) | 1983-05-30 |
| FI831848L (fi) | 1983-05-24 |
| GB2116552A (en) | 1983-09-28 |
| MX156577A (es) | 1988-09-13 |
| NO824396L (no) | 1982-12-28 |
| GB2116552B (en) | 1985-09-25 |
| NL8220121A (nl) | 1983-07-01 |
| AU560590B2 (en) | 1987-04-09 |
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