NL8202489A - Werkwijze ter bereiding van ethanolen uit synthesegas. - Google Patents

Werkwijze ter bereiding van ethanolen uit synthesegas. Download PDF

Info

Publication number: NL8202489A
Authority: NL; Netherlands
Prior art keywords: ruthenium; manganese; rhenium; salt; carbonyl
Prior art date: 1981-06-26

Application number

NL8202489A

Other languages

English (en)

Dutch (nl)

Original Assignee

Texaco Development Corp

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.)

1981-06-26

Filing date

1982-06-18

Publication date

1983-01-17

1982-06-18 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1983-01-17 Publication of NL8202489A publication Critical patent/NL8202489A/nl

Links

230000015572 biosynthetic process Effects 0.000 title description 12
238000003786 synthesis reaction Methods 0.000 title description 11
238000004519 manufacturing process Methods 0.000 title description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 26
229910052702 rhenium Inorganic materials 0.000 claims description 26
229910052707 ruthenium Inorganic materials 0.000 claims description 25
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 19
229910052748 manganese Inorganic materials 0.000 claims description 19
239000011572 manganese Substances 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
238000002844 melting Methods 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000005496 phosphonium group Chemical group 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
239000003446 ligand Substances 0.000 claims description 5
230000008018 melting Effects 0.000 claims description 5
NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 claims description 4
235000006748 manganese carbonate Nutrition 0.000 claims description 3
239000011656 manganese carbonate Substances 0.000 claims description 3
229910000016 manganese(II) carbonate Inorganic materials 0.000 claims description 3
XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 claims description 3
150000003303 ruthenium Chemical class 0.000 claims description 3
ZIZHEHXAMPQGEK-UHFFFAOYSA-N dirhenium decacarbonyl Chemical group [Re].[Re].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] ZIZHEHXAMPQGEK-UHFFFAOYSA-N 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 2
239000012327 Ruthenium complex Substances 0.000 claims 1
QFEOTYVTTQCYAZ-UHFFFAOYSA-N dimanganese decacarbonyl Chemical group [Mn].[Mn].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] QFEOTYVTTQCYAZ-UHFFFAOYSA-N 0.000 claims 1
150000002696 manganese Chemical class 0.000 claims 1
229940093474 manganese carbonate Drugs 0.000 claims 1
150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
150000003281 rhenium Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
229910052739 hydrogen Inorganic materials 0.000 description 20
239000001257 hydrogen Substances 0.000 description 19
239000007789 gas Substances 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 13
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
229910002091 carbon monoxide Inorganic materials 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 9
239000012263 liquid product Substances 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
-1 phosphine oxide compound Chemical class 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
239000012018 catalyst precursor Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 4
238000001816 cooling Methods 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910052703 rhodium Inorganic materials 0.000 description 4
239000010948 rhodium Substances 0.000 description 4
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000007792 addition Methods 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
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 3
150000004714 phosphonium salts Chemical group 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 3
RDMHXWZYVFGYSF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical compound [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RDMHXWZYVFGYSF-LNTINUHCSA-N 0.000 description 2
IYWJIYWFPADQAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;ruthenium Chemical compound [Ru].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O IYWJIYWFPADQAN-LNTINUHCSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
238000003109 Karl Fischer titration Methods 0.000 description 2
WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical group [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
FGEKTVAHFDQHBU-UHFFFAOYSA-N dioxoruthenium;hydrate Chemical compound O.O=[Ru]=O FGEKTVAHFDQHBU-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002168 ethanoic acid esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
150000002697 manganese compounds Chemical class 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 2
AHSBSUVHXDIAEY-UHFFFAOYSA-K manganese(iii) acetate Chemical compound [Mn+3].CC([O-])=O.CC([O-])=O.CC([O-])=O AHSBSUVHXDIAEY-UHFFFAOYSA-K 0.000 description 2
GEYXPJBPASPPLI-UHFFFAOYSA-N manganese(iii) oxide Chemical compound O=[Mn]O[Mn]=O GEYXPJBPASPPLI-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000004437 phosphorous atom Chemical group 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
150000003304 ruthenium compounds Chemical class 0.000 description 2
OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QYAPHLRPFNSDNH-MRFRVZCGSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 1
UNANDJIJRBQOOF-UHFFFAOYSA-N 5-(dimethoxymethyl)-1,3-benzodioxole Chemical compound COC(OC)C1=CC=C2OCOC2=C1 UNANDJIJRBQOOF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
KRSZDIGCQWBYNU-UHFFFAOYSA-N [Mn].[Ru] Chemical compound [Mn].[Ru] KRSZDIGCQWBYNU-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000001450 anions Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000010949 copper Substances 0.000 description 1
KYCIUIVANPKXLW-UHFFFAOYSA-N dimethyl-(2-phenoxyethyl)-(thiophen-2-ylmethyl)azanium Chemical compound C=1C=CSC=1C[N+](C)(C)CCOC1=CC=CC=C1 KYCIUIVANPKXLW-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
WCZSOHSGMBVYFW-UHFFFAOYSA-M heptyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCC)C1=CC=CC=C1 WCZSOHSGMBVYFW-UHFFFAOYSA-M 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000004679 hydroxides Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
ZQZQURFYFJBOCE-FDGPNNRMSA-L manganese(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Mn+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O ZQZQURFYFJBOCE-FDGPNNRMSA-L 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
RGVLTEMOWXGQOS-UHFFFAOYSA-L manganese(2+);oxalate Chemical compound [Mn+2].[O-]C(=O)C([O-])=O RGVLTEMOWXGQOS-UHFFFAOYSA-L 0.000 description 1
PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical compound [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
VASIZKWUTCETSD-UHFFFAOYSA-N manganese(II) oxide Inorganic materials [Mn]=O VASIZKWUTCETSD-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
OZMOTUUZLXMHJR-UHFFFAOYSA-K pentanoate ruthenium(3+) Chemical compound C(CCCC)(=O)[O-].[Ru+3].C(CCCC)(=O)[O-].C(CCCC)(=O)[O-] OZMOTUUZLXMHJR-UHFFFAOYSA-K 0.000 description 1
PXBGQFYGVFUKNE-UHFFFAOYSA-N phosphanium;acetate Chemical group [PH4+].CC([O-])=O PXBGQFYGVFUKNE-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003282 rhenium compounds Chemical class 0.000 description 1
WXBOMIKEWRRKBB-UHFFFAOYSA-N rhenium(iv) oxide Chemical compound O=[Re]=O WXBOMIKEWRRKBB-UHFFFAOYSA-N 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
RADGOBKLTHEUQO-UHFFFAOYSA-N ruthenium(4+) Chemical compound [Ru+4] RADGOBKLTHEUQO-UHFFFAOYSA-N 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- C07C29/15—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 oxides of carbon exclusively
- C07C29/151—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/153—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
- C07C29/156—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
- C07C29/157—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof containing platinum group metals or compounds thereof
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8202489A 1981-06-26 1982-06-18 Werkwijze ter bereiding van ethanolen uit synthesegas. NL8202489A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/277,527 US4332914A (en)	1981-06-26	1981-06-26	Manufacture of alkanols from synthesis gas
US27752781		1981-06-26

Publications (1)

Publication Number	Publication Date
NL8202489A true NL8202489A (nl)	1983-01-17

Family

ID=23061255

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8202489A NL8202489A (nl)	1981-06-26	1982-06-18	Werkwijze ter bereiding van ethanolen uit synthesegas.

Country Status (11)

Country	Link
US (1)	US4332914A (it)
JP (1)	JPS58921A (it)
AU (1)	AU553505B2 (it)
BE (1)	BE893653A (it)
CA (1)	CA1181100A (it)
DE (1)	DE3221608A1 (it)
FR (1)	FR2508438B1 (it)
GB (1)	GB2100726B (it)
IT (1)	IT1159075B (it)
NL (1)	NL8202489A (it)
ZA (1)	ZA823324B (it)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4362821A (en) *	1981-10-29	1982-12-07	Texaco Inc.	Process for preparing alkanols from synthesis gas
US4396726A (en) *	1982-01-13	1983-08-02	Texaco Inc.	Process for preparing ethylene glycol and lower monohydric alcohols from syn gas using a novel catalyst system
US4939292A (en) *	1985-08-01	1990-07-03	Phillips Petroleum Company	Synthesis of esters from alcohols containing carbon monoxide as an impurity
JPH0669569B2 (ja) *	1988-08-18	1994-09-07	新日本製鐵株式会社	内部性状の優れた極厚鋼板の製造方法
MY153782A (en) *	2008-06-24	2015-03-13	Cosmo Oil Co Ltd	Catalyst for fischer-tropsch synthesis and method for producing hydrocarbons
GB201214122D0 (en) *	2012-08-07	2012-09-19	Oxford Catalysts Ltd	Treating of catalyst support
US8912240B2 (en)	2013-02-22	2014-12-16	Eastman Chemical Company	Production of methanol and ethanol from CO or CO2

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4206134A (en) *	1979-03-12	1980-06-03	Exxon Research & Engineering Co.	Ruthenium supported on manganese oxide as hydrocarbon synthesis catalysts in CO/H2 reactions
US4265828A (en) *	1979-12-31	1981-05-05	Texaco Development Corp.	Manufacture of ethylene glycol from synthesis gas
JPS57130939A (en) *	1981-02-04	1982-08-13	Mitsui Petrochem Ind Ltd	Synthetic method of alkane polyol

1981
- 1981-06-26 US US06/277,527 patent/US4332914A/en not_active Expired - Fee Related
1982
- 1982-05-11 GB GB08213658A patent/GB2100726B/en not_active Expired
- 1982-05-13 ZA ZA823324A patent/ZA823324B/xx unknown
- 1982-06-08 DE DE19823221608 patent/DE3221608A1/de not_active Withdrawn
- 1982-06-14 JP JP57100803A patent/JPS58921A/ja active Pending
- 1982-06-18 NL NL8202489A patent/NL8202489A/nl not_active Application Discontinuation
- 1982-06-21 CA CA000405583A patent/CA1181100A/en not_active Expired
- 1982-06-24 FR FR8211074A patent/FR2508438B1/fr not_active Expired
- 1982-06-24 AU AU85181/82A patent/AU553505B2/en not_active Ceased
- 1982-06-24 IT IT22057/82A patent/IT1159075B/it active
- 1982-06-25 BE BE0/208452A patent/BE893653A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
US4332914A (en)	1982-06-01
ZA823324B (en)	1983-09-28
IT1159075B (it)	1987-02-25
FR2508438B1 (fr)	1986-10-24
AU8518182A (en)	1983-01-06
JPS58921A (ja)	1983-01-06
FR2508438A1 (fr)	1982-12-31
AU553505B2 (en)	1986-07-17
CA1181100A (en)	1985-01-15
BE893653A (fr)	1982-12-27
GB2100726B (en)	1985-04-11
IT8222057A0 (it)	1982-06-24
GB2100726A (en)	1983-01-06
DE3221608A1 (de)	1983-01-13

Publication	Publication Date	Title
EP0108847B1 (en)	1986-06-18	Production of acetic acid, propionic acid and their esters
US4476326A (en)	1984-10-09	Process for the synthesis of ethanol and acetaldehyde using cobalt compounds with novel promoters
EP0048918B1 (en)	1985-05-22	Process for the selective production of ethanol and methanol directly from synthesis gas
US4390734A (en)	1983-06-28	Process for producing propylene glycol monoalkyl ethers from acetaldehyde, an alkanol and syngas using a new catalyst system
NL7906415A (nl)	1980-03-04	Werkwijze ter bereiding van alifatische carbonzuren en de esterderivaten hiervan.
NL8202489A (nl)	1983-01-17	Werkwijze ter bereiding van ethanolen uit synthesegas.
US4605677A (en)	1986-08-12	Process for C1 -C4 alkanol production from synthesis gas
EP0055514B1 (en)	1984-08-01	Preparation of glycols and ethers
EP0027000B1 (en)	1983-07-13	Methanol conversion with co or co+h2 using iron-cobalt catalyst
KR860000448B1 (ko)	1986-04-26	합성가스로부터 알칸올을 제조하는 방법
US4332915A (en)	1982-06-01	Production of alkanols from synthesis gas
EP0078616A2 (en)	1983-05-11	Process for preparing ethylene glycol
US4334092A (en)	1982-06-08	Method of preparing aliphatic carboxylic acids
US4622343A (en)	1986-11-11	Process for C1 -C4 alkanol production from synthesis gas using a trimetallic catalyst
EP0078615B1 (en)	1985-07-03	Process for preparing glycol ethers
US4519956A (en)	1985-05-28	Process for selectively preparing acetic anhydride by carbonylation of methyl acetate in the presence of an iodide-free catalyst system
EP0013464A1 (en)	1980-07-23	Selective formation of ethanol from methanol, hydrogen and carbon monoxide
CA1192226A (en)	1985-08-20	Process for preparing ethylene glycol and lower monohydric alcohols from syngas using a novel catalyst system
NL8105596A (nl)	1982-07-16	Bereiding van ethyleenglycol en ethers daarvan.
US4434248A (en)	1984-02-28	Process for preparing alkanols from synthesis gas
US4518715A (en)	1985-05-21	Process for producing ethylene glycol using a ruthenium-copper catalyst
US4525481A (en)	1985-06-25	Acetaldehyde production from synthesis gas
US4362822A (en)	1982-12-07	Process for preparing acetic and propionic acids and their esters
US4433176A (en)	1984-02-21	Process for preparing acetaldehyde from methanol and synthesis gas using a novel catalyst composition
Kniftona et al.	1984	bTexaco Research Center, Beacon, New York 12508

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-02-01	BV	The patent application has lapsed