CA1213292A - Procede de preparation de l'ethanol a partir de gaz de synthese - Google Patents

Procede de preparation de l'ethanol a partir de gaz de synthese

Info

Publication number: CA1213292A
Authority: CA; Canada
Prior art keywords: cocatalyst; catalyst; rhodium; weight; ethanol
Prior art date: 1978-10-24
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

Application number

CA000338193A

Other languages

English (en)

Inventor

Ernst I. Leupold

Hans-Joachim Schmidt

Friedrich Wunder

Hans-Jurgen Arpe

Horst Hachenberg

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-10-24

Filing date

1979-10-23

Publication date

1986-10-28

1979-10-23 Application filed by Hoechst AG filed Critical Hoechst AG

1979-10-23 Priority to CA000338193A priority Critical patent/CA1213292A/fr

1986-10-28 Application granted granted Critical

1986-10-28 Publication of CA1213292A publication Critical patent/CA1213292A/fr

Status Expired legal-status Critical Current

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 63
238000000034 method Methods 0.000 title claims abstract description 40
230000015572 biosynthetic process Effects 0.000 title abstract description 13
238000003786 synthesis reaction Methods 0.000 title abstract description 7
238000004519 manufacturing process Methods 0.000 title abstract description 4
239000003054 catalyst Substances 0.000 claims abstract description 48
239000010948 rhodium Substances 0.000 claims abstract description 39
229910052703 rhodium Inorganic materials 0.000 claims abstract description 33
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 31
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 15
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
238000006243 chemical reaction Methods 0.000 claims abstract description 13
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
239000011651 chromium Substances 0.000 claims abstract description 9
229910052735 hafnium Inorganic materials 0.000 claims abstract description 9
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 9
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052753 mercury Inorganic materials 0.000 claims abstract description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052804 chromium Inorganic materials 0.000 claims abstract description 8
229910052746 lanthanum Inorganic materials 0.000 claims abstract description 7
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052697 platinum Inorganic materials 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 8
239000011777 magnesium Substances 0.000 claims description 6
150000004760 silicates Chemical class 0.000 claims description 6
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 6
235000012239 silicon dioxide Nutrition 0.000 claims description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims 9
239000002184 metal Substances 0.000 claims 9
150000003841 chloride salts Chemical class 0.000 claims 3
239000000460 chlorine Substances 0.000 claims 3
229910052801 chlorine Inorganic materials 0.000 claims 3
125000001309 chloro group Chemical class Cl* 0.000 claims 3
150000002739 metals Chemical class 0.000 claims 3
239000007789 gas Substances 0.000 abstract description 24
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 abstract description 5
229910052726 zirconium Inorganic materials 0.000 abstract description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
239000001301 oxygen Substances 0.000 description 8
229910052760 oxygen Inorganic materials 0.000 description 8
239000000203 mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
-1 bis-tri-o-tolyl phosphine-rhodium Chemical compound 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
150000001805 chlorine compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002253 acid Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000282320 Panthera leo Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000007792 gaseous phase Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
159000000014 iron salts Chemical class 0.000 description 2
239000011148 porous material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
235000009434 Actinidia chinensis Nutrition 0.000 description 1
244000298697 Actinidia deliciosa Species 0.000 description 1
235000009436 Actinidia deliciosa Nutrition 0.000 description 1
241000132092 Aster Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229910021555 Chromium Chloride Inorganic materials 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
KDRIEERWEFJUSB-UHFFFAOYSA-N carbon dioxide;methane Chemical compound C.O=C=O KDRIEERWEFJUSB-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000003467 diminishing effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000003517 fume Substances 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
BSUHUYNJLGMEPD-UHFFFAOYSA-N methanol;propan-1-ol Chemical compound OC.CCCO BSUHUYNJLGMEPD-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
150000003284 rhodium compounds Chemical class 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000000926 separation method Methods 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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000338193A 1978-10-24 1979-10-23 Procede de preparation de l'ethanol a partir de gaz de synthese Expired CA1213292A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000338193A CA1213292A (fr)	1978-10-24	1979-10-23	Procede de preparation de l'ethanol a partir de gaz de synthese

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2846148.5		1978-10-24
CA000338193A CA1213292A (fr)	1978-10-24	1979-10-23	Procede de preparation de l'ethanol a partir de gaz de synthese

Publications (1)

Publication Number	Publication Date
CA1213292A true CA1213292A (fr)	1986-10-28

Family

ID=4115406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000338193A Expired CA1213292A (fr)	1978-10-24	1979-10-23	Procede de preparation de l'ethanol a partir de gaz de synthese

Country Status (1)

Country	Link
CA (1)	CA1213292A (fr)

1979
- 1979-10-23 CA CA000338193A patent/CA1213292A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2003-10-28	MKEX	Expiry

Publication	Publication Date	Title
US4442228A (en)	1984-04-10	Process for the manufacture of ethanol from synthesis gas
EP0269718B1 (fr)	1991-10-16	Procede catalytique a phase de vapeur permettant de produire des carbonates de dihydrocarbyle
CA1211098A (fr)	1986-09-09	Conversion du methane en olepines et son hydrogene
US4375566A (en)	1983-03-01	Process for producing ortho-alkylated phenols from anisoles
US4224236A (en)	1980-09-23	Process for the manufacture of oxygen-containing carbon compounds from synthesis gas
CA1168270A (fr)	1984-05-29	Methode d'obtention d'hydrocarbures c.sub.1 a c.sub.4 oxygenes, par conversion catalytique de gaz de synthese
US4289710A (en)	1981-09-15	Process for producing methanol from synthesis gas with palladium-calcium catalysts
EP0031243B1 (fr)	1984-02-01	Préparation de méthanol à partir de gaz de synthèse au moyen de catalyseurs au palladium dopés
EP0030110B1 (fr)	1984-07-25	Procédé de production d'un composé hydrocarboné oxygéné contenant de l'éthanol
KR870000057B1 (ko)	1987-02-09	옥살산 디에스테르의 제법
US4579976A (en)	1986-04-01	Catalytic process for the preparation of trifluoroacetaldehyde
CA1117140A (fr)	1982-01-26	Procede de fabrication de composes carbones oxygenes, a partir de gaz de synthese
US3739020A (en)	1973-06-12	Preparation of carboxylic acids
US4579974A (en)	1986-04-01	Catalytic process for the preparation of hexafluoroacetone
CA1147749A (fr)	1983-06-07	Methode de fabrication de carbones oxygenes et d'olefines a partir de gaz de synthese
US2580284A (en)	1951-12-25	Production of secondary aromatic amines
CA1248144A (fr)	1989-01-03	Obtention de monoalcoyleneglycol ameliore a l'aide de dioxyde de carbone
US3944604A (en)	1976-03-16	Production of propionic acid
US4593147A (en)	1986-06-03	Synthesis of neoalkanes
CA1222773A (fr)	1987-06-09	Fabrication de l'acide acetique, de l'acetaldehyde et du methanol
US4293499A (en)	1981-10-06	Process for producing a carboxylate ester using a supported acidic catalyst
CA1220494A (fr)	1987-04-14	Production d'ethanol
EP0004732B1 (fr)	1981-12-23	Préparation du 2-phényléthanol et de l'acétate de 2-phényléthanol
CA1182476A (fr)	1985-02-12	Obtention d'acide acetique, acetaldehyde et d'ethanol a partir de gaz de synthese
EP0171206B1 (fr)	1988-12-07	Préparation d'hydrocarbures et d'hydrocarbures oxydés