CA1160252A - Process for producing gasoline-grade c.sub.2- c.sub.4 alcohols, from aqueous mixtures containing them - Google Patents
Process for producing gasoline-grade c.sub.2- c.sub.4 alcohols, from aqueous mixtures containing themInfo
- Publication number
- CA1160252A CA1160252A CA000374128A CA374128A CA1160252A CA 1160252 A CA1160252 A CA 1160252A CA 000374128 A CA000374128 A CA 000374128A CA 374128 A CA374128 A CA 374128A CA 1160252 A CA1160252 A CA 1160252A
- Authority
- CA
- Canada
- Prior art keywords
- water
- olefin
- isobutene
- ethanol
- mixture
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000008569 process Effects 0.000 title claims abstract description 12
- 150000001298 alcohols Chemical class 0.000 title abstract description 9
- 150000001336 alkenes Chemical group 0.000 claims abstract description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 10
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 10
- 239000000376 reactant Substances 0.000 claims abstract description 3
- 230000002378 acidificating effect Effects 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 92
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 3
- 230000036571 hydration Effects 0.000 claims description 3
- 238000006703 hydration reaction Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 125000001174 sulfone group Chemical group 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 3
- 229910006069 SO3H Inorganic materials 0.000 abstract description 2
- 230000003071 parasitic effect Effects 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 37
- 229960004756 ethanol Drugs 0.000 description 28
- 239000000047 product Substances 0.000 description 16
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 11
- -1 Amber-lyst* 15 Chemical compound 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 229920001429 chelating resin Polymers 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000009102 absorption Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000000727 fraction Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21068/80A IT1140794B (it) | 1980-03-31 | 1980-03-31 | Procedimento per la produzione di alcoli c2-c4 "grado benzine" da miscele acquose che li contengono |
| IT21068A/80 | 1980-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160252A true CA1160252A (en) | 1984-01-10 |
Family
ID=11176255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000374128A Expired CA1160252A (en) | 1980-03-31 | 1981-03-30 | Process for producing gasoline-grade c.sub.2- c.sub.4 alcohols, from aqueous mixtures containing them |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS56151790A (index.php) |
| AU (1) | AU550088B2 (index.php) |
| BE (1) | BE888150A (index.php) |
| BR (1) | BR8101872A (index.php) |
| CA (1) | CA1160252A (index.php) |
| CH (1) | CH648340A5 (index.php) |
| CS (1) | CS221292B2 (index.php) |
| DD (1) | DD157700A5 (index.php) |
| DE (1) | DE3112277C2 (index.php) |
| DK (1) | DK137281A (index.php) |
| ES (1) | ES8202776A1 (index.php) |
| FR (1) | FR2479186A1 (index.php) |
| GB (1) | GB2072668B (index.php) |
| HU (1) | HU192065B (index.php) |
| IE (1) | IE51127B1 (index.php) |
| IT (1) | IT1140794B (index.php) |
| LU (1) | LU83265A1 (index.php) |
| NL (1) | NL8101594A (index.php) |
| NO (1) | NO811022L (index.php) |
| NZ (1) | NZ196606A (index.php) |
| PL (1) | PL230427A1 (index.php) |
| RO (1) | RO84498B (index.php) |
| SE (1) | SE8101977L (index.php) |
| SU (1) | SU1034610A3 (index.php) |
| YU (1) | YU41038B (index.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7007764B2 (en) | 2002-12-06 | 2006-03-07 | Manitowoc Crane Companies, Inc. | Carbody to crawler connection |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0723331B2 (ja) * | 1985-03-12 | 1995-03-15 | 旭化成工業株式会社 | 第３級ブタノ−ルの製造方法 |
| JP2007021643A (ja) * | 2005-07-15 | 2007-02-01 | Amada Co Ltd | 永久磁石を用いたワーク吸着装置 |
| US10570071B1 (en) | 2018-12-12 | 2020-02-25 | Saudi Arabian Oil Company | Membrane-based process for butanols production from mixed butenes |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL299568A (index.php) * | 1900-01-01 | |||
| FR1314120A (fr) * | 1962-01-08 | 1963-01-04 | Bayer Ag | Procédé de préparation d'éthers de tert.-butyle et d'alcoyles |
| DE1249844B (de) * | 1962-03-21 | 1967-09-14 | GuIf Research &. Development Company, Pittsburgh, Pa (V St A) | Verfahren zur Herstellung von Alkoholen durch Anlagerung von Wasser an die entsprechenden Olefine m flussiger Phase |
| US3822119A (en) * | 1970-11-19 | 1974-07-02 | Goodyear Tire & Rubber | Anti-pollution anti-knock gasoline |
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| US4087471A (en) * | 1977-05-20 | 1978-05-02 | Petro-Tex Chemical Corporation | Fixed bed process for the production of t-butanol |
-
1980
- 1980-03-31 IT IT21068/80A patent/IT1140794B/it active
-
1981
- 1981-03-18 IE IE602/81A patent/IE51127B1/en unknown
- 1981-03-19 GB GB8108640A patent/GB2072668B/en not_active Expired
- 1981-03-24 NZ NZ196606A patent/NZ196606A/en unknown
- 1981-03-26 DK DK137281A patent/DK137281A/da not_active Application Discontinuation
- 1981-03-26 BR BR8101872A patent/BR8101872A/pt unknown
- 1981-03-26 FR FR8106118A patent/FR2479186A1/fr active Granted
- 1981-03-26 NO NO811022A patent/NO811022L/no unknown
- 1981-03-27 SE SE8101977A patent/SE8101977L/xx not_active Application Discontinuation
- 1981-03-27 DE DE3112277A patent/DE3112277C2/de not_active Expired
- 1981-03-27 BE BE0/204278A patent/BE888150A/fr not_active IP Right Cessation
- 1981-03-30 YU YU828/81A patent/YU41038B/xx unknown
- 1981-03-30 CH CH2146/81A patent/CH648340A5/it not_active IP Right Cessation
- 1981-03-30 JP JP4566881A patent/JPS56151790A/ja active Pending
- 1981-03-30 LU LU83265A patent/LU83265A1/fr unknown
- 1981-03-30 SU SU813266251A patent/SU1034610A3/ru active
- 1981-03-30 CA CA000374128A patent/CA1160252A/en not_active Expired
- 1981-03-30 HU HU81810A patent/HU192065B/hu unknown
- 1981-03-30 AU AU68903/81A patent/AU550088B2/en not_active Ceased
- 1981-03-30 RO RO103858A patent/RO84498B/ro unknown
- 1981-03-30 PL PL23042781A patent/PL230427A1/xx unknown
- 1981-03-31 NL NL8101594A patent/NL8101594A/nl not_active Application Discontinuation
- 1981-03-31 CS CS812393A patent/CS221292B2/cs unknown
- 1981-03-31 ES ES501396A patent/ES8202776A1/es not_active Expired
- 1981-03-31 DD DD81228774A patent/DD157700A5/de unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7007764B2 (en) | 2002-12-06 | 2006-03-07 | Manitowoc Crane Companies, Inc. | Carbody to crawler connection |
Also Published As
| Publication number | Publication date |
|---|---|
| DD157700A5 (de) | 1982-12-01 |
| FR2479186A1 (fr) | 1981-10-02 |
| IT8021068A0 (it) | 1980-03-31 |
| SE8101977L (sv) | 1981-10-01 |
| HU192065B (en) | 1987-05-28 |
| RO84498B (ro) | 1984-08-30 |
| FR2479186B1 (index.php) | 1982-11-26 |
| IE51127B1 (en) | 1986-10-15 |
| DK137281A (da) | 1981-10-01 |
| GB2072668A (en) | 1981-10-07 |
| PL230427A1 (index.php) | 1981-11-13 |
| YU41038B (en) | 1986-10-31 |
| DE3112277C2 (de) | 1985-05-02 |
| NO811022L (no) | 1981-10-01 |
| ES501396A0 (es) | 1982-02-16 |
| CH648340A5 (it) | 1985-03-15 |
| RO84498A (ro) | 1984-06-21 |
| DE3112277A1 (de) | 1982-03-18 |
| IT1140794B (it) | 1986-10-10 |
| NL8101594A (nl) | 1981-10-16 |
| CS221292B2 (en) | 1983-04-29 |
| SU1034610A3 (ru) | 1983-08-07 |
| YU82881A (en) | 1983-02-28 |
| NZ196606A (en) | 1984-03-16 |
| AU550088B2 (en) | 1986-03-06 |
| AU6890381A (en) | 1981-10-08 |
| IE810602L (en) | 1981-09-30 |
| BE888150A (fr) | 1981-09-28 |
| ES8202776A1 (es) | 1982-02-16 |
| JPS56151790A (en) | 1981-11-24 |
| BR8101872A (pt) | 1981-10-06 |
| GB2072668B (en) | 1984-03-28 |
| LU83265A1 (fr) | 1981-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |