DE1291729B - Verfahren zur Hydratisierung von niederen Olefinen zu Alkoholen und AEthern - Google Patents
Verfahren zur Hydratisierung von niederen Olefinen zu Alkoholen und AEthernInfo
- Publication number
- DE1291729B DE1291729B DER46245A DER0046245A DE1291729B DE 1291729 B DE1291729 B DE 1291729B DE R46245 A DER46245 A DE R46245A DE R0046245 A DER0046245 A DE R0046245A DE 1291729 B DE1291729 B DE 1291729B
- Authority
- DE
- Germany
- Prior art keywords
- ethers
- alcohols
- sulfonic acid
- catalyst
- hydration
- 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.)
- Pending
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 20
- 230000036571 hydration Effects 0.000 title claims description 8
- 238000006703 hydration reaction Methods 0.000 title claims description 8
- 150000001298 alcohols Chemical class 0.000 title claims description 4
- 150000002170 ethers Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 13
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- -1 aliphatic sulfonic acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 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 description 1
- HHBZZTKMMLDNDN-UHFFFAOYSA-N 2-butan-2-yloxybutane Chemical compound CCC(C)OC(C)CC HHBZZTKMMLDNDN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- 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
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER46245A DE1291729B (de) | 1967-06-14 | 1967-06-14 | Verfahren zur Hydratisierung von niederen Olefinen zu Alkoholen und AEthern |
| CH635768A CH500147A (de) | 1967-06-14 | 1968-04-29 | Verfahren zur gleichzeitigen Herstellung von Alkoholen und Äthern durch Direkthydratisierung von Olefinen |
| AT422468A AT284804B (de) | 1967-06-14 | 1968-05-02 | Verfahren zur Herstellung von Alkoholen und Äthern |
| GB2471968A GB1208144A (en) | 1967-06-14 | 1968-05-23 | Process for the hydration of olefins to produce alcohols and ethers |
| NL6807638A NL6807638A (forum.php) | 1967-06-14 | 1968-05-30 | |
| FR1570877D FR1570877A (forum.php) | 1967-06-14 | 1968-06-14 | |
| BE716619D BE716619A (forum.php) | 1967-06-14 | 1968-06-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER46245A DE1291729B (de) | 1967-06-14 | 1967-06-14 | Verfahren zur Hydratisierung von niederen Olefinen zu Alkoholen und AEthern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1291729B true DE1291729B (de) | 1969-04-03 |
Family
ID=7407943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER46245A Pending DE1291729B (de) | 1967-06-14 | 1967-06-14 | Verfahren zur Hydratisierung von niederen Olefinen zu Alkoholen und AEthern |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT284804B (forum.php) |
| BE (1) | BE716619A (forum.php) |
| CH (1) | CH500147A (forum.php) |
| DE (1) | DE1291729B (forum.php) |
| FR (1) | FR1570877A (forum.php) |
| GB (1) | GB1208144A (forum.php) |
| NL (1) | NL6807638A (forum.php) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2040501A1 (de) * | 1970-08-14 | 1972-02-17 | Basf Ag | Verfahren zur Durchfuehrung von exothermen Reaktionen zwischen einem Gas und einer Fluessigkeit |
| US4281206A (en) * | 1974-01-30 | 1981-07-28 | Deutsche Texaco Aktiengesellschaft | Method of conducting reactions in a trickle-type reactor |
| DE3628007C1 (forum.php) * | 1986-08-19 | 1987-11-05 | Deutsche Texaco Ag, 2000 Hamburg, De |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469905A (en) * | 1981-11-04 | 1984-09-04 | Union Oil Company Of California | Process for producing and extracting C2 to C6 alcohols |
| US5763693A (en) * | 1995-02-24 | 1998-06-09 | Mitsui Chemicals, Inc. | Process for producing isopropyl alcohol |
| JP3600213B2 (ja) * | 2002-01-24 | 2004-12-15 | 独立行政法人 科学技術振興機構 | １，２−ジオールの新規製造法 |
| CN115569615A (zh) * | 2022-10-31 | 2023-01-06 | 厦门大学 | 一种柠檬烯制备松油醇的反应装置及其合成方法 |
-
1967
- 1967-06-14 DE DER46245A patent/DE1291729B/de active Pending
-
1968
- 1968-04-29 CH CH635768A patent/CH500147A/de not_active IP Right Cessation
- 1968-05-02 AT AT422468A patent/AT284804B/de not_active IP Right Cessation
- 1968-05-23 GB GB2471968A patent/GB1208144A/en not_active Expired
- 1968-05-30 NL NL6807638A patent/NL6807638A/xx unknown
- 1968-06-14 BE BE716619D patent/BE716619A/xx unknown
- 1968-06-14 FR FR1570877D patent/FR1570877A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2040501A1 (de) * | 1970-08-14 | 1972-02-17 | Basf Ag | Verfahren zur Durchfuehrung von exothermen Reaktionen zwischen einem Gas und einer Fluessigkeit |
| US4281206A (en) * | 1974-01-30 | 1981-07-28 | Deutsche Texaco Aktiengesellschaft | Method of conducting reactions in a trickle-type reactor |
| DE3628007C1 (forum.php) * | 1986-08-19 | 1987-11-05 | Deutsche Texaco Ag, 2000 Hamburg, De |
Also Published As
| Publication number | Publication date |
|---|---|
| BE716619A (forum.php) | 1968-12-16 |
| CH500147A (de) | 1970-12-15 |
| NL6807638A (forum.php) | 1968-12-16 |
| FR1570877A (forum.php) | 1969-06-13 |
| GB1208144A (en) | 1970-10-07 |
| AT284804B (de) | 1970-09-25 |
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