NL8103846A - Werkwijze voor het hydrateren van propeen tot isopropylalcohol over vaste superzure geperfluoreerde sulfonzuurkatalysatoren. - Google Patents
Werkwijze voor het hydrateren van propeen tot isopropylalcohol over vaste superzure geperfluoreerde sulfonzuurkatalysatoren. Download PDFInfo
- Publication number
- NL8103846A NL8103846A NL8103846A NL8103846A NL8103846A NL 8103846 A NL8103846 A NL 8103846A NL 8103846 A NL8103846 A NL 8103846A NL 8103846 A NL8103846 A NL 8103846A NL 8103846 A NL8103846 A NL 8103846A
- Authority
- NL
- Netherlands
- Prior art keywords
- sulfonic acid
- propylene
- isopropyl alcohol
- acid
- perfluorinated
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 54
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 23
- 239000002253 acid Substances 0.000 title claims description 21
- 239000007787 solid Substances 0.000 title claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title claims description 7
- 230000000887 hydrating effect Effects 0.000 title claims description 6
- 239000003377 acid catalyst Substances 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 35
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 239000003930 superacid Substances 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 8
- 150000003460 sulfonic acids Chemical class 0.000 claims description 7
- LYCAGOQDEOWYGS-UHFFFAOYSA-N 1,2,2-trifluoroethenesulfonic acid Chemical compound OS(=O)(=O)C(F)=C(F)F LYCAGOQDEOWYGS-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 30
- 229960004592 isopropanol Drugs 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 230000036571 hydration Effects 0.000 description 13
- 238000006703 hydration reaction Methods 0.000 description 13
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000012808 vapor phase Substances 0.000 description 9
- 229920000557 Nafion® Polymers 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 alkane sulfonic acids Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QFAIDPCBDQJRJD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-tritriacontafluorohexadecane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QFAIDPCBDQJRJD-UHFFFAOYSA-N 0.000 description 1
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical class FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- 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
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- SHWHUCFJRAMLQS-UHFFFAOYSA-N sulfuryl difluoride;1,1,2-trifluoroethene Chemical compound FC=C(F)F.FS(F)(=O)=O SHWHUCFJRAMLQS-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 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
- 238000005292 vacuum distillation Methods 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
- C07C29/03—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17888980A | 1980-08-18 | 1980-08-18 | |
| US17888980 | 1980-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8103846A true NL8103846A (nl) | 1982-03-16 |
Family
ID=22654319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8103846A NL8103846A (nl) | 1980-08-18 | 1981-08-17 | Werkwijze voor het hydrateren van propeen tot isopropylalcohol over vaste superzure geperfluoreerde sulfonzuurkatalysatoren. |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5759823A (enrdf_load_stackoverflow) |
| BE (1) | BE889943A (enrdf_load_stackoverflow) |
| CA (1) | CA1180355A (enrdf_load_stackoverflow) |
| DE (1) | DE3131975A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2488600B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2082178B (enrdf_load_stackoverflow) |
| IT (1) | IT1189022B (enrdf_load_stackoverflow) |
| NL (1) | NL8103846A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595786A (en) * | 1984-11-27 | 1986-06-17 | E. I. Du Pont De Nemours And Company | Hydration of cyclohexene in presence of perfluorosulfonic acid polymer |
| US5233102A (en) * | 1989-08-02 | 1993-08-03 | E. I. Du Pont De Nemours And Company | Olefin hydration |
| US5094995A (en) * | 1989-08-02 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Supported perfluorinated ion-exchange polymers |
| WO2008000682A1 (en) * | 2006-06-27 | 2008-01-03 | Clariant International Ltd | Fluorous telomeric compounds and polymers containing same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5346811B2 (enrdf_load_stackoverflow) * | 1971-08-26 | 1978-12-16 | ||
| IL41330A (en) * | 1973-01-17 | 1975-07-28 | Imi Inst For Res & Dev | Solid catalyst for heterogeneous reactions |
| JPS52151106A (en) * | 1976-06-08 | 1977-12-15 | Cosmo Co Ltd | Hydration of lower olefins |
| US4065512A (en) * | 1976-07-06 | 1977-12-27 | Petro-Tex Chemical Corporation | Iso-C4 compound reactions with perfluorosulfonic acid resin catalysts |
-
1981
- 1981-07-28 IT IT23203/81A patent/IT1189022B/it active
- 1981-08-11 GB GB8124554A patent/GB2082178B/en not_active Expired
- 1981-08-12 BE BE0/205652A patent/BE889943A/fr not_active IP Right Cessation
- 1981-08-13 DE DE19813131975 patent/DE3131975A1/de active Granted
- 1981-08-14 FR FR8115746A patent/FR2488600B1/fr not_active Expired
- 1981-08-17 NL NL8103846A patent/NL8103846A/nl not_active Application Discontinuation
- 1981-08-17 CA CA000384027A patent/CA1180355A/fr not_active Expired
- 1981-08-18 JP JP56128262A patent/JPS5759823A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2082178A (en) | 1982-03-03 |
| JPH0351693B2 (enrdf_load_stackoverflow) | 1991-08-07 |
| GB2082178B (en) | 1984-07-11 |
| IT8123203A0 (it) | 1981-07-28 |
| FR2488600B1 (fr) | 1987-08-14 |
| FR2488600A1 (fr) | 1982-02-19 |
| CA1180355A (fr) | 1985-01-02 |
| IT1189022B (it) | 1988-01-28 |
| DE3131975A1 (de) | 1982-04-01 |
| DE3131975C2 (enrdf_load_stackoverflow) | 1988-01-21 |
| BE889943A (fr) | 1982-02-12 |
| JPS5759823A (en) | 1982-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |