DE1493342C - - Google Patents
Info
- Publication number
- DE1493342C DE1493342C DE19641493342 DE1493342A DE1493342C DE 1493342 C DE1493342 C DE 1493342C DE 19641493342 DE19641493342 DE 19641493342 DE 1493342 A DE1493342 A DE 1493342A DE 1493342 C DE1493342 C DE 1493342C
- Authority
- DE
- Germany
- Prior art keywords
- line
- hydrogen fluoride
- alkylate
- alkylation
- per day
- 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 51
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 51
- 229930195733 hydrocarbon Natural products 0.000 claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 claims description 33
- 238000005804 alkylation reaction Methods 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 26
- 230000029936 alkylation Effects 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 54
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000001282 iso-butane Substances 0.000 description 27
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 24
- 239000001294 propane Substances 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 18
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 6
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 4
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 4
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IYLGZMTXKJYONK-ACLXAEORSA-N (12s,15r)-15-hydroxy-11,16-dioxo-15,20-dihydrosenecionan-12-yl acetate Chemical compound O1C(=O)[C@](CC)(O)C[C@@H](C)[C@](C)(OC(C)=O)C(=O)OCC2=CCN3[C@H]2[C@H]1CC3 IYLGZMTXKJYONK-ACLXAEORSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- -1 159 hl per day Chemical compound 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- HDGQICNBXPAKLR-UHFFFAOYSA-N 2,4-dimethylhexane Chemical compound CCC(C)CC(C)C HDGQICNBXPAKLR-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- RNTWWGNZUXGTAX-UHFFFAOYSA-N 3,4-dimethylhexane Chemical compound CCC(C)C(C)CC RNTWWGNZUXGTAX-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 description 2
- JXPOLSKBTUYKJB-UHFFFAOYSA-N xi-2,3-Dimethylhexane Chemical compound CCCC(C)C(C)C JXPOLSKBTUYKJB-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- XTDQDBVBDLYELW-UHFFFAOYSA-N 2,2,3-trimethylpentane Chemical compound CCC(C)C(C)(C)C XTDQDBVBDLYELW-UHFFFAOYSA-N 0.000 description 1
- OKVWYBALHQFVFP-UHFFFAOYSA-N 2,3,3-trimethylpentane Chemical compound CCC(C)(C)C(C)C OKVWYBALHQFVFP-UHFFFAOYSA-N 0.000 description 1
- RLPGDEORIPLBNF-UHFFFAOYSA-N 2,3,4-trimethylpentane Chemical compound CC(C)C(C)C(C)C RLPGDEORIPLBNF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- VLZZXGOEDAYHOI-UHFFFAOYSA-N ethyllead Chemical compound CC[Pb] VLZZXGOEDAYHOI-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- IYLGZMTXKJYONK-UHFFFAOYSA-N ruwenine Natural products O1C(=O)C(CC)(O)CC(C)C(C)(OC(C)=O)C(=O)OCC2=CCN3C2C1CC3 IYLGZMTXKJYONK-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US317262A US3249650A (en) | 1963-10-18 | 1963-10-18 | Isoparaffin alkylation process |
| US31726263 | 1963-10-18 | ||
| DEU0011137 | 1964-10-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1493342A1 DE1493342A1 (de) | 1969-01-23 |
| DE1493342C true DE1493342C (en, 2012) | 1973-07-05 |
Family
ID=23232862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641493342 Granted DE1493342A1 (de) | 1963-10-18 | 1964-10-19 | Verfahren zur Alkylierung von Isoparaffinen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3249650A (en, 2012) |
| AT (1) | AT257020B (en, 2012) |
| DE (1) | DE1493342A1 (en, 2012) |
| DK (1) | DK121364B (en, 2012) |
| ES (1) | ES305018A1 (en, 2012) |
| FI (1) | FI42708B (en, 2012) |
| FR (1) | FR1415911A (en, 2012) |
| GB (1) | GB1078123A (en, 2012) |
| NL (1) | NL144252B (en, 2012) |
| NO (1) | NO116161B (en, 2012) |
| SE (1) | SE304507B (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3371127A (en) * | 1965-01-29 | 1968-02-27 | Phillips Petroleum Co | Alkylation process with improvement in phase separation |
| US3456033A (en) * | 1967-02-28 | 1969-07-15 | Universal Oil Prod Co | Alkylation process utilizing an aircooled reactor |
| US3919343A (en) * | 1974-05-08 | 1975-11-11 | Universal Oil Prod Co | Isobutane-butylene alkylation process |
| US4046516A (en) * | 1975-12-29 | 1977-09-06 | Uop Inc. | Hydrogen fluoride-catalyzed alkylation apparatus |
| US4239931A (en) * | 1979-11-05 | 1980-12-16 | Uop Inc. | HF Alkylatior process |
| US4341911A (en) * | 1980-12-29 | 1982-07-27 | Uop Inc. | Hydrocarbon conversion process for the production of gasoline |
| US4503277A (en) * | 1983-11-30 | 1985-03-05 | Uop Inc. | HF regeneration in aromatic hydrocarbon alkylation process |
| US4774375A (en) * | 1987-12-11 | 1988-09-27 | Uop Inc. | HF alkylation and selective hydrogenation process |
| US5146036A (en) * | 1990-01-12 | 1992-09-08 | Phillips Petroleum Company | Transfer of catalyst |
| US5021223A (en) * | 1990-01-12 | 1991-06-04 | Phillips Petroleum Company | Transfer of catalyst |
| US5094823A (en) * | 1990-06-11 | 1992-03-10 | Phillips Petroleum Company | Combination acid recontactor-storage vessel |
| US7446238B2 (en) * | 2005-01-31 | 2008-11-04 | Uop Llc | Alkylation process with recontacting in settler |
| DE102007035500A1 (de) | 2007-07-28 | 2009-01-29 | Andreas Stihl Ag & Co. Kg | Kraftstoffzusammensetzung |
| US20090171133A1 (en) * | 2007-12-28 | 2009-07-02 | Chevron U.S.A. Inc. | Ionic liquid catalyst alkylation using a loop reactor |
| KR102012065B1 (ko) | 2013-04-19 | 2019-08-19 | 릴라이언스 인더스트리즈 리미티드 | 이온 액체 화합물 |
| US10246395B2 (en) | 2016-12-19 | 2019-04-02 | The Board Of Trustees Of The University Of Alabama | Methods of acylation with an ionic liquid catalyzing medium |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2317901A (en) * | 1940-03-11 | 1943-04-27 | Phillips Petroleum Co | Conversion of hydrocarbons |
| US2717913A (en) * | 1952-08-28 | 1955-09-13 | Exxon Research Engineering Co | Separation method for olefin alkylation |
| US2910522A (en) * | 1957-11-05 | 1959-10-27 | Universal Oil Prod Co | Extractive alkylation process |
-
1963
- 1963-10-18 US US317262A patent/US3249650A/en not_active Expired - Lifetime
-
1964
- 1964-10-16 SE SE12512/64A patent/SE304507B/xx unknown
- 1964-10-16 NL NL646412095A patent/NL144252B/xx unknown
- 1964-10-16 DK DK512964AA patent/DK121364B/da unknown
- 1964-10-17 NO NO155186A patent/NO116161B/no unknown
- 1964-10-17 ES ES0305018A patent/ES305018A1/es not_active Expired
- 1964-10-19 AT AT886664A patent/AT257020B/de active
- 1964-10-19 FI FI2194/64A patent/FI42708B/fi active
- 1964-10-19 FR FR991874A patent/FR1415911A/fr not_active Expired
- 1964-10-19 GB GB42468/64A patent/GB1078123A/en not_active Expired
- 1964-10-19 DE DE19641493342 patent/DE1493342A1/de active Granted
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