US3867475A - Isoparaffin alkylation - Google Patents
Isoparaffin alkylation Download PDFInfo
- Publication number
- US3867475A US3867475A US343322A US34332273A US3867475A US 3867475 A US3867475 A US 3867475A US 343322 A US343322 A US 343322A US 34332273 A US34332273 A US 34332273A US 3867475 A US3867475 A US 3867475A
- Authority
- US
- United States
- Prior art keywords
- carbon dioxide
- acid
- alkylation
- psig
- range
- 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 - Lifetime
Links
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 53
- 230000029936 alkylation Effects 0.000 title description 24
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 100
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 50
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 49
- 239000003377 acid catalyst Substances 0.000 claims abstract description 27
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 15
- -1 olefin hydrocarbon Chemical class 0.000 claims abstract description 10
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 9
- 239000002168 alkylating agent Substances 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 46
- 150000002430 hydrocarbons Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- 239000001282 iso-butane Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 6
- 230000006872 improvement Effects 0.000 claims description 5
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 13
- 150000008051 alkyl sulfates Chemical class 0.000 abstract description 3
- 229960004424 carbon dioxide Drugs 0.000 description 43
- 239000003054 catalyst Substances 0.000 description 18
- 150000001336 alkenes Chemical class 0.000 description 14
- 239000007788 liquid Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 8
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical class CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HWBLTYHIEYOAOL-UHFFFAOYSA-N Diisopropyl sulfate Chemical compound CC(C)OS(=O)(=O)OC(C)C HWBLTYHIEYOAOL-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- UXLGPJLQZVPSSD-UHFFFAOYSA-N bis(2-methylpropyl) sulfate Chemical compound CC(C)COS(=O)(=O)OCC(C)C UXLGPJLQZVPSSD-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002968 pentalenes Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/03—Acids of sulfur other than sulfhydric acid or sulfuric acid, e.g. halosulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
Definitions
- Benefits of the present invention are obtained by dissolving carbon dioxide into the liquid strong acid catalyst. Maximum benefits are obtained when the strong acid is saturated with carbon dioxide at the alkylation reaction conditions employed. In order to encourage solution of carbon dioxide in strong acid, it is usually desirable to employ an excess of carbon dioxide. In treating the strong acid, weight ratios of carbon dioxide to strong acid of about 0.1/100 and higher may be employed. Preferably weight ratios of carbon dioxide to strong acid of at least 5/100 are employed. Great excesses of carbon dioxide to strong acid in the acid treatment are not necessary,
- Contact time of carbon dioxide with strong acid being treated need only be sufficient for solution of the desired amount of carbon dioxideint'o the strong acid. Contact times of from a few seconds to 24 hours and longer may be employed. Necessary contact time will be shorter with better mixing and more intimate contact of carbon dioxide with the strong acid. Preferred contact times for any particular acid treating system may be easily established by observing the rate of solution of carbon dioxide into the strong acid under the conditions of pressure, temperature and degree of mixing present in the particular system under consideration.
- alkylation reactions contemplated in the present invention are carried out in the liquid phase.
- the reactants need not be normally liquid hydrocarbons.
- Alkylation reaction conditions can vary in temperature from below zero to about 100F., and can be carried out at pressures of from atmospheric to 1000 psig and higher.
- olefin space velocities of from about 0.01 to about volumes olefin/hour/volume of catalyst may be employed.
- Molar ratios of isoparaffin hydrocarbonto alkylati'ng agent of from about 1:1 to about 50:1 and higher may be emloyed.
- substantial molar excess of isoparaffin to olefin is maintained in an alkylation reaction, with molar ratios of isoparaffin to olefin of'from about 5:1 to about 20:1 being particularly preferred.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US343322A US3867475A (en) | 1973-03-21 | 1973-03-21 | Isoparaffin alkylation |
| JP49009021A JPS5227121B2 (ja) | 1973-03-21 | 1974-01-22 | |
| GB556074A GB1447565A (en) | 1973-03-21 | 1974-02-06 | Isoparaffin alkylation |
| FR7406270A FR2222335B1 (ja) | 1973-03-21 | 1974-02-25 | |
| BE141530A BE811734A (fr) | 1973-03-21 | 1974-02-28 | Procede d'alkylation |
| DE2411102A DE2411102A1 (de) | 1973-03-21 | 1974-03-08 | Verfahren zum alkylieren von isoparaffinen mit alkylierungsmitteln in gegenwart eines stark sauren katalysators |
| CA194,762A CA1030560A (en) | 1973-03-21 | 1974-03-12 | Isoparaffin alkylation |
| NL7403476A NL7403476A (ja) | 1973-03-21 | 1974-03-15 | |
| IT12658/74A IT1051202B (it) | 1973-03-21 | 1974-03-25 | Procedimento di alchilazione di isoparaffine con olefine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US343322A US3867475A (en) | 1973-03-21 | 1973-03-21 | Isoparaffin alkylation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/484,095 Division US3972786A (en) | 1974-06-28 | 1974-06-28 | Mechanically enhanced magnetic memory |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3867475A true US3867475A (en) | 1975-02-18 |
Family
ID=23345629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US343322A Expired - Lifetime US3867475A (en) | 1973-03-21 | 1973-03-21 | Isoparaffin alkylation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3867475A (ja) |
| JP (1) | JPS5227121B2 (ja) |
| BE (1) | BE811734A (ja) |
| CA (1) | CA1030560A (ja) |
| DE (1) | DE2411102A1 (ja) |
| FR (1) | FR2222335B1 (ja) |
| GB (1) | GB1447565A (ja) |
| IT (1) | IT1051202B (ja) |
| NL (1) | NL7403476A (ja) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984352A (en) * | 1974-05-06 | 1976-10-05 | Mobil Oil Corporation | Catalyst containing a Lewis acid intercalated in graphite |
| US4008178A (en) * | 1974-11-04 | 1977-02-15 | Texaco Inc. | Alkylation catalyst for production of motor fuels |
| US4038212A (en) * | 1975-03-24 | 1977-07-26 | Texaco Inc. | Alkylation process for production of motor fuels |
| US5179052A (en) * | 1991-03-04 | 1993-01-12 | Texaco Chemical Company | One step synthesis of metyl t-butyl ether from 5-butanol using fluorosulfonic acid-modified zeolite catalysts |
| KR100332222B1 (ko) * | 1999-06-17 | 2002-04-12 | 유승렬 | 중질 알킬레이트의 제조방법 및 이의 용도 |
| US20100076241A1 (en) * | 2008-09-19 | 2010-03-25 | Loescher Mitchell E | Process for the alkylation of isobutane with dilute propylene |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2286184A (en) * | 1938-05-14 | 1942-06-16 | Union Oil Co | Process for producing paraffinic hydrocarbons |
| US2468529A (en) * | 1945-12-13 | 1949-04-26 | Standard Oil Dev Co | Alkylation process |
| US2520391A (en) * | 1947-01-20 | 1950-08-29 | Phillips Petroleum Co | Liquid-liquid contacting |
| US3489818A (en) * | 1968-12-27 | 1970-01-13 | Universal Oil Prod Co | Temperature control of alkylation reactions |
| US3531546A (en) * | 1967-11-29 | 1970-09-29 | Universal Oil Prod Co | Alkylation of organic compounds |
-
1973
- 1973-03-21 US US343322A patent/US3867475A/en not_active Expired - Lifetime
-
1974
- 1974-01-22 JP JP49009021A patent/JPS5227121B2/ja not_active Expired
- 1974-02-06 GB GB556074A patent/GB1447565A/en not_active Expired
- 1974-02-25 FR FR7406270A patent/FR2222335B1/fr not_active Expired
- 1974-02-28 BE BE141530A patent/BE811734A/xx unknown
- 1974-03-08 DE DE2411102A patent/DE2411102A1/de active Pending
- 1974-03-12 CA CA194,762A patent/CA1030560A/en not_active Expired
- 1974-03-15 NL NL7403476A patent/NL7403476A/xx not_active Application Discontinuation
- 1974-03-25 IT IT12658/74A patent/IT1051202B/it active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2286184A (en) * | 1938-05-14 | 1942-06-16 | Union Oil Co | Process for producing paraffinic hydrocarbons |
| US2468529A (en) * | 1945-12-13 | 1949-04-26 | Standard Oil Dev Co | Alkylation process |
| US2520391A (en) * | 1947-01-20 | 1950-08-29 | Phillips Petroleum Co | Liquid-liquid contacting |
| US3531546A (en) * | 1967-11-29 | 1970-09-29 | Universal Oil Prod Co | Alkylation of organic compounds |
| US3489818A (en) * | 1968-12-27 | 1970-01-13 | Universal Oil Prod Co | Temperature control of alkylation reactions |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984352A (en) * | 1974-05-06 | 1976-10-05 | Mobil Oil Corporation | Catalyst containing a Lewis acid intercalated in graphite |
| US4008178A (en) * | 1974-11-04 | 1977-02-15 | Texaco Inc. | Alkylation catalyst for production of motor fuels |
| US4038212A (en) * | 1975-03-24 | 1977-07-26 | Texaco Inc. | Alkylation process for production of motor fuels |
| US5179052A (en) * | 1991-03-04 | 1993-01-12 | Texaco Chemical Company | One step synthesis of metyl t-butyl ether from 5-butanol using fluorosulfonic acid-modified zeolite catalysts |
| KR100332222B1 (ko) * | 1999-06-17 | 2002-04-12 | 유승렬 | 중질 알킬레이트의 제조방법 및 이의 용도 |
| US20100076241A1 (en) * | 2008-09-19 | 2010-03-25 | Loescher Mitchell E | Process for the alkylation of isobutane with dilute propylene |
| WO2010033273A1 (en) * | 2008-09-19 | 2010-03-25 | Catalytic Distillation Technologies | Process for the alkylation of isobutane with dilute propylene |
| US8034988B2 (en) | 2008-09-19 | 2011-10-11 | Catalytic Distillation Technologies | Process for the alkylation of isobutane with dilute propylene |
| EA017873B1 (ru) * | 2008-09-19 | 2013-03-29 | Каталитик Дистиллейшн Текнолоджиз | Способ алкилирования изобутана разбавленным пропиленом |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2222335B1 (ja) | 1978-01-06 |
| IT1051202B (it) | 1981-04-21 |
| JPS5227121B2 (ja) | 1977-07-19 |
| NL7403476A (ja) | 1974-09-24 |
| FR2222335A1 (ja) | 1974-10-18 |
| JPS49125301A (ja) | 1974-11-30 |
| CA1030560A (en) | 1978-05-02 |
| GB1447565A (en) | 1976-08-25 |
| DE2411102A1 (de) | 1974-09-26 |
| BE811734A (fr) | 1974-08-28 |
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