GB401297A - Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutylene - Google Patents
Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutyleneInfo
- Publication number
- GB401297A GB401297A GB644432A GB644432A GB401297A GB 401297 A GB401297 A GB 401297A GB 644432 A GB644432 A GB 644432A GB 644432 A GB644432 A GB 644432A GB 401297 A GB401297 A GB 401297A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isobutylene
- boron fluoride
- iso
- carbon dioxide
- cooled
- 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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title abstract 8
- 229930195733 hydrocarbon Natural products 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 2
- 150000002430 hydrocarbons Chemical class 0.000 title 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 10
- 229910015900 BF3 Inorganic materials 0.000 abstract 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 6
- 239000001569 carbon dioxide Substances 0.000 abstract 5
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- 238000005336 cracking Methods 0.000 abstract 4
- 239000007787 solid Substances 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 229910001502 inorganic halide Inorganic materials 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 235000019271 petrolatum Nutrition 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 230000000379 polymerizing effect Effects 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 abstract 1
- 229960005215 dichloroacetic acid Drugs 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229940057995 liquid paraffin Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- -1 naphthene hydrocarbons Chemical class 0.000 abstract 1
- 239000003345 natural gas Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 238000013021 overheating Methods 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 abstract 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 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
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
-
- 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
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
High molecular polymerization products are manufactured by polymerizing iso-olefines in the presence of an inorganic halide, preferably volatile, while maintaining the temperature continuously below -10 DEG C. Suitable inorganic halides are boron fluoride, boron fluoride charged with hydrofluoric acid, phosphorus trifluoride or pentafluoride, aluminium chloride, preferably in statu nascendi, e.g. as formed by the action of hydrogen chloride on aluminium, or solutions or double compounds p of the said halides, e.g. solutions in substances such as phenol or cresol in which they dissolve without decomposition whether with the formation of real solutions or of double compounds. Preferably the catalyst is brought into contact with the iso-olefine gradually, advantageously while moving the iso-olefine, e.g. by stirring, in order to avoid local overheating. The cooling may be effected externally by means of cooling baths or internally by adding to the reacting substances cold materials which have no unfavourable influence, e.g. solid carbon dioxide. The catalysts may be employed in very small amounts, e.g. less than 1 per cent in the case of boron fluoride, though higher percentages may be used, e.g. 3 or 5 per cent of aluminium chloride. Solvents, e.g. pentane, may be present during the reaction. The process is applicable particularly to the treatment of isobutylene, but also to the polymerization of other iso-olefines or products containing iso-olefines, e.g. cracking products which are liquid at ordinary temperatures, such as those obtained by cracking solid or liquid paraffin or naphthene hydrocarbons, e.g. hard or soft paraffin waxes, ceresine, heavy and middle oils, paraffin and petroleum fractions. In examples: (1) boron fluoride is led into liquid isobutylene cooled in a bath of carbon dioxide to -80 DEG C.; (2) as in (1) except that the reaction material is cooled to -60 to -70 DEG C. by throwing in solid carbon dioxide; (3) boron fluoride is led into a solution of isobutylene in pentane at -40 DEG C.; (4) and (5) mixtures of isobutylene and normal butylene are treated as in (2), the isobutylene being polymerized; (6) a mixture of natural gas gasoline, isobutylene and normal butylene is polymerized as in (2); the molecular weight of the product may be increased by depolymerizing by heating, if desired in the presence of catalysts, e.g. by heating to 300 DEG C. in the presence of phosphoric acid, and again polymerizing; (7) titanium chloride is added at intervals to isobutylene cooled with solid carbon dioxide; (8) as in (7) except that all the titanium chloride is added at the beginning; the reaction temperature is -80 DEG C.; (9) boron fluoride is led into a soft paraffin wax cracking product cooled initially to -60 DEG C. by acetone and carbon dioxide, the temperature not being allowed to exceed -40 DEG C.; (10) aluminium chips and mercury chloride are added to a cracking product as in (9), cooled initially to -20 DEG C., and hydrogen chloride gas is led in, the temperature not being allowed to exceed -15 DEG C. Specification 358,068 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB644432A GB401297A (en) | 1932-03-03 | 1932-03-03 | Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutylene |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB644432A GB401297A (en) | 1932-03-03 | 1932-03-03 | Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutylene |
Publications (1)
Publication Number | Publication Date |
---|---|
GB401297A true GB401297A (en) | 1933-11-03 |
Family
ID=9814584
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB644432A Expired GB401297A (en) | 1932-03-03 | 1932-03-03 | Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutylene |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB401297A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2471890A (en) * | 1946-06-22 | 1949-05-31 | Standard Oil Dev Co | Polymerization of isobutylene in the presence of controlled amounts of promoters for the reaction |
US2856370A (en) * | 1953-09-09 | 1958-10-14 | Du Pont | Process for polymerizing cyclic ethers with phosphorous pentafluoride |
EP1598380A1 (en) * | 2004-05-19 | 2005-11-23 | Basf Aktiengesellschaft | Isobutene polymerisation in the presence of complexes of donor and fluor containing acid |
-
1932
- 1932-03-03 GB GB644432A patent/GB401297A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2471890A (en) * | 1946-06-22 | 1949-05-31 | Standard Oil Dev Co | Polymerization of isobutylene in the presence of controlled amounts of promoters for the reaction |
US2856370A (en) * | 1953-09-09 | 1958-10-14 | Du Pont | Process for polymerizing cyclic ethers with phosphorous pentafluoride |
EP1598380A1 (en) * | 2004-05-19 | 2005-11-23 | Basf Aktiengesellschaft | Isobutene polymerisation in the presence of complexes of donor and fluor containing acid |
WO2005116094A1 (en) * | 2004-05-19 | 2005-12-08 | Basf Aktiengesellschaft | Isobutene polymerisation in the presence of a donor and fluorinated acids complex |
US7932332B2 (en) | 2004-05-19 | 2011-04-26 | Basf Aktiengesellschaft | Isobutene polymerisation in the presence of a donor and fluorinated acids complex |
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