GB421118A - 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
- GB421118A GB421118A GB1336233A GB1336233A GB421118A GB 421118 A GB421118 A GB 421118A GB 1336233 A GB1336233 A GB 1336233A GB 1336233 A GB1336233 A GB 1336233A GB 421118 A GB421118 A GB 421118A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isobutylene
- chloride
- solid
- liquid
- temperature
- 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 12
- 229930195733 hydrocarbon Natural products 0.000 title abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 14
- 239000007788 liquid Substances 0.000 abstract 8
- 239000007787 solid Substances 0.000 abstract 7
- 150000004820 halides Chemical class 0.000 abstract 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 4
- 239000010687 lubricating oil Substances 0.000 abstract 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 2
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000000571 coke Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 239000012188 paraffin wax Substances 0.000 abstract 2
- 230000000737 periodic effect Effects 0.000 abstract 2
- 230000000630 rising effect Effects 0.000 abstract 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 abstract 1
- JCMGUODNZMETBM-UHFFFAOYSA-N arsenic trifluoride Chemical compound F[As](F)F JCMGUODNZMETBM-UHFFFAOYSA-N 0.000 abstract 1
- 229910001627 beryllium chloride Inorganic materials 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- -1 lubricating oils Chemical class 0.000 abstract 1
- 229910052762 osmium Inorganic materials 0.000 abstract 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- SANRKQGLYCLAFE-UHFFFAOYSA-H uranium hexafluoride Chemical compound F[U](F)(F)(F)(F)F SANRKQGLYCLAFE-UHFFFAOYSA-H 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 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
- C07C2/22—Metal halides; 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
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Hydrocarbons of high molecular weight are manufactured by subjecting isobutylene in the liquid state to the action of gaseous or solid volatile halides of groups II, V, VI and VIII of the periodic system or of liquid volatile halides at temperatures above -10 DEG C., e.g., at ordinary or elevated temperatures. Suitable gaseous or solid volatile halides are beryllium chloride, zinc chloride, phosphorus pentafluoride, arsenic fluoride, uranium hexafluoride, ferric chloride and osmium octafluoride. As liquid volatile halides may be employed those which are liquid at room or slightly increased temperature, e.g., 40 DEG C., such as boron chloride, tin tetrachloride, titanium tetrachloride, anhydrous hydrofluoric acid and antimony pentafluoride. Alternatively aluminium chloride may be employed if care is taken that the temperature does not exceed 50 DEG C., during the substantial part of the reaction. The aluminium chloride may be in the form of aluminium activated with mercury chloride with the addition of sufficient amounts of hydrogen chloride. The isobutylene may be polymerized in bulk or in the dissolved or emulsified state. The products may be added to solid or liquid hydrocarbons, e.g., lubricating oils, in order to improve their viscosity, disruptive strength, setting point and coke test. A table shows the effect on the viscosity of two lubricating oils of products obtained by polymerizing isobutylene by the action of: (a) boron chloride at 100 DEG C., under pressure; (b) aluminium chloride at 20 DEG C., under pressure; (c) titanium tetrachloride under the same conditions; (d) titanium chloride at 50 DEG C. under pressure; (e) boron fluoride, led into boiling isobutylene, the temperature being allowed to rise. The products may also be added to paraffin wax, benzine and solid greases. In examples: (1) isobutylene is treated with boron trichloride in an autoclave at 100 DEG C.; (2) isobutylene is treated with titanium tetrachloride at 20 DEG C., in a water-cooled autoclave; (3) isobutylene and tin tetrachloride are allowed to stand at room temperature in a closed flask, and the product is fractionated under reduced pressure; (4) boiling isobutylene is stirred with aluminium chloride, the temperature rising and reaching about 70 DEG C. at the end; the product is partly distilled off; (5) aluminium chloride is added gradually to a solution of isobutylene in pentane at 15 DEG C., under a reflux condenser at -5 DEG C.; the product is fractionated under reduced pressure; (6) isobutylene is charged into an autoclave and there is introduced aluminium chloride fused into a reagent glass which is broken at 20 DEG C., the temperature rising during the reaction to 50 DEG C.; part of the product is distilled off under reduced pressure. Specifications 358,068; 399,527, [Group III], and 401,297 are referred to.ALSO:Solid or liquid hydrocarbons are improved in respect of viscosity, disruptive strength, setting point and coke test by the addition of hydrocarbons of high molecular weight obtained by subjecting isobutylene in the liquid state to the action of gaseous or solid volatile halides of groups II, V, VI, and VIII of the periodic system or of liquid volatile halides at temperatures above 10 DEG C., or to the action of aluminium chloride while taking care that the temperature does not exceed 50 DEG C., during the substantial part of the reaction. A table shows the effect of certain of these products on the viscosity of two lubricating oils. The products may also be added to paraffin wax, benzine and solid greases. Specifications 358,068, 399,527, and 401,297 are referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1336233A GB421118A (en) | 1933-05-08 | 1933-05-08 | 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 |
---|---|---|---|
GB1336233A GB421118A (en) | 1933-05-08 | 1933-05-08 | Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutylene |
Publications (1)
Publication Number | Publication Date |
---|---|
GB421118A true GB421118A (en) | 1934-12-10 |
Family
ID=10021567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1336233A Expired GB421118A (en) | 1933-05-08 | 1933-05-08 | Improvements in the manufacture and production of hydrocarbons of high molecular weight from isobutylene |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB421118A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE746304C (en) * | 1937-07-07 | 1944-07-21 | Ig Farbenindustrie Ag | Process for the production of hydrocarbon oils suitable as insulating oils |
US2431549A (en) * | 1942-02-10 | 1947-11-25 | Phillips Petroleum Co | Conversion of olefins with hydrogen fluoride catalyst |
US3361840A (en) * | 1963-06-27 | 1968-01-02 | Shell Oil Co | Process for preparing dimers and co-dimers of olefins |
-
1933
- 1933-05-08 GB GB1336233A patent/GB421118A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE746304C (en) * | 1937-07-07 | 1944-07-21 | Ig Farbenindustrie Ag | Process for the production of hydrocarbon oils suitable as insulating oils |
US2431549A (en) * | 1942-02-10 | 1947-11-25 | Phillips Petroleum Co | Conversion of olefins with hydrogen fluoride catalyst |
US3361840A (en) * | 1963-06-27 | 1968-01-02 | Shell Oil Co | Process for preparing dimers and co-dimers of olefins |
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