GB734128A - - Google Patents
Info
- Publication number
- GB734128A GB734128A GB734128DA GB734128A GB 734128 A GB734128 A GB 734128A GB 734128D A GB734128D A GB 734128DA GB 734128 A GB734128 A GB 734128A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkylation
- reaction
- catalyst
- reactants
- alkali metal
- 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
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
- C07C2/72—Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
- C07C2523/04—Alkali metals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
734,128. Alkylation of carbocyclic hydrocarbons. ETHYL CORPORATION. Nov. 6, 1952 [March 29, 1952], No. 27967/52. Class 2 (3). [Also in Group VI]- A carbocyclic hydrocarbon containing a saturated tertiary carbon atom adjacent to an unsaturated nuclear carbon atom and having attached thereto one hydrogen atom is alkylated by reacting with a non-conjugated olefin at elevated temperature in the presence of an alkali metal as catalyst. The alkylation yields products in which the hydrogen on the tertiary carbon atom is replaced by an organic radical derived from the alkylating olefin and containing the same number of carbon atoms as the olefin. The carbocyclic hydrocarbon may be aromatic or it may be an alicyclic or hydroaromatic hydrocarbon containing ring unsaturation and having alpha to a ring unsaturation a tertiary saturated carbon atom either nuclear or extranuclear attached to only one hydrogen atom. The catalyst may comprise any alkali metal or mixture of alkali metals, thus lithium, sodium, potassium, rubidium and caesium may be used. The alkali metal is preferably used in the form of a dispersion but molten alkali metal or massive solid alkali metal can also be used. The catalyst may also be mixed with a relatively inert material such as calcium, a preferred form of such mixtures being the socalled " sludge " obtained in the production of sodium by electrolysis of a sodium chloridecalcium chloride mixture. The reaction should preferably be carried out in substantially oxygen-free surroundings and the reactants should be low, e.g. below 0.5 per cent, in oxygen content. Specified reaction temperatures are from about 150‹ to 500‹ C. and the reaction pressures may be from 2 to 3000 atmospheres. Higher pressures favour a higher degree of alkylation, e.g. dialkylation of p.-diisopropyl benzene with ethylene to form p-di-(tert.-amyl)- benzene, whilst lower pressures favour lower degrees of alkylation, e.g. monoalkylation in the latter reaction to form p-isopropyl (tert.- amyl)-benzene. Mixtures of olefines and/or of the carbocyclic hydrocarbons may be used and either or both of the reactants may be dissolved in an inert solvent, e.g. a paraffin, cycloparaffin or an aromatic solvent containing no hydrogen-bearing carbon atoms alpha to an aromatic nucleus. As one of the latter type of aromatic solvents one of the reaction products, e.g. di-(tert.-amyl)-benzene may be employed. The process may be carried out batchwise or in a continuous manner. In the latter case the reactants in liquid or vapour state or in mixed liquid-vapour state may be passed over a fixed bed of catalyst which may be admixed with an inert carrier or the liquid or liquid-vapour reaction can be carried out in the presence of a suspended catalyst which is transported through the reaction zone by the velocity of liquid reactants and products. The reactants may be diluted with inert gases such as propane, ethane, methane, nitrogen, helium and neon. Carbocyclic hydrocarbons in which the carbon atom alkylated is cyclic include 3,6-dimethylcyclohexene, 1,4 - di - ethyl - 1,2,3,4 - tetrahydronaphthalene, 1,3 - dimethylhydrindene, and 3,5-dimethylcyclopentene and examples of compounds which undergo alkylation of acyclic carbon atoms are cumene, diisopropylbenzene, sec.-butylbenzene, 2-phenylpentane, 3-phenylpentane, isopropylnaphthalenes, isopropyl anthracenes, sec.-butyl phenanthrenes, 1,1-diphenylethane, 2-phenyldodecane and isopropyltert.-butylbenzenes. Compounds which undergo either cyclic or acyclic alkylation, or both, include 1,4-dimethyl-1,2,3,4-tetrahydro-5-isopropylnaphthalene. The alkylating agent is preferably a non-cyclic mono-olefine, e.g. ethylene, propylene, butene-1, butene-2, pentene-1, pentene-2, hexene-1, hexene-2, hexene- 3, a heptene, octene, nonene, decene, undecene, or dodecene, isobutylene, 3-methylheptene-1, 2-ethyl-pentene-1, or 3-methyl-hexene-3. Other olefins which may be used are cyclic olefins, non-conjugated polyolefines and mono-olefines of more than 12 carbon atoms, e.g. cyclohexene, cyclopentene, 1,4-cyclohexadiene, 1,4- or 1,5- hexadiene, tetradecenes, and pentadecenes, e.g. pentadecene-1. The products obtained by alkylating various carbocyclic hydrocarbons with various olefines are specified. Examples describe the alkylation of isopropylbenzene with ethylene to form tert.-amylbenzene using potassium and sodium respectively in the form of a fine dispersion as catalyst. It is stated that the products of the invention are useful in the formation of synthetic detergents, as solvents, as constituents of blended fuels and as constituents of insecticidal compositions.
Publications (1)
Publication Number | Publication Date |
---|---|
GB734128A true GB734128A (en) | 1900-01-01 |
Family
ID=1751315
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB734128D Expired GB734128A (en) |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB734128A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2863930A (en) * | 1956-02-28 | 1958-12-09 | American Cyanamid Co | Alkylation of ditolylalkanes |
US4950831A (en) * | 1989-09-28 | 1990-08-21 | Ethyl Corporation | Coupling process |
-
0
- GB GB734128D patent/GB734128A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2863930A (en) * | 1956-02-28 | 1958-12-09 | American Cyanamid Co | Alkylation of ditolylalkanes |
US4950831A (en) * | 1989-09-28 | 1990-08-21 | Ethyl Corporation | Coupling process |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3327015A (en) | Olefin dimerization by nickel compounds | |
KR100803431B1 (en) | Process for the production of linear alpha olefins and ethylene | |
US2986588A (en) | Propylene dimerization | |
US4511748A (en) | Process for producing alkylbenzenes | |
US2994725A (en) | Organic chemical reactions | |
US2728802A (en) | Catalytic alkylation process | |
US3341614A (en) | Production of detergent alkylate | |
US2721886A (en) | Catalyzed condensation of aromatic compounds with unsaturated organic compounds | |
US3459826A (en) | Olefin oligomerization | |
US2748178A (en) | Condensation of an aromatic compound with an unsaturated organic compound in the presence of an alkali metal and a peroxy compound | |
GB734128A (en) | ||
US2849508A (en) | Side chain alkylation of alkylaromatics with olefins using an organometallic compound as catalyst | |
US2769850A (en) | Alkylation reactions | |
US2315078A (en) | Conversion of hydrocarbons | |
US2688044A (en) | Condensation of aromatic compounds with unsaturated organic compounds in the presence of mixed catalysts | |
US4524230A (en) | Preparation of alkylaromatic compounds | |
US2984691A (en) | Telomerization process | |
US2357978A (en) | Alkylation of aromatic hydrocarbons | |
US3028441A (en) | Alkali metal-catalyzed olefinic condensation | |
US3277196A (en) | Alkylation process | |
US3267170A (en) | Process for forming olefins by hydrogen transfer | |
US3773843A (en) | Alkylation of saturated hydrocarbons | |
US2721885A (en) | Condensation of aromatic compounds with unsaturated organic compounds in the presence of composite catalysts | |
US3624177A (en) | Oligomerization of olefins | |
US2823240A (en) | Alkylation of alkyl aromatic hydrocarbons to produce indanes |