GB1046099A - Continuous process for alkylating an aromatic hydrocarbon - Google Patents
Continuous process for alkylating an aromatic hydrocarbonInfo
- Publication number
- GB1046099A GB1046099A GB27261/64A GB2726164A GB1046099A GB 1046099 A GB1046099 A GB 1046099A GB 27261/64 A GB27261/64 A GB 27261/64A GB 2726164 A GB2726164 A GB 2726164A GB 1046099 A GB1046099 A GB 1046099A
- Authority
- GB
- United Kingdom
- Prior art keywords
- zone
- red oil
- paraffin
- aromatic hydrocarbon
- feed
- 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
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
-
- 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
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/901—Catalyst and recycle considerations with recycle, rehabilitation, or preservation of solvent, diluent, or mass action agent
- Y10S585/902—Recycle of solvent and catalyst
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/904—Catalyst rehabilitation by reversion from different compound
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/905—Catalyst and recycle considerations by-product conversion to feed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Detergent alkylate is obtained by contacting an excess of aromatic hydrocarbon with a C9-C18 alkyl chloride in a first zone in the presence of a red oil complex catalyst to effect condensation of a major proportion of the alkyl chloride, separating red oil from the effluent and contacting the remainder in a second zone with aluminium to complete condensation, separating red oil from the effluent for use as catalyst in the first zone and recovering alkylate from the remainder. In a preferred embodiment partially chlorinated n-paraffin containing 10-50% mol. of alkyl chloride together wit fresh feed n-paraffin boiling in the range 300-605 DEG F. and 2-25 mols. of aromatic hydrocarbon per mol. of chloride are contacted with red oil complex forming 5-25% by volume of the reaction mixture are contacted in the first zone at 100-185 DEG F. for 3-15 minutes to condense 90-95% of the alkyl chloride. Part of the red oil complex is recycled and an amount equivalent to that from the second zone is discarded. Hydrogen chloride may also be separated and washed with the n-paraffin feed to recover organic compounds. Consumption of aluminium in the second zone is regulated either by using a zone packed with metal and limiting the amount of hydrogen chloride introduced, e.g. 1-30 parts per 1000 parts of feed or a saturated solution, or by feeding aluminium at a controlled rate of 0.03-0.1 gram atom per gram atom of chlorine in the chlorinated paraffin feed to the first zone. Red oil may be maintained in an amount of 5-25% vol. of the reaction mixture. Reaction is effected at 100-185 DEG F. for 0.3-15 minutes. Red oil is separated and passed to the first reactor and/or recycled to the second. The product is separated into aromatic hydrocarbon for recycle, n-paraffin which is partially chlorinated and passed to the first zone and alkylate boiling in the range 520-730 DEG F.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US292578A US3355508A (en) | 1963-07-03 | 1963-07-03 | Continuous process for alkylating an aromatic hydrocarbon |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1046099A true GB1046099A (en) | 1966-10-19 |
Family
ID=23125280
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27261/64A Expired GB1046099A (en) | 1963-07-03 | 1964-07-01 | Continuous process for alkylating an aromatic hydrocarbon |
Country Status (3)
Country | Link |
---|---|
US (1) | US3355508A (en) |
DE (1) | DE1443648B2 (en) |
GB (1) | GB1046099A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1093994A (en) * | 1966-07-12 | 1967-12-06 | Shell Int Research | A process for preparing detergent alkylate |
US3538177A (en) * | 1968-09-25 | 1970-11-03 | Continental Oil Co | Preparation of high molecular weight dialkyl aromatic compounds |
US3494971A (en) * | 1969-04-18 | 1970-02-10 | Universal Oil Prod Co | Process for the production of a monoalkylated aromatic hydrocarbon |
US3671601A (en) * | 1970-09-03 | 1972-06-20 | Continental Oil Co | Process for the purification of alkylate |
US3674885A (en) * | 1970-10-09 | 1972-07-04 | Atlantic Richfield Co | Alkylation of benzene utilizing fischer-tropsch olefin-paraffin mixtures |
IT946067B (en) * | 1971-11-17 | 1973-05-21 | Sir Soc Italiana Resine Spa | IMPROVEMENTS IN THE ALKYLATION PROCEDURES |
US20030105352A1 (en) * | 2001-08-03 | 2003-06-05 | Dado Gregory P. | Arylalkylsulfonic acids and methods for producing same |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1995827A (en) * | 1933-08-28 | 1935-03-26 | Sharples Solvents Corp | Production of alkyl substituted aryl hydrocarbons |
US2057306A (en) * | 1934-04-24 | 1936-10-13 | Martin Friedrich | Aluminum catalyst |
US2078238A (en) * | 1935-05-07 | 1937-04-27 | Dow Chemical Co | Separation of ethylene from its homologues |
US2233408A (en) * | 1938-03-11 | 1941-03-04 | Nat Aniline & Chem Co Inc | Method of producing higher alkyl aromatic sulphonates |
US2244512A (en) * | 1939-03-04 | 1941-06-03 | Preparation of aliphatic-aromatic | |
US2388428A (en) * | 1943-03-31 | 1945-11-06 | Universal Oil Prod Co | Catalysis of organic reactions |
US2740807A (en) * | 1951-04-09 | 1956-04-03 | Ruhrchemie Ag | Preparation of pure white alkyl aryl sulfonates |
US3169987A (en) * | 1960-12-30 | 1965-02-16 | Universal Oil Prod Co | Alkaryl sulfonate production via n-olefin isomerization |
US3078322A (en) * | 1961-03-08 | 1963-02-19 | Standard Oil Co | Hydrogen fluoride alkylation process |
-
1963
- 1963-07-03 US US292578A patent/US3355508A/en not_active Expired - Lifetime
-
1964
- 1964-07-01 GB GB27261/64A patent/GB1046099A/en not_active Expired
- 1964-07-02 DE DE19641443648 patent/DE1443648B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
DE1443648B2 (en) | 1973-08-23 |
US3355508A (en) | 1967-11-28 |
DE1443648A1 (en) | 1968-11-14 |
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