GB983376A - Process for the production of detergent alkylate - Google Patents

Process for the production of detergent alkylate

Info

Publication number
GB983376A
GB983376A GB39132/62A GB3913262A GB983376A GB 983376 A GB983376 A GB 983376A GB 39132/62 A GB39132/62 A GB 39132/62A GB 3913262 A GB3913262 A GB 3913262A GB 983376 A GB983376 A GB 983376A
Authority
GB
United Kingdom
Prior art keywords
fraction
dimerization
recovered
propylene
normal
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
Application number
GB39132/62A
Inventor
Wilfred John Oldham
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
British Hydrocarbon Chemicals Ltd
Original Assignee
British Hydrocarbon Chemicals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to NL299187D priority Critical patent/NL299187A/xx
Priority to BE638763D priority patent/BE638763A/xx
Application filed by British Hydrocarbon Chemicals Ltd filed Critical British Hydrocarbon Chemicals Ltd
Priority to GB39132/62A priority patent/GB983376A/en
Priority to FR949858A priority patent/FR1376000A/en
Priority to DE19631443491 priority patent/DE1443491A1/en
Publication of GB983376A publication Critical patent/GB983376A/en
Expired legal-status Critical Current

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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/32—Manganese, technetium or rhenium
    • B01J23/34—Manganese
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/755—Nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/107—Alkenes with six carbon atoms
    • 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
    • C07C2/10—Catalytic processes with metal oxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/12—Silica and alumina
    • 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
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/26—Chromium
    • 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
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/32—Manganese, technetium or rhenium
    • C07C2523/34—Manganese
    • 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
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/75—Cobalt
    • 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
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/74—Iron group metals
    • C07C2523/755—Nickel
    • 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
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A detergent alkylate, produced from propylene by two-fold catalytic dimerisation and condensation of the product with an aromatic hydrocarbon, in which a normal hexene fraction is separated from the first dimerisation and used in the second dimerization and a C10-C16 fraction is separated from the second dimerisation and catalytically condensed with an aromatic hydrocarbon (see Division C5), may be sulphonated in known manner. Examples 1 and 2 in conjunction illustrate the condensation of a dimer of normal hexene, prepared and separated as described, with benzene to form a detergent alkylate which is sulphonated in conventional manner and converted to the sodium salt.ALSO:A detergent alkylate is produced from propylene by two-fold catalytic dimerisation, and condensation of the product with an aromatic hydrocarbon; from the first dimerization a normal hexene fraction is separated and used in the second dimerization, and from this step a fraction in the C10 to C16 carbon number range, extending over a range of not more than 5 carbon numbers, is separated and catalytically condensed with an aromatic hydrocarbon. The feed may be pure propylene or a C3 fraction from which acetylenes and propadiene have been removed by selective hydrogenation. Dimerization is effected at 20-150 DEG C. and under sufficient pressure to maintain the reactants in the liquid phase, and preferred catalysts are the oxides of transition metals for example Ni, Co, Cr, particularly Ni, optionally on a carrier such as silica, silica gel or preferably silica-alumina. An inert solvent, e.g. a C5 paraffin may be used. The conversion of propylene is preferably incomplete, e.g. 30-80%. The dimerization product may then be fractionally distilled in three stages, unconverted propylene (and propane if present) being initially removed and recycled, a methyl pentene fraction predominating in 4-methyl-2-pentene then being removed and finally a distillate containing the required normal hexenes being recovered. (Isoprene may be produced from the recovered methyl pentene by double bond isomerization and cracking.) The dimerization of the normal hexenes involves similar temperatures, pressures and degree of conversion to those for dimerization of propylene; as catalyst a transition metal oxide \sB carrier, or alternatively a higher polymerization catalyst or a synthetic petroleum cracking catalyst e.g. silica-alumina may be used; however, manganese oxide is preferred. In one embodiment the feed hexenes include added straight chain C5 to C8 mono-olefines from an external source. The second dimerization product may be fractionally distilled in two stages, unchanged normal hexenes being first removed and recycled, and a fraction containing C10 to C16 molecules being recovered in the second stage. In a preferred embodiment only normal hexene dimers (C12) are recovered. The recovered fraction is condensed at - 20 DEG to + 100 DEG C. in the liquid phase with benzene, toluene, naphthalene or a xylene in the presence of an alkylation catalyst such as aluminium chloride or anhydrous hydrogen flouride. Benzene and hydrogen fluoride are the preferred materials. A distillate detergent alkylate fraction is recovered by fractionation, after separation of the catalyst. The product may be sulphonated in known manner (see Division C2).
GB39132/62A 1962-10-16 1962-10-16 Process for the production of detergent alkylate Expired GB983376A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL299187D NL299187A (en) 1962-10-16
BE638763D BE638763A (en) 1962-10-16
GB39132/62A GB983376A (en) 1962-10-16 1962-10-16 Process for the production of detergent alkylate
FR949858A FR1376000A (en) 1962-10-16 1963-10-08 Improved process for preparing an alkylate for detergents
DE19631443491 DE1443491A1 (en) 1962-10-16 1963-10-09 Process for the preparation of detergent alkylates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39132/62A GB983376A (en) 1962-10-16 1962-10-16 Process for the production of detergent alkylate

Publications (1)

Publication Number Publication Date
GB983376A true GB983376A (en) 1965-02-17

Family

ID=10407813

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39132/62A Expired GB983376A (en) 1962-10-16 1962-10-16 Process for the production of detergent alkylate

Country Status (4)

Country Link
BE (1) BE638763A (en)
DE (1) DE1443491A1 (en)
GB (1) GB983376A (en)
NL (1) NL299187A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988007030A2 (en) * 1987-03-11 1988-09-22 Chevron Research Company Detergent grade olefins, alkylbenzenes and alkylbenzene sulfonates and processes for preparing
WO2011000697A1 (en) * 2009-07-01 2011-01-06 Evonik Oxeno Gmbh Regenerating oligomerisation catalysts

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2815959B1 (en) 2000-10-27 2002-12-13 Inst Francais Du Petrole LINKAGE OF PROCESSES FOR OLEFIN OLIGOMERIZATION

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988007030A2 (en) * 1987-03-11 1988-09-22 Chevron Research Company Detergent grade olefins, alkylbenzenes and alkylbenzene sulfonates and processes for preparing
WO1988007030A3 (en) * 1987-03-11 1988-10-06 Chevron Res Detergent grade olefins, alkylbenzenes and alkylbenzene sulfonates and processes for preparing
WO2011000697A1 (en) * 2009-07-01 2011-01-06 Evonik Oxeno Gmbh Regenerating oligomerisation catalysts

Also Published As

Publication number Publication date
NL299187A (en) 1900-01-01
DE1443491A1 (en) 1968-10-24
BE638763A (en) 1900-01-01

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