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WO1995011208A1 - Procede de separation d'hydrocarbures - Google Patents

Procede de separation d'hydrocarbures Download PDF

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Publication number
WO1995011208A1
WO1995011208A1 PCT/GB1994/002303 GB9402303W WO9511208A1 WO 1995011208 A1 WO1995011208 A1 WO 1995011208A1 GB 9402303 W GB9402303 W GB 9402303W WO 9511208 A1 WO9511208 A1 WO 9511208A1
Authority
WO
WIPO (PCT)
Prior art keywords
calixarene
hydrocarbon
adsorbed
mixture
aromatic hydrocarbon
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.)
Ceased
Application number
PCT/GB1994/002303
Other languages
English (en)
Inventor
Stephen Robert Tennison
Richard Henry Weatherhead
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.)
BP PLC
Original Assignee
BP PLC
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
Application filed by BP PLC filed Critical BP PLC
Publication of WO1995011208A1 publication Critical patent/WO1995011208A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes

Definitions

  • the present invention relates to a method for separating hydrocarbons and in particular to a method for the selective separation of benzene from other hydrocarbons through the use of a calixarene .
  • a method for the selective separation of benzene from other hydrocarbons may be achieved through a variety of techniques such as extractive or fractional distillation, solvent extraction or crystallisation.
  • Adsorption techniques in the liquid phase have also been used to separate aromatics from other hydrocarbons. Such techniques employ molecular sieve type materials as the adsorbent.
  • calixarenes A different class of compounds also exhibiting complexation properties are calixarenes . These compounds are examples of a class of synthetic macrocyclic phenolic oligomers and are discussed in reviews entitled “Monographs in Supra Molecular Chemistry” by CD Gutsche, edited by J F Stoddart and published by the Royal Society of Chemistry 1989 and "Calixarenes, a Versatile Class of Macrocyclic Compounds” by J Vicens and V B ⁇ hmer, published by Kluwer, Dordrecht, 1991.
  • Calixarenes have an advantage over the aforementioned cyclodextrins and crown ethers in that they are relatively simple to prepare.
  • Calixarenes are known to complex with guest molecules, for example p-(diallylaminomethyl) calixarenes and p- (carboxyethyl) calixarenes, ranging in size from calixf5]arenes to calix[8]arenes and are able to complex in the liquid phase with various aromatic molecules ranging from durene to perylene.
  • azocalixarenes may be used to separate hydrocarbons, and in particular, to remove aromatics from a hydrocarbon mixture.
  • a method for separating aromatic hydrocarbons and/or alkenes from a mixture of gaseous hydrocarbons comprises the steps of:
  • n 4, 6 or 8
  • R is a conjugated double bond system
  • R**- is OH, ester or ether whereby the aromatic hydrocarbon and/or alkene is adsorbed by the calixarene;
  • the method of the present invention is particularly suitable for the removal of benzene from a mixture of gaseous hydrocarbons, benzene and toluene from a gaseous hydrocarbon mixture; benzene, toluene and hex-1-ene from a gaseous hydrocarbon mixture; and ethylene from a gaseous hydrocarbon mixture, especially containing ethane.
  • the hydrocarbon mixture may be obtained from any suitable source and may comprise aromatics, alkanes , alkenes and cycloalkanes .
  • R is a conjugated double bond system and is suitably planar with respect to the ring system.
  • R may suitably be selected from general formulas II, III or IV.
  • X may be H, OMe, or a halide, especially chloride
  • Y is CH or N
  • Z is H, OMe or a halide, especially chloride.
  • the method of the present application is particularly suitable for the selective adsorption of benzene using the calixarene of formula (V)
  • the selective removal of aromatic hydrocarbons is suitably carried out by contacting the hydrocarbon mixture with the calixarene of general formula I under suitable pressure and temperature.
  • the adsorption is carried out at a temperature of from 20 to 100°C, preferably 30 to 50°C and a pressure of from 0 mbar up to the saturation vapour pressure of the hydrocarbon.
  • the adsorbed aromatic hydrocarbon may be suitably desorbed at the same temperature and by reducing the pressure to Ombar or by sweeping with an inert gas.
  • the hydrocarbon mixture may then be retrieved by condensation.
  • the calixarenes may be prepared by methods known to the person skilled in the art and as described in the aforementioned reviews. Typically, azocalixarenes may be prepared by diazocoupling of the respective calixarene in the presence of aniline.
  • Example 1 Preparation of Calixarenes
  • R is according to general formula II and X is H, and Cl and SO ⁇ Na and R * -- is OH and n is 4 respectively were prepared as follows: (a) X is H
  • the adsorption process was examined using a Robal microforce balance and a MKS Barton pressure sensor.
  • the balance was calibrated and the system evacuated using a high vacuum pump.
  • the evacuated system was subjected to increasing pressure of the hydrocarbon vapour; and the weight increase of the calixarene sample recorded at intervals once equilibrium had been reached. The procedure was continued until the saturation vapour pressure of the hydrocarbon was reached.
  • the adsorption of each hydrocarbon was studied as a plot of weight of the sample vs pressure (P/pr j where P0 is saturation vapour pressure of the relevant guest vapour) .
  • the desorption of the vapour was also followed by reducing the pressure to Ombar and monitoring the weight decrease as a function of time until the sample had returned to its original weight.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé servant à séparer des hydrocarbures aromatiques et/ou des alkènes d'un mélange d'hydrocarbures gazeux. Le procédé comprend les étapes suivantes: (a) mise en contact du mélange d'hydrocarbures gazeux avec un calixarène représenté par la formule générale (I), où n est 4, 6 ou 8, R représente un système conjugué à double liaison, R1 représente OH, ester ou éther, ce qui permet au calixarène d'adsorber l'hydrocarbure aromatique et/ou l'alkène; (b) séparation du calixarène et de l'hydrocarbure aromatique et/ou alkène adsorbé du mélange d'hydrocarbures; (c) désorption de l'hydrocarbure aromatique et/ou alkène adsorbé.
PCT/GB1994/002303 1993-10-21 1994-10-20 Procede de separation d'hydrocarbures Ceased WO1995011208A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9321707.3 1993-10-21
GB939321707A GB9321707D0 (en) 1993-10-21 1993-10-21 Method for separating hydrocarbons

Publications (1)

Publication Number Publication Date
WO1995011208A1 true WO1995011208A1 (fr) 1995-04-27

Family

ID=10743898

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1994/002303 Ceased WO1995011208A1 (fr) 1993-10-21 1994-10-20 Procede de separation d'hydrocarbures

Country Status (2)

Country Link
GB (1) GB9321707D0 (fr)
WO (1) WO1995011208A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2292156A (en) * 1994-08-12 1996-02-14 British Petroleum Co Plc Method for separation of hydrocarbons
WO1997031698A1 (fr) * 1996-02-28 1997-09-04 Transdiffusia S.A. Procede de recuperation de composes volatils de faible masse moleculaire

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989008092A1 (fr) * 1988-02-29 1989-09-08 The Flinders University Of South Australia Separation de composes organiques contenus dans des fluides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989008092A1 (fr) * 1988-02-29 1989-09-08 The Flinders University Of South Australia Separation de composes organiques contenus dans des fluides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2292156A (en) * 1994-08-12 1996-02-14 British Petroleum Co Plc Method for separation of hydrocarbons
WO1997031698A1 (fr) * 1996-02-28 1997-09-04 Transdiffusia S.A. Procede de recuperation de composes volatils de faible masse moleculaire
US6136071A (en) * 1996-02-28 2000-10-24 Transdiffusia S.A. Process for the recovery of volatile low molecular compounds

Also Published As

Publication number Publication date
GB9321707D0 (en) 1993-12-15

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