CA2479641C - Procede de production de phenyl-alcanes selectionnes au moyen d'une operation de separation par adsorption - Google Patents

Procede de production de phenyl-alcanes selectionnes au moyen d'une operation de separation par adsorption Download PDF

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Publication number
CA2479641C
CA2479641C CA002479641A CA2479641A CA2479641C CA 2479641 C CA2479641 C CA 2479641C CA 002479641 A CA002479641 A CA 002479641A CA 2479641 A CA2479641 A CA 2479641A CA 2479641 C CA2479641 C CA 2479641C
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Canada
Prior art keywords
phenyl
stream
paraffin
alkanes
adsorbent
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Expired - Fee Related
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CA002479641A
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CA2479641A1 (fr
Inventor
Santi Kulprathipanja
Richard E. Marinangeli
Stephen W. Sohn
Thomas R. Fritsch
R. Joe Lawson
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Honeywell UOP LLC
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UOP LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
    • 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
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/06—Well-defined hydrocarbons aromatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/10—Chemical after-treatment of the constituents of the lubricating composition by sulfur or a compound containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

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

Abstract

L'invention concerne un procédé de production de phényl-alcanes consistant (a) à faire passer un flux d'alimentation présentant une première concentration en une première paraffine acyclique à gamme de carbone C¿8?-C¿28? et à 2 ou 3 atomes de carbone primaire et comprenant au moins une seconde paraffine acyclique dans une zone d'adsorption comportant un lit d'un adsorbant renfermant une silicalite dans des conditions favorisant l'adsorption, de façon à adsorber sélectivement une partie au moins de la première paraffine acyclique par contact du lit d'adsorbant avec un flux de désorbant comprenant au moins un composant choisi dans le groupe constitué par une cycloparaffine C¿5?-C¿8?, une paraffine normale C¿5?-C¿8? et une paraffine ramifiée C¿5?-C¿8?, et à récupérer, à partir de cette zone d'adsorption, un extrait d'adsorption présentant une seconde concentration en première paraffine acyclique supérieure à la première concentration, (b) à faire passer une partie au moins de l'extrait d'adsorption dans une zone de déshydrogénation, à activer cette zone de déshydrogénation dans des conditions de déshydrogénation permettant de déshydrogéner la première paraffine acyclique et de récupérer, à partir de la zone de déshydrogénation, un flux de produit déshydrogéné comprenant une mono-oléfine acyclique à gamme de carbone C¿8?-C¿28? et à 2 ou 3 atomes de carbone primaire, et (c) à faire passer un produit de départ comprenant un composé phényle et à faire passer une partie au moins du flux de produit déshydrogéné comprenant la mono-oléfine acyclique dans une zone d'alkylation, puis à activer cette zone d'alkylation dans des conditions d'alkylation permettant d'alkyler le composé phényle avec la mono-oléfine acyclique en présence d'un catalyseur d'alkylation, de sorte à former un phényl-alcane comprenant une molécule possédant une partie phényle et une partie alkyle aliphatique C¿8?-C¿28?, la partie alkyle aliphatique renfermant 2 ou 3 atomes de carbone primaire, tous les atomes de carbone quaternaire étant liés par une liaison carbone-carbone à un atome de carbone de la partie phényle. L'alkylation présente une sélectivité pour les 2-phényl-alcanes comprise entre 40 et 100, ainsi qu'une sélectivité pour les phényl-alcanes quaternaires internes inférieure à 10. Ledit procédé consiste enfin à récupérer le phényl-alcane à partir de la zone d'alkylation.¿?
CA002479641A 2002-03-25 2002-03-25 Procede de production de phenyl-alcanes selectionnes au moyen d'une operation de separation par adsorption Expired - Fee Related CA2479641C (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2002/009310 WO2003082783A1 (fr) 2002-03-25 2002-03-25 Procede de production de phenyl-alcanes selectionnes au moyen d'une operation de separation par adsorption

Publications (2)

Publication Number Publication Date
CA2479641A1 CA2479641A1 (fr) 2003-10-09
CA2479641C true CA2479641C (fr) 2009-11-10

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CA002479641A Expired - Fee Related CA2479641C (fr) 2002-03-25 2002-03-25 Procede de production de phenyl-alcanes selectionnes au moyen d'une operation de separation par adsorption

Country Status (8)

Country Link
EP (1) EP1487767A1 (fr)
KR (1) KR100963324B1 (fr)
CN (1) CN100358847C (fr)
AU (1) AU2002247420A1 (fr)
BR (1) BR0215652A (fr)
CA (1) CA2479641C (fr)
MX (1) MXPA04009353A (fr)
WO (1) WO2003082783A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7449596B2 (en) * 2005-12-21 2008-11-11 Chevron Oronite Company Llc Method of making a synthetic petroleum sulfonate
KR101089886B1 (ko) * 2006-07-24 2011-12-05 유오피 엘엘씨 파라핀 스트림으로부터 옥시게네이트를 제거하는 방법
US20110118517A1 (en) * 2009-11-19 2011-05-19 Uop Llc Manufacturing Process for Branched and Linear Alkylated Benzene as Precursor for Enhanced Oil Recovery Surfactant
CN110325494B (zh) * 2016-12-28 2022-08-16 环球油品公司 烷基化工艺中的热减少
RU2712456C1 (ru) * 2019-08-23 2020-01-29 Акционерное общество "Акустический институт имени академика Н.Н. Андреева" Способ непрерывного ультразвукового приготовления низкотемпературного органического теплоносителя на основе фенилалкана и устройство для его осуществления

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4982052A (en) * 1988-12-23 1991-01-01 Texaco Inc. Separation of a mixture of normal paraffins branched chain paraffins and cyclic paraffins
CN100475785C (zh) * 1997-08-08 2009-04-08 宝洁公司 经吸附分离用于制备表面活性剂的改进方法及其产物

Also Published As

Publication number Publication date
EP1487767A1 (fr) 2004-12-22
WO2003082783A1 (fr) 2003-10-09
KR100963324B1 (ko) 2010-06-11
CN1625537A (zh) 2005-06-08
BR0215652A (pt) 2005-01-04
CA2479641A1 (fr) 2003-10-09
MXPA04009353A (es) 2005-01-25
KR20040095324A (ko) 2004-11-12
AU2002247420A1 (en) 2003-10-13
CN100358847C (zh) 2008-01-02

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