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 PDFInfo
- 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
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- stream
- paraffin
- alkanes
- adsorbent
- 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 - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 112
- 238000000926 separation method Methods 0.000 title claims description 37
- 230000000274 adsorptive effect Effects 0.000 title claims description 18
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 88
- 239000003463 adsorbent Substances 0.000 claims abstract description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 79
- 230000029936 alkylation Effects 0.000 claims abstract description 78
- 239000012188 paraffin wax Substances 0.000 claims abstract description 74
- -1 phenyl compound Chemical class 0.000 claims abstract description 52
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 50
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 50
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 238000001179 sorption measurement Methods 0.000 claims abstract description 32
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001721 carbon Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 150000005674 acyclic monoalkenes Chemical class 0.000 claims abstract description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 4
- 230000001737 promoting effect Effects 0.000 claims abstract description 3
- 150000005673 monoalkenes Chemical class 0.000 claims description 84
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 69
- 150000001336 alkenes Chemical class 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 14
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- 238000012546 transfer Methods 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
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- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910001683 gmelinite Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- YYLACZAXCCJCJO-UHFFFAOYSA-N heptacos-1-ene Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCC=C YYLACZAXCCJCJO-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- GTYIGAUPHJCMLF-UHFFFAOYSA-N octan-2-ylbenzene Chemical compound CCCCCCC(C)C1=CC=CC=C1 GTYIGAUPHJCMLF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BDWBGSCECOPTTH-UHFFFAOYSA-N pentacos-1-ene Chemical class CCCCCCCCCCCCCCCCCCCCCCCC=C BDWBGSCECOPTTH-UHFFFAOYSA-N 0.000 description 1
- GNTXATNEGVVGQJ-UHFFFAOYSA-N pentadecan-2-ylbenzene Chemical compound CCCCCCCCCCCCCC(C)C1=CC=CC=C1 GNTXATNEGVVGQJ-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
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- 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
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- 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—Overbased sulfonic acid salts
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (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.¿?
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 |
Family
ID=28673382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| 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 |
| BRPI0621924A2 (pt) * | 2006-07-24 | 2011-12-20 | Uop Llc | processo para remoção de compostos oxigenados de uma corrente |
| 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)
| 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 |
| CA2298618C (fr) * | 1997-08-08 | 2007-04-03 | The Procter & Gamble Company | Procedes ameliores de fabrication de tensio-actifs selon une technique de separation par adsorption et produits ainsi obtenus |
-
2002
- 2002-03-25 CA CA002479641A patent/CA2479641C/fr not_active Expired - Fee Related
- 2002-03-25 CN CNB028288262A patent/CN100358847C/zh not_active Expired - Fee Related
- 2002-03-25 AU AU2002247420A patent/AU2002247420A1/en not_active Abandoned
- 2002-03-25 KR KR1020047015237A patent/KR100963324B1/ko not_active Expired - Fee Related
- 2002-03-25 MX MXPA04009353A patent/MXPA04009353A/es active IP Right Grant
- 2002-03-25 BR BR0215652-0A patent/BR0215652A/pt not_active Application Discontinuation
- 2002-03-25 WO PCT/US2002/009310 patent/WO2003082783A1/fr not_active Ceased
- 2002-03-25 EP EP02715206A patent/EP1487767A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN1625537A (zh) | 2005-06-08 |
| CN100358847C (zh) | 2008-01-02 |
| BR0215652A (pt) | 2005-01-04 |
| AU2002247420A1 (en) | 2003-10-13 |
| CA2479641A1 (fr) | 2003-10-09 |
| MXPA04009353A (es) | 2005-01-25 |
| KR100963324B1 (ko) | 2010-06-11 |
| EP1487767A1 (fr) | 2004-12-22 |
| KR20040095324A (ko) | 2004-11-12 |
| WO2003082783A1 (fr) | 2003-10-09 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180326 |