ZA200505050B - Methods for producing alkylaryl sulfonates by using modified dimerized olefins - Google Patents
Methods for producing alkylaryl sulfonates by using modified dimerized olefins Download PDFInfo
- Publication number
- ZA200505050B ZA200505050B ZA200505050A ZA200505050A ZA200505050B ZA 200505050 B ZA200505050 B ZA 200505050B ZA 200505050 A ZA200505050 A ZA 200505050A ZA 200505050 A ZA200505050 A ZA 200505050A ZA 200505050 B ZA200505050 B ZA 200505050B
- Authority
- ZA
- South Africa
- Prior art keywords
- stage
- alkylarylsulfonates
- olefins
- catalyst
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 67
- 150000001336 alkenes Chemical class 0.000 title claims description 52
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 title claims description 45
- 239000003054 catalyst Substances 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 63
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 59
- 238000005649 metathesis reaction Methods 0.000 claims description 56
- 230000008569 process Effects 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 40
- 238000006471 dimerization reaction Methods 0.000 claims description 31
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 claims description 30
- -1 alkyl aromatic compounds Chemical class 0.000 claims description 27
- 238000009835 boiling Methods 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 21
- 230000029936 alkylation Effects 0.000 claims description 19
- 238000005804 alkylation reaction Methods 0.000 claims description 19
- 238000006277 sulfonation reaction Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000007792 addition Methods 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 12
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- 239000000470 constituent Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 7
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- 239000000539 dimer Substances 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 5
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- 239000012535 impurity Substances 0.000 description 5
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- 238000000926 separation method Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
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- 229910052723 transition metal Inorganic materials 0.000 description 4
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- 239000010937 tungsten Substances 0.000 description 4
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- 239000010457 zeolite Substances 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
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- 239000001301 oxygen Substances 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010801 sewage sludge Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10261481A DE10261481A1 (de) | 2002-12-23 | 2002-12-23 | Verfahren zur Herstellung von Alkylarylsulfonaten mittels modifizierter, dimerisierter Olefine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505050B true ZA200505050B (en) | 2006-09-27 |
Family
ID=32404344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505050A ZA200505050B (en) | 2002-12-23 | 2005-06-22 | Methods for producing alkylaryl sulfonates by using modified dimerized olefins |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20060052630A1 (es) |
| EP (1) | EP1581485B1 (es) |
| JP (1) | JP4307389B2 (es) |
| KR (1) | KR20050088137A (es) |
| CN (1) | CN1296352C (es) |
| AR (1) | AR042666A1 (es) |
| AT (1) | ATE357430T1 (es) |
| AU (1) | AU2003300221A1 (es) |
| BR (1) | BR0317634A (es) |
| CA (1) | CA2511184A1 (es) |
| DE (2) | DE10261481A1 (es) |
| ES (1) | ES2283873T3 (es) |
| MX (1) | MXPA05005936A (es) |
| MY (1) | MY135566A (es) |
| RU (1) | RU2005123322A (es) |
| WO (1) | WO2004058692A1 (es) |
| ZA (1) | ZA200505050B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7598414B2 (en) * | 2006-06-01 | 2009-10-06 | Chevron Oronite Company Llc | Method of making a synthetic alkylaryl sulfonate |
| US7713386B2 (en) * | 2007-05-23 | 2010-05-11 | Uop Llc | Apparatus for producing ethylbenzene or cumene |
| US7525003B2 (en) * | 2007-05-23 | 2009-04-28 | Uop Llc | Process for producing ethylbenzene |
| US7498472B2 (en) * | 2007-05-23 | 2009-03-03 | Uop Llc | Process for producing ethylbenzene |
| US7498471B2 (en) * | 2007-05-23 | 2009-03-03 | Uop Llc | Process for producing cumene |
| US7525006B2 (en) * | 2007-05-23 | 2009-04-28 | Uop Llc | Process for producing cumene |
| US7525005B2 (en) * | 2007-05-23 | 2009-04-28 | Uop Llc | Process for producing cumene |
| US7525004B2 (en) * | 2007-05-23 | 2009-04-28 | Uop Llc | Process for producing ethylbenzene |
| EP2459784B1 (en) * | 2009-07-27 | 2013-05-01 | DSM IP Assets B.V. | Polyolefin member and method of manufacturing by using an antifoaming agent |
| CN102703050A (zh) * | 2012-05-28 | 2012-10-03 | 西南石油大学 | 一种四聚磺酸盐型表面活性剂及其制备方法 |
| CN114008182A (zh) * | 2019-06-20 | 2022-02-01 | 埃克森美孚化学专利公司 | 来自乙烯叉基烯烃的两亲性反应产物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10039995A1 (de) * | 2000-08-11 | 2002-02-21 | Basf Ag | Verfahren zur Herstellung von Alkylarylsulfonaten |
-
2002
- 2002-12-23 DE DE10261481A patent/DE10261481A1/de not_active Withdrawn
-
2003
- 2003-12-22 DE DE50306876T patent/DE50306876D1/de not_active Expired - Fee Related
- 2003-12-22 EP EP03799498A patent/EP1581485B1/de not_active Expired - Lifetime
- 2003-12-22 RU RU2005123322/04A patent/RU2005123322A/ru not_active Application Discontinuation
- 2003-12-22 CA CA002511184A patent/CA2511184A1/en not_active Abandoned
- 2003-12-22 WO PCT/EP2003/014712 patent/WO2004058692A1/de active IP Right Grant
- 2003-12-22 MY MYPI20034950A patent/MY135566A/en unknown
- 2003-12-22 CN CNB2003801073601A patent/CN1296352C/zh not_active Expired - Fee Related
- 2003-12-22 BR BR0317634-7A patent/BR0317634A/pt not_active IP Right Cessation
- 2003-12-22 US US10/538,473 patent/US20060052630A1/en not_active Abandoned
- 2003-12-22 JP JP2004562814A patent/JP4307389B2/ja not_active Expired - Fee Related
- 2003-12-22 AT AT03799498T patent/ATE357430T1/de not_active IP Right Cessation
- 2003-12-22 MX MXPA05005936A patent/MXPA05005936A/es active IP Right Grant
- 2003-12-22 ES ES03799498T patent/ES2283873T3/es not_active Expired - Lifetime
- 2003-12-22 AU AU2003300221A patent/AU2003300221A1/en not_active Abandoned
- 2003-12-22 KR KR1020057011772A patent/KR20050088137A/ko not_active Application Discontinuation
- 2003-12-23 AR ARP030104817A patent/AR042666A1/es unknown
-
2005
- 2005-06-22 ZA ZA200505050A patent/ZA200505050B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2511184A1 (en) | 2004-07-15 |
| ES2283873T3 (es) | 2007-11-01 |
| AR042666A1 (es) | 2005-06-29 |
| CN1732150A (zh) | 2006-02-08 |
| EP1581485B1 (de) | 2007-03-21 |
| JP4307389B2 (ja) | 2009-08-05 |
| KR20050088137A (ko) | 2005-09-01 |
| EP1581485A1 (de) | 2005-10-05 |
| AU2003300221A1 (en) | 2004-07-22 |
| MXPA05005936A (es) | 2005-08-18 |
| MY135566A (en) | 2008-05-30 |
| CN1296352C (zh) | 2007-01-24 |
| DE10261481A1 (de) | 2004-07-01 |
| US20060052630A1 (en) | 2006-03-09 |
| ATE357430T1 (de) | 2007-04-15 |
| RU2005123322A (ru) | 2006-01-27 |
| JP2006511578A (ja) | 2006-04-06 |
| WO2004058692A1 (de) | 2004-07-15 |
| DE50306876D1 (de) | 2007-05-03 |
| BR0317634A (pt) | 2005-11-29 |
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