DE1240071B - Verfahren zur Herstellung von hoehermolekularen Alkensulfonsaeuren und Alkyl-gamma-sultonen sowie Gemischen derselben - Google Patents
Verfahren zur Herstellung von hoehermolekularen Alkensulfonsaeuren und Alkyl-gamma-sultonen sowie Gemischen derselbenInfo
- Publication number
- DE1240071B DE1240071B DEC33446A DEC0033446A DE1240071B DE 1240071 B DE1240071 B DE 1240071B DE C33446 A DEC33446 A DE C33446A DE C0033446 A DEC0033446 A DE C0033446A DE 1240071 B DE1240071 B DE 1240071B
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- higher molecular
- olefin
- alkyl
- sultones
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 13
- -1 alkene sulfonic acids Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 47
- 150000001336 alkenes Chemical class 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 22
- 239000011261 inert gas Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000005673 monoalkenes Chemical class 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 238000006277 sulfonation reaction Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000008053 sultones Chemical class 0.000 description 6
- 239000003570 air Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241001647090 Ponca Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HGBGABMSTHQFNJ-UHFFFAOYSA-N 1,4-dioxane;sulfur trioxide Chemical compound O=S(=O)=O.C1COCCO1 HGBGABMSTHQFNJ-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- OGALZCPQPHRSPZ-UHFFFAOYSA-N 8-chloropentadecane Chemical compound ClC(CCCCCCC)CCCCCCC OGALZCPQPHRSPZ-UHFFFAOYSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/06—Phosphates, including polyphosphates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US296458A US3409637A (en) | 1963-07-22 | 1963-07-22 | Sulfonating olefins with gaseous sulfur trioxide and compositions obtained thereby |
| US69809368A | 1968-01-04 | 1968-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1240071B true DE1240071B (de) | 1967-05-11 |
Family
ID=26969663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC33446A Pending DE1240071B (de) | 1963-07-22 | 1964-07-20 | Verfahren zur Herstellung von hoehermolekularen Alkensulfonsaeuren und Alkyl-gamma-sultonen sowie Gemischen derselben |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3409637A (en, 2012) |
| BE (1) | BE672383A (en, 2012) |
| CH (1) | CH447142A (en, 2012) |
| DE (1) | DE1240071B (en, 2012) |
| GB (1) | GB1030648A (en, 2012) |
| NL (1) | NL6407958A (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6517234A (en, 2012) * | 1965-01-04 | 1966-07-05 | ||
| US3531518A (en) * | 1966-07-14 | 1970-09-29 | Procter & Gamble | Process for the reaction of alpha-olefins and gaseous sulfur trioxide |
| US3544475A (en) * | 1967-09-29 | 1970-12-01 | Lion Fat Oil Co Ltd | Detergent compositions based on mixtures of alpha-olefin sulfonates and dimer olefin sulfonates |
| US3496226A (en) * | 1967-12-01 | 1970-02-17 | Hoechst Ag | Process for the purification of olefin-sulfonates |
| US3637512A (en) * | 1968-07-22 | 1972-01-25 | Continental Oil Co | Hydrocarbon solvent composition |
| US3676372A (en) * | 1968-10-24 | 1972-07-11 | Chevron Res | Hydrogenated olefin sulfonate-fatty acid amide detergent compositions |
| US3883583A (en) * | 1969-07-01 | 1975-05-13 | Lion Fat Oil Co Ltd | Oil soluble anionic surface active agent |
| US3953338A (en) * | 1969-09-15 | 1976-04-27 | Chevron Research Company | Foam well cleanout using oligomeric sulfonic acids |
| US3927028A (en) * | 1969-11-05 | 1975-12-16 | Chevron Res | Sultone extraction process |
| US3980669A (en) * | 1972-02-09 | 1976-09-14 | Colgate-Palmolive Company | Continuous process for manufacturing gamma sultones |
| US3951823A (en) * | 1972-07-28 | 1976-04-20 | Chevron Research Company | Foam well cleanout using oligomeric sulfonates |
| FR2197861B1 (en, 2012) * | 1972-08-29 | 1978-08-11 | Huels Chemische Werke Ag | |
| US3891672A (en) * | 1972-09-26 | 1975-06-24 | Procter & Gamble | Process for preparing r-sultones |
| GB1445606A (en) * | 1973-10-23 | 1976-08-11 | Unilever Ltd | Fabric-softening compositions |
| US4003857A (en) * | 1973-12-17 | 1977-01-18 | Ethyl Corporation | Concentrated aqueous olefins sulfonates containing carboxylic acid salt anti-gelling agents |
| US4173579A (en) * | 1974-02-26 | 1979-11-06 | Ethyl Corporation | Conversion of sulfonated olefins to sulfonic acid salts |
| US4052431A (en) * | 1976-03-03 | 1977-10-04 | Stepan Chemical Company | Process for the production of commercial alpha olefin sulfonates |
| US4247738A (en) * | 1978-07-12 | 1981-01-27 | Marcellino Bonato | Flush-mounting electrical box assembly having switch and socket holder frame for electrical building installations |
| US4248793A (en) * | 1979-09-26 | 1981-02-03 | The Lion Fat & Oil Co., Ltd. | Process for the production of internal olefin sulfonate |
| GB8900023D0 (en) * | 1989-01-03 | 1989-03-01 | Shell Int Research | Detergent composition |
| DE10039995A1 (de) * | 2000-08-11 | 2002-02-21 | Basf Ag | Verfahren zur Herstellung von Alkylarylsulfonaten |
| US9550955B2 (en) | 2012-12-21 | 2017-01-24 | Afton Chemical Corporation | Friction modifiers for lubricating oils |
| US9499762B2 (en) | 2012-12-21 | 2016-11-22 | Afton Chemical Corporation | Additive compositions with a friction modifier and a detergent |
| US8927471B1 (en) | 2013-07-18 | 2015-01-06 | Afton Chemical Corporation | Friction modifiers for engine oils |
| US9193932B2 (en) | 2013-07-18 | 2015-11-24 | Afton Chemical Corporation | Amide alcohol friction modifiers for lubricating oils |
| US9296971B2 (en) | 2013-07-18 | 2016-03-29 | Afton Chemical Corporation | Friction modifiers for lubricating oils |
| US11123277B2 (en) | 2017-12-27 | 2021-09-21 | Kao Corporation | Oral composition |
| WO2019130871A1 (ja) * | 2017-12-27 | 2019-07-04 | 花王株式会社 | 口腔用組成物 |
| US11661543B2 (en) | 2021-02-04 | 2023-05-30 | Baker Hughes Oilfield Operations Llc | Injection well cleaning fluids and related methods |
| CN114560794A (zh) * | 2022-03-17 | 2022-05-31 | 宁夏大学 | 一种α-烯烃磺酸盐的连续生产方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2265993A (en) * | 1938-07-28 | 1941-12-16 | Solvay Process Co | Derivatives of olefinic compounds and method of making |
| US2600415A (en) * | 1946-12-26 | 1952-06-17 | Standard Oil Dev Co | Water-soluble surface active agents from olefin polymers |
| US2793229A (en) * | 1953-07-03 | 1957-05-21 | Bohme Fettchemie Gmbh | Process for the production of oxyalkane sulfonic acids and their salts |
| US2990375A (en) * | 1957-07-22 | 1961-06-27 | Dow Chemical Co | Heavy duty liquid detergent compositions |
| US2979466A (en) * | 1958-07-28 | 1961-04-11 | Silberman Waclav | Liquid washing composition |
| DE1107220B (de) * | 1960-02-20 | 1961-05-25 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Sultonen |
| US3115501A (en) * | 1961-05-05 | 1963-12-24 | Shell Oil Co | Sultone manufacture |
| BE625814A (en, 2012) * | 1961-12-09 | |||
| NL286384A (en, 2012) * | 1962-08-09 |
-
0
- BE BE672383D patent/BE672383A/xx unknown
-
1963
- 1963-07-22 US US296458A patent/US3409637A/en not_active Expired - Lifetime
-
1964
- 1964-07-13 NL NL6407958A patent/NL6407958A/xx unknown
- 1964-07-13 GB GB28770/64A patent/GB1030648A/en not_active Expired
- 1964-07-20 DE DEC33446A patent/DE1240071B/de active Pending
- 1964-07-20 CH CH947564A patent/CH447142A/fr unknown
-
1968
- 1968-01-04 US US698093A patent/US3444087A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6407958A (en, 2012) | 1965-01-25 |
| GB1030648A (en) | 1966-05-25 |
| CH447142A (fr) | 1967-11-30 |
| US3444087A (en) | 1969-05-13 |
| BE672383A (en, 2012) | |
| US3409637A (en) | 1968-11-05 |
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