DE2833551C2 - - Google Patents
Info
- Publication number
- DE2833551C2 DE2833551C2 DE2833551A DE2833551A DE2833551C2 DE 2833551 C2 DE2833551 C2 DE 2833551C2 DE 2833551 A DE2833551 A DE 2833551A DE 2833551 A DE2833551 A DE 2833551A DE 2833551 C2 DE2833551 C2 DE 2833551C2
- Authority
- DE
- Germany
- Prior art keywords
- sulfonation
- olefin
- double bond
- olefins
- weight
- 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
Links
- 238000006277 sulfonation reaction Methods 0.000 claims description 49
- 150000001336 alkenes Chemical class 0.000 claims description 33
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 3
- 239000003518 caustics Substances 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- 150000003871 sulfonates Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
- 239000000047 product Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52101905A JPS6059903B2 (ja) | 1977-08-25 | 1977-08-25 | 内部オレフインスルホン酸塩の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2833551A1 DE2833551A1 (de) | 1979-03-29 |
| DE2833551C2 true DE2833551C2 (https=) | 1988-12-15 |
Family
ID=14312914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782833551 Granted DE2833551A1 (de) | 1977-08-25 | 1978-07-31 | Verfahren zur herstellung von sulfonaten von olefinen mit innenliegender doppelbindung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4183867A (https=) |
| JP (1) | JPS6059903B2 (https=) |
| DE (1) | DE2833551A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3412844A1 (de) * | 1984-04-05 | 1985-10-17 | Hoechst Ag, 6230 Frankfurt | Verfahren zur abtrennung der restlichen schwefelsaeure aus dem bei der sulfoxidation von paraffinen anfallenden reaktionsgemisch |
| JPH01101853A (ja) * | 1987-10-15 | 1989-04-19 | Takara Seni Kk | 麺の製造方法 |
| GB8817293D0 (en) * | 1988-07-20 | 1988-08-24 | Shell Int Research | Process for preparation of internal olefin sulphonates |
| US5488148A (en) * | 1993-09-01 | 1996-01-30 | Vista Chemical Company | Process for sulfonating internal olefins |
| US5514535A (en) * | 1995-05-10 | 1996-05-07 | Eastman Kodak Company | Stabilized vinyl sulfone hardening compositions useful in photographic manufacturing |
| EA023150B1 (ru) | 2009-04-16 | 2016-04-29 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ и композиция для добычи углеводородов с искусственным поддержанием энергии пласта с очень высокой соленостью и высокой температурой |
| AP2011006003A0 (en) * | 2009-05-05 | 2011-12-31 | Stepan Co | Sulfonated internal olefin surfactant for enhancedoil recovery. |
| WO2011005746A1 (en) | 2009-07-09 | 2011-01-13 | Shell Oil Company | Method and composition for enhanced hydrocarbon recovery from a formation containing a crude oil with specific solubility groups and chemical families |
| AR080606A1 (es) * | 2009-09-02 | 2012-04-25 | Univ Texas | Surfactantes di- funcionales para recuperacion mejorada de petroleo |
| CN102762687A (zh) | 2010-02-12 | 2012-10-31 | 国际壳牌研究有限公司 | 强化油采收的方法和组合物 |
| BR112013023954A2 (pt) | 2011-04-20 | 2016-12-13 | Shell Int Research | método para tratar uma formação contendo hidrocarboneto, e, composição |
| CN103562341A (zh) | 2011-05-27 | 2014-02-05 | 国际壳牌研究有限公司 | 强化烃采收的组合物和方法 |
| CA2845662A1 (en) | 2011-08-31 | 2013-03-07 | Julian Richard Barnes | Composition and method for enhanced hydrocarbon recovery |
| CN104053644A (zh) | 2011-12-23 | 2014-09-17 | 国际壳牌研究有限公司 | 用于制备内烯烃磺酸盐的方法 |
| EA201491657A1 (ru) | 2012-03-08 | 2014-12-30 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения внутреннего олефинсульфоната |
| AR090958A1 (es) | 2012-05-09 | 2014-12-17 | Shell Int Research | Metodo para la recuperacion mejorada de hidrocarburos |
| WO2013186305A1 (en) | 2012-06-13 | 2013-12-19 | Shell Internationale Research Maatschappij B.V. | Process for preparing an internal olefin sulfonate |
| US20140079660A1 (en) * | 2012-09-20 | 2014-03-20 | Kao Corporation | Cleansing composition for skin or hair |
| CA2903024A1 (en) * | 2013-03-06 | 2014-09-12 | Julian Richard Barnes | Internal olefin sulfonate composition |
| PH12015502396B1 (en) * | 2013-04-23 | 2023-03-17 | Kao Corp | Method for producing olefin |
| JP6393168B2 (ja) * | 2013-12-27 | 2018-09-19 | 花王株式会社 | 内部オレフィンスルホン酸塩の製造方法 |
| EP3146012B1 (en) | 2014-05-23 | 2018-11-28 | Shell International Research Maatschappij B.V. | Method for predicting the optimal salinity of internal olefin sulfonate compositions |
| EP3031878A1 (en) | 2014-12-08 | 2016-06-15 | Shell Internationale Research Maatschappij B.V. | Internal olefin sulfonate composition and use thereof in enhanced oil recovery |
| HK1251929B (en) | 2015-05-07 | 2020-01-10 | Rhodia Operations | Process for the decarboxylative ketonization of fatty acids or fatty acid derivatives |
| RU2716265C2 (ru) | 2015-10-19 | 2020-03-11 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения стирола |
| MX2018012089A (es) | 2016-04-03 | 2019-01-10 | Stepan Co | Metodos mejorados de recuperacion de petroleo. |
| EP3162872A1 (en) | 2016-06-24 | 2017-05-03 | Shell Internationale Research Maatschappij B.V. | Internal olefin sulfonate composition and use thereof in enhanced oil recovery |
| EP4538256A3 (en) | 2016-11-08 | 2025-06-25 | Specialty Operations France | Method for making end compounds from internal ketones issued from the decarboxylative ketonization of fatty acids or fatty acid derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA672362B (https=) * | 1965-08-04 | |||
| DE1568769C3 (de) * | 1966-07-01 | 1975-06-19 | Henkel & Cie Gmbh, 4000 Duesseldorf | Verfahren zur Herstellung oberflächenaktiver Sulfonate |
-
1977
- 1977-08-25 JP JP52101905A patent/JPS6059903B2/ja not_active Expired
-
1978
- 1978-07-31 DE DE19782833551 patent/DE2833551A1/de active Granted
- 1978-08-02 US US05/930,424 patent/US4183867A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4183867A (en) | 1980-01-15 |
| DE2833551A1 (de) | 1979-03-29 |
| JPS5436215A (en) | 1979-03-16 |
| JPS6059903B2 (ja) | 1985-12-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2833551C2 (https=) | ||
| DE1151795B (de) | Verfahren zur Herstellung von Alkylglycerylaethersulfonaten mit geringem Salzgehalt | |
| DE3123681A1 (de) | Verfahren zur herstellung einer hochkonzentrierten waessrigen loesung eines salzes eines (alpha)-sulfofettsaeureesters | |
| DE2647980C2 (https=) | ||
| DE2732291A1 (de) | Verfahren zur herstellung von 1-amino-8-naphthol-3,6-disulfonsaeure (h-saeure) | |
| DE2538723C2 (de) | Verfahren zur Herstellung von 1-Aminobenzol-4- und -5-β-sulfatoäthylsulfon-2-sulfonsäure und der entsprechenden Hydroxyäthylsulfon-und Vinylsulfonverbindungen | |
| DE69823064T2 (de) | Verfahren zur herstellung von schwach gefärbten bis transparenten alkylglykosiden | |
| EP0163318B1 (de) | Neue 2-substituierte 3-Sulfopropyl-ammoniumbetaine und Verfahren zu ihrer Herstellung | |
| DE594083C (de) | Verfahren zur Herstellung von Methylvinylketon | |
| EP0131913B1 (de) | Verfahren zur schonenden Isolierung von Paraffinsulfonsäuren oder Paraffinsulfonaten aus den bei der Sulfoxidation von Paraffinen erhaltenen Reaktionsgemischen | |
| EP0001084B1 (de) | Verfahren zur Herstellung von 1-Amino-4-bromanthrachinon-2-sulfonsäure | |
| DE2153725C3 (de) | Verfahren zur Herstellung von Dicalciumphosphat | |
| DE2442418A1 (de) | Verfahren zur herstellung von natriumdithionit | |
| EP0083555A1 (de) | Verfahren zur Herstellung von p-Nitrotoluol-2-sulfonsäure | |
| DE2716030A1 (de) | Verfahren zur herstellung von 1-amino-8-naphthol-3,6-disulfonsaeure (h-saeure) | |
| DE2062054A1 (https=) | ||
| DE872789C (de) | Verfahren zur Herstellung von 1, 8-Diamino-p-menthan | |
| DE2408391A1 (de) | Verfahren zur herstellung von alkalioder erdalkalimetallsalzen von alkansulfonsaeuren | |
| DE2224938C3 (de) | Verfahren zur Herstellung von Polyvinylbromid | |
| DE2844610A1 (de) | Verfahren zur herstellung von 4-nitro-4'-amino-diphenylamin-2-sulfonsaeure und 2-nitro-4'-amino-diphenylamin-4-sulfonsaeure | |
| DE2812348C2 (https=) | ||
| DE1593878C (de) | Verfahren zur Herstellung von Chlorthiophenolen | |
| DE2510086C3 (de) | Verfahren zur Razemisierung von D-Weinsäure | |
| EP0168659B1 (de) | Verfahren zur Herstellung von Chlorisocyanursäuren | |
| DE3118903A1 (de) | Verfahren zur herstellung von 1-benzoylamino-8-hydroxy-naphthalin-4.6.-disulfonsaeure (benzoyl-k-saeure) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAR | Request for search filed | ||
| OB | Request for examination as to novelty | ||
| OC | Search report available | ||
| 8127 | New person/name/address of the applicant |
Owner name: LION CORP., TOKYO, JP |
|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8381 | Inventor (new situation) |
Free format text: SEKIGUCHI, SHIZUO, FUNABASHI, CHIBA, JP NAGANO, KATSUMASA, ICHIKAWA, CHIBA, JP KITANO, KYOZO, CHIBA, JP |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |