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 (enExample) | 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 (enExample) |
| JP (1) | JPS6059903B2 (enExample) |
| DE (1) | DE2833551A1 (enExample) |
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. |
| US9187688B2 (en) | 2009-07-09 | 2015-11-17 | Shell Oil Company | Method and composition for enhanced hydrocarbon recovery from a formation containing a crude oil with specific solubility groups and chemical families |
| WO2011028930A2 (en) * | 2009-09-02 | 2011-03-10 | Board Of Regents, The University Of Texas System | Di-functional surfactants for enhanced oil recovery |
| CA2789046A1 (en) | 2010-02-12 | 2011-08-18 | Shell Internationale Research Maatschappij B.V. | Method and composition for enhanced oil recovery |
| US9441148B2 (en) | 2011-04-20 | 2016-09-13 | Shell Oil Company | Method and composition for enhanced hydrocarbon recovery |
| BR112013028322A2 (pt) | 2011-05-27 | 2017-01-10 | Shell Int Research | composição de recuperação de hidrocarboneto, artigo conformado, e, processo para tratar uma formação contendo hidrocarboneto e para preparar uma composição de recuperação de hidrocarboneto |
| WO2013030140A1 (en) | 2011-08-31 | 2013-03-07 | Shell Internationale Research Maatschappij B.V. | 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 |
| WO2014137974A1 (en) * | 2013-03-06 | 2014-09-12 | Shell Oil Company | Internal olefin sulfonate composition |
| JP6243790B2 (ja) * | 2013-04-23 | 2017-12-06 | 花王株式会社 | オレフィンの製造方法 |
| ES2884826T3 (es) * | 2013-12-27 | 2021-12-13 | Kao Corp | Método para producir sulfonato de olefina interna |
| CA2949442A1 (en) | 2014-05-23 | 2015-11-26 | Shell Internationale 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 |
| BR112017023522B1 (pt) | 2015-05-07 | 2021-06-08 | Rhodia Operations | processo para a cetonização descarboxilativa de ácidos graxos, ésteres de ácido graxo produzidos pela condensação de ácidos graxos com metanol, etanol, propanol ou butanol, ou misturas dos mesmos na fase líquida com compostos de metal como catalisadores |
| KR102657749B1 (ko) | 2015-10-19 | 2024-04-17 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | 스타이렌의 제조 방법 |
| WO2017176454A1 (en) | 2016-04-03 | 2017-10-12 | Stepan Company | Enhanced oil recovery methods |
| 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 |
| CN109923097A (zh) | 2016-11-08 | 2019-06-21 | 罗地亚经营管理公司 | 用于从产自脂肪酸或脂肪酸衍生物的脱羧基酮化的内酮制造最终化合物的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA672362B (enExample) * | 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 |
|---|---|
| JPS5436215A (en) | 1979-03-16 |
| DE2833551A1 (de) | 1979-03-29 |
| JPS6059903B2 (ja) | 1985-12-27 |
| US4183867A (en) | 1980-01-15 |
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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 |