DE2249360A1 - Verfahren zur herstellung sulfonierter detergentien - Google Patents
Verfahren zur herstellung sulfonierter detergentienInfo
- Publication number
- DE2249360A1 DE2249360A1 DE2249360A DE2249360A DE2249360A1 DE 2249360 A1 DE2249360 A1 DE 2249360A1 DE 2249360 A DE2249360 A DE 2249360A DE 2249360 A DE2249360 A DE 2249360A DE 2249360 A1 DE2249360 A1 DE 2249360A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- sodium
- product
- sulfonate
- sulfonated
- 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
- 238000000034 method Methods 0.000 title claims description 44
- 239000003599 detergent Substances 0.000 title description 25
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 37
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 150000001336 alkenes Chemical class 0.000 claims description 17
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- 238000006277 sulfonation reaction Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 239000011734 sodium Substances 0.000 description 18
- -1 from palm oil Chemical class 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 6
- SKBDZCLHFLUHJM-UHFFFAOYSA-N 4-hydroxyhexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCC(O)CCCS(O)(=O)=O SKBDZCLHFLUHJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- MVHWMCQWFWUXEE-UHFFFAOYSA-M sodium;hexadec-1-ene-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCC=CS([O-])(=O)=O MVHWMCQWFWUXEE-UHFFFAOYSA-M 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000008139 complexing agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DOPXXTDTIKKJFV-UHFFFAOYSA-M COC(CS(=O)(=O)[O-])CCCCCCCCCCCCCC.[Na+] Chemical compound COC(CS(=O)(=O)[O-])CCCCCCCCCCCCCC.[Na+] DOPXXTDTIKKJFV-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- WKVZMKDXJFCMMD-UVWUDEKDSA-L (5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one;azanide;n,3-bis(2-chloroethyl)-2-ox Chemical compound [NH2-].[NH2-].Cl[Pt+2]Cl.ClCCNP1(=O)OCCCN1CCCl.COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3C(O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 WKVZMKDXJFCMMD-UVWUDEKDSA-L 0.000 description 1
- ZVMPSYSRUJVRMP-UHFFFAOYSA-N 1-hydroxyhexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCC(O)S(O)(=O)=O ZVMPSYSRUJVRMP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100189378 Caenorhabditis elegans pat-3 gene Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 102100026450 POU domain, class 3, transcription factor 4 Human genes 0.000 description 1
- 101710133389 POU domain, class 3, transcription factor 4 Proteins 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- WFAULHLDTDDABL-UHFFFAOYSA-N Proxazole citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(CC)C1=NOC(CCN(CC)CC)=N1 WFAULHLDTDDABL-UHFFFAOYSA-N 0.000 description 1
- RRIVMJUCDFETIA-UHFFFAOYSA-N [Na].C=CCCCCCCCCCCCCCC Chemical compound [Na].C=CCCCCCCCCCCCCCC RRIVMJUCDFETIA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- JIMMILCKVYOFET-UHFFFAOYSA-N hexadecan-4-ol Chemical compound CCCCCCCCCCCCC(O)CCC JIMMILCKVYOFET-UHFFFAOYSA-N 0.000 description 1
- SSILHZFTFWOUJR-UHFFFAOYSA-M hexadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCCS([O-])(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-M 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- MVHWMCQWFWUXEE-GEEYTBSJSA-M sodium;(e)-hexadec-1-ene-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCC\C=C\S([O-])(=O)=O MVHWMCQWFWUXEE-GEEYTBSJSA-M 0.000 description 1
- BLEWGNAHWOZIGS-UHFFFAOYSA-M sodium;2-methoxytridecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCC(OC)CS([O-])(=O)=O BLEWGNAHWOZIGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- 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
- C07C303/32—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
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
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)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18859071A | 1971-10-12 | 1971-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2249360A1 true DE2249360A1 (de) | 1973-04-19 |
Family
ID=22693783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2249360A Pending DE2249360A1 (de) | 1971-10-12 | 1972-10-09 | Verfahren zur herstellung sulfonierter detergentien |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3755429A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS4861426A (cg-RX-API-DMAC10.html) |
| BE (1) | BE789922A (cg-RX-API-DMAC10.html) |
| CA (1) | CA981278A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2249360A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES407538A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2156268B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1367369A (cg-RX-API-DMAC10.html) |
| IT (1) | IT968863B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7213830A (cg-RX-API-DMAC10.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2657620A1 (de) * | 1975-12-26 | 1977-07-14 | Lion Fat Oil Co Ltd | Verfahren zur herstellung hochkonzentrierter olefinsulfonatloesungen |
| EP0293913A1 (de) * | 1987-06-04 | 1988-12-07 | Raschig AG | Verfahren zur Herstellung von gegebenenfalls substituierten Ethansulfonverbindungen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3979340A (en) * | 1973-04-09 | 1976-09-07 | Colgate-Palmolive Company | Olefin sulfonate detergent compositions |
| GB1445606A (en) * | 1973-10-23 | 1976-08-11 | Unilever Ltd | Fabric-softening compositions |
| GB2146323B (en) * | 1983-09-09 | 1987-09-09 | Godrej Soaps Ltd | Production of sodium alpha olefin sulphonate and products containing it |
| WO2009055584A1 (en) * | 2007-10-26 | 2009-04-30 | Chevron Oronite Company Llc | Isomerized alpha olefin sulfonate and method of making the same |
| WO2013186305A1 (en) * | 2012-06-13 | 2013-12-19 | Shell Internationale Research Maatschappij B.V. | Process for preparing an internal olefin sulfonate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1538436A (fr) * | 1966-07-14 | 1968-09-06 | Procter & Gamble | Procédé pour faire réagir des alpha-oléfines et de l'anhydride sulfurique gazeux |
-
0
- BE BE789922D patent/BE789922A/xx unknown
-
1971
- 1971-10-12 US US00188590A patent/US3755429A/en not_active Expired - Lifetime
-
1972
- 1972-10-09 DE DE2249360A patent/DE2249360A1/de active Pending
- 1972-10-10 CA CA153,558A patent/CA981278A/en not_active Expired
- 1972-10-11 ES ES407538A patent/ES407538A1/es not_active Expired
- 1972-10-11 IT IT30370/72A patent/IT968863B/it active
- 1972-10-11 FR FR7236041A patent/FR2156268B1/fr not_active Expired
- 1972-10-12 NL NL7213830A patent/NL7213830A/xx not_active Application Discontinuation
- 1972-10-12 GB GB4712572A patent/GB1367369A/en not_active Expired
- 1972-10-12 JP JP47102294A patent/JPS4861426A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2657620A1 (de) * | 1975-12-26 | 1977-07-14 | Lion Fat Oil Co Ltd | Verfahren zur herstellung hochkonzentrierter olefinsulfonatloesungen |
| EP0293913A1 (de) * | 1987-06-04 | 1988-12-07 | Raschig AG | Verfahren zur Herstellung von gegebenenfalls substituierten Ethansulfonverbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| IT968863B (it) | 1974-03-20 |
| BE789922A (fr) | 1973-04-11 |
| US3755429A (en) | 1973-08-28 |
| FR2156268A1 (cg-RX-API-DMAC10.html) | 1973-05-25 |
| ES407538A1 (es) | 1975-11-01 |
| JPS4861426A (cg-RX-API-DMAC10.html) | 1973-08-28 |
| CA981278A (en) | 1976-01-06 |
| GB1367369A (en) | 1974-09-18 |
| NL7213830A (cg-RX-API-DMAC10.html) | 1973-04-16 |
| FR2156268B1 (cg-RX-API-DMAC10.html) | 1974-08-19 |
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