JP2015506340A - 内部オレフィンスルホナートを調製するための方法 - Google Patents
内部オレフィンスルホナートを調製するための方法 Download PDFInfo
- Publication number
- JP2015506340A JP2015506340A JP2014548095A JP2014548095A JP2015506340A JP 2015506340 A JP2015506340 A JP 2015506340A JP 2014548095 A JP2014548095 A JP 2014548095A JP 2014548095 A JP2014548095 A JP 2014548095A JP 2015506340 A JP2015506340 A JP 2015506340A
- Authority
- JP
- Japan
- Prior art keywords
- internal olefin
- base
- sulfonated
- weight
- suitably
- 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 160
- -1 olefin sulfonates Chemical class 0.000 title claims abstract description 59
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001336 alkenes Chemical class 0.000 claims abstract description 113
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 239000002585 base Substances 0.000 claims description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 239000013543 active substance Substances 0.000 claims description 20
- 239000002736 nonionic surfactant Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 description 37
- 238000006277 sulfonation reaction Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 27
- 230000007062 hydrolysis Effects 0.000 description 26
- 238000006460 hydrolysis reaction Methods 0.000 description 26
- 239000003921 oil Substances 0.000 description 23
- 239000004094 surface-active agent Substances 0.000 description 15
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 150000008053 sultones Chemical class 0.000 description 11
- 239000004711 α-olefin Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 239000004034 viscosity adjusting agent Substances 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- BJZYYSAMLOBSDY-UHFFFAOYSA-N 2-butoxybutan-1-ol Chemical compound CCCCOC(CC)CO BJZYYSAMLOBSDY-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004614 Process Aid Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015115 caffè latte Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012632 extractable Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
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
- C07C303/22—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 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/20—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11195469 | 2011-12-23 | ||
| EP11195469.9 | 2011-12-23 | ||
| PCT/EP2012/076804 WO2013093075A1 (en) | 2011-12-23 | 2012-12-21 | Process for preparing an internal olefin sulfonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2015506340A true JP2015506340A (ja) | 2015-03-02 |
Family
ID=47436013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014548095A Pending JP2015506340A (ja) | 2011-12-23 | 2012-12-21 | 内部オレフィンスルホナートを調製するための方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9688621B2 (https=) |
| EP (1) | EP2794557A1 (https=) |
| JP (1) | JP2015506340A (https=) |
| CN (1) | CN104053644A (https=) |
| BR (1) | BR112014015588A2 (https=) |
| CA (1) | CA2858773A1 (https=) |
| CO (1) | CO7010823A2 (https=) |
| EA (1) | EA201491266A1 (https=) |
| IN (1) | IN2014CN04421A (https=) |
| MX (1) | MX2014007373A (https=) |
| SG (1) | SG11201403071WA (https=) |
| WO (1) | WO2013093075A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017209118A1 (ja) * | 2016-05-31 | 2017-12-07 | 花王株式会社 | 繊維製品用液体洗浄剤組成物 |
| US11053456B2 (en) | 2016-05-31 | 2021-07-06 | Kao Corporation | Detergent composition for textile products |
| US11124743B2 (en) | 2016-05-31 | 2021-09-21 | Kao Corporation | Liquid detergent composition for textile products |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104785159B (zh) * | 2015-03-23 | 2017-10-13 | 中国日用化学工业研究院 | 一种制备磺酸盐与硫酸酯盐复合阴离子表面活性剂的工艺 |
| HK1251929B (en) | 2015-05-07 | 2020-01-10 | Rhodia Operations | Process for the decarboxylative ketonization of fatty acids or fatty acid derivatives |
| CN105462506A (zh) * | 2015-11-14 | 2016-04-06 | 华玉叶 | 一种轮胎光亮剂 |
| CN105238275A (zh) * | 2015-11-14 | 2016-01-13 | 华玉叶 | 一种轮胎光亮剂 |
| CN105602456A (zh) * | 2015-11-14 | 2016-05-25 | 华玉叶 | 一种轮胎光亮剂 |
| US10660837B2 (en) | 2016-08-31 | 2020-05-26 | Kao Corporation | Oral composition and oral plaque dispersion agent |
| 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 |
| CN118145912A (zh) * | 2024-01-15 | 2024-06-07 | 科之杰新材料集团有限公司 | 一种轻质混凝土用复合引气剂及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6059903B2 (ja) | 1977-08-25 | 1985-12-27 | ライオン株式会社 | 内部オレフインスルホン酸塩の製造法 |
| US4248793A (en) | 1979-09-26 | 1981-02-03 | The Lion Fat & Oil Co., Ltd. | Process for the production of internal olefin sulfonate |
| US4579690A (en) | 1984-12-28 | 1986-04-01 | Shell Oil Company | Process for the deoiling of olefin sulfonates |
| GB8817293D0 (en) | 1988-07-20 | 1988-08-24 | Shell Int Research | Process for preparation of internal olefin sulphonates |
| GB9000719D0 (en) | 1990-01-12 | 1990-03-14 | Shell Int Research | Process for the preparation of beta-substituted sulphonic acids and/or sulphonates |
| US5488148A (en) * | 1993-09-01 | 1996-01-30 | Vista Chemical Company | Process for sulfonating internal olefins |
| US5648585A (en) | 1993-12-29 | 1997-07-15 | Murray; Brendan Dermot | Process for isomerizing linear olefins to isoolefins |
| US5510306A (en) | 1993-12-29 | 1996-04-23 | Shell Oil Company | Process for isomerizing linear olefins to isoolefins |
| AU6257996A (en) | 1995-06-07 | 1996-12-30 | Pq Corporation | Process for preparing ferrierite |
| US5849960A (en) | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| EP1180096A4 (en) * | 1999-04-27 | 2004-12-15 | Sasol North America Inc | PROCESS FOR THE PREPARATION AND ISOLATION OF SULPHONE INTERNAL OLEFINS |
| AP2011006003A0 (en) * | 2009-05-05 | 2011-12-31 | Stepan Co | Sulfonated internal olefin surfactant for enhancedoil recovery. |
-
2012
- 2012-12-21 CN CN201280067014.4A patent/CN104053644A/zh active Pending
- 2012-12-21 EA EA201491266A patent/EA201491266A1/ru unknown
- 2012-12-21 CA CA2858773A patent/CA2858773A1/en not_active Abandoned
- 2012-12-21 WO PCT/EP2012/076804 patent/WO2013093075A1/en not_active Ceased
- 2012-12-21 MX MX2014007373A patent/MX2014007373A/es unknown
- 2012-12-21 SG SG11201403071WA patent/SG11201403071WA/en unknown
- 2012-12-21 EP EP12806512.5A patent/EP2794557A1/en not_active Withdrawn
- 2012-12-21 IN IN4421CHN2014 patent/IN2014CN04421A/en unknown
- 2012-12-21 JP JP2014548095A patent/JP2015506340A/ja active Pending
- 2012-12-21 US US14/366,757 patent/US9688621B2/en not_active Expired - Fee Related
- 2012-12-21 BR BR112014015588A patent/BR112014015588A2/pt not_active IP Right Cessation
-
2014
- 2014-07-17 CO CO14155206A patent/CO7010823A2/es unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017209118A1 (ja) * | 2016-05-31 | 2017-12-07 | 花王株式会社 | 繊維製品用液体洗浄剤組成物 |
| US11053456B2 (en) | 2016-05-31 | 2021-07-06 | Kao Corporation | Detergent composition for textile products |
| US11124743B2 (en) | 2016-05-31 | 2021-09-21 | Kao Corporation | Liquid detergent composition for textile products |
| US11248195B2 (en) | 2016-05-31 | 2022-02-15 | Kao Corporation | Liquid detergent composition for textile products comprising an internal olefin sulfonate/organic solvent mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| EA201491266A1 (ru) | 2014-09-30 |
| CA2858773A1 (en) | 2013-06-27 |
| MX2014007373A (es) | 2014-08-27 |
| EP2794557A1 (en) | 2014-10-29 |
| BR112014015588A2 (pt) | 2017-08-22 |
| SG11201403071WA (en) | 2014-08-28 |
| IN2014CN04421A (https=) | 2015-09-04 |
| WO2013093075A1 (en) | 2013-06-27 |
| US20140336409A1 (en) | 2014-11-13 |
| CO7010823A2 (es) | 2014-07-31 |
| CN104053644A (zh) | 2014-09-17 |
| US9688621B2 (en) | 2017-06-27 |
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