DE2203815B2 - Verfahren zur herstellung von olefinsulfonaten - Google Patents
Verfahren zur herstellung von olefinsulfonatenInfo
- Publication number
- DE2203815B2 DE2203815B2 DE19722203815 DE2203815A DE2203815B2 DE 2203815 B2 DE2203815 B2 DE 2203815B2 DE 19722203815 DE19722203815 DE 19722203815 DE 2203815 A DE2203815 A DE 2203815A DE 2203815 B2 DE2203815 B2 DE 2203815B2
- Authority
- DE
- Germany
- Prior art keywords
- weight
- percent
- olefin
- olefins
- vinylidene
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 23
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 48
- -1 olefin sulfonates Chemical class 0.000 claims description 41
- 150000001336 alkenes Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000006277 sulfonation reaction Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000011552 falling film Substances 0.000 claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 35
- 239000002002 slurry Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004140 cleaning Methods 0.000 description 9
- 239000003599 detergent Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004711 α-olefin Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012459 cleaning agent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
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)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11034171A | 1971-01-27 | 1971-01-27 | |
| US16013771A | 1971-07-06 | 1971-07-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2203815A1 DE2203815A1 (de) | 1972-10-26 |
| DE2203815B2 true DE2203815B2 (de) | 1976-08-12 |
Family
ID=26807932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722203815 Ceased DE2203815B2 (de) | 1971-01-27 | 1972-01-27 | Verfahren zur herstellung von olefinsulfonaten |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5110221B1 (enrdf_load_stackoverflow) |
| BE (1) | BE778490A (enrdf_load_stackoverflow) |
| CA (1) | CA972379A (enrdf_load_stackoverflow) |
| DE (1) | DE2203815B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2123466B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1340977A (enrdf_load_stackoverflow) |
| NL (1) | NL7201132A (enrdf_load_stackoverflow) |
| SE (1) | SE7501466L (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59222466A (ja) * | 1983-05-31 | 1984-12-14 | Lion Corp | オレフインのスルホン化方法 |
| WO2020131286A1 (en) * | 2018-12-19 | 2020-06-25 | Exxonmobil Chemical Patents Inc. | Sulfonation of vinylidene olefins |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1530076A (fr) * | 1966-07-01 | 1968-06-21 | Henkel & Cie Gmbh | Procédé de préparation de produits sulfonés de couleur claire |
| JPS5220453B1 (enrdf_load_stackoverflow) * | 1968-12-11 | 1977-06-03 | ||
| BE755471A (fr) * | 1969-08-29 | 1971-02-01 | Sumitomo Chemical Co | Composition detergente de sulfonate d'olefine |
-
1972
- 1972-01-13 CA CA132,380A patent/CA972379A/en not_active Expired
- 1972-01-25 GB GB345972A patent/GB1340977A/en not_active Expired
- 1972-01-26 BE BE778490A patent/BE778490A/xx unknown
- 1972-01-27 DE DE19722203815 patent/DE2203815B2/de not_active Ceased
- 1972-01-27 NL NL7201132A patent/NL7201132A/xx unknown
- 1972-01-27 FR FR7202692A patent/FR2123466B1/fr not_active Expired
- 1972-01-27 JP JP47009541A patent/JPS5110221B1/ja active Pending
-
1975
- 1975-02-10 SE SE7501466A patent/SE7501466L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5110221B1 (enrdf_load_stackoverflow) | 1976-04-02 |
| DE2203815A1 (de) | 1972-10-26 |
| FR2123466A1 (enrdf_load_stackoverflow) | 1972-09-08 |
| SE7501466L (sv) | 1975-02-10 |
| FR2123466B1 (enrdf_load_stackoverflow) | 1974-09-13 |
| BE778490A (fr) | 1972-07-26 |
| CA972379A (en) | 1975-08-05 |
| NL7201132A (enrdf_load_stackoverflow) | 1972-07-31 |
| GB1340977A (en) | 1973-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHV | Refusal |