DE2253896C3 - Verfahren zur Reinigung von oberflächenaktiven Mitteln - Google Patents
Verfahren zur Reinigung von oberflächenaktiven MittelnInfo
- Publication number
- DE2253896C3 DE2253896C3 DE2253896A DE2253896A DE2253896C3 DE 2253896 C3 DE2253896 C3 DE 2253896C3 DE 2253896 A DE2253896 A DE 2253896A DE 2253896 A DE2253896 A DE 2253896A DE 2253896 C3 DE2253896 C3 DE 2253896C3
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- weight
- oil
- amount
- unreacted
- 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
- 238000000034 method Methods 0.000 title claims description 27
- 239000004094 surface-active agent Substances 0.000 title claims description 27
- 238000004140 cleaning Methods 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- -1 aliphatic alcohols Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 239000003921 oil Substances 0.000 description 33
- 239000000126 substance Substances 0.000 description 15
- 238000000605 extraction Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- 150000003871 sulfonates Chemical class 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 235000019645 odor Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000035943 smell Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- 108010053481 Antifreeze Proteins Proteins 0.000 description 1
- 206010013911 Dysgeusia Diseases 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
- 239000007832 Na2SO4 Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004711 α-olefin 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
- C11D1/146—Sulfuric 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
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- 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
-
- 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
- Y10S516/05—Organic amine, amide, or n-base containing
-
- 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
- Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
- Y10S516/909—The agent contains organic compound containing sulfoxy*
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8768271A JPS5414075B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-11-05 | 1971-11-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2253896A1 DE2253896A1 (de) | 1973-05-10 |
| DE2253896B2 DE2253896B2 (de) | 1979-07-05 |
| DE2253896C3 true DE2253896C3 (de) | 1980-03-06 |
Family
ID=13921689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2253896A Expired DE2253896C3 (de) | 1971-11-05 | 1972-11-03 | Verfahren zur Reinigung von oberflächenaktiven Mitteln |
Country Status (3)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5716097A (en) * | 1980-07-04 | 1982-01-27 | Lion Corp | Production of deodorized alkyl ether sulfate aqueous concentrate |
| DE3044488A1 (de) * | 1980-11-26 | 1982-07-01 | Henkel KGaA, 4000 Düsseldorf | "verfahren zur herstellung von ehtersulfaten mit erniedrigtem dioxangehalt" |
| JPS59106455A (ja) * | 1982-12-09 | 1984-06-20 | Lion Corp | 界面活性剤スラリ−中の未反応油分の除去方法 |
| JPS6041534A (ja) * | 1983-08-12 | 1985-03-05 | Sunstar Kaihatsu Kk | 顆粒状界面活性剤およびその製法 |
| US5075041A (en) * | 1990-06-28 | 1991-12-24 | Shell Oil Company | Process for the preparation of secondary alcohol sulfate-containing surfactant compositions |
| DE4131118A1 (de) * | 1991-09-19 | 1993-03-25 | Henkel Kgaa | Verfahren zur herstellung geschmacksneutraler pasten von alkylethersulfaten in glycerin |
| US5349101A (en) * | 1992-05-28 | 1994-09-20 | Shell Oil Company | Process for the preparation of secondary alkyl sulfate-containing surfactant compositions |
| US5290484A (en) * | 1992-11-12 | 1994-03-01 | Shell Oil Company | Process for the preparation of secondary alkyl sulfate-containing surfactant compositions |
| US5250718A (en) * | 1992-09-28 | 1993-10-05 | Shell Oil Company | Process for the preparation of secondary alkyl sulfate-containing surfactant compositions |
| US5281366A (en) * | 1992-09-17 | 1994-01-25 | Shell Oil Company | Process for the preparation of secondary alkyl sulfate-containing surfactant compositions |
| AU674920B2 (en) * | 1992-12-15 | 1997-01-16 | Shell Internationale Research Maatschappij B.V. | Secondary alkyl sulphate/zeolite-containing surfactant composition |
| JP2003502065A (ja) * | 1999-06-18 | 2003-01-21 | アドヴァンスト リサーチ アンド テクノロジー インスティチュート、インコーポレイティッド | 高められた増殖能を持つ心筋細胞、およびその製造および使用法 |
| US20030116290A1 (en) * | 2001-12-20 | 2003-06-26 | 3M Innovative Properties Company | Continuous process for controlled evaporation of black liquor |
| US6869501B2 (en) | 2001-12-20 | 2005-03-22 | 3M Innovative Properties Company | Continuous process for controlled concentration of colloidal solutions |
| USD801123S1 (en) | 2016-02-05 | 2017-10-31 | Yeti Coolers, Llc | Insulating device |
| JP6759173B2 (ja) | 2017-09-20 | 2020-09-23 | 株式会社東芝 | 二次電池、電池パック及び車両 |
| USD848219S1 (en) | 2017-10-30 | 2019-05-14 | Yeti Coolers, Llc | Backpack cooler |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2103255A (en) * | 1934-11-09 | 1937-12-28 | Standard Oil Dev Co | Improved process for preparation of sulphuric derivatives |
| US2945818A (en) * | 1955-02-01 | 1960-07-19 | Atlas Powder Co | Process for preparing surface active compositions |
-
1971
- 1971-11-05 JP JP8768271A patent/JPS5414075B2/ja not_active Expired
-
1972
- 1972-10-31 US US302511A patent/US3893940A/en not_active Expired - Lifetime
- 1972-11-03 DE DE2253896A patent/DE2253896C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3893940A (en) | 1975-07-08 |
| DE2253896A1 (de) | 1973-05-10 |
| DE2253896B2 (de) | 1979-07-05 |
| JPS5414075B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-06-04 |
| JPS4852687A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: LION CORP., TOKYO, JP |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. KERN, R., DIPL.-ING. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |