DE69311739T3 - Herstellung eines detergens - Google Patents
Herstellung eines detergensInfo
- Publication number
- DE69311739T3 DE69311739T3 DE69311739T DE69311739T DE69311739T3 DE 69311739 T3 DE69311739 T3 DE 69311739T3 DE 69311739 T DE69311739 T DE 69311739T DE 69311739 T DE69311739 T DE 69311739T DE 69311739 T3 DE69311739 T3 DE 69311739T3
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- formula
- stabilizer
- compounds
- primary
- 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 - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003599 detergent Substances 0.000 title description 19
- 239000003381 stabilizer Substances 0.000 claims description 70
- 239000002253 acid Substances 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 23
- 238000006277 sulfonation reaction Methods 0.000 claims description 21
- 150000003138 primary alcohols Chemical class 0.000 claims description 19
- -1 alkyl sulfuric acid Chemical compound 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 239000002994 raw material Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 229910004727 OSO3H Inorganic materials 0.000 claims description 3
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 238000007046 ethoxylation reaction Methods 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000005416 organic matter Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000008051 alkyl sulfates Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- IRTCJFCIQKNFPP-UHFFFAOYSA-N 2-methyl-1,4-dioxane Chemical compound CC1COCCO1 IRTCJFCIQKNFPP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 230000009471 action Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940096386 coconut alcohol Drugs 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000004094 surface-active agent 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
- C11D1/66—Non-ionic compounds
- C11D1/83—Mixtures of non-ionic with anionic compounds
-
- 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
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric 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
-
- 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
- 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
- C11D1/37—Mixtures of compounds all of which are anionic
-
- 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
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929226003A GB9226003D0 (en) | 1992-12-14 | 1992-12-14 | Detergent production |
| PCT/EP1993/003477 WO1994013633A1 (en) | 1992-12-14 | 1993-12-07 | Detergent production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE69311739D1 DE69311739D1 (de) | 1997-07-24 |
| DE69311739T2 DE69311739T2 (de) | 1997-10-30 |
| DE69311739T3 true DE69311739T3 (de) | 2001-06-07 |
Family
ID=10726555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69311739T Expired - Lifetime DE69311739T3 (de) | 1992-12-14 | 1993-12-07 | Herstellung eines detergens |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5466851A (enExample) |
| EP (1) | EP0673365B2 (enExample) |
| JP (1) | JPH08504420A (enExample) |
| AU (1) | AU5698694A (enExample) |
| BR (1) | BR9307642A (enExample) |
| CA (1) | CA2151463A1 (enExample) |
| CZ (1) | CZ153095A3 (enExample) |
| DE (1) | DE69311739T3 (enExample) |
| ES (1) | ES2105613T5 (enExample) |
| GB (1) | GB9226003D0 (enExample) |
| HU (1) | HUT73358A (enExample) |
| IN (1) | IN180471B (enExample) |
| MY (1) | MY114242A (enExample) |
| PH (1) | PH31155A (enExample) |
| PL (1) | PL309362A1 (enExample) |
| SK (1) | SK77495A3 (enExample) |
| WO (1) | WO1994013633A1 (enExample) |
| ZA (1) | ZA939324B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE9422172U1 (de) | 1993-04-26 | 1998-09-17 | St. Louis University, St. Louis, Mo. | Angabe der Position einer chirurgischen Sonde |
| GB9518860D0 (en) * | 1995-09-14 | 1995-11-15 | Unilever Plc | Detergent manufacture |
| WO2014072840A1 (en) * | 2012-11-12 | 2014-05-15 | Galaxy Surfactants Ltd. | Flowable, high active, aqueous fatty alkyl sulfates |
| EP3004307A1 (en) | 2013-05-24 | 2016-04-13 | The Procter & Gamble Company | Low ph detergent composition comprising nonionic surfactants |
| US9840681B2 (en) | 2013-05-24 | 2017-12-12 | The Procter & Gamble Company | Concentrated surfactant composition |
| US10519400B2 (en) | 2013-05-24 | 2019-12-31 | The Procter & Gamble Company | Low PH detergent composition |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2098114A (en) * | 1935-10-17 | 1937-11-02 | Procter & Gamble | Process for sulphonating alcohols |
| US2923728A (en) * | 1957-11-19 | 1960-02-02 | Du Pont | Process of reacting organic compounds with sulfur trioxide |
| NL299140A (enExample) * | 1962-10-12 | |||
| US3413331A (en) * | 1965-03-26 | 1968-11-26 | Standard Chem Products Inc | Sulfation of a mixture of primary and secondary alcohols |
| US3755407A (en) * | 1967-02-10 | 1973-08-28 | Chevron Res | Sulfation process for secondary alcohols |
| PL93459B1 (enExample) * | 1973-09-28 | 1977-05-30 | ||
| US4464292A (en) * | 1981-01-02 | 1984-08-07 | Lengyel Stephen P | Mixed ethoxylated alcohol/ethoxy sulfate surfactants and synthetic detergents incorporating the same |
| ES8607378A1 (es) † | 1984-08-06 | 1986-05-16 | Kao Corp | Una composicion detergente en polvo de gran densidad |
| WO1991013057A1 (en) * | 1990-03-01 | 1991-09-05 | The Procter & Gamble Company | Co-sulfation of ethoxylated alcohols and unsaturated fatty alcohols |
| DE4109250A1 (de) * | 1991-03-21 | 1992-09-24 | Henkel Kgaa | Verfahren zur herstellung von hochkonzentrierten fettalkoholsulfat-pasten |
| ES2131524T3 (es) † | 1992-03-10 | 1999-08-01 | Procter & Gamble | Pastas detergentes muy activas. |
-
1992
- 1992-12-14 GB GB929226003A patent/GB9226003D0/en active Pending
-
1993
- 1993-12-07 DE DE69311739T patent/DE69311739T3/de not_active Expired - Lifetime
- 1993-12-07 CZ CZ951530A patent/CZ153095A3/cs unknown
- 1993-12-07 BR BR9307642A patent/BR9307642A/pt not_active Application Discontinuation
- 1993-12-07 ES ES94902739T patent/ES2105613T5/es not_active Expired - Lifetime
- 1993-12-07 WO PCT/EP1993/003477 patent/WO1994013633A1/en not_active Ceased
- 1993-12-07 HU HU9501734A patent/HUT73358A/hu unknown
- 1993-12-07 SK SK774-95A patent/SK77495A3/sk unknown
- 1993-12-07 EP EP94902739A patent/EP0673365B2/en not_active Expired - Lifetime
- 1993-12-07 PL PL93309362A patent/PL309362A1/xx unknown
- 1993-12-07 CA CA002151463A patent/CA2151463A1/en not_active Abandoned
- 1993-12-07 JP JP6513784A patent/JPH08504420A/ja active Pending
- 1993-12-07 AU AU56986/94A patent/AU5698694A/en not_active Abandoned
- 1993-12-08 IN IN414BO1993 patent/IN180471B/en unknown
- 1993-12-10 PH PH47423A patent/PH31155A/en unknown
- 1993-12-13 ZA ZA939324A patent/ZA939324B/xx unknown
- 1993-12-13 MY MYPI93002694A patent/MY114242A/en unknown
- 1993-12-14 US US08/167,260 patent/US5466851A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR9307642A (pt) | 1999-05-25 |
| ES2105613T5 (es) | 2001-02-01 |
| GB9226003D0 (en) | 1993-02-10 |
| MY114242A (en) | 2002-09-30 |
| DE69311739T2 (de) | 1997-10-30 |
| ES2105613T3 (es) | 1997-10-16 |
| HU9501734D0 (en) | 1995-08-28 |
| ZA939324B (en) | 1995-06-13 |
| DE69311739D1 (de) | 1997-07-24 |
| IN180471B (enExample) | 1998-02-07 |
| US5466851A (en) | 1995-11-14 |
| PL309362A1 (en) | 1995-10-02 |
| EP0673365B1 (en) | 1997-06-18 |
| AU5698694A (en) | 1994-07-04 |
| HUT73358A (en) | 1996-07-29 |
| WO1994013633A1 (en) | 1994-06-23 |
| CA2151463A1 (en) | 1994-06-23 |
| CZ153095A3 (en) | 1995-10-18 |
| EP0673365A1 (en) | 1995-09-27 |
| JPH08504420A (ja) | 1996-05-14 |
| SK77495A3 (en) | 1995-11-08 |
| EP0673365B2 (en) | 2000-11-02 |
| PH31155A (en) | 1998-03-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8366 | Restricted maintained after opposition proceedings |