GB1003552A - Sulphonation process for the production of detergent compositions - Google Patents
Sulphonation process for the production of detergent compositionsInfo
- Publication number
- GB1003552A GB1003552A GB903061A GB903061A GB1003552A GB 1003552 A GB1003552 A GB 1003552A GB 903061 A GB903061 A GB 903061A GB 903061 A GB903061 A GB 903061A GB 1003552 A GB1003552 A GB 1003552A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonation
- lauryl alcohol
- acid
- product
- lauric
- 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
- 239000000203 mixture Substances 0.000 title abstract 6
- 239000003599 detergent Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 12
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 9
- 230000003472 neutralizing effect Effects 0.000 abstract 9
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- 239000006259 organic additive Substances 0.000 abstract 6
- 239000004166 Lanolin Substances 0.000 abstract 5
- ZZNDQCACFUJAKJ-UHFFFAOYSA-N 1-phenyltridecan-1-one Chemical compound CCCCCCCCCCCCC(=O)C1=CC=CC=C1 ZZNDQCACFUJAKJ-UHFFFAOYSA-N 0.000 abstract 4
- 239000005639 Lauric acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 150000004665 fatty acids Chemical class 0.000 abstract 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 3
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 2
- 244000060011 Cocos nucifera Species 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Polymers CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 abstract 2
- 150000004996 alkyl benzenes Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000002939 deleterious effect Effects 0.000 abstract 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 150000002190 fatty acyls Chemical group 0.000 abstract 2
- 235000019388 lanolin Nutrition 0.000 abstract 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 1
- -1 alkyl phenols Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000002453 shampoo Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- 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
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Detergent Compositions (AREA)
Abstract
Detergent compositions are prepared by sulphonating a sulphonatable organic compound and neutralizing the sulphonation product, the sulphonation being carried out in the presence of an organic additive which is substantially inert to sulphonation under the sulphonation conditions employed, which has no deleterious effect on the detergent activity of the sulphonation product and which remains, after the reaction, to form part of the composition. (The term "sulphonation" used herein includes also sulphamation and sulphation as well as actual sulphonation.) The organic additive preferably has surface-active properties itself, or is capable of reaction to form a surface-active derivative. Sulphonatable compounds specified are lauryl alcohol, ethoxylated lauryl alcohol, alkyl-benzenes and polyalkoxy-alkyl-phenols. Preferred types of organic additives are fatty acyl alkylolamides and their alkoxylated derivatives, C8 to C18 fatty acids, wool wax alcohols and their alkoxylated derivatives, and alkoxylated or poly-alkoxylated alkylphenols. In the Examples: (1) dodecylbenzene is sulphonated with SO3 in the presence of tetraethoxy nonylphenol and the product neutralized with NaOH; (2) lauryl alcohol is sulphated with chlorosulphonic acid in the presence of coconut fatty acid mono-isopropanolamide and the product neutralized with aqueous triethanolamine; (3) tetra-ethoxy nonylphenol is treated with amino-sulphonic acid in the presence of glycerol, the ammonium sulphate salt product being self-neutralized; (4) lauryl alcohol is sulphated with chlorosulphonic in the presence of lauric acid and both the sulphated alcohol and the lauric acid are neutralized with aqueous triethanolamine, this composition being suitable for use as a gel shampoo; (5) and (6) lauryl alcohol is sulphated with chlorosulphonic acid in the presence of, respectively, lauric diethanolamide and ethoxylated lauric diethanolamide and the product neutralized with aqueous triethanolamine; (7) ethoxylated lauryl alcohol is sulphated with chlorosulphonic acid in the presence of polyethoxylated lauric monoethanolamide and the product neutralized with NaOH and (8) lauryl alcohol is sulphated with chlorosulphonic acid in the presence of wool wax alcohol and the product neutralized with aqueous triethanolamine.ALSO:A sulphonation process for the production of a detergent composition comprises reacting a sulphonatable organic compound at elevated temperature with a sulphonating agent and neutralizing the sulphonation product, the sulphonation being carried out in the presence of an organic additive which is substantially inert to sulphonation under the sulphonation conditions employed, which has no deleterious effect on the detergent activity of the sulphonation product of said sulphonatable compound and which remains, after the reaction, to form part of the composition, the amount of sulphonating agent employed being from 1 to 1.1 mols. per mol. of said sulphonatable compound. (The term "sulphonation" used herein includes also sulphamation and sulphation as well as actual sulphonation.) The organic additive preferably has surface-active properties itself, or is capable of reaction to form a surface-active derivative. Suitable sulphonatable compounds specified are lauryl alcohol, ethoxylated lauryl alcohol, alkylbenzenes and polyalkoxyalkyl phenols. Preferred types of organic additives are fatty acyl alkylolamides and their alkoxylated derivatives, C8 to C18 fatty acids, wool wax alcohols and alkoxylated wool wax alcohols, and alkoxylated or polyalkoxylated alkyl phenols. Examples describe the sulphonation of (1) dodecyl benzene with sulphur trioxide in the presence of tetraethoxy nonylphenol, neutralising with NaOH (2) lauryl alcohol with chlorosulphonic acid in the presence of coconut fatty acid mono-isopropanolamide, neutralising with aqueous triethanolamine (3) tetraethoxy nonylphenol with amino-sulphonic acid in the presence of glycerol, the ammonium salt product being self-neutralised (4) lauryl alcohol with chlorosulphonic acid in the presence of lauric acid, neutralising both the sulphonation product and the lauric acid with aqueous triethanolamine (5) lauryl alcohol with chlorosulphonic acid in the presence of lauric diethanolamide, neutralising with aqueous triethanolamine (6) lauryl alcohol with chlorosulphonic acid in the presence of ethoxylated lauric diethanolamide, neutralising with aqueous triethanolamine (7) ethoxylated lauryl alcohol with chlorosulphonic acid in the presence of polyethoxylated lauric mono - ethanolamide, neutralising with NaOH and (8) lauryl alcohol with chlorosulphonic acid in the presence of wool wax alcohol, neutralising with aqueous triethanolamine.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE605278D BE605278A (en) | 1961-03-13 | ||
| GB903061A GB1003552A (en) | 1961-03-13 | 1961-03-13 | Sulphonation process for the production of detergent compositions |
| FR862800A FR1293265A (en) | 1961-03-13 | 1961-05-25 | Process for the preparation of sulfonated organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB903061A GB1003552A (en) | 1961-03-13 | 1961-03-13 | Sulphonation process for the production of detergent compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1003552A true GB1003552A (en) | 1965-09-08 |
Family
ID=9864033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB903061A Expired GB1003552A (en) | 1961-03-13 | 1961-03-13 | Sulphonation process for the production of detergent compositions |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE605278A (en) |
| GB (1) | GB1003552A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2320933A1 (en) * | 1972-04-28 | 1973-11-22 | Lion Fat Oil Co Ltd | METHOD FOR THIN FILM SULFONATION OF SULFONABLE REACTION PARTICIPANTS |
-
0
- BE BE605278D patent/BE605278A/xx unknown
-
1961
- 1961-03-13 GB GB903061A patent/GB1003552A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2320933A1 (en) * | 1972-04-28 | 1973-11-22 | Lion Fat Oil Co Ltd | METHOD FOR THIN FILM SULFONATION OF SULFONABLE REACTION PARTICIPANTS |
Also Published As
| Publication number | Publication date |
|---|---|
| BE605278A (en) |
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