GB1001286A - Process for the sulphonation of fatty acids or their esters - Google Patents
Process for the sulphonation of fatty acids or their estersInfo
- Publication number
- GB1001286A GB1001286A GB29661/62A GB2966162A GB1001286A GB 1001286 A GB1001286 A GB 1001286A GB 29661/62 A GB29661/62 A GB 29661/62A GB 2966162 A GB2966162 A GB 2966162A GB 1001286 A GB1001286 A GB 1001286A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fatty acid
- trioxide
- hardened
- ethyl ester
- fatty acids
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
In the sulphonation of essentially saturated fatty acids of 6-28 C atoms per molecule, or their esters, by the addition of 1.1 to 1.8 mols of sulphur trioxide per mol of fatty acid residue, in the absence of solvents which form adducts with sulphur trioxide, 65 to 90% of the total sulphur trioxide is added at a temperature of not above 70 DEG C. and the remainder at above 70 DEG C. No sulphatable or sulphonatable groups should be present in the fatty acids to allow of sulphonation ether than at the a -hydrogen atom. The trioxide is preferably added continuously at steadily increasing temperatures the first portion at 30 DEG to 70 DEG C., preferably 40 DEG to 65 DEG C., and the residue at 75 DEG to 95 DEG C., preferably 80 DEG to 90 DEG C. The fatty acids preferably have 8-18 C atoms per molecule and an iodine value of below 5, especially below 2. Preferred fatty acids are those derived from plants and animals, e.g. lauric acid, hydrogenated vegetable fats, hydrogenated tallow, whale and fish oils. Their esters may be derived from mono- or polyhydric alcohols, e.g. hydrogenation products of oleyl oleate occurring in sperm oil or natural or synthetic wax esters. Preferably 1.2 to 1.6 moles of trioxide are used per mol of fatty acid residue. The sulphur trioxide is used in the presence of inert gases, e.g. air, N2 and CO2, the gas mixture containing 2-40%, preferably 3-20% by volume, of sulphur trioxide. The addition of the trioxide, and the variation in temperature, are adjusted so that the trioxide reacts as completely as possible. The first stage should take 2/3 to 3/4 of the total reaction time and the second stage not less than 5, preferably 10-15 minutes. The products are bleached preferably as in Specification 1,001,283. The fatty acid products, before or after bleaching, may be esterified with alcohols of 1-6 C atoms, especially monohydric alcohols. Examples are provided in which methyl laurate (made from hardened coconut oil) an ethyl ester derived from hardened coconut oil, an ethyl ester of a hardened and distilled tallow fatty acid, a sec-butyl ester of hardened coconut fatty acid, a mixture of an ethyl ester of a hardened palm kernel fatty acid and hardened palm kernel fatty acid, a mixture of hardened coconut fatty acid ethyl ester and the free acid, hardened palm kernel fatty acid ethyl ester, and hydrogenated palm kernel fatty acid, are sulphonated.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1961H0043358 DE1246718C2 (en) | 1961-08-08 | 1961-08-08 | Process for the production of sulfonated fatty acids or sulfonated fatty acid esters and optionally their salts |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1001286A true GB1001286A (en) | 1965-08-11 |
Family
ID=7155165
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29661/62A Expired GB1001286A (en) | 1961-08-08 | 1962-08-02 | Process for the sulphonation of fatty acids or their esters |
Country Status (6)
Country | Link |
---|---|
US (1) | US3256303A (en) |
CH (1) | CH421082A (en) |
DE (1) | DE1246718C2 (en) |
DK (1) | DK117139B (en) |
GB (1) | GB1001286A (en) |
NL (2) | NL140235B (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS522890B2 (en) * | 1973-11-29 | 1977-01-25 | ||
DE3047897A1 (en) * | 1980-12-19 | 1982-07-15 | Henkel KGaA, 4000 Düsseldorf | "METHOD FOR SIMPLIFYING THE PRODUCTION OF LIGHT-COLORED WASHING ACTIVE (ALPHA) SULFOUR ACID ESTERS" |
JPS58157762A (en) * | 1982-03-15 | 1983-09-19 | Lion Corp | Preparation of ester of alpha-sulfo fatty acid |
JPS58157763A (en) * | 1982-03-15 | 1983-09-19 | Lion Corp | Preparation of ester of alpha-sulfo fatty acid |
DE3319591A1 (en) * | 1983-05-30 | 1984-12-06 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR OBTAINING COLOR-STABLE LIGHT-COLORED AQUEOUS SALT PASTES FROM WASHING ACTIVE (ALPHA) SULFOUR ACID ESTERS |
DE3432324A1 (en) * | 1984-09-03 | 1986-03-13 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR CONTROLLING THE DISALINE CONTENT IN (ALPHA) SULFOURIC ACID ESTER TENSIDES |
DE3538910A1 (en) * | 1985-11-02 | 1987-05-14 | Henkel Kgaa | METHOD FOR PRODUCING MOVABLE PASTE OF WASHING ACTIVE ALPHA SULFOURIC ACID ESTER SALTS HIGH SOLIDS |
DE3834393A1 (en) * | 1988-10-10 | 1990-04-26 | Henkel Kgaa | METHOD FOR PRODUCING LIGHT-COLORED ALPHA SULFO FATTY ACID ALKYL ESTER SALTS |
DE4017467A1 (en) * | 1990-05-30 | 1991-12-05 | Henkel Kgaa | METHOD FOR PRODUCING LIGHT-COLORED ALPHA SULFOUR ACID ALKYL ESTER ALKALI METAL SALT PASTES |
US5587500A (en) * | 1993-09-17 | 1996-12-24 | The Chemithon Corporation | Sulfonation of fatty acid esters |
CN112540077B (en) * | 2020-11-30 | 2022-12-06 | 邢台学院 | Method for in-situ detection of fatty acid unsaturation degree in seeds |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1926442A (en) * | 1927-06-07 | 1933-09-12 | Ig Farbenindustrie Ag | Production of sulfonic acids of aliphatic and hydroaromatic carboxylic acids |
US2691040A (en) * | 1951-03-29 | 1954-10-05 | Universal Oil Prod Co | Sulfonation of organic compounds with sulfur trioxide |
DE967585C (en) * | 1952-10-14 | 1957-11-28 | Henkel & Cie Gmbh | Process for the production of sulfonated fatty acid nitriles |
US2878271A (en) * | 1957-05-17 | 1959-03-17 | Tennesse Corp | Neutralization of sulfonation mixtures and products thereof |
-
0
- NL NL281859D patent/NL281859A/xx unknown
-
1961
- 1961-08-08 DE DE1961H0043358 patent/DE1246718C2/en not_active Expired
-
1962
- 1962-05-15 US US194840A patent/US3256303A/en not_active Expired - Lifetime
- 1962-08-02 GB GB29661/62A patent/GB1001286A/en not_active Expired
- 1962-08-07 CH CH942662A patent/CH421082A/en unknown
- 1962-08-07 DK DK346762AA patent/DK117139B/en unknown
- 1962-08-08 NL NL62281859A patent/NL140235B/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE1246718B (en) | 1967-08-10 |
NL281859A (en) | |
NL140235B (en) | 1973-11-15 |
DK117139B (en) | 1970-03-23 |
DE1246718C2 (en) | 1974-05-22 |
CH421082A (en) | 1966-09-30 |
US3256303A (en) | 1966-06-14 |
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