GB661701A - N-acyl-n-aliphatic taurates having surface active properties - Google Patents
N-acyl-n-aliphatic taurates having surface active propertiesInfo
- Publication number
- GB661701A GB661701A GB9890/49A GB989049A GB661701A GB 661701 A GB661701 A GB 661701A GB 9890/49 A GB9890/49 A GB 9890/49A GB 989049 A GB989049 A GB 989049A GB 661701 A GB661701 A GB 661701A
- Authority
- GB
- United Kingdom
- Prior art keywords
- taurate
- octyl
- heptyl
- alkali metal
- decanoyl
- 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
- 229940104261 taurate Drugs 0.000 abstract 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- -1 iso-octyl Chemical group 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Chemical group 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 238000009736 wetting Methods 0.000 abstract 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Chemical group 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000011181 potassium carbonates Nutrition 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 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
- C11D1/88—Ampholytes; Electroneutral compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
- C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
-
- 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
- Y10S516/04—Protein or carboxylic compound containing
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)
Abstract
Compounds of the formula <FORM:0661701/IV (b)/1> in which R is an alkyl radical, R1 is a saturated aliphatic hydrocarbon radical and X is hydrogen, an alkali metal, or an ammonium group, the sum of the carbon atoms in RCO and R1 being at least 16 but not greater than 19, the number of carbon atoms in RCO being at least 8 but not greater than 14, and the number of carbon atoms in R1 being at least 5 but not greater than 8, are produced by reacting a compound of formula RCOCl, with a compound of formula <FORM:0661701/IV (b)/2> in which Y is a salt forming group, in the presence of an acid binding agent. The resulting compounds have very high wetting power. R may be heptyl, octyl, nonyl, decyl, undecyl, dodecyl or tridecyl. R1 may be amyl, isoamyl, hexyl, heptyl, octyl, iso-octyl, cyclohexyl or the like. X is hydrogen, sodium, potassium, lithium, ammonium or the like. The reaction takes place between 5 DEG and 50 DEG C. and suitable acid binding agents are p caustic soda and pyridine. The alkali metal salts of the taurines may be prepared by treating an aqueous alkaline solution of hydroxyethyl sulphonic acid and the desired amine to a temperature in the range 180-240 DEG C. The alkalinity may be supplied by the use of alkali metal hydroxide, such as caustic soda, caustic potash, sodium carbonate, potassium carbonate, &c. Examples of compounds having very high wetting properties are the sodium or other alkali metal salt of (a) N-lauryl-N-hexyl taurate; (b) N-lauroyl-N-(amyl-isoamyl mixture) taurate; (c) N-decanoyl-N-octyl taurate; (d) N - myristoyl - N - (amyl - isoamyl mixture) taurate; (e) N-decanoyl-N-heptyl taurate; (f) N-caprylyl-N-octyl taurate; (g) N-undecenoyl-N-octyl taurate; (h) N-lauroyl-N-heptyl taurate; (j) N-lauroyl-N-cyclohexyl taurate; and (k) N-decanoyl-N-(2-ethylhexyl) taurate. Specification 341,053 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32039A US2651645A (en) | 1948-06-09 | 1948-06-09 | Surface active agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB661701A true GB661701A (en) | 1951-11-28 |
Family
ID=21862772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9890/49A Expired GB661701A (en) | 1948-06-09 | 1949-04-12 | N-acyl-n-aliphatic taurates having surface active properties |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2651645A (en) |
| GB (1) | GB661701A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3668179A (en) * | 1969-10-09 | 1972-06-06 | Mobil Oil Corp | Color stabilized polyolefin resins |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2821536A (en) * | 1953-02-16 | 1958-01-28 | Ruhrchemie Ag | Production of wetting, emulsifying and washing agent |
| BE530382A (en) * | 1953-07-17 | |||
| US2964467A (en) * | 1956-05-04 | 1960-12-13 | Gen Aniline & Film Corp | Precipitation inhibiting |
| US3344174A (en) * | 1962-08-21 | 1967-09-26 | Monsanto Co | Vicinal acylamido sulfonate compounds |
| US3850610A (en) * | 1971-10-18 | 1974-11-26 | Gaf Corp | Herbicidal method |
| CN114181119B (en) * | 2021-12-18 | 2023-04-18 | 湖北天安日用化工有限公司 | Preparation method of methyl lauroyl sodium taurate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1932180A (en) * | 1929-04-12 | 1933-10-24 | Ig Farbenindustrie Ag | Sulphuric acid derivatives of amides |
| US2045015A (en) * | 1931-06-09 | 1936-06-23 | Ig Farbenindustrie Ag | Production of sulphuric derivatives of fatty acid compounds |
-
1948
- 1948-06-09 US US32039A patent/US2651645A/en not_active Expired - Lifetime
-
1949
- 1949-04-12 GB GB9890/49A patent/GB661701A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3668179A (en) * | 1969-10-09 | 1972-06-06 | Mobil Oil Corp | Color stabilized polyolefin resins |
Also Published As
| Publication number | Publication date |
|---|---|
| US2651645A (en) | 1953-09-08 |
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