US2968664A - Fatty acid esters of hydroxyalkanesulfonic acid amine salts - Google Patents
Fatty acid esters of hydroxyalkanesulfonic acid amine salts Download PDFInfo
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- US2968664A US2968664A US718412A US71841258A US2968664A US 2968664 A US2968664 A US 2968664A US 718412 A US718412 A US 718412A US 71841258 A US71841258 A US 71841258A US 2968664 A US2968664 A US 2968664A
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- US
- United States
- Prior art keywords
- salt
- fatty acid
- hydroxyalkanesulfonic
- acid
- amine
- 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
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- -1 Fatty acid esters Chemical class 0.000 title claims description 109
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 52
- 239000000194 fatty acid Substances 0.000 title claims description 52
- 229930195729 fatty acid Natural products 0.000 title claims description 52
- 239000002253 acid Substances 0.000 title claims description 51
- 239000000203 mixture Substances 0.000 claims description 15
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000003946 cyclohexylamines Chemical class 0.000 description 13
- 229940045996 isethionic acid Drugs 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000003939 benzylamines Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 4
- 150000001263 acyl chlorides Chemical class 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 3
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 3
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical group CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 2
- WSRXLNLZLUNDKZ-UHFFFAOYSA-N 2-octadecanoyloxyethanesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCS(O)(=O)=O WSRXLNLZLUNDKZ-UHFFFAOYSA-N 0.000 description 2
- ZWDUZVBUHJVJNB-UHFFFAOYSA-N 2-octanoyloxyethanesulfonic acid Chemical compound CCCCCCCC(=O)OCCS(O)(=O)=O ZWDUZVBUHJVJNB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KMBRJVMBQNMRDM-UHFFFAOYSA-N 1-hydroxybutane-1-sulfonic acid Chemical compound CCCC(O)S(O)(=O)=O KMBRJVMBQNMRDM-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QKXPXFJKDHSDKF-UHFFFAOYSA-N 2-hexadecanoyloxyethanesulfonic acid Chemical compound CCCCCCCCCCCCCCCC(=O)OCCS(O)(=O)=O QKXPXFJKDHSDKF-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 101000740206 Mus musculus Sal-like protein 1 Proteins 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000012822 chemical development Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- YMRKWTHZKSAVSR-UHFFFAOYSA-N hydrogen sulfite;tris(2-hydroxyethyl)azanium Chemical compound OS(O)=O.OCCN(CCO)CCO YMRKWTHZKSAVSR-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- WUVDDRXOROOPOZ-UHFFFAOYSA-N n,n-diethylethanamine;sulfurous acid Chemical compound OS([O-])=O.CC[NH+](CC)CC WUVDDRXOROOPOZ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- JKDPPFICEBQUDR-UHFFFAOYSA-N phenylmethanamine;sulfurous acid Chemical compound OS(O)=O.NCC1=CC=CC=C1 JKDPPFICEBQUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000013875 sodium salts of fatty acid Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
Definitions
- This invention relates to new compositions of matter and particularly to fatty acid esters of vic-hydroxyalkanesulfonic acid amine salts representable by the conventional formula wherein the group RCO corresponds to an aliphatic carboxylic acid RCO H having from eight to twenty carbon atoms, the symbol R' represents a vicinal bivalent alkylene radical having from two to four carbon atoms, and the symbol HAm represents an ammonium cation corresponding to a primary, secondary, or tertiary amine having alkyl, cycloalkyl, aralkyl, hydroxyalkyl, or aminoalkyl substitutents in which the total number of carbon atoms is from one to twenty.
- Examples of the new fatty acid esters of hydroxyalkanesulfonic acid amine salts include ones which are esters of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid, ones wherein the alkylene radical corresponds to the ethylene, propylene, and butylene radicals, and ones in which the sulfonic acid salt is that of methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, monoethanolamine, diethanolamine, triethanolamine, the isopropanolamines, cyclohexylamine, dicyclohexylamine, benzylamine, and ethylenediamine.
- Triethylamine salt of 2-sulfoethyl caprylate 2-sulfoethyl caprylate
- fatty acid esters of hydroxyalkanesulfonic acid amine salts from the disclosure in the preceding paragraph of specific carboxylic acids, specificalkylene radicals corresponding to the hydroxyalkanesultonic acids, and specific amines.
- Mixtures of fatty acid esters of hydroxyalkanesulfonic acid amine salts are also contemplated, for example, the mixtures correspondingto represents an olefin oxide such as ethylene oxide, 1,2- propylene. oxide, 1,2-butylene oxide, 2,3-butylene oxide, or isobutylene oxide and wherein HSO HAm represents States Patent mixed fatty acids, mixed hydroxyalkanesulfonic acids, and or mixed amines.
- alkali metal e.g. sodium
- the present amine salts of fatty acid esters of hydroxyalkanesulfonic acids are new and advantageous over the alkali metal salts.
- the new fatty acid esters of hydroxyalkanesulfonic acid amine salts can be prepared by esterification reaction between a fatty acid halide such as a fatty acid chloride and a vic-hydroxyalkanesulfonic acid amine salt, such reaction being representable by the equation:
- the vichydroxyalkarresulfonic acid amine salts employed as starting material in this reaction can be obtained by interaction of an alkylene epoxide and an aqueous amine bisulfite in accordance with the equation:
- amine salts of vic-hydroxyalkanesulfonic acids is fully set forth in copending application of Arthur R. Sexton, Serial No. 670,381, filed July 8, 1957, and comprises mixing and reacting an olefin oxide with an amine bisulfite salt in an aqueous medium having a pH value of not less than 4 until the bisulfite salt is substantially consumed.
- the amine salts can also be made by stoichiometric reaction of the basic amine and a vic-hydroxyalkanesulfonic acid.
- mixed vic-hydroxyalkanesulfonic acid amine salts be prepared from mixtures of olefin oxides and/or from mixtures of amines and that such mixed vic-hydroxyalkanesulfonic acid amine salts be subsequently reacted with a fatty acid halide or mixture of fatty acid halides.
- hydroxyalkanesulfonic acid is used herein to mean a vic-hydroxyalkanesulfonic acid.
- the preparation of the new fatty esters of hydroxyalkanesulfonic acid amine salts by reaction of a fatty acid halide with a hydroxyalkanesulfonic acid amine salt' is preferably carried out by heating a mixture of the fatty acid halide and the hydroxyalkanesulfonic acid amine salt starting materials at a temperature of from 70 to C. under a reduced pressure of not more than 200 mm. of mercury, absolute pressure, preferably while subjecting the reaction mixture to mechanical working, while removing the evolved hydrogen halide from the reaction zone as swiftly and thoroughly as possible.
- the starting materials are employed in amounts corresponding to an equivalent or slight excess of the amine salt of the hydroxyalkanesulfonic acid relative to the fatty acid halide in order to insure complete consumption of the'latter.
- the fatty acid halide is added to the hydroxyalkanesulfonic acid salt under reaction conditions at rates corresponding to the rate of consumption of the acyl halide by the ester-forming reaction.
- reaction When a substantially theoretical amount of hydrogen halide has been evolved from the reaction mixture, the reactionis regarded as complete, and the resulting product is essentially the fatty acid ester of the hydroxyalkanesulfonic acid amine salt.
- reaction product as described above is essentially the fatty acid ester of the hydroxyalkanesulfonic acid amine salt, it can be used as such for many purposes. If necessary or desirable, it can be further purified by crystallization and/or extraction with selective solvents.
- the new fatty acid esters of hydroxyalkanesulfonic acid amine salts are advantageously useful as, and in the preparation of, liquid detergents, textile scrubbing aids, surfactants, and wetting agents in aqueous and nonaqueous compositions.
- the new fatty acid esters of hydroxyalkanesulfonic acid amine salts are less irritating to the skin and less injurious to delicate fabrics than are the harsh alkali detergents.
- Example 1 Preparation of triethanolamine salt of 2- sulfoethyl ester of coconut oil fatty acids
- a charge of 534 grams of the triethanolamine salt of isethionic acid was placed in a sigma-blade mixer.
- the salt was previously obtained by reaction of ethylene oxide on triethanolamine bisulfite salt in water solution and recovery of the resulting triethanolamine salt of isethionic acid.
- the salt was heated to temperatures in the range of from 110 to 115 C. under 200 mm. of mercury, absolute pressure, while 410 grams of the acyl chlorides corresponding to the fatty acids of coconut oil was added dropwise over a period of 0.5 hour. Heating was continued for an additional hours while the pressure was progressively reduced to 20 mm. of mercury absolute.
- Example 2 Preparatin of triethylamine salt of 2- salfoethyl caprylate The procedure described above in Example 1 was substantially repeated using as starting materials approximately stoichiometric quantities of the triethylamine salt of isethionic acid and capryloyl chloride.
- the triethylamine salt of isethionic acid was previously obtained by reaction of ethylene oxide with triethylamine bisulfite in an aqueous reaction mixture and recovery of the resulting triethylarnine salt of isethionic acid.
- Example 3 Preparation of cyclohexylamine salt of xsulfo-x-butyl laarate
- the procedure described above in Example 1 was substantially repeated using as starting materials approximately stoichiometric quantities of the cyclohexylamine salt of x-hydroxy-x-butanesulfonic acid and lauroyl chloride.
- the cyclohexylamine salt of the hydroxybutanesulfonic acid was obtained by reaction of butylene-oxide and cyclohexylaminebisulfite in aqueous solution.
- butylene oxide was a mixture of the isomeric normal butylene oxides (approximately 94 percent 1,2-butylene oxide and 6 percent 2,3-butylene oxide) and gave rise to a mixture of the corresponding isomeric vicinalhydroxybutanesulfonic acids as cyclohexylamine salts.
- This salt mixture was recovered and reacted with lauroyl chloride to produce a quantitative yield of the cyclohexylamine salts of the isomeric vic-sulfobutyl laurates as a syrup whose solubility characterististics are shown in Table 1.
- the procedure described in Example 1 was substanstantially repeated using as starting materials approximately stoichiometric quantities of the tirethylamine salt of isethionic acid (preparation described in Example 2) and stearoyl chloride.
- the triethylamine salt of 2-sulfoethyl stearate was obtained as a pale yellow wax in approximately quantitative yield. Its solubility characteristics are shown in Table 1.
- the triethylamine salt of 2-sulfoethyl palmitate is prepared by heating a mixture of triethylamine salt of isethionic acid and palmitoyl chloride under reduced pressure until the evolution of hydrogen chloride is complete.
- Example 6. Preparati0n of benzylamine salt of xsulfo-x-propyl laurate
- the procedure described in Example 1 was substantially repeated using as starting materials approximately stoichiometric quantities of lauroyl chloride and a mixture of the benzylamine salts of l-hydroxy-Z-propanesulfonic acid and Z-hydroxy-l-propanesulfonic acid obtained by reaction of propylene oxide on an aqueous solution of benzylamine bisulfite.
- the resulting reaction product was a soap-like solid in approximately quantitative yield. Itssolubility characteristics are shown in Table 1.
- the new fatty acid esters of hydroxyalkanesulfonic acid amine salts are surface-active agents, advantageously useful as, or in the preparation of, liquid detergents, laundry preparations, textile scrubbing aids, and the like.
- the surface active properties of some of these fatty acid esters of hydroxyalkanesulfonic acid amine salts are set forth in Table 2. All of these tests were carried out on solutions in de-ionized water containing 0.1 percent by weight of the test materials.
- Example 7 To clean water having a hardness of 150 ;p.p.m. are added 0.75 gram of sodium 'tripolyphosphate and 0.4 gram of the cyclohexylamine salt of x-sulfo-x-butyl iaurate (from Example 3) per liter of water. The 'water solution is maintained at 120 F., and standard soiled cotton cloth is agitated therein with washing machine action for TABLE 2 Foam Height, mm. Inter- Test From 1. Wetting facial No. Material Example time, Tension,
- the Wetting Time shown in Table 2 was determined by the procedure described by C. Z. Draves and R. G. Clarkson in American Dyestuif Reporter, 20, pp. 201-208 (1931), modified by employing a nine-inch length of fabric tape (Synthron tape made by U.S. Testing Service, Inc., Hoboken, New Jersey), a one-gram hook, and a forty-gram weight.
- the Interfacial Tension values were measured with the duNouy Interfacial Tensiometer on the interface between the test aqueous solution and a refined mineral oil (see J. C. Harris, Detergency Evaluation and Testing, published 1954 by Interscience Publishers, Inc., New York).
- the amine salts are considerably more soluble in water than are the alkali metal, e.g. sodium, salts of the fatty acid esters of hydroxyalkancsulfonic acids. This water solubility permits the preparation of aqueous liquid compositions that are highly concentrated in the fatty acid esters of hydroxyalkanesulfonic acid amine salts.
- the amine salts are quite soluble in nonaqueous polar liquids such as alcohol and in non-polar liquids such as benzene, toluene and the like, as shown in Table 3.
- the alkali metal e.g. sodium salts of these fatty acid esters of hydroxyalkanesulfonic acids are almost insoluble in such non-polar liquids and are only slightly soluble in non-aqueous polar liquids.
- Example 8 A two percent by weight solution of the benzylamine salt of x-sulfo-x-propyl laurate (from Example 6) in toluene is found to be an effective detergent for cleaning accumulated dirt and grease from used machine parts.
- a method of making fatty acid esters of hydroxyalkanesulfonic acid amine salts which comprises mixing approximately stoichiometric amounts of a fatty acid halide having from eight to twenty carbon atoms and a vic-hydroxyalkanesulfonic acid amine salt wherein the vic-hydroxyalkanesulfonic acid has from two to four carbon atoms and the amine has from one to twenty carbon atoms, by adding the fatty acid halide to the vic-hydroxyalkanesulfonic acid amine salt incrementally as required by the ensuing esterification reaction and heating the resulting mixture at temperatures of from 70 to C. under an absolute pressure not greater than 200 mm. of mercury while removing the evolved hydrogen halide as formed from the reaction mixture.
- fatty acid halide is the acyl chloride of coconut oil fatty acids.
- a method according to claim 1 wherein the fatty acid halide is capryloyl chloride.
- amine salt is the triethanolamine salt of isethionic acid.
- amine salt is the triethylamine salt of isethionic acid.
- amine salt is the cyclohexylamine salt of a vic-hydroxybutanesulfonic acid.
- amine salt is the cyclohexylamine salt of a vic-hydroxpropanesulfonic acid.
- amine salt is the benzylamine salt of a vic-hydroxypropanesulfonic acid.
- fatty acid halide is the acyl chloride of coconut oil fatty acids and the amine salt is'the triethanolamine salt of isethionic acid.
- a method according to claim 1 wherein the fatty acid halide is lauroyl chloride and the amine salt is the cyclohexylamine salt. of a vic-hydroxybutanesulfonic acid.
- a method according to claim 1 wherein the fatty acid halide is oleoyl chloride and the amine salt is the cyclohexylamine salt of a vic-hydroxypropanesulfonic acid.
- the fatty acid halide is lauroyl chloride and the amine salt is the benzylamine salt of a vic-hydroxypropanesulfonic acid.
Description
FATTY ACID ESTERS OF HY DROXYALKANESUL- FONIC ACID AMINE SALTS Arthur R. Sexton and Edgar C. Britten, Midland, Mich, assignors to The Dow Chemical Company, Midland, M1ch., a corporation of Delaware No Drawing. Filed Mar. 3, 1958, Ser. No. 718,412
17 Claims. (Cl. 260-401) This invention relates to new compositions of matter and particularly to fatty acid esters of vic-hydroxyalkanesulfonic acid amine salts representable by the conventional formula wherein the group RCO corresponds to an aliphatic carboxylic acid RCO H having from eight to twenty carbon atoms, the symbol R' represents a vicinal bivalent alkylene radical having from two to four carbon atoms, and the symbol HAm represents an ammonium cation corresponding to a primary, secondary, or tertiary amine having alkyl, cycloalkyl, aralkyl, hydroxyalkyl, or aminoalkyl substitutents in which the total number of carbon atoms is from one to twenty.
Examples of the new fatty acid esters of hydroxyalkanesulfonic acid amine salts include ones which are esters of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid, ones wherein the alkylene radical corresponds to the ethylene, propylene, and butylene radicals, and ones in which the sulfonic acid salt is that of methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, monoethanolamine, diethanolamine, triethanolamine, the isopropanolamines, cyclohexylamine, dicyclohexylamine, benzylamine, and ethylenediamine.
Specific examples of such fatty acid esters of hydroxyalkanesulfonic. acid amine salts and their conventional formulae are as follows:
Triethylamine salt of 2-sulfoethyl caprylate:
Those skilled in the art will be able to perceive other specific examples of fatty acid esters of hydroxyalkanesulfonic acid amine salts from the disclosure in the preceding paragraph of specific carboxylic acids, specificalkylene radicals corresponding to the hydroxyalkanesultonic acids, and specific amines. Mixtures of fatty acid esters of hydroxyalkanesulfonic acid amine salts are also contemplated, for example, the mixtures correspondingto represents an olefin oxide such as ethylene oxide, 1,2- propylene. oxide, 1,2-butylene oxide, 2,3-butylene oxide, or isobutylene oxide and wherein HSO HAm represents States Patent mixed fatty acids, mixed hydroxyalkanesulfonic acids, and or mixed amines.
While the alkali metal, e.g. sodium, salts of some fatty acid esters of hydroxyalkanesulfonic acids are already known, the present amine salts of fatty acid esters of hydroxyalkanesulfonic acids are new and advantageous over the alkali metal salts.
The new fatty acid esters of hydroxyalkanesulfonic acid amine salts can be prepared by esterification reaction between a fatty acid halide such as a fatty acid chloride and a vic-hydroxyalkanesulfonic acid amine salt, such reaction being representable by the equation:
wherein the symbol X represents a halogen such as chlorine or bromine and the other symbols have meanings hereinbefore given, provided the reaction is carried out in the manner fully set forth below.
The vichydroxyalkarresulfonic acid amine salts employed as starting material in this reaction can be obtained by interaction of an alkylene epoxide and an aqueous amine bisulfite in accordance with the equation:
0 wherein represents an olefin oxide such as ethylen oxide, 1,2-propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, or isobutylene oxide and wherein HSO HAm represents an amine bisulfite salt. This method of making amine salts of vic-hydroxyalkanesulfonic acids is fully set forth in copending application of Arthur R. Sexton, Serial No. 670,381, filed July 8, 1957, and comprises mixing and reacting an olefin oxide with an amine bisulfite salt in an aqueous medium having a pH value of not less than 4 until the bisulfite salt is substantially consumed. The amine salts can also be made by stoichiometric reaction of the basic amine and a vic-hydroxyalkanesulfonic acid.
Itis contemplated that mixed vic-hydroxyalkanesulfonic acid amine salts be prepared from mixtures of olefin oxides and/or from mixtures of amines and that such mixed vic-hydroxyalkanesulfonic acid amine salts be subsequently reacted with a fatty acid halide or mixture of fatty acid halides. The term hydroxyalkanesulfonic acid is used herein to mean a vic-hydroxyalkanesulfonic acid.
The preparation of the new fatty esters of hydroxyalkanesulfonic acid amine salts by reaction of a fatty acid halide with a hydroxyalkanesulfonic acid amine salt' is preferably carried out by heating a mixture of the fatty acid halide and the hydroxyalkanesulfonic acid amine salt starting materials at a temperature of from 70 to C. under a reduced pressure of not more than 200 mm. of mercury, absolute pressure, preferably while subjecting the reaction mixture to mechanical working, while removing the evolved hydrogen halide from the reaction zone as swiftly and thoroughly as possible.
The starting materials are employed in amounts corresponding to an equivalent or slight excess of the amine salt of the hydroxyalkanesulfonic acid relative to the fatty acid halide in order to insure complete consumption of the'latter. Usually, the fatty acid halide is added to the hydroxyalkanesulfonic acid salt under reaction conditions at rates corresponding to the rate of consumption of the acyl halide by the ester-forming reaction.
When a substantially theoretical amount of hydrogen halide has been evolved from the reaction mixture, the reactionis regarded as complete, and the resulting product is essentially the fatty acid ester of the hydroxyalkanesulfonic acid amine salt.
It is noteworthy that these results have not been obtained when these starting materials, i.e. a fatty acid halide and a hydroxyalkanesulfonic acid amine salt, are heated together at atmospheric pressure; under such conditions, an amine hydrochloride is produced and the desired fatty acid ester of the hydroxyalkanesulfonic acid amine salt is not obtained.
Since the reaction product as described above is essentially the fatty acid ester of the hydroxyalkanesulfonic acid amine salt, it can be used as such for many purposes. If necessary or desirable, it can be further purified by crystallization and/or extraction with selective solvents.
The new fatty acid esters of hydroxyalkanesulfonic acid amine salts are advantageously useful as, and in the preparation of, liquid detergents, textile scrubbing aids, surfactants, and wetting agents in aqueous and nonaqueous compositions. When used as laundry detergents, the new fatty acid esters of hydroxyalkanesulfonic acid amine salts are less irritating to the skin and less injurious to delicate fabrics than are the harsh alkali detergents.
The following examples illustrate the invention but are not to be construed as limiting its scope.
Example 1.-Preparation of triethanolamine salt of 2- sulfoethyl ester of coconut oil fatty acids A charge of 534 grams of the triethanolamine salt of isethionic acid was placed in a sigma-blade mixer. The salt was previously obtained by reaction of ethylene oxide on triethanolamine bisulfite salt in water solution and recovery of the resulting triethanolamine salt of isethionic acid. The salt was heated to temperatures in the range of from 110 to 115 C. under 200 mm. of mercury, absolute pressure, while 410 grams of the acyl chlorides corresponding to the fatty acids of coconut oil was added dropwise over a period of 0.5 hour. Heating was continued for an additional hours while the pressure was progressively reduced to 20 mm. of mercury absolute. During these operations, the reaction mass was intensively mixed and kneaded while hydrogen chloride was evolved and was withdrawn from the reaction zone to a caustic trap until an amount of hydrogen chloride theoretically corresponding to the acyl chloride charged had been collected. The resulting reaction product was cooled and removed from the mixer-reactor as a thick paste. The triethanolamine salt of 2-sulfoethyl ester of coconut oil fatty acids thereby produced amounted to 880 grams. Its solubility properties are shown in Table 1.
Example 2.Preparatin of triethylamine salt of 2- salfoethyl caprylate The procedure described above in Example 1 was substantially repeated using as starting materials approximately stoichiometric quantities of the triethylamine salt of isethionic acid and capryloyl chloride. The triethylamine salt of isethionic acid was previously obtained by reaction of ethylene oxide with triethylamine bisulfite in an aqueous reaction mixture and recovery of the resulting triethylarnine salt of isethionic acid.
The resulting triethylamine salt of 2-sulfoethyl caprylate was a thick syrup, yield about 95 percent of theoretical. Its solubility characteristics are shown in Table 1.
Example 3.-Preparation of cyclohexylamine salt of xsulfo-x-butyl laarate The procedure described above in Example 1 was substantially repeated using as starting materials approximately stoichiometric quantities of the cyclohexylamine salt of x-hydroxy-x-butanesulfonic acid and lauroyl chloride. The cyclohexylamine salt of the hydroxybutanesulfonic acid was obtained by reaction of butylene-oxide and cyclohexylaminebisulfite in aqueous solution. The
butylene oxide was a mixture of the isomeric normal butylene oxides (approximately 94 percent 1,2-butylene oxide and 6 percent 2,3-butylene oxide) and gave rise to a mixture of the corresponding isomeric vicinalhydroxybutanesulfonic acids as cyclohexylamine salts. This salt mixture was recovered and reacted with lauroyl chloride to produce a quantitative yield of the cyclohexylamine salts of the isomeric vic-sulfobutyl laurates as a syrup whose solubility characterististics are shown in Table 1.
Example 4.-Preparazion of cyclohexylamine salt of x-' sulfo-x-propyl oleate Example 5.Preparation of triethylamine salt of 2- salfoethyl stearate The procedure described in Example 1 was substanstantially repeated using as starting materials approximately stoichiometric quantities of the tirethylamine salt of isethionic acid (preparation described in Example 2) and stearoyl chloride. The triethylamine salt of 2-sulfoethyl stearate was obtained as a pale yellow wax in approximately quantitative yield. Its solubility characteristics are shown in Table 1.
In like manner, the triethylamine salt of 2-sulfoethyl palmitate is prepared by heating a mixture of triethylamine salt of isethionic acid and palmitoyl chloride under reduced pressure until the evolution of hydrogen chloride is complete.
Example 6.-Preparati0n of benzylamine salt of xsulfo-x-propyl laurate The procedure described in Example 1 was substantially repeated using as starting materials approximately stoichiometric quantities of lauroyl chloride and a mixture of the benzylamine salts of l-hydroxy-Z-propanesulfonic acid and Z-hydroxy-l-propanesulfonic acid obtained by reaction of propylene oxide on an aqueous solution of benzylamine bisulfite. The resulting reaction product was a soap-like solid in approximately quantitative yield. Itssolubility characteristics are shown in Table 1.
In similar manner, other fatty acid esters of hydroxyalkanesulfonic acid amine salts can be made by employing other of the fatty acid halides and other vicinal hydroxyalkane-sulfonic acid amine salt as hereinbefore described. i
TABLE 1.SOLUBILITY CHARACTERISTICS OF FATTY ACID ESTERS OF HYDROXYALKANESULFONIO ACID AMINE SALT PRODUCTS OF THE EXAMPLES petroleum ether. .4
.5 The new fatty acid esters of hydroxyalkanesulfonic acid amine salts are surface-active agents, advantageously useful as, or in the preparation of, liquid detergents, laundry preparations, textile scrubbing aids, and the like. The surface active properties of some of these fatty acid esters of hydroxyalkanesulfonic acid amine salts are set forth in Table 2. All of these tests were carried out on solutions in de-ionized water containing 0.1 percent by weight of the test materials.
6 Example 7 To clean water having a hardness of 150 ;p.p.m. are added 0.75 gram of sodium 'tripolyphosphate and 0.4 gram of the cyclohexylamine salt of x-sulfo-x-butyl iaurate (from Example 3) per liter of water. The 'water solution is maintained at 120 F., and standard soiled cotton cloth is agitated therein with washing machine action for TABLE 2 Foam Height, mm. Inter- Test From 1. Wetting facial No. Material Example time, Tension,
1 No.- Instant After Minutes dynesl Minutes cm.
1 2-sulfoethyl stearate, triethylamine salt 5 20 2. 4 9. 2 2 :r-sulfo-propyl laurate, benzylamine salt. 6 180 180 0. 13 3. 8 3 x-sulio-r-butyl laurate, cyclohexylamine sal 3 179 179 0.10 4. 0 4 :t-sulfo z-propyl ole-ate, cyclohexylamine salt 4 132 132 0. 43 i. 4 5 2-sulioethyl laurate, sodium salt 82 82 0. 18 12. 1 6 2sulfoethy1 ester of coconut oil fatty acids,
sodium salt 117 117 0. 39 6. 9 7 z-sulfo-x propyi laurate, sodium salt 60 48 0. 08 10.0
For purposes of contrast with the new amine salts, data are also shown in Table 2 for several sodium salts of fatty acid esters of hydroxyalkanesulfonic acids.
The data reported in Table 2 under the heading Foam Height were obtained on test solutions containing 0.1 percent by weight of the test compounds by means of the procedure described by J. Ross and G. D. Miles in Oil and Soap, 18, pp. 99-102 (1941), modified by using 100 m1. of the test solution at the bottom of the column.
The Wetting Time shown in Table 2 was determined by the procedure described by C. Z. Draves and R. G. Clarkson in American Dyestuif Reporter, 20, pp. 201-208 (1931), modified by employing a nine-inch length of fabric tape (Synthron tape made by U.S. Testing Service, Inc., Hoboken, New Jersey), a one-gram hook, and a forty-gram weight.
The Interfacial Tension values were measured with the duNouy Interfacial Tensiometer on the interface between the test aqueous solution and a refined mineral oil (see J. C. Harris, Detergency Evaluation and Testing, published 1954 by Interscience Publishers, Inc., New York).
From the data in Table 2, it can readily be seen that the fatty acid esters of hydroxyalkanesulfonic acid amine salts have the properties of excellent surfactants.
The amine salts are considerably more soluble in water than are the alkali metal, e.g. sodium, salts of the fatty acid esters of hydroxyalkancsulfonic acids. This water solubility permits the preparation of aqueous liquid compositions that are highly concentrated in the fatty acid esters of hydroxyalkanesulfonic acid amine salts.
Furthermore, the amine salts are quite soluble in nonaqueous polar liquids such as alcohol and in non-polar liquids such as benzene, toluene and the like, as shown in Table 3. In contrast, the alkali metal, e.g. sodium salts of these fatty acid esters of hydroxyalkanesulfonic acids are almost insoluble in such non-polar liquids and are only slightly soluble in non-aqueous polar liquids.
ten minutes. After rinsing and drying, the cloth is found to be substantially clean of soil.
In place of the cyclohexylamine salt of x-sulfo-x-butyl laurate in this example there can be employed another of the fatty acid esters of hydroxyalkanesulfonic acid amine salts previously described herein with substantially the same results.
Example 8 A two percent by weight solution of the benzylamine salt of x-sulfo-x-propyl laurate (from Example 6) in toluene is found to be an effective detergent for cleaning accumulated dirt and grease from used machine parts.
That which is claimed is:
1. A method of making fatty acid esters of hydroxyalkanesulfonic acid amine salts which comprises mixing approximately stoichiometric amounts of a fatty acid halide having from eight to twenty carbon atoms and a vic-hydroxyalkanesulfonic acid amine salt wherein the vic-hydroxyalkanesulfonic acid has from two to four carbon atoms and the amine has from one to twenty carbon atoms, by adding the fatty acid halide to the vic-hydroxyalkanesulfonic acid amine salt incrementally as required by the ensuing esterification reaction and heating the resulting mixture at temperatures of from 70 to C. under an absolute pressure not greater than 200 mm. of mercury while removing the evolved hydrogen halide as formed from the reaction mixture.
2. A method according to claim 1 wherein the fatty acid halide is the acyl chloride of coconut oil fatty acids.
3. A method according to claim 1 wherein the fatty acid halide is capryloyl chloride.
4. A method according to claim 1 wherein the fatty acid halide is lauroyl chloride.
5. A method according to claim 1 wherein the fatty acid halide is oleoyl chloride.
6. A method according to claim 1 wherein the fatty acid halide is stearoyl chloride.
7. A method according to claim 1 wherein the amine salt is the triethanolamine salt of isethionic acid.
8. A method according to claim 1 wherein the amine salt is the triethylamine salt of isethionic acid.
9. A method according to claim 1 wherein the amine salt is the cyclohexylamine salt of a vic-hydroxybutanesulfonic acid.
10. A method according to claim 1 wherein the amine salt is the cyclohexylamine salt of a vic-hydroxpropanesulfonic acid.
11. A method according to claim 1 wherein the amine salt is the benzylamine salt of a vic-hydroxypropanesulfonic acid.
12. A method according to claim 1 wherein the fatty acid halide is the acyl chloride of coconut oil fatty acids and the amine salt is'the triethanolamine salt of isethionic acid.
13. A method according to claim 1 wherein the fatty acid halide is capryloyl chloride and the amine salt is the triethylamine salt of isethionic acid.
14. A method according to claim 1 wherein the fatty acid halide is lauroyl chloride and the amine salt is the cyclohexylamine salt. of a vic-hydroxybutanesulfonic acid.
15. A method according to claim 1 wherein the fatty acid halide is oleoyl chloride and the amine salt is the cyclohexylamine salt of a vic-hydroxypropanesulfonic acid.
16. A method according to claim 1 wherein the fatty 1.7. A method according to claim 1 wherein the fatty acid halide is lauroyl chloride and the amine salt is the benzylamine salt of a vic-hydroxypropanesulfonic acid.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Hoyt: German Chemical Developments in Synthetic Detergents and Wetting Agents, Hobart Publishing Comacid halide is stearoyl chloride and the amine salt is the 15 pany, Inc., Box 4127, Chevy Chase Branch, Washington triethylamine salt of isethionic acid.
15, D.C., page 15.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent N0. 2,968,664 January 17, 1961 Arthur R. Sexton et al.
It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 1, lines 70 to 72 strike out "represents an olefin oxide such as ethylene oxide, l,2propylene oxide l 2-butylene oxide, 2,3-butylene oxide, or isobutylene oxide and wherein HSO HAm represents"; column 2, line 32, for "ethylen" read ethylene column 3, line 40, for "hours" read hour column 4, line 32, for tirethylamine" read triethyl amine column 8 line 9, for "2,204,443 read 2,204,433
Signed and sealed this 7th day of November 1961.
(SEAL) Attest:
ERNEST W. SWIDER DAVID L. LADD Attesting Officer 7 Commissioner of Patents USCOMM-DC
Claims (1)
1. A METHOD OF MAKING FATTY ACID ESTERS OF HYDROXYALKANESULFONIC ACID AMINE SALTS WHICH COMPRISES MIXING APPROXIMATELY STOICHIOMETRIC AMOUNTS OF A FATTY ACID HALIDE HAVING FROM EIGHT TO TWENTY CARBON ATOMS AND A VIC-HYDROXYALKANESULFONIC ACID AMINE SALT WHEREIN THE VIC-HYDROXYALKANESULFONIC ACID HAS FROM TWO TO FOUR CARBON ATOMS AND THE AMINE HAS FROM ONE TO TWENTY CARBON ATOMS, BY ADDING THE FATTY ACID HALIDE TO THE VIC-HYDROXYALKANESULFONIC ACID AMINE SALT INCREMENTALLY AS REQUIRED BY THE ENSUING ESTERIFICATION REACTION AND HEATING THE RESULTING MIXTURE AT TEMPERATURES OF FROM 70* TO 135*C. UNDER AN ABSOLUTE PRESSURE NOT GREATER THAN 200 MM. OF MERCURY WHILE REMOVING THE EVOLVED HYDROGEN HALIDE AS FORMED FROM THE REACTION MIXTURE.
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Cited By (1)
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EP0581082A1 (en) * | 1992-07-22 | 1994-02-02 | Th. Goldschmidt AG | Process for the preparation of surface-active anion-cation complexes |
Citations (4)
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US2181890A (en) * | 1939-12-05 | Preparation of salts of interface | ||
US2204443A (en) * | 1938-10-06 | 1940-06-11 | Dohrman Mccoy | Valve spring tool |
US2687420A (en) * | 1951-01-08 | 1954-08-24 | Colgate Palmolive Co | Process for the neutralization of sulfonated products suitable as detergents |
US2861090A (en) * | 1954-10-05 | 1958-11-18 | Gen Aniline & Film Corp | Process of preparing beta-sulfoalkylesters of carboxylic acids |
-
1958
- 1958-03-03 US US718412A patent/US2968664A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2181890A (en) * | 1939-12-05 | Preparation of salts of interface | ||
US2204443A (en) * | 1938-10-06 | 1940-06-11 | Dohrman Mccoy | Valve spring tool |
US2687420A (en) * | 1951-01-08 | 1954-08-24 | Colgate Palmolive Co | Process for the neutralization of sulfonated products suitable as detergents |
US2861090A (en) * | 1954-10-05 | 1958-11-18 | Gen Aniline & Film Corp | Process of preparing beta-sulfoalkylesters of carboxylic acids |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0581082A1 (en) * | 1992-07-22 | 1994-02-02 | Th. Goldschmidt AG | Process for the preparation of surface-active anion-cation complexes |
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