US2683736A - Amine salts of the tridecyl esters of sulfobenzoic acid - Google Patents
Amine salts of the tridecyl esters of sulfobenzoic acid Download PDFInfo
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- US2683736A US2683736A US310567A US31056752A US2683736A US 2683736 A US2683736 A US 2683736A US 310567 A US310567 A US 310567A US 31056752 A US31056752 A US 31056752A US 2683736 A US2683736 A US 2683736A
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- Prior art keywords
- salts
- tridecyl
- sulfobenzoic acid
- carbon atoms
- amine salts
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- -1 Amine salts Chemical class 0.000 title description 29
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 title description 13
- 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 title description 3
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 5
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 230000006315 carbonylation Effects 0.000 description 5
- 238000005810 carbonylation reaction Methods 0.000 description 5
- 125000005270 trialkylamine group Chemical group 0.000 description 5
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HGKLFYLYWZXWPO-UHFFFAOYSA-N sulfo benzoate Chemical compound OS(=O)(=O)OC(=O)C1=CC=CC=C1 HGKLFYLYWZXWPO-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003941 n-butylamines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009967 tasteless effect Effects 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- NWPCFCBFUXXJIE-UHFFFAOYSA-N 2-(hydroxymethylamino)ethanol Chemical compound OCCNCO NWPCFCBFUXXJIE-UHFFFAOYSA-N 0.000 description 1
- LWRWNEOSFSMCAL-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylbutan-2-yl)butan-2-amine Chemical class CCC(C)(C)N(C(C)(C)CC)C(C)(C)CC LWRWNEOSFSMCAL-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical class NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000005332 diethylamines Chemical class 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 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 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical class CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 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 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/58—Carboxylic acid groups or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/04—Sulfonates or sulfuric acid ester salts derived from polyhydric alcohols or amino alcohols or derivatives thereof
-
- 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
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- the present invention relates to surface-active agents and is particularly concerned with alkylamine or alkanolamine salts of tridecyl sulfobenzoates as new compounds possessing a high degree of utility as wetting-out and lathering agents.
- surface-active agents find wide application in a large number of industrial processes, especially in those relating to the treatment of textiles and other fibrous materials.
- compounds heretofore suggested for these and related purposes are the esters of sulfobenzoic acid and aliphatic alcohols containing from 812 or 18 carbon atoms, for example, the octyl, dodecyl, or oleyl sodium sulfobenzoate as illustrated in U. S. Patents 2,359,291 and 2,423,972.
- the present sulfobenzoates are obtainable by neutralizing with an alkylamine or an alkanolamine, the acid ester obtained by condensing 2-, 3- or 4-sulfobenzoic acid or an acid halide thereof with an alcohol fraction derived by the carbonylation and hydrogenation (Oxo) reaction of "the olefins triisobutylene and tetrapropylene.
- the alcohol fraction which forms the starting material for my present esters may be defined as having the structure ROI-I, wherein R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of triisobutylene or tetrapropylene or mixtures thereof.
- the present sulfobenzoates may be represented by the following structure has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino groups in the molecule and from 2 to 3 carbon atoms in the alkylene chain.
- salts of tridecyl 2-, 3- or 4-su1fobenzoate having the above formula and provided by the present invention may be mentioned monoalkylamine salts such as the ethylamine, n-butylamine, 2-ethylhexylamine, n-decylamine and tert-dodecylamine salts; the dialkylamine salts such as the dimethylamine, diisopropylamine.
- the trialkylamine salts such as the trimethylamine, tri-n-butylamine, and tri-tert-amylamine salts
- the mono-alkanolamine salts such as the ethanolamine and the 4-hydroxybutylamine salts
- the di-alkanolamine salts such as the diisopropanolamine, dimethanolamine, and methanolethanolamine
- the tri-alkanolamine salts such as the triethanolamine and tri-n-propanolamine salts
- the alkylene or polyalkylene polyamine salts such as the ethylenediamine, triethylenetetramine, dipropylenetriamine, and diethylenetriamine salts, and morpholine.
- R is as defined above and in which Z is selected from the class consisting of mono-, diand trialkylamines in which the alkyl radical contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radical V 2-ethylhexylamine to pH 7.25 VI diethylamine to pH 6.9 VII diethylenetriamine to pH 7.8
- the resulting neutralized ethanol solutions were dried with stirring under reduced pressure (15-20 3 mm.) at a maximum pot temperature of 40-45 C.
- the dried. products comprised the respective amine salts of tridecyl sulfobenzoate. Testing of the surface activity of the dried salts thus obtained gave the following values:
- R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of an olefin selected from the class consisting of triisobutylene and tetrapropylene and mixtures of the same and in which Z is selected from the class consisting of mono-, diand trialkylamines in which the alkyl radicals contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radi cal has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino groups in the molecule and from 2 to 3 carbon atoms in the alkylene chain, and morpholine.
- R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of an olefin selected from the class consisting of triisobutylene, tetrapropylene, and mixtures thereof with an amine compound selected from the class consisting of mono-, diand trialkylamines in which the alkyl radical contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radical has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino groups in the molecule and from 2 to 3 carbon atoms in the alkylene chain and morpholine, and recovering from the resulting reaction product salts having the formula COOR SOaELZ in which R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of an olefin selected from the class consisting of triisobuty
Description
Patented July 13, 1954 AMINE SALTS OF THE TRIDECYL ESTER/S OF SULFOBENZOIC ACID Milton Kosmin, Dayton, Ohio, assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application September 19, 1952, Serial No. 310,567
12 Claims. 1
The present invention relates to surface-active agents and is particularly concerned with alkylamine or alkanolamine salts of tridecyl sulfobenzoates as new compounds possessing a high degree of utility as wetting-out and lathering agents.
As is known, surface-active agents find wide application in a large number of industrial processes, especially in those relating to the treatment of textiles and other fibrous materials. Among the compounds heretofore suggested for these and related purposes are the esters of sulfobenzoic acid and aliphatic alcohols containing from 812 or 18 carbon atoms, for example, the octyl, dodecyl, or oleyl sodium sulfobenzoate as illustrated in U. S. Patents 2,359,291 and 2,423,972. I have now found, as a result of comparative tests, that the heretofore unknown alkylamine or alkanolamine salts of the esters of sulfobenzoic acids and a certain mixture of isomeric tridecyl alcohols are of outstanding value, not only for the purpose of assisting in the wetting of textile materials, but also from a lathering standpoint. They are particularly valuable as tasteless foaming agents in dentifrice formulations, in edible oils adapted for use in mayonnaise preparation, and as tasteless wetting agents in the manufacture of food extracts, e. g., in soluble coiTee extraction, etc. The present sulfobenzoates are obtainable by neutralizing with an alkylamine or an alkanolamine, the acid ester obtained by condensing 2-, 3- or 4-sulfobenzoic acid or an acid halide thereof with an alcohol fraction derived by the carbonylation and hydrogenation (Oxo) reaction of "the olefins triisobutylene and tetrapropylene. The alcohol fraction which forms the starting material for my present esters may be defined as having the structure ROI-I, wherein R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of triisobutylene or tetrapropylene or mixtures thereof.
The present sulfobenzoates may be represented by the following structure has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino groups in the molecule and from 2 to 3 carbon atoms in the alkylene chain. As examples of salts of tridecyl 2-, 3- or 4-su1fobenzoate having the above formula and provided by the present invention may be mentioned monoalkylamine salts such as the ethylamine, n-butylamine, 2-ethylhexylamine, n-decylamine and tert-dodecylamine salts; the dialkylamine salts such as the dimethylamine, diisopropylamine. din-octylamine and the methylethylamine salts; the trialkylamine salts such as the trimethylamine, tri-n-butylamine, and tri-tert-amylamine salts; the mono-alkanolamine salts such as the ethanolamine and the 4-hydroxybutylamine salts, the di-alkanolamine salts, such as the diisopropanolamine, dimethanolamine, and methanolethanolamine; the tri-alkanolamine salts such as the triethanolamine and tri-n-propanolamine salts; the alkylene or polyalkylene polyamine salts such as the ethylenediamine, triethylenetetramine, dipropylenetriamine, and diethylenetriamine salts, and morpholine.
The invention is further illustrated, but not limited, by the following example:
EXAMPLE Into a reaction vessel equipped with mechanical stirrer, thermometer, and drying tube there was placed 310.5 g. (1.5 mole) of an isomeric mix ture of tridecyl alcohols boiling within the range of 252.8 C.-2'73.9 C. and obtained by the Oxo process from a polymeric olefin of 12 carbon atoms, carbon monoxide and hydrogen. m-Sulfobenzoic acid (303.0 g.) was heated to 150 C. and then poured into the tridecyl alcohol, whereupon the temperature of the reaction mixture rose to 90 C. The resulting mixture was stirred at a temperature of from 90-95 C, for 80 minutes and then allowed to cool. At this point the reaction mixture comprised the substantially pure tridecyl sulfobenzoic acid. It was divided into 100 g. portions and each portion was then neutralized to the pH shown below with an ethanol solution of one of the following amines:
000R I monoethanolamine to pH 8.1
II triethanolamine to pH 6.55 III N-butylamine to pH 8.5 SO3H.Z IV diisobutylamine to pH 7.1
in which R is as defined above and in which Z is selected from the class consisting of mono-, diand trialkylamines in which the alkyl radical contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radical V 2-ethylhexylamine to pH 7.25 VI diethylamine to pH 6.9 VII diethylenetriamine to pH 7.8
The resulting neutralized ethanol solutions were dried with stirring under reduced pressure (15-20 3 mm.) at a maximum pot temperature of 40-45 C. The dried. products comprised the respective amine salts of tridecyl sulfobenzoate. Testing of the surface activity of the dried salts thus obtained gave the following values:
Surface activity of tridecyl sulfobenzoate amine salts Surface Tension Interfacial Tension dynes/cm. a dynes/cm., at percent Concenpercent Concen- Amine Salt tration tration monoethanolamine 29. 7 30. 7 31. 3 2.4 4. 9 7. 4 triethanolamine 31. 6 27. 8 35. 4. 5 7. 5 10. 3 n-butylaniine 1 32. 7 32. 4 32.4 1. O O. 6 (l. 8 di-isobutylamine 37. 4 33. 7 39. 7 4. 6 6.0 10. 3 2-ethylhexylamine 1 32. 0 38.2 36. 6 1. 0 5. 3 8. 4 diethylamine. i 34. 3 37 6 40. 8 2. 3 3. 5 4. 6 diethylenetriamine 31. 3 32. 4 32. 4 l. O 1. 3 l3. 1
X For surface tension determination there were employed solutions in a liquid paraifinic hydrocarbon known to the trade as Nujol and having a surface tension of 38 dynes/cm. lnteriacial tension was determined against distilled water.
Salt Tested 0.5 0.25 0.125 0.0025 0.03 0.01
monoethanolamine. 3. 7 6. 2 14. 2 36. 8 75.0 180+ triethanolamine 3. 9 6. 2 15. 5 38. 8 180+ diethylainine 7.8 8. 6 17. 5 58. 7 75. 8 180+ The water-soluble monoethanolamine, triethanolamine and diethylamine salts of sulfobenzoic acid prepared as described above were tested for detergency by the method described by Jay C. Harris and Earl L. Brown in the Journal of the American Oil Chemists Society, vol. 27, p. 135-143 (1950). By the application of this method it is possible to evaluate the deterg-ency of a product in terms of any standard detergent. For convenience I have compared the detergency of the present and related products with the detergency of Gardinol WA, which is a commercial detergent produced by sulfating the alcohols derived by hydrogenation of coconut oil fatty acids. The following results were obtained for tests conducted in water of 50 p. p. m. hardness:
C ompound Tested D ggfg f monoethanolaminc 121 triethanolamine 107 diethylamine 113 Lather heights, cm.
Salt of Tridecyl Sull'obenzoate Tested At Once monoethanolamine 1 5. 0 14. 7 triethanolamine 14. 7 14. 5
What I claim is: 1. Surface-active agents having the formula COOR S O aELZ in which R, is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of an olefin selected from the class consisting of triisobutylene and tetrapropylene and mixtures of the same and in which Z is selected from the class consisting of mono-, diand trialkylamines in which the alkyl radicals contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radi cal has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino groups in the molecule and from 2 to 3 carbon atoms in the alkylene chain, and morpholine.
2. The monoethanolamine salt of the tridecyl ester of sulfobenzoic acid.
3. The triethanolamine salt of the tridecyl ester of sulfobenzoic acid.
4. The n-butylamine salt of the tridecyl ester of sulfobenzoic acid.
5. The 2-ethylhexylamine salt of the tridecyl ester of sulfobenzoic acid.
6. The diethylenetriamine salt of the tridecyl ester of sulfobenzoic acid.
'7. The process of preparing surface-active agents which comprises contacting a sulfobenzoate having the formula COOR SOaH
wherein R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of an olefin selected from the class consisting of triisobutylene, tetrapropylene, and mixtures thereof with an amine compound selected from the class consisting of mono-, diand trialkylamines in which the alkyl radical contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radical has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino groups in the molecule and from 2 to 3 carbon atoms in the alkylene chain and morpholine, and recovering from the resulting reaction product salts having the formula COOR SOaELZ in which R is a primary alkyl radical having an average of 13 carbon atoms derived from an alcohol formed by the carbonylation and hydrogenation of an olefin selected from the class consisting of triisobutylene, tetrapropylene and mixtures thereof and Z is selected from the class consisting of mono-, diand trialkylamines in which the alkyl radical contains from 1 to 12 carbon atoms, mono-, diand trialkanolamines in which the alkanol radical has from 1 to 4 carbon atoms and alkylenepolyamines and polyalkylenepolyamines having from 2 to 4 amino covering the n-butylamine salt of tridecyl sulfobenzoate from the resulting reaction product.
11. The process which comprises contacting tridecyl sulfobenzoate with 2-ethylhexylamine and recovering the Z-ethylhexylamine salt of trideoyl sulfobenzoate from the resulting reaction product.
12. The process which comprises contacting triclecyl sulfobenzoate with diethyienetriamine and recovering the diethylenetriamine salt of tridecyl sulfobenzoate from the resulting reaction product.
N 0 references cited.
Claims (1)
1. SURFACE-ACTIVE AGENTS HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US310567A US2683736A (en) | 1952-09-19 | 1952-09-19 | Amine salts of the tridecyl esters of sulfobenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US310567A US2683736A (en) | 1952-09-19 | 1952-09-19 | Amine salts of the tridecyl esters of sulfobenzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2683736A true US2683736A (en) | 1954-07-13 |
Family
ID=23203110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US310567A Expired - Lifetime US2683736A (en) | 1952-09-19 | 1952-09-19 | Amine salts of the tridecyl esters of sulfobenzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2683736A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3196113A (en) * | 1965-07-20 | Removal of flux from brazed aluminum assemblies | ||
| EP0261957A2 (en) * | 1986-09-24 | 1988-03-30 | Exxon Chemical Patents Inc. | Chemical compositions and use as fuel additives |
| JPS63165486A (en) * | 1986-09-24 | 1988-07-08 | エクソン ケミカル パテンツ インコーポレーテッド | Improved fuel additive |
| JPS63165487A (en) * | 1986-09-24 | 1988-07-08 | エクソン ケミカル パテンツ インコーポレーテッド | Intermediate fraction composition having small wax crystal size |
| EP0445844A2 (en) * | 1986-09-24 | 1991-09-11 | Exxon Chemical Patents Inc. | Distillate fuel |
| US5578091A (en) * | 1990-04-19 | 1996-11-26 | Exxon Chemical Patents Inc. | Chemical compositions and their use as fuel additives |
| US5814110A (en) * | 1986-09-24 | 1998-09-29 | Exxon Chemical Patents Inc. | Chemical compositions and use as fuel additives |
-
1952
- 1952-09-19 US US310567A patent/US2683736A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3196113A (en) * | 1965-07-20 | Removal of flux from brazed aluminum assemblies | ||
| EP0261957A2 (en) * | 1986-09-24 | 1988-03-30 | Exxon Chemical Patents Inc. | Chemical compositions and use as fuel additives |
| JPS63165486A (en) * | 1986-09-24 | 1988-07-08 | エクソン ケミカル パテンツ インコーポレーテッド | Improved fuel additive |
| JPS63165487A (en) * | 1986-09-24 | 1988-07-08 | エクソン ケミカル パテンツ インコーポレーテッド | Intermediate fraction composition having small wax crystal size |
| EP0261957A3 (en) * | 1986-09-24 | 1989-08-30 | Exxon Chemical Patents Inc. | Chemical compositions and use as fuel additives |
| EP0445844A2 (en) * | 1986-09-24 | 1991-09-11 | Exxon Chemical Patents Inc. | Distillate fuel |
| EP0445844A3 (en) * | 1986-09-24 | 1991-11-06 | Exxon Chemical Patents Inc. | Distillate fuel |
| JP2539848B2 (en) | 1986-09-24 | 1996-10-02 | エクソン ケミカル パテンツ インコーポレーテッド | Middle distillate composition with small wax crystal size |
| JP2539847B2 (en) | 1986-09-24 | 1996-10-02 | エクソン ケミカル パテンツ インコーポレーテッド | Improved fuel additive |
| US5814110A (en) * | 1986-09-24 | 1998-09-29 | Exxon Chemical Patents Inc. | Chemical compositions and use as fuel additives |
| US5578091A (en) * | 1990-04-19 | 1996-11-26 | Exxon Chemical Patents Inc. | Chemical compositions and their use as fuel additives |
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