US2043476A - Cabboxylates of aliphatic alcohols - Google Patents
Cabboxylates of aliphatic alcohols Download PDFInfo
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- US2043476A US2043476A US2043476DA US2043476A US 2043476 A US2043476 A US 2043476A US 2043476D A US2043476D A US 2043476DA US 2043476 A US2043476 A US 2043476A
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- sulphonic
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- -1 aliphatic alcohols Chemical class 0.000 title description 16
- 239000002253 acid Substances 0.000 description 46
- 235000019441 ethanol Nutrition 0.000 description 34
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 150000007513 acids Chemical class 0.000 description 26
- 150000001298 alcohols Chemical class 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atoms Chemical group C* 0.000 description 16
- 150000001735 carboxylic acids Chemical class 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000009736 wetting Methods 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000010000 carbonizing Methods 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- 230000001476 alcoholic Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- GLYJVQDYLFAUFC-UHFFFAOYSA-N butyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCC GLYJVQDYLFAUFC-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 229920002955 Art silk Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- KAQHZJVQFBJKCK-UHFFFAOYSA-L Potassium pyrosulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OS([O-])(=O)=O KAQHZJVQFBJKCK-UHFFFAOYSA-L 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000005909 ethyl alcohol group Chemical group 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229940058172 ethylbenzene Drugs 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 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 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 230000000266 injurious Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 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 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M palmitate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- YGDMPMKCHSXJJF-UHFFFAOYSA-N pentyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCC YGDMPMKCHSXJJF-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000009991 scouring Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000005418 vegetable material Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
Classifications
-
- 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
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- 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
-
- 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
- Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
- Y10S516/909—The agent contains organic compound containing sulfoxy*
Definitions
- PATENT OFFICE oannoxrm'res or AIJPHATIO anconons wrrn NoN-Anom'nc sunrnomc can- BOXYLIC ACIDS Fritz Guenther, Johannes Conrad, and Karl Saftien, Ludwigshafen-on-tli e-Bhine,.
- the present invention relates to the production of assistants for the textile and allied industries.
- esters of carboxylic acids are obtained when the said acids are boiled for long periods of time under a reflux condenser with a quantity of alcohols exceeding that-required for esterification. It is preferable to add inorganic acids, other acid-reacting catalysts or agents removing water such as gaseous hydrochloric acid, or concentrated sulphuric or phosphoric acids, potassium pyrosulphate, or aromatic sulphonic acids.
- Sulphonic acids of carboxylicacids especially only be esterified in an unsatisfactory manner.
- additions of acid catalysts or agents removing water are injurious because they often cause decompositions during the reaction which may impair the value of the reaction products for industrial employment.
- alphasulphonic carboxylic acids cannot be converted in the desired manner by the usual methods, or can onlybe converted with difliculty and inconvenience.
- aliphatic open chain or cycloaliphatic alcohols or aliphatic alcohols in which-a hydrogen atom connected to a carbon atom is substituted by an aromatic nucleus such as open chain aliphatic mono-hydric alcohols, as for example'methyl, ethyl, propyl, butyl, iso-butyl, amyl, hexyl, octyl or dodecyl alcohols, or glycols, or mono-ethers of the latter, cyclohexanol or its homologues or benzyl alcohol, on an acid sulphonic carboxylic acid substance, i. e. on the said sulphonic-carboxylic acids in the free state or acid salts thereof.
- open chain aliphatic mono-hydric alcohols as for example'methyl, ethyl, propyl, butyl, iso-butyl, amyl, hexyl, octyl or dodecyl alcohols,
- esters naphthenic sulphonic acid and the like or the free acids are suitable for the formation of the esters (carboxylates).
- Acid salts of substituted sulphonic acids containing carboxyl groups as for example those containing halogen or, hydroxy groups, such as bromo-stearic sulphonic acids or hydroxy stearic sulphonic acid, obtainable by the sulphonation of oleic acid and like acids, or the acids in the free state, may also be employed.
- aliphatic open chain or cycloaliphatic alpha sulphonic carboxylic acids or their acid salts since they furnish particularly valuable products. 1
- esteriflcatio'n proceeds smoothly by heating the components to elevated temperatures preferably above up to 250 0., generally between and C. if acid salts be employed, those of the non-aromatic series, frequently can.
- esters obtainable in the said manner when employing alpha-sulphonlc-carboxylic acid substances are, contrasted withthe acid salts employed as initial materials, generally very readily soluble in water and organic solvents such as lower alcohols (from methyl to amyl alcohols), ethers or ketones, anhydrous acetic acid, benzine or benzene, if the alcohols and sulphonic-carboxylic acids employed in the esterification do not contain more than eight carbon atoms, whereas those prepared from alcohols containing more than eight carbon atoms are less readily soluble in water but still readily soluble in organic solvents.
- organic solvents such as lower alcohols (from methyl to amyl alcohols), ethers or ketones, anhydrous acetic acid, benzine or benzene
- aqueous solutions of all such reaction products have a high wetting, cleansing and dispersing power and do not give water-insoluble salts with the quantities of the substances forming the hardness in water usually occurring in hard water. They may therefore be employed with great advantage for example for all purposes in the treatment of fibrous materials such as wool, cotton, silk or artificial silk, as for example in wetting, carbonizing, washing or scouring or agent or for softening inthetreatmentotthesaidmaterials with emulsions or suspensions as for example in oiling, impresnating .or' finishing, and in dyeing.
- fibrous materials such as wool, cotton, silk or artificial silk
- wetting, carbonizing, washing or scouring or agent or for softening inthetreatmentotthesaidmaterials with emulsions or suspensions as for example in oiling, impresnating .or' finishing, and in dyeing.
- esters it alpha-sulpho-carboxylic acidshave the capacity of imparting a soft touch and great flexibility to fibrous materials in a high degree.
- Example 1 i 100 parts. of the monosodium salt of palmitic sulphonic acid are heated to about'180' C.'in a pressure-tight vessel with 300 parts of methyl alcohol while stin'ing. After the reaction is com-- pleted the remainders of methyl alcohol are distilled oil. The crude methyl ester obtained may be pulverized after cooling and may be directly employed without 1 er purification as wetting textile materials. II desired the reaction may also be carried out at about 150 C. with -a smaller quantity of methyl alcohol and without stirring.
- the ethyl. isopropyl, butyl, isobutyl, amyl and like esters or palmitic sulphonic acid may be prepared in the same manner.
- octyl alcohol such as octyl alcohol, benzyl alcohol, glycerine, cyclohexanol. alcohols oi. wool fat and the like.
- Example 3 10 0 parts of the mono-sodium salt of hydroxy- 'stearic sulphonic acid are heated to 160 C. with 200 parts of methyl alcohol in a pressure-tight vessel until esteriflcation has taken place.
- the resulting carboxylic acid ester dissolves readily in water and dilute sulphuric acid and has, even in acid baths, an excellent wetting power, so that it may be employed with special advantage as an addition to carbonizing baths.
- the ester obtained (methyl palmitate ID110111- ic acid) can be further P i by re-dissolution in ethyl ether, ethyl alcohol or benzene and is easily soluble in cold water.
- the aqueous solution of the ester possesses a high wetting, foaming arid dispersing power andthe ester is not the'compounds
- Example 5 100 parts of the mono-sodium salt of di-bromostearic sulphonic acid are heated in a pressure-' tight vessel while stirring for hours at 140 C. with 300 parts of methanol. The reaction product isthen worked up as described in Example l.
- Example 6 2 grams of butyl palmitate sulphonic acid are dissolved in 1 litre oi an aqueous sulphuric acid solution of 4 B. strength. Woolen piece goods are soaked with; the liquid solution, squeezed oil.
- Carboxylates of aliphatic alcohols with allphatic alpha-sulphonic carboxylic acids contain-- ing at least 8 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented June 9, 1936 PATENT OFFICE oannoxrm'res or AIJPHATIO anconons wrrn NoN-Anom'nc sunrnomc can- BOXYLIC ACIDS Fritz Guenther, Johannes Conrad, and Karl Saftien, Ludwigshafen-on-tli e-Bhine,.
assignors to I. G. Farbenindustrie Aktiengesellschaft, Frankfort-on-the-Main, Germany No Drawing. Application August 1'], 1931, Serial No. 557,740. In Germany September 1, 1930 The present invention relates to the production of assistants for the textile and allied industries.
It is already known that esters of carboxylic acids are obtained when the said acids are boiled for long periods of time under a reflux condenser with a quantity of alcohols exceeding that-required for esterification. It is preferable to add inorganic acids, other acid-reacting catalysts or agents removing water such as gaseous hydrochloric acid, or concentrated sulphuric or phosphoric acids, potassium pyrosulphate, or aromatic sulphonic acids. It has already been proposed to carry out esterifications in the presence of solvents, as for example benzene whereby the 4 solvent together with the water formed by the conversions-re distilled off slowly during the reaction, the equilibrium of the 'es'teriflcation thus being displaced so as to favour the formation of esters.
Sulphonic acids of carboxylicacids, especially only be esterified in an unsatisfactory manner. In particular, additions of acid catalysts or agents removing water are injurious because they often cause decompositions during the reaction which may impair the value of the reaction products for industrial employment. Especially the alphasulphonic carboxylic acidscannot be converted in the desired manner by the usual methods, or can onlybe converted with difliculty and inconvenience.
We have now found that the esteriflcation of non-aromatic sulphonic-carboxylic acids containing at least 8 carbon atoms, especially of alpha-sulphonic-carbowlic acids, is carried out in a manner whichis extremelysimple industrially by acting with aliphatic alcohols, i. e. aliphatic open chain or cycloaliphatic alcohols or aliphatic alcohols in which-a hydrogen atom connected to a carbon atom is substituted by an aromatic nucleus, such as open chain aliphatic mono-hydric alcohols, as for example'methyl, ethyl, propyl, butyl, iso-butyl, amyl, hexyl, octyl or dodecyl alcohols, or glycols, or mono-ethers of the latter, cyclohexanol or its homologues or benzyl alcohol, on an acid sulphonic carboxylic acid substance, i. e. on the said sulphonic-carboxylic acids in the free state or acid salts thereof. In this way products are obtained which are entirely free from troublesome by-products and decomposition products, the working up of which oflers no difllculty at all. Generally speaking the acid salts of all sulphonic-carboxylic acids containing at least 8 carbon atoms as for example 8 Claims. (01. zsoaos) the sulphonic acids of carboxylic acids, oils, fats or waxes of vegetal i. e. vegetable and animal, origin, such as palmitic sulphonic acids or stearic sulphonic acids or lauric sulphonic acid,
naphthenic sulphonic acid and the like or the free acids are suitable for the formation of the esters (carboxylates). Acid salts of substituted sulphonic acids containing carboxyl groups, as for example those containing halogen or, hydroxy groups, such as bromo-stearic sulphonic acids or hydroxy stearic sulphonic acid, obtainable by the sulphonation of oleic acid and like acids, or the acids in the free state, may also be employed. Generally we prefer aliphatic open chain or cycloaliphatic alpha sulphonic carboxylic acids or their acid salts since they furnish particularly valuable products. 1
The esteriflcatio'n proceeds smoothly by heating the components to elevated temperatures preferably above up to 250 0., generally between and C. if acid salts be employed, those of the non-aromatic series, frequently can.
andbetween 50 and 100 C. if free sulphonic carboxylic acids be used. when employing alcoholic components of 10W boiling point, such as methyl or ethyl alcohols, the reaction can be accelerated by working in pressure-tight vessels at temperatures above the normal boiling point of the alcohols. In order'to produce as complete an esterification of the acid components as possible it is generally speaking preferable to employ 'a quantity of alcoholic component exceeding that required for esterlflcation. v
The esters obtainable in the said manner when employing alpha-sulphonlc-carboxylic acid substances are, contrasted withthe acid salts employed as initial materials, generally very readily soluble in water and organic solvents such as lower alcohols (from methyl to amyl alcohols), ethers or ketones, anhydrous acetic acid, benzine or benzene, if the alcohols and sulphonic-carboxylic acids employed in the esterification do not contain more than eight carbon atoms, whereas those prepared from alcohols containing more than eight carbon atoms are less readily soluble in water but still readily soluble in organic solvents. The aqueous solutions of all such reaction products have a high wetting, cleansing and dispersing power and do not give water-insoluble salts with the quantities of the substances forming the hardness in water usually occurring in hard water. They may therefore be employed with great advantage for example for all purposes in the treatment of fibrous materials such as wool, cotton, silk or artificial silk, as for example in wetting, carbonizing, washing or scouring or agent or for softening inthetreatmentotthesaidmaterials with emulsions or suspensions as for example in oiling, impresnating .or' finishing, and in dyeing. The
esters it alpha-sulpho-carboxylic acidshave the capacity of imparting a soft touch and great flexibility to fibrous materials in a high degree.
The following examples will further illustrate the nature of this invention but the invention is not restricted to these examples. The parts'are by weight. V
, Example 1 i 100 parts. of the monosodium salt of palmitic sulphonic acid are heated to about'180' C.'in a pressure-tight vessel with 300 parts of methyl alcohol while stin'ing. After the reaction is com-- pleted the remainders of methyl alcohol are distilled oil. The crude methyl ester obtained may be pulverized after cooling and may be directly employed without 1 er purification as wetting textile materials. II desired the reaction may also be carried out at about 150 C. with -a smaller quantity of methyl alcohol and without stirring.
The ethyl. isopropyl, butyl, isobutyl, amyl and like esters or palmitic sulphonic acid may be prepared in the same manner.
. Example 2 100 parts of the mono-sodium salt of stearic sulphonic acid are boiled under a reflux cn= denser with 100 parts of ethylene glycol until.
' esteriflcation has taken place. The reaction mixture is worked up as described in Examplelr The esterification may be carried out, in the same mannerrwith other alcohols 01 high boiling point,
such as octyl alcohol, benzyl alcohol, glycerine, cyclohexanol. alcohols oi. wool fat and the like.
Laurie sulphonic acid may be employed instead oi stearic sulphonic acid.
' Example 3 10 0 parts of the mono-sodium salt of hydroxy- 'stearic sulphonic acid are heated to 160 C. with 200 parts of methyl alcohol in a pressure-tight vessel until esteriflcation has taken place.
The resulting carboxylic acid ester dissolves readily in water and dilute sulphuric acid and has, even in acid baths, an excellent wetting power, so that it may be employed with special advantage as an addition to carbonizing baths.
Example 4 100 parts of crude palmitic sulphonic acid,
are dissolved in 250 parts of methanol, whereupon the'mixture is refluxed for about 5 hours. The hot solution is then filtered, rendered neutral with the aid of aqueous caustic soda solution and v precipitated from the solution by forming the hardness of water.
the remainders oi methanol are distilled oii whereupon the residue is dried in vacuo.
The ester obtained (methyl palmitate ID110111- ic acid) can be further P i by re-dissolution in ethyl ether, ethyl alcohol or benzene and is easily soluble in cold water. ,The aqueous solution of the ester possesses a high wetting, foaming arid dispersing power andthe ester is not the'compounds Example 5 100 parts of the mono-sodium salt of di-bromostearic sulphonic acid are heated in a pressure-' tight vessel while stirring for hours at 140 C. with 300 parts of methanol. The reaction product isthen worked up as described in Example l.
Example 6 2 grams of butyl palmitate sulphonic acid are dissolved in 1 litre oi an aqueous sulphuric acid solution of 4 B. strength. Woolen piece goods are soaked with; the liquid solution, squeezed oil.
and carbonized by heating for 1 hour at from 80 to 90" C. The goods are then rinsed in the f usual manner and washed with alkali. A uniform carbonization is attained, the goods being completely freed from vegetable material. In the place of the butyl palmitate sulphonic acid the same quantity or amyl palmitate sulphonic acid may be employed as well as a sulphuric acidsolutlon of 2? B. strength. The same or even better results are obtained with a carbonizing liquor containing per litre of an aqueous sulphuric acid solution of 4 Be. strength one gram of iiobutyl palmitate sulphonic acid.
What we claim is:
1. Carboxylates of aliphatic alcohols with allphatic alpha-sulphonic carboxylic acids contain-- ing at least 8 carbon atoms.
'2. Carboxylates of aliphatic alcohols containing from 1 to 12 carbon atoms'with aliphatic alpha-sulphonic carboxylic acids containing at least 8 carbon atoms.
3. Carboiwlates of methyl alcohol with non- 7. An ethylene glycol mono-carboxylate of a palmltic sulphonic acid.
8. A methyl carboxylate of a hydroxy-stearlc sulphonic acid.
FRI'IZ GUEN'I'HER.
JOHANNES CONRAD. KARL SAFI'IEN.
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US2043476A true US2043476A (en) | 1936-06-09 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2460968A (en) * | 1943-09-28 | 1949-02-08 | Innovations Chimiques Sinnova | Method for the obtainment of aliphatic sulfonic acids and esters thereof |
US3128294A (en) * | 1961-06-09 | 1964-04-07 | Alexander J Stirton | Salts of alpha-sulfonated fatty acid esters |
US3219584A (en) * | 1961-06-09 | 1965-11-23 | Alexander J Stirton | Wetting agents and surface active compositions therefrom |
US3413221A (en) * | 1961-03-01 | 1968-11-26 | Henkel & Compagnie G M B H | Wash agents |
EP1286656A1 (en) * | 2000-05-19 | 2003-03-05 | Huish Detergents, Inc. | Detergent containing alpha-sulfofatty acid esters and methods of making and using the same |
-
0
- US US2043476D patent/US2043476A/en not_active Expired - Lifetime
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2460968A (en) * | 1943-09-28 | 1949-02-08 | Innovations Chimiques Sinnova | Method for the obtainment of aliphatic sulfonic acids and esters thereof |
US3413221A (en) * | 1961-03-01 | 1968-11-26 | Henkel & Compagnie G M B H | Wash agents |
US3128294A (en) * | 1961-06-09 | 1964-04-07 | Alexander J Stirton | Salts of alpha-sulfonated fatty acid esters |
US3219584A (en) * | 1961-06-09 | 1965-11-23 | Alexander J Stirton | Wetting agents and surface active compositions therefrom |
EP1286656A1 (en) * | 2000-05-19 | 2003-03-05 | Huish Detergents, Inc. | Detergent containing alpha-sulfofatty acid esters and methods of making and using the same |
EP1286656A4 (en) * | 2000-05-19 | 2006-02-01 | Huish Detergents Inc | Detergent containing alpha-sulfofatty acid esters and methods of making and using the same |
US7772176B2 (en) | 2000-05-19 | 2010-08-10 | The Sun Products Corporation | Detergent compositions containing α-sulfofatty acid esters and methods of making and using the same |
US20100267605A1 (en) * | 2000-05-19 | 2010-10-21 | The Sun Products Corporation | Detergent Containing Alpha-Sulfofatty Acid Esters and Methods of Making and Using the Same |
EP2258818A1 (en) * | 2000-05-19 | 2010-12-08 | The Sun Products Corporation | Method of making detergent compositions comprising alpha-sulfofatty acid esters |
US8030264B2 (en) | 2000-05-19 | 2011-10-04 | The Sun Products Corporation | Detergent containing α-sulfofatty acid esters and methods of making and using the same |
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