US2126054A - Emulsifying agent and method of preparing same - Google Patents
Emulsifying agent and method of preparing same Download PDFInfo
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- US2126054A US2126054A US725086A US72508634A US2126054A US 2126054 A US2126054 A US 2126054A US 725086 A US725086 A US 725086A US 72508634 A US72508634 A US 72508634A US 2126054 A US2126054 A US 2126054A
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- oil
- alcohol amine
- soluble
- petroleum
- sulfonates
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- 238000000034 method Methods 0.000 title description 12
- 239000003995 emulsifying agent Substances 0.000 title description 10
- 239000000344 soap Substances 0.000 description 34
- -1 alcohol amine Chemical class 0.000 description 32
- 239000003921 oil Substances 0.000 description 29
- 150000003871 sulfonates Chemical class 0.000 description 26
- 239000003208 petroleum Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 19
- 230000001804 emulsifying effect Effects 0.000 description 16
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 13
- 150000003460 sulfonic acids Chemical class 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 229960004418 trolamine Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229940117013 triethanolamine oleate Drugs 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 125000005608 naphthenic acid group Chemical group 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- YNSYUYMBJSVIME-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;methanol Chemical compound OC.OCCNCCO YNSYUYMBJSVIME-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 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 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- C09K23/017—Mixtures of compounds
-
- 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
-
- 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*
-
- 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*
- Y10S516/91—The compound contains nitrogen, except if present solely as NH4+
Definitions
- This invention relates to a novel emulsifying agent and method of preparing same and the present application is a continuation in part of application Serial No. 372,529 filed June 20, 1929, now U. S. Patent 2,061,601 in which an emulsifying composition was disclosed which comprised essentially a mixture of an alcohol amine soap of oil-soluble sulfonic acids derived from petroleum with petroleum oil-soluble sulfonic acid com- 10 pound or salt thereof.
- composition claimed originally is a mixture of triethanolamine sulfonate soap with a sodium salt of oil-soluble sulfonic acid, the sulfonic radicals from both soaps being 15 obtained from the same fraction or different fractions of petroleum lubricatingoil stock such as i used in making the heavy mineral white oil marketed under the name Nujol.
- oil-soluble sulfonates increased the solubility of the alcohol amine soaps in oil and thereby improved the emulsifying capacity of said alcohol amine sulfonatea-
- the amount'of oilsoluble sulfonates to be used may vary'over fairly wide limits, such as from one-half to three parts of oil-soluble sulfonate to one part of alcohol amine soap, depending upon the purity of the soaps and the type of oil being used.
- oil-soluble sulfonates causes an unexpected improvement in emulsifying properties of the latter. It is recognized in the art that highly purified oil-soluble sulfonates may possess good emulsifying characteristics but that small amounts of impurities of various sorts, such as oily constituents, inorganic salts, etc. which may be present in crude oil-soluble sulfonates, prior .0 toany purification, may markedly decrease the emulsifying capacity of said oil-soluble sulfonates.
- One embodiment of the present invention is the addition of a small amount of alcohol amine soaps of petroleum sulfonic acids, oleic acid,
- the invention is not limited to the use of crude oilsoluble sulfonates because it has been found that even highly refined oil-soluble sulfonates having good emulsifying properties may be still further improved by the addition of small amounts of 55 alcohol amine soaps.
- the ethanolamine is obtainable on the market in the form of a glycerine-lik'e viscous liquid and usually consists of a mixture of mono-, di-, and' triethanolamine. Other alcoholamines may be used in this process such as, for instance, propanolamines, etc.
- the neutralization is carried out by adding the amine to the oil in small quantities at a time until the oil shows a slightly alkaamine is added. The oil is then allowed to settle,
- the amount of alcohol amine necessary for the neutralization depends on the nature of the amine employed, and the percentage of sulfonic acids present in the acid oil, and may vary within wide limits. However, this amount can be easily deter- 40 mined in each case since it is necessaryy to determine only the point when the reaction of the oil becomes alkaline.
- Alcohol amines may also be used for the neutralization of the water-soluble sulfonic acids of r the sludge mentioned above.
- the procedure is analogous to the neutralization of the acid oils as just described.
- sulfonic acid soaps of the alcohol amines are good emulsifying agents for oil-in-water type emulsions, but these soaps are relatively expensive and, therefore, cannot be used to a great extent commercially by themselves.
- small amounts of these alcohol amine soaps are added to oil-soluble sulfonate soaps which are relatively much cheaper, in order to increase the emulsifying properties of the latter. For example, about 10% of ethanolamine sulfonates such as prepared above is added to a batch of oil-soluble sulfonates having relatively poor emulsifying characteristics (whether the poor quality is due to the presence of impurities or due to the nature of the petroleum stock from which it was made).
- the oil-soluble sulfonates used may be prepared according to any of the well known methods and they may be used either in a cheaper crude form or in a purified form. Generally, oil is treated with sulfuric acid and the resulting acid sludge is removed, then the remaining acid oil is neutralized with soda and the resulting sulfonates are extracted from the oil by an aqueous alcoholic solution from which the sulfonates, in more or less crude form, are obtained by evaporation.
- One particular method of preparing purified oil-soluble sulfonates comprises isolating them directly from the aqueous alcoholic solution by agitating the latter with alkali carbonates, drawing off and filtering the upper layer and evaporating the filtrate to dryness.
- oil-soluble sulfonates In preparing these oil-soluble sulfonates, one may use either alkalies such as caustic soda or potash or alkaline earth hydroxides, such as lime or magnesia, or various other bases.
- alkalies such as caustic soda or potash or alkaline earth hydroxides, such as lime or magnesia, or various other bases.
- alkaline earth hydroxides such as lime or magnesia
- iron and manganese sulfonates may be used.
- the alcohol amine sulfonate soaps may be prepared by simple admixture of an alcohol amine with sulfonic acids reconstituted from the sodium or other salts thereof, as by treatment with sulfuric acid.
- the alcohol amine sulfonate soaps may be prepared either from oilsoluble sulfonic acids or from water-soluble sulfonic acids extracted, according to known methods, from the acid sludge resulting from the treatment of petroleum stocks with strong sulfuric acid.
- the alcohol amine soaps may be prepared by the use of other types of acids such as oleic acid, stearic acid, naphthenic acids, benzoic acid, etc.
- alcohol amine is intended to be included the mono-, di-, or trialkylol or arylol amines such as diethanolamine, monomethanol diethanolamine, dimethyl monomethanolamine, diphenylamine, etc. Also higher molecular weight amines containing about 5 to 20 carbon atoms or so, such as may be prepared from chlorhydrins of olefines or cracked wax, or from ehlor fatty hydroxy acids, etc., may be used.
- a new composition comprising a major proportion of oil-soluble sulfonates derived from petroleum and a minor proportion of alcohol amine soap.
- oil-soluble sulfonates are salts of a metal of the group consisting of alkalies, alkaline earths; iron and manganese.
- An emulsifying agent comprising a major proportion of oil-soluble sulfonate derived from petroleum and approximately 0.5 to 20% of an alcohol amine soap of a relatively high molecular weight organic acid.
- An emulsifying agent comprising a major proportion of oil-soluble sulfonates derived from petroleum and a minor proportion of an alcohol amine sulfonate derived from petroleum.
- An emulsifying agent comprising a major proportion of oil-soluble sulfonate derived from petroleum and a minor proportion of triethanolamine sulfonate.
- An emulsifying agent comprising a major proportion of crude oil-soluble sulfonates derived from petroleum and a small amount of an alcohol amine soap.
- An emulsifying agent comprising a major proportion of purified oil-soluble sulfonates derived from petroleum and a small amount of an alcohol amine soap adapted to improve the emulsifying characteristics of the composition.
- An emulsifiable composition comprising a major quantity of an oil of the group consisting of animal, vegetable, mineral lubricating oils and mineral white oils, a minor proportion of an oilsoluble sulfonate soap derived from petroleum and a small amount of an alcohol amine soap adapted to increase the emulsifying properties of the oil-soluble sulfonate soap.
- the method of improving the emulsifying properties of oil-soluble sulfonates derived from petroleum which comprises adding thereto a small amount of an alcohol amine soap derived by neutralizing an acid-treated petroleum oil with an alcohol amine.
- composition having valuable emulsifying properties which comprises adding 0.5-6! parts of an alcohol amine soap, derived by neutralizing an acidtreated petroleum-oil with an alcohol amine, to an amount of oil-soluble sulfonates, derived from petroleum, suflicient to make a total of 100 parts of the composition, whereby the emulsifying capacity of the composition is superior to that of 10 100 parts of either component taken separately.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Aug. 9, 1938 UNITED STATES PATENT OFFICE EMULSIFYING AGENT AND METHOD OF PREPARING SAME ware No Drawing. Application May 11, 1934, Serial No. 725,086
12 Claims.
This invention relates to a novel emulsifying agent and method of preparing same and the present application is a continuation in part of application Serial No. 372,529 filed June 20, 1929, now U. S. Patent 2,061,601 in which an emulsifying composition was disclosed which comprised essentially a mixture of an alcohol amine soap of oil-soluble sulfonic acids derived from petroleum with petroleum oil-soluble sulfonic acid com- 10 pound or salt thereof.
An example of the composition claimed originally is a mixture of triethanolamine sulfonate soap with a sodium salt of oil-soluble sulfonic acid, the sulfonic radicals from both soaps being 15 obtained from the same fraction or different fractions of petroleum lubricatingoil stock such as i used in making the heavy mineral white oil marketed under the name Nujol. In the original application it was pointed out specifically that the admixture of oil-soluble sulfonates increased the solubility of the alcohol amine soaps in oil and thereby improved the emulsifying capacity of said alcohol amine sulfonatea- The amount'of oilsoluble sulfonates to be used may vary'over fairly wide limits, such as from one-half to three parts of oil-soluble sulfonate to one part of alcohol amine soap, depending upon the purity of the soaps and the type of oil being used.
It has also been discovered and is theprimary feature of the present invention that the addition of relatively small amounts of alcohol amine soaps to oil-soluble sulfonates causes an unexpected improvement in emulsifying properties of the latter. It is recognized in the art that highly purified oil-soluble sulfonates may possess good emulsifying characteristics but that small amounts of impurities of various sorts, such as oily constituents, inorganic salts, etc. which may be present in crude oil-soluble sulfonates, prior .0 toany purification, may markedly decrease the emulsifying capacity of said oil-soluble sulfonates.
One embodiment of the present invention is the addition of a small amount of alcohol amine soaps of petroleum sulfonic acids, oleic acid,
5 stearic acid, naphthenic acids, etc. to relatively crude oil-soluble sulfonates having poor emulsifying characteristics. in order to impart good emulsifying properties thereto. However, the invention is not limited to the use of crude oilsoluble sulfonates because it has been found that even highly refined oil-soluble sulfonates having good emulsifying properties may be still further improved by the addition of small amounts of 55 alcohol amine soaps.
The invention will be fully understood from the following description:
It is an old practice in the refining of oils to treat the oil with strong sulfuric acid. Such treatment is usual in the refining of lubricating oils, in the preparation of the so-called white oils, etc. The strong sulfuric acid causes sulfonation of certain hydrocarbons. These sulfonic acids derived from petroleum are partly soluble in the oil, partly insoluble. The former remain 1 dissolved in the petroleum oil while the latter are found in the sludge. The acid oil containing oilsoluble sulfonic acids is then neutralized with ethanolamine or with some other alcohol amine as claimed in the parent application referred to. The ethanolamine is obtainable on the market in the form of a glycerine-lik'e viscous liquid and usually consists of a mixture of mono-, di-, and' triethanolamine. Other alcoholamines may be used in this process such as, for instance, propanolamines, etc. The neutralization is carried out by adding the amine to the oil in small quantities at a time until the oil shows a slightly alkaamine is added. The oil is then allowed to settle,
preferably over night. The bulk of the ethanol.- amine soaps formed-with the sulfonic acids separates out and the rest may be washed out with water or with some organic solvent such as isopropyl alcohol, etc.
The amount of alcohol amine necessary for the neutralization depends on the nature of the amine employed, and the percentage of sulfonic acids present in the acid oil, and may vary within wide limits. However, this amount can be easily deter- 40 mined in each case since it is necesary to determine only the point when the reaction of the oil becomes alkaline.
Alcohol amines may also be used for the neutralization of the water-soluble sulfonic acids of r the sludge mentioned above. The procedure is analogous to the neutralization of the acid oils as just described.
The structural formula of the triethanolamine sulfonic acid soap is probably the following:
they are obtained from an oil of about 225-250 Saybolt viscosity at 100 F., or they may be like a thick syrupy liquid when obtained from an oil of 80-100 viscosity. The color of these soaps depends on the degree of purification of the oil previous to precipitating out of the sulfonic acids in form of the soaps, and it may vary from light amber to dark red.
These sulfonic acid soaps of the alcohol amines are good emulsifying agents for oil-in-water type emulsions, but these soaps are relatively expensive and, therefore, cannot be used to a great extent commercially by themselves. However, according to the present invention, small amounts of these alcohol amine soaps are added to oil-soluble sulfonate soaps which are relatively much cheaper, in order to increase the emulsifying properties of the latter. For example, about 10% of ethanolamine sulfonates such as prepared above is added to a batch of oil-soluble sulfonates having relatively poor emulsifying characteristics (whether the poor quality is due to the presence of impurities or due to the nature of the petroleum stock from which it was made). Mixtures of a major proportion, i. e. over 50%, of oil-soluble sulfonate soaps and a minor proportion, 1. e. less than 50%, of alcohol amine soaps of relatively high molecular weight organic acids may be used, though preferably the mixtures are ones containing from 0.5% to 20.0% of an alcohol amine soap. When added to Nujol,
which is a commercial white oil, the latter formed an emulsion on shaking with water. Oil containing 1% or 2% of this mixture formed emulsions of the quick breaking type while an oil containing 4% or more of the mixture formed stable emulsions.
The oil-soluble sulfonates used may be prepared according to any of the well known methods and they may be used either in a cheaper crude form or in a purified form. Generally, oil is treated with sulfuric acid and the resulting acid sludge is removed, then the remaining acid oil is neutralized with soda and the resulting sulfonates are extracted from the oil by an aqueous alcoholic solution from which the sulfonates, in more or less crude form, are obtained by evaporation. One particular method of preparing purified oil-soluble sulfonates comprises isolating them directly from the aqueous alcoholic solution by agitating the latter with alkali carbonates, drawing off and filtering the upper layer and evaporating the filtrate to dryness. In preparing these oil-soluble sulfonates, one may use either alkalies such as caustic soda or potash or alkaline earth hydroxides, such as lime or magnesia, or various other bases. The iron and manganese sulfonates may be used.
Instead of preparing the alcohol amine sulfonate soaps as described hereinabove by direct neutralization of acid oil with an alcohol amine, they may be prepared by simple admixture of an alcohol amine with sulfonic acids reconstituted from the sodium or other salts thereof, as by treatment with sulfuric acid. The alcohol amine sulfonate soaps may be prepared either from oilsoluble sulfonic acids or from water-soluble sulfonic acids extracted, according to known methods, from the acid sludge resulting from the treatment of petroleum stocks with strong sulfuric acid. Also, the alcohol amine soaps may be prepared by the use of other types of acids such as oleic acid, stearic acid, naphthenic acids, benzoic acid, etc. By the term alcohol amine is intended to be included the mono-, di-, or trialkylol or arylol amines such as diethanolamine, monomethanol diethanolamine, dimethyl monomethanolamine, diphenylamine, etc. Also higher molecular weight amines containing about 5 to 20 carbon atoms or so, such as may be prepared from chlorhydrins of olefines or cracked wax, or from ehlor fatty hydroxy acids, etc., may be used.
An example of the use of an alcohol amine oleate is as follows:
To a sample of mineral white oil is added 7% of oil-soluble sulfonates (derived from a petroleum lubricating oil stock used for preparing Nujol, said sulfonates being purified by the particular method described hereinabove) and 1 /2% of triethanolamine oleate. This composition was found to be at least equivalent to a similar oil containing 14% of the same oil-soluble sulfonates but containing no triethanolamine oleate. In other words, 1 of triethanolamine oleate was at least equivalent to 7% of the oil-soluble sulfonate. and also the mixture was superior to either constituent alone. It is therefore, apparent that some new and unexpected results have been obtained.
It is not intended that the invention be limited by any of the examples given nor by any theories suggested for the operation of the invention but only by the appended claims in which it is intended to claim all novelty inherent in the invention as broadly as the prior art permits.
We claim:
1. A new composition comprising a major proportion of oil-soluble sulfonates derived from petroleum and a minor proportion of alcohol amine soap.
2. A composition according to claim 1, in which the oil-soluble sulfonates are salts of a metal of the group consisting of alkalies, alkaline earths; iron and manganese.
3. An emulsifying agent comprising a major proportion of oil-soluble sulfonate derived from petroleum and approximately 0.5 to 20% of an alcohol amine soap of a relatively high molecular weight organic acid.
4. An emulsifying agent comprising a major proportion of oil-soluble sulfonates derived from petroleum and a minor proportion of an alcohol amine sulfonate derived from petroleum.
5. An emulsifying agent comprising a major proportion of oil-soluble sulfonate derived from petroleum and a minor proportion of triethanolamine sulfonate.
6. An emulsifying agent comprising a major proportion of crude oil-soluble sulfonates derived from petroleum and a small amount of an alcohol amine soap.
7. An emulsifying agent comprising a major proportion of purified oil-soluble sulfonates derived from petroleum and a small amount of an alcohol amine soap adapted to improve the emulsifying characteristics of the composition.
8. An emulsifiable composition comprising a major quantity of an oil of the group consisting of animal, vegetable, mineral lubricating oils and mineral white oils, a minor proportion of an oilsoluble sulfonate soap derived from petroleum and a small amount of an alcohol amine soap adapted to increase the emulsifying properties of the oil-soluble sulfonate soap.
9. The method of improving the emulsifying properties of oil-soluble sulfonates derived from petroleum which comprises adding thereto a small amount of an alcohol amine soap derived by neutralizing an acid-treated petroleum oil with an alcohol amine.
10. The method of preparing a composition having valuable emulsifying properties which comprises adding 0.5-6! parts of an alcohol amine soap, derived by neutralizing an acidtreated petroleum-oil with an alcohol amine, to an amount of oil-soluble sulfonates, derived from petroleum, suflicient to make a total of 100 parts of the composition, whereby the emulsifying capacity of the composition is superior to that of 10 100 parts of either component taken separately.
11. The method of improving the emulsifying properties of an alcohol amine soap derived by neutralizing an acid-treated petroleum oil with an alcohol amine, which comprises adding onehalf to three parts of oil-soluble sulfonates derived from petroleum to one part of said soap. 12. An emulsion comprising essentially oil and water, and, in addition, a minor proportion of an emulsifying agent comprising a composition as defined in claim 1.
KARL T. STEIK.
STEWART C. FULTON.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US725086A US2126054A (en) | 1934-05-11 | 1934-05-11 | Emulsifying agent and method of preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US725086A US2126054A (en) | 1934-05-11 | 1934-05-11 | Emulsifying agent and method of preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2126054A true US2126054A (en) | 1938-08-09 |
Family
ID=24913103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US725086A Expired - Lifetime US2126054A (en) | 1934-05-11 | 1934-05-11 | Emulsifying agent and method of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2126054A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4645627A (en) * | 1982-06-12 | 1987-02-24 | Stamicarbon B.V. | Salts of acid ether sulphates and a process for the preparation of these salts |
-
1934
- 1934-05-11 US US725086A patent/US2126054A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4645627A (en) * | 1982-06-12 | 1987-02-24 | Stamicarbon B.V. | Salts of acid ether sulphates and a process for the preparation of these salts |
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