US2121032A - Detergent and wetting agent and process of producing the same - Google Patents
Detergent and wetting agent and process of producing the same Download PDFInfo
- Publication number
- US2121032A US2121032A US70671A US7067136A US2121032A US 2121032 A US2121032 A US 2121032A US 70671 A US70671 A US 70671A US 7067136 A US7067136 A US 7067136A US 2121032 A US2121032 A US 2121032A
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- US
- United States
- Prior art keywords
- acid
- pseudopimaric
- detergent
- wetting agent
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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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
- C11D15/00—Manufacture of resin soap or soaps derived from naphthenic acids; Compositions
-
- 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
Definitions
- This invention relates to animproved detergent and wetting agent and process of producing the same.
- soaps for example, soaps, sulfonated castor oil, sulfated higher fatty alcohols, sulfonated higher fatty acids, etc.
- soaps suffer from the disadvantage of being precipitated from their aqueous solutions by the electrolytes in hard waters, particularly by waters carrying calcium compounds, and the sulfated alcohols of the higher fatty acids and the sulfonated higher fatty acids suffer from the disadvantage of high cost of the higher fatty alcohol used, so that their use in trade has been severely limited.
- the product in accordance with my invention possesses superior detergent and wetting powers, in comparison with many of those now used in various industries, as, for example, in the manufacture of soap, the textile and tanning indus tries, and many others, is economical to manufacture, requires no complicated separation and isolation of the material tobe sulfonated, and may be made by a very simple sulfonation process and apparatus.
- My product is not precipitated by calcium salts contained in hard waters, and is non-hydrolyzable by alkali or acid under practical conditions of use.
- my invention comprises the product of the sulfonation of pseudopimaric acid, for example, prepared in accordance with the process disclosed in application for United States Letters Patent; Serial No. 675,976, filed June 15, 1933, entitled A new rosin acid and process of producing the same, in accordance with which rosin oil having an appreciable resin acid content, say at least about five per cent, or a product obtained from rosin bysuitable heat treatment (with or without distillation), such as a rosin known in the trade as a heat-treated or partially distilled x rosin, is extracted with an aqueous solution of an alkali, which is preferably caustic soda or caustic potash, The extraction is carried out preferably by thoroughly mixing the raw material and the 45 alkaline solution in an appropriate manner, as by stirring or agitation, and is continued until practically complete saponification is accomplished.
- an alkali which is preferably caustic soda or caustic potash
- Thepseudopimaric acid so produced melts at about 69'71 C., while the partially purified pseudopimaric acid melts at about 169-181 C., has an optical angle of rotation (11):), of about +25 to +50", and when more fully refined melts at 195.5 to 198 C. (corrected), has an optical angle of rotation, (an), of about +0.33" and an elementary composition which corresponds approximately to the formula CzoHsoOz.
- pseudopimaric acid As the properties of the new acid are not identical with eitherthe abietic or the pimaric types of acids, it is called pseudopimaric acid.
- my invention comprises sulfonation by treatment by concentrated sulfuric acid of pseudopimaric acid or of mixtures containing pseudopimaric acid, such, for example, as result from suitable heat-treatment of wood and/or gum rosin, if desired in a suitable solvent attacked or unattacked by concentrated sulfuric acid, e. g. carbon tetrachloride, liquid sulfur dioxide, petroleum distillates, saturated and/or unsaturated hydrocarbons, preferably of' the aromatic and/or hydroaromatic series, although I may employ unsaturated aliphatic hydrocarbons, or mixtures thereof.
- concentrated sulfuric acid e. g. carbon tetrachloride, liquid sulfur dioxide, petroleum distillates, saturated and/or unsaturated hydrocarbons, preferably of' the aromatic and/or hydroaromatic series, although I may employ unsaturated aliphatic hydrocarbons, or mixtures thereof.
- sulfonating agent I preferably employ sulfuric acid of specific gravity about 1.84, although I may employ somewhat lower or somewhat higher strengths, even to fuming sulfuric acid, or chlorsulfonic acid or sulfur trioxide as the sulfonating agent.
- Example I As an example of the carrying out of my process, 50 parts by weight of partially refined pseudopimaric acid, M. P. l67169 C.,
- Example III As a further example of the carrying out of my process, 400 parts by weight of a finely pulverized product rich in pseudopimaric acid, and obtained by suitable destructive distillation of wood rosin and/or gum rosin without fractionation under reduced pressure, was treated as in- Example II, giving a 10% yield of a crystalline sulfonic acid M. P. 223-4" C. with decomposition.
- Example IV As a further example of the carrying out of my process in the presence of a suitable solvent, a
- My sulfonic acid product will be found variously adaptable to uses as an improved detergent and wetting out agent, e.- g. in the scouring of textiles,
- I may prepare the neutral or acid, alkali, or alkaline earth salts, or salts of organic bases, e. g. of ethanolamine of my sulfonic acid product and such are also variously adaptable to uses in an improved detergent and wetting out agent.
- organic bases e. g. of ethanolamine of my sulfonic acid product
- Method of preparation of a sulfonic acid comprising treating pseudopimaric acid with a sulfonating agent.
- Method of preparation of a sulfonic acid comprising treating pseudopimaric acid with sulfuric acid of a density about 1.84.
- R is the radical of the compound produced by a process which comprises treating pseudopimaric acid with a, sulfonating agent and extracting the product with hot water to produce a soluble sulfonic acid
- X is a. member of the group consisting of hydrogen, alkali metals, alkaline earth metals,
- n corresponds to the number of acid groups in .the molecule.
- Method of preparation of a sulfonic acid comprising treating pseudopimaric acid with fuming sulfuric acid.
- Method of preparation of a 'sulfonic acid comprising treating pseudopimaric acid with chlorosulfonic acid.
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
Patented June 1938 DETIiRGENT AND WETTING AGENT AND PROCESS OF PRODUCING THE SAME Torsten Hasselstrom, New York, N. Y., assignor to G. & A. Laboratories, Savannah, Ga., a. corpo ration of Georgia No Drawing.
. 6 Claims.
This invention relates to animproved detergent and wetting agent and process of producing the same.
Many detergents and wetting agents are 5 known, for example, soaps, sulfonated castor oil, sulfated higher fatty alcohols, sulfonated higher fatty acids, etc. Of these, soaps suffer from the disadvantage of being precipitated from their aqueous solutions by the electrolytes in hard waters, particularly by waters carrying calcium compounds, and the sulfated alcohols of the higher fatty acids and the sulfonated higher fatty acids suffer from the disadvantage of high cost of the higher fatty alcohol used, so that their use in trade has been severely limited.
The product in accordance with my invention possesses superior detergent and wetting powers, in comparison with many of those now used in various industries, as, for example, in the manufacture of soap, the textile and tanning indus tries, and many others, is economical to manufacture, requires no complicated separation and isolation of the material tobe sulfonated, and may be made by a very simple sulfonation process and apparatus. My product is not precipitated by calcium salts contained in hard waters, and is non-hydrolyzable by alkali or acid under practical conditions of use.
Broadly speaking, my invention comprises the product of the sulfonation of pseudopimaric acid, for example, prepared in accordance with the process disclosed in application for United States Letters Patent; Serial No. 675,976, filed June 15, 1933, entitled A new rosin acid and process of producing the same, in accordance with which rosin oil having an appreciable resin acid content, say at least about five per cent, or a product obtained from rosin bysuitable heat treatment (with or without distillation), such as a rosin known in the trade as a heat-treated or partially distilled x rosin, is extracted with an aqueous solution of an alkali, which is preferably caustic soda or caustic potash, The extraction is carried out preferably by thoroughly mixing the raw material and the 45 alkaline solution in an appropriate manner, as by stirring or agitation, and is continued until practically complete saponification is accomplished.
In order to break up any emulsion and to facilitate the separation of the mixture into two lay- 50 ers, some methanol or other suitable solvent is added just prior to the termination of the agitation. Upon standing, the mixture then separates into two layers, the upper consisting mainly of unsaponifiable material and the lower one con- 55 taining the alkali pseudopimarate inalkaline Application March 24, 1936, Serial No. 70,671
solution. This lower layer is then drawn off, acidified with a dilute mineral acid, such as hydrochloric acid or sulfuric acid, or by the addition of a suitable acid salt, such as nitre cake. This acidification precipitates the novel acid, called pseudopimaric acid, as a viscous, sticky mass, which is collected by agglomeration and then removed. It is then pressed to free it as much as possible from adhering mother liquor, and is washed thoroughly with water until substantially free from all water-soluble contaminants. The crude acid is then dried in any suitable way.
Thepseudopimaric acid so produced melts at about 69'71 C., while the partially purified pseudopimaric acid melts at about 169-181 C., has an optical angle of rotation (11):), of about +25 to +50", and when more fully refined melts at 195.5 to 198 C. (corrected), has an optical angle of rotation, (an), of about +0.33" and an elementary composition which corresponds approximately to the formula CzoHsoOz. As the properties of the new acid are not identical with eitherthe abietic or the pimaric types of acids, it is called pseudopimaric acid.
More specifically my invention comprises sulfonation by treatment by concentrated sulfuric acid of pseudopimaric acid or of mixtures containing pseudopimaric acid, such, for example, as result from suitable heat-treatment of wood and/or gum rosin, if desired in a suitable solvent attacked or unattacked by concentrated sulfuric acid, e. g. carbon tetrachloride, liquid sulfur dioxide, petroleum distillates, saturated and/or unsaturated hydrocarbons, preferably of' the aromatic and/or hydroaromatic series, although I may employ unsaturated aliphatic hydrocarbons, or mixtures thereof.
As sulfonating agent I preferably employ sulfuric acid of specific gravity about 1.84, although I may employ somewhat lower or somewhat higher strengths, even to fuming sulfuric acid, or chlorsulfonic acid or sulfur trioxide as the sulfonating agent.
Example I As an example of the carrying out of my process, 50 parts by weight of partially refined pseudopimaric acid, M. P. l67169 C.,
and 250 parts by weight of sulfuric acid sp. gr. 1.84 were mixed at about 5 to +5 C., stirred for about 20 minutes, then poured onto cracked ice. The brownish precipitate was filtered out, washed with cold water until the washings cloudseveral days, it separate ed when mixed with the original liquor, and the washed precipitate then extracted three times with boiling water, leaving a brownish, insoluble semi-solid resin. The hot aqueous extracts, on cooling, deposited crystalline sulfonic acid in a yield of-25.5 parts by weight, which, after revariation in-the yields of the sulfonic. acid.
- Example I! As a further example of the carrying out of my process, 1200 parts by weight of a ilnely pulverized product, rich in pseudopimaric acid, obtained by suitable destructive distillation of wood and/o gum rosin, followed by removal of abiete es, etc., by fractional distillation under reduced pressure were mixed with 2400 parts by weight of sulfuric acid sp. gr. 1.84, and the mixture agitated for a suitable time at 10-35 0.,
then treated as in-Example I. The crude product from this reaction was extracted twice with boiling water and allowed to stand to crystallize.
A sulfonic acid of lighter color than in Example I was obtained, M. P. 223-4 C. with decomposition, (a)}, =+62.63, yield 465 parts by weight, and also a dark noncrystalline sulfonic acid, whose sodium salt in aqueous solution behaved like a soap, of yield of 190 parts by weight.
Example III As a further example of the carrying out of my process, 400 parts by weight of a finely pulverized product rich in pseudopimaric acid, and obtained by suitable destructive distillation of wood rosin and/or gum rosin without fractionation under reduced pressure, was treated as in- Example II, giving a 10% yield of a crystalline sulfonic acid M. P. 223-4" C. with decomposition.
Example IV As a further example of the carrying out of my process in the presence of a suitable solvent, a
mixture of ioo pms of steam-distilled mm 011,
rich in pseudopimaric acid, and containing a total of up to about 70% of resin acids calculated. as CzoHaoOz, with 200 parts 'of concentrated sulfuric acid of a sp. gr. of about 1.84 was agitate'd for a suitable length of time at a temperature'of about 5 C. to about +50 0., and the crude sulfonation product so obtained worked up as in Example II. a
My sulfonic acid product will be found variously adaptable to uses as an improved detergent and wetting out agent, e.- g. in the scouring of textiles,
as a soap assistant, etc.
I may prepare the neutral or acid, alkali, or alkaline earth salts, or salts of organic bases, e. g. of ethanolamine of my sulfonic acid product and such are also variously adaptable to uses in an improved detergent and wetting out agent.
The brownish, insoluble semi-solid resin mateture of cup grease, solid oils, and the like.
What I claim and desire to protect by Letters Patent is:
1. Method of preparation of a sulfonic acid comprising treating pseudopimaric acid with a sulfonating agent.
2. Method of preparation of a sulfonic acid comprising treating pseudopimaric acid with sulfuric acid of a density about 1.84.
3. As a detergent and wetting agent, the sulfonic acid produced in accordance with claim 1.
4. As a detergentand wetting agent, compounds of the formula RG05, where R is the radical of the compound produced by a process which comprises treating pseudopimaric acid with a, sulfonating agent and extracting the product with hot water to produce a soluble sulfonic acid, X is a. member of the group consisting of hydrogen, alkali metals, alkaline earth metals,
and alltyiolamines, and n corresponds to the number of acid groups in .the molecule.
5. Method of preparation of a sulfonic acid comprising treating pseudopimaric acid with fuming sulfuric acid.
6. Method of preparation of a 'sulfonic acid comprising treating pseudopimaric acid with chlorosulfonic acid.
TORSTEN HASSELSTROM.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70671A US2121032A (en) | 1936-03-24 | 1936-03-24 | Detergent and wetting agent and process of producing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70671A US2121032A (en) | 1936-03-24 | 1936-03-24 | Detergent and wetting agent and process of producing the same |
Publications (1)
Publication Number | Publication Date |
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US2121032A true US2121032A (en) | 1938-06-21 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US70671A Expired - Lifetime US2121032A (en) | 1936-03-24 | 1936-03-24 | Detergent and wetting agent and process of producing the same |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5877814A (en) * | 1981-10-22 | 1983-05-11 | Tanabe Seiyaku Co Ltd | Antiulcer agent |
US4529602A (en) * | 1981-10-22 | 1985-07-16 | Tanabe Seiyaku Co., Ltd. | Method for treatment or prophylaxis of gastro-intestinal disease |
-
1936
- 1936-03-24 US US70671A patent/US2121032A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5877814A (en) * | 1981-10-22 | 1983-05-11 | Tanabe Seiyaku Co Ltd | Antiulcer agent |
US4529602A (en) * | 1981-10-22 | 1985-07-16 | Tanabe Seiyaku Co., Ltd. | Method for treatment or prophylaxis of gastro-intestinal disease |
JPS6323174B2 (en) * | 1981-10-22 | 1988-05-16 | Tanabe Seiyaku Co | |
JPS63165361A (en) * | 1981-10-22 | 1988-07-08 | Tanabe Seiyaku Co Ltd | Novel sulfodehydroabietate |
JPH0231070B2 (en) * | 1981-10-22 | 1990-07-11 | Tanabe Seiyaku Co |
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