US2741629A - Aluminum soap of iso-octoic acids - Google Patents
Aluminum soap of iso-octoic acids Download PDFInfo
- Publication number
- US2741629A US2741629A US321747A US32174752A US2741629A US 2741629 A US2741629 A US 2741629A US 321747 A US321747 A US 321747A US 32174752 A US32174752 A US 32174752A US 2741629 A US2741629 A US 2741629A
- Authority
- US
- United States
- Prior art keywords
- acids
- aluminum
- iso
- soap
- octoic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims description 37
- 239000000344 soap Substances 0.000 title claims description 32
- 150000007513 acids Chemical class 0.000 title claims description 23
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims description 18
- 229910052782 aluminium Inorganic materials 0.000 title claims description 18
- 239000000446 fuel Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- RKFMOTBTFHXWCM-UHFFFAOYSA-M [AlH2]O Chemical compound [AlH2]O RKFMOTBTFHXWCM-UHFFFAOYSA-M 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- -1 iso-octyl alcohols Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
Definitions
- This invention relates to aluminum soap of mixed isooctoic acids. More particularly, it relates to the aluminum di-acid soap of mixed iso-octoic acids. These soaps have a multitude of uses and have particularly good utility as thickening agents for liquid hydrocarbons. Thus, when these soaps are mixed with hydrocarbon fuels such as motor gasoline, they serve to produce the jellied gasoline used in flamethrowers and fire bombs.
- the mixed iso-octoic acids from which these soaps are made are obtained by the oxidation of iso-octyl alcohols, the latter in turn being produced from mixed heptenes by an oxo process reaction.
- the acids are largely 5, 6 and 7 carbon atoms in length with resulting 3, 2 and 1 methyl group substituents on the carbon chain respectively.
- the 6 and 7 carbon atom chains are usually present in the greater proportion.
- the aluminum di-acid soap is produced by reacting an aqueous sodium soap solution of the acid containing approximately 50% excess caustic, with an aqueous solution of an inorganic aluminum salt such as aluminum sulfate. The resulting insoluble hydroxy aluminum soap is filtered and washed free of by-product salts and dried.
- the dried granular soap when added to liquid hydrocarbons create visco-elastic gels, the consistencies of which will vary with the concentration of thickening agent employed.
- Example Dissolve 43 grams of C. P. sodium hydroxide in 850 ml. of water. Add 100 grams of mixed iso-octoic acids (neutral equivalent 143.5) and cool to room tempera ture by stirring. Slowly add 342 ml. of aluminum sulfate solution containing 137 grams of A12(SO4)318H2O, (iron free), in a fine stream with good agitation to precipitate the aluminum soap. The aluminum soap is filtered and washed free of sulfate ion as indicated by barium chloride test solution. The soap is first dried by exposure to room atmosphere on an open tray, and final drying is accomplished over phosphorous pentoxide in a desiccator.
- Equations The aluminum di-acid soap is precipitated in accordance with the following simplified equations.
- Some mono-acid soap may precipitate concurrently in accordance with the following equation:
- the process which comprises reacting a mixture of iso-octoic acids, comprising principally mono, diand tri-methyl substituted heptoic, hexoic and pentoic acids respectively, with approximately 50% excess sodium hydroxide, adding to the solution an excess of aluminum sulfate to precipitate aluminum mono and di-acid soaps of iso-octoic acids, washing the resulting insoluble hydroxy aluminum soap free of sulfate ion anddrying the aluminum soap.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
tates ALUMINUM SOAP OF ISO-OCTOIC ACIDS No Drawing. Application November 20, 1952, Serial No. 321,747
5 Claims. (Cl. 260-448) (Granted under Title 35, U. S. Code (1952), sec. 266) The invention described herein may be manufactured and used by or for the Government for governmental purposes, without the payment to me of any royalty thereon.
This invention relates to aluminum soap of mixed isooctoic acids. More particularly, it relates to the aluminum di-acid soap of mixed iso-octoic acids. These soaps have a multitude of uses and have particularly good utility as thickening agents for liquid hydrocarbons. Thus, when these soaps are mixed with hydrocarbon fuels such as motor gasoline, they serve to produce the jellied gasoline used in flamethrowers and fire bombs.
The mixed iso-octoic acids from which these soaps are made are obtained by the oxidation of iso-octyl alcohols, the latter in turn being produced from mixed heptenes by an oxo process reaction. The acids are largely 5, 6 and 7 carbon atoms in length with resulting 3, 2 and 1 methyl group substituents on the carbon chain respectively. The 6 and 7 carbon atom chains are usually present in the greater proportion.
A disclosure of the 0x0 process for preparing oxidation products from olefins appears in U. S. Patent 2,553,364.
The aluminum di-acid soap is produced by reacting an aqueous sodium soap solution of the acid containing approximately 50% excess caustic, with an aqueous solution of an inorganic aluminum salt such as aluminum sulfate. The resulting insoluble hydroxy aluminum soap is filtered and washed free of by-product salts and dried.
The dried granular soap when added to liquid hydrocarbons create visco-elastic gels, the consistencies of which will vary with the concentration of thickening agent employed.
Example Dissolve 43 grams of C. P. sodium hydroxide in 850 ml. of water. Add 100 grams of mixed iso-octoic acids (neutral equivalent=143.5) and cool to room tempera ture by stirring. Slowly add 342 ml. of aluminum sulfate solution containing 137 grams of A12(SO4)318H2O, (iron free), in a fine stream with good agitation to precipitate the aluminum soap. The aluminum soap is filtered and washed free of sulfate ion as indicated by barium chloride test solution. The soap is first dried by exposure to room atmosphere on an open tray, and final drying is accomplished over phosphorous pentoxide in a desiccator.
Equations: The aluminum di-acid soap is precipitated in accordance with the following simplified equations.
Some mono-acid soap may precipitate concurrently in accordance with the following equation:
atent Because of hydrolysis the iii-acid soap'AlRz does not form, and acid in excess of that required remains as such adsorbed on the di-acid soap as indicated in the following equation:
Example Ten grams of aluminum soap was added to 240 grams of gasoline or mixed hydrocarbon test solvent. As the soap particles swell the vortex will close around the stirrer shaft. After aging from 4 to 24 hours the resulting 4% gel will have a consistency suitable for use as a fire bomb fuel or mechanized flamethrower fuel. Thickened fuels of lower consistency suitable for use in the portable flamethrower can be prepared in a similar manner at a concentration of 1.8 to 2.0%.
The use of aluminum soaps of long chain acids such as coconut oil acids and other vegetable oil acids as thickener for liquid hydrocarbon fuels, is well known. The mixed iso-octoic acids of the present invention are believed to be new in the art and have several advantages over those of the longer chain fatty acids.
It is shown, for instance, that lower concentrations of the soap are required to produce fuels of equivalent consistency, and gelation of hydrocarbons can be accomplished at lower temperatures without use of a peptizing agent. This makes the soaps of the present invention more efiective per unit of weight than the older aluminum soaps and are more readily used in the field. They also have improved moisture resistance over that of the prior art soaps and accordingly result in more reproducible fuels. Finally, the availability of the iso-octoic acids is much greater than that of vegetable oil acids since they can be produced in large quantities from the mixed heptenes available in petroleum refining.
It is understood that the invention is not limited to the specific example given since the salts may be produced by any of the processes which are well known in the art.
I claim:
1. Aluminum mono and di-acid soaps, of mixed isooctoic acids.
2. An aluminum di-acid soap of mixed iso-octoic acids.
3. Aluminum mono and di-acid soaps of mixed isooctoic acids wherein the acids are principally methyl heptoic, dimethyl hexoic, and trimethyl pentoic.
4. Aluminum mono and di-acid soaps, of mixed iso octoic acids wherein the acids are principally methyl heptoic and dimethyl hexoic.
5. The process which comprises reacting a mixture of iso-octoic acids, comprising principally mono, diand tri-methyl substituted heptoic, hexoic and pentoic acids respectively, with approximately 50% excess sodium hydroxide, adding to the solution an excess of aluminum sulfate to precipitate aluminum mono and di-acid soaps of iso-octoic acids, washing the resulting insoluble hydroxy aluminum soap free of sulfate ion anddrying the aluminum soap.
(References on following page) References Cited in the file of this patent UNITED STATES PATENTS Minich Dec. 11, 1945 Gebhart et a1 Mar. 11, 1947 Hunn. Jan. 15, 1952 4 Ndwak et a1. Jan. 29, 1952 Hunn Nov. 18, 1952 Smith et a1. Jan. 13, 1953 Allison et a1. Feb. 10, 1953 Mason Aug. 11, 1953
Claims (1)
1. ALUMINUM MONO AND DI-ACID SOAPS, OF MIXED ISOOCTOIC ACIDS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US321747A US2741629A (en) | 1952-11-20 | 1952-11-20 | Aluminum soap of iso-octoic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US321747A US2741629A (en) | 1952-11-20 | 1952-11-20 | Aluminum soap of iso-octoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2741629A true US2741629A (en) | 1956-04-10 |
Family
ID=23251856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US321747A Expired - Lifetime US2741629A (en) | 1952-11-20 | 1952-11-20 | Aluminum soap of iso-octoic acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2741629A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905646A (en) * | 1955-07-15 | 1959-09-22 | Montedison Spa | Catalysts for the polymerization of olefines and process for preparing said catalysts |
| US2978411A (en) * | 1956-10-22 | 1961-04-04 | Exxon Research Engineering Co | Aluminum soap hydrocarbon thickener with increased solvation |
| US3018252A (en) * | 1958-11-24 | 1962-01-23 | James S Carson | Liquid gelling agent for gasoline |
| DE2158669A1 (en) * | 1971-11-26 | 1973-05-30 | Oil Base Germany Gmbh | Prevention of oil spillages - from damaged tankers by pumping in metal soap gelling agents |
| US4069236A (en) * | 1971-10-01 | 1978-01-17 | Emery Industries, Inc. | Aluminum acyloxides |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390609A (en) * | 1942-07-29 | 1945-12-11 | Nuodex Products Co Inc | Bodying agent for liquid hydrocarbons |
| US2417071A (en) * | 1943-08-14 | 1947-03-11 | Colgate Palmolive Peet Co | Preparation of water-insoluble organic salts |
| US2582833A (en) * | 1950-07-12 | 1952-01-15 | Sherwin Williams Co | Method for the preparation of aluminum and magnesium soaps |
| US2584041A (en) * | 1949-07-06 | 1952-01-29 | Nuodex Products Co Inc | Process of preparing oil-soluble metal soaps |
| US2618536A (en) * | 1950-09-20 | 1952-11-18 | Sherwin Williams Co | Gel-type fuel and method of making same |
| US2625527A (en) * | 1949-05-04 | 1953-01-13 | Standard Oil Dev Co | Alkyl esters and plastic compositions comprising same |
| US2628202A (en) * | 1949-09-23 | 1953-02-10 | Leffingwell Chemical Company | Soap useful for making lubricating greases |
| US2648694A (en) * | 1950-09-16 | 1953-08-11 | Standard Oil Dev Co | Higher fatty acid synthesis from oxo bottoms |
-
1952
- 1952-11-20 US US321747A patent/US2741629A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390609A (en) * | 1942-07-29 | 1945-12-11 | Nuodex Products Co Inc | Bodying agent for liquid hydrocarbons |
| US2417071A (en) * | 1943-08-14 | 1947-03-11 | Colgate Palmolive Peet Co | Preparation of water-insoluble organic salts |
| US2625527A (en) * | 1949-05-04 | 1953-01-13 | Standard Oil Dev Co | Alkyl esters and plastic compositions comprising same |
| US2584041A (en) * | 1949-07-06 | 1952-01-29 | Nuodex Products Co Inc | Process of preparing oil-soluble metal soaps |
| US2628202A (en) * | 1949-09-23 | 1953-02-10 | Leffingwell Chemical Company | Soap useful for making lubricating greases |
| US2582833A (en) * | 1950-07-12 | 1952-01-15 | Sherwin Williams Co | Method for the preparation of aluminum and magnesium soaps |
| US2648694A (en) * | 1950-09-16 | 1953-08-11 | Standard Oil Dev Co | Higher fatty acid synthesis from oxo bottoms |
| US2618536A (en) * | 1950-09-20 | 1952-11-18 | Sherwin Williams Co | Gel-type fuel and method of making same |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905646A (en) * | 1955-07-15 | 1959-09-22 | Montedison Spa | Catalysts for the polymerization of olefines and process for preparing said catalysts |
| US2978411A (en) * | 1956-10-22 | 1961-04-04 | Exxon Research Engineering Co | Aluminum soap hydrocarbon thickener with increased solvation |
| US3018252A (en) * | 1958-11-24 | 1962-01-23 | James S Carson | Liquid gelling agent for gasoline |
| US4069236A (en) * | 1971-10-01 | 1978-01-17 | Emery Industries, Inc. | Aluminum acyloxides |
| DE2158669A1 (en) * | 1971-11-26 | 1973-05-30 | Oil Base Germany Gmbh | Prevention of oil spillages - from damaged tankers by pumping in metal soap gelling agents |
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