GB806113A - Improvements relating to aluminium alcoholate derivatives - Google Patents
Improvements relating to aluminium alcoholate derivativesInfo
- Publication number
- GB806113A GB806113A GB410955A GB410955A GB806113A GB 806113 A GB806113 A GB 806113A GB 410955 A GB410955 A GB 410955A GB 410955 A GB410955 A GB 410955A GB 806113 A GB806113 A GB 806113A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aluminium
- heating
- acids
- acid
- give
- 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
Links
- 229910052782 aluminium Inorganic materials 0.000 title abstract 10
- 239000004411 aluminium Substances 0.000 title abstract 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title abstract 7
- 238000010438 heat treatment Methods 0.000 abstract 12
- -1 acyloxy aluminium compounds Chemical class 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 229940077746 antacid containing aluminium compound Drugs 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- 239000000047 product Substances 0.000 abstract 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- 235000021355 Stearic acid Nutrition 0.000 abstract 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 abstract 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 4
- 150000001399 aluminium compounds Chemical class 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 159000000032 aromatic acids Chemical class 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 235000020778 linoleic acid Nutrition 0.000 abstract 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 abstract 2
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 2
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 2
- 235000021313 oleic acid Nutrition 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 2
- 150000004707 phenolate Chemical class 0.000 abstract 2
- 229940031826 phenolate Drugs 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 239000008117 stearic acid Substances 0.000 abstract 2
- 239000003784 tall oil Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- HJFUUQISSHZQRS-UHFFFAOYSA-M acetyloxyaluminum(2+);propan-2-olate Chemical compound CC(C)[O-].CC(C)[O-].CC(=O)O[Al+2] HJFUUQISSHZQRS-UHFFFAOYSA-M 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- LXVDSDPFRBWEFN-UHFFFAOYSA-M di(propan-2-yloxy)alumanyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](OC(C)C)OC(C)C LXVDSDPFRBWEFN-UHFFFAOYSA-M 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 abstract 1
- 229940011051 isopropyl acetate Drugs 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
The invention comprises condensed organic aluminium compounds of general formulae <FORM:0806113/IV (a)/1> and (b) <FORM:0806113/IV (a)/2> in which R1 is an alkyl or aryl radical and X is the radical of a monocarboxylic acid HX. They are prepared from acyloxyaluminium alcoholates or phenolates, which are obtained by heating one mol. of aluminium alcoholate or phenolate with up to 2.4 mols. of monocarboxylic acid, by heating the acyloxy aluminium compounds to a temperature higher than that used in their preparation. The condensation products may be further reacted with alcoholic or phenolic hydroxy compounds, water or carboxylic acids. The compound of formula (a) above on heating to a temperature above 230 DEG C. gives (O=Al.OR1)n in which n has an integral value and the compound of formula (b) on further heating, e.g. to 200 DEG -300 DEG C. gives (O=AIX)n. The monocarboxylic acids used are for example fatty acids such as stearic, oleic and linoleic acids; cycloaliphatic acids such as the naphthenic acids; aromatic acids such as benzoic acid; and acid mixtures such as tall oil. The aluminium alkoxide used as starting material may be a mixed alkoxide-phenoxide.ALSO:The invention comprises condensed organic aluminium compounds of the general formulae <FORM:0806113/IV (b)/1> and <FORM:0806113/IV (b)/2> in which R1 is an alkyl or aryl radical and X is the radical of a monocarboxylic acid HX. They may be prepared from acyloxy aluminium alcoholates or phenolates, which are obtained by heating and reacting one mol. of aluminium alcoholate or phenolate with up to 2.4 mols. of monocarboxylic acid, by heating the acyloxy aluminium compounds to a temperature higher than that used for their preparation and condensing them to form partially or completely condensed aluminium compounds with liberation of ester. The condensation products may be further reacted with alcoholic or phenolic hydroxy compounds, water or carboxylic acids to give useful products. Where 1 and 2 mols. of acid/mol. of aluminium alcoholate are used the intermediate products are believed to have the formula (1) <FORM:0806113/IV (b)/3> and (2) <FORM:0806113/IV (b)/4> respectively, R1OH and R2OH representing the alcohols used in the preparation of the alcoholate and HX being the acid used. The compound of formula (1) on further heating to a temperature in the range 150-230 DEG C. gives <FORM:0806113/IV (b)/5> and this on heating to a temperature above 230 DEG C. gives (O = Al-OR1)n where n has an integral value. On heating the compound of formula (2) up to 160 DEG C. the compound <FORM:0806113/IV (b)/6> is obtained and on heating this to higher temperatures the compound (O = Al.X)n is obtained. The monocarboxylic acids used are, for example, fatty acids such as stearic, oleic and linoleic acids; cycloaliphatic acids such as the naphthenic acids; aromatic acids such as benzoic acid; and acid mixtures such as tall oil. The aluminium alkoxide used as starting material may be a mixed alkoxide-phenoxide. The alcohols used in the formation of the alkoxides may be primary, secondary or tertiary and may be normal or otherwise. In the examples: (a) aluminium isopropoxide is mixed with an equimolar amount of stearic acid and the mixture is heated to 90 DEG C. to give aluminium di-isopropoxide monostearate; the temperature is raised to 185 DEG C. to give a liquid mixture containing a compound of formula (3) in which X is a stearate radical and R1 is an isopropyl radical; (b) the mixture obtained in (a) is heated to 230 DEG C. to give a solid of formula (3) in which X is a stearate radical and R1 is an isopropyl radical; (c) aluminium isopropoxide is heated with stearic acid and acetic acid to 70 DEG C. and the product is heated to 260 DEG C. to give a condensed aluminium product; (d) aluminium isopropoxide is heated with an equimolar amount of acetic acid to give aluminium monoacetate di-isopropoxide which is heated to 200 DEG C. when an equimolar amount of isopropyl acetate distils off: on heating to 250 DEG C. a compound corresponding to the formula (O = Al-OPr)n is obtained; and (e) aluminium isopropoxide is heated with octoic acid to 100 DEG C. with loss of isopropanol; the temperature is raised to 150 DEG and then to 210 DEG C. with further loss of isopropanol to give a condensed aluminium - containing product; further heating to 325 DEG C. brings about further condensation to give isopropyl octoate and a condensed aluminium-containing product.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB410955A GB806113A (en) | 1955-02-11 | 1955-02-11 | Improvements relating to aluminium alcoholate derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB410955A GB806113A (en) | 1955-02-11 | 1955-02-11 | Improvements relating to aluminium alcoholate derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB806113A true GB806113A (en) | 1958-12-17 |
Family
ID=9770957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB410955A Expired GB806113A (en) | 1955-02-11 | 1955-02-11 | Improvements relating to aluminium alcoholate derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB806113A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1265901B (en) * | 1962-01-17 | 1968-04-11 | British Petroleum Co | Cutting oil |
DE4011783A1 (en) * | 1989-05-03 | 1990-11-08 | Komaromi Koeolajipari Vallalat | Aluminium oxide carboxylate polymer prodn. - by reaction of aluminium alcoholate, mono:carboxylic acid and water to give lower ester content |
-
1955
- 1955-02-11 GB GB410955A patent/GB806113A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1265901B (en) * | 1962-01-17 | 1968-04-11 | British Petroleum Co | Cutting oil |
DE4011783A1 (en) * | 1989-05-03 | 1990-11-08 | Komaromi Koeolajipari Vallalat | Aluminium oxide carboxylate polymer prodn. - by reaction of aluminium alcoholate, mono:carboxylic acid and water to give lower ester content |
US5075473A (en) * | 1989-05-03 | 1991-12-24 | Komaromi Koolajipari V. | Process for the preparation of aluminum oxide carboxylate polymers containing at most two percent by weight of ester |
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