US2130989A - Carboxylic acids of capillary action - Google Patents
Carboxylic acids of capillary action Download PDFInfo
- Publication number
- US2130989A US2130989A US2130989DA US2130989A US 2130989 A US2130989 A US 2130989A US 2130989D A US2130989D A US 2130989DA US 2130989 A US2130989 A US 2130989A
- Authority
- US
- United States
- Prior art keywords
- gamma
- acid
- butyric acid
- carboxylic acids
- acids
- 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
- 150000001735 carboxylic acids Chemical class 0.000 title description 8
- 210000001736 Capillaries Anatomy 0.000 title description 4
- 238000009835 boiling Methods 0.000 description 28
- 239000000194 fatty acid Substances 0.000 description 26
- 238000002844 melting Methods 0.000 description 24
- 239000002253 acid Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- -1 cyclo-alkyl radical Chemical class 0.000 description 20
- 239000007788 liquid Substances 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 230000000875 corresponding Effects 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001447 alkali salts Chemical class 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000003518 caustics Substances 0.000 description 8
- 150000001805 chlorine compounds Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000005187 foaming Methods 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-Tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-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
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-Methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 101700043552 KURT Proteins 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 229940036248 Turpentine Drugs 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 159000000013 aluminium salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 230000001050 lubricating Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 230000001131 transforming Effects 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- IZZOKZMGQDMCAE-XQZFLANJSA-N α-L-Rhap-(1->2)-[β-D-GlcpNAc-(1->3)]-α-L-Rhap-(1->3)-α-L-Rhap-(1->2)-[β-D-GlcpNAc-(1->3)]-α-L-Rhap Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](C)O[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)O[C@@H](C)[C@@H]1O IZZOKZMGQDMCAE-XQZFLANJSA-N 0.000 description 2
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
- C07C53/132—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Definitions
- the present invention relates to carboxylic acids, of capillary action, containing isocyclic ring-systems and to a process of preparing them.
- R an allwlene radical and A an'aromatic or hydroaromatic ring-system
- fatty acid radicals into 'alkylated or cycloalkylated aromatic hydrocarbons by condensing alkylated or cycloalkylated aromatic hydrocarbons with aliphatic dicarboxylic acids. including their anhydrides, acid chicrides or ester-acid chlorides and. reducing the ketocarboxylic acids thus formed to the corresponding carboxylic acids.
- these alkylor cycloalkylaryl-substituted fatty acids or the esters thereof are subjected to a catalytic hydrogenation and, if necessary, the hydrogenated esters are saponified.
- alkyl-a'ryi-fatty acids of the formula R1- A-Rs-COOH wherein R1 means alkyl, I A means an, aromatic rial-system and It: means CHsQI-IsCHs, or W,
- keto-carboxylic acids obtained by tainable according to these methods may, behyusing the acid ,anhydride's, the acid chlorides or the, ester-acid chlorides, are reduced to the corresponding fatty acids in an alkaline solution in the presence of line dust or catalytically' "activated hydrogen. 1
- the alkylor cycloalkyl aryl'f'atty acids obdrogenated, if necessary, with formation of hydroaromatic compounds which are completely saturated with hydrogen.
- the hydrogenation is carried out in. a particularly smooth manner by treating with hydrogen the esters of these acids with monohydric or polyhydric alcohols in the liquid phase 'at a temperature between 130 C.
- esters of the hydrogenated alkylaryi-fatty acids thus obacid, alkyl-phenanthrene fatty acids, 4-isobutyl-. cyclohexyl-gamma-butyric acid, i-cyclohexylcyclohexyl-gamma-butyric acid, dicyclohexylmethane-4-gamma-butyric acid etc.
- alkylated aromatic hydrocarbons there may be mentioned besides toluene, ethyl-, propyl-, butyl-benzenes, methylnaphthalene, cyclohexylbenzene or the like, the products which are, for
- the alkali salts of aryl-fatty acids as for instance, phenylacetic acid, phenyl-gammabutyric acid and so on, do not froth in aqueous solution
- the alkali salts of alkylaryl-fatty acids and the hydrogenation products thereof show a very good foaming power.
- Their wetting action surpasses that of the alkali salts of the corre-- sponding natural fatty acids
- the alkali salts of the perhydrogenated alkylaryl-fatty acids show in spite of the completely saturated character of the carboxylic acids from which they are prepared, an excellent solubility in water.
- the perhydrogenated alkylaryl-fatty acids are, on account of their saturated character, entirely stable. They are suitable, so far as they are liquid at room temperature, on account of their good lubricating power, as gliding agents for difierent purposes, for instance, greasing of wool, and show certain advantages over the oleic acid hitherto used for this purpose.
- the 4- butyl-cyclohexyl-gamma-butyric acid-methylester is obtained in the form of a colorless liquid boiling at 125 C. in a vacuum of 3 mm.
- CBi-CHE is obtained, constituting atroom temperature a colorless semi-solid mass and boiling at 150 C.
- aqueous solutions of the sodium salt are suitable as wetting agents, emulsifying agents and washing agents.
- Example 3 By replacing in Example 2 the 4-bu'ty1- phenyl-gamma-butyric acid by the 4-cyclohexylphenyl-gamma-butyric acid obtainable according to Example 3, there is obtained by way of the 4-cyclohexyl-phenyl-gamma-butyric acid-methyl ester and the 4-cyclohexyl-cyclohexyl-gamma-butyric acid-methyl ester, both representing colorless liquids boiling under a pressure of 3 mm.
- CHrCHr R a-O-c o-cm-cm-coon p-Ocm-onrcm-oo on an n-cm-cm-cm-co on Hr H:
- R1 means a member of the group consisting, of alkyl and cycloalkyl radicals containing at least 3 carbon atoms and A means a hexa- 2.
- Rmcmncoon wherein R1 means a member of the group consisting, of alkyl and cycloalkyl radicals containing at least 3 carbon atoms and A means a hexa- 2.
- CH-(CH:)r-COOH CHI-O 1 I being a colorless semi-solid mass boiling at 150 C. under a pressure of 3 mm. and being easily soluble in dilute caustic alkali solutions.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
names 2c, 1938 UNITED-STATES PATENT OFFICE GARBOXYLIC ACIDS OF CAPILLABY ACTION CONTAINING ISOCYCLIC RING-SYSTEMS AND A PROCESS OF PREPARING Kurt Schimmelschmidt, Frankfort-on-the-Main- Hochst, Germany, assignor to I. G. Farbenindustrie Aktiengesellschaft, Frankfort-on-the- Main Germany No Drawing.
rial No. 52,929. 1934 Application December 4, 1935, Se-
In Germany December 7,
4 Claims. (Cl. 260-514)- The present invention relates to carboxylic acids, of capillary action, containing isocyclic ring-systems and to a process of preparing them.
I have found that compounds of the general formula 'R1A--Ra-COOH wherein R1 means an alhl or cyclo-alkyl radical,
R: an allwlene radical and A an'aromatic or hydroaromatic ring-system,
are obtainable by introducing fatty acid radicals into 'alkylated or cycloalkylated aromatic hydrocarbons by condensing alkylated or cycloalkylated aromatic hydrocarbons with aliphatic dicarboxylic acids. including their anhydrides, acid chicrides or ester-acid chlorides and. reducing the ketocarboxylic acids thus formed to the corresponding carboxylic acids. In order to .obtain the hydroaromatic compounds corresponding to the above formula, these alkylor cycloalkylaryl-substituted fatty acids or the esters thereof are subjected to a catalytic hydrogenation and, if necessary, the hydrogenated esters are saponified.
The alkyl-a'ryi-fatty acids of the formula R1- A-Rs-COOH wherein R1 means alkyl, I A means an, aromatic rial-system and It: means CHsQI-IsCHs, or W,
are, for instance, obtained by condensation of the alkylated aromatic hydrocarbons-withlactones or functional derivatives of the succinic, acid, the glutaric acid or the adiplc acid series, such as their anhydrides, chloridesrand esterracid chlorides. The keto-carboxylic acids obtained by tainable according to these methods may, behyusing the acid ,anhydride's, the acid chlorides or the, ester-acid chlorides, are reduced to the corresponding fatty acids in an alkaline solution in the presence of line dust or catalytically' "activated hydrogen. 1
The alkylor cycloalkyl aryl'f'atty acids obdrogenated, if necessary, with formation of hydroaromatic compounds which are completely saturated with hydrogen. The hydrogenation is carried out in. a particularly smooth manner by treating with hydrogen the esters of these acids with monohydric or polyhydric alcohols in the liquid phase 'at a temperature between 130 C.
' and 200 C. in the presence of a nickel catalyst and with application of pressure. The esters of the hydrogenated alkylaryi-fatty acids thus obacid, alkyl-phenanthrene fatty acids, 4-isobutyl-. cyclohexyl-gamma-butyric acid, i-cyclohexylcyclohexyl-gamma-butyric acid, dicyclohexylmethane-4-gamma-butyric acid etc. I
As alkylated aromatic hydrocarbons there may be mentioned besides toluene, ethyl-, propyl-, butyl-benzenes, methylnaphthalene, cyclohexylbenzene or the like, the products which are, for
'instance, obtained by reaction of benzene, naphthalene or phenanthrene with commercial mixtures of alcohols, as, for instance, isobutyl oil (a by-product which is obtained in the methanolsynthesis) vor with the mixtures of alcohols obtained from commercial fatty acids by hydrogenation, or with mixtures of the alcohols obtainable by'the oxidation of paraflln; furthermore, the condensation products from benzene,
' naphthalene or phenanthrene with olefines or the polymerization products thereof as, for instance,
di-isobutylene, or with the unsaturated constitucuts of the compounds obtained in the cracking process or with oil of turpentine.
Whereas the alkali salts of aryl-fatty acids as for instance, phenylacetic acid, phenyl-gammabutyric acid and so on, do not froth in aqueous solution, the alkali salts of alkylaryl-fatty acids and the hydrogenation products thereof show a very good foaming power. Their wetting action surpasses that of the alkali salts of the corre-- sponding natural fatty acids, The alkali salts of the perhydrogenated alkylaryl-fatty acids show in spite of the completely saturated character of the carboxylic acids from which they are prepared, an excellent solubility in water. 'It is easily possible to prepare a cold parent solution of 20% strength and even of a higher percentage this being impossible when the saturated aliphatic carboxylic acids corresponding to them in the length of the chain are used. Furthermore, they show avery good washing action by which they surpass, for instance, on removal of the fat from wool, the alkali salts of saturated natural fatty acids, for instance, lauric acid. The perhydrogenated alkylaryl-fatty acids are, on account of their saturated character, entirely stable. They are suitable, so far as they are liquid at room temperature, on account of their good lubricating power, as gliding agents for difierent purposes, for instance, greasing of wool, and show certain advantages over the oleic acid hitherto used for this purpose.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto; the parts are by weight:
(1) 134 parts,of'n-butylbenzene (l-phenylbutane) are mixed with 100 parts of succinic acid anhydride and 500 parts of tetra-chlorethane and at 20 C.-30 C. 270 parts of anhydrous aluminium chloride are slowly introduced. After about 12 hours the mixture is heated to 50 C. until the reaction is finished; then it is poured on ice and after the addition of hydrochloric acid the whole is subjected to a steam distillation. The condensation product remains in the distillation vessel, after the complete elimination of the tetrachlorethane, in the form of a solid, granular mass and is separated from the aqueous solution of aluminium salts by filtration with suction. The crude product may be purified by recrystallization from chloro-benzene and there is'thus obtained the 4-butylphenyl-gamma-oxo gamma butyric acid of the following formula:
in the form of pearly leaflets melting at 115 C. to 116 C. I
200 parts of 4-butylphenyl-gamma-oxo-gamma-butyric acid are introduced into a suitable hydrogenation autoclave together with 200 parts of water and the calculated quantity of caustic soda solution and the mixture is treated with hydrogen, after the addition of a nickel catalyst, at a temperature between 70 C, to 200 C. under apressure of20 to 100 atmospheres. When the absorption of hydrogen is'finished the content of the autoclave is freed from the catalyst by filtration with suction and the reaction product is isolated from the alkaline solution by acidification. The 4-butyl-phenyl-gamma-butyric acid of the following formula:
cm-(onnOmmp-coon is-thus obtained, boiling at 170" 0.111 a vacuum organic solvents.
of 3 mm. and solidifying zit-53 C. in the form of a white solid mass which on crushing falls into fatty flaky leaflets. It is insoluble in water and very easily soluble in niost of the organic. solvents. In dilute caustic alkali solutions it is very easily soluble and yields strongly foaming solutions. The solution of 20% strength of the sodium salt thereof in water is a completely clear, liquid even when cold. The aqueous solution of the sodium salt may be used as a wetting agent.
(2) The 4-butyl-phenyl-gamma-butyric acid obtainable according to Example 1 is. esterified with methanol and sulfuric acid. The 4-buw1- phenyl-gamma-butyric acid-methylester is obtained as a colorless liquid boiling at 124 C. in
.a vacuum of 3 mm. and at 162C. in a vacuum of 12 mm. The ester isintroduced into a hydrogenation autoclave together with a nickel catalyst and treated at 130 C. to 200 with hydrogen under a pressure of 50 to 150 atmospheres until the absorbtion of hydrogen is finished. The
contents of the autoclave are filtered from the catalyst and subjected to distillation. The 4- butyl-cyclohexyl-gamma-butyric acid-methylester is obtained in the form of a colorless liquid boiling at 125 C. in a vacuum of 3 mm. By saponifying the ester the 4-hutyl-cyclohexylgamma-butyric acid of the following formula:
CBi-CHE is obtained, constituting atroom temperature a colorless semi-solid mass and boiling at 150 C.
in a vacuum of 3 mm.- It is practically insoluble in water, but very easily soluble in most of the It is easily soluble in dilute caustic alkali solutions and forms even in a solution' of 20% strength of the sodium salt thereof in water a clear liquid in the cold. The aqueous solutions of the sodium salt are suitable as wetting agents, emulsifying agents and washing agents.
(3) By replacing in mample 1 the butylbenzene by 160 parts of cyclohexylbenzenathere is obtained by way of the 4-cyclohexy1-phenyl-gamma-oxo-gamma butyric acid melting at 132 6. to 133 C., the 4-cyclohexyl-phenyl-gamma-butyric acid of the following formula Una-O \CHFCHS in the form of a colorless fatty mass having the structure of leaflets and solidifying at 56 C. The dilute aqueous solutions of its sodium salt have a very good foaming action and are suitable as wetting agents. From concentrated aqueous solutions the sodium salt crystallizes in the form of pearly leaflets.
(4) By replacing in Example 2 the 4-bu'ty1- phenyl-gamma-butyric acid by the 4-cyclohexylphenyl-gamma-butyric acid obtainable according to Example 3, there is obtained by way of the 4-cyclohexyl-phenyl-gamma-butyric acid-methyl ester and the 4-cyclohexyl-cyclohexyl-gamma-butyric acid-methyl ester, both representing colorless liquids boiling under a pressure of 3 mm.
' at 140 to 145 C.,- the 4-cyclohexyl-cyclohexylgamma-butyric acid of the following formula 170 C. alkali solutions to strongly foaming liquids.
CHrCHr R: a-O-c o-cm-cm-coon p-Ocm-onrcm-oo on an n-cm-cm-cm-co on Hr H:
CHrCHz-CHr Melting at i1s-1ao O Methyl ester boiling under a pres- Boiling under a pressure of 3 mm. at 150 sure of 3 mm. at 134 C. 0. liquid.
CH: Bolling under apressure cl3 mm.at
CH- Melting at 93 C Y Methyl ester boiling under a pres- Boiling under a pressure of 3 mm. at 150 CHr-CH: sure of 3 mm. at 133 C. 0. liquid. CH: Melting at 44 C. to 45 0., boiling solidifying at 66 C., iling under a under a pressure cl 2 mm. at 153 pressure 012mm. at 160 C. E-CHrCHr Melting at 07 C. to 90 C C.
CHI CH;-(CH;);- Melting at 95 C Melting at 56 0. to 57 C Btailing under a pressure oi 2 mm. at 170 CHI-(C Hi):- Melting at ION-104 C Solidilylng at 62 0., boiling under Boiling under a pressure of 2 mm. at 180 7 apressureoi3mm.at20b C. C. I
CHr-(GHs)n- Melting at 9l-02 O Boiidiiying at 71 C.
forming a white crystallne mass solidifying at hydrogenated benzene radical being colorless, liq- 83 C. and boiling under a pressure of 3 mm. at
uid to solid bodies dissolving in dilute caustic to form diphenyl-4-gammaeoxo-gamma-butyric add, melting at 187 C. to 188 C. and transforming it by way of diphenyl-i-gamma-butyric acid' melting at C. to 121 C. into the 4- cyclohexyl-cyclohexyl-gamma-butyric acid.
(5) In analogous manner there may be obtained the products indicated inthe following Rmcmncoon wherein R1 means a member of the group consisting, of alkyl and cycloalkyl radicals containing at least 3 carbon atoms and A means a hexa- 2. The 4-butyl-cyclohexyl-gamma-butyric acid of the formula CHr-CH,
CH-(CH:)r-COOH CHI-O 1 I being a colorless semi-solid mass boiling at 150 C. under a pressure of 3 mm. and being easily soluble in dilute caustic alkali solutions.
3. The 4-cyclohexyl-cyclohexyl-gamma-butyric acid of the formula CHz-CHI 'CHr- CH1 cg, cn -c CH-(CH1)s-CO on CHg-C CHr-C g 'ing of alkyl and cycloalkyl radicals containing at least 3 carbon atoms, with succinic acid anhydride, reducing the keto-carboxylic acids thus obtained to the corresponding substituted butyric acids, treating the acids thus obtained, in the .form of their esters, in the liquid phase with hydrogen under pressure at a temperature between C. and 200 C. in the presence of a nickel catalyst and finally saponifying the reaction product.
KURT SCHIllfldEUSCI-IMD'I.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2130989A true US2130989A (en) | 1938-09-20 |
Family
ID=3429671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2130989D Expired - Lifetime US2130989A (en) | Carboxylic acids of capillary action |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2130989A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2484497A (en) * | 1946-05-15 | 1949-10-11 | Eastman Kodak Co | Preparation of substituted lower aliphatic acids |
| US2560242A (en) * | 1949-01-03 | 1951-07-10 | Dow Chemical Co | Alpha-alkyl, 4-alkyl cyclohexylbutyric acids |
| US2623071A (en) * | 1948-05-13 | 1952-12-23 | Synor Res Lab Inc | Preparation of substituted cyclopentenones |
| US2749361A (en) * | 1951-08-29 | 1956-06-05 | Olin Mathieson | Cyclohexanecarboxamides |
| US2771487A (en) * | 1950-12-26 | 1956-11-20 | Shell Dev | Tertiary alkyl substituted cyclohexane carboxylic acids, derivatives thereof, and method for producing the same |
| US2894025A (en) * | 1955-09-07 | 1959-07-07 | Du Pont | Gamma-(3-aminocyclohexyl)butyric acid and esters |
| US4058558A (en) * | 1975-02-17 | 1977-11-15 | Pierre Fabre S.A. | Aromatic keto acids and derivatives having analgetic, antiinflammatory, and hypocholesterolemizing action |
-
0
- US US2130989D patent/US2130989A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2484497A (en) * | 1946-05-15 | 1949-10-11 | Eastman Kodak Co | Preparation of substituted lower aliphatic acids |
| US2623071A (en) * | 1948-05-13 | 1952-12-23 | Synor Res Lab Inc | Preparation of substituted cyclopentenones |
| US2560242A (en) * | 1949-01-03 | 1951-07-10 | Dow Chemical Co | Alpha-alkyl, 4-alkyl cyclohexylbutyric acids |
| US2771487A (en) * | 1950-12-26 | 1956-11-20 | Shell Dev | Tertiary alkyl substituted cyclohexane carboxylic acids, derivatives thereof, and method for producing the same |
| US2749361A (en) * | 1951-08-29 | 1956-06-05 | Olin Mathieson | Cyclohexanecarboxamides |
| US2894025A (en) * | 1955-09-07 | 1959-07-07 | Du Pont | Gamma-(3-aminocyclohexyl)butyric acid and esters |
| US4058558A (en) * | 1975-02-17 | 1977-11-15 | Pierre Fabre S.A. | Aromatic keto acids and derivatives having analgetic, antiinflammatory, and hypocholesterolemizing action |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2383633A (en) | Process for treating fatty glycerides | |
| US2130989A (en) | Carboxylic acids of capillary action | |
| GB2146638A (en) | Producing fatty acids from lower alkyl esters of fatty acids | |
| US3005846A (en) | Production of acids and esters | |
| US2716657A (en) | Method of producing orthophosphoric acid esters | |
| US2696500A (en) | Production of sebacic acid | |
| US3052698A (en) | Ester production | |
| US2975199A (en) | Olefin self-esterification | |
| US2043476A (en) | Cabboxylates of aliphatic alcohols | |
| US2094451A (en) | Production of hydroxy-sulfonic acids | |
| US1823815A (en) | Production of esters of sulphonic acids | |
| US2088308A (en) | Detergent composition | |
| US2088017A (en) | Oxygenated aliphatic compounds derived from 2-ethylbutyraldehyde | |
| DE720469C (en) | Process for the preparation of saturated hydroaromatic carboxylic acids | |
| US2321020A (en) | Detergent and method of making it | |
| US1967656A (en) | Agent for wetting, dispersing, etc. | |
| Ross et al. | The stability and constitution of monoglycerides | |
| US2341060A (en) | Sulphonated organic compound | |
| US1757441A (en) | Cleansing and emulsifying agent | |
| DE913418C (en) | Process for the production of organic sulfuric acid drops | |
| US3657293A (en) | Production of alkanoic acids | |
| Muskat et al. | Studies of conjugated systems. VI. The preparation of the geometric isomers of methylstyrylcarbinol and of phenylbutadiene | |
| US2962527A (en) | Purification of dibasic acids | |
| US3227737A (en) | Production of carboxylic acids from the residue of carbonylization process | |
| US1947673A (en) | Process of preparing esters |