US2215367A - Condensation products of acid amidelike constitution and process of preparing them - Google Patents
Condensation products of acid amidelike constitution and process of preparing them Download PDFInfo
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- US2215367A US2215367A US213424A US21342438A US2215367A US 2215367 A US2215367 A US 2215367A US 213424 A US213424 A US 213424A US 21342438 A US21342438 A US 21342438A US 2215367 A US2215367 A US 2215367A
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- Prior art keywords
- acid
- amidelike
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- condensation products
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
Definitions
- tion products having valuable properties may be obtained on a 100% synthetical base, by causing an amino-carboxylic acid or a water-soluble salt thereof to react with an isocyclic, for instance,
- R stands for a hydrocarbon radical with n at least 4 carbon atoms, n is the whole number 1 or a multiple of 1,
- A is an isocyclic ring system,
- X a COOH group or an aliphatic hydrocarbon radical carrying a COOH group the carbon chain or which may be interrupted by hetero-atoms 5 and which is bound to A either directly or by way of a hetero-atom, for instance, 0, S or N, the isocyclic carboxylic acid being suitably used in the form of a halide.
- R1 stands for a hydrocarbon radical of at least 4 carbon atoms
- n stands for an integer
- A stands for an isocyclic ring
- X stands for a member of the group consisting of CO, 2.00, O.Z.CO, S.Z.CO, NH.Z .CO, NR4.Z.CO
- Z being a member of the group consisting of aliphatic hydrocarbon radicals and aliphatic hydrocarbon radicals the carbon chain of which is interrupted by
- R2 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbonradicals
- Re and R4 stand for members of the group consisting of aliphatic and aromatic hydrocarbon radicals.
- carboxylic acids suitable for use in the invention there may be mentioned the following: aromatic or hydroaromatic carboxylic acids of the type of benzeneor hexahydrobenzene-carboxylic acids substituted by at least one hydrocarbon radical with at least 4 carbon atoms, such as isobutyl-benzoic acid, di-isobutyl benzoic acid, hexyl-benzoic acid, iso-octyl-toluic
- Amino-carboxylic acids which may be caused to react with the above-mentioned aromatic or hydroaromatic carboxylic acids are, for instance: amino-acetic acid, imino-diacetic acid, methylamino-acetic acid, amino-propionic acid, aminobutyric acid, alpha-methylamino-lauric acid; amino-acid mixtures, such as are present in the different stages of decomposition of natural albuminous compounds such aswool, silk, horn, leather; amino-benzoic acid, amino-phenoxyacetic acid, amino-salicylic acid.
- the reaction between members of the two classes of bodies to form the amidelike condensation product is preferably performed by causing a halide of the isocyclic carboxylic acid to act upon an aqueous solution of a salt of the amino-carboxylic acid.
- the reaction temperatures are generally situated between room temperature and about 100 C., in most cases there is used a moderately elevated temperature, about 30 C. to C.
- agents for binding the hydrogen halide there may be used, in this method of working, compounds having an alkaline action, or also organic bases.
- the new products are ,obtainedin the form of water-soluble salts, and some of them are 50 in the salt form crystalline, some of them are solid, crusty and pulverisable, others amorphous, viscous masses which in most cases still contain inorganic and organic salts.
- the free. amide-carboxylic acids which are, in most cases,
- hydrocarbon radicals, R: and R4 stand for members of the group consisting of aliphatic and aromatic hydrocarbon radicals.
- Rr-COOH wherein R1 stands for an aliphatic hydrocarbon radical of at least 4 carbon atoms, A stands for a member of the group consisting of the benzene ring and the cyclohexane ring, X stands for a member of the group consisting of CO, Z.CO, O.Z.CO, S.Z.CO, NH.Z.CO, NR4.ZiCO, Z being a member of the group consisting of aliphatic hydrocarbon radicals and aliphatic hydrocarbon radicals the carbon chain of which is interrupted by 0, R2 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, R: is an aliphatic hydrocarbon radical, R4 stands for a member of the group consisting of aliphatic and aromatic hydrocarbon radicals.
- R1 stands for an aliphatic hydrocarbon radical having 12 carbon atoms
- R: stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals
- R3 is an aliphatic hydrocarbon radical.
- R1 stands for an aliphatic hydrocarbon radical having 14 carbon atoms
- R: stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals
- R3 is an aliphatic hydrocarbon radical.
Description
Patented Sept. 17, 1940 PATENT OFFICE CONDENSATION PRODUCTS OF ACID AMIDE- LIKE CONSTITUTION .AND PROCESS OF PREPARING THEM Gerhard Balle and Heinz Schild, Frankfort-onthe-Main, Ge
rmany, assignors to I. G. Farbenindustrie Aktiengesellschaft, Frankfort-on-the- Main, Germany No Drawing. Application June 13, 1938, Serial No. 213,424. In Germany June 22, 1937 6 Claims. (01. 260-619) It is known that by the Schotten-Baumann" reaction carboiwlic acid amidelike condensation products may be made by causing the halides of natural fatty acids to react with amino-carboxylic acids or alkali salts thereof.
These amidelike condensation products and especially their water-soluble salts have obtained a commercial importance as wetting, dispersing and cleansing agents.
tion products having valuable properties may be obtained on a 100% synthetical base, by causing an amino-carboxylic acid or a water-soluble salt thereof to react with an isocyclic, for instance,
aromatic or hydroaromatic, carboxylic acid of the general formula:
(R) n.A.X
wherein R stands for a hydrocarbon radical with n at least 4 carbon atoms, n is the whole number 1 or a multiple of 1, A is an isocyclic ring system, X a COOH group or an aliphatic hydrocarbon radical carrying a COOH group the carbon chain or which may be interrupted by hetero-atoms 5 and which is bound to A either directly or by way of a hetero-atom, for instance, 0, S or N, the isocyclic carboxylic acid being suitably used in the form of a halide.
There may be obtained products of the 1'01- lowing general formula:
wherein R1 stands for a hydrocarbon radical of at least 4 carbon atoms, n stands for an integer,
"A stands for an isocyclic ring, X stands for a member of the group consisting of CO, 2.00, O.Z.CO, S.Z.CO, NH.Z .CO, NR4.Z.CO, Z being a member of the group consisting of aliphatic hydrocarbon radicals and aliphatic hydrocarbon radicals the carbon chain of which is interrupted by 0, R2 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbonradicals, Re and R4 stand for members of the group consisting of aliphatic and aromatic hydrocarbon radicals.
Among the carboxylic acids suitable for use in the invention there may be mentioned the following: aromatic or hydroaromatic carboxylic acids of the type of benzeneor hexahydrobenzene-carboxylic acids substituted by at least one hydrocarbon radical with at least 4 carbon atoms, such as isobutyl-benzoic acid, di-isobutyl benzoic acid, hexyl-benzoic acid, iso-octyl-toluic Now we have found that amidelike condensaacid, dodecyl-xylic acid, isotetradecyl-naphthoic acid, octodecyl-hexahydrobenzoic acid, isooctyl-salicylic acid, furthermore carboxylic acids substituted in the ring system at least once in an analogous .manner' of the type of the 5 phenoxyor hexahydrophenoxy-alkyl-carboxylic acids, such as iso-butyl-phenoiwacetic acid, isohexyl-cresoxyacetic acids, iso-octylxylene-hydroxypropionic acids, dibutylnaphthoxy-acetic acids, isododecyl-hexahydrophenoxyacetic acid, isotetradecyl-phenoxy-alpha-butyric acid, paracyclohexyl-phenoxy-alpha-lauric acid, orthoand para-benzylphenoxy-propionic acid, paraphenyl-phenoxyacetic acid, the .hydrogenation products of these acids, iso-octyl-phenoxyethoxyacetic acid, dodecylphenyl-pentaglycol ether acetic acid, iso-octyl-phenylglycine, isoheptylphenyl-mercapto-acetic acid, furthermore carboxylic acids of the type of the substituted phenylacetic acid, such as the tri-butyl-phenylacetic acid, iso-octylphenyl-hydrocinnamic acid, butylphenyl-butyric acid, dodecyl-benzoyl-propionic acid, cyclohexyl-benzoyl-benzoic acid.
Amino-carboxylic acids which may be caused to react with the above-mentioned aromatic or hydroaromatic carboxylic acids are, for instance: amino-acetic acid, imino-diacetic acid, methylamino-acetic acid, amino-propionic acid, aminobutyric acid, alpha-methylamino-lauric acid; amino-acid mixtures, such as are present in the different stages of decomposition of natural albuminous compounds such aswool, silk, horn, leather; amino-benzoic acid, amino-phenoxyacetic acid, amino-salicylic acid.
The reaction between members of the two classes of bodies to form the amidelike condensation product is preferably performed by causing a halide of the isocyclic carboxylic acid to act upon an aqueous solution of a salt of the amino-carboxylic acid. The reaction temperatures are generally situated between room temperature and about 100 C., in most cases there is used a moderately elevated temperature, about 30 C. to C. As agents for binding the hydrogen halide there may be used, in this method of working, compounds having an alkaline action, or also organic bases.
The new products are ,obtainedin the form of water-soluble salts, and some of them are 50 in the salt form crystalline, some of them are solid, crusty and pulverisable, others amorphous, viscous masses which in most cases still contain inorganic and organic salts. The free. amide-carboxylic acids which are, in most cases,
hydrocarbon radicals, R: and R4 stand for members of the group consisting of aliphatic and aromatic hydrocarbon radicals.
3. As new compounds the products of the general formula:
Rr-COOH wherein R1 stands for an aliphatic hydrocarbon radical of at least 4 carbon atoms, A stands for a member of the group consisting of the benzene ring and the cyclohexane ring, X stands for a member of the group consisting of CO, Z.CO, O.Z.CO, S.Z.CO, NH.Z.CO, NR4.ZiCO, Z being a member of the group consisting of aliphatic hydrocarbon radicals and aliphatic hydrocarbon radicals the carbon chain of which is interrupted by 0, R2 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, R: is an aliphatic hydrocarbon radical, R4 stands for a member of the group consisting of aliphatic and aromatic hydrocarbon radicals.
4. As new compounds the products of the general formula:
wherein R1 stands for an aliphatic hydrocarbon radical having 12 carbon atoms, R: stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, R3 is an aliphatic hydrocarbon radical.
5. As new compounds the products of the general formula Ra.OOOH
Ra.COOH
wherein R1 stands for an aliphatic hydrocarbon radical having 14 carbon atoms, R: stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, R3 is an aliphatic hydrocarbon radical.
GERHARD BALLE. HEINZ SCHILD.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2215367X | 1937-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2215367A true US2215367A (en) | 1940-09-17 |
Family
ID=7990526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US213424A Expired - Lifetime US2215367A (en) | 1937-06-22 | 1938-06-13 | Condensation products of acid amidelike constitution and process of preparing them |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2215367A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2463941A (en) * | 1945-08-24 | 1949-03-08 | Lilly Co Eli | Phenacetyl amino acids |
| US3039861A (en) * | 1959-12-01 | 1962-06-19 | Socony Mobil Oil Co Inc | Glycine alkenyl succinamic acids in distillate fuels |
| US3487105A (en) * | 1966-12-16 | 1969-12-30 | American Home Prod | Alpha-aminoacyl-omega-aminocarboxylic acids |
| US4067998A (en) * | 1974-02-11 | 1978-01-10 | The Dow Chemical Company | 2-((3,5-Di-tert-butylphenyl)thio) alkanoic acids and derivatives |
-
1938
- 1938-06-13 US US213424A patent/US2215367A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2463941A (en) * | 1945-08-24 | 1949-03-08 | Lilly Co Eli | Phenacetyl amino acids |
| US3039861A (en) * | 1959-12-01 | 1962-06-19 | Socony Mobil Oil Co Inc | Glycine alkenyl succinamic acids in distillate fuels |
| US3487105A (en) * | 1966-12-16 | 1969-12-30 | American Home Prod | Alpha-aminoacyl-omega-aminocarboxylic acids |
| US4067998A (en) * | 1974-02-11 | 1978-01-10 | The Dow Chemical Company | 2-((3,5-Di-tert-butylphenyl)thio) alkanoic acids and derivatives |
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