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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- US
- United States
- Prior art keywords
- acid
- amidelike
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- group
- condensation products
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- Expired - Lifetime
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- 239000002253 acid Substances 0.000 title description 6
- 239000007859 condensation product Substances 0.000 title description 5
- 238000000034 method Methods 0.000 title description 3
- 239000000047 product Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- -1 iso-octylxylene-hydroxypropionic acids Chemical class 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- KELWUXZVDGEJAW-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)benzoic acid Chemical compound CC(C)CC1=CC=CC(C(O)=O)=C1CC(C)C KELWUXZVDGEJAW-UHFFFAOYSA-N 0.000 description 1
- XLARYHDHLKLDTP-UHFFFAOYSA-N 2-(12-methyltridecyl)naphthalene-1-carboxylic acid Chemical compound C(CCCCCCCCCCC(C)C)C1=C(C2=CC=CC=C2C=C1)C(=O)O XLARYHDHLKLDTP-UHFFFAOYSA-N 0.000 description 1
- GDPSGDGVOGWDFN-UHFFFAOYSA-N 2-(2,3,4-tributylphenyl)acetic acid Chemical compound C(CCC)C1=C(C(=C(C=C1)CC(=O)O)CCCC)CCCC GDPSGDGVOGWDFN-UHFFFAOYSA-N 0.000 description 1
- PSHADDQTSCEAHY-UHFFFAOYSA-N 2-(2-methylpropyl)benzoic acid Chemical compound CC(C)CC1=CC=CC=C1C(O)=O PSHADDQTSCEAHY-UHFFFAOYSA-N 0.000 description 1
- YHGUMRTUPLJIKX-UHFFFAOYSA-N 2-(6-methylheptoxy)benzoic acid Chemical compound CC(C)CCCCCOC1=CC=CC=C1C(O)=O YHGUMRTUPLJIKX-UHFFFAOYSA-N 0.000 description 1
- PVEJXVQJOOJZGK-UHFFFAOYSA-N 2-(6-methylheptylamino)-2-phenylacetic acid Chemical compound C(CCCCC(C)C)NC(C1=CC=CC=C1)C(=O)O PVEJXVQJOOJZGK-UHFFFAOYSA-N 0.000 description 1
- CBFMHULESRECBI-UHFFFAOYSA-N 2-(methylamino)dodecanoic acid Chemical compound CCCCCCCCCCC(NC)C(O)=O CBFMHULESRECBI-UHFFFAOYSA-N 0.000 description 1
- AMVRSHNTGTWNLY-UHFFFAOYSA-N 2-amino-2-phenoxyacetic acid Chemical compound OC(=O)C(N)OC1=CC=CC=C1 AMVRSHNTGTWNLY-UHFFFAOYSA-N 0.000 description 1
- RKUJMRASAORISN-UHFFFAOYSA-N 2-benzoyl-2-methyltetradecanoic acid Chemical compound C(CCCCCCCCCCC)C(C(=O)O)(C)C(C1=CC=CC=C1)=O RKUJMRASAORISN-UHFFFAOYSA-N 0.000 description 1
- CDJJHNHJCNFGSO-UHFFFAOYSA-N 2-benzoyl-3-cyclohexylbenzoic acid Chemical compound C1(CCCCC1)C=1C(=C(C(=O)O)C=CC1)C(C1=CC=CC=C1)=O CDJJHNHJCNFGSO-UHFFFAOYSA-N 0.000 description 1
- LJWPUSKKVGUQAF-UHFFFAOYSA-N 2-benzyl-8-methyl-2-phenylnonanoic acid Chemical compound C(CCCCC(C)C)C(C(=O)O)(CC1=CC=CC=C1)C1=CC=CC=C1 LJWPUSKKVGUQAF-UHFFFAOYSA-N 0.000 description 1
- JVQQZZRVPPRACZ-UHFFFAOYSA-N 2-cyclohexyloxy-12-methyltridecanoic acid Chemical compound C(CCCCCCCCC(C)C)C(C(=O)O)OC1CCCCC1 JVQQZZRVPPRACZ-UHFFFAOYSA-N 0.000 description 1
- SLSXJXINWDAQAB-UHFFFAOYSA-N 2-ethyl-2-phenylhexanoic acid Chemical compound CCCCC(CC)(C(O)=O)C1=CC=CC=C1 SLSXJXINWDAQAB-UHFFFAOYSA-N 0.000 description 1
- YQIASAUDDDCAKU-UHFFFAOYSA-N 2-hexylbenzoic acid Chemical compound CCCCCCC1=CC=CC=C1C(O)=O YQIASAUDDDCAKU-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical class O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- ZXZNFXDGMGIZPT-UHFFFAOYSA-N 4-dodecyl-2,3-dimethylbenzoic acid Chemical compound C(CCCCCCCCCCC)C1=C(C(=C(C=C1)C(=O)O)C)C ZXZNFXDGMGIZPT-UHFFFAOYSA-N 0.000 description 1
- KNWIDLCZHAGPKQ-UHFFFAOYSA-N 8-methyl-2-(2-phenoxyethoxy)nonanoic acid Chemical compound C(CCCCC(C)C)C(C(=O)O)OCCOC1=CC=CC=C1 KNWIDLCZHAGPKQ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical group OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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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