GB536881A - Process for the production of water-soluble high molecular ª‡-substituted aralkyl amines and derivatives thereof, and the resulting products - Google Patents
Process for the production of water-soluble high molecular ª‡-substituted aralkyl amines and derivatives thereof, and the resulting productsInfo
- Publication number
- GB536881A GB536881A GB30704/39A GB3070439A GB536881A GB 536881 A GB536881 A GB 536881A GB 30704/39 A GB30704/39 A GB 30704/39A GB 3070439 A GB3070439 A GB 3070439A GB 536881 A GB536881 A GB 536881A
- Authority
- GB
- United Kingdom
- Prior art keywords
- undecylbenzylamine
- treated
- sulphonated
- acid
- aralkylamines
- 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
- 150000003974 aralkylamines Chemical class 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 2
- -1 sulphonic acid ester Chemical class 0.000 abstract 12
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 7
- DEJJVDGDQBHRBM-UHFFFAOYSA-N 1-phenyldodecan-1-amine Chemical compound CCCCCCCCCCCC(N)C1=CC=CC=C1 DEJJVDGDQBHRBM-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 abstract 5
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 5
- 239000000194 fatty acid Substances 0.000 abstract 5
- 229930195729 fatty acid Natural products 0.000 abstract 5
- 150000004665 fatty acids Chemical class 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- JXVSSAXEIFJOLW-UHFFFAOYSA-N CC(C1=CC=C(C=C1)CCCCCCCCCCCC)N Chemical compound CC(C1=CC=C(C=C1)CCCCCCCCCCCC)N JXVSSAXEIFJOLW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 3
- MNDLQOYHDBDINR-UHFFFAOYSA-N 1-(4-methoxyphenyl)dodecan-1-amine Chemical compound CCCCCCCCCCCC(N)C1=CC=C(OC)C=C1 MNDLQOYHDBDINR-UHFFFAOYSA-N 0.000 abstract 2
- MTEATTHFJDCQLP-UHFFFAOYSA-N 1-(4-methylphenyl)dodecan-1-amine Chemical compound CCCCCCCCCCCC(N)C1=CC=C(C)C=C1 MTEATTHFJDCQLP-UHFFFAOYSA-N 0.000 abstract 2
- DJNJZIFFCJTUDS-UHFFFAOYSA-N 1-phenyldodecan-1-one Chemical compound CCCCCCCCCCCC(=O)C1=CC=CC=C1 DJNJZIFFCJTUDS-UHFFFAOYSA-N 0.000 abstract 2
- IOXCQANOOMEVDN-UHFFFAOYSA-N 1-phenyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCC(N)C1=CC=CC=C1 IOXCQANOOMEVDN-UHFFFAOYSA-N 0.000 abstract 2
- CCGYLEPCYLNRAN-UHFFFAOYSA-N 4-(1-aminododecyl)-N,N-dimethylaniline Chemical compound CCCCCCCCCCCC(N)C1=CC=C(C=C1)N(C)C CCGYLEPCYLNRAN-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 239000002168 alkylating agent Substances 0.000 abstract 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000012435 aralkylating agent Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 238000009736 wetting Methods 0.000 abstract 2
- AZJLZOVPJNPLGE-UHFFFAOYSA-N 1-(4-methylphenyl)-2-phenylethanamine Chemical compound C1=CC(C)=CC=C1C(N)CC1=CC=CC=C1 AZJLZOVPJNPLGE-UHFFFAOYSA-N 0.000 abstract 1
- WSQOGHJCBFRHSI-UHFFFAOYSA-N 1-(4-phenoxyphenyl)ethanamine Chemical compound C1=CC(C(N)C)=CC=C1OC1=CC=CC=C1 WSQOGHJCBFRHSI-UHFFFAOYSA-N 0.000 abstract 1
- LHORZPMPPHTXFQ-UHFFFAOYSA-N 1-chloroethanesulfonic acid Chemical compound CC(Cl)S(O)(=O)=O LHORZPMPPHTXFQ-UHFFFAOYSA-N 0.000 abstract 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- MAHPVQDVMLWUAG-UHFFFAOYSA-N 1-phenylhexan-1-one Chemical compound CCCCCC(=O)C1=CC=CC=C1 MAHPVQDVMLWUAG-UHFFFAOYSA-N 0.000 abstract 1
- DBLXXVQTWJFJFI-UHFFFAOYSA-N 1-phenyloctadecan-1-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)C1=CC=CC=C1 DBLXXVQTWJFJFI-UHFFFAOYSA-N 0.000 abstract 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 abstract 1
- CREPHNZWUXZODH-UHFFFAOYSA-N 4-chloro-1-phenyldodecan-1-one Chemical compound ClC(CCC(=O)C1=CC=CC=C1)CCCCCCCC CREPHNZWUXZODH-UHFFFAOYSA-N 0.000 abstract 1
- ONZXEBDDYUHTMZ-UHFFFAOYSA-N 4-methoxy-1-phenyldodecan-1-one Chemical compound COC(CCC(=O)C1=CC=CC=C1)CCCCCCCC ONZXEBDDYUHTMZ-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- YFUYUIXMGAEZQX-UHFFFAOYSA-N N,N-dimethyl-1-phenyloctadecan-1-amine Chemical compound C(CCCCCCCCCCCCCCCC)C(C1=CC=CC=C1)N(C)C YFUYUIXMGAEZQX-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 abstract 1
- MLAZDYLGUGMAOQ-UHFFFAOYSA-N chloromethylbenzene;dimethyl sulfate Chemical compound COS(=O)(=O)OC.ClCC1=CC=CC=C1 MLAZDYLGUGMAOQ-UHFFFAOYSA-N 0.000 abstract 1
- OONHJKCKWRTEBL-UHFFFAOYSA-N chlorosulfonyloxymethylbenzene Chemical compound ClS(=O)(=O)OCC1=CC=CC=C1 OONHJKCKWRTEBL-UHFFFAOYSA-N 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 abstract 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000003893 lactate salts Chemical class 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- YVEDFCADLFFKDY-UHFFFAOYSA-N n-(1-phenylethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC(C)C1=CC=CC=C1 YVEDFCADLFFKDY-UHFFFAOYSA-N 0.000 abstract 1
- SSHCTTVYKJFTFS-UHFFFAOYSA-N n-benzhydryldodecanamide Chemical compound C=1C=CC=CC=1C(NC(=O)CCCCCCCCCCC)C1=CC=CC=C1 SSHCTTVYKJFTFS-UHFFFAOYSA-N 0.000 abstract 1
- PTARJSBAWUAIQA-UHFFFAOYSA-N n-benzyl-n-methylundecan-1-amine Chemical compound CCCCCCCCCCCN(C)CC1=CC=CC=C1 PTARJSBAWUAIQA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 abstract 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000009877 rendering Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
536,881. α-Aralkylamine derivatives; wetting &c. agents ; proofing permeable materials. GEIGY AKT.-GES.. J. R. Nov. 24, 1939, Nos. 30704 and 30705. Convention dates, Nov. 25, 1938 and Dec. 1, 1938. [Classes 2 (iii) and 15 (ii)] [Also in Groups III and VIII] Aralkylamines containing an aliphatic residue having at least eight carbon atoms and having the formula AC (HR)N(R 1 X) in which A is a benzene, naphthalene or partly hydrogenated naphthalene residue, R is alkyl, aralkyl or aryl, R 1 is hydrogen, alkyl, hydroxyalkyl or aralkyl and X is hydrogen, alkyl, hydroxyalkyl or aralkyl are converted into water soluble derivatives by reacting them with acids to form salts, if necessary after partial alkylation or aralkylation, or exhaustively with alkylating or aralkylating agents. When the aralkylamines have an N-acyl group, solubility may also be effected by treating with sulphonating agents if necessary in combination with partial alkylation, aralkylation or acylation. The hydrochlorides, sulphates, oxalates, acetates and lactates of secondary and tertiary derivatives of the aralkylamines are mentioned. As alkylating and aralkylating agents the following are specified : alkylhalides such as methyl and allylchloride, diethylsulphate, sulphonic acid ester, halogen ketones, halogenalkylnitriles, halogenalkylihodanides, and halogenhydroxybenzylhalides. For acylation of the aralkylamines when the sulphonation process is employed carboxylic and sulphonic acids or their esters or halides such as benzoyl-chloride, palm nut fatty acid chloride, propionylchloride, naphthenic acid chloride, toluene, sulphochloride, benzylsulphonic acid chloride and tetrahydronaphthalenesulphochloride may be used. Sulphonic acid groups may be introduced directly or by re-acting with sulphoalkyl or sulphoaralkyl halides. The products are stated to have wetting, washing, softening, foaming, equalizing and dispersing properties and may be used as mothproofing agents, insecticides and disinfectants. They also produce insoluble precipitates with dyestuffs having acid groups and may thus be used for rendering acid dyeings fast. In examples : (1) α-undecylbenzylamine is converted into a tertiary base by means of dimethylsulphate and then into the corresponding quaternary ammonium compound by treating with dimethylsulphate, glycerolchlorhydrin and allylbromide; (2) 4-dimethylamino-α-undecylbenzylamine is treated with. dimethylsulphate to form a quaternary ammonium salt; (3) α- heptadecylbenzylamine is converted into α- heptadecylbenzyldimethylamine by means of dimethyl sulphate and then sulphonated or converted into a quaternary ammonium salt by means of chloracetic acid ethylester , (4) 4- methoxy-α-undecylbenzylamine is treated first with dimethyl sulphate and then with 3:4- dichlorbenzylchloride ; (5) α-methyl-4-laurylbenzylamine is treated first with dimethylsulphate and a quaternary ammonium salt formed with diethylsulphate, allylbromide or chloracetamide ; (6) α-undecylbenzylamine is acylated and the resulting formyl-, acetyl-, butyryl-, benzoyl-, phenoxyacetyl-, phenylacetyl-, and salicylyl-α- undecylbenzylamines sulphonated; (7) N-methyl-undecylbenzylamine is similarly acylated and then sulphonated ; (8) 4-methyl-α-undecylbenzylamine is treated with benzylchloride dimethylsulphate glycerinchlorhydrin benzylsulphochloride, toluene sulphochloride and then sulphonated ; (9) 4-methoxy-α-undecylbenzylamine is treated with benzylchloride and acetyl chloride and then sulphonated; (10) α-methylbenzylamine is treated with palm fatty acid chloride and the lauric acid-N- (α-methylbenzyl) amide sulphonated ; α-substituted benzylamines derived from butyrophenone, amylphenylketone and naphthylmethylketone may also be similarly treated ; (11) 4-dodecyl-α-methylbenzylamine is benzoylated and sulphonated ; (12) 4-phenoxy-α-methylbenzylamine is first treated. with capric acid chloride and then sulphonated ; (13) α-undecylbenzyl amine is treated with toluenesulphochloride and dimethylsulphate and the resulting N-methyl-α-undecylbenzyltoluenesulphamide sulphonated ; (14) α-undecylbenzylamine is treated with tetra-hydronaphthalenesulphochloride and the product sulphonated ; (15) α-benzyl-4-methylbenzylamine is treated with stearic acid chloride and sulphonated ; (16) α-phenylbenzylamine is treated with palm fatty acid chloride and the resulting lauric acid-N-(α-phenylbenzyl) amide sulphonated: (17) α-undecylbenzylamine is ,reacted with benzylchloride-4-sulphonic acid and chlorethane sulphonic acid α-substituted aralkylamines are prepared by reacting the appropriate arylketone with ammonium formate. Thus laurophenone by heating with ammonium formate and saponification of the resulting formyl compound yields α-undecylbenzylamine and stearophenone yields α-heptadecylbenzylamine. The ketones, by hydrogenating in the presence of ammonia also give the α-substituted aralkylamines. 4-Dimethylamino - α - undecylbenzylamine is prepared by reacting 4-chlorlaurophenone with dimethylamine and heating the product with ammonium formate. 4- methoxylaurophenone is produced from palm fatty acid and anisol. α-Methyl-4-laurylbenzylamine is prepared by refluxing laurophenone with amalgamated zinc and hydrochloric acid to give laurylbenzene. The latter is condensed with acetic anhydride, using aluminium chloride in carbondisulphide and the resulting 4-laurylacetophenone treated with ammonium formate. 4-Methyl-α-undecylbenzylamine is prepared by condensing palm fatty acid with toluene to give 4-methyllauroylbenzene and heating the latter with ammonium formate. Samples have been furnished under Sect. 2 (5) of salts prepared by treating α-undecylbenzylamine with hydrochloric, lactic and citric acids and N-dimethyl-α-undecylbenzylamine with hydrochloric acid. The Specification as open to inspection under Sect. 91 comprises also the treatment of the aralkylamines with sulphocarboxylic acid halides of the aliphatic and aromatic series and also with sulphoalkyl and sulphoaralkyl alcohols. Treatment with chloracetone and chloracetophenone is mentioned. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH536881X | 1938-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB536881A true GB536881A (en) | 1941-05-30 |
Family
ID=4518826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30704/39A Expired GB536881A (en) | 1938-11-25 | 1939-11-24 | Process for the production of water-soluble high molecular ª‡-substituted aralkyl amines and derivatives thereof, and the resulting products |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB536881A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2597247A (en) * | 1948-08-02 | 1952-05-20 | Smith Kline French Lab | Nu-substituted amino-ethanols |
| US2597248A (en) * | 1948-08-06 | 1952-05-20 | Smith Kline French Lab | Nu-substituted amino-ethanols |
| US2600301A (en) * | 1948-06-04 | 1952-06-10 | Smith Kline French Lab | N-substituted-beta halo-ethyl amines |
| US2812351A (en) * | 1953-05-18 | 1957-11-05 | Lab Laboz Soc D | Method of preparing butylamines-2 disubstituted in 4-position by hydroxylated aromatic radicals |
| US2993894A (en) * | 1958-12-24 | 1961-07-25 | Union Carbide Corp | Pyrenes and process for their preparation |
| US3133967A (en) * | 1960-02-04 | 1964-05-19 | Boehringer Sohn Ingelheim | 1-(3, 4-dialkoxy-phenol)-1-dialkylamino-3-and-4-piienyl butanes |
| US4822914A (en) * | 1978-10-05 | 1989-04-18 | Hoechst-Roussel Pharmaceuticals, Inc. | 2-amino-N-methyl-α-phenyl-phenethylamines |
| US5185465A (en) * | 1978-10-05 | 1993-02-09 | Hoechst-Roussel Pharmaceuticals Inc. | Carboxamides of 2-amino-alpha-phenlphenethylamines |
| US5260339A (en) * | 1978-10-05 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | 4-phenyl-1,3-benzodiazepines and 2-amino-α-phenylphenethylamines for treating convulsions and protecting neurons |
-
1939
- 1939-11-24 GB GB30704/39A patent/GB536881A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600301A (en) * | 1948-06-04 | 1952-06-10 | Smith Kline French Lab | N-substituted-beta halo-ethyl amines |
| US2597247A (en) * | 1948-08-02 | 1952-05-20 | Smith Kline French Lab | Nu-substituted amino-ethanols |
| US2597248A (en) * | 1948-08-06 | 1952-05-20 | Smith Kline French Lab | Nu-substituted amino-ethanols |
| US2812351A (en) * | 1953-05-18 | 1957-11-05 | Lab Laboz Soc D | Method of preparing butylamines-2 disubstituted in 4-position by hydroxylated aromatic radicals |
| US2993894A (en) * | 1958-12-24 | 1961-07-25 | Union Carbide Corp | Pyrenes and process for their preparation |
| US3133967A (en) * | 1960-02-04 | 1964-05-19 | Boehringer Sohn Ingelheim | 1-(3, 4-dialkoxy-phenol)-1-dialkylamino-3-and-4-piienyl butanes |
| US4822914A (en) * | 1978-10-05 | 1989-04-18 | Hoechst-Roussel Pharmaceuticals, Inc. | 2-amino-N-methyl-α-phenyl-phenethylamines |
| US5185465A (en) * | 1978-10-05 | 1993-02-09 | Hoechst-Roussel Pharmaceuticals Inc. | Carboxamides of 2-amino-alpha-phenlphenethylamines |
| US5260339A (en) * | 1978-10-05 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | 4-phenyl-1,3-benzodiazepines and 2-amino-α-phenylphenethylamines for treating convulsions and protecting neurons |
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