DE1493814A1 - Use of aminocarboxylic acids as viscosity-increasing agents - Google Patents
Use of aminocarboxylic acids as viscosity-increasing agentsInfo
- Publication number
- DE1493814A1 DE1493814A1 DE19631493814 DE1493814A DE1493814A1 DE 1493814 A1 DE1493814 A1 DE 1493814A1 DE 19631493814 DE19631493814 DE 19631493814 DE 1493814 A DE1493814 A DE 1493814A DE 1493814 A1 DE1493814 A1 DE 1493814A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- propyl
- viscosity
- acid
- dodecyl
- 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.)
- Granted
Links
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title description 9
- 239000003795 chemical substances by application Substances 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- -1 n-ptntyl Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- DNFJICISVQDPEL-UHFFFAOYSA-N ethyl 2-cyanotetradecanoate Chemical compound CCCCCCCCCCCCC(C#N)C(=O)OCC DNFJICISVQDPEL-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/06—Solidifying liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Description
Aktraseloheoi 8 50,970 Ifb/12 q RAU 4101/6Aktraseloheoi 8 50,970 Ifb / 12 q RAU 4101/6
U938UU938U
g τοπ AwlnoonrbomiSurm g τοπ AwlnoonrbomiSu rm
MIttelMiddle
Di· τοτ11·β·ηι5· SrfiaduB« bttrif ft dl« »Vtrvtodune von d«r «Ugtaitliitii FormelDi · τοτ11 · β · ηι5 · SrfiaduB «bttrif ft dl« »Vtrvtodune from d «r« Ugtaitliitii formula
CH2HII2CH2HII2
worin R1 ·1η«η geeüttlgten Xohlenwae«*r9toffr*et alt tlner Ktttenläne· von nludeettn· 7 Kohltnetoffmtom·» and-It •ism eeeattletea, 1 ble 10 KohlenstoffatOM Kohl«nvaeo«ntoffr«t% btdtutta» •owl· το» Sftlmm «olcter Aalnooerboneeuren, al·where R 1 · 1η «η geeüttlgten Xohlenwae« * r9toffr * et old tlner Ktttenläne · from nludeettn · 7 Kohltnetoffmtom · »and-It • ism eeeattletea, 1 ble 10 carbon atoms Kohl« nvaeo «ntoffr« t% btdtutta » "Sftlmm" olcter Aalnooerboneeuren, al ·
28.10.68 . ; ■10/28/68. ; ■
BADBATH
909821/088^909821/088 ^
zweigte gesättigte Kohlenwasserstoffreste alt Xettenlängen von mindestens 7 Kohlenstoff atomen, vorzugsweise Alkylgruppen alt '· XettenlXngen von 8 bis 22 Kohlenetoffatomen. Beispiele Soloher Alkylgruppen sind! Ootyl, Nonyl, Decyl, Undeoyl, Dodeoyl, Tetrade oyl, Hexadeoyl, Ootadeoyl, Bloosyl, Dooosyl.branched saturated hydrocarbon radicals old xette lengths of at least 7 carbon atoms, preferably alkyl groups old ' Xettes lengths from 8 to 22 carbon atoms. Examples Soloher Are alkyl groups! Ootyl, Nonyl, Decyl, Undeoyl, Dodeoyl, Tetradeoyl, Hexadeoyl, Ootadeoyl, Bloosyl, Dooosyl.
Als Rj-Reste kommen verzweigte oder unverzweigte gesättigte Kohlenwasserstoffreste mit .Kettenlängen von 1 bis 10 Kohlenstoff -_ atomen in Betraoht. Bevorzugt bedeutet Ra eine niedere verzweigte . oder unverzweigte Alkylgruppe alt 1 bis 8 Kohlenstoffatomen, wie Methyl, Aethyl, Propyl, n-Butyl, Isobutyl, n-Ptntyl, Isoamyl, Hexyl, Hepty1, Ootyl. . . -The Rj radicals are branched or unbranched saturated hydrocarbon radicals with chain lengths of 1 to 10 carbon atoms. R a is preferably a lower branched one. or unbranched alkyl groups with 1 to 8 carbon atoms, such as methyl, ethyl, propyl, n-butyl, isobutyl, n-ptntyl, isoamyl, hexyl, heptyl, ootyl. . . -
Als Salze der erfindungsgeaäss erhältllohen Aminosäuren der Formel Z kommen infolge des amphoteren Charakters der Aalnoearbonsäuren sowohl innere Salze, als auch Salze alt Mineralsäuren, wie Salzsäure, Schwefelsäure und Phosphorsäure» sowie mit starken Al- >As salts of the amino acids according to the invention Due to the amphoteric character of the eel carboxylic acids, both internal salts and salts of mineral acids, such as Hydrochloric acid, sulfuric acid and phosphoric acid »as well as with strong Al->
kallen In Frage. . . 'kallen in question. . . '
bekannte Art (vgl. z.B. die britische Patentschrift No. 829,663)known species (see e.g. British patent specification No. 829,663) dadurch hergestellt werden', . ■are thereby produced ',. ■
dass man eine Verbindung der allgemeinen Formel 'that a compound of the general formula '
9096^217 bit 4 BAD 9096 ^ 217 bit 4 B AD
worin Rs eine veresterte Carboxylgruppe, R1' einen gesättigten oder ungesättigten Kohlenwasserstoffrest mit einer Kettenlänge von mindestens 7 Kohlenstoffatomen und R2 1 einen gesättigten oder ungesättigten, 1 bis 10 Kohlen- .z · stoffatome enthaltenden Kohlenwasserstoffrest bedeuten, einerseits zwecke üeberführung der Cyan- in die Aminomethylgruppe mit einem Reduktionsmittel und andererseits zwecks Freisetzung der veresterten Carboxylgruppe mit einem hydrolysierenden Mittel behandelt und erhaltene Aminocarbonsäuren der Formel I gegebenenfalls In ein Salz überführt.where Rs is an esterified carboxyl group, R 1 'is a saturated or unsaturated hydrocarbon radical with a chain length of at least 7 carbon atoms and R 2 1 is a saturated or unsaturated hydrocarbon radical containing 1 to 10 carbon atoms , on the one hand for purposes of converting the cyanide the aminomethyl group is treated with a reducing agent and, on the other hand, with a hydrolyzing agent in order to liberate the esterified carboxyl group, and the aminocarboxylic acids of the formula I obtained are optionally converted into a salt.
Die beiden zur Üeberführung der Ausgangsstoffe der Formel II in die Endprodukte der Formel I notwendigen Operationen, nämlich die Reduktion der Cyangruppe einerseits und die Hydrolyse der veresterten Carboxylgruppe andrerseits, können in beliebiger Reihenfolge vorgenommen werden. Nach einer bevorzugten Ausführungsart des erflndungsgemässen Verfahrens reduziert man zunächst die Cyangruppe zur Aminomethylgruppe und hydrolysiert hierauf die ver- * esterte Carboxylgruppe»The two for transferring the starting materials of the formula II operations necessary in the end products of formula I, namely the reduction of the cyano group on the one hand and the hydrolysis of the esterified On the other hand, the carboxyl group can be carried out in any order. According to a preferred embodiment of the According to the method according to the invention, the cyano group is first reduced to the aminomethyl group and then hydrolyzes the esterified carboxyl group »
Für die Reduktionsoperation kommen die für die Reduktion von Cyancarbonsäuren bzw.-carbonsäureestern zu den entsprechenden . Aminocarbonsäuren bzw.-carbonsäureestern üblicherweise verwendeten Reduktionsmittel in Frage, insbesondere·katalytisch aktivierter Wasserstoff. Als Katalysatoren seien genannt: Platin-, Palladium-For the reduction operation, those for the reduction of cyanocarboxylic acids or carboxylic acid esters are added to the corresponding ones. Aminocarboxylic acids or aminocarboxylic acid esters usually used reducing agents in question, in particular catalytically activated ones Hydrogen. The following catalysts may be mentioned: platinum, palladium
BAD ORIGINAL 909821/0884BATH ORIGINAL 909821/0884
t » ' ITt »'IT
■;-*-■■■ U938U■; - * - ■■■ U938U
oder Nickelkatalysatoren, insbesondere Raney-Nickel. Auch Raney-Kobalt kommt in Betracht. Die katalytisch« Reduktion kann mit oder ohne Anwendung von Ueberdruok durchgeführt werden, wobei die Verwendung eines Lösungsmittels, wie eines Alkohols, insbesondere Aethyl- oder Methylalkohol, zweokmässig ist. Bevorzugt verwendet man den der Estergruppe entsprechenden Alkohol. Der Reaktionsverlauf ist in der Regel sehr einheitlich, indem die Oyangruppe praktisch ausschliesslioh zur primären Aminogruppe reduziert wird. Die unerwünschte Bildung von Hydrierungsprodukten mit sekundären oder tertiären Aminogruppen kann erforderlichenfalls auf an sich bekannte Weise durch Hydrierung in Gegenwart von Ammoniak hintangehalten werden.or nickel catalysts, especially Raney nickel. Raney cobalt too is concerned. The catalytic reduction can be done with or be carried out without the use of Ueberdruok, the Use of a solvent such as an alcohol, in particular ethyl or methyl alcohol, is two-fold. Used with preference the alcohol corresponding to the ester group. The course of the reaction is usually very uniform by the oyan group is reduced practically exclusively to the primary amino group. The undesirable formation of hydrogenation products with secondary or tertiary amino groups may, if necessary, on per se known way be prevented by hydrogenation in the presence of ammonia.
Zn Ausgangsmaterial gegebenenfalls vorhandene ungesättigte Ri'-bzw« Ra'-Substituenten werden im Zuge der Hydrierungsoperation zu den entsprechenden gesättigten Substituenten Rx bzw. R2 hydriert. so z.B. eine Allyl- zur n-Propylgruppe, eine Methallyl- zur Isobutylgruppe, eine 7,7-Dimethallyl- zur Isoamylgruppe.Any unsaturated Ri 'or «Ra' substituents present in the starting material are hydrogenated to the corresponding saturated substituents R x or R 2 in the course of the hydrogenation operation. for example an allyl group to the n-propyl group, a methallyl group to the isobutyl group, a 7,7-dimethallyl group to the isoamyl group.
". Die Hydrolyse der veresterten Carboxylgruppe zur freien Carboxylgruppe kann auf an sich bekannte Art vorgenommen werden. Als hydrolysierende Mittel können Säuren oder Alkalien verwendet werden. Zweckmässig wird einer Lösung des Esters in Aethylalkohol eine Lösung eines Alkalihydroxyds, wie Natrium- oder Kaliumhydroxyd, in Wasser zugeführt und das Gemisch unter Rückfluss gekocht.". The hydrolysis of the esterified carboxyl group to the free Carboxyl group can be made in a manner known per se. Acids or alkalis can be used as the hydrolyzing agent. A solution of the ester in ethyl alcohol is expedient a solution of an alkali hydroxide, such as sodium or potassium hydroxide, fed in water and the mixture refluxed.
909821/0884909821/0884
BAD ORIGINALBATH ORIGINAL
L IL I
k j ι tk j ι t
CbVi ■ CbVi ■
14938U14938U
Die als Ausgangstoffe verwendeten Verbindvmgen der Formel II können aus Cyanessigester leicht wie folgt erhalten werden: Das Natriumsalz des Cyanessigesters wird in Gegenwart von überschüssigen Cyanessigester in Alkohol mit einem R1'-Halogenid, z.B. Dodeeylbromid, umgesetzt. In die erhaltenen mqnosubstituierten Cyanessigester. kann hierauf auf entsprechende Art ein zweiter Sübstituent.eingeführt werden, z.B* eine Allylgruppe durch Umsetzung mit Allylbromid.The compounds of formula II used as starting materials can easily be obtained from cyanoacetate as follows: The sodium salt of the cyanoacetate is reacted in alcohol with an R 1 'halide, for example dodecyl bromide, in the presence of excess cyanoacetate. In the mqnosubstituted cyanoacetic esters obtained. can then be introduced in a corresponding manner, eg * an allyl group by reaction with allyl bromide.
Die Aminocarbonsäuren der Formel I sind kristalline, in Wasser, kaltem Aethanol, Methanol oder Isopropanol sehr wenig lösliche Verbindungen. Ihr Schmelzpunkt ist, da stark von der Auf-The aminocarboxylic acids of the formula I are crystalline, in Water, cold ethanol, methanol or isopropanol very little soluble compounds. Its melting point is, as it is strongly
i heizgesehwlndigkeit abhängig, wenig charakteristisch. Meist sintern \ i dependent on the sensitivity to heating, not very characteristic. Mostly sinter \
die Verbindungen bis 10 vor dem eigentlichen Schmelzen. Die Verbindungen ertragen in Substanz Temperaturen von mehr als 50°C während kurzer Zeit. Beim Erhitzen auf 1000C und darüber entstehen klebrige Polymerisate.the connections to 10 before the actual melting. In substance, the compounds can withstand temperatures of more than 50 ° C for a short time. When heated to 100 ° C. and above, sticky polymers are formed.
Die Aminocarbonsäuren der Formel I wirkenThe aminocarboxylic acids of the formula I are effective
viskositätserhöhend. Insbesondere vermögen sie unpolare bzw. wenig polare organische Lösungsmittel, wie aliphatische Kohlenwasserstoffe, z.B. Benzin; Petroläther Jeglichen Siedebereichs; halogenierte aliphatische und aromatische Kohlenwasserstoffe, wie Methylenchlorid, Chloroform,Tetrachlorkohlenstoff;aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol; nitrierte Kohlenwasserstoffe, wie Nitrobenzol; Aether, wie Diäthylä,ther, Dloxan etc zuviscosity increasing. In particular, they are capable of non-polar or little polar organic solvents such as aliphatic hydrocarbons, e.g., gasoline; Petroleum ether of any boiling range; halogenated aliphatic and aromatic hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride; aromatic hydrocarbons, such as benzene, toluene, xylene; nitrated hydrocarbons such as nitrobenzene; Ethers such as diethyl ether, dloxan etc.
909821/0684909821/0684
> J Λ> J Λ
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"6" U93814" 6 " U93814
Gelen zu verdicken. Ein deutlicher viskositätserhöhender Effekt ist bereits bei Konzentrationen (Gewicht/Volumen) in der Grössenordnung von 1 Promille zu beobachten. Für praktische Zwecke wird meist eine Konzentration in der Grössenordnung von rund 0,5 bis einigen wenigen Prozent genügen.Thicken gels. A clear viscosity-increasing effect is even at concentrations (weight / volume) in the order of magnitude from 1 per mille to be observed. For practical purposes, a concentration of around 0.5 to a few percent suffice.
In Form der mineralsauren Salze, wie des Hydrochloride, haben die Verfahrensprodukte einen gelierenden Effekt auch auf Wasser.In the form of mineral acid salts, such as the hydrochloride, the process products also have a gelling effect Water.
Die Viskosität der erhaltenen Lösungen bzw. Gele ist in der Regel nur wenig temperaturabhängig.The viscosity of the solutions or gels obtained is generally only slightly dependent on temperature.
Der Verdlokungseffekt der erfindungsgemäss erhältlichen Aminocarbonsäuren kann durch Zugabe geeigneter Mittel, z.B. von 2-Amlno-2-methyl-propandlol-(1,3)* aufgehoben werden.The thickening effect obtained according to the invention Aminocarboxylic acids can be abolished by adding suitable agents, e.g. 2-Amlno-2-methyl-propandlol- (1,3) *.
In wenig polaren oder unpolaren, tiefsiedenden organischen Lösungsmitteln entfalten die Verfahrensprodukte ihren gelierenden Effekt zum Teil erst nach längerm Kochen. Um in solchen Fällen rasoh zu einem Gel zu kommen, empfiehlt sich folgendes Vorgehen: Das kristalline Verdickungsmittel wird In Benzol kurz aufgekocht, wobei ein klares Gel entsteht. Dieses Gel wird dann unter vermindertem Druck bei etwa 4O-6O°C eingedampft. Man erhält so ein amorphes Produkt mit erhöhter Gelierfähigkeit, das nun auch andere Lösungsmittel sehr rasch, z.B. bereits nach kurzem Aufkochen, zumThe process products develop their gelling properties in slightly polar or non-polar, low-boiling organic solvents The effect is partly only after a long period of cooking. In order to get a gel in such cases, the following procedure is recommended: The crystalline thickener is briefly boiled in benzene to form a clear gel. This gel is then reduced under Pressure evaporated at about 40-60 ° C. You get one like that amorphous product with increased gelling ability, this now also different Solvent very quickly, e.g. after boiling for a short time, for
909821/0884909821/0884
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, Aufgrund ihrer Viskositätserhöhenden Wirkung können die |, Due to their viscosity-increasing effect, the |
Aminocarbonsäuren der Formel I als Verdickungs- bzw. Geliermittel '' auf den verschiedensten Gebieten Verwendung finden, z.B. als Verdiokungs- bzw. Geliermittel für unpolare bzw. wenig polare organisohe Lösungsmittel in der pharmazeutischen und kosmetischen Industrie; ferner für Druckfarben, Anstrichfarben, Lacke, Schmieröle, Fleckenreinigungsmittel etc.For amino carboxylic acids of formula I as thickening or gelling agents '' in various fields use, eg as Verdiokungs- or gelling agent for non-polar or slightly polar organisohe solvent in the pharmaceutical and cosmetic industries; also for printing inks, paints, varnishes, lubricating oils, spot cleaners, etc.
Im folgenden werden einige Anwendungsmöglichkeiten beschrieben ιSome possible applications are described below ι
a) 1-10 g a-n-Hexadecyl-a-propyl-ß-amino-propionsäure werden in 1000 g dünnflüssigem Paraffinöl unter Rühren solange erwärmt, bis die Lösung vollkommen klar ist. Das so erhaltene viskose OeI eignet sich z.B. für Schmierzwecke. a) 1-10 g of an-hexadecyl-a-propyl-ß-amino-propionic acid are heated in 1000 g of low-viscosity paraffin oil with stirring until the solution is completely clear. The viscous oil obtained in this way is suitable, for example, for lubricating purposes.
b) Eine thixotrope Grundmasse für Lacke und Farben kann wie folgt erhalten werden: 10 g a-n-Dodecyl-a-propyl-ß-araino-propionsäure werden in 1000 g Petroläther erwärmt. Man erhält eine gallertartige, zähflüssige Masse, in der geeignete Lackrohstoffe und Farben eingearbeitet werden können. Diese Lacke und Farben fHessen aus Behältern, wie z.B. Tuben, nicht aus, haften am Pinsel, lassen sich aber leicht verstreichen.b) A thixotropic base material for lacquers and paints can be obtained as follows: 10 g of an-dodecyl-a-propyl-ß-araino-propionic acid are heated in 1000 g of petroleum ether. A gelatinous, viscous mass is obtained in which suitable paint raw materials and colors can be incorporated. These varnishes and paints do not leak out of containers such as tubes, stick to the brush, but can be easily spread.
Die folgenden Beispiele beziehen sich auf die SyntheseThe following examples relate to synthesis
von Verbindungen der Formel I: ■of compounds of the formula I: ■
909821/0884909821/0884
BAD ORIGINALBATH ORIGINAL
1 t 11 * t1 t 11 * t
1 · · > 11 11 ·> 11 1
It Ϊ 1 * 1It Ϊ 1 * 1
a) ΙΟ9Ο g n-Dodecyl-allyl-cyanessigsäureäthylester In 500 ml absolutem Alkohol werden ifc Gegenwart von 200 g Raney-Nickel In einem Rührautoklaven bei 80°C und unter 70 atti Wasserstoff hydriert. Nach beendigter Wasserstoffaufnahme wird das Reaktionsprodukt filtriert, die nach der Filtration anfallende Lösung unter vermindertem Druck eingedampft und der Eindampfrückstand ansohllessend im Hochvakuum destilliert. Der erhaltenea) ΙΟ9Ο g of ethyl n-dodecyl-allyl-cyanoacetate In 500 ml of absolute alcohol are ifc the presence of 200 g of Raney nickel In a stirred autoclave at 80 ° C and below 70 atti hydrogen hydrogenated. After the uptake of hydrogen is complete The reaction product is filtered, the solution obtained after the filtration is evaporated under reduced pressure and the evaporation residue ansohllessend distilled in a high vacuum. The received
. a-n-Dodecyl-a-propyl-ß-amino-propionsäureäthylester destilliert als farblose Flüssigkeit bei l60°C/0,15 mm über. Ausbeute 7856 der Theorie.. a-n-Dodecyl-a-propyl-ß-amino-propionic acid ethyl ester distilled as colorless liquid at 160 ° C / 0.15 mm above. Yield 7856 of the Theory.
b) 687 g des erhaltenen a-n-Dodecyl-a-propyl-ß-aminopropionsäureäthylesters werden in 38ΟΟ ml Aethylalkohol gelöst. Dann fügt man eine Lösung von 235 S Kaliumhydroxyd in 240 ml destilliertem Wasser zu. Die klare Lösung wird 24 Stunden unter Rückfluss gekocht. Dann werden ca. 2000 ml Alkohol abdestilliert und der Rückstand anschliessend mit ca. 2 kg Eis versetzt. Die entstehende klare Lösung wird mit Eisessig auf ein pH von 5-6 gebracht. Dabei fällt die rohe a-n-Dodecyl-a-propyl-ß-amino-propionsäure als guomiartige krümelige Masse aus. Diese wird abgesaugt und gut mit Wasser gewaschen. Der Filtrationsrückstand wird in ca. 3000 ml . Isopropanol gelöst und die Lösung heiss filtriert. Das heisse FiIrtrat wird mit ca. 750 ml destilliertem Wasser versetzt und die entstehende Fällung durch weiteres Erhitzen gelöst. Man lässt nunb) 687 g of the a-n-dodecyl-a-propyl-ß-aminopropionic acid ethyl ester obtained are dissolved in 38ΟΟ ml of ethyl alcohol. A solution of 235 S potassium hydroxide in 240 ml of distilled water is then added Water too. The clear solution is refluxed for 24 hours. Then about 2000 ml of alcohol are distilled off and about 2 kg of ice are then added to the residue. The resulting clear solution is brought to a pH of 5-6 with glacial acetic acid. The crude a-n-dodecyl-a-propyl-ß-amino-propionic acid falls as guomi-like crumbly mass. This is suctioned off and washed well with water. The filtration residue is in approx. 3000 ml. Isopropanol dissolved and the solution filtered while hot. The hot council 750 ml of distilled water are added and the resulting precipitate is dissolved by further heating. One lets now
909821/0884 bad original909821/0884 bathroom original
I *I *
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bei Zimmertemperatur stehen bis der Ansatz etwa 3O0C erreicht hat und stellt dann über Nacht in den Eisschrank, ßie-auskristallisierte a-n-Dodecyl-a-propyl-ß-amino-propionsKure wird ab- ■ jstand at room temperature until the batch about 3O 0 C has reached and then provides overnight in the refrigerator, sYou-crystallized by-dodecyl-a-propyl-.beta.-amino-propionsKure is off ■ j
gesaugt, mit kaltem Isopropanol gewaschen und möglichst weitgehend trocken gepresst. Das Produkt wird vorerst bei Zimmertemperatur im Vakuumtrockenschrank getrocknet bis es äusserlich trocken ist und dann bei maximal 50°C über Phosphorpentoxyd und Kaliumhydroxyd bis zur Gewichtskonstanz weiter getrocknet. Ausbeute 90$ der Theorie.sucked, washed with cold isopropanol and as much as possible pressed dry. The product is first dried in a vacuum drying cabinet at room temperature until it is externally dry and then at a maximum of 50 ° C over phosphorus pentoxide and potassium hydroxide Further dried to constant weight. Yield $ 90 the theory.
Die so in Form eines welssen bis leicht gelben Pulvers erhaltene a-n-Dodecyl-a-propyl-ß-amino-propionsäure schmilzt bei i etwa 2390C unter Zersetzung. !The an-dodecyl-α-propyl-β-aminopropionic acid thus obtained in the form of a white to slightly yellow powder melts at about 239 ° C. with decomposition. !
Der als Ausgangsstoff verwendete n-Dodecyl-aHyl-cyanessigsäureäthylester kann wie folgt erhalten werden:The ethyl n-dodecyl-aHyl-cyanoacetate used as the starting material can be obtained as follows:
0) In eine Lösung von 92 g Natrium in I600 ml absolutem Aethylalkohol gibt man bei ca.700C unter Rühren 9OO g Cyanesslgsäureäthylester. Während der Zugabe oder kurz danach fällt das Natriumsalz des Cyanessigesters aus. Nun wird der Ansatz zum Rückfluss erhitzt. Bei ca. 8o°C (innen) beginnt man unter Rühren mit dem .Zutropfen von 1000 g n-Dodecylbromld. Anschliessend wird unter ] Rückfluss gekocht, bis ein pH von 7-8 erreicht ist. Der Alkohol wird unter vermindertem Druck abdestilliert und der Rüokstand nach · Kühlen auf ca. 300C (innen) in 1000 ml Aether, 500 ml Wasser und0) In a solution of 92 g of sodium in 1600 ml of absolute ethyl alcohol are added at about 70 0 C with stirring 9OO g of ethyl cyanoate. During the addition or shortly afterwards, the sodium salt of the cyanoacetic ester precipitates out. The batch is now heated to reflux. At approx. 80 ° C (inside), the addition of 1000 g of n-dodecyl bromide is started while stirring. It is then refluxed until a pH of 7-8 is reached. The alcohol is distilled off under reduced pressure and the Rüokstand according · cooling to about 30 0 C (internal) in 1000 ml of ether, 500 ml of water and
BAD ORIGINAL 909821/0884BATH ORIGINAL 909821/0884
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11 tt ■ ■ 1■ ■ 1 >'> '
1 1.11 1.1 ' i >'i>
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titi * t* t 1111
- 10 -- 10 -
oa. $QQ g Eis gelöst, ausgerührt und abgetrennt. Die wässrige Phase wird noch 2 mal mit 500 ml Aether ausgezogen. Die vereinigten Aetherauszüge werden mit Wasser und mit gesättigter Natriumchloridlösung gewaschen, getrocknet und eingedampft. Im Wasserstrahlvakuum wird dann bei einer Badtemperatur von l6o°C die Hauptmenge des überschüssigen Cyanesslgesters abdestilliert, dann lässt man auf ca. 50 C (innen) abkühlen und destilliert anschliessend Im Hochvakuum noch kleine Mengen Cyanessigester und den weitern Vorlauf. Der n-Dodecylcyanessigsäureäthylester geht bei 142-145°C/0,05-0,1 mm als farblose Flüssigkeit über. Ausbeute 79$·oa. $ QQ g of ice dissolved, stirred up and separated off. The aqueous phase is extracted twice with 500 ml of ether. The combined ether extracts are washed with water and with saturated sodium chloride solution, dried and evaporated. The bulk of the excess cyanoacetic ester is then distilled off in a water jet vacuum at a bath temperature of 160 ° C., then allowed to cool to approx. 50 ° C. (inside) and then small amounts of cyanoacetic ester and the remaining flow are distilled in a high vacuum. The ethyl n-dodecylcyanoacetate passes over as a colorless liquid at 142-145 ° C./0.05-0.1 mm. Yield $ 79
Den erhaltenen n-Dodecylcyanessigsäureäthylester gibt man unter Rühren bei ca.6O-7O°C.zu einer Lösung von 72,8 g Natrium in 1260 ml absolutem Aethylalkohol. Dabei fällt das Natriumsalz des n-Dodecyloyanessigsäureäthylesters aus. Anschliessend tropft man unter Rühren 458 g Allylbromid so zu, dass die Reaktionsmischung leicht zum Sieden kommt. Nach der Zugabe wird solange unter Rückfluss erhitzt (Badtemperatür HO0C), bis ein pH von 7-8 erreicht ist.. Der Alkohol wird nun unter vermindertem Druck abdestilliert und der Rückstand wie vorstehend beschrieben aufgearbeitet. Bei der absohllessenden Destillation im Hochvakuum erhält man den n-Dodecylallyl-cyanessigsäureäthylester (Siedebereich 135-1^O°C/O,O3 mm) als farblose Flüssigkeit in einer Ausbeute vonThe resulting ethyl n-dodecylcyanoacetate is added with stirring at about 60-70 ° C. to a solution of 72.8 g of sodium in 1260 ml of absolute ethyl alcohol. The sodium salt of the ethyl n-dodecyloyaneacetate precipitates. Then 458 g of allyl bromide are added dropwise with stirring in such a way that the reaction mixture easily comes to the boil. After the addition, the mixture is heated under reflux (bath temperature HO 0 C) until a pH of 7-8 is reached. The alcohol is now distilled off under reduced pressure and the residue is worked up as described above. The absolute distillation in a high vacuum gives the ethyl n-dodecylallyl cyanoacetate (boiling range 135-1 ^ O ° C / O, O3 mm) as a colorless liquid in a yield of
909821/0884909821/0884
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' Beispiel 2 ' Example 2
Durch Hydrierung von n-Octyl-allyl-cyanessigsäureäthylester und anschllessende Hydrolyse des erhaltenen α-n-OetylrCxpropyl-ß-amino-propionsäureäthylesters auf die vorstehend beschriebene Art erhält man die a-n-Octyl-a-propyl-ß-amino-propion-Bäure. Schmelzpunkt ca.238 C(unter Zersetzung}; Ausbeute 72$ (bezogen auf den n-Octyl-allyl-cyanessigsäureester).Hydrogenation of n-octyl-allyl-cyanoacetic acid ethyl ester and subsequent hydrolysis of the resulting α-n-ethyl / hydroxpropyl-ß-aminopropionic acid ethyl ester in the manner described above gives an-octyl-α-propyl-ß-aminopropionic acid. Melting point about 238 C (with decomposition); yield $ 72 (based on the n-octyl-allyl-cyanoacetic acid ester).
Durch Hydrierung von n-Decyl-allyl-cyanessigsäureäthylester und anschllessende Hydrolyse des erhaltenen a-n-:Decyl-apropyl-ß-amino-propionsäureäthylesters auf die vorstehend be- j sohriebene Art, erhält man die a-n-Decyl-a-propyl-ß-aminopropionsäure; Schmelzpunkt ca. 2380C (unter Zersetzung); Ausbeute 70-75$ (bezogen auf den n-Decyl-allyl-cyanessigsäureester).Hydrogenation of ethyl n-decyl-allyl-cyanoacetate and subsequent hydrolysis of the ethyl an-: decyl-apropyl-ß-aminopropionate obtained in the manner described above gives an-decyl-a-propyl-ß-aminopropionic acid ; Melting point approx. 238 ° C. (with decomposition); Yield $ 70-75 (based on the n-decyl-allyl-cyanoacetic acid ester).
: i: i
Durch Hydrierung von n-Tetradecyl-allyl-cyanessigsäureäthylester und anschliessende Hydrolyse.des erhaltenen a-n-Tetradecyl-a-pröpyl-ß-amino-propionsäureäthylesters auf die vorstehend beschriebene Art, erhält man die on-Tetradecyl-a-propyl-ß-aminopropionsäure. Schmelzpunkt ca. 240°C (unter Zersetzung); Ausbeute 65$ (bezogen auf den n-Tetradecyl-allyl-cyanessigsäureester).By hydrogenation of n-tetradecyl-allyl-cyanoacetic acid ethyl ester and subsequent hydrolysis of the a-n-tetradecyl-a-propyl-ß-amino-propionic acid ethyl ester obtained on-tetradecyl-a-propyl-ß-aminopropionic acid is obtained in the manner described above. Melting point approx. 240 ° C (with decomposition); Yield $ 65 (based on the n-tetradecyl-allyl-cyanoacetic acid ester).
90982 1/0884 bad orig.nal90982 1/0884 bad orig.nal
H938UH938U
Durch Hydrierung von n-Hexadecyl-allyl-cyanessigsäureäthylester und anschliessende Hydrolyse des erhaltenen a-n-Hexadecyl-cx-propyl-ß-amino-propionsäureäthylesters auf die vorstehend beschriebene Art erhält man die a-n-Hexadecyl-ct-propyl-ß-aminopropionsäure. Schmelzpunkt ca. 2360C(unter Zersetzung); Ausbeute 65$ (bezogen auf den n-Hexadecyl-allyl-cyanessigsäureester).Hydrogenation of ethyl n-hexadecyl-allyl-cyanoacetate and subsequent hydrolysis of the ethyl an-hexadecyl-cx-propyl-ß-amino-propionate obtained in the manner described above gives an-hexadecyl-ct-propyl-ß-aminopropionic acid. Melting point approx. 236 ° C. (with decomposition); Yield $ 65 (based on the n-hexadecyl-allyl-cyanoacetic acid ester).
Durch Hydrierung von n-Tetradecyl-methallyl-cyanessigsäureäthylester (Siedepunkt 154°/O>09 mm) und anschliessende Hydrolyse des erhaltenen a-n-Tetradecyl-a-isobutyl-ß-amino-propionsäureesters (Siedepunkt l63°/O,O4 mm) auf die beschriebene Art erhalt man a-n-Tetradecyl-a-isobutyl-ß-amino-propionsäure. Schmelzpunkt 217-2210C unter Zersetzung.By hydrogenation of n-tetradecyl-methallyl-cyanoacetic acid ethyl ester (boiling point 154 ° / O> 09 mm) and subsequent hydrolysis of the an-tetradecyl-α-isobutyl-ß-amino-propionic acid ester (boiling point 163 ° / O, 04 mm) to the The type described is obtained in-tetradecyl-a-isobutyl-ß-aminopropionic acid. Melting point 217-221 0 C with decomposition.
Dieses Produkt ist als Verdickungsmittel für unpolare organische Lösungsmittel besonders gut geeignet. Die entstehenden Lösungen bzw. Gele sind sehr homogen (wenig mizellbildend).This product is particularly suitable as a thickener for non-polar organic solvents. The emerging Solutions or gels are very homogeneous (little micelle-forming).
Durch Hydrierung von n-Dodecyl-methallyl-cyanessigsäureäthy!ester (Siedepunkt l40 - l45°/O>()7 _ q,08 mm) und an-By hydrogenation of n-dodecyl-methallyl-cyanoacetic acid ethyl ester (Boiling point l40 - l45 ° / E> () 7 _ q, 08 mm) and
909821/0884 „„.. 909821/0884 "" ..
' x>- U938H ' x > - U938H
schliessende Verseifung des erhaltenen α-n-Dodecyl-a-isobutylß-amino-propionskureesters (Siedepunkt l60°/0,2 mm) auf die beschriebene Art, erhält man a-n-Dodecyl-a-isobutyl-ß-amino-propionsäurej Schmelzpunkt 234 - 2360 unter Zersetzung.Final saponification of the α-n-dodecyl-a-isobutylß-amino-propionic acid ester (boiling point 160 ° / 0.2 mm) in the manner described gives an-dodecyl-a-isobutyl-ß-aminopropionic acid, melting point 234 - 236 0 with decomposition.
909821/0884909821/0884
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1507162A CH415667A (en) | 1962-12-21 | 1962-12-21 | Process for the preparation of aminocarboxylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1493814A1 true DE1493814A1 (en) | 1969-05-22 |
| DE1493814B2 DE1493814B2 (en) | 1973-03-15 |
| DE1493814C3 DE1493814C3 (en) | 1973-10-04 |
Family
ID=4406109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1493814A Expired DE1493814C3 (en) | 1962-12-21 | 1963-11-28 | Use of aminocarboxylic acids as viscosity-increasing agents |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3328436A (en) |
| BE (1) | BE641517A (en) |
| BR (1) | BR6355060D0 (en) |
| CH (1) | CH415667A (en) |
| DE (1) | DE1493814C3 (en) |
| DK (1) | DK123092B (en) |
| ES (1) | ES294734A1 (en) |
| GB (1) | GB992737A (en) |
| NL (2) | NL137819C (en) |
| SE (1) | SE318860B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3740421A (en) * | 1966-09-19 | 1973-06-19 | Basf Wyandotte Corp | Polyoxyethylene-polyoxypropylene aqueous gels |
| US3846458A (en) * | 1971-01-07 | 1974-11-05 | Us Agriculture | Arthropod maturation inhibitors |
| US4889646A (en) * | 1987-06-30 | 1989-12-26 | Amoco Corporation | Nitrogen containing dispersants treated with mineral acids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB601123A (en) * | 1945-03-16 | 1948-04-28 | James Lincoln | Improvements in the production of synthetic linear condensation polymers |
| GB792486A (en) * | 1954-12-23 | 1958-03-26 | Henkel & Cie Gmbh | A process for the production of ª‡-nitrilocarboxylic acid esters |
-
0
- NL NL302183D patent/NL302183A/xx unknown
- NL NL137819D patent/NL137819C/xx active
-
1962
- 1962-12-21 CH CH1507162A patent/CH415667A/en unknown
-
1963
- 1963-11-28 DE DE1493814A patent/DE1493814C3/en not_active Expired
- 1963-12-03 BR BR155060/63A patent/BR6355060D0/en unknown
- 1963-12-06 US US328483A patent/US3328436A/en not_active Expired - Lifetime
- 1963-12-13 GB GB49235/63A patent/GB992737A/en not_active Expired
- 1963-12-19 SE SE14203/63A patent/SE318860B/xx unknown
- 1963-12-19 DK DK592863AA patent/DK123092B/en unknown
- 1963-12-19 BE BE641517A patent/BE641517A/xx unknown
- 1963-12-20 ES ES294734A patent/ES294734A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL137819C (en) | |
| DE1493814C3 (en) | 1973-10-04 |
| GB992737A (en) | 1965-05-19 |
| CH415667A (en) | 1966-06-30 |
| DE1493814B2 (en) | 1973-03-15 |
| SE318860B (en) | 1969-12-22 |
| NL302183A (en) | |
| DK123092B (en) | 1972-05-15 |
| US3328436A (en) | 1967-06-27 |
| BE641517A (en) | 1964-06-19 |
| ES294734A1 (en) | 1964-06-01 |
| BR6355060D0 (en) | 1973-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |