JPWO2006075373A1 - β-alkoxypropionamides, solvents, detergents and liquid pharmaceutical compositions, and methods for producing β-alkoxypropionamides - Google Patents
β-alkoxypropionamides, solvents, detergents and liquid pharmaceutical compositions, and methods for producing β-alkoxypropionamides Download PDFInfo
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- JPWO2006075373A1 JPWO2006075373A1 JP2006552798A JP2006552798A JPWO2006075373A1 JP WO2006075373 A1 JPWO2006075373 A1 JP WO2006075373A1 JP 2006552798 A JP2006552798 A JP 2006552798A JP 2006552798 A JP2006552798 A JP 2006552798A JP WO2006075373 A1 JPWO2006075373 A1 JP WO2006075373A1
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- alkoxypropionamides
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- alkoxypropionamide
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- 239000002904 solvent Substances 0.000 title claims abstract description 35
- 239000007788 liquid Substances 0.000 title claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title abstract description 10
- 239000003599 detergent Substances 0.000 title abstract description 3
- 239000012459 cleaning agent Substances 0.000 claims abstract description 14
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- 229940079593 drug Drugs 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 abstract description 18
- 239000000126 substance Substances 0.000 abstract description 12
- 239000003905 agrochemical Substances 0.000 abstract description 8
- 239000012188 paraffin wax Substances 0.000 abstract description 4
- 230000007774 longterm Effects 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 150000003926 acrylamides Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 5
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- -1 methoxyethyl group Chemical group 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 2
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RESPXSHDJQUNTN-UHFFFAOYSA-N 1-piperidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCCC1 RESPXSHDJQUNTN-UHFFFAOYSA-N 0.000 description 1
- WLPAQAXAZQUXBG-UHFFFAOYSA-N 1-pyrrolidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCC1 WLPAQAXAZQUXBG-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 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
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- DLJMSHXCPBXOKX-UHFFFAOYSA-N n,n-dibutylprop-2-enamide Chemical compound CCCCN(C(=O)C=C)CCCC DLJMSHXCPBXOKX-UHFFFAOYSA-N 0.000 description 1
- RKSYJNCKPUDQET-UHFFFAOYSA-N n,n-dipropylprop-2-enamide Chemical compound CCCN(CCC)C(=O)C=C RKSYJNCKPUDQET-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 125000001117 oleyl 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])=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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本発明は、一般式(I)で表されるβ−アルコキシプロピオンアミド類、該アルコキシプロピオンアミド類を含有する溶剤および洗浄剤、特定のβ−アルコキシプロピオンアミド類に薬剤を溶解させた液状薬剤組成物、並びに塩基性触媒の存在下、アクリルアミドと脂肪族一価アルコールを反応させるβ−アルコキシプロピオンアミド類の製造方法であり、アミド系溶剤の溶解力を保持しつつパラフィン等にも溶解する優れた溶解力を有する溶剤および洗浄剤、或いは各種農業用薬剤を良く溶解し安全性や長期間の効果の持続する液状薬剤組成物、並びに該溶剤および洗浄剤を工業的に有利に製造する方法を提供する。【化1】The present invention relates to a β-alkoxypropionamide represented by the general formula (I), a solvent and a detergent containing the alkoxypropionamide, and a liquid drug composition in which a drug is dissolved in a specific β-alkoxypropionamide. And β-alkoxypropionamides that react acrylamide with an aliphatic monohydric alcohol in the presence of a basic catalyst, and are excellent in dissolving in paraffin and the like while retaining the solubility of amide solvents. Solvents and cleaning agents with dissolving power, or liquid pharmaceutical compositions that dissolve various agricultural chemicals well and maintain safety and long-term effects, and methods for industrially producing the solvents and cleaning agents are provided. To do. [Chemical 1]
Description
本発明は、β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法に関する。さらに詳しくは、新規なβ−アルコキシプロピオンアミド類を含有する溶剤、洗浄剤および液状薬剤組成物、並びにアクリルアミド類と脂肪族一価アルコールを温和な条件で反応させることにより、該β−アルコキシプロピオンアミド類を効率よく製造する方法に関する。 The present invention relates to β-alkoxypropionamides, solvents, detergents and liquid pharmaceutical compositions, and methods for producing β-alkoxypropionamides. More specifically, a solvent, a cleaning agent and a liquid pharmaceutical composition containing novel β-alkoxypropionamides, and reacting acrylamides with aliphatic monohydric alcohols under mild conditions, thereby allowing the β-alkoxypropionamides to react. The present invention relates to a method for efficiently producing products.
一般に、アミド系有機溶剤は、優れた溶解力と、水に容易に溶解する性質を有することから、水によるリンスが可能であり、溶剤又は洗浄剤として望ましい性能を有している。また、最近では、ハロゲン系溶剤がオゾン層を破壊するなど環境汚染をもたらすおそれがあることや毒性が大きいことから、アミド系溶剤は、従来のハロゲン系溶剤を代替する傾向にある。
このようなアミド系溶剤としては、例えばホルムアミド、N−モノメチルホルムアミド、N,N−ジメチルホルムアミド、N−モノエチルホルムアミド、N,N−ジエチルホルムアミド、アセトアミド、N、N−ジメチルアセトアミド、N−メチルピロリジノンなどが知られている。
このアミド系溶剤は、溶解性が優れていることから、殆どの溶剤および化合物を溶解し、洗浄剤としても好適に使用することができる。しかしながら、アミド系溶剤はパラフィン類との相溶性が無いので、その応用が大きく制限されている。
また、農薬製剤用溶剤としては、従来のアミド系溶剤は薬剤に対して優れた溶解性を有するものの、水溶性であるため雨水等により容易に散布した部位から溶出し、効果がすぐに消失する欠点があり、安全性や長期間の効果の持続が求められている。
洗浄剤としては、さらに沸点が高くて取り扱い易く、しかもその製造が容易な化合物も望まれている。In general, an amide organic solvent has excellent dissolving power and a property of being easily dissolved in water, so that it can be rinsed with water and has desirable performance as a solvent or a cleaning agent. In recent years, amide solvents tend to replace conventional halogen solvents because halogen solvents may cause environmental pollution such as destruction of the ozone layer and are highly toxic.
Examples of such amide solvents include formamide, N-monomethylformamide, N, N-dimethylformamide, N-monoethylformamide, N, N-diethylformamide, acetamide, N, N-dimethylacetamide, N-methylpyrrolidinone. Etc. are known.
Since this amide solvent is excellent in solubility, it can dissolve most solvents and compounds, and can be suitably used as a cleaning agent. However, since the amide solvent is not compatible with paraffins, its application is greatly limited.
In addition, as a solvent for agricultural chemicals, although conventional amide solvents have excellent solubility in drugs, they are soluble in water, so they are easily dissolved by rainwater, etc. There are drawbacks, and safety and long-lasting effects are required.
As a cleaning agent, a compound having a higher boiling point, easy to handle and easy to manufacture is also desired.
一方、アルコキシ基を有するアミドは、重合性モノマーとして用いるα,β−オレフィン系不飽和モノカルボン酸のN,N−ジアルキルアミドの製造法において、中間体としてβ−アルコキシ−N,N−ジアルキルプロピオンアミドが生成する。この中間体は、β−アルコキシプロピオン酸アルキルエステルとジアルキルアミンとを反応させてアミド化したものである。その反応は、例えばβ−メトキシ−N,N−ジメチルプロピオンアミドを製造する場合は、シールされた加圧ボンベ中で、しかも24〜40時間と長時間を要するので、これは経済的には不利な方法である(特許文献1参照)。 On the other hand, an amide having an alkoxy group is a β-alkoxy-N, N-dialkylpropion as an intermediate in the process for producing an N, N-dialkylamide of an α, β-olefin unsaturated monocarboxylic acid used as a polymerizable monomer. An amide is formed. This intermediate is amidated by reacting an alkyl ester of β-alkoxypropionic acid with a dialkylamine. For example, in the case of producing β-methoxy-N, N-dimethylpropionamide, this reaction is economically disadvantageous because it takes 24 to 40 hours in a sealed pressurized cylinder. (See Patent Document 1).
本発明の目的は、以上のような状況下で、アミド系溶剤の溶解力を保持しつつ、パラフィン等にも溶解する、優れた溶解力を有する溶剤および洗浄剤、或いは各種農業用薬剤を良く溶解し安全性や長期間の効果の持続する液状薬剤組成物を提供すること、並びに該溶剤および洗浄剤を工業的に有利に製造する方法を提供することである。 The object of the present invention is to provide a solvent and a cleaning agent having excellent dissolving power, or various agricultural chemicals that dissolve in paraffin and the like while retaining the dissolving power of the amide solvent under the above circumstances. It is to provide a liquid pharmaceutical composition that dissolves and maintains safety and long-term effects, and to provide a method for industrially advantageously producing the solvent and the cleaning agent.
本発明者は、上記課題を解決するために鋭意研究を重ねた結果、アクリルアミド類と脂肪族一価アルコールを反応させて得られるβ−アルコキシプロピオンアミド類がアミド系溶剤の溶解力を保持しつつパラフィン等にも溶解するので溶剤および洗浄剤として極めて有用であること、また特定のβ−アルコキシプロピオンアミド類が水に溶解しないことから農薬に用いれば安全性や長期間の効果の持続することができること、並びに塩基性触媒の存在下でアクリルアミド類と脂肪族一価アルコールを反応させることにより、温和な条件でβ−アルコキシプロピオンアミド類を効率良く製造できることを見出し、本発明に到達した。 As a result of intensive studies to solve the above problems, the present inventor has found that β-alkoxypropionamides obtained by reacting acrylamides with aliphatic monohydric alcohols retain the solubility of amide solvents. It is also very useful as a solvent and cleaning agent because it dissolves in paraffin and the like, and since certain β-alkoxypropionamides do not dissolve in water, they can be used safely in agrochemicals and have long-lasting effects. It has been found that β-alkoxypropionamides can be efficiently produced under mild conditions by reacting acrylamides and aliphatic monohydric alcohols in the presence of a basic catalyst.
すなわち、本発明は、
(1)、一般式(I)で表されるβ−アルコキシプロピオンアミド類、That is, the present invention
(1), β-alkoxypropionamides represented by the general formula (I),
(式中、R1は炭素数3〜18のアルキル基、R2およびR3はそれぞれ独立に水素原子又は炭素数1〜6のエーテル結合を有しても良い炭化水素基であり、互いに同一であっても異なっていてもよく、さらに互いに結合して環構造を形成してもよい。)
(2)、R2およびR3がメチル基である上記(1)のβ−アルコキシプロピオンアミド類、
(3)、上記(1)又は(2)のβ−アルコキシプロピオンアミド類を含有することを特徴とする溶剤、
(4)、上記(1)又は(2)のβ−アルコキシプロピオンアミド類を含有することを特徴とする洗浄剤、
(5)、一般式(II)で表されるβ−アルコキシプロピオンアミド類に薬剤を溶解させたことを特徴とする液状薬剤組成物、(Wherein R 1 is an alkyl group having 3 to 18 carbon atoms, and R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon group optionally having an ether bond having 1 to 6 carbon atoms, and are the same as each other) Or may be different from each other and may be bonded to each other to form a ring structure.)
(2) β-alkoxypropionamides of the above (1), wherein R 2 and R 3 are methyl groups,
(3) a solvent characterized by containing the β-alkoxypropionamide of (1) or (2) above,
(4) a cleaning agent comprising the β-alkoxypropionamide of (1) or (2) above,
(5), a liquid drug composition characterized by dissolving a drug in β-alkoxypropionamides represented by the general formula (II),
(式中、R4は炭素数8〜18のアルキル基、R2およびR3はそれぞれ独立に水素原子又は炭素数1〜6のエーテル結合を有しても良い炭化水素基であり、互いに同一であっても異なっていてもよく、さらに互いに結合して環構造を形成してもよい。)
(6)、R2およびR3がメチル基である(5)の液状薬剤組成物、
(7)、薬剤が農業用薬剤である(5)又は(6)の液状薬剤組成物、(Wherein R 4 is an alkyl group having 8 to 18 carbon atoms, and R 2 and R 3 are each independently a hydrogen atom or a hydrocarbon group optionally having an ether bond having 1 to 6 carbon atoms, and are the same as each other) Or may be different from each other and may be bonded to each other to form a ring structure.)
(6) The liquid pharmaceutical composition of (5), wherein R 2 and R 3 are methyl groups,
(7) The liquid drug composition according to (5) or (6), wherein the drug is an agricultural drug,
(8)、塩基性触媒の存在下、一般式(III)で表されるアクリルアミドと炭素数3〜18の脂肪族一価アルコールを反応させることを特徴とする一般式(IV)で表されるβ−アルコキシプロピオンアミド類の製造方法、 (8) represented by general formula (IV), characterized by reacting acrylamide represented by general formula (III) with an aliphatic monohydric alcohol having 3 to 18 carbon atoms in the presence of a basic catalyst. a process for producing β-alkoxypropionamides,
(式中、R2およびR3は一般式(I)と同様である。)(In the formula, R 2 and R 3 are the same as in the general formula (I).)
(式中、R5は炭素数5〜18のアルキル基であり、R2および R3は前記と同様である。)
(9)、塩基性触媒が、カリウム t−ブトキシド、ナトリウム t−ブトキシド、水酸化カリウム及び炭酸カリウムからなる群から選ばれた少なくとも一種の化合物である上記(8)のβ−アルコキシプロピオンアミド類の製造方法
を提供する。(In the formula, R 5 is an alkyl group having 5 to 18 carbon atoms, and R 2 and R 3 are the same as described above.)
(9) The β-alkoxypropionamides of (8) above, wherein the basic catalyst is at least one compound selected from the group consisting of potassium t-butoxide, sodium t-butoxide, potassium hydroxide and potassium carbonate. A manufacturing method is provided.
本発明のβ−アルコキシプロピオンアミド類は、次の一般式(I)で表される。 The β-alkoxypropionamides of the present invention are represented by the following general formula (I).
上記一般式(I)において、R1は炭素数3〜18のアルキル基、R2およびR3は、それぞれ水素原子,又は炭素数1〜6のエーテル結合を有してもよい一価の炭化水素基を示す。ここで、 R1のアルキル基としては、各種ブチル基,各種ペンチル基、各種ヘキシル基、各種オクチル基などが挙げられ、炭素数4〜12のものが好ましく、炭素数5〜10のものが特に好ましい。R2およびR3炭化水素基としては、直鎖状,分岐状のいずれであってもよいが飽和炭化水素基が好ましい。その例としては、メチル基,エチル基,各種プロピル基,各種ブチル基,メトキシメチル基,メトキシエチル基,エトキシエチル基などが挙げられ、メチル基が最も一般的である。R2およびR3は互いに同一であっても異なっていてもよく、さらに互いに結合して環構造を形成してもよい。この環構造は、窒素をヘテロ原子とする複素環構造であってもよく、また、窒素原子と酸素原子をヘテロ原子とする複素環構造であってもよい。この複素環構造を有する基としては、例えば1−ピロリジニル基、ピペジリノ基、モルホリノ基などを挙げることができる。In the above general formula (I), R 1 is an alkyl group having 3 to 18 carbon atoms, R 2 and R 3 are each a hydrogen atom or a monovalent carbon which may have an ether bond having 1 to 6 carbon atoms. Indicates a hydrogen group. Here, examples of the alkyl group for R 1 include various butyl groups, various pentyl groups, various hexyl groups, various octyl groups, and the like, preferably those having 4 to 12 carbon atoms, particularly those having 5 to 10 carbon atoms. preferable. The R 2 and R 3 hydrocarbon groups may be linear or branched, but are preferably saturated hydrocarbon groups. Examples thereof include a methyl group, an ethyl group, various propyl groups, various butyl groups, a methoxymethyl group, a methoxyethyl group, and an ethoxyethyl group, and the methyl group is the most common. R 2 and R 3 may be the same or different from each other, and may be further bonded to each other to form a ring structure. This ring structure may be a heterocyclic structure having nitrogen as a heteroatom, or may be a heterocyclic structure having a nitrogen atom and an oxygen atom as heteroatoms. Examples of the group having a heterocyclic structure include a 1-pyrrolidinyl group, a piperidino group, and a morpholino group.
本発明のβ−アルコキシプロピオンアミド類は、種々の化合物に対してアミド系溶剤とほぼ同等の溶解力を有しており、更にパラフィン類とも溶解することから、溶剤および洗浄剤として広く用いることができる。
特に、一般式(I)においてR1が炭素数8〜18のアルキル基の場合には水に不溶性であるので、本発明のβ−アルコキシプロピオンアミド類は、殺虫剤や殺菌剤等の農薬を溶解させることにより、長期間の効果を持続することができる。
すなわち、次の一般式(II)で表されるβ−アルコキシプロピオンアミド類は上記の農薬を溶解させた液状薬剤組成物、すなわち、乳剤、油剤などの液体施用剤として極めて有利に用いることができる。The β-alkoxypropionamides of the present invention have almost the same dissolving power as various amide solvents for various compounds, and also dissolve in paraffins, so that they are widely used as solvents and cleaning agents. it can.
In particular, in the general formula (I), when R 1 is an alkyl group having 8 to 18 carbon atoms, it is insoluble in water, so that the β-alkoxypropionamides of the present invention are used for pesticides such as insecticides and fungicides. By dissolving it, long-term effects can be maintained.
That is, β-alkoxypropionamides represented by the following general formula (II) can be used very advantageously as a liquid pharmaceutical composition in which the above agricultural chemicals are dissolved, that is, as a liquid application agent such as an emulsion or oil. .
一般式(II)においてR4は炭素数8〜18のアルキル基であり、n−オクチル基、2−エチルヘキシル基などの各種オクチル基や、各種ノニル基、各種デシル基、各種ラウリル基、各種ステアリル基、各種オレイル基などが挙げられる。R2およびR3は一般式(I)の場合と同様である。In the general formula (II), R 4 is an alkyl group having 8 to 18 carbon atoms, various octyl groups such as n-octyl group and 2-ethylhexyl group, various nonyl groups, various decyl groups, various lauryl groups, various stearyls. Groups and various oleyl groups. R 2 and R 3 are the same as in the general formula (I).
β−アルコキシプロピオンアミド類を製造する本発明の方法においては、塩基性触媒の存在下、一般式(III)で表されるアクリルアミド類と炭素数5〜18の脂肪族一価アルコールを反応させ、一般式(IV)で表されるβ−アルコキシプロピオンアミド類を製造する。 In the method of the present invention for producing β-alkoxypropionamides, in the presence of a basic catalyst, the acrylamide represented by the general formula (III) is reacted with an aliphatic monohydric alcohol having 5 to 18 carbon atoms, Β-alkoxypropionamides represented by the general formula (IV) are produced.
前記の一般式(III)で表されるアクリルアミド類において、R2およびR3は一般式(I)と同様である。このようなアクリルアミド類は、具体的には、アクリルアミド、N−メチルアクリルアミド、N,N−ジメチルアクリルアミド、N−エチルアクリルアミド、N,N−ジエチルアクリルアミド、N−プロピルアクリルアミド、N,N−ジプロピルアクリルアミド、N−ブチルアクリルアミド、N,N−ジブチルアクリルアミド、1−アクリロイルピロリジン、1−アクリロイルピペリジン、4−アクリロイルモルホリンなどが挙げられるが、これらの中で特にアクリルアミド、N−メチルアクリルアミド、N,N−ジメチルアクリルアミド、N−エチルアクリルアミド、N,N−ジエチルアクリルアミド,及び4−アクリロイルモルホリンが好ましい。In the acrylamides represented by the general formula (III), R 2 and R 3 are the same as those in the general formula (I). Specific examples of such acrylamides include acrylamide, N-methylacrylamide, N, N-dimethylacrylamide, N-ethylacrylamide, N, N-diethylacrylamide, N-propylacrylamide, and N, N-dipropylacrylamide. N-butylacrylamide, N, N-dibutylacrylamide, 1-acryloylpyrrolidine, 1-acryloylpiperidine, 4-acryloylmorpholine, etc., among which acrylamide, N-methylacrylamide, N, N-dimethyl are particularly preferable. Acrylamide, N-ethylacrylamide, N, N-diethylacrylamide, and 4-acryloylmorpholine are preferred.
本発明の製造方法におけるもう一つの原料は炭素数5〜18の脂肪族一価アルコールであり、前記の一般式(IV)のR5が炭素数5〜18のアルキル基となる。この脂肪族一価アルコールは、直鎖状、分岐状のいずれであってもよく、具体的にはn−ペンタノール、ヘキサノール、オクタノール、2−エチルヘキサノール、デシルアルコール、ラウリルアルコールなどが挙げられる、
本発明におけるβ−アルコキシプロピオンアミド類が、溶剤や洗浄剤などとして、混合物の形態で用いられる場合には、反応において混合物を製造してもよい。この場合、原料の前記アクリルアミド類を二種以上組み合わせて用いてもよいし、前記脂肪族一価アルコールを二種以上組み合わせて用いてもよく、またその両方であってもよい。
アクリルアミド類と脂肪族一価アルコールとの使用割合は、脂肪族一価アルコールを化学量論的量又はそれよりも過剰に用いることが好ましいが、あまり過剰に用いると経済性の面で不利となるので、一般的には、アクリルアミド類1モルに対して、脂肪族一価アルコールが1.0〜3モル、好ましくは1.0〜2モルの範囲で用いられる。Another raw material in the production method of the present invention is an aliphatic monohydric alcohol having 5 to 18 carbon atoms, and R 5 in the general formula (IV) is an alkyl group having 5 to 18 carbon atoms. The aliphatic monohydric alcohol may be linear or branched, and specifically includes n-pentanol, hexanol, octanol, 2-ethylhexanol, decyl alcohol, lauryl alcohol, and the like.
When the β-alkoxypropionamides in the present invention are used in the form of a mixture as a solvent or a cleaning agent, a mixture may be produced in the reaction. In this case, two or more of the raw acrylamides may be used in combination, or two or more of the aliphatic monohydric alcohols may be used in combination, or both.
The proportion of acrylamide and aliphatic monohydric alcohol used is preferably that the monohydric alcohol is used in a stoichiometric amount or in excess thereof, but if it is used in excess, it is disadvantageous in terms of economy. Therefore, generally, an aliphatic monohydric alcohol is used in an amount of 1.0 to 3 mol, preferably 1.0 to 2 mol, relative to 1 mol of acrylamides.
本発明の方法においては、前記アクリルアミド類と、脂肪族一価アルコールとの反応は、塩基性触媒の存在下に行われる。塩基性物質であれば触媒として使用可能であるが、反応条件および副生物等を考慮すると、カリウム t−ブトキシド、ナトリウム t−ブトキシド、水酸化カリウム及び炭酸カリウムが好適である。ナトリウムメトキシド及びカリウムメトキシドは副生物が生成するので好ましくない。また、水酸化ナトリウムおよび炭酸ナトリウムは反応時間が長くなるので好ましくない。 In the method of the present invention, the reaction between the acrylamide and the aliphatic monohydric alcohol is performed in the presence of a basic catalyst. A basic substance can be used as a catalyst, but potassium t-butoxide, sodium t-butoxide, potassium hydroxide and potassium carbonate are preferred in view of reaction conditions and by-products. Sodium methoxide and potassium methoxide are not preferred because by-products are formed. Further, sodium hydroxide and sodium carbonate are not preferable because the reaction time becomes long.
本発明においては、前記塩基性触媒は、一種を単独で用いてもよく、二種以上を組み合わせて用いてもよい。また、その使用量は特に制限はなく、原料の種類などに応じて適宜選定されるが、一般的にアクリルアミド1モルに対して0.5〜10モル%、好ましくは1〜3モル%の範囲で選定される。
反応温度は20〜80℃が好ましく、さらに30〜50℃の範囲から選択することが好ましい。あまり高温では収率が低下する場合があり、あまり低温では反応速度が低下して実用的でない。また、反応圧力は、常圧でも加圧下でも反応は進行するが、一般的に常圧の方が経済的に有利である。反応時間は、使用する原料や触媒の種類、反応温度などに左右され、一概に決めることはできないが、通常30分〜10時間であり、好ましくは1〜5時間である。溶媒は、アセトン、エーテルおよびアミド系溶媒を使用することができるが、経済性を考慮すると使用しないことが好ましい。In this invention, the said basic catalyst may be used individually by 1 type, and may be used in combination of 2 or more type. The amount used is not particularly limited and is appropriately selected according to the type of raw material, but is generally in the range of 0.5 to 10 mol%, preferably 1 to 3 mol% with respect to 1 mol of acrylamide. Is selected.
The reaction temperature is preferably 20 to 80 ° C, and more preferably selected from the range of 30 to 50 ° C. If the temperature is too high, the yield may decrease, and if the temperature is too low, the reaction rate decreases, which is not practical. In addition, the reaction proceeds at normal pressure or under pressure, but generally normal pressure is economically advantageous. The reaction time depends on the raw materials used, the type of catalyst, the reaction temperature, etc., and cannot be determined in general, but is usually 30 minutes to 10 hours, preferably 1 to 5 hours. As the solvent, acetone, ether and amide solvents can be used, but it is preferable not to use them in consideration of economy.
生成したβ−アルコキシプロピオンアミド類は、反応終了後にリン酸、酢酸や硫酸などにより触媒として使用した塩基を中和した後、濾過等により生成する塩を除去するのが良い。また、必要に応じて未反応物を薄膜蒸発器などにより分離することにより得ることができる。
このように、本発明においては、アミド系溶剤として優れた性能を有するβ−アルコキシプロピオンアミド類を温和な条件で短時間に反応させることができ、しかも反応後の後処理、精製が容易な方法で製造することができる。The produced β-alkoxypropionamide is preferably neutralized with a base used as a catalyst with phosphoric acid, acetic acid, sulfuric acid or the like after completion of the reaction, and then the salt produced by filtration or the like is removed. Moreover, it can obtain by isolate | separating an unreacted substance with a thin film evaporator etc. as needed.
As described above, in the present invention, β-alkoxypropionamides having excellent performance as amide solvents can be reacted in a short time under mild conditions, and post-reaction and purification after the reaction are easy. Can be manufactured.
次に、本発明を実施例によりさらに詳細に説明するが、本発明はこれらの例によってなんら限定されるものではない。
なお、以下の実施例および比較例において、溶解性試験は下記の方法で行った。
各実施例で得られた化合物(β−アルコキシプロピオンアミド類)および比較例で用いたアミド系溶剤5mLと、溶解性確認物質としてn−ヘキサン、流動パラフィン、グリセリンおよび水5gを各々の試験管に入れ、室温又は80℃で5分間振とうさせた。80℃で加熱した場合は、室温まで冷却した後、溶液の状態を観察した。均一の状態を相溶性、少しでも濁り又は相分離のあるものを非相溶性とした。
溶解性試験の結果については、次のように表示した。
○:室温で相溶性のもの、
Δ:80℃に加熱すると相溶性のもの、
×:非相溶性のものEXAMPLES Next, although an Example demonstrates this invention further in detail, this invention is not limited at all by these examples.
In the following Examples and Comparative Examples, the solubility test was performed by the following method.
The compound (β-alkoxypropionamides) obtained in each Example and 5 mL of the amide solvent used in Comparative Examples, and n-hexane, liquid paraffin, glycerin and 5 g of water as the solubility confirmation substances were added to each test tube. And shaken at room temperature or 80 ° C. for 5 minutes. When heated at 80 ° C., the solution was observed after cooling to room temperature. A uniform state was made compatible, and a turbid or phase-separated one was made incompatible.
About the result of the solubility test, it displayed as follows.
○: compatible at room temperature,
Δ: compatible with heating to 80 ° C.
×: Incompatible
〔実施例1〕
攪拌装置、熱電対および窒素ガス導入管を備えた300mLセパラブルフラスコに、N,N−ジメチルアクリルアミド19.828gおよび1−ヘキサノール20.434gを入れ、窒素ガスを導入しながら攪拌した。次に、ナトリウム t−ブトキシド0.338gを加え、35℃で4時間反応を行った。加熱終了後、リン酸150mgを加え、溶液を均一にした後、3時間放置した。溶液を濾過して、析出物を除去し、さらにエバポレーターで未反応物を除いた。収量は37.4g(収率93%)であった。
得られた物質の1H−NMRを測定したところ、0.95ppm(3H)、1.3〜1.5ppm(8H)、2.4ppm(2H)、2.9ppm(6H)、3.4ppm(2H)および3.7ppm(2H)を観測した。その結果、以下の構造であることが分かった。この化合物の溶解性試験を行った。結果を第1表に示す。[Example 1]
N, N-dimethylacrylamide (19.828 g) and 1-hexanol (20.434 g) were placed in a 300 mL separable flask equipped with a stirrer, a thermocouple, and a nitrogen gas inlet tube, and stirred while introducing nitrogen gas. Next, 0.338 g of sodium t-butoxide was added and reacted at 35 ° C. for 4 hours. After completion of heating, 150 mg of phosphoric acid was added to make the solution uniform, and the mixture was allowed to stand for 3 hours. The solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator. The yield was 37.4 g (93% yield).
When 1 H-NMR of the obtained substance was measured, 0.95 ppm (3H), 1.3 to 1.5 ppm (8H), 2.4 ppm (2H), 2.9 ppm (6H), 3.4 ppm ( 2H) and 3.7 ppm (2H) were observed. As a result, the following structure was found. A solubility test of this compound was performed. The results are shown in Table 1.
〔実施例2〕
攪拌装置、熱電対および窒素ガス導入管を備えた300mLセパラブルフラスコに、N,N−ジメチルアクリルアミド19.828gおよび1−ブタノール14.824gを入れ、窒素ガスを導入しながら攪拌した。次に、ナトリウム t−ブトキシド0.338gを加え、35℃で4時間反応を行った。加熱終了後、リン酸150mgを加え、溶液を均一にした後、3時間放置した。溶液を濾過して、析出物を除去し、さらにエバポレーターで未反応物を除いた。収量は30.5g(収率88%)であった。
得られた物質の1H−NMRを測定したところ、0.95ppm(3H)、1.3〜1.5ppm(4H)、2.4ppm(2H)、2.9ppm(6H)、3.4ppm(2H)および3.7ppm(2H)を観測した。その結果、以下の構造であることが分かった。この化合物の溶解性試験を行った。結果を第1表に示す。[Example 2]
N, N-dimethylacrylamide (19.828 g) and 1-butanol (14.824 g) were placed in a 300 mL separable flask equipped with a stirrer, a thermocouple, and a nitrogen gas inlet tube, and stirred while introducing nitrogen gas. Next, 0.338 g of sodium t-butoxide was added and reacted at 35 ° C. for 4 hours. After completion of heating, 150 mg of phosphoric acid was added to make the solution uniform, and the mixture was allowed to stand for 3 hours. The solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator. The yield was 30.5 g (88% yield).
When 1 H-NMR of the obtained substance was measured, it was 0.95 ppm (3H), 1.3 to 1.5 ppm (4H), 2.4 ppm (2H), 2.9 ppm (6H), 3.4 ppm ( 2H) and 3.7 ppm (2H) were observed. As a result, the following structure was found. A solubility test of this compound was performed. The results are shown in Table 1.
〔実施例3〕
攪拌装置、熱電対および窒素ガス導入管を備えた300mLセパラブルフラスコにN,N−ジメチルアクリルアミド19.828gおよび2−エチルヘキサノール26.046gを入れ、窒素ガスを導入しながら攪拌した。次に、ナトリウム t−ブトキシド0.338gを加え、35℃で4時間反応を行った。加熱終了後、リン酸150mgを加え、溶液を均一にした後、3時間放置した。溶液を濾過して、析出物を除去し、さらにエバポレーターで未反応物を除いた。収量は43.6g(収率95%)であった。
得られた物質の1H−NMRを測定したところ、0.95ppm(6H)、1.2〜1.4ppm(8H)、1.8ppm(1H)、2.4ppm(2H)、2.9ppm(6H)、3.4ppm(2H)および3.7ppm(2H)を観測した。
その結果、以下の構造であることが分かった。この化合物の溶解性試験を行った。結果を第1表に示す。Example 3
N, N-dimethylacrylamide (19.828 g) and 2-ethylhexanol (26.046 g) were placed in a 300 mL separable flask equipped with a stirrer, a thermocouple, and a nitrogen gas inlet tube, and stirred while introducing nitrogen gas. Next, 0.338 g of sodium t-butoxide was added and reacted at 35 ° C. for 4 hours. After completion of heating, 150 mg of phosphoric acid was added to make the solution uniform, and the mixture was allowed to stand for 3 hours. The solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator. The yield was 43.6 g (yield 95%).
When 1 H-NMR of the obtained substance was measured, 0.95 ppm (6H), 1.2 to 1.4 ppm (8H), 1.8 ppm (1H), 2.4 ppm (2H), 2.9 ppm ( 6H), 3.4 ppm (2H) and 3.7 ppm (2H) were observed.
As a result, the following structure was found. A solubility test of this compound was performed. The results are shown in Table 1.
〔実施例4〕
実施例3において2−エチルヘキサノールの代わりにn−オクタノール26.046gを使用した以外は実施例3と同様に行った。収量は42.7g(収率93%)であった。溶解性試験の結果を第1表に示す。Example 4
In Example 3, it carried out like Example 3 except having used 26.046g of n-octanol instead of 2-ethylhexanol. The yield was 42.7 g (93% yield). The results of the solubility test are shown in Table 1.
〔実施例5〕
攪拌装置、熱電対および窒素ガス導入管を備えた2LセパラブルフラスコにN,N−ジメチルアクリルアミド416.34gおよびラウリルアルコール745.36gを入れ、窒素ガスを導入しながら攪拌した。次に、カリウム t−ブトキシド22.44gを加え、40℃で3時間反応を行った。加熱終了後、リン酸22.44gを加え、溶液を均一にした後、3時間放置した。溶液を濾過して、析出物を除去し、さらにエバポレーターで未反応物を除いた。収量は947.0g(収率83%)であった。
得られた物質の1H−NMRを測定したところ、0.80〜0.85ppm(3H)、1.15〜1.28ppm(22H)、2.85〜3.00ppm(6H)、3.35〜4.00ppm(2H)および3.65〜3.70ppm(2H)を観測した。
その結果、次の構造であることが分かった。この化合物の溶解性試験を行った。結果を第1表に示す。Example 5
In a 2 L separable flask equipped with a stirrer, a thermocouple, and a nitrogen gas inlet tube, 41.34 g of N, N-dimethylacrylamide and 745.36 g of lauryl alcohol were added and stirred while introducing nitrogen gas. Next, 22.44 g of potassium t-butoxide was added, and the reaction was performed at 40 ° C. for 3 hours. After the heating was completed, 22.44 g of phosphoric acid was added to make the solution uniform, and the mixture was allowed to stand for 3 hours. The solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator. The yield was 947.0 g (83% yield).
When 1 H-NMR of the obtained substance was measured, 0.80 to 0.85 ppm (3H), 1.15 to 1.28 ppm (22H), 2.85 to 3.00 ppm (6H), 3.35. ˜4.00 ppm (2H) and 3.65 to 3.70 ppm (2H) were observed.
As a result, the following structure was found. A solubility test of this compound was performed. The results are shown in Table 1.
〔比較例1〜3〕
アミド系溶剤であるN−メチルピロリドン、N,N−ジメチルホルムアミドおよびアセトンを用いて溶解性試験を行った。結果を第1表に示す。[Comparative Examples 1-3]
A solubility test was conducted using N-methylpyrrolidone, N, N-dimethylformamide and acetone which are amide solvents. The results are shown in Table 1.
本発明のβ−アルコキシプロピオンアミド類は、従来のアミド系溶剤の溶解力を保持しつつ、沸点が高く、更にパラフィン等への溶解力も有し、優れた洗浄剤や溶剤として広く用いることができる。
また、一般式(II)で表されるβ−アルコキシプロピオンアミド類については、殺虫剤や殺菌剤などの農薬に対して従来のアミド系溶剤の溶解力を保持しつつ、水に溶解しないので排水等への汚染が無くなり安全性が高く、農薬としての効果を長期間持続することができる。従って一般式(II)で表されるβ−アルコキシプロピオンアミド類は、農薬における乳剤、油剤などの液状薬剤組成物(液体施用剤)として極めて有用である。
さらに、本発明のβ−アルコキシプロピオンアミド類の製造方法は、温和な反応条件で短時間の反応でβ−アルコキシプロピオンアミド類が得られ、しかも反応後の後処理、精製が容易で効率的に製造することができる。
The β-alkoxypropionamides of the present invention have a high boiling point and a solubility in paraffin while maintaining the solubility of conventional amide solvents, and can be widely used as excellent cleaning agents and solvents. .
In addition, the β-alkoxypropionamides represented by the general formula (II) retain the dissolving power of conventional amide solvents for agricultural chemicals such as insecticides and fungicides, and do not dissolve in water. The safety as an agrochemical can be maintained for a long time. Accordingly, β-alkoxypropionamides represented by the general formula (II) are extremely useful as liquid pharmaceutical compositions (liquid application agents) such as emulsions and oils in agricultural chemicals.
Furthermore, the method for producing β-alkoxypropionamides according to the present invention allows β-alkoxypropionamides to be obtained in a short reaction under mild reaction conditions, and the post-treatment and purification after the reaction are easy and efficient. Can be manufactured.
Claims (9)
The method for producing a β-alkoxypropionamide according to claim 8, wherein the basic catalyst is at least one compound selected from the group consisting of potassium t-butoxide, sodium t-butoxide, potassium hydroxide, and potassium carbonate.
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KR101304723B1 (en) * | 2006-08-22 | 2013-09-05 | 동우 화인켐 주식회사 | Photoresist stripping liquid containing amide and a methodof stripping photoresists using the same |
JP5233028B2 (en) * | 2006-12-19 | 2013-07-10 | ライオン株式会社 | Cleaning solvent for liquid detergent composition |
FR2930774B1 (en) | 2008-04-30 | 2010-09-17 | Rhodia Operations | ETHER-AMIDE-TYPE COMPOUNDS, PROCESS FOR PREPARATION AND USE |
JP5568863B2 (en) * | 2009-01-21 | 2014-08-13 | 東洋インキScホールディングス株式会社 | Water-based ink composition using β-alkoxypropionamides |
JP5716260B2 (en) * | 2009-02-06 | 2015-05-13 | 東洋インキScホールディングス株式会社 | Non-aqueous ink composition |
US8748659B2 (en) * | 2009-05-01 | 2014-06-10 | Idemitsu Kosan Co., Ltd. | Method for producing alpha,beta-unsaturated carboxylic acid-N,N-disubstituted amide and method for producing 3-alkoxycarboxylic acid-N,N-disubstituted amide |
BR112012002245A2 (en) | 2009-07-31 | 2016-06-07 | Basf Se | liquid composition, process for preparing the composition, use of the composition and emulsion comprising water |
JP5499344B2 (en) * | 2009-09-28 | 2014-05-21 | 大日本塗料株式会社 | Water-based ink composition |
JP2011246571A (en) | 2010-05-26 | 2011-12-08 | Seiko Epson Corp | Nonaqueous ink composition for ink jet recording and inkjet recording method |
JP5574099B2 (en) | 2010-05-26 | 2014-08-20 | セイコーエプソン株式会社 | Ink composition for inkjet printing and inkjet printing method |
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CN103492520B (en) * | 2011-04-25 | 2015-08-19 | 旭硝子株式会社 | Water-repellent oil-repellent agent composition, its manufacture method and article |
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CN112218531B (en) * | 2018-05-28 | 2021-10-01 | 日产化学株式会社 | Emulsifiable composition of agricultural chemicals |
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