US3904635A
Expired / Lapsed
US
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Method for preparing n-alkyl-' ,' -unsaturated amide
Assignee: Asahi Kasei Corp
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Filing: 1973-07-20
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Granted: 1975-09-09
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Expires: 1993-07-20
Abstract
Abstract WHEREIN R1 represents a hydrogen atom or an alkyl group to react with 1-10 parts by mole of an alkylamine represented by the general formula, WHEREIN R2 represents a hydrogen atom or an alkyl group, R3 an alkyl group, and R4 an alkylene group having four to five carbon atoms, and 1-20 parts by mole of water at a temperature of 100* 300*C in the presence or in the absence of a catalyst. The Nalkyl- Alpha , Beta -unsaturated amide is used as a monomer for resins, modifiers for polymers and intermediate products for organic chemicals. A N-alkyl Alpha , Beta -unsaturated amide is prepared by allowing one part by mole of an Alpha , Beta -unsaturated nitrile represented by a general formula of
Inventors
- 👤 Saburo Senoo
- 👤 Naoya Kominami
- 👤 Yohei Fukuoka
- 👤 Katsuyoshi Sasaki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 04:08
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07C; C07C233/00; C07C233/01; C07C233/02
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
28 words
A METHOD FOR PREPARING AN N-ALKYL-A,B-UNSATUATED AMIDE, WHICH COMPRISES REACTING AT A TEMPERATURE RANGING FROM 100* TO 300*C, AND UNDER SUPERATMOPPHERIC PRESSURE, A,BUNSATURATED NITRILE REPRESENTED BY THE FORMULA,
Claim 2
Independent Claim
28 words
A METHOD FOR PREPARING AN N-ALKYL-A,B-UNSATUATED AMIDE, WHICH COMPRISES REACTING AT A TEMPERATURE RANGING FROM 100* TO 300*C, AND UNDER SUPERATMOPPHERIC PRESSURE, A,BUNSATURATED NITRILE REPRESENTED BY THE FORMULA,
Claim 3
Dependent Claim
29 words
The method of claim 1 wherein the alkylamine is used in a molar amount of at least twice as much as that of the Alpha , Beta -unsaturated nitrile.
Claim 4
Dependent Claim
28 words
A method according to claim 1 wherein the water is used in a molar amount 1-20 times as much as that of the Alpha , Beta -unsaturated nitrile.
Claim 5
Dependent Claim
12 words
A method according to claim 1 wherein the byproduct obtained is recycled.
Claim 6
Dependent Claim
26 words
A method according to claim 1 wherein the alkylamine is removed from the reaction system with heating while passing an inert gas through the reaction system.
Claim 7
Dependent Claim
40 words
A method according to claim 1 wherein the alkylamine is removed from the reaction system under a superatmospheric pressure with heating to a temperature above the boiling point under the atmosphere of the formed N-alkyl- Alpha , Beta -unsaturated amide.
Claim 8
Dependent Claim
72 words
A method according to claim 1 wherein at least one member selected from the group consisting of metallic copper, zinc, tin, iron, cobalt, nickel, the oxides, the peroxides, the hydroxides, the inorganic acid salts and the organic acid salts of copper, zinc, tin, iron, cobalt, nickel, cadmium, silver, mercury, titanium, zirconium, lead, vanadium, antimony, bismuth, chromium, molybdenum, tungsten, manganese, ruthenium, rhodium, osmium, palladium, iridium, gold and platinum, is used as a catalyst.
Claim 9
Dependent Claim
27 words
A method according to claim 7 wherein 0.001 to 20% by mole of the catalyst is used on the basis of the Alpha , Beta -unsaturated nitrile.
Claim 10
Dependent Claim
36 words
The method of claim 1 wherein said Alpha , Beta -unsaturated nitrile is selected from the group of acrylonitrile, Alpha -methylacrylonitrile, Alpha -ethylacrylonitrile, Alpha -n-propylacrylonitrile, Alpha -isopropylacrylonitrile, Alpha -n-butylacrylonitrile, Alpha -sec.-butylacrylonitrile, Alpha -n-amylacrylonitrile, and Alpha -n-hexylacrylonitrile.
Claim 11
Dependent Claim
31 words
The method of claim 9 wherein said alkylamine is selected from the group of methylamine, dimethylamine, ethylamine, diethylamine, n-propylamine, di-n-propylamine, n-butylamine, di-n-butylamine, isobutylamine, diisobutylamine, n-amylamine, di-n-amylamine, n-hexylamine, cyclohexylamine, pyrrolidine, and piperidine.
Claim 12
Dependent Claim
31 words
The method of claim 1 wherein said alkylamine is selected from the group of methylamine, dimethylamine, ethylamine, diethylamine, n-propylamine, di-n-propylamine, n-butylamine, di-n-butylamine, isobutylamine, diisobutylamine, n-amylamine, di-n-amylamine, n-hexylamine, cyclohexylamine, pyrrolidine, and piperidine.
Claim 13
Dependent Claim
61 words
The method of claim 7 wherein the inorganic acid salts are selected from the group of carbonates, cyanates, nitrates, sulfates, halides, oxyhalides, sulfides, phosphates, pyrophosphates, borates, nitrites, rhodanates, chromates, bichromates molybdenates, phospho-molybdenates, tungstenates, and permanganates, and wherein the organic acid salts are selected from the group of formates, acetates, peracetates, propionates, butyrates, stearates, oxalates, citrates, p-toluene-sulfonates, picrates, naphthenates, benzoates, and tolylates.
Claim 14
Dependent Claim
160 words
The method of claim 7 wherein said catalyst is selected from the group of zinc acetate, zinc chlorate, silver nitrate, cadmium acetate, cadmium phosphate, mercurous chloride, mercuric chloride, stannous chloride, stannic chloride, potassium permanganate, manganese dichloride, manganese trichloride, manganese tetrachloride, vanadium chloride, antimony trichloride, manganese sulfide, lead peracetate, lead peroxide, lead chlorate, zirconium oxychloride, zinc phosphite, zinc (powdered), tin (powdered), iron (powdered), raney cobalt (powdered), raney nickel (powdered), molybdenic acid, tungstenic acid, cobalt carbonate (basic), zinc stearate, cuprous cyanate, chloroauric acid, mercury thiocyanate, stannous oxalate, p-toluenesulfonic acid, antimony tribromide, bismuth oxychloride, chromium sulfate, chromous chloride, iridium chloride, ammonium permanganate, cobalt naphthenate, nickel bromide, ruthenium chloride, rhodium chloride, palladium chloride, ferrous chloride, ferric bromide, mercuric sulfate, cuprous bromide, cupric iodide, zinc sulfide, ferric formate, cupric n-butyrate, osmium tetrachloride, platinum chloride, titanium trichloride, zinc hydroxide, zinc thiocyanate, zinc phosphite, zinc borate, zinc nitrite, chromic acid, zinc benzoate, zinc tolylate, zinc propionate, zinc citrate, zinc chloride, cupric chloride, cadmium chloride, and cobalt chloride.
Claim 15
Dependent Claim
23 words
The method of claim 7 wherein said catalyst is a mixture of zinc chloride, zinc acetate, osmium tetrachloride, lead oxide and zinc (powdered).
Claim 16
Dependent Claim
20 words
The method of claim 7 wherein the said catalyst is selected from the groUp of powdered copper and phosphomolybdenic acid.
Claim 17
Dependent Claim
26 words
The method of claim 7 wherein the oxides, the peroxides, and the hydroxides are selected from the group of lead oxide, lead peroxide, and zinc hydroxide.
Claim 18
Dependent Claim
21 words
The method of claim 1 wherein the reaction is carried out at a temperature ranging from 150* C to 280* C.
Claim 19
Independent Claim
41 words
A method for preparing an N-alkyl- Alpha , Beta -unsaturated amide, which comprises reacting at a temperature ranging from 100* to 300* C and under superatmospheric pressure, and maintaining the liquid phase Alpha , Beta -unsaturated nitrile represented by the formula,
Claim 20
Independent Claim
41 words
A method for preparing an N-alkyl- Alpha , Beta -unsaturated amide, which comprises reacting at a temperature ranging from 100* to 300* C and under superatmospheric pressure, and maintaining the liquid phase Alpha , Beta -unsaturated nitrile represented by the formula,
References Cited (Backward Citations)
US2357484A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-09-08 | 1979-03-10 | 1979-09-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-09-08 | 1983-03-10 | 1983-09-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-09-08 | 1987-03-10 | 1987-09-09 | $7700.00 | Window Closed / Lapsed |