Process for production of N-vinyl compound

• US 5,700,946 A
• Filed: 04/17/1996
• Issued: 12/23/1997
• Est. Priority Date: 04/18/1995
• Status: Expired due to Term

• Current Assignee: Nippon Shokubai Company Limited
• Original Assignee: Nippon Shokubai Company Limited
• Inventors: Kanbe, Hideyuki, Kurusu, Akira, Shimasaki, Yuuji
• Primary Examiner(s): Grumbling, Matthew V.
• Assistant Examiner(s): BUCKNUM, MICHAE
• Application Number:
  US08/633,469
• Time in Patent Office: 615 Days
• Field of Search: 548/552, 548/231, 564/215, 560/157
• US Class Current: 548/231
• CPC Class Codes: B01J 27/1806 with alkaline or alkaline earth metals
• CPC Class Codes: C07B 43/00 Formation or introduction of functional groups containing nitrogen
• CPC Class Codes: C07C 269/06 by reactions not involving the formation of carbamate groups
• CPC Class Codes: C07D 207/267 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 263/22 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms

Abstract

The present invention provides a process for producing an N-vinyl compound, which comprises subjecting an N-(-alkoxyalkyl) compound to gas phase intramolecular alcohol elimination to convert said compound to an N-vinyl compound directly in one step, wherein a solid oxide containing phosphorus and an alkali metal and/or an alkaline earth metal is used as a catalyst. This process need not use any solvent or any auxiliary raw material and consequently can produce an N-vinyl compound simply and safely without generating any waste material derived from the auxiliary raw material.

Claims

1. A process for producing an N-vinyl compound of the following formula (2) ##STR12## wherein m and n are each independently 0 or 1,

R₁ and R₂ are each independently one member selected from the group consisting of hydrogen, hydrocarbon groups having 1-8 carbon atoms and alkoxy groups having 1-6 carbon atoms, with the provisos that (i) when m and n are each 0, none of R₁ and R₂ are hydrogen, and (ii) when none of R₁ and R₂ are hydrogen, R₁ and R₂ may bond to each other to form, together with N, a five- to seven-membered ring which may contain unsaturated bond(s) and/or hetero atom(s) selected from the group consisting of S, O and N other than said N already shown in formula (2), and

R₄ is one member selected from the group consisting of hydrogen and hydrocarbon groups having 1-6 carbon atoms, said process comprising:

subjecting an N-(1-alkoxyalkyl) compound of the following formula (1) ##STR13## wherein R₁, R₂, R₄, m and n are the same as in formula (2), and

R₃ is one member selected from the group consisting of methyl group, ethyl group, propyl group and butyl group, to alcohol elimination in a gas phase in the presence of a solid oxide catalyst of the following formula (13)

space="preserve" listing-type="equation">PaXbYcOd (13)

wherein

P is phosphorus,

X is at least one element selected from the group consisting of alkali metals and alkaline earth metals,

Y is at least one element selected from the group consisting of Ti, Zr, Nb, B, Al and Si,

O is oxygen,

a, b, c and d are the atomic ratios of P, X, Y and O, respectively, with a;

b;

c being 1;

0.5-5;

0-500, and d being determined by a, b, c and the bonding states of the individual elements to convert said N-(1-alkoxyalkyl) compound of the formula (1) into an N-vinyl compound of the formula (2).

2. The process according to claim 1, wherein said N-(1-alkoxyalkyl) compound is an N-(1-alkoxyalkyl)-2-oxazolidone of the following formula (3) ##STR14## wherein R₃ is one member selected from the group consisting of methyl group, ethyl group, propyl group and butyl group, and

R₄ is one member selected from the group consisting of hydrogen, methyl group and ethyl group, and said N-(1-alkoxyalkyl)-2-oxazolidone of the formula (3) is subjected to said alcohol elimination to produce an N-vinyl-2-oxazolidone of the following formula (4) ##STR15## wherein R₄ is the same as in formula (3).

3. The process according to claim 1, wherein said N-(1-alkoxyalkyl) compound is an N-(1-alkoxyalkyl)-O-alkylcarbamate of the following formula (5) ##STR16## wherein R₁ and R₃ are each independently one member selected from the group consisting of methyl group, ethyl group, propyl group and butyl group,

R₂ is one member selected from the group consisting of hydrogen and hydrogen groups having 1-4 carbon atoms, and

R₄ is one member selected from the group consisting of hydrogen, methyl group and ethyl group, and said N-(1-alkoxyalkyl)-O-alkylcarbamate of the formula (5) is subjected to said alcohol elimination to produce an N-vinyl-O-alkylcarbamate of the following formula (6) ##STR17## wherein R₁, R₂ and R₄ are the same as in formula (5).

4. The process according to claim 1, wherein said N-(1-alkoxyalkyl) compound is an N-(1-alkoxyalkyl)-amide of the following formula (7) ##STR18## wherein R₁ and R₂ are each independently one member selected from the group consisting of hydrogen and hydrocarbon groups having 1-8 carbon atoms with the proviso that R₁ and R₂ may bond to each other to form, together with N, a five- to seven-membered ring which may contain hetero atom(s) selected from the group consisting of S, O and N other than said N,

R₃ is one member selected from the group consisting of methyl group, ethyl group, propyl group and butyl group, and

R₄ is one member selected from the group consisting of hydrogen and hydrocarbon groups having 1-6 carbon atoms, and said N-(1-alkoxyalkyl)-amide of the formula (7) is subjected to said alcohol elimination to produce an N-vinylamide of the following formula (8) ##STR19## wherein R₁, R₂ and R₄ are the same as in formula (7).