Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-04-02
2004-03-23
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S855000
Reexamination Certificate
active
06710213
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing propargyl alcohol and its intermediate which are useful as a starting material of organic products, and also relates to the use thereof.
RELATED BACKGROUND ART
With respect to the process for producing propargyl alcohol, for example, a method of reacting acetylene with formaldehyde is known and described in JP-A-64-90145 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”).
However, this method has a problem in that highly explosive acetylene is used.
In order to solve the problem, a method of producing propargyl alcohol in which chloroallyl alcohol is dehydrochlorinated by reacting with an alkali metal hydroxide is known and described, for example, in U.S. Pat. No. 3,383,427
, Khim. Prom-st.,
19, 59 (1987), and
J. Org. Chem
., 15, 654 (1950). With respect to the process for producing chloroallyl alcohol used as a starting material, a method of reacting 1,2,3-trichloropropane with an alkali is known and described, for example, in U.S. Pat. No. 2,285,329.
However, for producing propargyl alcohol, a sufficiently large amount of an amine compound or ammonia must be added in addition to the alkali metal hydroxide. In the case of ammonia, the ammonia is used in an amount as large as 5 to 20 mol per mol of 2-chloroallyl alcohol.
In such a process, the produced propargyl alcohol is liable to decompose or polymerize to lower the productivity, and the isolated and purified propargyl alcohol is also thermally unstable, being liable to decompose or polymerize.
OBJECT OF THE INVENTION
The present invention has been made under these circumstances and the object of the present invention is to provide a process for producing propargyl alcohol ad its intermediate chloroallyl alcohol in an industrially advantageous manner.
DISCLOSURE OF THE INVENTION
As a result of extensive investigations to overcome the above-described problems, the present inventors have found that propargyl alcohol can be produced in a high yield by reacting 1,2,3-trichloropropane with 3 equivalents or more of an alkali compound, and have completed the present invention (first embodiment).
Also, the present inventors have found that a process for producing propargyl alcohol through a step of reacting 2,3-dichloro-1-propanol with an amine to produce chloroallyl alcohol can attain the object, and have completed the present invention (second embodiment).
The present invention provides a production process and a use for propargyl alcohol and its intermediate, described in (1) to (41) below.
(1) A process for producing propargyl alcohol, comprising reacting 1,2,3-trichloropropane with 3 equivalents or more of an alkali compound.
(2) The process for producing propargyl alcohol as described in (1) above, wherein the reaction is performed at a temperature selected from the range of 20° C. to 200° C.
(3) The process for producing propargyl alcohol as described in (1) or (2) above, wherein the reaction is performed under pressure.
(4) The process for producing propargyl alcohol as described in (1) above, wherein the reaction comprises a first step of reacting 1,2,3-trichloropropane with an alkali compound to produce 2-chloroallyl alcohol and a second step of reacting the 2-chloroallyl alcohol with an alkali compound to produce propargyl alcohol.
(5) The process for producing propargyl alcohol as described in (4) above, wherein the first step and the second step are continuously performed.
(6) A process for producing propargyl alcohol, comprising reacting 1,2,3-trichloropropane with an aqueous solution containing 3 equivalents or more of an alkali compound.
(7) The process for producing propargyl alcohol as described in (6) above, wherein the reaction is performed at a temperature selected from the range of 20° C. to 200° C.
(8) The process for producing propargyl alcohol as described in (6) or (7) above, wherein the reaction is performed under pressure.
(9) The process for producing propargyl alcohol as described in (6) above, wherein the reaction comprises a first step of reacting 1,2,3-trichloropropane with an aqueous solution containing an alkali compound to produce 2-chloroallyl alcohol and a second step of reacting the 2-chloroallyl alcohol with an aqueous solution containing an alkali compound to produce propargyl alcohol.
(10) The process for producing propargyl alcohol as described in (9) above, wherein the first step and the second step are continuously performed.
(11) The process for producing propargyl alcohol as described in (1) or (6) above, wherein the alkali compound is at least one compound selected from the group consisting of hydroxides, oxides, carbonates, hydrogencarbonates, phosphates and hydrogenphosphates of an alkali metal and/or an alkaline earth metal. (12) The process for producing propargyl alcohol as described in (1) or (6) above, wherein the alkali compound is a hydroxide, an oxide and/or a carbonate of an alkali metal and/or an alkaline earth metal.
(13) The process for producing propargyl alcohol as described in (1) or (6) above, wherein the reaction is performed in the presence of a quaternary ammonium salt
(14) A process for producing propargyl alcohol, comprising the following two steps:
(1) a step of reacting 2,3-dichloro-1-propanol with an amine to produce chloroallyl alcohol, and
(2) a step of reacting the chloroallyl alcohol obtained in the step (1) with alkali compound to produce propargyl alcohol.
(15) The process for producing propargyl alcohol as described in (14) above, wherein the steps (1) and (2) are continuously performed.
(16) The process for producing propargyl alcohol as described in (14) or (15) above, wherein the step (1) is performed at a temperature of 20 to 300° C. and the step (2) is performed at a temperature of 20 to 200° C.
(17) The process for producing propargyl alcohol as described in (14) or (15) above, wherein the step (1) and/or (2) is performed under pressure.
(18) The process for producing propargyl alcohol as described in (14) or (15) above, wherein the alkali compound in the step (2) is at least one compound selected from the group consisting of hydroxides, oxides, carbonates, hydrogencarbonates, phosphates and hydrogenphosphates of an alkali metal and an alkaline earth metal.
(19) The process for producing propargyl alcohol as described in (1) or (6) or (14) above, wherein the reaction is performed in the presence of a polymerization inhibitor.
(20) The process for producing propargyl alcohol as described in (1) or (6) or (14) above, wherein the process further comprises a purification step performed in the presence of a polymerization inhibitor.
(21) The process for producing propargyl alcohol as described in (19) above, wherein the polymerization inhibitor is at least one compound selected from the group consisting of phenol derivatives, vinyl compounds, sulfur-containing compounds, nitrogen-containing compounds, and metal compounds.
(22) A process for producing chloroallyl alcohol, comprising reacting 2,3-dichloro-1-propanol with an amine.
(23) The process for producing chloroallyl alcohol as described in (22) above, wherein the reaction is performed at a temperature selected from the range of 20° C. to 300° C.
(24) The process for producing chloroallyl alcohol as described in (22) or (23) above, wherein the reaction is performed under pressure.
(25) The process for producing chloroallyl alcohol as described in (22) above, wherein the reaction is performed in the presence of a polymerization inhibitor.
(26) The process for producing chloroallyl alcohol as described in (25) above, wherein the polymerization inhibitor is at least one compound selected from the group consisting of phenol derivatives, vinyl compounds, sulfur-containing compounds, nitrogen-containing compounds, and metal compounds.
(27) Propargyl alcohol, containing a polymerization inhibitor.
(28) The propargyl alcohol as described in (27) above, wherein the polymerization inhibitor is at least one compound selected from the group consisting of phenol derivatives, vinyl compounds, su
Aoki Takanori
Hiro Toshitaka
Ishikami Haruki
Ohe Takami
Saito Makoto
Price Elvis O.
Showa Denko K.K.
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