AU2018100843A4 - Organic intermediates oxalic acid aldehydes synthesis method - Google Patents
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- AU2018100843A4 AU2018100843A4 AU2018100843A AU2018100843A AU2018100843A4 AU 2018100843 A4 AU2018100843 A4 AU 2018100843A4 AU 2018100843 A AU2018100843 A AU 2018100843A AU 2018100843 A AU2018100843 A AU 2018100843A AU 2018100843 A4 AU2018100843 A4 AU 2018100843A4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
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Abstract
Organic intermediates oxalic acid aldehydes synthesis method Abstract 5 The present invention discloses organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature, adds sodium nitrate solution, controls the stirring speed, react, then the butenoic acid ethyl ester solution is added and the reaction is continued, the temperature is increased, adds 10 tetrakis (triphenylphosphine) platinum powder, continues to react, and then reduces the temperature, washed with potassium chloride solution for several times, washed with the dichloromethane solution for several times and washed with the dichloroacetonitrile solution for several times, recrystallized from the 2-hexanol solution, and the dehydrated with dehydrating agent, obtained the finished product 15 oxalic acid aldehyde. Figure 1
Description
The present invention discloses organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature, adds sodium nitrate solution, controls the stirring speed, react, then the butenoic acid ethyl ester solution is added and the reaction is continued, the temperature is increased, adds tetrakis (triphenylphosphine) platinum powder, continues to react, and then reduces the temperature, washed with potassium chloride solution for several times, washed with the dichloromethane solution for several times and washed with the dichloroacetonitrile solution for several times, recrystallized from the 2-hexanol solution, and the dehydrated with dehydrating agent, obtained the finished product oxalic acid aldehyde.
Figure 1
2018100843 20 Jun 2018
Organic intermediates oxalic acid aldehydes synthesis method
FIELD OF THE INVENTION
The present invention relates to a method for preparing a pharmaceutical 5 intermediate which belongs to the field of organic synthesis, more particularly, relates to organic intermediates oxalic acid aldehydes synthesis method.
GENERAL BACKGROUND
Oxalic acid aldehyde is mainly used as organic intermediates and organic synthesis materials, most of the existing synthesis methods using the process that tetracyanoethylene react with ozone oxidation in acetic acid. This synthesis method requires the use of tetracycladecene as one of the reactants, but tetracyanoethylene is a highly toxic substance, the reaction is more harmful the reaction operator, and the reaction process is complicated and the treatment cost is higher, acetic acid is highly corrosive on the reaction equipment, ozone has a strong ability to oxidize the equipment and later maintenance costs are higher, these factors will lead to increased production costs, and the synthesis method is complicated and the final yield is not very high. Therefore, it is necessary to propose a new synthesis method.
SUMMARY
Based on the technical problems of the background technology, the purpose of the present invention is to provide organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:
A: ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature to 40-46 °C in 30-50 min, adds sodium nitrate solution, controls the stirring speed at 190-220 rpm, react for 2-3 h, then the butenoic acid ethyl ester solution is added and the reaction is continued for 50-80 min.
B: the temperature is increased to 50-57 °C, adds tetrakis (triphenylphosphine) platinum powder, continues to react for 90-120 min, and then reduces the temperature to 10-16 °C, washed with potassium chloride solution for several times, washed with the die hloro methane solution for several times and washed with the dichloroacetonitrile solution for several times, recrystallized from the 2-hexanol
2018100843 20 Jun 2018 solution* and the dehydrated with dehydrating agent, obtained the Finished product oxalic acid aldehyde.
Preferably* the Sodium nitrate solution has a mass fraction of 15-22%.
Preferably* the mass fraction of the butenoic acid ethyl ester solution is 35-41%.
Preferably* the potassium chloride solution has a mass fraction of 10-16%.
Preferably* the dichloromelhane solution has a mass fraction of 40-45%.
Preferably* the mass fraction οΓdichloroacetonitrile solution is 50-57%».
Preferably* the 2-hexano! solution has a mass fraction of 80-86%.
Throughout the reaction process can be the following reaction formula:
H2N
CH2 CHO
I + CjHiA + [(C6H,),P)4Pt -► I
IFF-**. CHO
NH2
Compared with the synthesis method disclosed in the background art, the invention provides organic intermediates oxalic acid aldehydes synthesis method* the use of telracyanoethylene as a reactant does not require the use of tetracyanoethyleiie Compounds to avoid the LOxic effects of tetracyanoethylene Compounds on the synthesis reaction operator and avoid the complex handling of contaminants during the reaction process, reducing the cost of treatment and avoiding higher corrosion resistance requirements that acetic acid acting on the reaction equipment, no use of ozone with a strong ability to do reactants, equipment maintenance costs is reduced later, reducing the synthesis of reduced costs* reducing intermediate links reaction.
decreasing the reaction time and improving the reaction yield, al the same time, the present invention provides a new synthetic route which has laid a good foundation for Further enhancing the yield of the reaction.
DESCRIPTION OF THE DRAWINGS
Figure 1 is the infrared analysis Spectrum of finished product oxalic acid aldehydes.
2018100843 20 Jun 2018
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
Embodiment 1
Organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:
A: 2 mol ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature to 40 °C in 30 min, adds 1.3L sodium nitrate solution with a mass fraction of 15%, controls the stirring speed at 190 rpm, react for 2 h, then 4mol butenoic acid ethyl ester solution with a mass fraction of 35% is added and the reaction is continued for 50 min.
B: the temperature is increased to 50 °C, adds 2mol tetrakis (triphenylphosphine) platinum powder, continues to react for 90 min, and then reduces the temperature to 10 °C, washed with potassium chloride solution with a mass fraction of 10% for 3 times, washed with the diehloromethane solution with a mass fraction of 40% for 6 times and washed with the dichloroacetonitrile solution with a mass fraction of 50% for 2 times, recrystallized from the 2-hexanol solution with a mass fraction of 80%, and the dehydrated with activated alumina dehydrating agent, obtained the finished product oxalic acid aldehyde 103.24g, yield 89%.
Embodiment 2
Organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:
A: 2 mol ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature to 43 °C in 40 min, adds 1.3L sodium nitrate solution with a mass fraction of 17%, controls the stirring speed at 200 rpm, react for 2.5 h, then 5mol butenoic acid ethyl ester solution with a mass fraction of 38% is added and the reaction is continued for 65 min.
B: the temperature is increased to 54 °C, adds 2.5mol tetrakis (triphenylphosphine) platinum powder, continues to react for 100 min, and then reduces the temperature to
2018100843 20 Jun 2018
13°C, washed with potassium chloride solution with a mass fraction of 13% for 4 times, washed with the dichloromethane solution with a mass fraction of 43% for 7 times and washed with the dichloroacetonitrile solution with a mass fraction of 53% for 3 times, recrystallized from the 2-hexanol solution with a mass fraction of 83%, and the dehydrated with anhydrous calcium chloride dehydrating agent, obtained the finished product oxalic acid aldehyde 106.72g, yield 92%.
Embodiment 3
Organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:
A: 2 mol ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature to 46 °C in 50 min, adds 1.3L sodium nitrate solution with a mass fraction of 22%, controls the stirring speed at 220 rpm, react for 3 h, then 6mol butenoic acid ethyl ester solution with a mass fraction of 41% is added and the reaction is continued for 80min.
B: the temperature is increased to 57 °C, adds 3mol tetrakis (triphenylphosphine) platinum powder, continues to react for 120 min, and then reduces the temperature to 16°C, washed with potassium chloride solution with a mass fraction of 16% for 5 times, washed with the dichloromethane solution with a mass fraction of 45% for 8 times and washed with the dichloroacetonitrile solution with a mass fraction of 57% for 3 times, recrystallized from the 2-hexanol solution with a mass fraction of 86%, and the dehydrated with anhydrous sodium sulfate dehydrating agent, obtained the finished product oxalic acid aldehyde 109.04g, yield 94%.
Infrared analysis of finished product oxalic acid aldehyde, infrared spectrum is shown in figure 1, the analysis of data is shown in Table 1.
Table 1 Peak data
| Serial number | Peak position (cnf1) | Transmittance (%) | Half width (cnf1) | Peak difference (%) |
| 1 | 1722 | 9 | 31 | 85 |
| 2 | 2814 | 34 | 58 | 62 |
The embodiments of the present invention are merely preferred embodiments of the present invention, but the range of the present invention is not limited this, and any person who is familiar with those skilled in the arts, within the technical range of the present invention. It is intended that the technical solution and its inventive concept be replaced or modified equivalently with reference to the range of the invention.
2018100843 20 Jun 2018
2018100843 20 Jun 2018
Claims (3)
- Claims1. Organic intermediates oxalic acid aldehydes synthesis method, comprises the following steps:5 A: ethylenediamine is added to the reaction vessel, slowly raises the temperature, raises the temperature to 40-46 °C in 30-50 min, adds sodium nitrate solution, controls the stirring speed at 190-220 rpm, react for 2-3 h, then the butenoic acid ethyl ester solution is added and the reaction is continued for 50-80 min.B: the temperature is increased to 50-57 °C, adds tetrakis (triphenylphosphine)10 platinum powder, continues to react for 90-120 min, and then reduces the temperature to 10-16 °C, washed with potassium chloride solution for several times, washed with the die hloro methane solution for several times and washed with the dichloroacetonitrile solution for several times, recrystallized from the 2-hexanol solution, and the dehydrated with dehydrating agent, obtained the finished product15 oxalic acid aldehyde.
- 2. Organic intermediates oxalic acid aldehydes synthesis method according to claim 1 wherein the sodium nitrate solution has a mass fraction of 15-22%.
- 3. Organic intermediates oxalic acid aldehydes synthesis method according to claim 1 wherein the mass fraction of the butenoic acid ethyl ester solution is 35-41%.20 4. Organic intermediates oxalic acid aldehydes synthesis method according to claim 1 wherein the potassium chloride solution has a mass fraction of 10-16%.2018100843 20 Jun 20181/1Figure 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710710922.5A CN108238862A (en) | 2017-08-19 | 2017-08-19 | The synthetic method of organic intermediate glyoxal |
| CN2017107109225 | 2017-08-19 |
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| Publication Number | Publication Date |
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| AU2018100843A4 true AU2018100843A4 (en) | 2018-08-02 |
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| AU2018100843A Ceased AU2018100843A4 (en) | 2017-08-19 | 2018-06-20 | Organic intermediates oxalic acid aldehydes synthesis method |
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|---|---|
| CN (1) | CN108238862A (en) |
| AU (1) | AU2018100843A4 (en) |
| GB (1) | GB201713866D0 (en) |
| IE (1) | IES20180204A2 (en) |
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2017
- 2017-08-19 CN CN201710710922.5A patent/CN108238862A/en active Pending
- 2017-08-30 GB GBGB1713866.0A patent/GB201713866D0/en not_active Ceased
-
2018
- 2018-06-20 AU AU2018100843A patent/AU2018100843A4/en not_active Ceased
- 2018-06-26 IE IES20180204 patent/IES20180204A2/en not_active Application Discontinuation
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| Publication number | Publication date |
|---|---|
| CN108238862A (en) | 2018-07-03 |
| GB201713866D0 (en) | 2017-10-11 |
| IES20180204A2 (en) | 2019-11-13 |
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