CN112479890A - Preparation method of nitro compound - Google Patents

Preparation method of nitro compound Download PDF

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CN112479890A
CN112479890A CN202011358027.XA CN202011358027A CN112479890A CN 112479890 A CN112479890 A CN 112479890A CN 202011358027 A CN202011358027 A CN 202011358027A CN 112479890 A CN112479890 A CN 112479890A
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compound
reaction
nitro compound
nitro
structure shown
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CN112479890B (en
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袁永坤
蒋玉贵
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Suzhou Yacoo Science Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/26—Halogenosulfates, i.e. monoesters of halogenosulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a preparation method of a nitro compound, which comprises the following preparation steps: reacting the compound 1A with the compound 1B to obtain a compound 2A; and (3) reacting the compound 2A with a nitrating reagent to obtain a crude product of the nitro compound, and purifying to obtain a refined product of the nitro compound. According to the invention, a reagent with a low price is used as an initial raw material, a final product is obtained through two-step reaction, the reaction condition of each step is mild, the yield of the obtained nitro compound is high, and the cost can be greatly reduced.

Description

Preparation method of nitro compound
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of a nitro compound.
Background
Nitro compounds are compounds in which one or more hydrogen atoms in the hydrocarbon molecule are replaced by nitro groups (-NO)2) Derivatives formed after substitution. Because the nitro is a strong electron-withdrawing group, the nitro compound has large dipole moment, large polarity, large intermolecular attraction force and boiling point ratioThe halogenated hydrocarbon should be high.
The liquid nitro compound is a good organic solvent and has certain chemical stability, so the nitro compound is often used as a solvent or additive for some organic reactions, such as 2-nitropropane, which is used as a special solvent for ethylene and epoxy resin coatings, an additive for rocket dyes, gasoline and the like, is also used for organic synthesis, has strong dissolving capacity, is a good solvent for various cellulose derivatives, vinyl resins and the like, and is also used as a solvent for wax, fat, dyes and the like, a lubricant for grinding pigments, and a cleaning and mordant for cotton fabrics.
At present, few reports on the synthesis of nitro compounds exist, and the preparation method of the nitro compounds mainly comprises a propane nitration method and can also be obtained by propylene nitration. However, the reaction process of the method adopts high temperature and high pressure, and the separation of the product is difficult, and the environmental pollution is serious.
Therefore, the method for preparing the nitro compound has great significance for seeking a new method for preparing the nitro compound, optimizing the preparation process, reducing the production cost and improving the yield.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of a nitro compound, which uses a reagent with lower price as an initial raw material, has mild reaction conditions, high yield of the obtained nitro compound and can greatly reduce the cost. After the crude product of the nitro compound with the general formula structure shown in the formula I obtained by the preparation method is purified, a refined product of the nitro compound with the general formula structure shown in the formula I is obtained.
The invention is realized by adopting the following technical scheme:
a preparation method of nitro compounds comprises the following preparation steps:
preparation step S1: reacting the compound 1A with the compound 1B to obtain a compound 2A;
preparation step S2: reacting the compound 2A with a nitrating reagent to obtain a nitro compound with a general structure shown as a formula I:
Figure BDA0002803160130000021
wherein, the compound 1A is
Figure BDA0002803160130000022
Figure BDA0002803160130000023
One or more of the combination of (A), X is halogen, R1、R2Respectively saturated or unsaturated, straight-chain or branched, heteroatom-containing or heteroatom-free C1-C30One of the hydrocarbon groups;
the compound 1B is one or a combination of a plurality of carbonyl-containing compounds, sulfuryl-containing compounds, sulfinyl-containing compounds and phosphoryl-containing compounds.
Preferably, the compound 1B is one or a combination of sulfuric acid, sulfurous acid, carbonic acid, sulfuryl halide, thionyl halide, carbonyl halide, diphosgene, triphosgene, N' -carbonyldiimidazole, phosphoric acid and phosphorus trihaloxide.
Preferably, the nitrating agent is nitrite, nitrous acid, NO2One or a combination of several of them.
Further, the compound 2A is at least one of an intermediate 2A1, an intermediate 2A2, an intermediate 2A3, an intermediate 2A4 and an intermediate 2A 5;
intermediate 2a1 is a compound having the general structure shown in formula ii:
Figure BDA0002803160130000031
intermediate 2a2 is a compound having the general structure shown in formula iii:
Figure BDA0002803160130000032
intermediate 2a3 is a compound having the general structure shown in formula iv:
Figure BDA0002803160130000033
intermediate 2a4 is a compound having the general structure shown in formula v:
Figure BDA0002803160130000034
intermediate 2a5 is a compound having the general structure shown in formula vi:
Figure BDA0002803160130000041
a is one element of N, O, S;
y is one element of P, S, C; n is 1 or 2;
wherein, in the formulas IV, V and VI corresponding to the intermediate 2A3, the intermediate 2A4 and the intermediate 2A5 respectively, Z is1、Z2Are respectively hydrogen atom, hydroxyl and C1-C30One of alkyl, SH, OR, SR, OM, SM and halogen; r in OR and SR is C which is saturated OR unsaturated, contains straight chain OR branched chain, contains heteroatoms OR does not contain heteroatoms1-C30One of the hydrocarbon groups; m in OM and SM is metal element cation, inorganic ammonium salt cation, organic ammonium salt cation, phosphorus salt cation,
Figure BDA0002803160130000048
One of a salt positive ion and an onium salt positive ion;
when n is 1, Y is S,
Figure BDA0002803160130000042
is composed of
Figure BDA0002803160130000043
When n is 1, Y is C,
Figure BDA0002803160130000044
is composed of
Figure BDA0002803160130000045
When n is 1, Y is P,
Figure BDA0002803160130000046
is composed of
Figure BDA0002803160130000047
When n is 2, Y is S,
Figure BDA0002803160130000051
is composed of
Figure BDA0002803160130000052
Further, the molar ratio of the compound 1A to the compound 1B is 1: 0.1-10; the molar ratio of the compound 2A to the nitrating reagent is 1: 0.1-10.
Further, the reaction conditions in the preparation step S1 are: the reaction temperature is-50 ℃ to 200 ℃, the reaction pressure is-0.05 MPa to 1MPa, and the reaction time is 0.1h to 72 h.
Further, the reaction conditions in the preparation step S2 are: the reaction temperature is-50 ℃ to 200 ℃, the reaction pressure is-0.05 MPa to 1MPa, and the reaction time is 0.1h to 72 h.
Further, the reaction of the preparation step S1 is carried out in a first reaction solvent; the first reaction solvent is one or a combination of more of methanol, ethanol, acetone, tetrahydrofuran, ethyl acetate, dimethyl carbonate, diethyl ether, acetonitrile, 1, 2-dichloroethane, dioxane, N-dimethylformamide, dimethyl sulfoxide and water.
Further, the reaction of the preparation step S2 is carried out in a second reaction solvent; the second reaction solvent is one or a combination of more of methanol, ethanol, acetone, tetrahydrofuran, ethyl acetate, dimethyl carbonate, diethyl ether, acetonitrile, 1, 2-dichloroethane, dioxane, N-dimethylformamide, dimethyl sulfoxide and water.
Further, the preparation method of the nitro compound also comprises the following preparation steps:
under the drying condition, dissolving the crude nitro compound in a purification solvent, recrystallizing at low temperature, filtering to remove insoluble substances, and performing rotary evaporation and drying on the filtrate to obtain a refined nitro compound; wherein the purifying solvent is one or more of methanol, ethanol, acetone, tetrahydrofuran, ethyl acetate, dimethyl carbonate, diethyl ether, acetonitrile, dioxane, N-dimethylformamide, dimethyl sulfoxide and water.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, a reagent with a low price is used as an initial raw material, a final product is obtained through two-step reaction, the reaction condition of each step is mild, the yield of the obtained nitro compound is high, and the cost can be greatly reduced.
The whole preparation process is simple and easy to control, is favorable for enlarging production, shortens the reaction production period, can obtain the nitro compound with higher purity, and can effectively improve the yield of the product.
Detailed Description
The invention will now be further described with reference to specific embodiments, which are intended to illustrate the invention in more detail by way of some non-limiting examples. It should be noted that these examples should not be construed as limiting the scope of the invention, which can be implemented in any manner described in the summary of the invention. The pressure values mentioned in the patent of the invention are gauge pressures unless otherwise specified. The yield in the invention refers to the percentage ratio of the actual product quality to the theoretical product quality; wherein, the theoretical product quality is calculated by the raw materials which are not excessive in the reaction equation. The purification yield in the examples of the present invention refers to the number of moles of the refined nitro compound after purification divided by the number of moles of the crude nitro compound before purification.
The following are specific examples of the present invention, and raw materials, equipment, and the like used in the following examples can be obtained by purchasing, unless otherwise specified.
Example 1
The preparation method of the 2-nitropropane comprises the following preparation steps:
adding 42g of compound 1A isopropanol and compound 1B sulfuric acid into a stainless steel reaction kettle in sequence, wherein the molar ratio of the compound 1A to the compound 1B is 1:1.1, uniformly stirring, and reacting for 24 hours at the temperature of 100 ℃ and the pressure of 0.1MPa to obtain a compound 2A;
adding a nitrating reagent sodium nitrite into a compound 2A, wherein the molar ratio of the compound 2A to the nitrating reagent is 1:3, reacting for 48 hours at the temperature of 60 ℃ and under the pressure of 0MPa to obtain crude 2-nitropropane, wherein the total yield is about 73.6%;
under the drying condition, 50g of crude 2-nitropropane is dissolved in 400ml of ethanol, low-temperature recrystallization is carried out, filtration is carried out again to remove insoluble substances, then the filtrate is added into a rotary evaporator and rotary evaporation is carried out for 1h at about 100 ℃, and then drying is carried out for 2h in a blast oven at 100 ℃ to obtain refined 2-nitropropane, wherein the purification yield is about 87.3%.
Example 2
The preparation method of the 2-nitrobutane comprises the following preparation steps:
sequentially adding 32g of compound 1A 2-butanol and compound 1B sulfuryl chloride into a stainless steel reaction kettle, wherein the molar ratio of the compound 1A to the compound 1B is 1:1.3, uniformly stirring, and reacting for 24 hours at 80 ℃ and 0.2MPa to obtain a compound 2A;
adding a nitrating reagent potassium nitrite into a compound 2A, wherein the molar ratio of the compound 2A to the nitrating reagent is 1:8, reacting for 48 hours at the temperature of 60 ℃ and under the pressure of 0.1MPa to obtain crude 2-nitrobutane with the total yield of about 79.5%;
under the drying condition, 50g of crude 2-nitrobutane is dissolved in 400ml of ethanol, low-temperature recrystallization is carried out, filtration is carried out again to remove insoluble substances, then the filtrate is added into a rotary evaporator and rotary evaporation is carried out for 1h at about 100 ℃, and then drying is carried out for 2h in a blast oven at 100 ℃ to obtain refined 2-nitrobutane, wherein the purification yield is about 88.1%.
Example 3
The preparation method of the 2-nitropentane comprises the following preparation steps:
sequentially adding 118g of compound 1A 2-pentanol and compound 1B triphosgene into a stainless steel reaction kettle, wherein the molar ratio of the compound 1A to the compound 1B is 1:1.2, uniformly stirring, and reacting for 24 hours at the temperature of 120 ℃ and the pressure of 0.3MPa to obtain a compound 2A;
adding a nitrating reagent nitrous acid into a compound 2A, wherein the molar ratio of the compound 2A to the nitrating reagent is 1:7, reacting for 48 hours at the temperature of 60 ℃ and under the pressure of 0.2MPa to obtain crude 2-nitropentane with the total yield of about 80.1%;
under the drying condition, 50g of crude 2-nitropentane is dissolved in 400ml of ethanol, low-temperature recrystallization is carried out, filtration is carried out again to remove insoluble substances, then the filtrate is added into a rotary evaporator and rotary evaporation is carried out for 1h at about 100 ℃, and then drying is carried out for 2h in a blast oven at 100 ℃ to obtain refined 2-nitropentane, wherein the purification yield is about 84.5%.
The above embodiments are only a part of the preferred embodiments of the present invention, and the embodiments are described only for illustrating the principle of the present invention, and thus the scope of the present invention is not limited by the embodiments. As will be apparent to those skilled in the art, numerous changes, modifications and variations can be made in the present invention without departing from the spirit, principles and scope of the invention, the invention resides in the claims hereinafter appended, and the invention includes all such changes, modifications and variations.

Claims (10)

1. The preparation method of the nitro compound is characterized by comprising the following preparation steps:
preparation step S1: reacting the compound 1A with the compound 1B to obtain a compound 2A;
preparation step S2: reacting the compound 2A with a nitrating reagent to obtain a nitro compound with a general structure shown as a formula I:
Figure FDA0002803160120000011
wherein, the compound 1A is
Figure FDA0002803160120000012
Figure FDA0002803160120000013
One or more of the combination of (A), X is halogen, R1、R2Respectively saturated or unsaturated, straight-chain or branched, heteroatom-containing or heteroatom-free C1-C30One of the hydrocarbon groups;
the compound 1B is one or a combination of a plurality of carbonyl-containing compounds, sulfuryl-containing compounds, sulfinyl-containing compounds and phosphoryl-containing compounds.
2. The method for preparing a nitro compound of claim 1, wherein the compound 2A has at least one structure selected from the group consisting of intermediate 2A1, intermediate 2A2, intermediate 2A3, intermediate 2A4 and intermediate 2A 5;
intermediate 2a1 is a compound having the general structure shown in formula ii:
Figure FDA0002803160120000021
intermediate 2a2 is a compound having the general structure shown in formula iii:
Figure FDA0002803160120000022
intermediate 2a3 is a compound having the general structure shown in formula iv:
Figure FDA0002803160120000023
intermediate 2a4 is a compound having the general structure shown in formula v:
Figure FDA0002803160120000024
intermediate 2a5 is a compound having the general structure shown in formula vi:
Figure FDA0002803160120000031
a is one element of N, O, S;
y is one element of P, S, C; n is 1 or 2;
wherein, in the formulas IV, V and VI corresponding to the intermediate 2A3, the intermediate 2A4 and the intermediate 2A5 respectively, Z is1、Z2Are respectively hydrogen atom, hydroxyl and C1-C30One of alkyl, SH, OR, SR, OM, SM and halogen; r in OR and SR is C which is saturated OR unsaturated, contains straight chain OR branched chain, contains heteroatoms OR does not contain heteroatoms1-C30One of the hydrocarbon groups; m in OM and SM is metal element cation, inorganic ammonium salt cation, organic ammonium salt cation, phosphorus salt cation,
Figure FDA0002803160120000038
One of a salt positive ion and an onium salt positive ion;
when n is 1, Y is S,
Figure FDA0002803160120000032
is composed of
Figure FDA0002803160120000033
When n is 1, Y is C,
Figure FDA0002803160120000034
is composed of
Figure FDA0002803160120000035
When n is 1, Y is P,
Figure FDA0002803160120000036
is composed of
Figure FDA0002803160120000037
When n is 2, Y is S,
Figure FDA0002803160120000041
is composed of
Figure FDA0002803160120000042
3. The method for preparing nitro compound according to claim 1, wherein the compound 1B is one or more of sulfuric acid, sulfurous acid, carbonic acid, sulfuryl halide, thionyl halide, carbonyl halide, diphosgene, triphosgene, N' -carbonyldiimidazole, phosphoric acid, and phosphorus trihaloxide.
4. The method for producing a nitro compound according to claim 1, wherein the nitrating agent is nitrite, nitrous acid, NO2One or a combination of several of them.
5. The method for preparing a nitro compound according to claim 1, wherein the molar ratio of the compound 1A to the compound 1B is 1: 0.1-10; the molar ratio of the compound 2A to the nitrating reagent is 1: 0.1-10.
6. The method for producing a nitro compound according to claim 1, wherein the reaction conditions in the production step S1 are: the reaction temperature is-50 ℃ to 200 ℃, the reaction pressure is-0.05 MPa to 1MPa, and the reaction time is 0.1h to 72 h.
7. The method for producing a nitro compound according to claim 1, wherein the reaction conditions in the production step S2 are: the reaction temperature is-50 ℃ to 200 ℃, the reaction pressure is-0.05 MPa to 1MPa, and the reaction time is 0.1h to 72 h.
8. The method for producing a nitro compound according to claim 1, wherein the reaction of the production step S1 is carried out in a first reaction solvent; the first reaction solvent is one or a combination of more of methanol, ethanol, acetone, tetrahydrofuran, ethyl acetate, dimethyl carbonate, diethyl ether, acetonitrile, 1, 2-dichloroethane, dioxane, N-dimethylformamide, dimethyl sulfoxide and water.
9. The method for producing a nitro compound according to claim 1, wherein the reaction of the production step S2 is carried out in a second reaction solvent; the second reaction solvent is one or a combination of more of methanol, ethanol, acetone, tetrahydrofuran, ethyl acetate, dimethyl carbonate, diethyl ether, acetonitrile, 1, 2-dichloroethane, dioxane, N-dimethylformamide, dimethyl sulfoxide and water.
10. The method for producing a nitro compound according to any one of claims 1 to 9, further comprising the production steps of:
under the drying condition, dissolving the crude nitro compound obtained in the preparation step S2 in a purification solvent, carrying out low-temperature recrystallization, filtering, removing insoluble substances, and then carrying out rotary evaporation and drying on the filtrate to obtain a refined nitro compound; wherein the purifying solvent is one or more of methanol, ethanol, acetone, tetrahydrofuran, ethyl acetate, dimethyl carbonate, diethyl ether, acetonitrile, dioxane, N-dimethylformamide, dimethyl sulfoxide and water.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113477227A (en) * 2021-07-30 2021-10-08 中国环境科学研究院 Preparation method of grafting reinforced biochar-based heavy metal adsorption material

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KR20200002720A (en) * 2019-10-11 2020-01-08 (주)에이에스텍 A preparing method of diethylamino hydroxybenzoyl hexylbenzoate

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Publication number Priority date Publication date Assignee Title
CN113477227A (en) * 2021-07-30 2021-10-08 中国环境科学研究院 Preparation method of grafting reinforced biochar-based heavy metal adsorption material
CN113477227B (en) * 2021-07-30 2022-02-01 中国环境科学研究院 Preparation method of grafting reinforced biochar-based heavy metal adsorption material

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