CN107903146B - Method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene - Google Patents

Method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene Download PDF

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CN107903146B
CN107903146B CN201711181264.1A CN201711181264A CN107903146B CN 107903146 B CN107903146 B CN 107903146B CN 201711181264 A CN201711181264 A CN 201711181264A CN 107903146 B CN107903146 B CN 107903146B
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hexene
hydrogen peroxide
hexanediol
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formic acid
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CN107903146A (en
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杜中田
肖楚红
孙小万
李幸霏
鞠永伟
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Dalian University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
    • B01J2531/56—Vanadium

Abstract

The invention discloses a method for preparing 1, 2-hexadiene by catalytic oxidation of 1-hexeneThe alcohol method is technically characterized by comprising the following steps: formic acid is used as a reaction medium, hydrogen peroxide is used as an oxidant, the formic acid peroxide is obtained in situ, and the catalyst MVO is prepared2Oxidizing 1-hexene into an epoxy compound under the action of the dipic, and hydrolyzing, separating and purifying to obtain the 1, 2-hexanediol. The method has high catalytic efficiency and mild reaction conditions, the yield of the 1, 2-hexanediol reaches more than 85 percent, and the purity is more than 99 percent.

Description

Method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene
Technical Field
The invention belongs to the technical field of preparing aliphatic diol by olefin oxidation, and particularly relates to a method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene.
Background
The 1, 2-hexanediol has two hydroxyl functional groups at the 1 st and 2 nd positions of the carbon chain, is mutually soluble with water, can be mixed with various organic compounds in any proportion, has no corrosiveness and has antibacterial and anticorrosive activities, so that the 1, 2-hexanediol is widely applied to the manufacture of products such as high-grade cosmetics, multipurpose high-grade detergents, printing ink, paint and the like, and is an important fine chemical raw material.
The epoxidation hydrolysis of 1-hexene as raw material and hydrogen peroxide as oxidant is one of the important methods for preparing 1, 2-hexanediol. Patent CN1465556 reports that 1-hexene is used as raw material, organic acid is used as solvent, peroxide is used as oxidant, and after oxidation reaction, alkali is added for hydrolysis to obtain crude product, then acid is added for reverse regulation to neutrality, and after extraction, drying and rectification, 1, 2-hexanediol with purity of more than 99% can be obtained, but the yield is only 75%. Patent CN106316783 mentions a method for preparing 1, 2-hexanediol by using a gas-liquid pipeline, which comprises using 1-hexene as a raw material, using organic acid peroxide as an oxidant, carrying out an epoxidation reaction in an anhydrous organic solvent, adding alkali for hydrolysis to obtain a 1, 2-hexanediol crude product, adding acid to adjust to neutrality, extracting, drying, and rectifying to obtain 1, 2-hexanediol, wherein the purity is greater than 99%, and the yield can reach 88%, but the method uses dichloromethane as a solvent and has high toxicity. Patent CN103570493 reports HCOOH and H2O2Reaction-forming HCOOOH as oxidant, [ (C)18H37)2N(CH3)2]3[PW4O16]Is a phase transfer catalyst, the 1, 2-hexanediol is synthesized by catalyzing and oxidizing 1-hexene, the purity is more than 99 percent, and the yield reaches 90.4 percent. Therefore, the method for synthesizing the 1, 2-hexanediol by using the hydrogen peroxide as the oxidant is an improved direction, and the synthesis method needs to be further developed.
Disclosure of Invention
The invention aims to provide a method for preparing 1, 2-hexanediol, which has high catalytic efficiency and mild reaction conditions.
The technical scheme of the invention is as follows:
a method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene, comprising the steps of:
firstly, adding formic acid, hydrogen peroxide and a catalyst into a reactor, stirring and heating to 30-60 ℃, adding 1-hexene into a reaction system, keeping the temperature constant, reacting for 0.5-2h at a constant temperature, and then continuing to react for 6-20h at room temperature; wherein the molar ratio of formic acid to 1-hexene is 1-12: 1, the mass percent of hydrogen peroxide in hydrogen peroxide is 10-50%, and the molar ratio of hydrogen peroxide to 1-hexene in hydrogen peroxide is 1-8: 1; the catalyst is MVO2The dosage of the catalyst is 0.1 to 0.5 percent of the mass of 1-hexene;
and step two, removing formic acid from the mixture obtained in the step one, and hydrolyzing and separating to obtain the 1, 2-hexanediol.
Preferably, the molar ratio of formic acid to 1-hexene in the first step is 2-10: 1.
Preferably, the mass percent of the hydrogen peroxide in the hydrogen peroxide is 20-40%.
Preferably, the molar ratio of the hydrogen peroxide to the 1-hexene in the hydrogen peroxide solution is 2-6: 1.
Preferably, the amount of the catalyst is 0.2 to 0.4 percent of the mass of the 1-hexene.
Further, the catalyst MVO2Cation M of dipic+Is NH4 +、Na+、K+、Cs+A mixture of one or more of; dipic is a 2, 6-pyridinedicarboxylic acid ligand; anion of the bodySeed [ VO ]2dipic]-The structure of (A) is as follows:
Figure BDA0001479220630000021
further, the stirring speed in the first step is 300r/min-500 r/min.
Further, the catalyst MVO2The preparation method of the dipic comprises the following steps: weighing V2O5Dissolving dipicolinic acid in water, stirring, heating to 70 ℃, keeping the temperature for 4h, cooling to room temperature, filtering, adding hydrogen peroxide with the mass fraction of 30% into the filtrate, and adding saturated salt solution until precipitation is generated, wherein V2O5And dipicolinic acid in a mass ratio of 1:1 to 2, V2O5The mass ratio of the water to the water is 1: 10-50, V2O5The mass ratio of the hydrogen peroxide to the hydrogen peroxide is 2-4: 1, V2O5And the mass ratio of the saturated salt solution to the corresponding saturated salt solution is 1: 1-3. Then, the solution is cooled to 0 ℃, and the temperature is kept for 24 hours, filtered, washed and dried to obtain the catalyst.
Further, the second step is specifically that formic acid in the mixture obtained in the first step is evaporated under reduced pressure to obtain a transparent oily substance, and then 20% -30% of sodium hydroxide solution is added into the oily substance while stirring, and the pH value is adjusted to 10-12; cooling to room temperature, preserving heat for 2h, and adding hydrochloric acid to adjust the pH value to 7; adding saturated salt solution, standing for layering, extracting the upper oil phase (product) and the lower water phase with ethyl acetate, and mixing the oil phases; starting stirring and starting a condenser. Heating, distilling out ethyl acetate at normal pressure, and then distilling the product under reduced pressure.
The invention has the beneficial effects that: by MVO2dipic(M+＝NH4 +、Na+、K+、Cs+) The catalyst is used, wherein the dipic is a 2, 6-dipicolinic acid ligand, the hydrogen peroxide is an oxidant, and the 1, 2-hexanediol is prepared and synthesized by catalytic oxidation of 1-hexene, and the catalyst is added in the process synthesis method to shorten the reaction time; the ratio of formic acid to 1-hexene is reduced; the consumption of hydrogen peroxide is reduced; the process is simple; the reaction condition is mild, and the reaction efficiency is improved.
Drawings
FIG. 1 is a drawing of 1, 2-hexanediol1HNMR spectrogram.
FIG. 2 is a GC spectrum of 1, 2-hexanediol.
Detailed Description
The technical solutions of the present invention are described in detail below by examples, but the scope of the present invention is not limited thereto.
The invention selects the catalyst type, the molar ratio of raw materials, the catalyst dosage, the reaction temperature, the stirring speed, the hydrogen peroxide concentration and the like as the yield influencing factors of the 1, 2-hexanediol.
Examples 1 to 6: preparation methods of different catalysts: weighing V2O5Dissolving dipicolinic acid in water, stirring and heating to 70 ℃, preserving heat for 4h, cooling to room temperature, filtering, adding hydrogen peroxide with the mass fraction of 30% into the filtrate, adding saturated salt solution until precipitation is generated, then cooling the solution to 0 ℃, preserving heat for 24h, filtering, washing and drying to obtain the catalyst. Specific amounts are shown in the following table.
Figure BDA0001479220630000031
Figure BDA0001479220630000041
The molar ratio of formic acid to 1-hexene is 5: 1, the molar ratio of hydrogen peroxide to 1-hexene in hydrogen peroxide is 4:1, carrying out an experiment, wherein the using amount of the catalyst is 0.25%, the ratio of the components of the mixed catalyst is 1:1, stirring at a speed of 400r/min, heating to 45 ℃, adding 1-hexene into the system at a certain speed, keeping the temperature constant, reacting for 1 hour at a constant temperature, and then continuing to react for 10 hours at room temperature. After formic acid is removed from the reaction mixture, the 1, 2-hexanediol pure product is obtained after hydrolysis and separation by 30% sodium hydroxide solution. The yield of 1, 2-hexanediol was calculated by the internal standard method, as shown in the table
TABLE 1 influence of the catalyst type on the yield
Examples Catalyst numbering Purity of Yield of
1 ① 99％ 86.9
2 ② 99％ 87.8
3 ③ 99％ 87.4
4 ④ 99％ 87.2
5 ① and ④ 99％ 87.7
6 ② and ③ 99％ 87.3
Examples 7 to 12 experiments were carried out using hydrogen peroxide and 1-hexene in hydrogen peroxide at a molar ratio of 4:1 and formic acid and 1-hexene at different molar ratios, by adding formic acid, hydrogen peroxide at a concentration of 30% and catalyst ② to a reactor, stirring at a speed of 400r/min and heating to 45 ℃, adding 1-hexene to the system at a constant rate and keeping the temperature constant, reacting at constant temperature for 1 hour, continuing the reaction at room temperature for 10 hours, removing formic acid from the reaction mixture, hydrolyzing with 20% sodium hydroxide solution, separating to obtain a pure 1, 2-hexanediol, and calculating the yield of 1, 2-hexanediol by the internal standard method, as shown in table 2.
TABLE 2 Effect of different ratios of formic acid to 1-hexene on the yield
Examples Formic acid: 1-hexene Purity (%) Yield (%)
7 1：1 99 85.2
8 2：1 99 86.3
9 5：1 99 87.6
10 8：1 99 86.5
11 10：1 99 86.1
12 12：1 99 85.7
Examples 13 to 17 experiments were carried out using hydrogen peroxide and 1-hexene in hydrogen peroxide in different molar ratios with a molar ratio of formic acid to 1-hexene of 5: 1, adding formic acid, hydrogen peroxide in a concentration of 30% and a catalyst ③ to a reactor, stirring at a speed of 400r/min and heating to 45 ℃, adding 1-hexene to the system at a certain speed and keeping the temperature constant, reacting at a constant temperature for 1h, then continuing to react at room temperature for 10h, removing formic acid from the reaction mixture, hydrolyzing with a 30% sodium hydroxide solution, separating to obtain a pure product of 1, 2-hexanediol, and calculating the yield of 1, 2-hexanediol by an internal standard method, as shown in table 3.
TABLE 3 Effect of different ratios of hydrogen peroxide to 1-hexene on the yield
Examples Hydrogen peroxide: 1-hexene Purity (%) Yield (%)
13 1：1 99 85.8
14 2：1 99 86.3
15 4：1 99 87.2
16 6：1 99 86.1
17 8：1 99 85.0
Examples 18 to 23 experiments were carried out using a molar ratio of formic acid to 1-hexene of 5: 1 and a molar ratio of hydrogen peroxide to 1-hexene of 4:1 in hydrogen peroxide, wherein formic acid, hydrogen peroxide having a concentration of 30% and a catalyst ① were added to a reactor in an amount of 0.1% to 0.5%, the mixture was stirred at 400r/min and heated to 45 ℃, 1-hexene was added to the system at a constant rate while keeping the temperature constant, the reaction was carried out for 1 hour at a constant temperature, the reaction mixture was then reacted at room temperature for 10 hours, the formic acid was removed from the reaction mixture, and then a pure product of 1, 2-hexanediol was obtained by hydrolysis with a 30% sodium hydroxide solution and separation.
TABLE 4 Effect of different catalyst amounts on yield
Examples Amount of catalyst used Purity (%) Yield (%)
18 0.1％ 99 85.4
19 0.2％ 99 86.4
20 0.25％ 99 87.3
21 0.3％ 99 87.3
22 0.4％ 99 87.5
23 0.5％ 99 87.7
Examples 24 to 26 experiments were carried out using a molar ratio of formic acid to 1-hexene of 5: 1 and a molar ratio of hydrogen peroxide to 1-hexene of 4:1 in hydrogen peroxide, wherein formic acid, hydrogen peroxide having a concentration of 30% and a catalyst ② were added to a reactor, the amount of the catalyst was 0.25%, the mixture was stirred at a rate of 300r/min to 500r/min and heated to 45 ℃, 1-hexene was added to the system at a constant rate and the temperature was kept constant, the reaction was carried out at a constant temperature for 1 hour, then the reaction was continued at room temperature for 10 hours, the reaction mixture was freed from formic acid and hydrolyzed with a 30% sodium hydroxide solution, and the pure 1, 2-hexanediol was obtained after separation, and the yield of 1, 2-hexanediol was calculated by the internal standard method, as shown in table 5.
TABLE 5 influence of different stirring speeds on the yield
Examples Stirring speed (r/min) Purity (%) Yield (%)
24 300 99 85.5
25 400 99 87.5
26 500 99 86.1
Example 27-30 experiments were carried out using a formic acid to 1-hexene molar ratio of 5: 1, hydrogen peroxide to 1-hexene molar ratio in hydrogen peroxide of 4:1, adding formic acid, 30% hydrogen peroxide, and catalyst ④ to the reactor, stirring at 400r/min and heating to 30-60 ℃, adding 1-hexene to the system at a constant rate, maintaining the temperature constant, reacting at constant temperature for 1h, continuing to react at room temperature for 10h, removing formic acid from the reaction mixture, hydrolyzing with 30% sodium hydroxide solution, separating to obtain a pure product of 1, 2-hexanediol, and calculating the yield of 1, 2-hexanediol by internal standard method, as shown in table 6.
TABLE 6 influence of incubation reaction temperature on yield
Examples Reaction temperature (. degree.C.) Purity (%) Yield (%)
27 30 99 85.8
28 45 99 87.2
29 55 99 86.3
30 60 99 85.1
Examples 31 to 34 experiments were carried out using a molar ratio of formic acid to 1-hexene of 5: 1 and a molar ratio of hydrogen peroxide to 1-hexene of 4:1 in hydrogen peroxide, wherein formic acid, hydrogen peroxide having a concentration of 30% and a catalyst ③ were added to a reactor, the amount of the catalyst was 0.25%, the mixture was stirred at 400r/min and heated to 45 ℃, 1-hexene was added to the system at a constant rate and kept at a constant temperature for 1 hour, then the reaction was continued at room temperature for 6 to 20 hours, the reaction mixture was freed from formic acid and hydrolyzed with 30% sodium hydroxide solution, and the pure 1, 2-hexanediol was isolated, and the yield of 1, 2-hexanediol was calculated by the internal standard method, as shown in table 7.
TABLE 7 Effect of stirring time at room temperature on yield
Examples Reaction time (h) Purity (%) Yield (%)
31 6 99 85.1
32 10 99 87.6
33 15 99 86.8
34 20 99 85.6
In examples 35 to 39, experiments were carried out using a molar ratio of formic acid to 1-hexene of 5: 1 and a molar ratio of hydrogen peroxide to 1-hexene of 4:1 in hydrogen peroxide, in which formic acid, hydrogen peroxide having a concentration of 10% to 50% and a catalyst ④ were added to a reactor, the amount of the catalyst was 0.25%, the mixture was stirred at 400r/min and heated to 45 ℃, 1-hexene was added to the system at a constant rate while keeping the temperature constant, the reaction was carried out for 1 hour at a constant temperature, the reaction mixture was reacted for 10 hours at room temperature, the formic acid was removed from the reaction mixture, and then a pure product of 1, 2-hexanediol was obtained by hydrolysis and separation with a 30% sodium hydroxide solution, and the yield of 1, 2-hexanediol was calculated by the internal standard method, as shown in table 8.
TABLE 8 Effect of Hydrogen peroxide concentration on yield
Examples Hydrogen peroxide concentration (%) Purity (%) Yield (%)
35 10 99 85.5
36 20 99 86.8
37 30 99 87.8
38 40 99 86.6
39 50 99 85.6
Examples 40 to 43 experiments were carried out using a molar ratio of formic acid to 1-hexene of 5: 1 and a molar ratio of hydrogen peroxide to 1-hexene of 4:1 in hydrogen peroxide, wherein formic acid, hydrogen peroxide having a concentration of 30% and a catalyst ② were added to a reactor, the amount of the catalyst was 0.25%, the mixture was stirred at 400r/min and heated to 45 ℃, 1-hexene was added to the system at a constant rate while keeping the temperature constant, the reaction was carried out at a constant temperature for 0.5 to 2 hours, the reaction was continued at room temperature for 10 hours, the reaction mixture was subjected to formic acid removal, hydrolysis with a 30% sodium hydroxide solution and separation to obtain a pure product of 1, 2-hexanediol, and the yield of 1, 2-hexanediol was calculated by the internal standard method, as shown in table 9.
TABLE 9 influence of isothermal reaction time on the yield
Figure BDA0001479220630000081
Figure BDA0001479220630000091

Claims (6)

1. A method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene, which is characterized by comprising the following steps:
firstly, adding formic acid, hydrogen peroxide and a catalyst into a reactor, stirring and heating to 30-60 ℃, adding 1-hexene into a reaction system, keeping the temperature constant, reacting for 0.5-2h at a constant temperature, and then continuing to react for 6-20h at room temperature; wherein the molar ratio of formic acid to 1-hexene is 1-12: 1, the mass percent of hydrogen peroxide in hydrogen peroxide is 10-50%, and the molar ratio of hydrogen peroxide to 1-hexene in hydrogen peroxide is 1-8: 1; the catalyst is MVO2(dipic), the catalyst MVO2Cation of (dipic)M+Is NH4 +、Na+、K+、Cs+One or more of; dipic is a 2, 6-pyridinedicarboxylic acid ligand; anion [ VO2(dipic)]-The structure of (A) is as follows:
Figure FDA0002415219280000011
the dosage of the catalyst is 0.1-0.5 percent of the mass of 1-hexene;
and step two, removing formic acid from the mixture obtained in the step one, and hydrolyzing and separating to obtain the 1, 2-hexanediol.
2. The method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene according to claim 1, wherein the stirring speed in the first step is 300r/min to 500 r/min.
3. The method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene according to claim 1, wherein the molar ratio of formic acid to 1-hexene in step one is 2-10: 1.
4. The method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene according to claim 1 or 3, wherein the hydrogen peroxide content in hydrogen peroxide is 20-40% by weight.
5. The method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene according to claim 1 or 3, wherein the molar ratio of hydrogen peroxide to 1-hexene in hydrogen peroxide is 2-6: 1.
6. The method for preparing 1, 2-hexanediol by catalytic oxidation of 1-hexene according to claim 1, wherein the amount of the catalyst is 0.2% to 0.4% by mass of 1-hexene.
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