CN109369490B - Synthesis method of tert-butyl peroxycarbonate - Google Patents

Synthesis method of tert-butyl peroxycarbonate Download PDF

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CN109369490B
CN109369490B CN201811384668.5A CN201811384668A CN109369490B CN 109369490 B CN109369490 B CN 109369490B CN 201811384668 A CN201811384668 A CN 201811384668A CN 109369490 B CN109369490 B CN 109369490B
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tert
butyl
polyvinyl alcohol
amino acid
peroxycarbonate
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CN109369490A (en
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陈唐建
翟志强
许淑女
黄燕民
崔黎明
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Zibo Zhenghua Auxiliary Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/068—Polyalkylene glycols

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  • Organic Chemistry (AREA)
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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of tert-butyl peroxycarbonate. Adding organic formate, tert-butyl hydroperoxide and polyvinyl alcohol compound amino acid catalyst into an organic solvent, stirring and dehydrating to synthesize tert-butyl peroxycarbonate; the polyvinyl alcohol composite amino acid catalyst is obtained by polymerizing a spherical polyvinyl alcohol matrix and composite amino acid. In the production process of the peroxide, the invention avoids using expensive chemical raw material chloroformate, optimizes the synthesis process of the peroxide and reduces the discharge of waste water/waste solids containing chloride in the industrial production process.

Description

Synthesis method of tert-butyl peroxycarbonate
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of tert-butyl peroxycarbonate.
Background
Tert-butyl peroxycarbonate is an industrially important high-molecular polymerization initiator, and is particularly suitable for polyacrylate, polyethylene, polyvinyl chloride and polystyrene products. In industry, t-butyl peroxycarbonate is prepared from t-butyl hydroperoxide and the corresponding chloroformate. For example, t-butyl peroxyisopropyl carbonate is prepared by reacting hydrogen peroxide with 2-ethoxyethyl chloroformate under the action of sodium hydroxide.
CN107311906A discloses a production process of di-tert-butyl peroxide, hydrogen peroxide and tert-butyl alcohol react under the catalysis of sulfuric acid to obtain the di-tert-butyl peroxide in one step, so that the production period is shortened, the energy consumption is reduced, and the generation of waste sulfuric acid is reduced.
CN104557652A discloses a preparation method of tert-butyl peroxide, which comprises the steps of taking tert-butyl alcohol and hydrogen peroxide as raw materials, taking acidic ion exchange resin as a catalyst, carrying out reflux reaction, cooling, standing and separating to obtain separated oil phase and water phase; and (3) carrying out alkali washing and water washing on the oil phase to obtain a di-tert-butyl peroxide solution.
CN101298429A discloses a method for preparing tert-butyl hydroperoxide and di-tert-butyl peroxide, which comprises mixing sulfuric acid, hydrogen peroxide and phosphotungstic acid at certain concentration, and adding tert-butyl alcohol into the mixed solution, or adding the mixed solution into tert-butyl alcohol; reacting for 0.5-5 h at 20-60 ℃, and separating the crude reaction product to obtain an oil phase; the oil phase is rectified under reduced pressure to obtain tert-butyl hydroperoxide and di-tert-butyl peroxide products.
CN107056670A discloses a preparation method of di-tert-butyl peroxide, which is to return tert-butyl alcohol, hydrogen peroxide and a catalyst to a micro-reaction device in a continuous manner, so that the tert-butyl alcohol and the hydrogen peroxide are subjected to peroxidation to prepare a material flow containing di-tert-butyl peroxide, then the material flow containing the di-tert-butyl peroxide is led out from the micro-reaction device, and the di-tert-butyl peroxide is obtained through separation, water washing and drying.
CN105523982A discloses a preparation method of tert-butyl hydroperoxide, which comprises peroxidation and condensation reaction, concentrated sulfuric acid is used as a catalyst, hydrogen peroxide and tert-butyl alcohol are used for reaction for 0.5-4 h at 10-50 ℃, an organic phase of a reaction crude product is an intermediate product of tert-butyl hydroperoxide and a byproduct of di-tert-butyl peroxide, and the byproduct of di-tert-butyl peroxide is removed by a salt formation technology; adding 2-ethylhexyl chloroformate and sodium hydroxide solution as a catalyst into the inorganic phase, and reacting at 10-50 ℃ for 1.0-6 h to obtain tert-butyl peroxy-2-ethylhexyl carbonate.
CN105237453A discloses a method for preparing methyl ethyl ketone peroxide by using acidic ion exchange resin as a catalyst, which is to use butanone and hydrogen peroxide as raw materials, use acidic ion exchange resin as a catalyst, use dibutyl phthalate as a diluent, stir at a constant temperature for reaction, stand for separation, and obtain an oil phase, namely methyl ethyl ketone peroxide.
CN1871358A discloses a process for the production of hydrocarbons and oxygenates from biomass for the fermentation of plant-derived carbohydrate substrates to produce C1～C5Alcohols and synthesis of higher alcohols and other oxygenates. The synthetic raw materials are prepared biogas and C2～C5Alcohols in which the amino acids leucine, isoleucine and valine or mixtures thereof, optionally obtained from yeast autolysis, are used as biocatalysts during the fermentation stage.
It can be seen that a disadvantage of the above synthesis process is that the chloroformates themselves are expensive chemical starting materials; in addition, the use of chloroformates results in the formation of hydrogen chloride as a by-product, a corrosive substance; moreover, the use of chloroformates as raw materials also presents environmental problems in the form of chloride effluents/waste solids.
Disclosure of Invention
The invention aims to provide a synthesis method of tert-butyl peroxycarbonate, which is scientific, reasonable, simple and feasible, avoids using expensive chemical raw material chloroformate, and has good environmental protection effect.
The synthesis method of the tert-butyl peroxycarbonate comprises the following steps:
adding organic formate, tert-butyl hydroperoxide and polyvinyl alcohol compound amino acid catalyst into an organic solvent, stirring and dehydrating to synthesize tert-butyl peroxycarbonate;
the polyvinyl alcohol composite amino acid catalyst is obtained by polymerizing a spherical polyvinyl alcohol matrix and composite amino acid.
The spherical polyvinyl alcohol matrix is obtained by crosslinking polyvinyl alcohol and a crosslinking agent.
The polyvinyl alcohol is available in many grades, products such as 0588, 0599, 1788, 1799, 2088, 2099, 2488 and 2499 are generally selected, products such as 1788, 1799, 2088 and 2099 are preferably used, and a 2088 polyvinyl alcohol product is more preferably used.
The cross-linking agent is one or more of glutaraldehyde, terephthaldehyde or formaldehyde. As glutaraldehyde as the cross-linking agent has the advantages of high cross-linking speed, large cross-linking network, low toxicity and the like, glutaraldehyde is preferably used as the cross-linking agent in the invention.
The compound amino acid is two or more of cysteine, phenylalanine, alanine, methionine, glycine, glutamic acid, glutamine, arginine, lysine, tyrosine, leucine, aspartic acid, asparagine, proline, tryptophan, serine, threonine, valine, isoleucine or histidine; the preferable compound amino acid is two or more of cysteine, glutamic acid, arginine, aspartic acid, proline, glycine, tyrosine, histidine or serine.
More preferred complex amino acids of the invention are mixtures of cysteine, glutamic acid, arginine, aspartic acid and proline.
More preferred complex amino acids of the invention are mixtures of cysteine, glycine, tyrosine, proline and histidine.
More preferred complex amino acids of the invention are a mixture of cysteine, glutamic acid, arginine, serine and histidine.
The addition amount of the polyvinyl alcohol compound amino acid catalyst is 1-100% of the mass of the tert-butyl hydroperoxide.
The amount of polyvinyl alcohol complex amino acid catalyst added depends on several factors known to those skilled in the art of peroxide reactions, including the reactivity between t-butyl hydroperoxide and the organic formate; reaction conditions such as temperature and reaction time, and stirring speed, etc. In the present invention, the polyvinyl alcohol complex amino acid catalyst is preferably added in a proportion of 5 to 50% by mass, more preferably 15 to 25% by mass, based on the mass of t-butyl hydroperoxide added.
The specific preparation steps of the polyvinyl alcohol compound amino acid catalyst are as follows:
(1) dissolving polyvinyl alcohol in distilled water, stirring for 5 hours in a water bath at 100 ℃, cooling to room temperature, adding a cross-linking agent, and stirring to obtain a raw material A;
(2) adding a surfactant span80 into cyclohexane, and uniformly stirring to obtain a raw material B;
(3) adding the raw material A into a three-necked bottle, adding a hydrochloric acid solution, uniformly stirring, adding the raw material B, controlling the stirring speed at 400-600 r/min, reacting at room temperature for 4h, slowly heating to 70 ℃ for reacting for 4h, cooling, filtering, and washing to obtain a spherical polyvinyl alcohol matrix for later use.
(4) Adding dimethyl sulfoxide and a spherical polyvinyl alcohol matrix into a three-necked bottle, adding a compound amino acid, uniformly mixing, stirring and reacting for 8 hours at a constant temperature of 90-110 ℃, cooling, performing suction filtration, washing twice with ethanol, and drying to obtain the spherical polyvinyl alcohol compound amino acid catalyst with a catalytic active group.
The polyvinyl alcohol composite amino acid catalyst is prepared by taking polyvinyl alcohol as a raw material, utilizing a cross-linking agent to obtain spherical polyvinyl alcohol through inverse polymerization, and reacting the spherical polyvinyl alcohol with composite amino acid.
The organic solvent is petroleum ether or pentane.
The organic formate has a structural formula of R-O-C (═ O) -OH, wherein R is a straight chain or branched chain or C with an aromatic ring1～C16A group. The R group can be, but is not limited to, methyl, ethyl, propyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, t-pentyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, phenylpropyl, isooctyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, and the like.
The molar ratio of the tert-butyl hydroperoxide to the organic formate is 1: 10-5: 1.
In general, the tert-butyl hydroperoxide and the organic formate can be reacted in a wide range of molar ratios in order to increase the yield of the reaction product. In the process of the present invention, the reaction is preferably carried out with a molar ratio of hydrogen peroxide to organic formate of 1: 2.
The reaction temperature is-20-120 ℃, and the reaction time is 1-24 h.
According to the process of the present invention, the peroxide reaction can be carried out over a wide temperature range. The reaction temperature is usually controlled to be between-20 ℃ and 120 ℃, preferably between 0 ℃ and 60 ℃, more preferably between 20 ℃ and 40 ℃. The reaction temperature is usually varied according to the physicochemical properties of the product itself. The preferable reaction time is 4-8 h.
The dehydration is carried out by azeotropic distillation, molecular distillation, stripping with dry air or stripping with inert gas.
In the chemical reaction process of tert-butyl peroxycarbonate formed by the reaction of tert-butyl hydroperoxide and organic formate, water of reaction is generated. The reaction water is removed from the reaction mixture in time, for example by azeotropic distillation, molecular distillation, stripping with dry air or inert gas such as nitrogen for dehydration; azeotropic distillation, dry air or inert gas stripping such as nitrogen is preferred in the present invention; more preferably, the water of reaction is removed by azeotropic distillation.
The solvent for removing the reaction water by azeotropic distillation is benzene, toluene, xylene, ethylbenzene, butane, pentane, hexane, heptane, isoheptane, octane, isooctane, cyclopentane, cyclohexane, methylcyclopentane, methylcyclohexane, petroleum ether or light gasoline; preferably the solvents toluene, xylene, pentane, hexane, cyclopentane, cyclohexane, petroleum ether or light petrol; more preferably the solvent is pentane or petroleum ether.
The invention relates to a method for preparing tert-butyl peroxycarbonate by reacting organic formate with tert-butyl hydroperoxide under the action of a polyvinyl alcohol compound amino acid catalyst. T-butyl peroxycarbonate such as t-butyl peroxyisopropyl carbonate, t-butyl peroxy-2-ethylhexyl carbonate, etc.
The document "synthesis, structure and heavy metal chelating function of amino acid-containing epoxidized crosslinked polyvinyl alcohol" (Zhejiang university school report, 2009, 37(5): 515-. The invention firstly applies the polyvinyl alcohol compound amino acid catalyst in the field of catalytic synthesis of peroxide, and has innovation.
In the present invention, the amino acid-containing polyvinyl alcohols are all the same as the amino acid-containing polyvinyl alcohols of the prior art documents, but the chemical structures of the amino acid-containing polyvinyl alcohols are completely different from those of the prior art documents. The polyvinyl alcohol high-molecular chelating agent disclosed in the document 'synthesis, structure and heavy metal chelating function of amino acid-containing epoxidized crosslinked polyvinyl alcohol' is formed by connecting polyvinyl alcohol and amino acid together through epichlorohydrin.
The invention discloses a novel method for synthesizing a peroxide by using polyethylene spheres containing a specific combination of amino acids. Compared with amino acid or amino acid mixture, the combination of the combined amino acid and polyvinyl alcohol is the key of the catalysis of the polyethylene ball containing the specific combined amino acid, and the preferable combination of several amino acids has the synergistic catalysis effect of amino, carboxyl, hydroxyl and sulfydryl contained in the catalyst ball in a special space to catalyze the synthesis of peroxide.
The invention has the following beneficial effects:
in the production process of the peroxide, the invention avoids using expensive chemical raw material chloroformate, optimizes the synthesis process of the peroxide and reduces the discharge of waste water/waste solids containing chloride in the industrial production process.
Detailed Description
The present invention is further described below with reference to examples.
And 5, mixing one part of each of five amino acids including cysteine, glutamic acid, arginine, aspartic acid and proline to obtain the compound amino acid A.
And (3) mixing one part of each of five amino acids of cysteine, glycine, tyrosine, proline and histidine to obtain the compound amino acid B.
And mixing one part of each of five amino acids including cysteine, glutamic acid, arginine, serine and histidine to obtain the compound amino acid C.
The polyvinyl alcohol compound amino acid catalyst is synthesized by the following method:
(1) dissolving 10g of polyvinyl alcohol (2088) in 200ml of distilled water, stirring for 5h in a water bath at 100 ℃, cooling to room temperature, adding 2.1ml of glutaraldehyde solution (50%), and stirring to obtain a raw material A;
(2) adding 4g of surfactant span80 into 600ml of cyclohexane, and uniformly stirring to obtain a raw material B;
(3) adding the raw material A into a 2000ml three-necked bottle, adding 14ml hydrochloric acid solution (0.1mol/L), uniformly stirring, adding the raw material B, controlling the stirring speed at 400-600 r/min, reacting at room temperature for 4h, slowly heating to 70 ℃ for reacting for 4h, cooling, filtering, and washing to obtain spherical polyvinyl alcohol for later use.
(4) Adding 200mL of dimethyl sulfoxide and 10g of spherical polyvinyl alcohol into a 500mL three-necked bottle, adding 5.1g of compound amino acid A, uniformly mixing, stirring and reacting for 8 hours at a constant temperature of 90-110 ℃, cooling, performing suction filtration, washing twice with ethanol, and drying to obtain the spherical polyvinyl alcohol compound amino acid catalyst A with a catalytic active group.
(5) Adding 200mL of dimethyl sulfoxide and 10g of spherical polyvinyl alcohol into a 500mL three-necked bottle, adding 4.8g of compound amino acid B, uniformly mixing, stirring and reacting at a constant temperature of 90-110 ℃ for 8h, cooling, performing suction filtration, washing with ethanol twice, and drying to obtain the spherical polyvinyl alcohol compound amino acid catalyst B with a catalytic active group.
(6) Adding 100mL of dimethyl sulfoxide and 10g of spherical polyvinyl alcohol into a 500mL three-necked bottle, adding 5.2g of compound amino acid C, uniformly mixing, stirring at a constant temperature of 90-110 ℃ for reacting for 8 hours, cooling, performing suction filtration, washing with ethanol twice, and drying to obtain the spherical polyvinyl alcohol compound amino acid catalyst C with a catalytic active group.
Example 1
200ml of petroleum ether (60-90 ℃) is added into a 500ml three-neck flask, 44g of tert-butyl hydroperoxide with the purity of 70 percent is added, 30g of isopropyl formic acid is added, and 6g of spherical polyvinyl alcohol composite amino acid A is added. Stirring the reaction mixture and heating to reflux temperature of 70-80 ℃. After azeotropic distillation, the distillate was cooled and the water of reaction was removed in a water separator. The petroleum ether is separated off and returned to the reaction vessel. After 4h of reaction, the product yield of t-butylperoxyisopropyl carbonate was 91.2% as determined by gas chromatography.
Example 2
Into a 500ml three-necked flask, 200ml of pentane was charged, 44g of t-butyl hydroperoxide having a purity of 70% was charged, 30g of isopropyl formic acid was charged, and 2g of spherical polyvinyl alcohol complex amino acid B was charged. Stirring the reaction mixture and heating to reflux temperature of 70-80 ℃. After azeotropic distillation, the distillate was cooled and the water of reaction was removed in a water separator. The pentane is separated off and returned back to the reaction vessel. After 4h of reaction, the product yield of t-butylperoxyisopropyl carbonate was 84.9% as determined by gas chromatography.
Example 3
Into a 500ml three-necked flask, 200ml of pentane was charged, 44g of t-butyl hydroperoxide having a purity of 70% was charged, 30g of isopropyl formic acid was charged, and 4g of spherical polyvinyl alcohol complex amino acid C was charged. Stirring the reaction mixture and heating to reflux temperature of 70-80 ℃. After azeotropic distillation, the distillate was cooled and the water of reaction was removed in a water separator. The pentane is separated off and returned back to the reaction vessel. After 4h of reaction, the yield of t-butylperoxyisopropyl carbonate product was 88.2% as determined by gas chromatography.
Example 4
Into a 500ml three-necked flask, 200ml of pentane was charged, 40g of t-butyl hydroperoxide having a purity of 70% was charged, 54g of 2-ethylhexyl carbonate was charged, and 4g of spherical polyvinyl alcohol composite amino acid A was charged. Stirring the reaction mixture and heating to reflux temperature of 70-80 ℃. After azeotropic distillation, the distillate was cooled and the water of reaction was removed in a water separator. The pentane is separated off and returned back to the reaction vessel. After 4h of reaction, the product yield of t-butylperoxy-2-ethylhexyl carbonate was 90.6% as determined by gas chromatography.
Example 5
Into a 500ml three-necked flask, 200ml of pentane was charged, 40g of t-butyl hydroperoxide having a purity of 70% was charged, 54g of 2-ethylhexyl carbonate was charged, and 8g of spherical polyvinyl alcohol complex amino acid B was charged. Stirring the reaction mixture and heating to reflux temperature of 70-80 ℃. After azeotropic distillation, the distillate was cooled and the water of reaction was removed in a water separator. The pentane is separated off and returned back to the reaction vessel. After 4h of reaction, the product yield of t-butylperoxy-2-ethylhexyl carbonate was 94.3% as determined by gas chromatography.
Example 6
Into a 500ml three-necked flask, 200ml of pentane was charged, 40g of t-butyl hydroperoxide having a purity of 70% was charged, 54g of 2-ethylhexyl carbonate was charged, and 2g of spherical polyvinyl alcohol complex amino acid C was charged. Stirring the reaction mixture and heating to reflux temperature of 70-80 ℃. After azeotropic distillation, the distillate was cooled and the water of reaction was removed in a water separator. The pentane is separated off and returned back to the reaction vessel. After 4h of reaction, the product yield of t-butylperoxy-2-ethylhexyl carbonate was 66.2% as determined by gas chromatography.
Comparative example 1
Adding 100g of 25 percent sodium hydroxide solution into a 500ml three-necked bottle, stirring and cooling to 5 ℃; dropwise adding 40g of hydrogen peroxide with the purity of 27.5%, reacting for 30 minutes, and controlling the temperature to be 0-30 ℃; after the mixture is stirred uniformly, 150g of mixed solution of 62% 2-ethoxyethyl chloroformate and solvent oil is slowly dripped into a three-necked bottle, the reaction temperature is controlled to be 10-30 ℃, the mixed solution is added after 1.5 hours, and the mixed solution is stirred and reacted for 30 minutes after the 2-ethoxyethyl chloroformate solution is added; stopping stirring after the reaction is finished, standing for 40 minutes, separating out reaction mother liquor, and washing a reaction product until the pH value is 5-7; 130.6g of bis (2-ethoxy) ethyl peroxydicarbonate with a content of 55.6% was obtained, with a yield of 83%.

Claims (6)

1. A synthesis method of tert-butyl peroxycarbonate is characterized by comprising the following steps:
adding organic formate, tert-butyl hydroperoxide and polyvinyl alcohol compound amino acid catalyst into an organic solvent, stirring and dehydrating to synthesize tert-butyl peroxycarbonate;
the polyvinyl alcohol composite amino acid catalyst is obtained by polymerizing a spherical polyvinyl alcohol matrix and composite amino acid;
the spherical polyvinyl alcohol matrix is obtained by crosslinking polyvinyl alcohol and a crosslinking agent;
the cross-linking agent is glutaraldehyde;
the compound amino acid is a mixture of cysteine, glutamic acid, arginine, aspartic acid and proline, or a mixture of cysteine, glycine, tyrosine, proline and histidine, or a mixture of cysteine, glutamic acid, arginine, serine and histidine;
the structural formula of the organic formate is R-O-C (= O) -OH, wherein the R group is methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, amyl, isoamyl, tert-amyl or isooctyl.
2. The method for synthesizing tert-butyl peroxycarbonate according to claim 1, wherein the addition amount of the polyvinyl alcohol complex amino acid catalyst is 1-100% of the mass of tert-butyl hydroperoxide.
3. The method for synthesizing tert-butyl peroxycarbonate according to claim 1, wherein the organic solvent is petroleum ether or pentane.
4. The method for synthesizing tert-butyl peroxycarbonate according to claim 1, wherein the molar ratio of tert-butyl hydroperoxide to organic formate is 1:10 to 5: 1.
5. The method for synthesizing tert-butyl peroxycarbonate according to claim 1, wherein the reaction temperature is-20 to 120 ℃ and the reaction time is 1 to 24 hours.
6. The method for synthesizing t-butyl peroxycarbonate according to claim 1, wherein the dehydration is performed by azeotropic distillation, molecular distillation, stripping with dry air or stripping with inert gas.
CN201811384668.5A 2018-11-20 2018-11-20 Synthesis method of tert-butyl peroxycarbonate Active CN109369490B (en)

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