Catalytic oxidation method of n-pentene

Abstract

The invention discloses a catalytic oxidation method of n-pentene, and belongs to the technical field of fine chemical engineering. The n-pentene catalytic oxidation method comprises the following steps that n-pentene, a molecular sieve catalyst, a hydrogen peroxide solution and a cosolvent are mixed and react to obtain an n-pentene catalytic oxidation product, the cosolvent is selected from one or more of methyl alcohol, isopropyl alcohol, acetone and acetonitrile, and the n-pentene catalytic oxidation product is selected from propyl ethylene oxide and 1, 3-propylene glycol. The solvent is one or more of 1, 2-pentanediol, 1-methoxyl-2-pentanol and 2-methoxyl-1-pentanol, and the solvent is one or more of 1, 2-pentanediol, 1-methoxyl-2-pentanol and 2-methoxyl-1- According to the invention, the selectivity of the products propyl ethylene oxide, 1, 2-pentanediol, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol is controlled by adjusting the types of the cosolvents and reaction parameters, and one or more required n-pentene catalytic oxidation products can be prepared in the same reaction according to different industrial requirements.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of fine chemical technology, and in particular to a method for catalytic oxidation of n-pentene. BACKGROUND

[0002] Catalytic oxidation is a type of oxidation reaction that involves the use of metal catalysts such as platinum (Pt), palladium (Pd), nickel (Ni), copper (Cu), etc., in combination with oxidizing agents like air, oxygen, ozone, etc., under specific pressure and temperature conditions. This reaction includes two main processes: "oxygen addition" and "hydrogen removal". During catalytic oxidation, the catalyst changes the reaction pathway and rate, allowing the oxidation reaction to occur at lower temperatures and pressures, thereby improving the selectivity and efficiency of the reaction.

[0003] Olefin catalytic oxidation is an important method of organic synthesis that can convert colorless and odorless olefins into organic compounds containing multifunctional groups, such as ketones and aldehydes, under mild conditions.

[0004] 1,2-Pentanediol is a key intermediate for the synthesis of the fungicide propiconazole and an important raw material for the production of surfactants, polyester fibers, and pharmaceuticals. The catalytic oxidation of n-pentene to produce 1,2-pentanediol is a common olefin catalytic oxidation reaction. CN201410427953.6 discloses a method for preparing 1,2-pentanediol, which uses Ti-MCM-41 molecular sieve as the catalyst, 25%-50% hydrogen peroxide as the oxidizing agent, and n-pentene as the raw material for epoxidation under the conditions of an organic solvent and an auxiliary agent. This method is simple, has low production costs, and has high reaction conversion rate.

[0005] Propyl epoxyhexane is an important organic compound commonly used to produce 1,2-pentanediol. Catalytic oxidation of n-pentene can also produce propyl epoxyhexane (i.e., 1,2-epoxypentane). In the study of synthesizing 1,2-epoxypentane from n-pentene, titanium silicate molecular sieve was used as the catalyst to explore the reaction conditions for synthesizing 1,2-epoxypentane from n-pentene. The optimal conditions were obtained as follows: using TS-1 as the catalyst, methanol as the solvent, and reacting at 50°C for 2 h, with a conversion rate of 1-pentene of 90.3%, a selectivity of 1,2-epoxypentane of 89.9%, and a yield of 1,2-epoxypentane of 81.2%.

[0006] Methoxy pentanol is an important raw material for multiple purposes, which is one of alcohol ethers. Alcohol ethers have excellent surface activity, detergency, low temperature emulsification performance, low foam property, and good compatibility with enzymes or fabric softener. Methoxy pentanol is widely used in daily chemical industry. Methoxy pentanol can be applied to papermaking industry, emulsifier, or indispensable auxiliary in leather and pesticide industry. Common methoxy pentanol includes 1-methoxy-2-pentanol and 2-methoxy-1-pentanol.

[0007] In a catalytic oxidation reaction of n-pentene, four oxidation products of 1,2-pentanediol, propyl oxymethylene hexane, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol are simultaneously generated, which has not been reported. It is of great significance to develop a method for preparing the above four products by catalytic oxidation of n-pentene to meet different industrial needs or to prepare multiple catalytic oxidation products of n-pentene. SUMMARY

[0008] Therefore, the technical problem to be solved by the present application is to provide a method for catalytic oxidation of n-pentene. The method can adjust the type of cosolvent and the parameters of the reaction to control the selectivity of the products propyl oxymethylene hexane, 1,2-pentanediol, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol.

[0009] To achieve the above purpose, the technical solution adopted by the present application is as follows:

[0010] The present application provides a method for catalytic oxidation of n-pentene, comprising the following steps:

[0011] Mixing n-pentene, molecular sieve catalyst, hydrogen peroxide solution and cosolvent to obtain n-pentene catalytic oxidation products;

[0012] The cosolvent is selected from one or more of methanol, isopropanol, acetone and acetonitrile.

[0013] The n-pentene catalytic oxidation products are selected from one or more of propyl oxymethylene hexane, 1,2-pentanediol, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol.

[0014] Preferably, the n-pentene catalytic oxidation products are selected from propyl oxymethylene hexane, 1,2-pentanediol, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol;

[0015] Or the n-pentene catalytic oxidation products are selected from propyl oxymethylene hexane, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol;

[0016] Or the n-pentene catalytic oxidation products are selected from propyl oxymethylene hexane and 1,2-pentanediol.

[0017] The catalytic oxidation reaction includes the following reaction processes:

[0018] By selecting different cosolvents and reaction parameters, different catalytic oxidation products of n-pentene can be prepared. In some embodiments of the present application, when the cosolvent contains methanol or only methanol, the methanol is both a solvent and a reaction material participating in the reaction.

[0019] When the cosolvent is selected as methanol, the selectivity of the catalytic oxidation products of n-pentene, propylene oxide, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol and 1,2-pentanediol, is 1.35%, 69.03%, 28.86% and 0.76%, respectively. The total selectivity of 1-methoxy-2-pentanol and 2-methoxy-1-pentanol is relatively high, which is 97.89%.

[0020] When the cosolvent is selected as acetone or acetonitrile, the catalytic oxidation product of n-pentene is mainly propylene oxide, and the selectivity is 99.67% or 99.91%, respectively, and there is no 1-methoxy-2-pentanol and 2-methoxy-1-pentanol. This shows that when acetone or acetonitrile is selected as the cosolvent, the catalytic oxidation of n-pentene is basically converted into propylene oxide.

[0021] When the cosolvent is selected as a mixture of methanol and acetonitrile, the catalytic oxidation product of n-pentene is propylene oxide, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol, and the selectivity is 97.95%, 1.39% and 0.43%, respectively. Compared with acetonitrile or acetone as the cosolvent, the selectivity of 1-methoxy-2-pentanol and 2-methoxy-1-pentanol is slightly improved.

[0022] When the cosolvent is selected as a mixture of methanol and acetone, the catalytic oxidation product of n-pentene is propylene oxide, 1-methoxy-2-pentanol and 2-methoxy-1-pentanol, and the selectivity is 98.24%, 0.98% and 0.76%, respectively, but no 1,2-pentanediol is generated.

[0023] When one or more of the above products is needed in industrial production, the desired product can be obtained by adjusting the cosolvent and the reaction parameters.

[0024] In addition, the parameters of the reaction in the method also affect the selectivity of the catalytic oxidation product of n-pentene.

[0025] The reaction parameters include temperature, amount of raw materials (molecular sieve catalyst, hydrogen peroxide, n-pentene), stirring speed, etc.

[0026] Preferably, the molecular sieve catalyst is selected from titanium-silicon molecular sieve.

[0027] Preferably, the titanium silicalite molecular sieve has a TiO2 content of 1 wt% to 5 wt%, a SiO2 content of 90 wt% to 97 wt%, and an Al2O3 content of 0.05 wt% to 0.5 wt%.

[0028] Preferably, the titanium silicalite molecular sieve has a specific surface area of 350 m 2 / g to 500 m / g, a pore volume of 0.25 mL / g to 0.7 mL / g, and a pore size of 2 nm to 10 nm.

[0029] Preferably, the purity of the n-pentene is 97.5 wt% to 99.5 wt%.

[0030] The water content in the n-pentene is ≤0.05 wt%, the content of hydrocarbons below C5 is <0.5 wt%, the content of hydrocarbons above C5 is <0.5 wt%, and the content of other C5 olefins is ≤1.5 wt%.

[0031] Within a certain range, under the same conditions, a decrease in the content of hydrogen peroxide will reduce the conversion rate of n-pentene, the selectivity of 1-methoxy-2-pentanol and 2-methoxy-1-pentanol, and increase the selectivity of propyl oxirane.

[0032] Preferably, the content of hydrogen peroxide in the hydrogen peroxide solution is 10 wt% to 50 wt%; more preferably, 10 wt% to 40 wt%; and further preferably, 15 wt% to 35 wt%.

[0033] Within a range of 30°C to 150°C, as the temperature increases, the conversion rate of n-pentene increases, and the selectivity of 1-methoxy-2-pentanol and 2-methoxy-1-pentanol increases.

[0034] Preferably, the temperature of the reaction is 30°C to 150°C; more preferably, 40°C to 130°C; and further preferably, 50°C to 120°C.

[0035] Under the same reaction conditions, within a range of 30°C to 150°C, an increase in temperature will increase the selectivity of 1-methoxy-2-pentanol and 2-methoxy-1-pentanol.

[0036] Preferably, the reaction time is 0.5 h to 8 h; more preferably, 1 h to 6 h; and further preferably, 1 h to 5 h.

[0037] Preferably, the stirring rate of the reaction is 100 rpm to 800 rpm; more preferably, 250 rpm to 700 rpm; and further preferably, 300 rpm to 600 rpm.

[0038] Preferably, the molar ratio of n-pentene to hydrogen peroxide in the hydrogen peroxide solution is 1:(0.2-3); more preferably 1:(0.25-2); and further preferably 1:(0.33-1.5).

[0039] When the content of the molecular sieve catalyst is changed, the selectivity of the n-pentene catalytic oxidation product is also affected.

[0040] Preferably, the content of the molecular sieve catalyst in the n-pentene is 0.05wt%-15wt%; more preferably 1wt%-12wt%; and further preferably 3wt%-10wt%.

[0041] Preferably, the mass ratio of the cosolvent to n-pentene is (2-10):1; more preferably (3-8):1; and further preferably (3-6):1.

[0042] Preferably, the method is used to regulate the selectivity of the n-pentene catalytic oxidation product by adjusting the type of the cosolvent or the parameters of the reaction.

[0043] The application also provides a n-pentene catalytic oxidation product prepared by the above method.

[0044] Preferably, the n-pentene catalytic oxidation product is selected from one or more of propylene oxide, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol, and 1,2-pentanediol.

[0045] Compared with the prior art, the method for n-pentene catalytic oxidation provided by the application comprises the following steps:

[0046] The n-pentene, the molecular sieve catalyst, the hydrogen peroxide solution, and the cosolvent are mixed to obtain a n-pentene catalytic oxidation product. The cosolvent is selected from one or more of methanol, isopropyl alcohol, acetone, and acetonitrile. The n-pentene catalytic oxidation product is selected from one or more of propylene oxide, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. The selectivity of the products, i.e., propylene oxide, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol, can be controlled by adjusting the type of the cosolvent and the parameters of the reaction. One or more desired n-pentene catalytic oxidation products can be prepared in the same reaction according to different industrial requirements. DETAILED DESCRIPTION

[0047] In order to further illustrate the application, the method for n-pentene catalytic oxidation provided by the application is described in detail below with reference to the examples.

[0048] Example 1

[0049] 100 ml stainless steel reactor was added n-pentene 5.22 g, 30 wt% hydrogen peroxide solution 8.46 g, titanium silicalite 0.40 g, methanol 26.10 g, the reaction temperature was 60 ℃, the stirring speed was 500 rpm, the reaction time was 3.0 h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300 rpm, the centrifugation time was 30 min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 54.67%, the selectivity of propyl oxirane, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol was 67.00%, 22.47%, 10.29% respectively.

[0050] Example 2

[0051] 100 ml stainless steel reactor was added n-pentene 5.22 g, 30 wt% hydrogen peroxide solution 8.46 g, titanium silicalite 0.40 g, methanol 26.10 g, the reaction temperature was 90 ℃, the stirring speed was 500 rpm, the reaction time was 3.0 h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300 rpm, the centrifugation time was 30 min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 62.83%, the selectivity of propyl oxirane, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol, 1,2-pentanediol was 47.69%, 32.37%, 18.74%, 0.43% respectively.

[0052] Example 3

[0053] 100 ml stainless steel reactor was added n-pentene 5.22 g, 30 wt% hydrogen peroxide solution 8.46 g, titanium silicalite 0.40 g, methanol 26.10 g, the reaction temperature was 120 ℃, the stirring speed was 500 rpm, the reaction time was 3.0 h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300 rpm, the centrifugation time was 30 min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 84.59%, the selectivity of propyl oxirane, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol, 1,2-pentanediol was 1.35%, 69.03%, 28.86%, 0.76% respectively.

[0054] Example 4

[0055] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 8.46g, titanium silicalite 0.40g, methanol 26.10g, the reaction temperature was 50℃, the stirring speed was 500rpm, the reaction time was 1.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 40.72%, the selectivity of propylene oxide, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol was 96.89%, 1.97%, 1.08% respectively.

[0056] Example 5

[0057] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 5.64g, titanium silicalite 0.40g, methanol 26.10g, the reaction temperature was 60℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 46.29%, the selectivity of propylene oxide, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol was 88.64%, 7.76%, 3.38% respectively.

[0058] Example 6

[0059] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 5.64g, titanium silicalite 0.40g, methanol 26.10g, the reaction temperature was 60℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 46.29%, the selectivity of propylene oxide, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol was 88.64%, 7.76%, 3.38% respectively.

[0060] Example 7

[0061] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 5.64g, titanium silicalite 0.40g, acetonitrile 26.10g, the reaction temperature was 60℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 5.75%, the selectivity of propyl oxirane was 99.91%. It was equivalent to that n-pentene catalytic oxidation was basically converted to propyl oxirane.

[0062] Example 8

[0063] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 5.64g, titanium silicalite 0.40g, methanol 13.05g+acetonitrile 13.05g, the reaction temperature was 60℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 36.81%, the selectivity of propyl oxirane, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol was 97.95%, 1.39%, 0.43% respectively.

[0064] Example 9

[0065] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 5.64g, titanium silicalite 0.40g, methanol 13.05g+acetone 13.05g, the reaction temperature was 60℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 42.35%, the selectivity of propyl oxirane, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol was 98.24%, 0.98%, 0.76% respectively.

[0066] Example 10

[0067] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 8.46g, titanium silicalite 0.40g, acetone 26.1g, the reaction temperature was 120℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 64.76%, the selectivity of propyl oxirane, 1,2-pentanediol was 6.45%, 93.55% respectively.

[0068] Example 11

[0069] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 8.46g, titanium silicalite 0.40g, acetone 26.1g, the reaction temperature was 120℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 64.76%, the selectivity of propyl oxirane, 1,2-pentanediol was 6.45%, 93.55% respectively.

[0070] Example 12

[0071] 100ml stainless steel reactor was added n-pentene 5.22g, 30wt% hydrogen peroxide solution 8.46g, titanium silicalite 0.40g, acetone 26.1g, the reaction temperature was 120℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 64.76%, the selectivity of propyl oxirane, 1,2-pentanediol was 6.45%, 93.55% respectively.

[0072] Example 13

[0073] 100ml stainless steel reactor was added n-pentene 5.22g, 15wt% hydrogen peroxide solution 16.92g, titanium silicalite 0.26g, methanol 26.1g, the reaction temperature was 60℃, the stirring speed was 500rpm, the reaction time was 4.0h, after the reaction, the crude product was treated by centrifuge, the centrifuge speed was 4300rpm, the centrifuge time was 30min, the upper solution was analyzed by gas chromatograph GC-7890B, the conversion rate of n-pentene was 46.74%, the selectivity of propyl oxirane, 1-methoxy-2-pentanol, 2-methoxy-1-pentanol, 1,2-pentanediol was 32.63%, 15.43%, 5.3%, 46.64% respectively.

[0074] The above examples are only used to help understand the method of the present application and its core idea. It should be noted that for those skilled in the art, without departing from the principles of the present application, the present application can be improved and modified, and these improvements and modifications also fall within the scope of the claims of the present application.

Claims

1. A process for the catalytic oxidation of n-pentene, characterized in that, The method comprises the following steps: mixing n-pentene, a molecular sieve catalyst, a hydrogen peroxide solution, a cosolvent to obtain a n-pentene catalytic oxidation product; the cosolvent is selected from one or more of methanol, isopropanol, acetone, acetonitrile; the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

2. The method of claim 1, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

3. The method of claim 1, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

4. The method of claim 3, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

5. The method of claim 1, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

6. The method of claim 1, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

7. The method of claim 1, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

8. The method of claim 1, wherein, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

9. The method according to any one of claims 1 to 8, characterized in that, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

10. A catalytic oxidation product of n-pentene, characterized by, the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol. the n-pentene catalytic oxidation product is selected from one or more of propyl oxirane, 1,2-pentanediol, 1-methoxy-2-pentanol, and 2-methoxy-1-pentanol.

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