CN104402692B - Method for preparing acetone through biomimetic catalysis iso-butane oxidation - Google Patents
Method for preparing acetone through biomimetic catalysis iso-butane oxidation Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/31—Aluminium
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- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
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- B01J2531/82—Metals of the platinum group
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
Abstract
The invention discloses a method for preparing acetone through biomimetic catalysis iso-butane oxidation. The method comprises the steps that iso-butane is taken as raw material; metalloporphyrin is taken as a catalyst; oxygen is taken as an oxygen source; a certain amount of solvent, assistant and radical initiator are added; the reaction temperature is controlled to be 50 to 150 DEG C; catalytic reaction is performed in the condition that the reaction pressure is 0.5 to 3.5MPa, so as to obtain acetone. The method has the advantages of mild reaction conditions, good convenience in operation, good catalytic effect, high acetone selectivity and the like.
Description
Technical field
The present invention relates to a kind of preparation method of acetone, specifically, it is to be related to a kind of bionic catalysis oxidation system
The method of standby acetone.
Background technology
Acetone, also known as dimethyl ketone, are simplest aliphatic ketones in the world.Acetone is important chemical products, can
As organic synthesis material, for producing lucite, Merlon, epoxy resin etc.；It is also outstanding solvent, for applying
The industries such as material, binding agent；It is also used as cleaning agent, diluent, in grease industry, can be used as extractant, so acetone is existing
Effect in foundry industry is quite varied, receives much concern.
At present, the industrial method preparing acetone mainly has：(1) cumene method, this is that production acetone is main in the world
Method, cumene oxidation generates phenol, and accessory substance is acetone, and the method is most economical, efficiently.(2) isopropanol method, isopropanol takes off
Hydrogen simultaneously occurs β to rupture, and generates acetone, European patent EP 004330, prepares acetone, United States Patent (USP) US with isopropanol dehydrogenation in liquid phase
407512 with isopropanol gas-phase dehydrogenation, but the reaction temperature of these methods is high, and catalyst life is short, Chinese patent CN
1049494 with copper fiber as catalyst, and catalysis lower aliphatic alcohol dehydrogenase prepares ketone, and catalyst activity is high；Chinese patent CN
103772174A, describes the method that acetone is prepared in aqueous isopropanol low-temperature gaseous phase dehydrogenation, and aqueous isopropanol has age resistor
Extract in waste liquid and obtain, the method mild condition, reaction isopropanol content requirement is low, and so that waste liquid is obtained by.
(3) direct oxidation of propylene (Wacker) method, the method is divided into two steps, the first step, propylene and water in 8.0MPa, necessarily
At a temperature of generate isopropanol, then dehydrogenation of isopropanol generate acetone.
(4) fermentation method, fermentation method is to produce ketone using plant with some strain fermentations, and the method typically produces mixing
Ketone, Chinese patent CN 101311272 describes a kind of method that acetone, butanol, ethanol are prepared in cassava fermentation, described culture medium
Add ammonium acetate in tapioca starch, make fermentation more efficiently.
Content of the invention
It is an object of the invention to provide a kind of method that acetone is prepared for raw material with iso-butane.
For realizing the purpose of the present invention, be employed technical scheme comprise that：With iso-butane as raw material, with oxygen as oxygen source, plus
Enter solvent, auxiliary agent and radical initiator, with the mononuclear porphyrin of logical formula (I) or (II) structure or logical formula (III) structure
μ-oxygen-dinuclear metalloporphyrin is catalyst, controls and is 50～150 DEG C in reaction temperature, reaction pressure is the bar of 0.5～3.5MPa
Carry out catalytic reaction under part and obtain acetone, catalyst amount is 1～100ppm, auxiliary dosage is 0.5～5wt% of raw material, from
It is 0.05～1mol% of raw material by base initiator amount,
M in logical formula (I)1It is metallic atom Mg, Al, Fe, Co, Mn, Ni, Cu or Zn, X is halogen or hydrogen, R1、R2、R3、R4
And R5It is selected from hydrogen, halogen, nitro, methyl, hydroxyl, alkoxyl or sulfonic group；M in logical formula (II)2Be metallic atom Cr, Mn,
Fe, Co, Ni, Cu, Zn or Sn, X is halogen or hydrogen, R1、R2、R3、R4And R5It is selected from hydrogen, halogen, nitro, alkyl, alkoxyl, hydroxyl
Base, carboxyl or sulfonic group, dentate X1It is chlorine or imidazoles or pyridine；M in logical formula (III)3It is metallic atom Fe, Co, Mn, Ru
Or Rh, R1、R2、R3、R4And R5It is selected from hydrogen, halogen, nitro, alkyl, alkoxyl, hydroxyl, carboxyl or sulfonic group.
In the method that above-mentioned bionic catalysis oxidation prepares acetone, described radical initiator is selected from N- hydroxyl
One of phthalimide or derivatives thereof.
In the method that above-mentioned bionic catalysis oxidation prepares acetone, described auxiliary agent is selected from multi-wall carbon nano-tube
One of material with carbon elements such as pipe, SWCN, carboxylic carbon nano-tube, hydroxyl carbon nano tube, activated carbon, Graphene,
Preferably auxiliary agent is selected from one of material with carbon elements such as carboxylic carbon nano-tube, hydroxyl carbon nano tube, Graphene.
In the method that above-mentioned bionic catalysis oxidation prepares acetone, described solvent selected from methanol, acetonitrile, acetic acid
One of ethyl ester, toluene, dichloromethane or 1,2- dichloroethanes.
In the method that above-mentioned bionic catalysis oxidation prepares acetone, the consumption of described catalyst is 10～
50ppm, radical initiator consumption is 0.1～0.8mol% of raw material, and auxiliary dosage is 0.8～3.5wt% of raw material, reaction
Temperature is 60～110 DEG C, and reaction pressure is 0.8～2.5MPa.
The present invention by catalyst uniform dissolution in a solvent, adds radical initiator and auxiliary agent, makes iso-butane and oxygen
Carry out catalytic reaction and generate acetone in the presence of catalyst.The purpose of the radical initiator adding is to make system be easier
Generate free radical, the tertiary hydrogen capturing iso-butane generates tert-butyl group free radical, and under low temperature, metalloporphyrin has to molecular oxygen and lives well
Change acts on thus accelerating the conversion of iso-butane under low temperature.The purpose adding auxiliary agent is to improve the stability of free radical, promotes to produce
The generation of thing acetone, thus improve the conversion ratio of iso-butane and the selectivity of product.Acetone under the various reaction system of the present invention
Selectivity high, product is easily separated, and catalyst usage amount is few, and radical initiator and auxiliary agent pass through centrifugation or filter and can achieve
Reuse.
Compared with prior art, the present invention has the advantages that：
1st, the efficiency high of the present invention, selectivity of product are high, mild condition, and energy consumption reduces.
2nd, the present invention adopts metalloporphyrin is catalyst, it is to avoid the reaction temperature in current method is high, catalyst life
The problems such as short, poor activity.
3rd, the catalyst amount that the present invention uses is few, process is simple, financial cost are low, green safety, have good work
Industry application prospect.
Specific embodiment
With reference to embodiment, the present invention is described further, but protection scope of the present invention is not limited to implement
The scope that example represents.
Embodiment all belongs to ommercially available AR with reagent in comparative example.
Embodiment 1
In autoclave, add 20mL to contain 1ppm and there is logical formula (I) structural metal porphyrin (M1=Fe, X=H, R1
=NO2,R2=R3=R4=R5=H) methanol solution, add 0.025mmol the many walls of radical initiator NHPI and 0.0145g
CNT, is filled with 50mmol iso-butane and 3.5MPa O2, stir under conditions of temperature is 50 DEG C, through gas chromatographic detection,
Iso-butane conversion ratio is 24%, and the selectivity of acetone is 76%.
Embodiment 2
In autoclave, add 20mL to contain 10ppm and there is logical formula (I) structural metal porphyrin (M1=Al, X=F, R3
=OCH3,R1=R2=R4=R5=H) acetonitrile solution, add the radical initiator NHPI of 0.05mmol and 0.0232g single wall
CNT, is filled with 50mmol iso-butane and 0.8MPa O2, stir under conditions of temperature is 60 DEG C, through gas chromatographic detection,
Iso-butane conversion ratio is 29%, and the selectivity of acetone is 80%.
Embodiment 3
In autoclave, add 20mL to contain 20ppm and there is logical formula (I) structural metal porphyrin (M1=Mn, X=H, R2
=Cl, R1=R3=R4=R5=H) ethyl acetate solution, add 0.1mmol radical initiator (N- acetyl group neighbour benzene two
Carboximide, NAPI) and 0.029g carboxylic carbon nano-tube, it is filled with 50mmol iso-butane and 1.0MPa O2, it is 70 DEG C in temperature
Under conditions of stir, through gas chromatographic detection, iso-butane conversion ratio is 30%, and the selectivity of acetone is 81%.
Embodiment 4
In autoclave, add 20mL to contain 40ppm and there is logical formula (I) structural metal porphyrin (M1=Cu, X=H, R1
=R2=Cl, R3=R4=R5=H) toluene solution, add 0.5mmol radical initiator (N- acetyl group phthalyl
Imines, NAPI) and 0.0435g hydroxyl carbon nano tube, it is filled with 50mmol iso-butane and 1.5MPa O2, it is 80 DEG C in temperature
Under the conditions of stir, through gas chromatographic detection, iso-butane conversion ratio is 35%, and the selectivity of acetone is 85%.
Embodiment 5
In autoclave, add 20mL to contain 50ppm and there is logical formula (II) structural metal porphyrin (M2=Cr, X=H,
X1=Cl, R1=NO2,R2=R3=R4=R5=H) dichloromethane solution, add 0.15mmol radical initiator (N- second
Acyl group phthalimide, NAPI) and 0.058g activated carbon, it is filled with 50mmol iso-butane and 2.0MPa O2, it is 90 in temperature
Stir under conditions of DEG C, through gas chromatographic detection, iso-butane conversion ratio is 25%, the selectivity of acetone is 75%.
Embodiment 6
In autoclave, add 20mL to contain 30ppm and there is logical formula (II) structural metal porphyrin (M2=Mn, X=H,
X1=imidazoles, R1=Cl, R2=R3=R4=R5=H) 1,2- dichloroethane solution, add 0.2mmol radical initiator
NHPI and 0.0725g Graphene, is filled with 50mmol iso-butane and 0.5MPa O2, stir under conditions of temperature is 150 DEG C, warp
Gas chromatographic detection, iso-butane conversion ratio is 35%, and the selectivity of acetone is 85%.
Embodiment 7
In autoclave, add 20mL to contain 10ppm and there is logical formula (II) structural metal porphyrin (M2=Co, X=H,
X1=pyridine, R3=OCH3,R1=R2=R4=R5=H) methanol solution, add 0.25mmol radical initiator (3- pyrrole
Pyridine methyl-N-hydroxy phthalimide, Py-NHPI) and 0.087g carboxylic carbon nano-tube, be filled with 50mmol iso-butane and
2.5MPa O2, stir under conditions of temperature is 100 DEG C, through gas chromatographic detection, iso-butane conversion ratio is 45%, acetone
It is selectively 89%.
Embodiment 8
In autoclave, add 20mL to contain 20ppm and there is logical formula (II) structural metal porphyrin (M2=Fe, X=H,
X1=pyridine, R1=R2=R3=R4=R5=H) acetonitrile solution, (N- acetyl group is adjacent to add the radical initiator of 0.3mmol
BIDA, NAPI) and 0.145g hydroxyl carbon nano tube, it is filled with 50mmol iso-butane and 3.0MPa O2, in temperature it is
Stir under conditions of 110 DEG C, through gas chromatographic detection, iso-butane conversion ratio is 42%, the selectivity of acetone is 87%.
Embodiment 9
In autoclave, add 20mL to contain 20ppm and there is logical formula (III) structural metal porphyrin (M3=Fe, R1=
R2=R3=R4=R5=H) ethyl acetate solution, add the radical initiator NHPI of 0.35mmol and 0.102g Graphene,
It is filled with 50mmol iso-butane and 2.0MPa O2, stir under conditions of temperature is 90 DEG C, through gas chromatographic detection, iso-butane turns
Rate is 48%, and the selectivity of acetone is 92%.
Embodiment 10
In autoclave, add 20mL to contain 100ppm and there is logical formula (III) structural metal porphyrin (M3=Mn, R1=
Cl,R2=R3=R4=R5=H) toluene solution, (3- picolyl-N- hydroxyl is adjacent to add the radical initiator of 0.4mmol
BIDA, Py-NHPI) and 0.058g carboxylic carbon nano-tube, it is filled with 50mmol iso-butane and 1.5MPa O2, in temperature
Spend for stirring under conditions of 80 DEG C, through gas chromatographic detection, iso-butane conversion ratio is 43%, the selectivity of acetone is 86%.
Embodiment 11
In autoclave, add 20mL to contain 40ppm and there is logical formula (III) structural metal porphyrin (M3=Ru, R1=
R2=R3=R4=R5=H) dichloromethane solution, add 0.25mmol radical initiator (N- acetyl group phthalyl
Imines, NAPI) and 0.087g hydroxyl carbon nano tube, it is filled with 50mmol iso-butane and 2.0MPa O2, it is 100 DEG C in temperature
Under the conditions of stir, through gas chromatographic detection, iso-butane conversion ratio is 51%, and the selectivity of acetone is 92%.
Embodiment 12
In autoclave, add 20mL to contain 50ppm and there is logical formula (III) structural metal porphyrin (M3=Mn, R1=
NO2,R2=R3=R4=R5=H) 1,2- dichloroethane solution, add 0.3mmol radical initiator NHPI and 0.0435g
Graphene, is filled with 50mmol iso-butane and 1.8MPa O2, stir under conditions of temperature is 80 DEG C, through gas chromatographic detection, different
Butanes conversion is 53%, and the selectivity of acetone is 94%.
Claims (9)
1. a kind of bionic catalysis oxidation prepares the method for acetone it is characterised in that with iso-butane as raw material, with oxygen being
Oxygen source, adds solvent, auxiliary agent and radical initiator, with the mononuclear porphyrin of logical formula (I) or (II) structure or logical formula (III)
μ-oxygen-the dinuclear metalloporphyrin of structure be catalyst, control reaction temperature be 50～150 DEG C, reaction pressure be 0.5～
Carry out catalytic reaction under conditions of 3.5MPa and obtain acetone, catalyst amount is 1～100ppm, auxiliary dosage is the 0.5 of raw material
～5wt%, radical initiator consumption is 0.05～1mol% of raw material,
M in logical formula (I)1It is metallic atom Mg, Al, Fe, Co, Mn, Ni, Cu or Zn, R1、R2、R3、R4And R5It is selected from hydrogen, halogen
Element, nitro or methyl；M in logical formula (II)2It is metallic atom Cr, Mn, Fe, Co, Ni, Cu, Zn or Sn, R1、R2、R3、R4And R5
It is selected from hydrogen, halogen, nitro, alkyl or alkoxyl, dentate X1It is chlorine or imidazoles or pyridine；M in logical formula (III)3It is metal
Atom Fe, Co, Mn, Ru or Rh, R1、R2、R3、R4And R5It is selected from hydrogen, halogen, nitro, alkyl or alkoxyl；
Described auxiliary agent be selected from multi-walled carbon nano-tubes, SWCN, carboxylic carbon nano-tube, hydroxyl carbon nano tube,
One of activated carbon, Graphene.
2. method according to claim 1 is it is characterised in that described radical initiator is selected from N- hydroxyl neighbour's benzene two
One of carboximide or derivatives thereof.
3. method according to claim 1 it is characterised in that described auxiliary agent be carboxylic carbon nano-tube, hydroxylating carbon receives
One of mitron, Graphene.
4. method according to claim 1 is it is characterised in that described solvent selected from methanol, acetonitrile, ethyl acetate, first
One of benzene, dichloromethane or 1,2- dichloroethanes.
5. method according to claim 1 is it is characterised in that the consumption of catalyst is 10～50ppm.
6. method according to claim 1 it is characterised in that radical initiator consumption be raw material 0.1～
0.8mol%.
7. method according to claim 1 is it is characterised in that described auxiliary dosage is 0.8～3.5wt% of raw material.
8. method according to claim 1 is it is characterised in that reaction temperature is 60～110 DEG C.
9. method according to claim 1 is it is characterised in that reaction pressure is 0.8～2.5MPa.
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