CN104230654A - Method for preparing aldehyde, ketone and acid through of catalytic oxidation alkene - Google Patents

Method for preparing aldehyde, ketone and acid through of catalytic oxidation alkene Download PDF

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CN104230654A
CN104230654A CN201310251265.4A CN201310251265A CN104230654A CN 104230654 A CN104230654 A CN 104230654A CN 201310251265 A CN201310251265 A CN 201310251265A CN 104230654 A CN104230654 A CN 104230654A
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acid
ketone
aldehyde
reaction
catalyzer
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CN104230654B (en
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李�杰
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Zibo Vocational Institute
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C45/34—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 in unsaturated 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8876—Arsenic, antimony or bismuth
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C45/34—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 in unsaturated compounds
    • C07C45/36—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 in unsaturated compounds in compounds containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen

Abstract

The invention discloses a method for preparing aldehyde, ketone and acid through oxidation of alkene. The method comprises the following steps: (1) preparing a catalyst; (2) preparing an alkene compound into aldehyde, ketone and acid in an oxygen resource environment by using the catalyst which is prepared in the step (1), and adding acetic acid or pyridine into the catalyst which is prepared in the step (1), wherein the mole percentage ratio of acetic acid or pyridine to a reaction substrate is 3-10mol%, the mole percentage ratio of the catalyst which is prepared in the step (1) to the reaction substrate is 10-30mol%, the reaction temperature is 100-200 DEG C, the reaction pressure is 5-25MPa, and the reaction time is 0.5-30 hours. The catalyst and the additive raw materials used in the method are cheap and easily available, the conversion rate and the recycling rate of aldehyde, ketone and acid are high, the environment can be protected, and a product is easy to treat.

Description

A kind of olefin catalytic oxidation for preparing is for the method for aldehyde, ketone, acid
Technical field
The present invention relates to a kind of method that olefin oxidation prepares aldehyde, ketone, acid, especially relate to a kind of method adopting many metal composite oxide catalysts directly alkene to be oxidized to efficiently ketone, aldehyde, acid.
Background technology
Alkene refers to the hydrocarbon polymer containing C=C key (carbon-to-carbon double bond) (ethylene linkage).Belong to unsaturated hydrocarbons, be divided into alkene and cycloolefin.By double bond containing how many points of another names monoolefine, diolefine etc.Have in double bond one easily broken, so can addition reaction be there is.Strand olefin hydrocarbon molecules general formula is CnH2n, and under normal temperature, C2-C4 is gas, is non-polar molecule, insoluble or be slightly soluble in water.Double bond group is the functional group in olefin hydrocarbon molecules, has reactive behavior, the addition reactions such as hydrogenation, halogenation, hydration, halogen hydrogenation, hypohalous acid, sulphating, epoxidation, polymerization can occur, the also fracture of oxidable generation double bond, generates aldehyde, carboxylic acid etc.
Carry out in the research of hydrocarbon oxidization making oxygen source of molecular oxygen, Japanese's Hirai Naruhisa etc. reports the catalyst system that a class is made up of 3-12 race metallic compound and HP, this system can be used as catalyzed oxidation naphthenic hydrocarbon, cycloolefin and the various hydrocarbon compound such as aromatic hydrocarbons containing methyl or methylene radical, generates the oxygenatedchemicalss such as alcohol, ketone, acid under mild conditions.
Selective oxidation process is reaction process important in organic chemistry.Wherein, the oxidation of alkene is used in the production of some natural products and fine chemical product usually; Such as, the oxidation products of tetrahydrobenzene and derivative thereof is that the cyclohexenone compounds of beta-unsaturated carbonyl, is often used as chemical intermediate due to its high reaction activity containing α; The oxygenatedchemicalss such as cinnamic oxidation products phenyl aldehyde and Styryl oxide are also very important chemical in fine chemistry industry.Traditionally, the oxidation of alkene is generally adopt the inorganic oxide of metering to react, but meeting environment easily pollutes, product is not easy to the problems such as separation; Therefore, the focus of Recent study concentrates on carries out the catalytic oxidation system of alkene with superoxide (superoxide such as hydrogen peroxide, tertbutyl peroxide) or oxygen as oxygen source, this type of system can improve the Atom economy of reaction, reduces the pollution of reaction; Wherein, common catalyzer is generally the complex compound of the transition metal such as iron content, copper, manganese.
Summary of the invention
Technical problem to be solved by this invention is: provide a kind of olefin oxidation to prepare the method for aldehyde, ketone, acid, especially relate to a kind of adopt many metal composite oxide catalysts directly alkene is oxidized to efficiently ketone, aldehyde, acid method for solving the problems of the technologies described above, technical scheme of the present invention is:
Olefin oxidation prepares a method for aldehyde, ketone, acid, comprises the following steps, the preparation of (1) catalyzer: consisting of of catalyzer: with SiO 2and TiO 2for carrier, the active ingredient containing by following general formula: Mo 24bi afe bni cm dn ez fo x, wherein M is at least one be selected from Mg, Co, Ca, Be, Cu, Zn, Pb, Mn; N is at least one be selected from K, Rb, Na, Li, Tl or Cs; Z is at least one in La, Ce or Sm; The span of a is 4 ~ 12; The span of b is 8 ~ 16; The span of c is 10 ~ 20; The span of d is 10 ~ 18; The span of e is 0 ~ 1; The span of f is 5 ~ 10; X is for meeting the Sauerstoffatom sum needed for other element valence; In catalyzer, the consumption of carrier is 10 ~ 40% of catalyst weight; Pore-creating compound is added in catalyst preparation process, pore-creating compound is selected from least one in ammonium nitrate, ammonium chloride, volatile salt, bicarbonate of ammonia, starch, urea, polyvinyl alcohol or acetic acid or pyridine, according to above-mentioned composition, be prepared as follows: a) appropriate ammonium molybdate is dissolved in water and obtains solution I, then by SiO 2and TiO 2add solution I, obtain solution II; B) dissolving metal salts of a certain amount of Bi, Fe, Ni, M, N, Z is formed solution III in water; C) under the condition of Keep agitation, solution III is added solution II and form catalyst pulp; D) in catalyst pulp, add a certain amount of pore-creating compound, the add-on of pore-creating compound accounts for the 3-10% of catalyst weight; E) slurry is obtained catalyst precursor by spray shaping, then obtain catalyzer through the roasting of 300-600 DEG C; (2) under oxygen source environment, olefin(e) compound is prepared into ketone, aldehyde, acid by the catalyzer prepared by step (1); In the catalyzer that step (1) prepares, add acetic acid or pyridine, the molar percentage of acetic acid or pyridine and reaction substrate is 3-10mol%; The catalyzer that in reaction, step (1) prepares and the molar percentage of reaction substrate are 10-30mol%; Temperature of reaction is 100-200 DEG C; Reaction pressure is 5-25MPa; Reaction times is 0.5-30 hour; Oxygen source is purity oxygen.
Further, described reaction pressure is 20-25MPa, and temperature of reaction is 180-200 DEG C.
Further, described alkene is alkene, cycloolefin, polycyclic olefin, aromatic olefin or their natural derivative.
Further, the molar percentage of acetic acid or pyridine and reaction substrate is 8-9mol%.
Further, wherein M is at least one be selected from Mg, Mn; N is at least one be selected from K, Na, Li; Z is at least one in La, Ce;
Further, wherein M is at least one be selected from Cu, Zn, Pb; N is at least one be selected from Rb, Tl or Cs; Z is at least one in La, Ce or Sm.
Further, described pore-creating compound is selected from least one in volatile salt, bicarbonate of ammonia, urea.
In the present invention catalyzer and additive raw material cheap and easy to get, aldehyde, ketone, sour transformation efficiency and the rate of recovery are high, environmental friendliness, and product processes well; Just olefin(e) compound and oxygen that whole process consumes, with low cost, can meet the requirement of Technological Economy, have good application prospect, be a catalysis process had wide application prospects.
Embodiment
Embodiment 1
Olefin oxidation prepares a method for aldehyde and acid, comprises the following steps, the preparation of (1) catalyzer: consisting of of catalyzer: with SiO 2and TiO 2for carrier, the active ingredient containing by following general formula:
Mo 24bi 6fe 12ni 14co 14na 1ce 8o x, x is for meeting the Sauerstoffatom sum needed for other element valence; In catalyzer, the consumption of carrier is 20% of catalyst weight; Add urea in catalyst preparation process, according to above-mentioned composition, be prepared as follows: a) appropriate ammonium molybdate is dissolved in water and obtains solution I, then by SiO 2and TiO 2add solution I, obtain solution II; B) dissolving metal salts of a certain amount of Bi, Fe, Ni, Co, Na, Ce is formed solution III in water; C) under the condition of Keep agitation, solution III is added solution II and form catalyst pulp; D) in catalyst pulp, add a certain amount of bicarbonate of ammonia, the add-on of bicarbonate of ammonia accounts for 4% of catalyst weight; E) slurry is obtained catalyst precursor by spray shaping, then obtain catalyzer through the roasting of 320 DEG C; (2) under purity oxygen environment, suberene is prepared into dialdehyde and pimelic acid in heptan by the catalyzer prepared by step (1); In the catalyzer that step (1) prepares, add pyridine, the molar percentage of pyridine and reaction substrate is 5mol%; The catalyzer that in reaction, step (1) prepares and the molar percentage of reaction substrate are 15mol%; Temperature of reaction is 150 DEG C; Reaction pressure is 10MPa; Reaction times is 2 hours; Suberene transformation efficiency is 85.2%, in reaction product heptan dialdehyde yield 60%, pimelic acid yield 15%.
Embodiment 2
Olefin oxidation prepares a method for ketone, comprises the following steps, the preparation of (1) catalyzer: consisting of of catalyzer: with SiO 2and TiO 2for carrier, the active ingredient containing by following general formula:
Mo 24bi 5fe 10ni 12mg 12rb 0.5la 6o x, x is for meeting the Sauerstoffatom sum needed for other element valence; In catalyzer, the consumption of carrier is 15% of catalyst weight; Add starch in catalyst preparation process, according to above-mentioned composition, be prepared as follows: a) appropriate ammonium molybdate is dissolved in water and obtains solution I, then by SiO 2and TiO 2add solution I, obtain solution II; B) dissolving metal salts of a certain amount of Bi, Fe, Ni, Mg, Rb, La is formed solution III in water; C) under the condition of Keep agitation, solution III is added solution II and form catalyst pulp; D) in catalyst pulp, add a certain amount of volatile salt, the add-on of volatile salt accounts for 6% of catalyst weight; E) slurry is obtained catalyst precursor by spray shaping, then obtain catalyzer through the roasting of 350 DEG C; (2) under purity oxygen environment, 2,3-phenylbenzene-2-butylene is prepared into ketone by the catalyzer prepared by step (1); In the catalyzer that step (1) prepares, add acetic acid, the molar percentage of acetic acid and reaction substrate is 3.5mol%; The catalyzer that in reaction, step (1) prepares and the molar percentage of reaction substrate are 11.5mol%; Temperature of reaction is 150 DEG C; Reaction pressure is 9MPa; Reaction times is 5 hours; 2,3-phenylbenzene-2-butylene transformation efficiency is 82%, methyl phenyl ketone yield 70% in reaction product.
Embodiment 3
Olefin oxidation prepares a method for aldehyde, comprises the following steps, the preparation of (1) catalyzer: consisting of of catalyzer: with SiO 2be carrier with TiO2, the active ingredient containing by following general formula:
Mo 24bi 7fe 14ni 18ca 16li 0.5sm 9o x, x is for meeting the Sauerstoffatom sum needed for other element valence; In catalyzer, the consumption of carrier is 25% of catalyst weight; Add polyvinyl alcohol in catalyst preparation process, according to above-mentioned composition, be prepared as follows: a) appropriate ammonium molybdate is dissolved in water and obtains solution I, then by SiO 2and TiO 2add solution I, obtain solution II; B) dissolving metal salts of a certain amount of Bi, Fe, Ni, Ca, Li, Sm is formed solution III in water; C) under the condition of Keep agitation, solution III is added solution II and form catalyst pulp; D) in catalyst pulp, add a certain amount of urea, the add-on of urea accounts for 8% of catalyst weight; E) slurry is obtained catalyst precursor by spray shaping, then obtain catalyzer through the roasting of 450 DEG C; (2) under purity oxygen environment, 3-phenylacrolein is prepared into aldehyde by the catalyzer prepared by step (1); In the catalyzer that step (1) prepares, add acetic acid, the molar percentage of acetic acid and reaction substrate is 5.5mol%; The catalyzer that in reaction, step (1) prepares and the molar percentage of reaction substrate are 12.5mol%; Temperature of reaction is 135 DEG C; Reaction pressure is 12MPa; Reaction times is 3.5 hours, and 3-phenylacrolein transformation efficiency is 89%, phenyl aldehyde yield 65% in reaction product, phenylformic acid yield 16%.

Claims (7)

1. olefin oxidation prepares a method for aldehyde, ketone, acid, it is characterized in that, comprises the following steps:
(1) preparation of catalyzer: consisting of of catalyzer: with SiO 2and TiO 2for carrier, the active ingredient containing by following general formula: Mo 24bi afe bni cm dn ez fo x, wherein M is at least one be selected from Mg, Co, Ca, Be, Cu, Zn, Pb, Mn; N is at least one be selected from K, Rb, Na, Li, Tl or Cs; Z is at least one in La, Ce or Sm; The span of a is 4 ~ 12; The span of b is 8 ~ 16; The span of c is 10 ~ 20; The span of d is 10 ~ 18; The span of e is 0 ~ 1; The span of f is 5 ~ 10; X is for meeting the Sauerstoffatom sum needed for other element valence; In catalyzer, the consumption of carrier is 10 ~ 40% of catalyst weight; Pore-creating compound is added in catalyst preparation process, pore-creating compound is selected from least one in ammonium nitrate, ammonium chloride, volatile salt, bicarbonate of ammonia, starch, urea, polyvinyl alcohol or acetic acid or pyridine, according to above-mentioned composition, be prepared as follows: a) appropriate ammonium molybdate is dissolved in water and obtains solution I, then by SiO 2and TiO 2add solution I, obtain solution II; B) dissolving metal salts of a certain amount of Bi, Fe, Ni, M, N, Z is formed solution III in water; C) under the condition of Keep agitation, solution III is added solution II and form catalyst pulp; D) in catalyst pulp, add a certain amount of pore-creating compound, the add-on of pore-creating compound accounts for the 3-10% of catalyst weight; E) slurry is obtained catalyst precursor by spray shaping, then obtain catalyzer through the roasting of 300-600 DEG C;
(2) under oxygen source environment, olefin(e) compound is prepared into ketone, aldehyde, acid by the catalyzer prepared by step (1); In the catalyzer that step (1) prepares, add acetic acid or pyridine, the molar percentage of acetic acid or pyridine and reaction substrate is 3-10mol%; The catalyzer that in reaction, step (1) prepares and the molar percentage of reaction substrate are 10-30mol%; Temperature of reaction is 100-200 DEG C; Reaction pressure is 5-25MPa; Reaction times is 0.5-30 hour; Oxygen source is purity oxygen.
2. olefin oxidation according to claim 1 prepares the method for aldehyde, ketone, acid, and it is characterized in that: described reaction pressure is 20-25MPa, temperature of reaction is 180-200 DEG C.
3. olefin oxidation according to claim 1 prepares the method for aldehyde, ketone, acid, it is characterized in that: described alkene is alkene, cycloolefin, polycyclic olefin, aromatic olefin or their natural derivative.
4. olefin oxidation according to claim 1 prepares the method for aldehyde, ketone, acid, it is characterized in that: wherein M is at least one be selected from Mg, Mn; N is at least one be selected from K, Na, Li; Z is at least one in La, Ce.
5. olefin oxidation according to claim 1 prepares the method for aldehyde, ketone, acid, it is characterized in that: wherein M is at least one be selected from Cu, Zn, Pb; N is at least one be selected from Rb, Tl or Cs; Z is at least one in La, Ce or Sm.
6. olefin oxidation according to claim 1 prepares the method for aldehyde, ketone, acid, it is characterized in that: described pore-creating compound is selected from least one in volatile salt, bicarbonate of ammonia, urea.
7. olefin oxidation according to claim 1 prepares the method for aldehyde, ketone, acid, it is characterized in that: the molar percentage of acetic acid or pyridine and reaction substrate is 8-9mol%.
CN201310251265.4A 2013-06-24 2013-06-24 A kind of olefin catalytic oxidation for preparing is for aldehyde, ketone, the method for acid Expired - Fee Related CN104230654B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107141211A (en) * 2017-07-03 2017-09-08 广西大学 A kind of preparation method of benzaldehyde
CN112920028A (en) * 2021-02-05 2021-06-08 湖北滋兰生物医药科技有限公司 Method for preparing aldehyde compound by olefin oxidation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1859972A (en) * 2003-10-14 2006-11-08 Lg化学株式会社 Catalyst for gaseous partial oxidation of propylene and its preparing method
CN101100419A (en) * 2006-07-05 2008-01-09 中国科学院大连化学物理研究所 Method for preparing ketone and aldehyde by using oxygen to directly oxidize olefin
CN102039144A (en) * 2009-10-13 2011-05-04 中国石油化工股份有限公司 Unsaturated aldehyde catalyst produced by an oxidation method and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1859972A (en) * 2003-10-14 2006-11-08 Lg化学株式会社 Catalyst for gaseous partial oxidation of propylene and its preparing method
CN101100419A (en) * 2006-07-05 2008-01-09 中国科学院大连化学物理研究所 Method for preparing ketone and aldehyde by using oxygen to directly oxidize olefin
CN102039144A (en) * 2009-10-13 2011-05-04 中国石油化工股份有限公司 Unsaturated aldehyde catalyst produced by an oxidation method and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107141211A (en) * 2017-07-03 2017-09-08 广西大学 A kind of preparation method of benzaldehyde
CN107141211B (en) * 2017-07-03 2020-11-13 广西大学 Preparation method of benzaldehyde
CN112920028A (en) * 2021-02-05 2021-06-08 湖北滋兰生物医药科技有限公司 Method for preparing aldehyde compound by olefin oxidation
CN112920028B (en) * 2021-02-05 2023-01-31 湖北滋兰生物医药科技有限公司 Method for preparing aldehyde compound by olefin oxidation

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