CN108752197A - A kind of propylene oxidative synthesis acrylic acid - Google Patents
A kind of propylene oxidative synthesis acrylic acid Download PDFInfo
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- CN108752197A CN108752197A CN201810445351.1A CN201810445351A CN108752197A CN 108752197 A CN108752197 A CN 108752197A CN 201810445351 A CN201810445351 A CN 201810445351A CN 108752197 A CN108752197 A CN 108752197A
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- acrylic acid
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- propylene
- vanadium oxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/25—Nitrates
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
- B01J37/035—Precipitation on carriers
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- 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
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention belongs to acrylic acid to synthesize field；More particularly to a kind of propylene oxidative synthesis acrylic acid, including：By propylene, oxygen, vapor and inert gas according to 1:（5-25）:（0.1-0.5）:（5-25）Volume ratio mixing, mixed gas is passed through in reaction unit, mixed gas carries out oxidation reaction at 0.5-1.3MPa, 320-400 DEG C；Oxidation catalyst is mounted in reaction unit, oxidation reaction terminates, and reaction product is condensed, and obtains acrylic acid aqueous solution, acrylic acid aqueous solution is through extraction process, isolated acrylic acid.Oxidation catalyst used in the present invention uses expanded graphite for carrier, loads specific active component, and pass through the optimization to each active component dosage so that catalyst has higher selectivity and catalytic activity, to make the concentration of acrylic acid greatly improve.
Description
Technical field
The invention belongs to acrylic acid synthesis technical fields；More particularly to a kind of propylene oxidative synthesis acrylic acid.
Background technology
Acrylic acid is important petrochemical industry, light industry and medical material, can be used for produce adsorbent, cleanser, fiber,
Pulp additive, adhesive, plastics, coating etc., and their new application is also constantly extending, and it is most heavy to become 21 century
One of chemical products wanted.
CN107162896A discloses a kind of methacrylaldehyde liquid phase catalytic oxidation and prepares acrylic acid.This method is with organic
Solvent is reaction dissolvent system, and methacrylaldehyde and nitrogen doped carbon nanotube is added, oxygen is passed through, in pressure 0.1-2MPa, temperature 80-
Under conditions of 100 DEG C, it is stirred to react 0.1-24h, is acrylic acid by acrolein oxidation.The organic solvent includes bis- chloroethenes of 1,2-
One or more of alkane, carbon tetrachloride and toluene.The mass ratio of the nitrogen doped carbon nanotube and methacrylaldehyde is 1:45-1:25.
CN105017008B discloses a kind of one step of propane oxidation continuous production acrylic acid.This method is in reaction work
Using the calandria type fixed bed reactor of annular mixed metal oxide catalyst, mixed feeding, H in sequence2O：N2：O2：Propane：
CO：CO2：Propylene molar ratio is 10.0-20.0%：40.0-60.0%：10.0-18.0%：10.0-15.0%：1.5-8.0%：
2.0-8.0%：1.0-5.0%；Reactor outlet gas enters absorption tower, desalination water washing, absorption, separation thick third through quencher
Olefin(e) acid product；The tail gas that absorption tower top row goes out simultaneously maintains the concentration of by-product to be recycled after reasonable level range through burning disposal
Oxidation reaction is participated in into reactor.Although this method shortens technological process, reduces production cost, but the product of gained：
The concentration of acrylic acid aqueous solution is relatively low, and the time of separation is caused to greatly increase.
CN10418719AB discloses a kind of synthesis of conjugated carboxylic alkeneacid, with CO2Be raw material with ethylene, acetonitrile be solvent,
Metal Ru complexs are that catalyst directly synthesizes acrylic acid, ethylene and carbon dioxide molar ratio 1:1-1:5, preferably 1:2-1:
4；40-130 DEG C of reaction temperature, preferably 50-120 DEG C；Reaction pressure 0.5-6.0MPa, preferably 1.0-5.5Mpa；Metal Ru
Complex, acetonitrile addition ratio be 1.5-3.5g：100-200mL；Suitable natrium carbonicum calcinatum is added as co-catalyst, nothing
Aqueous sodium carbonate, metal Ru complexs, acetonitrile addition ratio be 10-20g：1.5-3.5g：100-200mL.
The preparation method that the above patent of invention provides, the concentration of product propylene acid solution is relatively low, increases later separation system
The time of acrylic acid, also resulting in the yield of acrylic acid reduces.
Invention content
Insufficient present in background technology in order to overcome, the present invention provides a kind of propylene oxidative synthesis acrylic acid.
Technical solution used in the present invention is：
By propylene, oxygen, vapor and inert gas according to 1:（5-25）:（0.1-0.5）:（5-25）Volume ratio mixing, will
Mixed gas is passed through in reaction unit, then aoxidizes mixed gas at 0.5-1.3MPa, 320-400 DEG C
Reaction；Wherein, the oxidation catalyst that grain size is 300-900 μm is mounted in the reaction unit, after 2.5-4 hours, oxidation is anti-
It should terminate, reaction product is condensed, obtain acrylic acid aqueous solution, the acrylic acid aqueous solution is detached through extraction process
To acrylic acid.
The preparation method of the oxidation catalyst includes the following steps：
Vanadium oxide powder is heated to 800-900 DEG C, then the vanadium oxide melted pours into the vanadium oxide that 100 parts melt
It in 500-800 parts of deionized waters, stirs evenly, obtains vanadium oxide colloidal sol；
By weight, by 15-30 parts of ammonium molybdates, 1-5 parts of titanium acid ammoniums, 5-10 parts of ammonium antimonates, 6-12 parts by weight of potassium nitrate, 40-60
Part expanded graphite；It is added in 200-400 parts of crystalline form modification agent compositions, after agitated ageing, gained sediment is added to
In 200-400 parts of vanadium oxide colloidal sols, 10-30 parts of phosphoric acid are added, are stirred evenly；Mix products are carried out at 800-1000 DEG C
Calcining, after calcining, calcined product is crushed, obtains the oxidation catalyst.
Crystalline form modification agent composition includes：1-5 parts of butyl titanates, 0.01-0.05 parts four（2,2,6,6- tetramethyls -3,5-
Heptadione acid）Cerium, 200-400 part methanol, 0.01-0.05 parts of 2- guanidine succinic acids, 1-5 parts of fumaric acid list ethyl ester zinc salts,
The polyether-ether-ketone PEEK trees of 0.5-2 parts of tin indium oxide, LCP, 0.01-0.05 parts of 0.5-0.9 parts of polymeric liquid crystal copolymer
Fat, 0.3-0.9 parts of oxo -2 ethyl hexanoic acid root close the homopolymer of aluminium, 0.3-0.9 parts of poly- (1,1- dimethyl-silicons azane),
It is uniformly mixed；
The time of the calcining is 1.5-3 hours；
It uses butyl acetate or dimethylbenzene for extractant, makes the acrylic acid in acrylic acid aqueous solution and water separation.
The inert gas is nitrogen or argon gas.
The invention has the advantages that compared with the prior art,：Oxidation catalyst used in the present invention uses expanded graphite
For carrier, molybdenum oxide, vanadium oxide, titanium oxide, antimony oxide, potassium nitrate active component are loaded, and by using each active component
The optimization of amount so that catalyst has higher selectivity and catalytic activity, to keep the concentration of acrylic acid in reaction product big
It is big to improve；
There are the surface defects of height for amorphous oxide, can generate special catalytic effect, crystalline form modification agent composition can
To generate surface defect powdery amorphous metal oxide so that catalyst has higher selectivity and catalytic activity.
Specific implementation mode
Below by specific embodiment, the invention will be further described：
Embodiment 1
A kind of propylene oxidative synthesis acrylic acid, used technical solution are：
By propylene, oxygen, vapor and inert gas according to 1:5:0.1:5 volume ratio mixing, mixed gas is passed through
In reaction unit, mixed gas is then subjected to oxidation reaction at 0.5MPa, 400 DEG C；Wherein, in the reaction unit
It is mounted with the oxidation catalyst that grain size is 300 μm,
The preparation method of the oxidation catalyst includes the following steps：
Vanadium oxide powder is heated to 850 DEG C, then the vanadium oxide that 100 parts melt is poured into 700 parts by the vanadium oxide melted
It in deionized water, stirs evenly, obtains vanadium oxide colloidal sol；
By weight, by 19 parts of ammonium molybdates, 2 parts of titanium acid ammoniums, 7 parts of ammonium antimonates, 8 parts by weight of potassium nitrate, 49 parts of expanded graphites；It is added
Into 300 parts of crystalline form modification agent compositions, after agitated ageing, gained sediment is added in 300 parts of vanadium oxide colloidal sols, then
12 parts of phosphoric acid are added, stir evenly；Mix products are calcined at 900 DEG C, the time of calcining is 2 hours, and calcining terminates
Afterwards, calcined product is crushed, obtains the oxidation catalyst；
Crystalline form modification agent composition includes：2 parts of butyl titanates, 0.03 part four（DPM dpm,dipivalomethane acid）Cerium,
300 parts of methanol, 0.03 part of 2- guanidine succinic acid, 3 parts of fumaric acid list ethyl ester zinc salts, 0.8 part of tin indium oxide, 0.7 part of liquid
Polycrystalline macromolecule polymer LCP, 0.03 part of polyether-ether-ketone PEEK resins, 0.5 part of oxo -2 ethyl hexanoic acid root close the homopolymerization of aluminium
Object, is uniformly mixed 0.5 part of poly- (1,1- dimethyl-silicons azane)；
After 2.5 hours, oxidation reaction terminates, and reaction product is condensed, and obtains acrylic acid aqueous solution, and the acrylic acid is water-soluble
Liquid uses butyl acetate to be extracted for extractant, makes the acrylic acid in acrylic acid aqueous solution and water separation, isolated propylene
Acid.
Embodiment 2
A kind of propylene oxidative synthesis acrylic acid, used technical solution are：
By propylene, oxygen, vapor and inert gas according to 1:20:0.3:15 volume ratio mixing, mixed gas is led to
Enter in reaction unit, mixed gas is then subjected to oxidation reaction at 1.0MPa, 360 DEG C；Wherein, the reaction unit
In to be mounted with grain size be 500 μm of oxidation catalyst, the oxidation catalyst includes 20g molybdenum oxides, 10g vanadium oxides, 3g oxidations
Titanium, 8g antimony oxides, 10g potassium nitrate and 50g expanded graphites；The preparation method of the oxidation catalyst includes the following steps：
Vanadium oxide powder is heated to 800 DEG C, then the vanadium oxide that 100 parts melt is poured into 500 parts by the vanadium oxide melted
It in deionized water, stirs evenly, obtains vanadium oxide colloidal sol；
By weight, by 15 parts of ammonium molybdates, 1 part of titanium acid ammonium, 5 parts of ammonium antimonates, 6 parts by weight of potassium nitrate, 40 parts of expanded graphites；It is added
Into 200 parts of crystalline form modification agent compositions, after agitated ageing, gained sediment is added in 200 parts of vanadium oxide colloidal sols, then
10 parts of phosphoric acid are added, stir evenly；Mix products are calcined at 800 DEG C, the time of calcining is 1.5 hours, calcining knot
Shu Hou crushes calcined product, obtains the oxidation catalyst.
Crystalline form modification agent composition includes：1 part of butyl titanate, 0.01 part four（DPM dpm,dipivalomethane
Acid）Cerium, 200 parts of methanol, 0.01 part of 2- guanidine succinic acid, 1 part of fumaric acid list ethyl ester zinc salt, 0.5 part of tin indium oxide, 0.5
Polymeric liquid crystal copolymer LCP, 0.01 part of polyether-ether-ketone PEEK resins, 0.3 part of oxo -2 ethyl hexanoic acid root of part close aluminium
Homopolymer, 0.3 part of poly- (1,1- dimethyl-silicons azane), be uniformly mixed；
After 3 hours, oxidation reaction terminates, and reaction product is condensed, and obtains acrylic acid aqueous solution, the acrylic acid aqueous solution
It uses dimethylbenzene to be extracted for extractant, makes the acrylic acid in acrylic acid aqueous solution and water separation, isolated acrylic acid.
Embodiment 3
A kind of propylene oxidative synthesis acrylic acid, used technical solution are：
By propylene, oxygen, vapor and inert gas according to 1:25:0.5:25 volume ratio mixing, mixed gas is led to
Enter in reaction unit, mixed gas is then subjected to oxidation reaction at 1.3MPa, 400 DEG C；Wherein, the reaction unit
In to be mounted with grain size be 900 μm of oxidation catalyst, the oxidation catalyst includes 30g molybdenum oxides, 18g vanadium oxides, 5g oxidations
Titanium, 10g antimony oxides, 12g potassium nitrate and 60g expanded graphites；The preparation method of the oxidation catalyst includes the following steps：
Vanadium oxide powder is heated to 900 DEG C, then the vanadium oxide that 100 parts melt is poured into 800 parts by the vanadium oxide melted
It in deionized water, stirs evenly, obtains vanadium oxide colloidal sol；
By weight, by 30 parts of ammonium molybdates, 5 parts of titanium acid ammoniums, 10 parts of ammonium antimonates, 12 parts by weight of potassium nitrate, 60 parts of expanded graphites；Add
Enter into 400 parts of crystalline form modification agent compositions, after agitated ageing, gained sediment be added in 400 parts of vanadium oxide colloidal sols,
30 parts of phosphoric acid are added, are stirred evenly；Mix products are calcined at 1000 DEG C, the time of the calcining is 3 hours；It forges
After burning, calcined product is crushed, obtains the oxidation catalyst.
Crystalline form modification agent composition includes：5 parts of butyl titanates, 0.05 part four（DPM dpm,dipivalomethane
Acid）Cerium, 400 parts of methanol, 0.05 part of 2- guanidine succinic acid, 5 parts of fumaric acid list ethyl ester zinc salts, 2 parts of tin indium oxide, 0.9 part
Polymeric liquid crystal copolymer LCP, 0.05 part of polyether-ether-ketone PEEK resins, 0.9 part of oxo -2 ethyl hexanoic acid root close aluminium
Homopolymer, is uniformly mixed 0.9 part of poly- (1,1- dimethyl-silicons azane)；
After 4 hours, oxidation reaction terminates, and reaction product is condensed, and obtains acrylic acid aqueous solution, the acrylic acid aqueous solution
It uses dimethylbenzene to be extracted for extractant, makes the acrylic acid in acrylic acid aqueous solution and water separation, isolated acrylic acid.
Comparative example 1
Titanium oxide, the other the same as in Example 1 are not included in oxidation catalyst.
Comparative example 2
Antimony oxide, the other the same as in Example 1 are not included in oxidation catalyst.
Comparative example 3
Potassium nitrate, the other the same as in Example 1 are not included in oxidation catalyst.
Comparative example 4
It is not added with the homopolymer that oxo -2 ethyl hexanoic acid root closes aluminium, the other the same as in Example 1.
Comparative example 5
Crystalline form modification agent composition, the other the same as in Example 1 are not included in oxidation catalyst.
Comparative example 6
It is not added with four（DPM dpm,dipivalomethane acid）Cerium, the other the same as in Example 1.
Comparative example 7
It is not added with 2- guanidine succinic acids, the other the same as in Example 1.
Comparative example 8
It is not added with fumaric acid list ethyl ester zinc salt, the other the same as in Example 1.
Table：The concentration of acrylic acid aqueous solution obtained by different process and the comparison of acrylic acid yield.
| Number | Acrylic acid aqueous solution concentration/% | Yield/% |
| Embodiment 1 | 67 | 87.62 |
| Embodiment 2 | 71 | 89.79 |
| Embodiment 3 | 65 | 87.88 |
| Comparative example 1 | 32 | 65.33 |
| Comparative example 2 | 33 | 63.70 |
| Comparative example 3 | 28 | 55.06 |
| Comparative example 4 | 54 | 74.32 |
| Comparative example 5 | 26 | 51.21 |
| Comparative example 6 | 58 | 75.25 |
| Comparative example 7 | 61 | 78.32 |
| Comparative example 8 | 59 | 76.58 |
Claims (5)
1. a kind of propylene oxidative synthesis acrylic acid, it is characterised in that：Described method includes following steps：
By propylene, oxygen, vapor and inert gas according to 1:（5-25）:（0.1-0.5）:（5-25）Volume ratio mixing, will
Mixed gas is passed through in reaction unit, then aoxidizes mixed gas at 0.5-1.3MPa, 320-400 DEG C
Reaction；Wherein, the oxidation catalyst that grain size is 300-900 μm is mounted in the reaction unit, after 2.5-4 hours, oxidation is anti-
It should terminate, reaction product is condensed, obtain acrylic acid aqueous solution, the acrylic acid aqueous solution is detached through extraction process
To acrylic acid;
The preparation method of the oxidation catalyst includes the following steps：
Vanadium oxide powder is heated to 800-900 DEG C, then the vanadium oxide melted pours into the vanadium oxide that 100 parts melt
It in 500-800 parts of deionized waters, stirs evenly, obtains vanadium oxide colloidal sol；
By weight, by 15-30 parts of ammonium molybdates, 1-5 parts of titanium acid ammoniums, 5-10 parts of ammonium antimonates, 6-12 parts by weight of potassium nitrate, 40-60
Part expanded graphite；It is added in 200-400 parts of crystalline form modification agent compositions, after agitated ageing, gained sediment is added to
In 200-400 parts of vanadium oxide colloidal sols, 10-30 parts of phosphoric acid are added, are stirred evenly；Mix products are carried out at 800-1000 DEG C
Calcining, after calcining, calcined product is crushed, obtains the oxidation catalyst.
2. according to the method described in claim 2, it is characterized in that：The crystalline form modification agent composition includes：1-5 parts of metatitanic acid fourths
Ester, 0.01-0.05 parts four（DPM dpm,dipivalomethane acid）Cerium, 200-400 part methanol, 0.01-0.05 parts of 2- guanidines
Base succinic acid, 1-5 parts of fumaric acid list ethyl ester zinc salts, 0.5-2 parts of tin indium oxide, the polymerization of 0.5-0.9 parts of liquid crystal polymer
The polyether-ether-ketone PEEK resins of LCP, 0.01-0.05 parts of object, 0.3-0.9 parts of oxo -2 ethyl hexanoic acid root close aluminium homopolymer,
0.3-0.9 parts of poly- (1,1- dimethyl-silicons azane) is uniformly mixed.
3. according to the method described in claim 2, it is characterized in that：The time of the calcining is 1.5-3 hours.
4. according to the method described in claim 1, it is characterized in that：It uses butyl acetate or dimethylbenzene for extractant, makes propylene
Acrylic acid in aqueous acid and water separation.
5. according to the method described in claim 1, it is characterized in that：The inert gas is nitrogen or argon gas.
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| CN201810445351.1A CN108752197A (en) | 2018-05-11 | 2018-05-11 | A kind of propylene oxidative synthesis acrylic acid |
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| CN201810445351.1A CN108752197A (en) | 2018-05-11 | 2018-05-11 | A kind of propylene oxidative synthesis acrylic acid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763144A (en) * | 2019-11-22 | 2020-10-13 | 中国科学院大连化学物理研究所 | A kind of method for synthesizing acrylic acid by acetic acid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103071514A (en) * | 2013-01-29 | 2013-05-01 | 新兴能源科技有限公司 | Preparation method of catalyst for preparing acrylic acid with propylene by one-step catalytic oxidation |
| CN103285888A (en) * | 2013-04-18 | 2013-09-11 | 沈阳化工大学 | Catalyst used in preparation of acrylic acid through one-step oxidation of propylene and preparation method thereof |
-
2018
- 2018-05-11 CN CN201810445351.1A patent/CN108752197A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103071514A (en) * | 2013-01-29 | 2013-05-01 | 新兴能源科技有限公司 | Preparation method of catalyst for preparing acrylic acid with propylene by one-step catalytic oxidation |
| CN103285888A (en) * | 2013-04-18 | 2013-09-11 | 沈阳化工大学 | Catalyst used in preparation of acrylic acid through one-step oxidation of propylene and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 奚振邦等编著: "《现代化学肥料学》", 31 May 2013, 中国农业出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763144A (en) * | 2019-11-22 | 2020-10-13 | 中国科学院大连化学物理研究所 | A kind of method for synthesizing acrylic acid by acetic acid |
| CN111763144B (en) * | 2019-11-22 | 2021-10-08 | 中国科学院大连化学物理研究所 | A kind of method for synthesizing acrylic acid by acetic acid |
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Application publication date: 20181106 |