CN1640861A - Alkane, alkene and substituted arene catalytic oxidation disproportionation for preparing acid and its derivatives - Google Patents
Alkane, alkene and substituted arene catalytic oxidation disproportionation for preparing acid and its derivatives Download PDFInfo
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- CN1640861A CN1640861A CNA2004100228495A CN200410022849A CN1640861A CN 1640861 A CN1640861 A CN 1640861A CN A2004100228495 A CNA2004100228495 A CN A2004100228495A CN 200410022849 A CN200410022849 A CN 200410022849A CN 1640861 A CN1640861 A CN 1640861A
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- maleic anhydride
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The present invention discloses one kind of reaction and catalyst for the reaction, and is catalytic oxidation and disproportionation of alkane, alkene and substituted arene to prepare organic acid, acid anhydride, ketone and other organic oxygenic compounds. The present invention features that alkane, alkene or substituted arene is catalytically oxidized and disproportionated to prepare acid and derivative compounds. For example, propane is oxidized to prepare acetic acid, acrylic acid and maleic anhydride; and butane is prepared into acetic acid, methyl acrylic acid, 2, 3-dimethyl maleic anhydride, 2-methyl maleic anhydride, metaphthalic acid, phthalic anhydride, paraphthalic acid, etc. In the reaction, the adopted catalyst is metal oxide and its salts.
Description
Technical field:
The invention belongs to the catalyzed oxidation disproportionation preparation method of organic oxygen-containing compounds such as a kind of organic acid, acid anhydrides, ketone
Technical background:
The aromatic hydrocarbons of alkane, alkene and replacement is from the course of processing of petroleum and natural gas, and resource is comparatively abundant, prepares organic oxygen-containing compounds such as organic acid, acid anhydrides, ketone from the aromatic hydrocarbons of alkane, alkene and replacement through catalyzed oxidation and has the potential economic benefit.Research in this respect in recent years is very active, and some research changes industrial application over to from the laboratory.
Tu, Xin Lin etc. discloses catalyzer (Tu, the Xin Lin of a kind of Mo of containing, V, Sb, Nb, K oxide compound in patent; Takahashi, Mamoru; Azuma, Hiros, JP 2001070788A2 (2001)), can under the effect of oxygen, become vinylformic acid to oxidation of propane, its yield reaches 34%, and the vinylformic acid selectivity is 62%.Takahashi, Mamoru etc. disclose a kind of catalyzer (Takahashi, Mamoru of the MoV0.3Sb0.25Nb0.12Ox of containing oxide compound in patent; Tu, Hsin Lin; Adzuma, Hiroshi, JP 2000256257A2 (2000)), can under the effect of oxygen, become vinylformic acid to oxidation of propane, conversion of propane reaches 53%, and its yield reaches 63%.Jachow, Harald etc. disclose a kind of containing of (Co and/or Ni) 0.9-1.0Mo0.7-0.99 (W in patent, Sn and/or Sb) catalyzer (Jachow of 0.01-0.3Ox oxide compound, Harald, WO9942404 A1 (1999)), can become vinylformic acid and propenal to oxidation of propane under the effect of oxygen, conversion of propane reaches 12%, vinylformic acid and propenal selectivity 69%.Ushikubo, Takashi etc. disclose a kind of catalyzer (Ushikubo, Takashi of Mo1V0.3Te0.23Nb0.12On oxide compound in patent; Kinoshita, Hisao; Watanabe, Akira, JP 10057813 A2 (1998)), can under the effect of oxygen, become vinylformic acid and propenal to oxidation of propane, vinylformic acid yield 52%.Similarly patent is also a lot.
Many research patent disclosures have been arranged in recent years oxidation of isobutane has been become the report of methacrylic acid.Yamamatsu, Setsuo etc. disclose catalyzer (Yamamatsu, the Setsuo of a kind of P of containing, Mo, V oxide compound in patent; Yamaguchi, Tatsuo JP02042032 A2 (1990)), can under the effect of oxygen, become methacrylic acid and Methylacrylaldehyde to oxidation of isobutane, Trimethylmethane transformation efficiency 6.0%, methacrylic acid selectivity 46.3%, Methylacrylaldehyde selectivity 22.3%; At Yamamatsu, Trimethylmethane transformation efficiency 7.8% on the disclosed PMoFeO catalyzer such as Setsuo, methacrylic acid selectivity 41.8%, Methylacrylaldehyde selectivity 15.3% (Yamamatsu, Setsuo; Yamaguchi, Tatsuo, JP 02042034 A2 (1990)); At Yamamatsu, Trimethylmethane transformation efficiency 8.2% on the disclosed PMoCuO catalyzer such as Setsuo, methacrylic acid selectivity 40.7%, Methylacrylaldehyde selectivity 18.2% (Yamamatsu, Setsuo; Yamaguchi, Tatsuo, JP 02042033 A2 (1990)).At Nagata, Yuichiro; Okita, Trimethylmethane transformation efficiency 12.2% on the disclosed Mo12P1V0.5Cu0.3Cs1.3O catalyzer such as Motomu, methacrylic acid selectivity 41.5%, Methylacrylaldehyde selectivity 10.8% (Nagata, Yuichiro; Okita, Motomu, JP 2001029790 A2 (2001)).Similarly patent is many in addition, as Kuroda, and Toru; Okita, Motomu, JP 04128247A2 (1992); Matsura, Ikuya; Aoki, Yukio, JP 05331085 A2 (1993), and Okusako, Akinori; Ui, Toshiaki; Nagai, Koichi, JP 09012490 A2 (1997).
Butane also can be oxidized to maleic anhydride.At Mitsubishi Chemical Industries Co., Ltd is (JP 59162951 A2) in 1984 disclosed patents, have realized 86.1% n-butane conversion and 45.4% maleic anhydride yield on the VPSiO catalyzer.Edwards, Robert Charles etc. have obtained 80% n-butane conversion and 64% maleic anhydride selectivity (Edwards, Robert Charles on the V-P-Mo-O catalyzer; Kilner, Peter Hampton; Udovich, CarlAnthony; Stauffenberg, Dennis Lee, EP 123467A1 (1984).At Wrobleski, n-butane conversion 80.4% on the disclosed PVO catalyzer such as James T, the maleic anhydride selectivity is 70.3% (Wrobleski, James T.US4515973 A (1985)).
Ishii, Hiromichi etc. have reported catalyzer (Ishii, the Hiromichi of a kind of Sb of containing, Mo, Fe, K and Ni oxide compound in patent; Matsuzawa, Hideo; Kobayashi, Masao; Yamada, Kantaro.DE 2427670 (1975)), can under the effect of oxygen, become vinylformic acid to propylene oxidation, its yield reaches 89%, and it is also effective to isobutylene oxidation system methacrylic acid that the contriver declares this catalyzer.Shiotani, Tooru (1994, Mitsubishi Rayon Co., Japan, JP 06170238A2 (1994)) in patent, discloses a kind of catalyzer Mo12W0.1BiFe1.1Zn0.2Co4.5Ni0.3K0.05P0.08Sb0.5Ox and become at propylene oxidation that propylene conversion reaches 99.5% in acrylic acid reaction, the selectivity that generates propenal is more than 90% and acrylic acid selectivity is more than 6%, and it is also effective to isobutylene oxidation system methacrylic acid that the contriver declares this catalyzer.Similarly catalyzer also has Shiotani, Tooru (Mitsubishi Rayon Co., Japan) disclosed Mo12W0.1BiFeCo4Ni0.6Zn0.1K0.06P0.08Sb0.2Ox catalyzer (Shiotani, Tooru in patent; Kuroda, Tooru, JP 06170239 A2 (1994), Shiotani, Tooru; Kuroda, Tooru JP 07016464 A2 (1995)).
In patent report, n-butene is used to the oxidation production of maleic anhydride.Umemura, Sumio etc. are at patent (Umemura, Sumio; Sakai, Fumihiko, JP 49013113 (1974)) in disclose a kind of SnMoO catalyzer 1,3-butadiene be oxidized to maleic anhydride, the 1,3-butadiene transformation efficiency is 100%, the maleic anhydride yield is 56%.Blechschmitt, Kurt etc. are at patent (Blechschmitt, Kurt; Hornberger, Paul; Reuter, Peter DE 2352314 (1975)) in a kind of V2O5 3.7% is disclosed, P2O5 13.3% and TiO2 83.0% catalyzer are oxidized to maleic anhydride to 1,3-butadiene.
Moriya, Koii etc. are at patent (Moriya, Koji; Furuoya, Itsuo, DE 2515207 (1975)) in a kind of P of containing is disclosed, V and wherein a kind of Sr, Ba, Ca, Mg, Be, Fe or Tl oxide compound are in TiO
2Or Al
2O
3Supported catalyst is oxidized to maleic anhydride to 1,3-butadiene, and the 1,3-butadiene transformation efficiency is 99%, and the maleic anhydride yield is 56%.Similar disclosed patent also has, Otaki, Tadaaki; Wada, Naoto; Hatano, Masakatu, DE 2516966 (1975), Maruyama, Hitoshi; Ueeda, Ryuhei, JP 51070196 (1976), Otaki, Tadaaki; Hatano, Masakatsu; Murayama, Masayoshi, JP 52031019 (1977).
The technology of above patent disclosure all is that the pure oxidizing reaction of experience prepares organic oxacid and acid anhydrides.In reaction process, if the preparation carbon number is when being less than the organic oxygen-containing thing of reactant molecule, deep oxidation becomes CO and CO usually
2In the oxidation of propane or propylene, generally generate vinylformic acid, propenal, acetic acid, CO and CO
2, and in case generate acetic acid and will generate CO and CO
2Equally in the oxidizing reaction of the alkane of various carbon four, carbon five and carbon six and alkene, generally all pass through pure oxidizing reaction and generate various oxygenatedchemicalss, their carbon number generally all is equal to or less than the carbon number of reactant molecule.When generating the branch period of the day from 11 p.m. to 1 a.m that carbon number is less than the reactant molecule carbon number, CO and CO
2Become inevitable outcome.
Summary of the invention:
Up to now the oxidation disproportionation reaction that does not have patent disclosure alkane and alkene, from a kind of alkane of molecular weight or alkene same catalyzer experience oxidation disproportionation reaction synthetic than original reactant molecule carbon number lack and carbon number more than the organic oxygen-containing thing, oxidation disproportionation as propane or propylene can generate acetate and maleic anhydride, and needn't generate stoichiometric CO and CO
2For straight-chain paraffin or alkene and non-side chain naphthenic hydrocarbon or the cycloolefin of carbon more than three, through all generating acetic acid after this patent disclosed oxidation disproportionation reaction and maleic anhydride is a principal product; And for carbon branched alkane, alkene, naphthenic hydrocarbon or cycloolefin more than three, the maleic anhydride (as the 2-methyl maleic anhydride or/and 2,3-dimethyl maleic anhydride) that then generates acetate and replacement is a principal product.This patent is disclosed to be a kind of new reaction type, and its reaction can be expressed as follows usually.But this patent is not restricted to following reaction, and the characteristic of this patent is the invention of oxidation disproportionation reaction itself and its application.
1, the oxidation disproportionation reaction of propane and propylene
2, the oxidation disproportionation reaction of normal butane or n-butene
3, the oxidation disproportionation reaction of Trimethylmethane or iso-butylene
4, the oxidation disproportionation reaction of Skellysolve A or positive amylene
5, the oxidation disproportionation reaction of iso-pentane or isopentene
6, the oxidation disproportionation reaction of normal hexane, n-hexylene, hexanaphthene, tetrahydrobenzene (alkene, diene, triolefin)
7, the principal product of these reactions of oxidation disproportionation reaction of side chain hexane, side chain hexene, side chain hexanaphthene, side chain tetrahydrobenzene or side chain cyclohexadiene is:
8, the oxidation disproportionation reaction principal product of other alkane, alkene is generally
This shows that oxidation disproportionation reaction disclosed by the invention is one can be used to carbon three and carbon the alkane more than three, the general reaction that conversion of olefines is above compound.Under need not isolating situation, be all to be converted into the compounds such as maleic anhydride of acetate, maleic anhydride and replacement after the mixture experience oxidation disproportionation reaction of what alkane and alkene, they are also not so difficult and separate, and industrial significant application value are arranged.
The catalyzer that is used for above oxidation disproportionation reaction is to contain V, Nb, Mo, W, Ta, many metallic compounds of one or more among the Re are main other metallic compound promotor composition that adds, other metallic promoter agent is Si, B, Al, Ge, Ti, Zr, Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Ga, In, Tl, Sn, Pb, Tm, Sb, Bi, Dy, Hf, Cr, Yb, Mn, Ho, Sc, Y, La, Sm, Ce, Tb, Co, Ni, Cu, Zn, Cd, Pr, Nd, Eu, the oxide compound of Gd, oxyhydroxide, and/or their salt, and their mixture.Catalyzer can be with various metallic compound precursor preparation.Catalyzed reaction can carried out between 150 to 600 ℃ He under the 0.01-20Mpa.
Embodiment:
1, Preparation of Catalyst
The catalyzer C1 that uses in example 1 reaction
(NH
4)
6Mo
7O
244H
2O (4.2892g) is dissolved in the 50ml deionized water, gets solution A.NH
4VO
3(0.7168g) be dissolved in the 20ml hot deionized water, get solution B.Solution A is added solution B, get a mixture.The mixture that obtains is 120 ℃ of dryings 4 hours, then 400 ℃ fired 10 hours catalyzer C1.
The catalyzer C2 that uses in example 2 reactions
(NH
4)
6Mo
7O
244H
2O (4.2892g) and H
2C
2O
42H
2O (9.1900g) is dissolved in the 50ml deionized water, gets solution A.NH
4VO
3(0.7168g) be dissolved in the 20ml hot deionized water, get solution B.Solution A is added solution B, get a mixture.The mixture that obtains is 120 ℃ of dryings 4 hours, then 400 ℃ fired 10 hours catalyzer C2.
2, catalyzed reaction
It is that 8mm, length are carried out in the fixed-bed reactor of 300mm that example 1 is reflected at an internal diameter, and catalyst levels is 1.00g, and reaction gas consists of C
3H
8(propane, down together) 10.0ml/ minute, O
25.7ml/ minute.
Conversion of propane is 22.7% on 320 ℃, C1 catalyzer, generates CO, CO
2, acetate, vinylformic acid, maleic anhydride and propylene selectivity be respectively 12.0%, 0%, 30.3%, 6.0%, 36.0% and 15.6%.Conversion of propane is 16.7% on 300 ℃, C1 catalyzer, generates CO, CO
2, acetate, vinylformic acid, maleic anhydride and propylene selectivity be respectively 4.0%, 0%, 38.2%, 8.3%, 28.1% and 21.4%.
It is that 8mm, length are carried out in the fixed-bed reactor of 300mm that example 2 is reflected at an internal diameter, and catalyst levels is 1.00g, and reaction gas consists of gas mixture C
3H
84.5ml/ minute, O
213.8ml/ minute.Conversion of propane is 53.4% on 360 ℃, C2 catalyzer, generates CO, CO
2, acetate, vinylformic acid, maleic anhydride and propylene selectivity be respectively 5.2%, 3.1%, 79.4%, 8.5%, 3.7% and 0%.
It is that 8mm, length are carried out in the fixed-bed reactor of 300mm that example 3 is reflected at an internal diameter, and catalyst levels is 1.00g, and reaction gas consists of gas mixture C
3H
69.5ml/ minute, O
26.1ml/ minute.340 ℃ on the C2 catalyzer propylene conversion be 17.5%, generate CO, CO
2, acetate, vinylformic acid, maleic anhydride selectivity be respectively 3.2%, 12.1%, 66.5%, 6.7% and 11.3%.
Claims (17)
1, the catalyzed oxidation disproportionation reaction of alkane, alkene and substituted arene prepares the method for acid, ketone and derivative compound thereof and is:
1) containing alkane, alkene and the substituted arene of three or three above carbon and oxygen (or in the air oxygen) in the molecule carries out oxidizing reaction and disproportionation reaction simultaneously and generates acetate, vinylformic acid, ketone, maleic anhydride and/or 2-methyl maleic anhydride and/or 2,3-dimethyl maleic anhydride on catalyzer;
2) have alkene during for alkane as reactant and generate, the alkene that is generated is recycled in flow process of the present invention and reacts in the reactor, up to generating final product-acid and derivative compound thereof.
The preparation method of 2, acid according to claim 1, ketone and derivative compound acid anhydrides thereof is characterized in that 1) in said oxidation disproportionation reaction.Be meant that in the oxidation disproportionation reaction the oxidized disproportionation of a kind of molecule is that carbon number is Duoed and the few product of carbon number than carbon number in the former hydrocarbon reactant in the molecule, is acetate and maleic anhydride as the oxidation of propane disproportionation, the vinylformic acid amount is few, is by product.
The preparation method of 3, acid according to claim 1, ketone and derivative compound acid anhydrides thereof, it is characterized in that said oxidation disproportionation reaction, not only original hydrocarbon reactant is suitable for, and the product of original oxidation disproportionation reaction can further oxidized disproportionation be new product, also can carry out oxidizing reaction separately with stylish product and generate small molecules acid and acid anhydrides.
The preparation method of 4, acid according to claim 1, ketone and derivative compound acid anhydrides thereof, it is characterized in that said oxidation disproportionation reaction can between the hydrocarbon molecules of the same race, between the hydrocarbon molecules not of the same race and the hydrocarbon reactant intramolecule carry out, be acetate and maleic anhydride as normal hexane, n-hexylene molecular oxidation disproportionation.
The preparation method of 5, acid according to claim 1, ketone and derivative compound acid anhydrides thereof is characterized in that 1) in said alkane be the alkane that contains three or three above carbon in the molecule, as C
3H
8To C
3+nH
2 (3+n)+2(n=0,1,2 ... m) with naphthenic hydrocarbon C
3+nH
2 (3+n)(n=0,1,2 ... m).
The preparation method of 6, acid according to claim 1, ketone and derivative compound acid anhydrides thereof is characterized in that 1) in said alkene be C
3H
6To C
3+nH
2 (3+n)(n=0,1,2 ..m), or C
3+nH
2 (1+n)(n=0,1,2 ... m), or C
3+nH
2 (n-1)(n=0,1,2 ... m).
The preparation method of 7, acid according to claim 1, ketone and derivative compound acid anhydrides thereof is characterized in that 1) in said substituted arene be toluene, dimethylbenzene, trimethylbenzene, ethylbenzene, vinylbenzene, propyl benzene and isopropyl benzene.
The preparation method of 8, acid according to claim 1, ketone and derivative compound acid anhydrides thereof, it is characterized in that said straight-chain paraffin and normal olefine experience generates acetate after the oxidation disproportionation reaction of the present invention and maleic anhydride is a principal product, and a spot of acetone, vinylformic acid, phenylformic acid, phthalic anhydride and other product, as CO, CO
2
The preparation method of 9, acid according to claim 1, ketone and derivative compound acid anhydrides thereof, it is characterized in that generating acetate, 2 after said Trimethylmethane and iso-butylene experience oxidation disproportionation reaction of the present invention, the 3-dimethyl maleic anhydride is a principal product, and a spot of acetone, methacrylic acid, terephthalic acid, m-phthalic acid, phenylformic acid, phthalic anhydride and other product, as CO, CO
2
The preparation method of 10, acid according to claim 1, ketone and derivative compound acid anhydrides thereof, it is characterized in that generating acetate, 2 after said carbon five above branched paraffins and carbon five above branched-chain alkenes experience oxidation disproportionation reaction of the present invention, 3-dimethyl maleic anhydride, 2-methyl maleic anhydride are principal product, and a spot of methacrylic acid, acetone and other product, as CO, CO
2
The preparation method of 11, acid according to claim 1, ketone and derivative compound acid anhydrides thereof, it is characterized in that generating phenylformic acid, terephthalic acid, m-phthalic acid, phthalic anhydride, acetate, 2 after said substituted arene toluene, dimethylbenzene, trimethylbenzene, ethylbenzene, vinylbenzene, propyl benzene and isopropyl benzene experience oxidation disproportionation reaction of the present invention, 3-dimethyl maleic anhydride, 2-methyl maleic anhydride, methacrylic acid, vinylformic acid and other product are as CO, CO
2
12, acid according to claim 1, the preparation method of ketone and derivative compound acid anhydrides thereof, it is characterized in that said catalyzer is by V, Nb, Mo, W, Ta, many metallic compounds of one or more among the Re are main other metallic compound promotor composition that adds, other metallic promoter agent is Si, B, Al, Ge, Ti, Zr, Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Ga, In, Tl, Sn, Pb, Tm, Sb, Bi, Dy, Hf, Cr, Yb, Mn, Ho, Sc, Y, La, Sm, Ce, Tb, Co, Ni, Cu, Zn, Cd, Pr, Nd, Eu, the oxide compound of Gd, oxyhydroxide, and/or their salt, and their mixture is formed.
The preparation method of 13, acid according to claim 12, ketone and derivative compound acid anhydrides thereof, the compound that it is characterized in that said catalyst component V, Nb, Mo, W, Ta, Re can be their oxide compound, salt, complex compound and organometallics.
The preparation method of 14, acid according to claim 12, ketone and derivative compound acid anhydrides thereof, it is characterized in that said catalyzer is loaded catalyst or body facies pattern catalyzer, many metallic compounds of one or more among V, Nb, Mo, W, Ta, the Re are main, add that other metallic compound promotor forms active phase.If loaded catalyst, activity is supported on the carrier mutually.
The preparation method of 15, acid according to claim 14, ketone and derivative compound acid anhydrides thereof, it is characterized in that said support of the catalyst is oxide compound, oxyhydroxide and/or their salt of Si, B, Al, Ge, Ti, Zr, Mg, Ca, Sr, Ba, Sn, Pb, Tm, Sb, Bi, Dy, Hf, Cr, Yb, Mn, Ho, Sc, Y, La, Sm, Ce, Tb, Co, Ni, Cu, Zn, V, Nb, Mo, W, Ta, Re, Cd, Pr, Nd, Eu, Gd, and their mixture is formed.
The preparation method of 16, acid according to claim 1, ketone and derivative compound acid anhydrides thereof is characterized in that said oxidation disproportionation catalyzed reaction can carry out between 150 ℃ to 600 ℃.
The preparation method of 17, acid according to claim 1, ketone and derivative compound acid anhydrides thereof is characterized in that said oxidation disproportionation catalyzed reaction can carry out between 0.05MPa to 20MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2004100228495A CN1640861A (en) | 2004-01-17 | 2004-01-17 | Alkane, alkene and substituted arene catalytic oxidation disproportionation for preparing acid and its derivatives |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2004100228495A CN1640861A (en) | 2004-01-17 | 2004-01-17 | Alkane, alkene and substituted arene catalytic oxidation disproportionation for preparing acid and its derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1640861A true CN1640861A (en) | 2005-07-20 |
Family
ID=34868387
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2004100228495A Pending CN1640861A (en) | 2004-01-17 | 2004-01-17 | Alkane, alkene and substituted arene catalytic oxidation disproportionation for preparing acid and its derivatives |
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|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112619645A (en) * | 2019-09-24 | 2021-04-09 | 中国石油化工股份有限公司 | Catalyst for preparing acrylic acid and preparation method and application thereof |
-
2004
- 2004-01-17 CN CNA2004100228495A patent/CN1640861A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112619645A (en) * | 2019-09-24 | 2021-04-09 | 中国石油化工股份有限公司 | Catalyst for preparing acrylic acid and preparation method and application thereof |
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