CN108097289A - A kind of renovation process for the catalyst for being used to prepare acrylic acid and/or methyl acrylate - Google Patents
A kind of renovation process for the catalyst for being used to prepare acrylic acid and/or methyl acrylate Download PDFInfo
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- CN108097289A CN108097289A CN201611054338.0A CN201611054338A CN108097289A CN 108097289 A CN108097289 A CN 108097289A CN 201611054338 A CN201611054338 A CN 201611054338A CN 108097289 A CN108097289 A CN 108097289A
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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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/12—Treating with free oxygen-containing gas
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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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
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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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7019—EMT-type, e.g. EMC-2, ECR-30, CSZ-1, ZSM-3 or ZSM-20
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/90—Regeneration or reactivation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a kind of renovation process of catalyst, wherein, the catalyst experienced by the raw material containing carbon monoxide and benzaldehyde compound to prepare acrylic acid and/or methyl acrylate, the described method includes in the atmosphere containing oxygen, the catalyst is regenerated at a temperature of 200 DEG C to 600 DEG C.
Description
Technical field
The present invention relates to a kind of renovation process for the catalyst for being used to prepare acrylic acid and/or methyl acrylate.
Background technology
Acrylic acid and methyl acrylate are a kind of important industrial chemicals, can be used as coating, flocculant, dispersant and bonding
The uses such as agent are widely used in industries such as building, water process, daily-use chemical industry, soil treatment and leathers, the daily life with people
Work is closely bound up.The industrial most common acrylic acid and the method for methyl acrylate of preparing is propylene two-stage oxidizing method at present, i.e.,
The propylene first step is oxidized to methacrylaldehyde, and further oxidation can obtain acrylic acid.However its raw material propylene belongs to non-from oil
Renewable resource does not meet sustainable development idea.
With the rapid development of C1 chemistry, cause acetic acid and methyl acetate excess capacity.With cheap raw material acetic acid and acetic acid
Methyl esters for raw material prepare acrylic acid and methyl acrylate for it is sustainable prepare acrylic acid and methyl acrylate provide one it is feasible
Route.
Catalyst is mostly basic catalyst or soda acid bifunctional catalysis' agent used by the studies above, preparation process one
As using dipping, ion exchange, co-precipitation the methods of active component is carried on carrier, there is prepare it is cumbersome, influence because
The shortcomings of plain complicated and repeated low and active ingredient is easy to run off, can not meet the needs of industrialization large-scale production.
The content of the invention
One of present invention provides a kind of method of regenerated catalyst, wherein, the catalyst experienced by containing an oxygen
Change the raw material of carbon and benzaldehyde compound to prepare acrylic acid and/or methyl acrylate, the described method includes containing oxygen
In atmosphere, the catalyst is regenerated at a temperature of 250 DEG C to 600 DEG C.
In a detailed embodiment, the benzaldehyde compound in formaldehyde, dimethoxym ethane, metaformaldehyde at least
It is a kind of.
In a detailed embodiment, in the atmosphere also containing in carbon dioxide, nitrogen, helium and argon gas at least
It is a kind of.
In a detailed embodiment, volume content of the oxygen in the atmosphere is 0.05% to 100%；It is excellent
It is 5% to 30% to select volume content of the oxygen in the atmosphere.
In a detailed embodiment, the regeneration carries out under 200 DEG C to 450 DEG C temperature conditionss.
In a detailed embodiment, the regeneration carries out under the pressure condition of 0.1Mpa to 10Mpa.
In a detailed embodiment, preferably described regeneration carries out under the pressure condition of 0.1Mpa to 3Mpa.
In a detailed embodiment, it is described regeneration carry out 1 hour to 500 it is small when；It is preferred that the regeneration progress 100 is small
When 200 is small.
In a detailed embodiment, the regenerated air speed is 500mL/g/h to 10000mL/g/h；It is it is preferred that described
Regenerated air speed is 3000mL/g/h to 5000mL/g/h.
In a detailed embodiment, acidic molecular sieve is contained in the catalyst.
In a detailed embodiment, in preferably described catalyst contain with RHO, CHA, FER, MFI, MOR, FAU,
At least one of acidic molecular sieve of EMT structures.
In a detailed embodiment, more preferably in the catalyst containing DNL-6 molecular sieves, SAPO-34 molecular sieves,
FER molecular sieve, ZSM-35 molecular sieve, ZSM-21 molecular sieves, ZSM-38 molecular sieves, FU-9 molecular sieves, β eta molecular sieves, ZSM-5
At least one of molecular sieve, MOR molecular sieves, EMT molecular sieves, Y molecular sieve.
In a detailed embodiment, the acidic molecular sieve is metal-modified acidic molecular sieve.
In a detailed embodiment, the metal is selected from least one of gallium, iron, copper and silver.
In a detailed embodiment, preferably with metal atoms, the quality of single metal in the catalyst contains
It measures as 0.01wt% to 10.0wt%.
In a detailed embodiment, preferably with metal atoms, most preferably single metal is in the catalyst
Mass content is 0.05wt% to 1wt%
In a detailed embodiment, binding agent is also contained in the catalyst.
In a detailed embodiment, preferably described binding agent is mesoporous binding agent.
In the present invention, mesoporous binding agent refers to the binding agent to 50nm apertures containing 2nm.
In a detailed embodiment, more preferably the binding agent is selected from silica, magnesia, titanium oxide, the thin water of plan
At least one of aluminium stone, kaolin and montmorillonite.
In a detailed embodiment, the mass content in the catalyst of most preferably described binding agent for 5wt% extremely
50wt%.
In a detailed embodiment, the atomic ratio of silicon and aluminium in the acid molecular sieve catalyst is further optimized
Si/Al=3-100.
In a detailed embodiment, the atomic ratio Si/Al of silicon and aluminium in the ZSM-35 molecular sieve is further optimized
=5-100.
In a detailed embodiment, the atomic ratio Si/Al=of silicon and aluminium in the ZSM-5 molecular sieve is further optimized
5-100。
In a detailed embodiment, the atomic ratio Si/Al=5- of silicon and aluminium in the modenite is further optimized
50。
In a detailed embodiment, the reaction condition for preparing acrylic acid and/or methyl acrylate is as follows：Temperature is
200 DEG C to 400 DEG C, pressure is 0.2Mpa to 15.0Mpa, and the combined feed air speed of unstripped gas is 0.05h-1To 10.0h-1。
In a detailed embodiment, the reaction condition for preparing acrylic acid and/or methyl acrylate is as follows：Temperature is
300 DEG C to 350 DEG C, pressure is 0.2Mpa to 5.0Mpa, and the combined feed air speed of unstripped gas is 0.3h-1To 2h-1。
The two of the present invention provide a kind of to be prepared by the raw material containing carbon monoxide and benzaldehyde compound and catalyst
The method of acrylic acid and/or methyl acrylate, the catalyst are regenerated to obtain as the method described in one of present invention, prepare propylene
The reaction condition of acid and/or methyl acrylate is as follows：Temperature be 200 DEG C to 400 DEG C, pressure be 0.2Mpa to 15.0Mpa, raw material
The combined feed air speed of gas is 0.05h-1To 10.0h-1。
In a detailed embodiment, the reaction condition for preparing acrylic acid and/or methyl acrylate is as follows：Temperature is
300 DEG C to 350 DEG C, pressure is 0.2Mpa to 5.0Mpa, and the combined feed air speed of unstripped gas is 0.3h-1To 2h-1。
In a detailed embodiment, the ratio of the integral molar quantity of the mole and benzaldehyde compound of the carbon monoxide
1:1 to 200:1.
In a detailed embodiment, the ratio of the integral molar quantity of the mole and benzaldehyde compound of the carbon monoxide
For 1:1 to 100:1.
In a detailed embodiment, the ratio of the integral molar quantity of the mole and benzaldehyde compound of the carbon monoxide
For 2:1.
In a detailed embodiment, the reactor of the reaction zone is selected from tank reactor, fixed bed reactors, shifting
One kind in dynamic bed reactor and fluidized-bed reactor.
Beneficial effects of the present invention include but not limited to：
1) there is the renovation process for a kind of catalyst for preparing acrylic acid and methyl acrylate that the application provides reaction to live
Property high, Catalystization prepare the features such as simple, catalytic active component not easily runs off, there is good prospects for commercial application.
2) renovation process for a kind of catalyst for preparing acrylic acid and methyl acrylate that the application provides, advantage can
The basic initial performance for recovering fresh catalyst, and limited from regeneration times.
Specific embodiment
The present invention is described in detail with reference to embodiment, but the invention is not limited in these embodiments.
Unless otherwise instructed, the raw material in the embodiment of the present invention is bought by commercial sources.
In the present invention, dimethoxym ethane and reaction of carbon monoxide, generation dimethyl ether, acetic acid, methyl acetate, acrylic acid and acrylic acid
The compounds such as methyl esters.By thermodynamics and kinetics factor, control different temperatures and stress reaction condition and different proportion are former
The conditions such as material composition, can be carried out with the generation of oriented control product according to following equation.Under ideal conditions, propylene in product
Total carbon selectivity of acid is 60%, and total carbon selectivity 40% of acetic acid is generated without other by-products.It is if former with single reaction
Expect that dimethoxym ethane calculates selectivity of product, then acrylic acid carbon mole element selectivity is 50%, the carbon molal quantity selectivity of acetic acid
50%.
The present invention raw material and product by agilent company Aligent 7890A gas-chromatographies, using agilent company
FFAP capillary post detections.Crystallite dimension is obtained by stereoscan photograph.Median particle diameter D50It is measured by laser particle analyzer.
A kind of embodiment according to the present invention, selection fixed bed reactors, catalyst filling quality 0.5g to 3.0g, instead
Answer 180 DEG C to 350 DEG C of temperature, reaction pressure 0.1Mpa to 10Mpa.Raw material dimethoxym ethane is by carbon monoxide, in different water-bath temperature
The saturated vapor that dimethoxym ethane is carried under the conditions of degree (0 to 50 DEG C) is entered in fixed bed reactors, to obtain different volumes content
Dimethoxym ethane unstrpped gas.The computational methods of the saturated vapour pressure of raw material dimethoxym ethane are shown below under condition of different temperatures：
Ln (p1*/p2*)=- Δ vapHm/8.3145 × (1/T1-1/T2)
Wherein p1* and p2* represents the saturated vapour pressure of dimethoxym ethane under different temperatures (T1, T2) respectively.Known dimethoxym ethane rubs
Your vaporization enthalpy Δ vapHm=43.99KJ/mol, boiling point are 42.3 DEG C, can thus calculate the full of dimethoxym ethane under arbitrary temp
And vapour pressure.The amount that raw material dimethoxym ethane substance in reactor is entered in the unit interval can be calculated by saturated vapour pressure.
Conversion ratio, selectivity calculate as follows in the embodiment of the present invention：
Dimethoxym ethane conversion ratio=[(dimethoxym ethane molal quantity in charging)-(dimethoxym ethane molal quantity in discharging)] ÷ (first in charging
Acetal molal quantity) × (100%)
Acrylic acid selectivity=2/3 (the carbon molal quantity of acrylic acid in discharging) ÷ [(carbon mole of dimethoxym ethane in charging
Number)-(the carbon molal quantity of dimethoxym ethane in discharging)] × (100%)
Methyl acrylate selectively=3/4 (the carbon molal quantity of methyl acrylate in discharging) ÷ [(carbon of dimethoxym ethane in charging
Molal quantity)-(the carbon molal quantity of dimethoxym ethane in discharging)] × (100%)
Acetic acid selectivity=1/2 (the carbon molal quantity of acetic acid in discharging) ÷ [(the carbon molal quantity of dimethoxym ethane in charging)-(go out
The carbon molal quantity of dimethoxym ethane in material)] × (100%)
Methyl acetate selectively=2/3 (the carbon molal quantity of methyl acetate in discharging) ÷ [(carbon mole of dimethoxym ethane in charging
Number)-(the carbon molal quantity of dimethoxym ethane in discharging)] × (100%).
Catalyst preparation
1 H- mordenite catalysts of embodiment
The Na- modenite zeolite molecular sieves that 100 grams of roasting aluminium atom molar ratios are 25 (are bought in Shanghai respectively
Zhuo Yue Chemical Industry Science Co., Ltd) exchanged three times with 0.5mol/L ammonium nitrate, every time 2 it is small when, be washed with deionized, it is dry,
When 550 DEG C of roastings 4 are small, 20-40 mesh catalyst is prepared into through squeezing, is named as 1#.
2 H- mordenite catalysts of embodiment are molded
Sial atomic molar is taken (to buy public affairs limited in Shanghai Zhuo Yue chemical science and technologies than the 80gNa- modenites for 6.5
Department), 28g boehmites and 10% dust technology extruded moulding after mixing, after roasting, with 0.5mol/L ammonium nitrate exchange three
Secondary when small (2/time), are washed with deionized, dry, when 550 DEG C of roastings 4 are small, catalyst are made, is named as 2#.
Sial atomic molar is taken than the 80gNa- modenites (buying in Shanghai Zhuoyue Chemical Science Co., Ltd) for 4,
20g magnesia and 10% dust technology extruded moulding after mixing, after roasting, are exchanged three times with 0.5mol/L ammonium nitrate, and every time 2
Hour, it is washed with deionized, it is dry, when 550 DEG C of roastings 4 are small, catalyst is made, is named as 3#.
3 H-ZSM-35 catalyst of embodiment
Respectively by 100 grams of roasting sial atomic molars than (being bought for 35 Na-ZSM-35 molecular sieves in Shanghai Zhuo Yue
Chemical Industry Science Co., Ltd) exchanged three times with 0.5mol/L ammonium nitrate, every time 2 it is small when, be washed with deionized, it is dry, 550
DEG C roasting 4 it is small when, through squeeze be prepared into 20-40 mesh catalyst, be named as 4#.
4 H-ZSM-5 catalyst of embodiment
Respectively by 100 grams of roasting sial atomic molars than (being bought for 40 Na-ZSM-5 molecular sieves in Shanghai Zhuo Yue
Chemical Industry Science Co., Ltd) exchanged three times with 0.5mol/L ammonium nitrate, every time 2 it is small when, be washed with deionized, it is dry, 550
DEG C roasting 4 it is small when, through squeeze be prepared into 20-40 mesh catalyst, be named as 5#.
5 H-EMT catalyst of embodiment
Respectively by sial atomic molar than the H-EMT molecular sieves (buying in Shanghai Zhuoyue Chemical Science Co., Ltd) for 10
20-40 mesh catalyst, which is prepared into, through extruding is named as 6#.
Embodiment 6
5g catalyst is filled into fixed bed reactors, carries out pre-treatment.Catalyst pre-treatment condition is：N2Flow velocity
30mL/min rises to 500 DEG C through 150min since 25 DEG C, and keeps 180min under the conditions of 500 DEG C.Carbon monoxide is carried
Dimethoxym ethane gaseous mixture pass through reactor under conditions of 250 DEG C, pressure 5MPa, air speed=2400mL/g/h of temperature.Wherein gas
Body flow 200mL/min, CO/DMM=20/1 (volume ratio).The result and regenerated outcome of catalyst reaction are listed in table 1.
Table 1
The above is only several embodiments of the present invention, any type of limitation is not done to the present invention, although this hair
It is bright to be disclosed as above with preferred embodiment, however not to limit the present invention, any person skilled in the art is not taking off
In the range of technical solution of the present invention, make a little variation using the technology contents of the disclosure above or modification is equal to
Case study on implementation is imitated, is belonged in the range of technical solution.
Claims (10)
1. a kind of method of regenerated catalyst, wherein, the catalyst experienced by containing carbon monoxide and benzaldehyde compound
Raw material prepare acrylic acid and/or methyl acrylate,
The described method includes in the atmosphere containing oxygen, the catalyst is regenerated at a temperature of 200 DEG C to 600 DEG C.
2. according to the method described in claim 1, it is characterized in that, the benzaldehyde compound is selected from formaldehyde, dimethoxym ethane, trimerization
At least one of formaldehyde；
Also containing at least one of carbon dioxide, nitrogen, helium and argon gas in the atmosphere；
It is preferred that volume content of the oxygen in the atmosphere is 0.05% to 100%；The more preferable oxygen is in the gas
Volume content in atmosphere is 5% to 30%.
3. according to the method described in claim 1, it is characterized in that, it is described regeneration under 200 DEG C to 450 DEG C temperature conditionss into
Row.
4. according to the method described in claim 1, it is characterized in that, the regeneration is under the pressure condition of 0.1Mpa to 10Mpa
It carries out；
It is preferred that the regeneration carries out under the pressure condition of 0.1Mpa to 3Mpa.
5. according to the method described in claim 1, it is characterized in that, it is described regeneration carry out 1 hour to 500 it is small when；It is it is preferred that described
Regeneration carry out 100 hours to 200 it is small when.
6. according to the method described in claim 1, it is characterized in that, the regenerated air speed is 500mL/g/h to 10000mL/
g/h；It is preferred that the regenerated air speed is 3000mL/g/h to 5000mL/g/h.
7. according to the method described in claim 1, it is characterized in that, contain acidic molecular sieve in the catalyst；
It is preferred that contain in the catalyst in the acidic molecular sieve with RHO, CHA, FER, MFI, MOR, FAU, EMT structure extremely
Few one kind；
In the more preferable catalyst containing DNL-6 molecular sieves, SAPO-34 molecular sieves, FER molecular sieve, ZSM-35 molecular sieve,
ZSM-21 molecular sieves, ZSM-38 molecular sieves, FU-9 molecular sieves, β eta molecular sieves, ZSM-5 molecular sieve, MOR molecular sieves, EMT molecules
At least one of sieve, Y molecular sieve.
8. the method according to the description of claim 7 is characterized in that the acidic molecular sieve is metal-modified acidic molecular
Sieve；
The metal is selected from least one of gallium, iron, copper and silver；
It is preferred that with metal atoms, the mass content of single metal in the catalyst is 0.01wt% to 10wt%；It is optimal
The mass content of menu kind metal in the catalyst is 0.05wt% to 1wt%.
9. according to the method described in claim 1, it is characterized in that, also contain binding agent in the catalyst；
It is preferred that the binding agent is mesoporous binding agent；
The more preferable binding agent in silica, magnesia, titanium oxide, boehmite, kaolin and montmorillonite extremely
Few one kind；
The mass content in the catalyst of most preferably described binding agent is 5wt% to 50wt%.
10. according to the method described in claim 1, it is characterized in that, prepare the reaction condition of acrylic acid and/or methyl acrylate
It is as follows：Temperature is 200 DEG C to 400 DEG C, and pressure is 0.2Mpa to 15.0Mpa, and the combined feed air speed of unstripped gas is 0.05h-1Extremely
10.0h-1；
It is preferred that the reaction condition for preparing acrylic acid and/or methyl acrylate is as follows：Temperature is 300 DEG C to 350 DEG C, and pressure is
0.2Mpa to 5.0Mpa, the combined feed air speed of unstripped gas is 0.3h-1To 2h-1。
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101311159A (en) * | 2007-05-25 | 2008-11-26 | 罗姆有限公司 | Process for preparation of methyl methacrylate by esterification during oxidation |
| WO2010048300A1 (en) * | 2008-10-23 | 2010-04-29 | The Regents Of The University Of California | Gas-phase catalyzed production of alkyl alkoxyacetates from dialkoxymethanes |
| CN102775302A (en) * | 2012-08-03 | 2012-11-14 | 北京旭阳化工技术研究院有限公司 | Method for preparing methyl methacrylate from methyl propionate and formaldehyde |
| CN103492070A (en) * | 2011-04-27 | 2014-01-01 | 国际人造丝公司 | Catalyst for producing acrylic acids and acrylates |
| CN103752305A (en) * | 2014-01-17 | 2014-04-30 | 旭阳化学技术研究院有限公司 | Catalyst, preparation method thereof, and method for production of methyl acrylate and co-production of methyl methacrylate by using catalyst |
-
2016
- 2016-11-25 CN CN201611054338.0A patent/CN108097289B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101311159A (en) * | 2007-05-25 | 2008-11-26 | 罗姆有限公司 | Process for preparation of methyl methacrylate by esterification during oxidation |
| WO2010048300A1 (en) * | 2008-10-23 | 2010-04-29 | The Regents Of The University Of California | Gas-phase catalyzed production of alkyl alkoxyacetates from dialkoxymethanes |
| CN103492070A (en) * | 2011-04-27 | 2014-01-01 | 国际人造丝公司 | Catalyst for producing acrylic acids and acrylates |
| CN102775302A (en) * | 2012-08-03 | 2012-11-14 | 北京旭阳化工技术研究院有限公司 | Method for preparing methyl methacrylate from methyl propionate and formaldehyde |
| CN103752305A (en) * | 2014-01-17 | 2014-04-30 | 旭阳化学技术研究院有限公司 | Catalyst, preparation method thereof, and method for production of methyl acrylate and co-production of methyl methacrylate by using catalyst |
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