CN109020789A - A method of preparing 2- methoxyl group propylene - Google Patents
A method of preparing 2- methoxyl group propylene Download PDFInfo
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- CN109020789A CN109020789A CN201710438118.6A CN201710438118A CN109020789A CN 109020789 A CN109020789 A CN 109020789A CN 201710438118 A CN201710438118 A CN 201710438118A CN 109020789 A CN109020789 A CN 109020789A
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- catalyst
- methoxyl group
- dimethoxypropane
- group propylene
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003426 co-catalyst Substances 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940095050 propylene Drugs 0.000 claims description 32
- 238000005336 cracking Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- -1 2- methoxy propyl Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 11
- 238000007233 catalytic pyrolysis Methods 0.000 abstract description 5
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009413 insulation Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a kind of methods for preparing 2- methoxyl group propylene.In existing synthetic system, some systems use solvent；Although solvent is not used in some systems, the usage amount of acid is especially big, is not easy industrialized production.The present invention is used as catalyst using p-methyl benzenesulfonic acid, and as co-catalyst, catalytic pyrolysis 2,2-dimethoxypropane prepares 2- methoxyl group propylene for pyridine, quinoline or hydroquinone etc.；Reaction time is 5-15h, and reaction temperature is 60-150 DEG C, and reaction pressure is normal pressure, and for product yield up to 93.0%, the purity that rectifying obtains product is 99.5%.Method of the invention does not both use solvent, does not introduce acid anhydrides yet, and reaction condition is mild, it can be achieved that continuous industrial production.
Description
Technical field
The present invention relates to a kind of methods for preparing 2- methoxyl group propylene, especially a kind of to use catalyst collocation co-catalyst,
The method that catalytic pyrolysis 2,2- dimethoxy propane prepares 2- methoxyl group propylene under normal pressure and higher temperature.
Background technique
2- methoxyl group propylene is critical materials in many pharmaceutical synthesis, and in material for a kind of important organic compound
The industrial circles such as material, medicine, dyestuff and feed are widely applied.Currently, main synthesis 2- methoxyl group propylene route has: 1, by
Methanol and unsaturated hydrocarbons addition reaction generate 2- methoxyl group propylene；2, it first passes through directly or indirectly method and synthesizes 2,2- dimethoxy
Base propane, then by gas phase or liquid phase method catalytic pyrolysis 2,2-dimethoxypropane, to prepare 2- methoxyl group propylene.Route
1 step is simple, and reaction yield is higher, and selectivity is also fine, but the catalytic reaction that this route has the disadvantage in that (1), is related to
Agent is very strong to equipment corrosion at high temperature；(2), unsaturated hydrocarbons chemical activity is high, and reaction is fierce, it is difficult to control, safe operation
Property is poor；(3), the source of unsaturated hydrocarbons propine used or allene is more difficult, only the large petrochemical plant of the raw material
It can just consider this synthetic route.The material benzenemethanol and acetone of 2 direct synthesis 2,2-dimethoxypropane of route are cheap and easy to get,
It is easily achieved the industrialized production of 2- methoxyl group propylene.However, since this condensation reaction transformation ratio is lower, and methanol and third
Ketone, 2,2-dimethoxypropane can all generate azeotropic mixture, make 2,2-dimethoxypropane the difficult point for being prepared into route thus it
One.Vapor-phase thermal cracking method is to be urged at high temperature after vaporizing 2,2-dimethoxypropane by the catalyst bed of heating in route 2
Change cracking, obtains 2- methoxyl group propylene.Because then to be cracked at high temperature, first by feed vaporization so vapor-phase thermal cracking
Method energy consumption is larger.And liquid-phase pyrolysis method can be under mild conditions by 2,2- dimethoxy propane catalytic pyrolysis.
About the research for preparing 2- methoxyl group propylene by 2,2-dimethoxypropane liquid-phase pyrolysis, scholar both domestic and external
Many work are done.
Xi'an Inst. of Modern Chemistry poplar it is refined it is quick et al. be published in the research of fine-chemical intermediate within 2002, with benzene first
As catalyst, diethylene glycol dimethyl ether is added a certain amount of succinic anhydride and generates to absorb cracking as solvent for acid and pyridine
Methanol come promote to react to the direction of 2- methoxyl group propylene carry out.Rectification yield is 80.06%, and product purity is greater than 98%.It should
System considerably increases cost due to the use of solvent and the introducing of succinic anhydride.
Wuhan University of Technology's Li Xiao sunlight et al. is published in the article of Anhui chemical industry for 2009, is made using benzoic acid and pyridine
For catalyst, toluene absorbs methanol as solvent, and with succinic anhydride.Product yield can reach 81.1%, and purity is greater than 97%.
In the system, although using toluene that diethylene glycol dimethyl ether is replaced to reduce costs as solvent.But the use of solvent and succinic acid
The introducing of acid anhydride keeps reaction system excessively complicated, brings inconvenience for post-reaction treatment.
Manfred Kaufhold uses n-nonanoic acid catalytic pyrolysis 2,2- at 130 DEG C in United States Patent (USP) US 5,576,465
Dimethoxy propane prepares 2- methoxyl group propylene, and conversion ratio can reach 78%, lysate first passes through washing, then obtains in rectifying
To can be obtained purity be 99.3% 2- methoxyl group propylene.Although solvent is not used in this system, the usage amount of n-nonanoic acid is special
Greatly, it is not easy industrialized production.
Summary of the invention
Solvent is not both used the object of the present invention is to provide a kind of, does not introduce acid anhydrides yet, efficient liquid phase cracks 2,2- diformazan
Oxygroup propane provides a kind of more reasonable industrialized production side come the method for preparing 2- methoxyl group propylene for 2- methoxyl group propylene
Method.
For this purpose, the technical solution adopted by the present invention are as follows: a method of 2- methoxyl group propylene is prepared, step includes:
Step a), mixing 2,2-dimethoxypropane, catalyst and co-catalyst；
Step b), 60-150 DEG C temperature cracking reaction 5-15 hours, obtain 2- methoxy propyl ene product；
Wherein, molar ratio=1:0.01%-5.0%:0.05%-8.0% of 2,2-dimethoxypropane, catalyst and co-catalyst；
The catalyst is selected from one or more mixtures of toluenesulfonic acid class compound, and co-catalyst is selected from pyridines
Close one of object, quinolines or benzenediol or a variety of mixtures.
Preferably, the 2- methoxy propyl ene product in step b) is again through washing and rectification step.
Preferably, the heating of step b) carries out under normal pressure.
Preferably, the reaction temperature in step b) is 80-120 DEG C.
Preferably, molar ratio=1:0.01%-2.0% of the 2,2-dimethoxypropane, catalyst and co-catalyst:
1.0%-8.0%。
Preferably, the catalyst is p-methyl benzenesulfonic acid.
Preferably, the co-catalyst is pyridine.
Preferably, the co-catalyst is quinoline.
Preferably, the co-catalyst is hydroquinone.
The present invention is not under the premise of introducing solvent and acid anhydrides, using a small amount of p-methyl benzenesulfonic acid and co-catalyst, in temperature
It is efficiently to crack 2,2-dimethoxypropane, after reaction 5-15 hours, lysate first passes through washing, rectifying obtains at 60-150 DEG C
To the 2- methoxyl group propylene of high-purity.The present invention synthesizes 2- methoxyl group propylene for pipeline successive reaction and provides new approaches and side
Formula.
Specific embodiment
Patent in order to better illustrate the present invention is specifically described by following embodiment, but the present invention is not by these
Any restrictions of embodiment, the present invention in product content and purity by gas chromatographic detection.
Embodiment 1
By 200g 2,2-dimethoxypropane, 0.3g p-methyl benzenesulfonic acid, 0.5g pyridine is added in 250ml there-necked flask, and unlatching is stirred
It mixes, heat temperature raising, control reaction temperature is 100 DEG C, and after insulation reaction 8h, cool processing.Pyrolysis product first passes through washing,
Then rectifying obtains the 2- methoxyl group propylene that purity is 99.3%, product yield 90.3%.
Embodiment 2
By 200g 2,2-dimethoxypropane, 0.5g p-methyl benzenesulfonic acid, 0.8g pyridine is added in 250ml there-necked flask, and unlatching is stirred
It mixes, heat temperature raising, control reaction temperature is 90 DEG C, and after insulation reaction 6.8h, cool processing.Pyrolysis product first passes through water
It washes, then rectifying obtains the 2- methoxyl group propylene that purity is 99.1%, product yield 91.8%.
Embodiment 3
By 200g 2,2-dimethoxypropane, 0.3g p-methyl benzenesulfonic acid, 0.5g quinoline is added in 250ml there-necked flask, and unlatching is stirred
It mixes, heat temperature raising, control reaction temperature is 100 DEG C, and after insulation reaction 10h, cool processing.Cracking product first passes through water
It washes, then rectifying obtains the 2- methoxyl group propylene that purity is 99.2%, product yield 92.5%.
Embodiment 4
By 200g 2,2-dimethoxypropane, 0.5g p-methyl benzenesulfonic acid, 0.8g quinoline is added in 250ml there-necked flask, and unlatching is stirred
It mixes, heat temperature raising, control reaction temperature is 90 DEG C, and after insulation reaction 9h, cool processing.Cracking product first passes through washing,
Then rectifying obtains the 2- methoxyl group propylene that purity is 99.1%, product yield 92.8%.
Embodiment 5
By 200g 2,2-dimethoxypropane, 0.3g p-methyl benzenesulfonic acid, 0.5g hydroquinone is added in 250ml there-necked flask, is opened
Stirring, heat temperature raising reaction after insulation reaction 13h, cool controlled at 100 DEG C.Cracking product first passes through washing,
Then rectifying obtains the 2- methoxyl group propylene that purity is 99.4%, product yield 89.7%.
Embodiment 6
By 200g 2,2-dimethoxypropane, 0.5g p-methyl benzenesulfonic acid, 0.8g hydroquinone is added in 250ml there-necked flask, is opened
Stirring, heat temperature raising reaction after insulation reaction 12h, cool controlled at 90 DEG C.Cracking product first passes through washing, so
Rectifying obtains the 2- methoxyl group propylene that purity is 99.2%, product yield 90.5% afterwards.
Comparative example 1
By 200g 2,2-dimethoxypropane, 0.5g p-methyl benzenesulfonic acid is added in 250ml there-necked flask, opens stirring, heat temperature raising
Reaction after insulation reaction 18h, cools controlled at 100 DEG C.Cracking product first passes through washing, and then rectifying obtains pure
The 2- methoxyl group propylene that degree is 98.4%, product yield 70.5%.
Comparative example 2
By 200g 2,2-dimethoxypropane, 0.5g phosphoric acid is added in 250ml there-necked flask, opens stirring, and heat temperature raising is anti-
It answers, controlled at 110 DEG C, after insulation reaction 20h, cools.Cracking product first passes through washing, and then rectifying obtains purity
For 96.7% 2- methoxyl group propylene, product yield 50.3%.
Comparative example 3
By 200g 2,2-dimethoxypropane, 0.5g phosphoric acid, 0.5g quinoline is added in 250ml there-necked flask, is opened stirring, is added
Hot temperature reaction after insulation reaction 17h, cools controlled at 110 DEG C.Cracking product first passes through washing, then rectifying
Obtain the 2- methoxyl group propylene that purity is 97.2%, product yield 56.6%.
Claims (9)
1. a kind of method for preparing 2- methoxyl group propylene, step includes:
Step a), mixing 2,2-dimethoxypropane, catalyst and co-catalyst；
Step b), 60-150 DEG C temperature cracking reaction 5-15 hours, obtain 2- methoxy propyl ene product；
Wherein, molar ratio=1:0.01%-5.0%:0.05%-8.0% of 2,2-dimethoxypropane, catalyst and co-catalyst；
The catalyst is selected from one or more mixtures of toluenesulfonic acid class compound, and co-catalyst is selected from pyridines
Close one of object, quinolines or benzenediol or a variety of mixtures.
2. the method according to claim 1, wherein 2- methoxy propyl ene product in step b) again through washing and
Rectification step.
3. the method according to claim 1, wherein the heating of step b) carries out under normal pressure.
4. the method according to claim 1, wherein the reaction temperature in step b) is 80-120 DEG C.
5. the method according to claim 1, wherein the 2,2-dimethoxypropane, catalyst and co-catalysis
Molar ratio=1:0.01%-2.0%:1.0%-8.0% of agent.
6. method according to claim 1-5, which is characterized in that the catalyst is p-methyl benzenesulfonic acid.
7. according to the method described in claim 6, it is characterized in that, the co-catalyst is pyridine.
8. according to the method described in claim 6, it is characterized in that, the co-catalyst is quinoline.
9. according to the method described in claim 6, it is characterized in that, the co-catalyst is hydroquinone.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724038A (en) * | 2019-11-06 | 2020-01-24 | 安徽华甬新材料股份有限公司 | Preparation method of methyl isopropenyl ether |
| CN111187149A (en) * | 2020-02-18 | 2020-05-22 | 万华化学集团股份有限公司 | Method for preparing 2-alkoxy propylene |
| CN114149310A (en) * | 2021-11-23 | 2022-03-08 | 万华化学(四川)有限公司 | Preparation method of unsaturated ketone |
| CN115490575A (en) * | 2022-10-13 | 2022-12-20 | 辽宁惠风生物医药科技有限公司 | Preparation method of 2-ethoxypropylene |
| CN116444352A (en) * | 2022-01-06 | 2023-07-18 | 万华化学集团股份有限公司 | Novel method for liquid phase synthesis of 2-methoxypropene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5576465A (en) * | 1994-09-23 | 1996-11-19 | Huels Aktiengesellschaft | Process for preparing unsaturated ethers |
| CN102015693A (en) * | 2008-02-21 | 2011-04-13 | 先灵公司 | Compounds that are ERK inhibitors |
-
2017
- 2017-06-12 CN CN201710438118.6A patent/CN109020789B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5576465A (en) * | 1994-09-23 | 1996-11-19 | Huels Aktiengesellschaft | Process for preparing unsaturated ethers |
| CN102015693A (en) * | 2008-02-21 | 2011-04-13 | 先灵公司 | Compounds that are ERK inhibitors |
Non-Patent Citations (12)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724038A (en) * | 2019-11-06 | 2020-01-24 | 安徽华甬新材料股份有限公司 | Preparation method of methyl isopropenyl ether |
| CN111187149A (en) * | 2020-02-18 | 2020-05-22 | 万华化学集团股份有限公司 | Method for preparing 2-alkoxy propylene |
| CN111187149B (en) * | 2020-02-18 | 2022-11-08 | 万华化学集团股份有限公司 | Method for preparing 2-alkoxy propylene |
| CN114149310A (en) * | 2021-11-23 | 2022-03-08 | 万华化学(四川)有限公司 | Preparation method of unsaturated ketone |
| CN116444352A (en) * | 2022-01-06 | 2023-07-18 | 万华化学集团股份有限公司 | Novel method for liquid phase synthesis of 2-methoxypropene |
| CN115490575A (en) * | 2022-10-13 | 2022-12-20 | 辽宁惠风生物医药科技有限公司 | Preparation method of 2-ethoxypropylene |
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