CN101395114A - Method for preventing generation of heavy component of butanone - Google Patents
Method for preventing generation of heavy component of butanone Download PDFInfo
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- CN101395114A CN101395114A CNA2007800073528A CN200780007352A CN101395114A CN 101395114 A CN101395114 A CN 101395114A CN A2007800073528 A CNA2007800073528 A CN A2007800073528A CN 200780007352 A CN200780007352 A CN 200780007352A CN 101395114 A CN101395114 A CN 101395114A
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- China
- Prior art keywords
- butanone
- sample
- dimerization
- prevents
- zinc
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 title claims abstract description 161
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 29
- 239000011701 zinc Substances 0.000 claims abstract description 23
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 11
- 239000010935 stainless steel Substances 0.000 claims abstract description 9
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 9
- 239000004615 ingredient Substances 0.000 claims description 37
- 238000006471 dimerization reaction Methods 0.000 claims description 27
- 239000004411 aluminium Substances 0.000 claims description 10
- HXFVOUUOTHJFPX-UHFFFAOYSA-N alumane;zinc Chemical compound [AlH3].[Zn] HXFVOUUOTHJFPX-UHFFFAOYSA-N 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 239000011135 tin Substances 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 229920005672 polyolefin resin Polymers 0.000 claims description 3
- 238000000746 purification Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 43
- 229910000975 Carbon steel Inorganic materials 0.000 description 16
- 239000010962 carbon steel Substances 0.000 description 16
- 238000007789 sealing Methods 0.000 description 10
- 239000007921 spray Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 238000007598 dipping method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 208000005156 Dehydration Diseases 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/10—Methyl-ethyl ketone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Abstract
A method for preventing the production of a heavy component of methyl ethyl ketone, which comprises using a dimerization-preventing material for at least the surface of a purification apparatus or a storage apparatus (50) which is in contact with methyl ethyl ketone. The dimerization-preventive material used in the purification device is preferably stainless steel, and the dimerization-preventive material used in the storage device (50) is preferably zinc or aluminum.
Description
Technical field
The present invention relates to prevent the method that the heavy ingredient of butanone generates.More specifically, relate in preparation or storage and prevent that the method for generation of the heavy ingredient that causes because of the butanone dimerization and butanone are with purifier apparatus or storage facilities during butanone.
Background technology
Butanone (MEK) mainly is as the useful compound of solvent, can synthesize (for example with reference to non-patent literature 1) by the dehydrogenation reaction of 2-butanols.Below, the preparation process of simple declaration butanone.
Fig. 1 is the general flowchart that shows the preparation process of butanone.
Dehydrogenation reaction takes place in raw material 2-butanols (note is made SBA among the figure) in dehydrogenation reaction tower 10, generate butanone (note is made MEK among the figure).Next, raw material and butanone are sent in the MEK separation column 20 separated.In separation column 20, take out butanone from cat head, at the bottom of tower, take out the 2-butanols.The 2-butanols that reclaims is reused as raw material.Butanone after the fractionation comprises a spot of water byproduct, therefore dewaters with dehydration tower 30.Afterwards, again butanone is sent in the purification column 40, removed heavy ingredient by the generations such as dimerization of butanone, thus the butanone of preparation goods purity, and keeping is in storage facilities 50.
So operation and synthesize, there is following problem in the butanone of purifying.
1. heavy ingredient increase between maintaining period in storage facilities can not be satisfied the goods specification sometimes.
2. by in purification column, carrying out lock out operation, should contain heavy ingredient hardly in the butanone behind the purifying, even but behind purifying the heavy ingredient of residual minim still.
Non-patent literature 1: (1986) 565 pages of No. the 8th, chemical engineering the 50th volumes
The present invention establishes in view of the above problems, the method that provides the heavy ingredient that prevents to reduce butanone purity to generate.
Summary of the invention
The inventor etc. further investigate in order to solve above-mentioned problem, and the result is conceived to the material of equipment used in purification step or the storage part.In purifier apparatus or storage facilities, only otherwise handle corrodibility composition such as acid, use cheap materials such as carbon steel usually.In the preparation of butanone, owing to do not have the composition of etching apparatus, so also use carbon steel.
But, when the carbon steel oxidation, confirm that ferric oxide becomes catalyzer and makes the butanone dimerization.Therefore, find by with equipment that butanone contact in the suitable material of use, can prevent the dimerization of butanone, thereby finish the present invention.
According to the present invention, can provide the following method that prevents the heavy ingredient generation of butanone.
1. prevent the method that the heavy ingredient of butanone generates, this method be purifier apparatus or storage facilities at least with face that butanone contact on use prevent the material of dimerization.
2.1 the method that generates of the heavy ingredient that prevents butanone, wherein above-mentionedly prevent that the material of dimerization from being zinc, aluminium, aluminium zinc, tin, stainless steel, fluorine-type resin or polyolefin resin.
3.2 the method that generates of the heavy ingredient that prevents butanone, the material that prevents dimerization that uses in the wherein above-mentioned purifier apparatus is stainless steel.
4.3 the method that generates of the heavy ingredient that prevents butanone, wherein above-mentioned purifier apparatus is for the condenser of cooling butanone and/or temporarily receive the receptor of butanone.
5.2 the method that generates of the heavy ingredient that prevents butanone, the material that prevents dimerization that uses in the wherein above-mentioned storage facilities is zinc, aluminium, aluminium zinc or tin.
6. butanone is with purifier apparatus or storage facilities, wherein comprises the material that prevents dimerization at least with on the face that butanone contacts.
In the method that the heavy ingredient that prevents butanone of the present invention generates, can prevent that butanone from when purification step or storage dimerization taking place, and therefore is fit to keep the quality of goods.
The accompanying drawing summary
Fig. 1 is the general flowchart that shows the purification step of butanone.
Fig. 2 is the general flowchart that shows the preparation process of butanone.
The best mode that carries out an invention
The method that the heavy ingredient that prevents butanone of the present invention generates is characterized in that: in the purifier apparatus or storage facilities of butanone, at least with face that butanone contact on use prevent the material of dimerization.
Fig. 1 is the general flowchart that shows the purification step of butanone.Fig. 1 shows the purification step through the butanone of dehydration tower shown in Figure 2 30 dehydrations.
Purified tower 40 distillations of the butanone of dehydration are reclaimed with gas form from cat head.The gasiform butanone is accommodated in the receptor 44 through condenser 42 coolings, liquefaction.The butanone that accumulates in the receptor 44 is sent in the purification column 40 as required once more, removes heavy ingredient, until satisfying the goods specification.And when satisfying specification, being cooled to normal temperature through water cooler 46, keeping is in storage facilities 50.Need to prove that butanone is carried through pump P.
Prevent in the method that the butanone heavy ingredient generates of the present invention, in storage facilities such as purifier apparatus such as condenser 42, receptor 44 or water cooler 46 and/or storage tank, use the material that prevents dimerization.
The material that prevents dimerization can use: metallic substance such as zinc, tin, stainless steel, aluminium, aluminium zinc; Or resin materials such as fluorine-type resin, polyolefin resin such as tetrafluoroethylene etc.Can also use the material (sealing of hole processing) that is coated with silicon-dioxide or waters such as zinc or aluminium is handled the overlay film that forms the oxyhydroxide that comprises them.
Need to prove, as long as equipment at least with face that butanone contact on use prevent the material of dimerization, therefore for example can form entire equipment, also can implement plating or molten spray etc., form the film that comprises the material that prevents dimerization contact surface with the material that prevents dimerization.
In the present invention, the material that prevents dimerization that uses in the purifier apparatus is preferably stainless steel.In purification step, butanone all is in high temperature (more than 80 ℃) state before cooling off with water cooler.Therefore, for example in carbon steel, use in zinc-plated or zinc-plated etc. the purifier apparatus, sometimes coating Yin Gaowen and go bad, peel off or chap, the carbon steel of inside separates out, so might cause the dimerization of butanone.Therefore, particularly preferably in using stainless steel in condenser that contacts with the high temperature butanone and/or the receptor.Need to prove the preferred SUS304 of stainless steel, SUS316, SUS405, SUS410.
On the other hand, the preferred zinc of the material that prevents dimerization, aluminium, aluminium zinc or the tin that use in the storage facilities are preferably zinc or aluminium especially.Butanone by water cooler is cooled to normal temperature, therefore the aforesaid disadvantage that is caused by high temperature can not take place.Therefore, the preferred use comprises the equipment that more cheap material constitutes, for example at the equipment that connects molten spray zinc or aluminium etc. on the liquid level of carbon steel.
As mentioned above, butanone of the present invention is characterised in that with purifier apparatus or storage facilities: comprise the material that prevents dimerization at least with on the face that butanone contacts.The example of aforesaid device has: comprise stainless equipment or the molten equipment that has sprayed zinc or aluminium etc. on carbon steel.Aforesaid device can utilize in the field, chemical plant known method to make.
The butanone of the application of the invention can prevent the dimerization of butanone with purifier apparatus or storage facilities.
Below, as evaluation Example, in butanone, the result that the increase of the heavy ingredient during to dipping is estimated is illustrated with various material soakings.
Evaluation method
Each sample and butanone (MEK) are together put into the glass container, and be immersed in the maintenance homothermic thermostatic bath every gas chromatograph for determination heavy ingredient of using through after a while.In each test, also measure the heavy ingredient of blank (only MEK).
Evaluation Example 1
Respectively get the iron rust taked on the self-contained carbon steel of 1g open jar and the chip iron powder of rustless carbon steel.They are put into Glass Containers respectively, be immersed among the 50ml MEK (Idemitsu Kosen Co., Ltd.'s system).The growing amount of the heavy ingredient when the mensuration dipping temperature is 15 ℃～50 ℃.Measurement result sees Table 1.
Can be confirmed by this result: iron rust (ferric oxide) promotes the dimerization of MEK.
Evaluation Example 2
(30mm * 30mm * 3mm is thick, zinc coating thickness is 80 μ m: Sample A) and to Sample A implemented the sample (sample B) that the Si sealing of hole is handled to make the carbon steel sheet of two molten spray zinc respectively.Said sample is immersed among the 50ml MEK growing amount of the heavy ingredient when measuring dipping temperature and be 30 ℃ or 50 ℃.Measurement result sees Table 2.Compare with evaluation Example 1, the generation of the heavy ingredient of all samples all is inhibited.
[table 2]
In the table, the unit of heavy ingredient amount is (wtppm).
Sample A: the carbon steel of molten spray zinc
Sample B: the sample that Sample A is coated with the processing of execution sealing of hole with the alcoholic solvent silica gel (tetraethyl orthosilicate, Northeast chemistry (strain) society system) of hydrolysis
Evaluation Example 3
Each following sample (60mm * 50mm * 6mm is thick) is immersed among the 200ml MEK growing amount of the heavy ingredient when the mensuration dipping temperature is 35 ℃.Measurement result sees Table 3.Compare with evaluation Example 1, the generation of the heavy ingredient of all samples all is inhibited.
Sample C: the molten sample that sprays zinc (zinc thickness is 80 μ m) on carbon steel
Sample D: sample C has been carried out Zn (OH)
2Sealing of hole is handled and (is carried out the sample of washing and drying behind the molten spray zinc, by washing Zn (OH)
2Carrying out sealing of hole handles) sample
Sample E: sample C has been carried out the sample that the Resins, epoxy sealing of hole is handled (carrying out sealing of hole with two component normal-temperature curing epoxy resin behind the molten spray zinc handles)
Sample F: the molten sample that sprays aluminium zinc on carbon steel (alloy thickness is 80 μ m)
Sample G: sample F has been carried out Zn (OH)
2, Al (OH)
3Sealing of hole is handled and (is carried out the sample of washing and drying behind the molten spray aluminium zinc, by washing Zn (OH)
2, Al (OH)
3Carrying out sealing of hole handles) sample
Sample H: sample F has been carried out the sample that the Si sealing of hole identical with sample B handled
Sample I: white gas pipe (galvanized steel pipe)
Evaluation Example 4
Following sample (60mm * 50mm * 3mm is thick) is immersed among the 200ml MEK growing amount of the heavy ingredient when the mensuration dipping temperature is 35 ℃.Measurement result sees Table 4.
Sample J: jar channel-section steel plate (carbon steel)
Sample K: on carbon steel with zinc-rich paint (Northwest Paint (strain) society system, trade(brand)name: SD Zinc1500A) formed the sample of overlay film
Sample L: carbon steel is carried out Resins, epoxy (Northwest Paint (strain) society system, trade(brand)name: the MillionClear) sample of Bao Fuing
[table 4]
| Dipping time | Blank | Sample J | Sample K | Sample L |
| 25 hours | 53 | 802 | 63 | 48 |
| 191 hours | 58 | 968 | 98 | 53 |
| 312 hours | 55 | 976 | 101 | 52 |
| 570 hours | 54 | 985 | 133 | 49 |
| 981 hours | 61 | 987 | 169 | 50 |
| 1581 hours | 156 | 1096 | 193 | 54 |
| 2084 hours | 172 | 1206 | 210 | 47 |
In the table, the unit of heavy ingredient amount is (wt ppm).
Can confirm by this result: in sample K and L, can suppress the generation of heavy ingredient.But sample K except that detecting common heavy ingredient, also detects alcohols and ketone after through 1000 hours.In addition, in the sample that Resins, epoxy coats, detect the stripping composition of Resins, epoxy.Therefore, sample K and L are not suitable for the producing apparatus of MEK.
Industrial applicability
Utilize method, purifier apparatus or the storage facilities that prevents the heavy ingredient generation of butanone of the present invention, can prevent that butanone from the quality decline of butanone occuring when purifying or keeping.
Claims (6)
1. prevent the method that the heavy ingredient of butanone generates, this method be purifier apparatus or storage facilities at least with face that butanone contact on use prevent the material of dimerization.
2. the method that generates of the heavy ingredient that prevents butanone of claim 1 wherein above-mentionedly prevents that the material of dimerization from being zinc, aluminium, aluminium zinc, tin, stainless steel, fluorine-type resin or polyolefin resin.
3. the method that generates of the heavy ingredient that prevents butanone of claim 2, the material that prevents dimerization that uses in the wherein above-mentioned purifier apparatus is stainless steel.
4. the method that generates of the heavy ingredient that prevents butanone of claim 3, wherein above-mentioned purifier apparatus is for the condenser of cooling butanone and/or temporarily receive the receptor of butanone.
5. the method that generates of the heavy ingredient that prevents butanone of claim 2, the material that prevents dimerization that uses in the wherein above-mentioned storage facilities is zinc, aluminium, aluminium zinc or tin.
6. butanone is with purifier apparatus or storage facilities, wherein comprises the material that prevents dimerization at least with on the face that butanone contacts.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP055958/2006 | 2006-03-02 | ||
| JP2006055958A JP5001562B2 (en) | 2006-03-02 | 2006-03-02 | Method for preventing heavy formation of methyl ethyl ketone |
| PCT/JP2007/053003 WO2007099806A1 (en) | 2006-03-02 | 2007-02-20 | Method of preventing generation of heavy ingredient of methyl ethyl ketone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101395114A true CN101395114A (en) | 2009-03-25 |
| CN101395114B CN101395114B (en) | 2013-07-24 |
Family
ID=38458918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007800073528A Active CN101395114B (en) | 2006-03-02 | 2007-02-20 | Method for preventing generation of heavy component of butanone |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5001562B2 (en) |
| KR (1) | KR101314198B1 (en) |
| CN (1) | CN101395114B (en) |
| WO (1) | WO2007099806A1 (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW240219B (en) * | 1992-08-05 | 1995-02-11 | Exxon Chemical Patents Inc | |
| WO1998000382A1 (en) * | 1996-07-02 | 1998-01-08 | Toray Industries, Inc. | Processes for the preparation of optically active ketones |
| JPH10251189A (en) * | 1997-01-13 | 1998-09-22 | Toray Ind Inc | Preservation of optically active alpha-substituted cyclic ketone |
| JP2004051518A (en) * | 2002-07-18 | 2004-02-19 | Tonen Chem Corp | Method of producing ketone and/or aldehyde |
| JP2005336122A (en) * | 2004-05-28 | 2005-12-08 | Mitsubishi Chemicals Corp | Method for producing (meth)acrylic acid or (meth)acrylic acid ester |
-
2006
- 2006-03-02 JP JP2006055958A patent/JP5001562B2/en active Active
-
2007
- 2007-02-20 WO PCT/JP2007/053003 patent/WO2007099806A1/en active Application Filing
- 2007-02-20 CN CN2007800073528A patent/CN101395114B/en active Active
- 2007-02-20 KR KR1020087019873A patent/KR101314198B1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP5001562B2 (en) | 2012-08-15 |
| CN101395114B (en) | 2013-07-24 |
| JP2007230936A (en) | 2007-09-13 |
| KR20080112201A (en) | 2008-12-24 |
| KR101314198B1 (en) | 2013-10-02 |
| WO2007099806A1 (en) | 2007-09-07 |
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