BR112012027617B1 - Método para produção de alquileno glicol - Google Patents
Método para produção de alquileno glicol Download PDFInfo
- Publication number
- BR112012027617B1 BR112012027617B1 BR112012027617-4A BR112012027617A BR112012027617B1 BR 112012027617 B1 BR112012027617 B1 BR 112012027617B1 BR 112012027617 A BR112012027617 A BR 112012027617A BR 112012027617 B1 BR112012027617 B1 BR 112012027617B1
- Authority
- BR
- Brazil
- Prior art keywords
- catalyst
- reaction
- liquid
- hydrolysis
- alkali metal
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 143
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 152
- 239000007788 liquid Substances 0.000 claims abstract description 118
- 238000006243 chemical reaction Methods 0.000 claims abstract description 101
- -1 alkylene glycol Chemical compound 0.000 claims abstract description 82
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 28
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 28
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 27
- 239000002244 precipitate Substances 0.000 claims abstract description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 76
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 62
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 35
- 239000001569 carbon dioxide Substances 0.000 claims description 31
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 31
- 238000004821 distillation Methods 0.000 claims description 31
- 238000000926 separation method Methods 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 18
- 238000011084 recovery Methods 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 114
- 230000007062 hydrolysis Effects 0.000 abstract description 93
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 42
- 238000009833 condensation Methods 0.000 description 19
- 230000005494 condensation Effects 0.000 description 19
- 150000004045 organic chlorine compounds Chemical class 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 17
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000001103 potassium chloride Substances 0.000 description 7
- 235000011164 potassium chloride Nutrition 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- RLZMYANQLOCZOB-UHFFFAOYSA-M tributyl(methyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](C)(CCCC)CCCC RLZMYANQLOCZOB-UHFFFAOYSA-M 0.000 description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001784 detoxification Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical group [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- IKZOMJGRWIOEDP-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dioxolane Chemical compound ClCC1OCCO1 IKZOMJGRWIOEDP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 229910001503 inorganic bromide Inorganic materials 0.000 description 2
- 229910001505 inorganic iodide Inorganic materials 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VCEVTCDKSHGBSX-UHFFFAOYSA-N 3,3,3-triphenylpropylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC[PH3+])C1=CC=CC=C1 VCEVTCDKSHGBSX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JOZHCQBYRBGYAJ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 JOZHCQBYRBGYAJ-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-103785 | 2010-04-28 | ||
| JP2010103785 | 2010-04-28 | ||
| JP2010158779 | 2010-07-13 | ||
| JP2010-158779 | 2010-07-13 | ||
| PCT/JP2011/059855 WO2011136127A1 (ja) | 2010-04-28 | 2011-04-21 | アルキレンカーボネート及び／又はアルキレングリコールの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112012027617A2 BR112012027617A2 (pt) | 2016-08-09 |
| BR112012027617B1 true BR112012027617B1 (pt) | 2021-11-09 |
Family
ID=44861433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012027617-4A BR112012027617B1 (pt) | 2010-04-28 | 2011-04-21 | Método para produção de alquileno glicol |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JP5725019B2 (ko) |
| KR (2) | KR101671155B1 (ko) |
| CN (1) | CN102858727B (ko) |
| BR (1) | BR112012027617B1 (ko) |
| SG (1) | SG185059A1 (ko) |
| TW (1) | TWI511947B (ko) |
| WO (1) | WO2011136127A1 (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5902985B2 (ja) * | 2012-03-30 | 2016-04-13 | 株式会社日本触媒 | エチレングリコール類の製造方法 |
| JP2014148481A (ja) * | 2013-02-01 | 2014-08-21 | Mitsubishi Chemicals Corp | アルキレンカーボネートの製造方法 |
| WO2020120305A1 (en) * | 2018-12-10 | 2020-06-18 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of ethylene glycol |
| CN109867654B (zh) * | 2019-02-19 | 2021-06-29 | 胜华新能源科技(东营)有限公司 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
| KR102150240B1 (ko) * | 2019-10-14 | 2020-09-01 | 그린케미칼 주식회사 | 알킬렌카보네이트 제조 장치 및 그를 이용한 제조 방법 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5690029A (en) * | 1979-12-24 | 1981-07-21 | Nippon Shokubai Kagaku Kogyo Co Ltd | Preparation of high-purity alkylene glycol |
| SG74047A1 (en) * | 1997-04-30 | 2000-07-18 | Mitsubishi Chem Corp | Process for producing alkylene glycol |
| JP3690129B2 (ja) * | 1998-08-10 | 2005-08-31 | 三菱化学株式会社 | アルキレングリコールの製造方法 |
| JP3921847B2 (ja) | 1998-11-13 | 2007-05-30 | 三菱化学株式会社 | エチレングリコールの製造方法 |
| JP3921843B2 (ja) * | 1998-10-27 | 2007-05-30 | 三菱化学株式会社 | エチレングリコールの製造方法 |
| JP3750376B2 (ja) * | 1998-11-06 | 2006-03-01 | 三菱化学株式会社 | エチレングリコールの製造方法 |
| JP2001031601A (ja) * | 1999-07-14 | 2001-02-06 | Nippon Shokubai Co Ltd | 高純度モノエチレングリコールの製造方法 |
| US6437199B1 (en) * | 1999-07-14 | 2002-08-20 | Nippon Shokubai Co., Ltd. | Method for production of high-purity monoethylene glycol |
| JP2001031600A (ja) * | 1999-07-14 | 2001-02-06 | Nippon Shokubai Co Ltd | 高純度モノエチレングリコールの製法 |
| JP4333153B2 (ja) * | 2003-02-07 | 2009-09-16 | 三菱化学株式会社 | アルキレングリコールの製造方法 |
| JP4273802B2 (ja) | 2003-03-27 | 2009-06-03 | 三菱化学株式会社 | アルキレン誘導体の製造方法 |
| WO2004069777A1 (ja) * | 2003-02-07 | 2004-08-19 | Mitsubishi Chemical Corporation | アルキレン誘導体の製造方法及びアルキレン誘導体製造用触媒の再生方法 |
| PE20070478A1 (es) * | 2005-08-02 | 2007-05-18 | Shell Int Research | Proceso de preparacion de alquilenglicoles |
-
2011
- 2011-04-21 JP JP2012512808A patent/JP5725019B2/ja active Active
- 2011-04-21 SG SG2012079554A patent/SG185059A1/en unknown
- 2011-04-21 BR BR112012027617-4A patent/BR112012027617B1/pt active IP Right Grant
- 2011-04-21 CN CN201180021036.2A patent/CN102858727B/zh active Active
- 2011-04-21 KR KR1020167008016A patent/KR101671155B1/ko active IP Right Grant
- 2011-04-21 WO PCT/JP2011/059855 patent/WO2011136127A1/ja active Application Filing
- 2011-04-21 KR KR1020127030331A patent/KR101663347B1/ko active IP Right Grant
- 2011-04-27 TW TW100114639A patent/TWI511947B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20160039307A (ko) | 2016-04-08 |
| SG185059A1 (en) | 2012-12-28 |
| BR112012027617A2 (pt) | 2016-08-09 |
| KR101663347B1 (ko) | 2016-10-06 |
| TWI511947B (zh) | 2015-12-11 |
| WO2011136127A1 (ja) | 2011-11-03 |
| JP5725019B2 (ja) | 2015-05-27 |
| TW201141820A (en) | 2011-12-01 |
| KR20130056242A (ko) | 2013-05-29 |
| CN102858727A (zh) | 2013-01-02 |
| CN102858727B (zh) | 2014-09-24 |
| KR101671155B1 (ko) | 2016-10-31 |
| JPWO2011136127A1 (ja) | 2013-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B25A | Requested transfer of rights approved |
Owner name: MITSUBISHI RAYON CO. LTD. (JP) |
|
| B25D | Requested change of name of applicant approved |
Owner name: MITSUBISHI CHEMICAL CORPORATION (JP) |
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| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
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