WO2023096263A1 - 카보네이트의 제조 방법 - Google Patents
카보네이트의 제조 방법 Download PDFInfo
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- WO2023096263A1 WO2023096263A1 PCT/KR2022/018154 KR2022018154W WO2023096263A1 WO 2023096263 A1 WO2023096263 A1 WO 2023096263A1 KR 2022018154 W KR2022018154 W KR 2022018154W WO 2023096263 A1 WO2023096263 A1 WO 2023096263A1
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- WO
- WIPO (PCT)
- Prior art keywords
- catalyst
- product
- remover
- carbonate
- reaction
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 145
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 45
- 239000002994 raw material Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 30
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 25
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 21
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 20
- 235000006408 oxalic acid Nutrition 0.000 claims description 15
- 238000006386 neutralization reaction Methods 0.000 claims description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 7
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 52
- 230000007547 defect Effects 0.000 abstract description 7
- 239000000047 product Substances 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000376 reactant Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- -1 NaOCH 3 Chemical compound 0.000 description 5
- 238000002296 dynamic light scattering Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920006375 polyphtalamide Polymers 0.000 description 5
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- GZCKIUIIYCBICZ-UHFFFAOYSA-L disodium;benzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 GZCKIUIIYCBICZ-UHFFFAOYSA-L 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
Definitions
- the present invention relates to a method for preparing carbonates.
- the present invention relates to a method for efficiently removing a catalyst used in a carbonate production reaction.
- EMC Ethyl methyl carbonate
- DEC diethyl carbonate
- EMC and DEC are mainly used as organic solvents for battery electrolytes.
- EMC and DEC are produced by transesterification of dimethyl carbonate (DMC) and ethanol (EtOH).
- the reaction is also a reversible reaction. Also, the reaction may proceed in the presence of a catalyst. At this time, as a catalyst, a basic catalyst is mainly used.
- Figure 1 below shows the reaction (where MeOH is an abbreviation for methanol):
- a basic catalyst mainly a metal salt containing an alkali metal or an alkaline earth metal as a metal component
- the catalyst has low solubility in carbonate, which is a reactant or product of the reaction. Therefore, if the catalyst is not separately removed, defects in subsequent processes may occur. This is because the precipitated catalyst causes column plugging or fouling in a later process.
- sodium methoxide or sodium ethoxide may be mentioned, which are strongly basic and water-repellent. Therefore, when the catalyst is exposed to the atmosphere as it is in the process of removing or replacing the catalyst using a filter or the like, a stability problem may also occur.
- Patent Document 1 introduces the production of dimethyl carbonate through reactive distillation using a NaOCH 3 catalyst and removal of the catalyst by applying a metal sintering filter. However, since Patent Document 1 removes the catalyst with a filter, a safety problem may occur by exposing the catalyst to air or moisture in the process of replacing the filter.
- Patent Document 1 CN 104557554 A
- the present invention is intended to safely remove the catalyst used in the carbonate production reaction.
- the present invention is to prevent defects that may occur due to a catalyst in a process of purifying a product of a carbonate production reaction.
- the method of the present invention can produce carbonate in high yield.
- the present invention applies a specific catalyst remover that removes the catalyst applied to the above reaction.
- the catalyst remover may form a salt with the catalyst.
- the method for producing a carbonate of the present invention includes a reaction step of reacting raw materials including dimethyl carbonate and ethanol in the presence of a catalyst to produce a product including ethylmethyl carbonate and diethyl carbonate.
- DMC dimethyl carbonate
- EtOH ethanol
- EMC ethylmethyl carbonate
- DEC diethyl carbonate
- MeOH methanol
- the raw material may include DMC and EtOH in a molar ratio (EtOH/DMC) within the range of 0.5 to 2.0.
- a continuous flow reactor may be used as the reactor.
- a continuous flow reactor is a reactor in which the supply of reactants and the outflow of products occur continuously.
- Continuous flow reactors can be broadly classified into two types. The first is a continuous stirred tank flow reactor or mixed flow reactor (CSTR or MFR) and the second is a plug flow reactor (PFR). Among them, the CSTR can keep the composition between components constant in the reactor. In the present invention, a uniform reaction can be performed by applying CSTR to the reactor. That is, in one embodiment, the reaction step may be to react the raw material in a continuous stirred tank reactor (CSTR).
- CSTR continuous stirred tank reactor
- the reaction proceeds in the presence of a catalyst.
- Catalysts applicable to the reaction are sodium methoxide (NaOCH 3 ), sodium ethoxide (NaOC 2 H 5 ), potassium hydroxide (Potassium Hydroxide, KOH), sodium hydroxide (Sodium Hydroxide, NaOH ) and the like.
- sodium methoxide or sodium methoxide, NaOCH 3 , Sodium Methoxide; SME
- Carbonates in the reactants or products do not dissolve the catalyst, but alcohols in the reactants or products can dissolve the catalyst. Accordingly, the product may include a predetermined amount of sodium ions (Na + ).
- the method for producing carbonate of the present invention includes a catalyst neutralization step of generating a neutralized salt of the catalyst and the catalyst remover by adding a catalyst remover to the product.
- the catalyst remover may react with the catalyst to produce neutralized salt and methanol, ethanol or water.
- the rest of the components except for the neutralization salt depend on the type of catalyst.
- the catalyst used in the above reaction is usually a basic component
- the catalyst remover capable of producing a salt by appropriate neutralization reaction is an acidic component.
- the catalyst remover capable of generating a salt by proceeding with a neutralization reaction therewith is a strong acid component. Therefore, the catalyst remover applied in the method of the present invention has a pKa value of 2.0 or less.
- the pH value of the product containing the catalyst remover may also change.
- the catalyst neutralization step may include adding the catalyst remover so that the pH of the product into which the catalyst remover is added is in the range of 5 to 8.
- the product can have a desired pH even when a relatively small amount of the catalyst remover is used.
- the catalyst neutralization step may include adding the catalyst remover within a range of 0.7 times to 1 time based on the weight of the catalyst.
- Other acidic compounds can be applied as catalyst removers, but their application must be substantial in order to achieve the desired pH of the product.
- the method for preparing carbonate of the present invention includes a neutralized salt removal step of removing the neutralized salt generated in the catalyst neutralization step.
- a neutralized salt removal step of removing the neutralized salt generated in the catalyst neutralization step.
- a reaction product from which the neutral salt is removed can be produced. Since the neutralized salt is present as a solid in the reaction product, it may cause defects in a subsequent process, so it must be removed. That is, in the present invention, before obtaining a product by purifying a product containing the neutralized salt formed by the catalyst, the neutralized salt formed by the catalyst must be removed from the product.
- the target product is carbonate.
- DEC is used as a solvent for secondary battery electrolyte, but as mentioned above, the demand for EMC is also significant. Therefore, in the method of the present invention, a process of separating a specific compound (DEC or EMC) as a target product from carbonates included in the product flow may be performed according to business importance.
- the method according to the present invention may include all other steps known to be necessary in the process for preparing the carbonate compound and the process for removing the catalyst used therein.
- the selectivity of the product, diethyl carbonate was calculated by mol% of the content of diethyl carbonate relative to the total content of ethylmethyl carbonate and diethyl carbonate.
- the selectivity of the product, ethylmethyl carbonate was calculated by mol% of the content of ethylmethyl carbonate relative to the total content of ethylmethyl carbonate and diethyl carbonate.
- a raw material solution was prepared by mixing 90.1 g (1 mol) of DMC and 46.07 g (1 mol) of EtOH. The moisture content of the raw material was 65 ppm.
- a catalyst solution was prepared by dissolving the SME catalyst in methanol at a concentration of 30% by weight. The SME catalyst was introduced into a reactor having a volume of 500 mL along with the raw material solution at a rate of 0.04% by weight based on the DMC weight of the raw material.
- the reaction pressure was maintained at 1 bar
- the reaction temperature was maintained at 50 °C
- the transesterification reaction was carried out at a stirring speed of 500 rpm for 1 hour.
- the conversion of DMC in the product was 54 mol%
- the selectivity of EMC was 82 mol%
- the selectivity of DEC was 18 mol%.
- oxalic acid OA
- a catalyst remover 0.82 times the weight of the catalyst.
- the pH of the product and the particle size of the solid precipitate were analyzed.
- Particle size was measured using a dynamic light scattering photometer (DLS).
- the product was filtered through a syringe filter made of PTFE with a pore size of 1 ⁇ m.
- the sodium content of the filtered product was measured by ICP.
- Example 2 The same procedure as in Example 1 was performed, except that a raw material solution having a water content of 94 ppm was prepared and the SME catalyst was added to the reactor at an amount of 0.05% by weight based on the DMC weight of the raw material.
- Example 2 The same procedure as in Example 1 was performed, except that a raw material solution having a water content of 130 ppm was prepared and the SME catalyst was added to the reactor at an amount of 0.067% by weight based on the DMC weight of the raw material.
- Example 2 The same procedure as in Example 1 was performed, except that a raw material solution having a water content of 150 ppm was prepared and the SME catalyst was added to the reactor at an amount of 0.073% by weight based on the DMC weight of the raw material.
- Example 1 Except for preparing a raw material solution having a water content of 91 ppm, introducing the catalyst solution into the reactor at a rate of 0.05% by weight based on the DMC weight of the raw material, and injecting PPA 1.2 times the weight of the catalyst as a catalyst remover, The same process as in Example 1 was performed.
- Example 1 Except for preparing a raw material solution having a water content of 65 ppm, introducing the catalyst solution into the reactor at a rate of 0.04% by weight based on the DMC weight of the raw material, and injecting IPA 1.6 times the weight of the catalyst as a catalyst remover, The same process as in Example 1 was performed.
- Example 1 Except for preparing a raw material solution having a water content of 130 ppm, introducing the catalyst solution into the reactor at a rate of 0.07% by weight based on the DMC weight of the raw material, and injecting IPA 1.6 times the weight of the catalyst as a catalyst remover, The same process as in Example 1 was performed.
- the Na content of the product filtered through the filter is 0.50 ⁇ 0.64 mg / L, which is similar to the Na content present in the raw material. That is, it was confirmed that the filter removed all neutralized salts generated by the addition of OA.
- Comparative Examples using polyphosphoric acid with a pKa of 2.16 Comparative Example 1
- isophthalic acid with a pKa of 3.46 Comparative Examples 2 and 3
- 1.5 to 2 times more catalyst remover should be used than the example in which OA is applied. It can be seen that the pH of 12 decreases to about 7-8.
- the particle size of the neutralized salts prepared in Comparative Example was 1 ⁇ m or more, but the Na content of the filtered product was 2.83 to 6.18 mg/L. That is, it was confirmed that the filter did not remove all of the neutralized salts generated by the addition of PPA or IPA. It is believed that this is because the neutral salts produced by PPA and IPA have high solubility in water so that the product stream dissolves the neutral salts.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
구분 | 실시예 1 | 실시예 2 | 실시예 3 | 실시예 4 | 비교예 1 | 비교예 2 | 비교예 3 | |
Acid | 종류 | OA | OA | OA | OA | PPA | IPA | IPA |
pKa | 1.25 | 1.25 | 1.25 | 1.25 | 2.16 | 3.46 | 3.46 | |
원료 내 수분 함량 (ppm) |
65 | 94 | 130 | 150 | 91 | 65 | 130 | |
촉매 함량(wt%, DMC 기준) | 0.04 | 0.05 | 0.067 | 0.073 | 0.05 | 0.04 | 0.07 | |
Acid/촉매(Mass ratio) | 0.82 | 0.82 | 0.82 | 0.82 | 1.2 | 1.6 | 1.6 | |
Acid 주입 후 pH | 5.8 | 5.9 | 6.2 | 6.5 | 7.5 | 8.1 | 8.4 | |
Na-Salt 평균 입자 크기(μm) | 1.32 (1.1~2.1) |
1.56 (1.1~2.3) |
1.84 (1.3~2.7) |
1.92 (1.5~2.8) |
2.0 (1.3~3.6) |
2.5 (2.1~3.6) |
2.5 (2.0~3.2) |
|
필터 후 Na 함량 (mg/L) |
0.52 | 0.51 | 0.64 | 0.50 | 18.7 | 2.83 | 6.18 | |
100℃ 증류 후 EMC 및 DEC 내 Na-Salt 석출 여부 |
X | X | X | X | O | O | O | |
Na-Salt Solubility in 100g Water (g, @20℃) | 3.7 | 3.7 | 3.7 | 3.7 | 100 | 37 | 37 | |
OA: Oxalic Acid PPA: Polyphosporic Acid IPA: Isophthalic acid Na-Salt: Sodium Oxalate, Sodium Polyphosphate, Sodium Isophthalate |
Claims (8)
- 디메틸 카보네이트 및 에탄올을 포함하는 원료를 촉매의 존재 하에 반응시켜서, 에틸메틸 카보네이트 및 디에틸 카보네이트를 포함하는 생성물을 제조하는, 반응 단계;상기 생성물에 촉매 제거제를 투입하여 상기 촉매와 촉매 제거제의 중화염을 생성시키는, 촉매 중화 단계; 및상기 중화염을 제거하는, 중화염 제거 단계;를 포함하고,상기 촉매 제거제는 pKa 값이 2.0 이하인,카보네이트의 제조 방법.
- 제1 항에 있어서,상기 촉매 제거제는 선형 디카르복시산인 것인,카보네이트의 제조 방법.
- 제2 항에 있어서,상기 촉매 제거제는 옥살산인 것인,카보네이트의 제조 방법.
- 제1 항에 있어서,상기 반응 단계는 수분 함량이 20 ppm 내지 500 ppm 범위 내인 원료를 반응시키는 것인,카보네이트의 제조 방법.
- 제1 항에 있어서,상기 반응 단계는 상기 디메틸 카보네이트의 중량을 기준으로 0.02 중량% 내지 0.2 중량% 범위 내의 촉매를 사용하는 것인,카보네이트의 제조 방법.
- 제1 항에 있어서,상기 촉매 중화 단계는 상기 촉매 제거제를 투입한 생성물의 pH가 5 내지 8 범위 내가 되도록 상기 촉매 제거제를 투입하는 것인,카보네이트의 제조 방법.
- 제1 항에 있어서,상기 촉매 중화 단계는 상기 촉매의 중량 대비 0.7 배 내지 1 배 범위 내의 상기 촉매 제거제를 투입하는 것인,카보네이트의 제조 방법.
- 제1 항에 있어서,상기 촉매는 소듐 메톡사이드, 소듐 에톡사이드, 포타슘 하이드록사이드, 또는 소듐 하이드록사이드인 것인,카보네이트의 제조 방법.
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Citations (3)
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KR100725335B1 (ko) * | 2006-07-20 | 2007-06-07 | (주)퓨렉스에너지 | 고순도 메틸에스테르의 정제방법 |
CN104557554A (zh) | 2014-12-11 | 2015-04-29 | 山东石大胜华化工集团股份有限公司 | 一种酯交换法连续化生产碳酸二甲酯联产1,2-丙二醇的方法 |
KR101823619B1 (ko) * | 2013-06-21 | 2018-01-30 | 사빅 글로벌 테크놀러지스 비.브이. | 고 품질 및 우수한 가공성을 구비한 광학 특성 제품을 제조하기 위한 폴리카보네이트 조성물 |
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2021
- 2021-11-25 KR KR1020210164916A patent/KR20230077544A/ko not_active Application Discontinuation
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2022
- 2022-11-17 CN CN202280076162.6A patent/CN118265689A/zh active Pending
- 2022-11-17 WO PCT/KR2022/018154 patent/WO2023096263A1/ko active Application Filing
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KR101823619B1 (ko) * | 2013-06-21 | 2018-01-30 | 사빅 글로벌 테크놀러지스 비.브이. | 고 품질 및 우수한 가공성을 구비한 광학 특성 제품을 제조하기 위한 폴리카보네이트 조성물 |
CN104557554A (zh) | 2014-12-11 | 2015-04-29 | 山东石大胜华化工集团股份有限公司 | 一种酯交换法连续化生产碳酸二甲酯联产1,2-丙二醇的方法 |
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