JP6872303B2 - メタクリル酸メチルの精製のための方法 - Google Patents
メタクリル酸メチルの精製のための方法 Download PDFInfo
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- JP6872303B2 JP6872303B2 JP2018528028A JP2018528028A JP6872303B2 JP 6872303 B2 JP6872303 B2 JP 6872303B2 JP 2018528028 A JP2018528028 A JP 2018528028A JP 2018528028 A JP2018528028 A JP 2018528028A JP 6872303 B2 JP6872303 B2 JP 6872303B2
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- Prior art keywords
- mixture
- distillation column
- methyl methacrylate
- tray
- column
- Prior art date
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 20
- 238000000746 purification Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 27
- 238000004821 distillation Methods 0.000 claims description 24
- 239000007795 chemical reaction product Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 16
- -1 alkali metal salts Chemical class 0.000 claims description 9
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 238000006709 oxidative esterification reaction Methods 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 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
- 241000183024 Populus tremula Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- 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
-
- 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
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/36—Azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/40—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of primary alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本実験は、図1に示される方法の配置を用いて実施される。蒸留カラムは、内径28mmの30個のトレイからなるOldershawカラムであり、n−ヘキサンは、共沸剤溶媒として採用される。流れを加熱する熱対流式再沸騰器は、カラムにおける沸騰を提供するために使用される。カラムの上部の圧力は、700mmHgの絶対値である。オーバヘッドの温度は48℃であり、底部の温度は83℃である。
60%のトレイ効率を想定した、30個のトレイからなる蒸留カラム(トレイ1は最上段トレイである)における供給位置のASPENシミュレーションは、カラムに再循環されたMMA%について以下の結果をもたらした。
Claims (9)
- メタクリル酸メチルを精製するための方法であって、(a)メタノール、メタクリル酸メチル及びそのアルカリ金属塩、メタクロレイン、水、ならびに重副生物を含む反応産物の混合物を、少なくとも15個のトレイを有する蒸留カラムへ供給すること、ここで、前記反応産物の混合物は、メタクロレインおよびメタノールからメチルメタクリレートを調製するための酸化的エステル化反応産物の混合物であり、前記反応産物の混合物及びC6−C7炭化水素が、前記蒸留カラムの中央より上で前記蒸留カラムへ入る、(b)C6−C7炭化水素、メタクロレイン、メタノール、水、及びメタクリル酸メチルを含むオーバヘッド流を取り出すことと、(c)水、メタクリル酸メチル及びそのアルカリ金属塩、ならびに重副生物を含む塔底流を取り出すことと、を含む、方法。
- 前記反応産物の混合物が、少なくとも0.8重量%のメタクリル酸メチルの前記ナトリウム塩を含む、請求項1に記載の方法。
- 前記反応産物の混合物が、1〜10重量%の水を含む、請求項2に記載の方法。
- 前記反応産物の混合物が、上から30%までの前記トレイにおいて前記蒸留カラムへ入る、請求項3に記載の方法。
- C6−C7炭化水素が、65〜100℃の雰囲気圧沸点を有する飽和炭化水素である、請求項4に記載の方法。
- 前記オーバヘッド流の一部が、上から30%までの前記トレイにおいて前記蒸留カラムへ戻り、前記カラムへ入る前記オーバヘッド流中のC6−C7炭化水素の量が、前記反応産物の混合物中のメタノールの量の2〜10倍である、請求項5に記載の方法。
- 前記反応産物の混合物が、上から20%までの前記トレイにおいて前記蒸留カラムへ入る、請求項6に記載の方法。
- 前記蒸留カラムが、20〜40個のトレイを有する、請求項7に記載の方法。
- 前記反応産物の混合物が、上から4個までの前記トレイにおいて前記蒸留カラムへ入る、請求項8に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562269458P | 2015-12-18 | 2015-12-18 | |
US62/269,458 | 2015-12-18 | ||
PCT/US2016/065324 WO2017105955A1 (en) | 2015-12-18 | 2016-12-07 | Process for purification of methyl methacrylate |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2018537465A JP2018537465A (ja) | 2018-12-20 |
JP2018537465A5 JP2018537465A5 (ja) | 2021-03-04 |
JP6872303B2 true JP6872303B2 (ja) | 2021-05-19 |
Family
ID=57589259
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018528028A Active JP6872303B2 (ja) | 2015-12-18 | 2016-12-07 | メタクリル酸メチルの精製のための方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US10597349B2 (ja) |
EP (1) | EP3390341B1 (ja) |
JP (1) | JP6872303B2 (ja) |
KR (1) | KR102638541B1 (ja) |
CN (1) | CN108368024B (ja) |
CA (1) | CA3008384C (ja) |
MX (1) | MX2018007378A (ja) |
SA (1) | SA518391737B1 (ja) |
SG (1) | SG11201804739TA (ja) |
TW (1) | TW201722903A (ja) |
WO (1) | WO2017105955A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102612750B1 (ko) | 2022-01-12 | 2023-12-13 | 주식회사 썬플라워즈 | 구명동의 및 해양사고에 따른 구명동의 탐색 네트워크 시스템 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1490688A (fr) * | 1966-06-22 | 1967-08-04 | Melle Usines Sa | Procédé pour séparer les constituants de mélanges azéotropiques de méthanol et d'ester aliphatique inférieur |
JPS579739A (en) * | 1980-06-20 | 1982-01-19 | Asahi Chem Ind Co Ltd | Purification of methyl methacrylate |
JPS579740A (en) * | 1980-06-20 | 1982-01-19 | Asahi Chem Ind Co Ltd | Purification of methyl methacrylate |
EP0044409B1 (en) * | 1980-06-20 | 1984-01-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for purifying methyl methacrylate |
JP2582127B2 (ja) | 1988-07-04 | 1997-02-19 | 株式会社クラレ | メタクリル酸メチルの精製法 |
JP2859682B2 (ja) * | 1989-03-31 | 1999-02-17 | 三井化学株式会社 | メタクリル酸メチルの精製方法及び製造方法 |
CA2012935A1 (en) * | 1989-03-31 | 1990-09-30 | Hirozo Segawa | Purification and preparation processes for methyl methacrylate |
US5435892A (en) | 1993-08-30 | 1995-07-25 | Mitsubishi Rayon Co., Ltd. | Process for separating methanol and methyl acrylate or methyl methacrylate |
JP3819419B2 (ja) * | 2006-04-21 | 2006-09-06 | 旭化成ケミカルズ株式会社 | メタクロレイン及びメタノールの回収方法 |
CN103833551A (zh) | 2012-11-27 | 2014-06-04 | 华东理工大学工程设计研究院有限公司 | 一种甲基丙烯酸甲酯的分离设备及分离方法 |
MY176555A (en) * | 2013-04-19 | 2020-08-16 | Roehm Gmbh | Method for producing methylmethacrylate |
SG11201704540YA (en) * | 2014-12-03 | 2017-07-28 | Nippon Catalytic Chem Ind | Method for purifying easily polymerizable substance |
TWI715627B (zh) * | 2015-09-16 | 2021-01-11 | 德商羅伊姆公司 | 含鈉鹽之mma-甲醇混合物的萃取後處理 |
TW201739730A (zh) * | 2015-12-18 | 2017-11-16 | 陶氏全球科技責任有限公司 | 用於純化甲基丙烯酸甲酯之方法 |
-
2016
- 2016-11-22 TW TW105138315A patent/TW201722903A/zh unknown
- 2016-12-07 MX MX2018007378A patent/MX2018007378A/es unknown
- 2016-12-07 JP JP2018528028A patent/JP6872303B2/ja active Active
- 2016-12-07 WO PCT/US2016/065324 patent/WO2017105955A1/en active Application Filing
- 2016-12-07 CN CN201680070871.8A patent/CN108368024B/zh active Active
- 2016-12-07 CA CA3008384A patent/CA3008384C/en active Active
- 2016-12-07 SG SG11201804739TA patent/SG11201804739TA/en unknown
- 2016-12-07 EP EP16816140.4A patent/EP3390341B1/en active Active
- 2016-12-07 KR KR1020187018301A patent/KR102638541B1/ko active IP Right Grant
- 2016-12-07 US US15/776,847 patent/US10597349B2/en active Active
-
2018
- 2018-06-05 SA SA518391737A patent/SA518391737B1/ar unknown
Also Published As
Publication number | Publication date |
---|---|
US20180346402A1 (en) | 2018-12-06 |
BR112018010955A2 (pt) | 2018-12-04 |
SA518391737B1 (ar) | 2021-10-06 |
CA3008384A1 (en) | 2017-06-22 |
MX2018007378A (es) | 2018-08-14 |
SG11201804739TA (en) | 2018-07-30 |
EP3390341A1 (en) | 2018-10-24 |
CN108368024B (zh) | 2022-02-25 |
CA3008384C (en) | 2023-12-12 |
WO2017105955A1 (en) | 2017-06-22 |
JP2018537465A (ja) | 2018-12-20 |
TW201722903A (zh) | 2017-07-01 |
KR20180094935A (ko) | 2018-08-24 |
EP3390341B1 (en) | 2019-09-25 |
CN108368024A (zh) | 2018-08-03 |
KR102638541B1 (ko) | 2024-02-20 |
US10597349B2 (en) | 2020-03-24 |
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