JP2023514477A - ハロゲン化アルコキシエタンの調製 - Google Patents
ハロゲン化アルコキシエタンの調製 Download PDFInfo
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- JP2023514477A JP2023514477A JP2022537885A JP2022537885A JP2023514477A JP 2023514477 A JP2023514477 A JP 2023514477A JP 2022537885 A JP2022537885 A JP 2022537885A JP 2022537885 A JP2022537885 A JP 2022537885A JP 2023514477 A JP2023514477 A JP 2023514477A
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- Prior art keywords
- halogenated
- flow
- alkoxyethane
- reactor
- tubular
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 112
- 230000008569 process Effects 0.000 claims abstract description 97
- 238000002156 mixing Methods 0.000 claims abstract description 55
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- 150000003839 salts Chemical class 0.000 claims abstract description 14
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- 238000006243 chemical reaction Methods 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 claims description 42
- 239000012074 organic phase Substances 0.000 claims description 42
- 150000001412 amines Chemical class 0.000 claims description 41
- 229960002455 methoxyflurane Drugs 0.000 claims description 33
- 238000000746 purification Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 23
- 239000002798 polar solvent Substances 0.000 claims description 22
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
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- 238000010438 heat treatment Methods 0.000 claims description 8
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- DPRMFUAMSRXGDE-UHFFFAOYSA-N ac1o530g Chemical group NCCN.NCCN DPRMFUAMSRXGDE-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 4
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 4
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 4
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
- CRUVUWATNULHFA-UHFFFAOYSA-M tetramethylphosphanium;hydroxide Chemical compound [OH-].C[P+](C)(C)C CRUVUWATNULHFA-UHFFFAOYSA-M 0.000 claims description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 52
- -1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy Chemical group 0.000 description 30
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- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 16
- 230000003068 static effect Effects 0.000 description 16
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- 238000010923 batch production Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
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- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical compound FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
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- 238000007796 conventional method Methods 0.000 description 4
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 4
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- HCDYMSGTJTXKIL-UHFFFAOYSA-N 1,1-dichloro-2-fluoro-2-methoxyethene Chemical compound COC(F)=C(Cl)Cl HCDYMSGTJTXKIL-UHFFFAOYSA-N 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KKXBMWAROXAWSZ-UHFFFAOYSA-N 2-chloro-1,1,2-trifluoro-1-methoxyethane Chemical compound COC(F)(F)C(F)Cl KKXBMWAROXAWSZ-UHFFFAOYSA-N 0.000 description 1
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- 239000000575 pesticide Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
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- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
Description
a)フロー反応器が、1以上の管状フローラインを含み、このフローラインを通って反応成分が反応混合物として流れ、
b)ハロゲン化アルコキシエタンが少なくとも反応成分の混合時に形成され、そのように形成されたハロゲン化アルコキシエタンがフロー反応器から反応器流出液に流出し、
c)塩基が、ハロゲン化アルコキシエタンの形成中にアルカノールに可溶な塩を形成するものである
プロセスに関する。
2,2-ジクロロ-1,1,1-トリフルオロエタン(Cl2HC-CF3又はHCFC-123)及びメタノール中の水酸化テトラメチルアンモニウムの溶液(25wt%)を、図3の概略図で示す設定に従い、最小限の時間で完全に混合できるように周囲温度に維持したスタティック(乱流)ミキサーに個別にポンプ圧送した。
実施例2で得られた二相混合物を分離及び乾燥する際、粗メトキシフルラン溶液を化学的に処理して不純物を除去した。不純物の性質上、分留による直接除去だけでは十分な効果が得られないことが確認された。
実施例1に記載した種類の装置の設定を用いて、以下の表1に記載するように、異なるプロセスパラメータを用いていくつかの反応を実施した。フロー反応器及びそれぞれの管状フローラインの具体的なパラメータは以下の通りであった。
管状フローラインの総内部体積:100ml
個々の管状フローラインの直径(内径):1/4インチ(6.35mm)
管状フローラインの配置:4×3の線形配列
スタティックミキサー(フロー反応器内に設置):あり
管状フローライン加熱ジャケット:あり、>100℃
表中、GCはガスクロマトグラフィー、RTはコンジットシステムでの滞留時間、TMAHは水酸化テトラメチルアンモニウムである。
Claims (24)
- 一般式XClHC-CF2OR(式中、Xは-Cl又は-Fであり、ORはC1-4アルコキシである)のハロゲン化アルコキシエタンの連続調製のためのプロセスであって、(i)一般式XClHC-CYF2(式中、X及びYの各々は独立して-Cl又は-Fである)の化合物と、(ii)塩基と、(iii)C1-4アルカノールとを含む反応成分をフロー反応器に導入する工程を含み、
a)前記フロー反応器が1以上の管状フローラインを含み、当該フローラインを通って前記反応成分が反応混合物として流れ、
b)前記ハロゲン化アルコキシエタンが少なくとも前記反応成分の混合時に形成され、そのように形成されたハロゲン化アルコキシエタンが前記フロー反応器から反応器流出液に流出し、
c)前記塩基が、前記ハロゲン化アルコキシエタンの形成中に前記アルカノールに可溶な塩を形成するものである、プロセス。 - 前記1以上の管状フローラインが、約115mm2未満の内部断面積を有する、請求項1に記載のプロセス。
- 一般式XClHC-CF2OR(式中、Xは-Cl又は-Fであり、ORはC1-4アルコキシである)のハロゲン化アルコキシエタンの連続調製のためのプロセスであって、(i)一般式XClHC-CYF2(式中、X及びYの各々は独立して-Cl又は-Fである)の化合物と、(ii)塩基と、(iii)C1-4アルカノールとを含む反応成分をフロー反応器に導入する工程を含み、
a)前記フロー反応器が、115mm2未満の内部断面積を有する1以上の管状フローラインを含み、当該フローラインを通って前記反応成分が反応混合物として流れ、
b)前記ハロゲン化アルコキシエタンが少なくとも前記反応成分の混合時に形成され、そのように形成されたハロゲン化アルコキシエタンが前記フロー反応器から反応器流出液に流出する、プロセス。 - 前記塩基が、前記ハロゲン化アルコキシエタンの形成中に前記アルカノールに可溶な塩を形成するものである、請求項3に記載のプロセス。
- 前記1以上の管状フローラインが、30mm2未満の内部断面積を有する、請求項1~4のいずれか一項に記載のプロセス。
- 前記1以上の管状フローラインが円形の内部断面を有する、請求項1~5のいずれか一項に記載のプロセス。
- 前記管状フローラインが、直径0.1~6mmの円形の内部断面を有する、請求項6に記載のプロセス。
- 前記1以上の管状フローラインが、100mL~1Lの範囲の総内部体積を有する、請求項1~7のいずれか一項に記載のプロセス。
- 前記ハロゲン化アルコキシエタンを含む前記反応器流出液が、少なくとも50mL/分の流量で前記反応器から流出する、請求項1~8のいずれか一項に記載のプロセス。
- 前記反応器流出液が、少なくとも90体積%の前記ハロゲン化アルコキシエタンを含む、請求項1~9のいずれか一項に記載のプロセス。
- 前記フロー反応器が、約5分未満の滞留時間を提供する、請求項1~10のいずれか一項に記載のプロセス。
- 前記反応混合物が、(i)前記C1-4アルカノールと前記塩基との溶液と、(ii)一般式XClHC-CYF2の前記化合物とを混合することによって得られる、請求項1~11のいずれか一項に記載のプロセス。
- 前記混合が、(i)前記C1-4アルカノールと前記塩基との溶液のフローと、(ii)一般式XClHC-CYF2の前記化合物のフローとを1:1~10:1の流量比に従って合わせることによって行われる、請求項1~12のいずれか一項に記載のプロセス。
- 前記塩基が、塩基及びC1-4アルカノールの総重量に対して1重量%~30重量%の量で使用される、請求項1~13のいずれか一項に記載のプロセス。
- 一般式XClHC-CYF2の前記化合物が、Cl2HC-CF3又はFClHC-CF3である、請求項1~14のいずれか一項に記載のプロセス。
- 前記C1-4アルカノールが、メタノール(CH3OH)、エタノール(CH3CH2OH)、1-プロパノール(CH3CH2CH2OH)、2-プロパノール((CH3)2CHOH)、1-ブタノール(CH3CH2CH2CH2OH)、2-ブタノール(CH3CH2CHOHCH3)、2-メチル-1-プロパノール((CH3)2CHCH2OH)、2-メチル-2-プロパノール((CH3)3COH)及びこれらの組合せから選択される、請求項1~15のいずれか一項に記載のプロセス。
- 前記ハロゲン化アルコキシエタンが、Cl2HC-CF2OCH3(メトキシフルラン)又はClFHC-CF2OCH3である、請求項1~16のいずれか一項に記載のプロセス。
- 前記塩基が、アルカリ金属塩基カチオン、アンモニウム塩基カチオン又はホスホニウム塩基カチオンを含む、請求項1~17のいずれか一項に記載のプロセス。
- 前記塩基が、水酸化ナトリウム、水酸化カリウム、ナトリウムメトキシド、カリウムメトキシド、水酸化テトラブチルアンモニウム、水酸化ベンジル(トリメチル)アンモニウム、N-メチル-N,N,N-トリオクチルアンモニウムクロリド(アリコート336)、水酸化テトラエチルアンモニウム、水酸化テトラメチルアンモニウム及び水酸化テトラメチルホスホニウムから選択される、請求項1~18のいずれか一項に記載のプロセス。
- 前記ハロゲン化アルコキシエタンが、前記反応混合物を最大140℃の温度に加熱することによっても形成される、請求項1~19のいずれか一項に記載のプロセス。
- 前記1以上の管状フローラインが、コイル状配置で提供される、請求項1~20のいずれか一項に記載のプロセス。
- 前記反応器流出液又は前記反応器流出液に由来し前記ハロゲン化アルコキシエタンを含む有機相をアミンで処理する精製工程をさらに含む、請求項1~21のいずれか一項に記載のプロセス。
- 以下の順序で:
a)前記反応器流出液と極性溶媒とを混合して、極性相と有機相との相分離を誘導する工程、
b)前記有機相を前記極性相から分離する工程、
c)分離した有機相をアミンで処理する工程、
d)c)で得られた前記有機相を酸溶液で洗浄する工程、
e)d)で得られた前記有機相を乾燥させる工程、および
f)e)で得られた前記有機相を蒸留して前記ハロゲン化アルコキシエタンを含む精製留分を回収する工程、
を含む精製手順をさらに含む、請求項1~21のいずれか一項に記載のプロセス。 - 前記アミンが、エチレンジアミン(1,2-ジアミノエタン)、1,3-ジアミノプロパン、ジエチレントリアミン、ジ-n-プロピルアミン、n-ブチルアミン、エタノールアミン、ピロリジン、2-アミノブタン及びこれらの混合物から選択される、請求項22又は23に記載のプロセス。
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