JP7043489B2 - 窒素及び/又は酸素含有ヒドロフルオロオレフィン、並びにその製造方法及び使用方法 - Google Patents
窒素及び/又は酸素含有ヒドロフルオロオレフィン、並びにその製造方法及び使用方法 Download PDFInfo
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- JP7043489B2 JP7043489B2 JP2019516209A JP2019516209A JP7043489B2 JP 7043489 B2 JP7043489 B2 JP 7043489B2 JP 2019516209 A JP2019516209 A JP 2019516209A JP 2019516209 A JP2019516209 A JP 2019516209A JP 7043489 B2 JP7043489 B2 JP 7043489B2
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- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Description
本開示は、アミン及び/又はエーテル部分を含む不飽和ヒドロフッ素化化合物並びにそれらの製造方法及び使用方法に関する。
地球温暖化係数が低く、同時に高い熱安定性、低毒性、不燃性、良好な溶解力、及び広い動作温度範囲を実現して種々の用途の要件を満たす不活性フッ素化流体が継続して必要とされている。その用途としては、これらに限定されないが、熱伝達、溶媒洗浄、消火剤、並びに電解質溶媒及び添加剤が挙げられる。これらの用途に使用されるフッ素化流体は、典型的には、飽和ヒドロフルオロエーテル、飽和ヒドロフルオロカーボン、及び飽和ペルフルオロカーボンである。本明細書に記載のフッ素化化合物は不飽和であり、アミン及び/又はエーテル基を含む。本明細書に記載の化合物は、上記のフッ素化流体と同じ物理的性質をいくつかもたらすが、概してより短い大気寿命及び低い地球温暖化係数を示し、より許容可能な環境プロファイルを示す。
[式中、
RH 1及びRH 2は独立して、H又はCH3から選択され、RH 1がCH 3であるとき、RH 2はHであり、RH 2がCH3であるとき、RH 1はHであり;
XはO又はNであり、XがOであるとき、nは1であり、Rfは、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~10個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基であり;
XがNであるとき、nは2であり、(i)各Rfは独立して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~8個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基から選択されるか、又は(ii)2つのRfは一緒に結合して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、10個以下の炭素原子を含むペルフルオロ環構造を形成し、その環構造の環は5~7個の原子からなる]の不飽和フッ素化合物を考察する。
(i)フリーラジカル開始剤の存在下で、ペルフルオロアリル化合物を第1のアルコールと反応させて、第2のアルコールを形成することであって、そのペルフルオロアリル化合物はペルフルオロアリルエーテル又はペルフルオロアリルアミンを含み、その第1のアルコールは第一級アルコール又は第二級アルコールであり、第2のアルコールは第二級又は第三級フッ素化アルコールである、第2のアルコールを形成することと、
(ii)第2のアルコールをアシル化して、フッ素化エステルを形成することと、
(iii)不飽和フッ素化化合物を形成するために、そのフッ素化エステルを気相脱ヒドロアセトキシル化することと、を含む。
「a」、「an」、及び「the」という用語は、互換的に使用され、1以上を意味し、
「及び/又は」は、述べられた事例の一方又は両方が起こり得ることを示すために使用され、例えば、A及び/又はBは、(A及びB)と(A又はB)とを含み、
「連結された」は、炭素鎖(直鎖若しくは分枝鎖又は環内)の少なくとも2個の炭素原子に結合して炭素-ヘテロ原子-炭素結合を形成する、炭素以外の原子(例えば、酸素又は窒素)を意味し、
「ペルフルオ」は、C-H結合中の全ての水素原子がC-F結合で置き換えられている基又は化合物を意味し、
「飽和」は、炭素-炭素二重結合又は三重結合を有する化合物を指し、
「不飽和」は、少なくとも1つの炭素-炭素二重結合を有する化合物を指し、
「置換された」(基又は部分に関して)は、少なくとも1個の炭素結合水素原子がハロゲン原子で置き換えられていることを意味する。ハロゲン原子としては、F、Cl、Br、及びIを挙げることができる。
[式中、
RH 1及びRH 2は独立して、H又はCH3から選択され、RH 1がCH3であるとき、RH 2はHであり、RH 2がCH3であるとき、RH 1はHであり;
XはO又はNであり、
(a)XがOであるとき、nは1であり、Rfは、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~10個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基であり;
(b)XがNであるとき、nは2であり、(i)各Rfは独立して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~8個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基から選択されるか、又は(ii)2つのRfは一緒に結合して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、10個以下の炭素原子を含むペルフルオロ環構造を形成し、その環構造の環は5~7個の原子からなる]の不飽和フッ素化化合物である。
[式中、
RH1及びRH2は独立して、H又はCH3から選択され、RH1がCH3であるとき、RH2はHであり、RH2がCH3であるとき、RH1はHであり;
XはO又はNであり、
XがOであるとき、nは1であり、Rfは、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~10個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基であり;
XがNであるとき、nは2であり、(i)各Rfは独立して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~8個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基から選択されるか、又は(ii)2つのRfは一緒に結合して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、10個以下の炭素原子を含むペルフルオロ環構造を形成し、その環構造の環は5~7個の原子からなる]の不飽和フッ素化化合物。
(i)フリーラジカル開始剤の存在下で、ペルフルオロアリル化合物を第1のアルコールと反応させて、第2のアルコールを形成することであって、ペルフルオロアリル化合物はペルフルオロアリルエーテル又はペルフルオロアリルアミンを含み、第1のアルコールは第一級アルコール又は第二級アルコールであり、第2のアルコールは第二級又は第三級フッ素化アルコールである、第2のアルコールを形成することと、
(ii)第2のアルコールをアシル化して、フッ素化エステルを形成することと、
(iii)不飽和フッ素化化合物を形成するために、フッ素化エステルを気相脱ヒドロアセトキシル化することと、を含む、方法。
Claims (12)
- 式(I)
RH 1及びRH 2は独立して、H又はCH3から選択され、RH 1がCH3であるとき、RH 2はHであり、RH 2がCH3であるとき、RH 1はHであり;
XはO又はNであり、
XがOであるとき、nは1であり、Rfは、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~10個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基であり;
XがNであるとき、nは2であり、(i)各Rfは独立して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~8個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基から選択されるか、又は(ii)2つのRfは一緒に結合して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、10個以下の炭素原子を含むペルフルオロ環構造を形成し、前記環構造の環は5~7個の原子からなる]の不飽和フッ素化化合物。 - RH 1及びRH 2がHである、請求項1に記載の不飽和フッ素化化合物。
- XがOであるとき、Rfは1~3個の炭素原子を含む、請求項1又は2に記載の不飽和フッ素化化合物。
- XがNであるとき、前記2つのRfが一緒に結合して、少なくとも1つの連結されたO又はN原子及び7個以下の炭素原子を任意選択的に含む環構造を形成している、請求項1又は2に記載の不飽和フッ素化化合物。
- XがNであり、前記2つのRfが一緒に結合して、(i)連結されたO原子を含む6員環のペルフルオロ環、又は(ii)追加の連結されたN原子を含む6員環のペルフルオロ環を形成している、請求項1又は2に記載の不飽和フッ素化化合物。
- 前記2つのRfが、(i)モルホリン基、(ii)N-ペルフルオロアルキルピペラジン基、又は(iii)ピロリジン基を形成している、請求項1又は2に記載の不飽和フッ素化化合物。
- 不飽和フッ素化化合物は、少なくとも70%のフッ素化度を有する、請求項1~7のいずれか一項に記載の不飽和フッ素化化合物。
- 請求項1~8のいずれか一項に記載の不飽和フッ素化化合物を含む作動流体であって、前記不飽和フッ素化化合物が、前記作動流体中に、前記作動流体の総重量に基づいて少なくとも5重量%の量で存在する、作動流体。
- 請求項1~8のいずれか一項に記載の不飽和フッ素化化合物の使用であって、前記不飽和フッ素化化合物が、(i)洗浄組成物中にあるか、(ii)電解質溶媒又は添加剤であるか、(iii)熱伝達流体であるか、又は(iv)気相はんだ付け流体である、使用。
- デバイスと、前記デバイスに又は前記デバイスから熱を伝達するための機構と、を備えた熱を伝達するための装置であって、前記機構は、請求項1~8のいずれか一項に記載の不飽和フッ素化化合物を含む熱伝達流体を含む、装置。
- 不飽和フッ素化化合物を製造する方法であって、
(i)フリーラジカル開始剤の存在下で、式(II):
XはO又はNであり、
XがOであるとき、nは1であり、R f は、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~10個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基であり;
XがNであるとき、nは2であり、(i)各R f は独立して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、1~8個の炭素原子を含む直鎖又は分枝鎖のペルフルオロアルキル基から選択されるか、又は(ii)2つのR f は一緒に結合して、任意選択的に少なくとも1個の連結されたO又はN原子を含む、10個以下の炭素原子を含むペルフルオロ環構造を形成し、前記環構造の環は5~7個の原子からなる]
のペルフルオロアリル化合物を、式(III):
R H 1 及びR H 2 は独立して、H又はCH 3 から選択され、R H 1 がCH 3 であるとき、R H 2 はHであり、R H 2 がCH 3 であるとき、R H 1 はHである]
で表される第1のアルコールと反応させて、第2のアルコールを形成することであって、前記ペルフルオロアリル化合物はペルフルオロアリルエーテル又はペルフルオロアリルアミンを含み、前記第1のアルコールは第一級アルコール又は第二級アルコールであり、前記第2のアルコールは第二級又は第三級フッ素化アルコールである、第2のアルコールを形成することと、
(ii)前記第2のアルコールをアシル化して、下記式:
のフッ素化エステルを形成することと、
(iii)前記不飽和フッ素化化合物を形成するために、前記フッ素化エステルを気相脱ヒドロアセトキシル化することと、を含む、方法。
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