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1. 发明授权

US08779217B2 Method for preparing fluorine compounds 有权
标题翻译：氟化合物的制备方法
公开(公告)号：US08779217B2
公开(公告)日：2014-07-15
申请号：US13382574
申请日：2010-05-21
申请人： Michel Devic , Nicolas Doucet , Laurent Wendlinger , Geraldine Cavallini , Pierre-Marie Sedat , Karine Avril
发明人： Michel Devic , Nicolas Doucet , Laurent Wendlinger , Geraldine Cavallini , Pierre-Marie Sedat , Karine Avril
IPC分类号： C07C17/25 , C07C17/354
CPC分类号： C07C17/25 , C07C17/354 , C07C21/18 , C07C19/08
摘要： The invention relates to a method for preparing fluoropropenes of formula (I) CF3CF═CHR, where R is a hydrogen or a fluorine atom from at least one compound of formula (Ia) CF3CF═CFR, where R has the same meaning as in formula (I), said method including the following steps: (i) hydrogenating at least one compound of formula (Ia) in an adiabatic reactor in the presence of a catalyst with a superstoichiometric amount of hydrogen so as to produce a hydrofluoropropane; (ii) partially condensing the flow from the adiabatic reactor of step (i) so as to produce a gaseous phase fraction, including unreacted hydrogen and a portion of the formed hydrofluoropropane, which is recirculated to step (i), and a liquid phase fraction including the residue of the hydrofluoropropane; (iii) dehydrofluorinating hydrofluoropropane from the liquid fraction of step (ii) using potassium hydroxide in an aqueous reaction medium contained in an agitated reactor so as to produce the fluoropropene of formula (I); and (iv) purifying the fluoropropene obtained in step (iii).
摘要翻译：本发明涉及一种制备式（I）CF 3 CF = CHR的氟丙烯的方法，其中R是至少一种式（Ia）CF 3 CF = CFR的化合物的氢或氟原子，其中R的定义与式（I），所述方法包括以下步骤：（i）在具有超化学计量的氢的催化剂存在下，在绝热反应器中氢化至少一种式（Ia）化合物以产生氢氟丙烷; （ii）部分地冷凝来自步骤（i）的绝热反应器的流，以便产生气相馏分，包括未反应的氢气和一部分所形成的氢氟丙烷，其循环至步骤（i），以及液相馏分包括氢氟丙烷的残留物; （iii）使用氢氧化钾在搅拌反应器中的含水反应介质中，从步骤（ii）的液体馏分中脱氢氟化氢氟丙烷，以制备式（I）的氟丙烯; 和（iv）纯化步骤（iii）中获得的氟丙烯。

2. 发明申请

US20120136183A1 METHOD FOR PREPARING FLUORINE COMPOUNDS 有权
标题翻译：氟化合物的制备方法
公开(公告)号：US20120136183A1
公开(公告)日：2012-05-31
申请号：US13382574
申请日：2010-05-21
申请人： Michel Devic , Nicolas Doucet , Laurent Wendlinger , Geraldine Cavallini , Pierre-Marie Sedat , Karine Avril
发明人： Michel Devic , Nicolas Doucet , Laurent Wendlinger , Geraldine Cavallini , Pierre-Marie Sedat , Karine Avril
IPC分类号： C07C17/25 , C07C17/383
CPC分类号： C07C17/25 , C07C17/354 , C07C21/18 , C07C19/08
摘要： The invention relates to a method for preparing fluoropropenes of formula (I) CF3CF═CHR, where R is a hydrogen or a fluorine atom from at least one compound of formula (Ia) CF3CF═CFR, where R has the same meaning as in formula (I), said method including the following steps: (i) hydrogenating at least one compound of formula (Ia) in an adiabatic reactor in the presence of a catalyst with a superstoichiometric amount of hydrogen so as to produce a hydrofluoropropane; (ii) partially condensing the flow from the adiabatic reactor of step (i) so as to produce a gaseous phase fraction, including unreacted hydrogen and a portion of the formed hydrofluoropropane, which is recirculated to step (i), and a liquid phase fraction including the residue of the hydrofluoropropane; (iii) dehydrofluorinating hydrofluoropropane from the liquid fraction of step (ii) using potassium hydroxide in an aqueous reaction medium contained in an agitated reactor so as to produce the fluoropropene of formula (I); and (iv) purifying the fluoropropene obtained in step (iii).
摘要翻译：本发明涉及一种制备式（I）CF 3 CF = CHR的氟丙烯的方法，其中R是至少一种式（Ia）CF 3 CF = CFR的化合物的氢或氟原子，其中R的定义与式（I），所述方法包括以下步骤：（i）在具有超化学计量的氢的催化剂存在下，在绝热反应器中氢化至少一种式（Ia）化合物以产生氢氟丙烷; （ii）部分冷凝来自步骤（i）的绝热反应器的流，以便产生气相馏分，包括未反应的氢气和一部分所形成的氢氟丙烷，其循环至步骤（i），以及液相馏分包括氢氟丙烷的残留物; （iii）使用氢氧化钾在搅拌反应器中的含水反应介质中，从步骤（ii）的液体馏分中脱氢氟化氢氟丙烷，以制备式（I）的氟丙烯; 和（iv）纯化步骤（iii）中获得的氟丙烯。

3. 发明授权

US09018429B2 Process for the preparation of fluoroolefin compounds 有权
标题翻译：氟烯烃化合物的制备方法
公开(公告)号：US09018429B2
公开(公告)日：2015-04-28
申请号：US13144239
申请日：2010-01-12
申请人： Pierre-Marie Sedat , Jean-Michel Bossoutrot
发明人： Pierre-Marie Sedat , Jean-Michel Bossoutrot
IPC分类号： C07C17/25 , C07C19/08 , C07C21/18 , C07C17/383
CPC分类号： C07C17/25 , B01J19/0066 , B01J19/18 , B01J2219/00761 , C07C17/383 , C07C21/18
摘要： The subject of the invention is a process for the preparation of fluoroolefin compounds. It relates more particularly to a process for manufacturing a (hydro)fluoroolefin compound comprising (i) bringing at least one compound comprising from three to six carbon atoms, at least two fluorine atoms and at least one hydrogen atom, provided that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, into contact with potassium hydroxide in a stirred reactor, containing an aqueous reaction medium, equipped with at least one inlet for the reactants and with at least one outlet, in order to give the (hydro)fluoroolefin compound, which is separated from the reaction medium in gaseous form, and potassium fluoride, (ii) bringing the potassium fluoride formed in (i) into contact, in an aqueous medium, with calcium hydroxide in order to give potassium hydroxide and to precipitate calcium fluoride, (iii) separation of the calcium fluoride precipitated in step (ii) from the reaction medium and (iv) optionally, the reaction medium is recycled after optional adjustment of the potassium hydroxide concentration to step (i).
摘要翻译：本发明的主题是制备氟烯烃化合物的方法。本发明更具体地涉及一种制备（氢）氟代烯烃化合物的方法，其包括（i）使至少一种包含3至6个碳原子的化合物，至少2个氟原子和至少1个氢原子，条件是至少一个氢原子和一个氟原子位于相邻碳原子上，在搅拌反应器中与氢氧化钾接触，该反应器含有反应物的至少一个入口和至少一个出口，该反应介质装有水性反应介质，以使（氢化）氟化烯烃化合物和氟化钾，（ii）使（i）中形成的氟化钾在水性介质中与氢氧化钙接触以产生氢氧化钾和以沉淀氟化钙，（iii）将步骤（ii）中沉淀的氟化钙与反应介质分离，以及（iv）任选地，将反应介质在任选的将氢氧化钾浓度调节至步骤（i）。

4. 发明申请

US20140378717A1 Method for Preparing Olefin Fluorine Compounds 审中-公开
标题翻译：烯烃氟化合物的制备方法
公开(公告)号：US20140378717A1
公开(公告)日：2014-12-25
申请号：US14324329
申请日：2014-07-07
申请人： Jean-Michel Bossoutrot , Pierre-Marie Sedat
发明人： Jean-Michel Bossoutrot , Pierre-Marie Sedat
IPC分类号： C07C17/25
CPC分类号： C07C17/25 , C01F11/22 , C01P2004/61 , C01P2006/80 , C07C21/18
摘要： The invention relates to a method for preparing olefin fluorine compounds. Specifically, the invention relates to a method for producing a (hydro)fluoroolefin compound, including: (i) in an agitated reactor provided with at least one reactant inlet and at least one outlet, contacting, with potassium hydroxide in an aqueous reaction medium, at least one compound containing three to six carbon atoms, at least two fluorine atoms, and at least one hydrogen atom, with the proviso that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, so as produce the (hydro)fluoroolefin compound, separated in a gaseous state from the reaction medium and from potassium fluoride; (ii) in an aqueous medium, contacting the potassium fluoride formed in step (i) with calcium hydroxide in a second reactor so as to produce potassium. hydroxide and to precipitate calcium tluoride; (iii) separating the calcium fluoride precipitated in step (ii) from the reaction medium; and (iv) optionally recirculating the reaction medium after optionally recirculating the reaction medium after optionally adjusting the concentration of potassium hydroxide in step (i), characterized in that potassium hydroxide, with regard to the reaction medium of step (ii), is between 10 and 35 wt % of the weight of the water/potassium hydroxide mixture of the medium.
摘要翻译：本发明涉及烯烃氟化合物的制备方法。具体地说，本发明涉及一种（氢）氟代烯烃化合物的制备方法，包括：（i）在搅拌反应器中，在反应器中装有至少一个反应物入口和至少一个出口，与氢氧化钾在水性反应介质中接触，至少一种含有三至六个碳原子，至少两个氟原子和至少一个氢原子的化合物，条件是至少一个氢原子和一个氟原子位于相邻碳原子上，以产生（氢）氟代烯烃化合物，其以气态从反应介质和氟化钾分离; （ii）在水性介质中，在步骤（i）中形成的氟化钾与第二反应器中的氢氧化钙接触以产生钾。氢氧化物并沉淀出氟化钙; （iii）将步骤（ii）中沉淀的氟化钙与反应介质分离; 和（iv）任选地在任选地调节步骤（ⅰ）中的氢氧化钾浓度之后任选地再循环反应介质后任选地再循环反应介质，其特征在于相对于步骤（ⅱ）的反应介质，氢氧化钾为10 和35重量％的介质的水/氢氧化钾混合物的重量。

5. 发明授权

US08809601B2 Method for preparing olefin fluorine compounds 有权
标题翻译：制备烯烃氟化合物的方法
公开(公告)号：US08809601B2
公开(公告)日：2014-08-19
申请号：US13384256
申请日：2010-05-19
申请人： Jean-Michel Bossoutrot , Pierre-Marie Sedat
发明人： Jean-Michel Bossoutrot , Pierre-Marie Sedat
IPC分类号： C07C17/25
CPC分类号： C07C17/25 , C01F11/22 , C01P2004/61 , C01P2006/80 , C07C21/18
摘要： The invention relates to a method for preparing olefin fluorine compounds. Specifically, the invention relates to a method for producing a (hydro)fluoroolefin compound, including: (i) in an agitated reactor provided with at least one reactant inlet and at least one outlet, contacting, with potassium hydroxide in an aqueous reaction medium, at least one compound containing three to six carbon atoms, at least two fluorine atoms, and at least one hydrogen atom, with the proviso that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, so as produce the (hydro)fluoroolefin compound, separated in a gaseous state from the reaction medium and from potassium fluoride; (ii) in an aqueous medium, contacting the potassium fluoride formed in step (i) with calcium hydroxide in a second reactor so as to produce potassium hydroxide and to precipitate calcium fluoride; (iii) separating the calcium fluoride precipitated in step (ii) from the reaction medium; and (iv) optionally recirculating the reaction medium after optionally recirculating the reaction medium after optionally adjusting the concentration of potassium hydroxide in step (i), characterized in that potassium hydroxide, with regard to the reaction medium of step (ii), is between 10 and 35 wt % of the weight of the water/potassium hydroxide mixture of the medium.
摘要翻译：本发明涉及烯烃氟化合物的制备方法。具体地说，本发明涉及一种（氢）氟代烯烃化合物的制备方法，包括：（i）在搅拌反应器中，在反应器中装有至少一个反应物入口和至少一个出口，与氢氧化钾在水性反应介质中接触，至少一种含有三至六个碳原子，至少两个氟原子和至少一个氢原子的化合物，条件是至少一个氢原子和一个氟原子位于相邻碳原子上，以产生（氢）氟代烯烃化合物，其以气态从反应介质和氟化钾分离; （ii）在水性介质中，在步骤（i）中形成的氟化钾与第二反应器中的氢氧化钙接触，以产生氢氧化钾并沉淀氟化钙; （iii）将步骤（ii）中沉淀的氟化钙与反应介质分离; 和（iv）任选地在任选地调节步骤（ⅰ）中的氢氧化钾浓度之后任选地再循环反应介质后任选地再循环反应介质，其特征在于相对于步骤（ⅱ）的反应介质，氢氧化钾为10 和35重量％的介质的水/氢氧化钾混合物的重量。

6. 发明申请

US20120116133A1 METHOD FOR PREPARING OLEFIN FLUORINE COMPOUNDS 有权
标题翻译：制备烯烃氟化合物的方法
公开(公告)号：US20120116133A1
公开(公告)日：2012-05-10
申请号：US13384256
申请日：2010-05-19
申请人： Jean-Michel Bossoutrot , Pierre-Marie Sedat
发明人： Jean-Michel Bossoutrot , Pierre-Marie Sedat
IPC分类号： C07C17/25
CPC分类号： C07C17/25 , C01F11/22 , C01P2004/61 , C01P2006/80 , C07C21/18
摘要： The invention relates to a method for preparing olefin fluorine compounds. Specifically, the invention relates to a method for producing a (hydro)fluoroolefin compound, including: (i) in an agitated reactor provided with at least one reactant inlet and at least one outlet, contacting, with potassium hydroxide in an aqueous reaction medium, at least one compound containing three to six carbon atoms, at least two fluorine atoms, and at least one hydrogen atom, with the proviso that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, so as produce the (hydro)fluoroolefin compound, separated in a gaseous state from the reaction medium and from potassium fluoride; (ii) in an aqueous medium, contacvting the potassium fluoride formed in step (i) with calcium hydroxide in a second reactor so as to produce potassium hydroxide and to precipitate calcium fluoride; (iii) separating the calcium fluoride precipitated in step (ii) from the reaction medium; and (iv) optionally recirculating the reaction medium after optionally recirculating the reaction medium after optionally adjusting the concentration of potassium hydroxide in step (i), characterized in that potassium hydroxide, with regard to the reaction medium of step (ii), is between 10 and 35 wt % of the weight of the water/potassium hydroxide mixture of the medium.
摘要翻译：本发明涉及烯烃氟化合物的制备方法。具体地说，本发明涉及一种（氢）氟代烯烃化合物的制备方法，包括：（i）在搅拌反应器中，在反应器中装有至少一个反应物入口和至少一个出口，与氢氧化钾在水性反应介质中接触，至少一种含有三至六个碳原子，至少两个氟原子和至少一个氢原子的化合物，条件是至少一个氢原子和一个氟原子位于相邻碳原子上，以产生（氢）氟代烯烃化合物，其以气态从反应介质和氟化钾分离; （ii）在水性介质中，在第二反应器中将步骤（i）中形成的氟化钾与氢氧化钙接触，以产生氢氧化钾并沉淀氟化钙; （iii）将步骤（ii）中沉淀的氟化钙与反应介质分离; 和（iv）任选地在任选地调节步骤（ⅰ）中的氢氧化钾浓度之后任选地再循环反应介质后任选地再循环反应介质，其特征在于相对于步骤（ⅱ）的反应介质，氢氧化钾为10 和35重量％的介质的水/氢氧化钾混合物的重量。

7. 发明申请

US20120022301A1 Process For The Preparation of Fluoroolefin Compounds 有权
标题翻译：氟烯烃化合物的制备方法
公开(公告)号：US20120022301A1
公开(公告)日：2012-01-26
申请号：US13144239
申请日：2010-01-12
申请人： Pierre-Marie Sedat , Jean-Michel Bossoutrot
发明人： Pierre-Marie Sedat , Jean-Michel Bossoutrot
IPC分类号： C07C17/23
CPC分类号： C07C17/25 , B01J19/0066 , B01J19/18 , B01J2219/00761 , C07C17/383 , C07C21/18
摘要： The subject of the invention is a process for the preparation of fluoroolefin compounds. It relates more particularly to a process for manufacturing a (hydro)fluoroolefin compound comprising (i) bringing at least one compound comprising from three to six carbon atoms, at least two fluorine atoms and at least one hydrogen atom, provided that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, into contact with potassium hydroxide in a stirred reactor, containing an aqueous reaction medium, equipped with at least one inlet for the reactants and with at least one outlet, in order to give the (hydro)fluoroolefin compound, which is separated from the reaction medium in gaseous form, and potassium fluoride, (ii) bringing the potassium fluoride formed in (i) into contact, in an aqueous medium, with calcium hydroxide in order to give potassium hydroxide and to precipitate calcium fluoride, (iii) separation of the calcium fluoride precipitated in step (ii) from the reaction medium and (iv) optionally, the reaction medium is recycled after optional adjustment of the potassium hydroxide concentration to step (i).
摘要翻译：本发明的主题是制备氟烯烃化合物的方法。本发明更具体地涉及一种制备（氢）氟代烯烃化合物的方法，其包括（i）使至少一种包含3至6个碳原子的化合物，至少2个氟原子和至少1个氢原子，条件是至少一个氢原子和一个氟原子位于相邻碳原子上，在搅拌反应器中与氢氧化钾接触，该反应器含有反应物的至少一个入口和至少一个出口，该反应介质装有水性反应介质，以使（氢化）氟化烯烃化合物和氟化钾，（ii）使（i）中形成的氟化钾在水性介质中与氢氧化钙接触以产生氢氧化钾和以沉淀氟化钙，（iii）将步骤（ii）中沉淀的氟化钙与反应介质分离，以及（iv）任选地，将反应介质在任选的将氢氧化钾浓度调节至步骤（i）。

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