• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention relates to a azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane characterized in that said composition has a point of boiling above 40 ° C.
    公开号:FR3077572A1
    申请号:FR1850925
    申请日:2018-02-05
    公开日:2019-08-09
    发明作者:Dominique Deur-Bert；Laurent Wendlinger；Beatrice Berger
    申请人:Arkema France SA；
    IPC主号:
    专利说明:

    Ternary azeotropic or quasi-azeotropic composition comprising HF, 2,3,3,3tetrafluoropropene and 1,1,1,2,2-pentafluoropropane
    Technical field of the invention
    The present invention relates to a composition comprising hydrogen fluoride,
    2.3.3.3- tetrafluoropropene and 1,1,1,2,2-pentafluoropropene. In particular, the present invention relates to an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropene
    Technological background of the invention
    Hydrofluorocarbons (HFCs) and in particular hydrofluoroolefins, such as
    2.3.3.3- tetrafluoro-l-propene (HFO 1234yf) are compounds known for their properties as coolants and heat transfer fluids, fire extinguishers, propellants, foaming agents, swelling agents, gaseous dielectrics, polymerization medium or monomer, carrier fluids, agents for abrasives, drying agents and fluids for power generation units. Unlike CFCs and HCFCs, which are potentially dangerous for the ozone layer, HFOs do not contain chlorine and therefore do not pose a problem for the ozone layer. Several processes are known for manufacturing 1234yf. For example, WO 2011/010025 describes the process for preparing 2,3,3,3-tetrafluoropropene from hexafluoropropylene. Also known from WO 2013/088195 is the preparation of 2,3,3,3-tetrafluoropropene from 1,1,1,2,3-pentachloropropane. In addition to the actual reaction stages, the processes for preparing 2,3,3,3-tetrafluoropropene known from the prior art use one or more purification stages generally including one or more distillations.
    The operation of a distillation column can be disturbed by the formation of azeotropic compositions during the implementation thereof. This can cause a decrease in efficiency in the separation of the different compounds. This can also induce a bad design of the distillation column with important repercussions on the overall efficiency of the process on an industrial scale. The existence of azeotropes between hydrogen fluoride and 2,3,3,3-tetrafluoropropene is known from US 7,476,771. In addition, the existence of azeotropes between hydrogen fluoride and 1,1,1,2,2-pentafluoropropane, a by-product observed in the processes for preparing 2,3,3,3-tetrafluoropropene is also known from WO 2008/054781.
    The identification of new azeotropic compositions is essential to provide an effective separation or purification process.
    Summary of the invention
    According to a first aspect, the present invention relates to an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane, characterized in that said composition has a boiling point higher than 40 ° C, advantageously higher than 45 ° C, preferably higher than 50 ° C.
    According to a preferred embodiment, said composition is obtained for a pressure greater than 11 bara, advantageously greater than 13 bara, preferably greater than 15 bara.
    According to a preferred embodiment, said composition has a boiling point between 40 ° C and 100 ° C at a pressure between 11 and 30 bara; advantageously a boiling point between 45 ° C and 100 ° C at a pressure between 13 and 30 bara.
    According to a preferred embodiment, the hydrogen fluoride content is from 10 to 70 mol% based on the molar composition of said composition.
    According to a preferred embodiment, the content of 2,3,3,3-tetrafluoropropene is from 10 to 90 mol% based on the molar composition of said composition.
    According to a preferred embodiment, the content of 1,1,1,2,2-pentafluoropropane is from 1 to 50 mol% based on the molar composition of said composition.
    According to a preferred embodiment, the boiling point of said azeotropic or quasi-azeotropic composition is between 45 ° C and 65 ° C at a pressure between 13 and 20 bara, advantageously between 50 ° C and 65 ° C at a pressure between 15 and 20 bara.
    According to a preferred embodiment, said azeotropic or quasiazeotropic composition consists of hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2pentafluoropropane.
    According to a preferred embodiment, the azeotropic or quasiazeotropic composition comprises 31 mol.% Of hydrogen fluoride, 66 mol.% Of 2,3,3,3tetrafluoropropene and 3 mol.% Of 1,1,1,2,2 -pentafluoropropane, and has a boiling point of 60 ° C at a pressure of 18 bara.
    According to a second aspect, the present invention relates to a process for separating a composition comprising hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2pentafluoropropane, characterized in that it comprises the stages of:
    i) supply of a composition comprising hydrogen fluoride, 2,3,3,3tetrafluoropropene and 1,1,1,2,2-pentafluoropropane;
    ii) distillation of said composition supplied in step i) at a temperature at the bottom of the distillation column of less than 45 ° C, preferably less than 40 ° C, to form and recover a first stream, advantageously at the top of the column of distillation, including
    2,3,3,3-tetrafluoropropene and hydrogen fluoride and a second stream, advantageously at the bottom of the distillation column, comprising 1,1,1,2,2-pentafluoropropane and hydrogen fluoride.
    The implementation of the method according to the second aspect of the present invention makes it possible to avoid the formation of the ternary azeotropic composition according to the present invention, and thus to effectively separate the 2,3,3,3-tetrafluoropropene from the 1.1, 1,2,2-pentafluoropropane by distillation.
    Detailed description of the invention
    According to a first aspect of the present invention, an azeotropic or quasi-azeotropic composition is provided. Preferably, said azeotropic or quasiazeotropic composition comprises hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2pentafluoropropane.
    The applicant has surprisingly identified the formation of a ternary azeotropic composition HF / HFO-1234yf / HFC-245cb under particular temperature conditions. The formation of this ternary composition during stages of distillation of a reaction flow can disturb their proper functioning and prevent an effective separation between 2,3,3,3-tetrafluoropropene and 1,1,1,2,2 -pentafluoropropane when such separation is sought.
    Preferably, said azeotropic or quasi-azeotropic composition comprises hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane and has a boiling point above 40 ° C. . In particular, said azeotropic or quasiazeotropic composition has a boiling point greater than 41 ° C or greater than 42 ° C or greater than 43 ° C or greater than 44 ° C or greater than 45 ° C or greater than 46 ° C or greater than 47 ° C or greater than 48 ° C or greater than 49 ° C or greater than 50 ° C.
    In particular, said azeotropic or quasi-azeotropic composition has a boiling point of less than 100 ° C, advantageously less than 90 ° C, preferably less than 80 ° C, in particular less than 70 ° C. Thus, said azeotropic or quasiazeotropic composition has a boiling point below 100 ° C or below 99 ° C or below 98 ° C or below 97 ° C or below 96 ° C or below 95 ° C or below at 94 ° C or below 93 ° C or below 92 ° C or below 91 ° C or below 90 ° C or below 89 ° C or below 88 ° C or below 87 ° C or below 86 ° C or below 85 ° C or below 84 ° C or below 83 ° C or below 82 ° C or below 81 ° C or below 80 ° C or below 79 ° C or below 78 ° C or n lower than 77 ° C or lower than 76 ° C or lower than 75 ° C or lower than 74 ° C or lower than 73 ° C or lower than 72 ° C or lower than 71 ° C or lower than 70 ° C.
    More preferably, said azeotropic or quasi-azeotropic composition has a boiling point below 69 ° C or below 68 ° C or below 67 ° C or below 66 ° C or below 65 ° C.
    Preferably, said azeotropic or quasi-azeotropic composition has a boiling point greater than 40 ° C or greater than 41 ° C or greater than 42 ° C or greater than 43 ° C or greater than 44 ° C or greater than 45 ° C or greater than 46 ° C or greater than 47 ° C or greater than 48 ° C or greater than 49 ° C or greater than 50 ° C; and less than 100 ° C, advantageously less than 90 ° C, preferably less than 80 ° C, in particular less than 70 ° C.
    In particular, said azeotropic or quasi-azeotropic composition has a boiling point greater than 40 ° C or greater than 41 ° C or greater than 42 ° C or greater than 43 ° C or greater than 44 ° C or greater than 45 ° C or greater than 46 ° C or greater than 47 ° C or greater than 48 ° C or greater than 49 ° C or greater than 50 ° C; and below 100 ° C or below 99 ° C or below 98 ° C or below 97 ° C or below 96 ° C or below 95 ° C or below 94 ° C or below 93 ° C or below at 92 ° C or below 91 ° C or below 90 ° C or below 89 ° C or below 88 ° C or below 87 ° C or below 86 ° C or below 85 ° C or below 84 ° C or below 83 ° C or below 82 ° C or below 81 ° C or below 80 ° C or below 79 ° C or n below 78 ° C or below 77 ° C or below 76 ° C or lower than 75 ° C or lower than 74 ° C or lower than 73 ° C or lower than 72 ° C or lower than 71 ° C or lower than 70 ° C.
    More particularly, said azeotropic or quasi-azeotropic composition has a boiling point greater than 40 ° C or greater than 41 ° C or greater than 42 ° C or greater than 43 ° C or greater than 44 ° C or greater than 45 ° C or greater than 46 ° C or greater than 47 ° C or greater than 48 ° C or greater than 49 ° C or greater than 50 ° C; and lower than 69 ° C or lower than 68 ° C or lower than 67 ° C or lower than 66 ° C or lower than 65 ° C.
    In particular, said azeotropic or quasi-azeotropic composition has a boiling point of between 45 ° C and 65 ° C. More particularly, said azeotropic or quasi-azeotropic composition has a boiling point of between 50 ° C. and 65 ° C.
    According to a preferred embodiment, the azeotropic or quasiazeotropic composition is obtained for a pressure between 11 and 30 bara, advantageously between 11 and 25 bara, preferably between 11 and 24 bara, more preferably between 12 and 23 bara, in particular between 12 and 22 bara, more particularly between 12 and 21 bara, preferably between 12 and 20 bara, more preferably between 13 and 20 bara.
    Preferably, said azeotropic or quasi-azeotropic composition comprises hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane and has a boiling point of between 40 ° C. and 100 ° C at a pressure between 11 and 30 bara, advantageously a boiling point between 45 ° C and 90 ° C at a pressure between 13 and 28 bara, preferably a boiling point between 45 ° C and 80 ° C at a pressure between 13 and 25 bara, more preferably a boiling point between 45 ° C and 70 ° C at a pressure between 13 and 21 bara, in particular a boiling point between 45 ° C and 65 ° C at a pressure between 13 and 20 bara, more particularly a boiling point between 50 ° C and 65 ° C at a pressure between 15 and 20 bara.
    According to a preferred embodiment, the hydrogen fluoride content is from 10 to 70 mol% based on the molar composition of said composition, preferably from 15 to 65 mol%, in particular from 20 to 60 mol% , more particularly from 25 to 55 mol% based on the molar composition of said composition.
    According to a preferred embodiment, the content of 2,3,3,3-tetrafluoropropene is from 10 to 90% by mole based on molar composition of said composition, preferably from 15 to 85% by mole, in particular from 20 at 80% by mole, more particularly from 20 to 75% by mole, preferably from 20 to 70% by mole based on the molar composition of said composition.
    According to a preferred embodiment, the content of 1,1,1,2,2-pentafluoropropane is from 1 to 50% by mole based on the molar composition of said composition, preferably from 1 to 45% by mole, in particular from 1 to 40% by mole, more particularly from 2 to 35% by mole, preferably from 2 to 30% by mole based on the molar composition of said composition.
    Preferably, said azeotropic or quasi-azeotropic composition comprises from 10 to 70 mol% of hydrogen fluoride, from 10 to 90 mol% of 2,3,3,3-tetrafluoropropene and from 1 to 50 mol% of 1,1,1,2,2-pentafluoropropane based on the molar composition of said composition.
    In particular, said azeotropic or quasi-azeotropic composition comprises from 10 to 70% by mole, preferably from 15 to 65% by mole, in particular from 20 to 60% by mole, more particularly from 25 to 55% by mole of fluoride hydrogen; from 10 to 90% by mole, preferably from 15 to 85% by mole, in particular from 20 to 80% by mole, more particularly from 20 to 75% by mole, in a preferred manner from 20 to 70% by mole of 2 , 3,3,3-tetrafluoropropene; and from 1 to 50% by mole, preferably from 1 to 45% by mole, in particular from 1 to 40% by mole, more particularly from 2 to 35% by mole, preferably from 2 to 30% by mole of 1,1,1,2,2-pentafluoropropane based on the molar composition of said composition.
    More particularly, said composition consists of:
    • from 10 to 70% by mole, preferably from 15 to 65% by mole, in particular from 20 to 60% by mole, more particularly from 25 to 55% by mole of hydrogen fluoride;
    From 10 to 90% by mole, preferably from 15 to 85% by mole, in particular from 20 to 80% by mole, more particularly from 20 to 75% by mole, preferably from 20 to 70% by mole of 2,3,3,3-tetrafluoropropene; and • from 1 to 50% by mole, preferably from 1 to 45% by mole, in particular from 1 to 40% by mole, more particularly from 2 to 35% by mole, preferably from 2 to 30% by mole 1,1,1,2,2-pentafluoropropane based on the molar composition of said composition.
    Thus, in a particularly preferred embodiment, the present invention provides an azeotropic or quasi-azeotropic composition comprising:
    • from 10 to 70% by mole, preferably from 15 to 65% by mole, in particular from 20 to 60% by mole, more particularly from 25 to 55% by mole of hydrogen fluoride;
    From 10 to 90% by mole, preferably from 15 to 85% by mole, in particular from 20 to 80% by mole, more particularly from 20 to 75% by mole, preferably from 20 to 70% by mole of 2,3,3,3-tetrafluoropropene; and • from 1 to 50% by mole, preferably from 1 to 45% by mole, in particular from 1 to 40% by mole, more particularly from 2 to 35% by mole, preferably from 2 to 30% by mole 1,1,1,2,2-pentafluoropropane based on the molar composition of said composition; said composition having a boiling point between 40 ° C and 100 ° C at a pressure between 11 and 30 bara, advantageously a boiling point between 45 ° C and 90 ° C at a pressure between 13 and bara, preferably a boiling point between 45 ° C and 80 ° C at a pressure between 13 and 25 bara, more preferably a boiling point between 45 ° C and 70 ° C at a pressure between 13 and 21 bara, in particular a boiling point between 45 ° C and 65 ° C at a pressure between 13 and 20 bara, more particularly a boiling point between 50 ° C and 65 ° C at a pressure between 15 and 20 bara.
    In particular, the present invention provides an azeotropic or quasiazeotropic composition consisting of:
    • from 10 to 70% by mole, preferably from 15 to 65% by mole, in particular from 20 to 60% by mole, more particularly from 25 to 55% by mole of hydrogen fluoride;
    From 10 to 90% by mole, preferably from 15 to 85% by mole, in particular from 20 to 80% by mole, more particularly from 20 to 75% by mole, preferably from 20 to 70% by mole of 2,3,3,3-tetrafluoropropene; and • from 1 to 50% by mole, preferably from 1 to 45% by mole, in particular from 1 to 40% by mole, more particularly from 2 to 35% by mole, preferably from 2 to 30% by mole 1,1,1,2,2-pentafluoropropane based on the molar composition of said composition; said composition having a boiling point between 45 ° C and 65 ° C at a pressure between 13 and 20 bara, advantageously a boiling point between 50 ° C and 65 ° C at a pressure between 15 and 20 bara.
    Preferably, the azeotropic composition preferably comprises 31 mol%. hydrogen fluoride, 66% mol. 2,3,3,3-tetrafluoropropene and 3 mol%. 1,1,1,2,2pentafluoropropane, and has a boiling point of 60 ° C at a pressure of 18 bara.
    According to a second aspect, a method for separating a composition comprising hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane is provided. Said method comprises the steps of:
    i) supply of a composition comprising hydrogen fluoride, 2,3,3,3tetrafluoropropene and 1,1,1,2,2-pentafluoropropane;
    ii) distillation of said composition supplied in step i) at a temperature at the bottom of the distillation column of less than 45 ° C, preferably less than 40 ° C, to form and recover a first stream, advantageously at the top of the column of distillation, including
    2,3,3,3-tetrafluoropropene and hydrogen fluoride and a second stream, advantageously at the bottom of the distillation column, comprising 1,1,1,2,2-pentafluoropropane and hydrogen fluoride.
    Advantageously, said first stream comprises at least 90%, preferably at least 95%, more preferably at least 98%, in particular at least 99% of the 2,3,3,3tetrafluoropropene present in said composition of step i).
    Advantageously, said first stream comprises less than 40%, preferably less than 30%, more preferably less than 20%, in particular less than 15%, more particularly less than 10%, preferably less than 5% of the 1.1 , 1,2,2pentafluoropropane present in said composition of step i).
    Example
    At 60 ° C. and 18 bara, the composition comprising 31 mol% of HF, 66 mol% of HFO1234yf and 3 mol% of HFC-245cb was identified as azeotropic.
    权利要求:
    Claims (10)
    [1" id="c-fr-0001]
    claims
    1. Azeotropic or quasi-azeotropic composition comprising hydrogen fluoride,
    [2" id="c-fr-0002]
    2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane, characterized in that said composition has a boiling point higher than 40 ° C, advantageously higher than 45 ° C, preferably higher at 50 ° C.
    2. Composition according to claim 1 characterized in that it is obtained for a pressure greater than 11 bara, advantageously greater than 13 bara, preferably greater than 15 bara.
    [3" id="c-fr-0003]
    3. Composition according to any one of the preceding claims, characterized in that it has a boiling point between 40 ° C and 100 ° C at a pressure between 11 and 30 bara; advantageously a boiling point between 45 ° C and 100 ° C at a pressure between 13 and 30 bara.
    [4" id="c-fr-0004]
    4. Composition according to any one of the preceding claims, characterized in that the hydrogen fluoride content is from 10 to 70% by mole based on the molar composition of said composition.
    [5" id="c-fr-0005]
    5. Composition according to any one of the preceding claims, characterized in that the content of 2,3,3,3-tetrafluoropropene is from 10 to 90% by mole based on the molar composition of said composition.
    [6" id="c-fr-0006]
    6. Composition according to any one of the preceding claims, characterized in that the content of 1,1,1,2,2-pentafluoropropane is from 1 to 50% by mole based on the molar composition of said composition.
    [7" id="c-fr-0007]
    7. Composition according to any one of the preceding claims, characterized in that the boiling point of said azeotropic or quasi-azeotropic composition is between 45 ° C and 65 ° C at a pressure between 13 and 20 bara, advantageously between 50 ° C and 65 ° C at a pressure between 15 and 20 bara.
    [8" id="c-fr-0008]
    8. Composition according to any one of the preceding claims, characterized in that it comprises 31% mol. hydrogen fluoride, 66% mol. 2,3,3,3-tetrafluoropropene and 3 mol%. 1,1,1,2,2-pentafluoropropane, and has a boiling point of 60 ° C at a pressure of 18 bara.
    [9" id="c-fr-0009]
    9. Composition according to any one of the preceding claims, characterized in that it consists of hydrogen fluoride, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2pentafluoropropane.
    [10" id="c-fr-0010]
    10. Method for separating a composition comprising hydrogen fluoride, 2,3,3,3tetrafluoropropene and 1,1,1,2,2-pentafluoropropane characterized in that it comprises the steps of:
    i) supply of a composition comprising hydrogen fluoride, 2,3,3,3tetrafluoropropene and 1,1,1,2,2-pentafluoropropane;
    ii) distillation of said composition supplied in step i) at a temperature at the bottom of the distillation column of less than 45 ° C, preferably less than 40 ° C, to form and recover a first stream, advantageously at the top of the column of distillation, including
    2,3,3,3-tetrafluoropropene and hydrogen fluoride and a second stream, advantageously at the bottom of the distillation column, comprising 1,1,1,2,2-pentafluoropropane and hydrogen fluoride.
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    法律状态:
    2019-01-11| PLFP| Fee payment|Year of fee payment: 2 |
    2019-08-09| PLSC| Publication of the preliminary search report|Effective date: 20190809 |
    2020-01-13| PLFP| Fee payment|Year of fee payment: 3 |
    2021-01-13| PLFP| Fee payment|Year of fee payment: 4 |
    2022-01-18| PLFP| Fee payment|Year of fee payment: 5 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1850925A|FR3077572B1|2018-02-05|2018-02-05|TERNARY AZEOTROPIC OR QUASI-AZEOTROPIC COMPOSITION COMPRISING HF, 2,3,3,3-TETRAFLUOROPROPENE AND 1,1,1,2,2, -PENTAFLUOROPROPANE.|
    FR1850925|2018-02-05|FR1850925A| FR3077572B1|2018-02-05|2018-02-05|TERNARY AZEOTROPIC OR QUASI-AZEOTROPIC COMPOSITION COMPRISING HF, 2,3,3,3-TETRAFLUOROPROPENE AND 1,1,1,2,2, -PENTAFLUOROPROPANE.|
    PCT/FR2019/050229| WO2019150052A1|2018-02-05|2019-02-01|Ternary azeotropic or quasi-azeotropic composition comprising hf, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane|
    US16/965,638| US11001546B2|2018-02-05|2019-02-01|Ternary azeotropic or quasi-azeotropic composition comprising HF, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane|
    EP19707442.0A| EP3749629A1|2018-02-05|2019-02-01|Ternary azeotropic or quasi-azeotropic composition comprising hf, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane|
    CN201980011592.8A| CN111683920A|2018-02-05|2019-02-01|Ternary azeotropic or quasi-azeotropic compositions comprising HF, 2,3,3, 3-tetrafluoropropene and 1,1,1,2, 2-pentafluoropropane|
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