JP6137710B2 - 1,1,3−トリクロロ−1−プロペンの合成 - Google Patents
1,1,3−トリクロロ−1−プロペンの合成 Download PDFInfo
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- JP6137710B2 JP6137710B2 JP2015180988A JP2015180988A JP6137710B2 JP 6137710 B2 JP6137710 B2 JP 6137710B2 JP 2015180988 A JP2015180988 A JP 2015180988A JP 2015180988 A JP2015180988 A JP 2015180988A JP 6137710 B2 JP6137710 B2 JP 6137710B2
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- JP
- Japan
- Prior art keywords
- tetrachloropropane
- trichloro
- propene
- mixture
- heated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 title claims description 17
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 26
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 18
- 239000007791 liquid phase Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000008901 benefit Effects 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 238000007033 dehydrochlorination reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002826 coolant Substances 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 239000012159 carrier gas Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HIILBTHBHCLUER-IWQZZHSRSA-N (z)-1,2,3-trichloroprop-1-ene Chemical compound ClC\C(Cl)=C\Cl HIILBTHBHCLUER-IWQZZHSRSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000006115 defluorination reaction Methods 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- -1 digesters Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/04—Chloro-alkenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本出願は、2010年12月1日に提出された米国特許仮出願第61/418、566の優先権の利益を主張する。
実施例1は、気相における鉄触媒による1,1,1,3−テトラクロロプロパンの脱塩化水素反応を例示する。
実施例2は、液相における1,1,1,3−テトラクロロプロパンの脱塩化水素反応を例示する。
実施例3は、液相における1,1,1,3−テトラクロロプロパンの脱塩化水素反応を例示する。
Claims (5)
- 1,1,3−トリクロロ−1−プロペンの製造方法であって、
(a)液相中の1,1,1,3−テトラクロロプロパンを、閉じた容器内で少なくとも175℃に少なくとも1時間加熱し、1,1,3−トリクロロ−1−プロペンを含む生成物の混合物を生成させる工程と、
(b)前記混合物を冷却する工程と、
(c)HClを前記生成物の混合物から分離する工程と、
(d)1,1,3−トリクロロ−1−プロペンを回収する工程と、
を含む方法。 - 1,1,3−トリクロロ−1−プロペンを生じる選択性が少なくとも90%であることを特徴とする請求項1に記載の方法。
- 1,1,3−トリクロロ−1−プロペンを生じる選択性が少なくとも95%であることを特徴とする請求項1に記載の方法。
- 液相中の1,1,1,3−テトラクロロプロパンを、少なくとも200℃に加熱することを特徴とする請求項1に記載の方法。
- 液相中の1,1,1,3−テトラクロロプロパンを、少なくとも175℃に少なくとも2時間加熱することを特徴とする請求項1に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41856610P | 2010-12-01 | 2010-12-01 | |
US61/418,566 | 2010-12-01 |
Related Parent Applications (1)
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---|---|---|---|
JP2013542006A Division JP5838219B2 (ja) | 2010-12-01 | 2011-11-04 | 1,1,3−トリクロロ−1−プロペンの合成 |
Related Child Applications (1)
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JP2017084592A Division JP6791803B2 (ja) | 2010-12-01 | 2017-04-21 | 1,1,3−トリクロロ−1−プロペンの合成 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015221840A JP2015221840A (ja) | 2015-12-10 |
JP6137710B2 true JP6137710B2 (ja) | 2017-05-31 |
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JP2013542006A Active JP5838219B2 (ja) | 2010-12-01 | 2011-11-04 | 1,1,3−トリクロロ−1−プロペンの合成 |
JP2015180988A Active JP6137710B2 (ja) | 2010-12-01 | 2015-09-14 | 1,1,3−トリクロロ−1−プロペンの合成 |
JP2017084592A Active JP6791803B2 (ja) | 2010-12-01 | 2017-04-21 | 1,1,3−トリクロロ−1−プロペンの合成 |
JP2020125546A Active JP7071448B2 (ja) | 2010-12-01 | 2020-07-22 | 1,1,3-トリクロロ-1-プロペンの合成 |
JP2022076667A Pending JP2022093714A (ja) | 2010-12-01 | 2022-05-06 | 1,1,3-トリクロロ-1-プロペンの合成 |
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JP2013542006A Active JP5838219B2 (ja) | 2010-12-01 | 2011-11-04 | 1,1,3−トリクロロ−1−プロペンの合成 |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
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JP2017084592A Active JP6791803B2 (ja) | 2010-12-01 | 2017-04-21 | 1,1,3−トリクロロ−1−プロペンの合成 |
JP2020125546A Active JP7071448B2 (ja) | 2010-12-01 | 2020-07-22 | 1,1,3-トリクロロ-1-プロペンの合成 |
JP2022076667A Pending JP2022093714A (ja) | 2010-12-01 | 2022-05-06 | 1,1,3-トリクロロ-1-プロペンの合成 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8586804B2 (ja) |
EP (3) | EP3699165A1 (ja) |
JP (5) | JP5838219B2 (ja) |
KR (2) | KR20180108857A (ja) |
CN (2) | CN104478652A (ja) |
MX (2) | MX2013006037A (ja) |
WO (1) | WO2012074669A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI709723B (zh) | 2014-02-03 | 2020-11-11 | 日商東普雷股份有限公司 | 冷凍裝置及冷凍裝置的運轉方法 |
Families Citing this family (9)
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US8586804B2 (en) * | 2010-12-01 | 2013-11-19 | E. I. Du Pont De Nemours And Company | Synthesis of 1,1,3-trichloro-1-propene |
US8877991B2 (en) | 2013-02-19 | 2014-11-04 | Honeywell International Inc. | Methods for the dehydrochlorination of 1,1,1,3-tetrachloropropane to 1,1,3-trichloropropene |
US8889927B2 (en) * | 2013-03-12 | 2014-11-18 | Honeywell International Inc. | Method to reduce the formation of high boiling compounds during the dehydrochlorination of 1,1,1,3-tetrachloropropane |
US8889928B2 (en) * | 2013-03-12 | 2014-11-18 | Honeywell International Inc. | Method to improve 1,1,3-trichloropropene and/or 3,3,3-trichloropropene selectivity during the dehydrochlorination of 1,1,1,3-tetrachloropropane |
RU2747936C2 (ru) * | 2014-10-16 | 2021-05-17 | Сполек Про Хемицкоу А Гутни Виробу, Акциова Сполецност | Способ получения хлорированного алкена, композиции, содержащие хлорированный алкен, и их применение |
CZ309310B6 (cs) * | 2014-10-16 | 2022-08-17 | Spolek Pro Chemickou A Hutní Výrobu, Akciová Společnost | Způsob přípravy vysoce čistého 1,1,1,2,3-pentachlorpropanu |
CN106380369B (zh) * | 2016-08-17 | 2019-02-15 | 巨化集团技术中心 | 一种2,3,3,3-四氟丙烯的合成方法 |
US20210198168A1 (en) * | 2018-07-09 | 2021-07-01 | The Chemours Company Fc, Llc | Compositions and methods for an integrated 2,3,3,3-tetrafluoropropene manufacturing process |
CN111643917B (zh) * | 2020-06-15 | 2021-09-17 | 威海新元化工有限公司 | 一种1,1,3-三氯丙烯的连续生产装置及方法 |
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CA1086778A (en) * | 1976-11-18 | 1980-09-30 | Stauffer Chemical Company | Process for the manufacture of 1,1-dihalo-4-methyl-1, 3-pentadienes |
JPS62263134A (ja) * | 1982-04-01 | 1987-11-16 | ヘイロウカ−ボン プロダクツ コ−ポレイシヨン | 1,1,1,3−テトラクロロプロパンの製法 |
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2011
- 2011-10-21 US US13/278,511 patent/US8586804B2/en active Active
- 2011-11-04 WO PCT/US2011/059258 patent/WO2012074669A1/en active Application Filing
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- 2011-11-04 EP EP18177663.4A patent/EP3395790B1/en active Active
- 2011-11-04 CN CN201410667387.6A patent/CN104478652A/zh active Pending
- 2011-11-04 KR KR1020137016927A patent/KR101902807B1/ko active IP Right Grant
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI709723B (zh) | 2014-02-03 | 2020-11-11 | 日商東普雷股份有限公司 | 冷凍裝置及冷凍裝置的運轉方法 |
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CN103221366A (zh) | 2013-07-24 |
KR101902807B1 (ko) | 2018-10-01 |
EP3395790A1 (en) | 2018-10-31 |
WO2012074669A1 (en) | 2012-06-07 |
EP2646402A1 (en) | 2013-10-09 |
MX343642B (es) | 2016-11-15 |
JP2015221840A (ja) | 2015-12-10 |
JP7071448B2 (ja) | 2022-05-19 |
US8586804B2 (en) | 2013-11-19 |
CN103221366B (zh) | 2015-05-20 |
US20120142980A1 (en) | 2012-06-07 |
KR20130136491A (ko) | 2013-12-12 |
EP3395790B1 (en) | 2020-04-08 |
EP3699165A1 (en) | 2020-08-26 |
EP2646402B1 (en) | 2019-01-09 |
MX2013006037A (es) | 2013-08-01 |
KR20180108857A (ko) | 2018-10-04 |
JP2014502960A (ja) | 2014-02-06 |
CN104478652A (zh) | 2015-04-01 |
JP2020169225A (ja) | 2020-10-15 |
JP2017125067A (ja) | 2017-07-20 |
JP5838219B2 (ja) | 2016-01-06 |
JP6791803B2 (ja) | 2020-11-25 |
JP2022093714A (ja) | 2022-06-23 |
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