JP2014527458A - ハロアルカン化合物の製造において用いた鉄触媒を捕捉及び再循環する方法 - Google Patents
ハロアルカン化合物の製造において用いた鉄触媒を捕捉及び再循環する方法 Download PDFInfo
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- JP2014527458A JP2014527458A JP2014513673A JP2014513673A JP2014527458A JP 2014527458 A JP2014527458 A JP 2014527458A JP 2014513673 A JP2014513673 A JP 2014513673A JP 2014513673 A JP2014513673 A JP 2014513673A JP 2014527458 A JP2014527458 A JP 2014527458A
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- iron
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 229910052742 iron Inorganic materials 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000003054 catalyst Substances 0.000 title claims abstract description 24
- -1 haloalkane compounds Chemical class 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 238000004064 recycling Methods 0.000 title abstract description 3
- 230000008569 process Effects 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims abstract description 11
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 13
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 4
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 3
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002245 particle Substances 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000010924 continuous production Methods 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000013522 chelant Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/08—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles
- B01J8/10—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles moved by stirrers or by rotary drums or rotary receptacles or endless belts
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/20—Stationary reactors having moving elements inside in the form of helices, e.g. screw reactors
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/005—Separating solid material from the gas/liquid stream
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/005—Separating solid material from the gas/liquid stream
- B01J8/0075—Separating solid material from the gas/liquid stream by electrostatic precipitation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C1/00—Magnetic separation
- B03C1/02—Magnetic separation acting directly on the substance being separated
- B03C1/025—High gradient magnetic separators
- B03C1/031—Component parts; Auxiliary operations
- B03C1/033—Component parts; Auxiliary operations characterised by the magnetic circuit
- B03C1/0335—Component parts; Auxiliary operations characterised by the magnetic circuit using coils
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C5/00—Separating dispersed particles from liquids by electrostatic effect
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only 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
- C07C21/06—Vinyl chloride
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/745—Iron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
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- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C2201/00—Details of magnetic or electrostatic separation
- B03C2201/18—Magnetic separation whereby the particles are suspended in a liquid
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Y02P20/584—Recycling of catalysts
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
(a)CCl4及びVCMを、鉄粉及びTBPを含む触媒と共に反応器中に供給してHCC−240faを形成し;
(b)電圧を加えた電磁気分離ユニット(EMSU)を用いることによって、HCC−240fa反応器流出流から鉄粒子を取り出し;そして
(c)EMSUを電圧解除し、鉄粒子を再循環して、鉄粒子を工程(a)において再使用するために反応器に戻す;
工程を含む、1,1,1,3,3−ペンタクロロプロパンの製造中において鉄触媒を捕捉して再循環する方法である。
(1)HCC−250は、CCl4及びエチレンから次の反応:
(2)HCC−360は、CCl4及び2−クロロプロペンから次の反応:
本発明は以下の態様を含む。
[1]
電磁気分離ユニット(EMSU)を用いることによって、鉄触媒及び共触媒として1種類以上のトリアルキルホスフェート化合物を用いることによる四塩化炭素及びアルケンからのハロアルカン化合物の製造中に用いた鉄触媒を捕捉して再循環する方法。
[2]
アルケンが、塩化ビニル、エチレン、及び2−クロロプロペンからなる群から選択される、[1]に記載の方法。
[3]
ハロアルカン化合物が、HCC−240fa、HCC−250、及びHCC−360からなる群から選択される、[1]に記載の方法。
[4]
鉄触媒が、鉄粉、鉄球、鉄線、鉄屑、及びこれらの混合物からなる群から選択される形態を有する、[1]に記載の方法。
[5]
共触媒が、トリブチルホスフェート、トリメチルホスフェート、トリエチルホスフェート、トリプロピルホスフェート、及びこれらの2以上の混合物からなる群から選択される、[1]に記載の方法。
[6]
連続運転として行う、[1]に記載の方法。
[7]
バッチ運転として行う、[1]に記載の方法。
[8]
2以上の電圧を加えた電磁気分離ユニットを用いる、[1]に記載の方法。
[9]
2以上のEMSUをタンデムに設置して並行して運転する、[8]に記載の方法。
Claims (9)
- 電磁気分離ユニット(EMSU)を用いることによって、鉄触媒及び共触媒として1種類以上のトリアルキルホスフェート化合物を用いることによる四塩化炭素及びアルケンからのハロアルカン化合物の製造中に用いた鉄触媒を捕捉して再循環する方法。
- アルケンが、塩化ビニル、エチレン、及び2−クロロプロペンからなる群から選択される、請求項1に記載の方法。
- ハロアルカン化合物が、HCC−240fa、HCC−250、及びHCC−360からなる群から選択される、請求項1に記載の方法。
- 鉄触媒が、鉄粉、鉄球、鉄線、鉄屑、及びこれらの混合物からなる群から選択される形態を有する、請求項1に記載の方法。
- 共触媒が、トリブチルホスフェート、トリメチルホスフェート、トリエチルホスフェート、トリプロピルホスフェート、及びこれらの2以上の混合物からなる群から選択される、請求項1に記載の方法。
- 連続運転として行う、請求項1に記載の方法。
- バッチ運転として行う、請求項1に記載の方法。
- 2以上の電圧を加えた電磁気分離ユニットを用いる、請求項1に記載の方法。
- 2以上のEMSUをタンデムに設置して並行して運転する、請求項8に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161492907P | 2011-06-03 | 2011-06-03 | |
US61/492,907 | 2011-06-03 | ||
US13/471,601 | 2012-05-15 | ||
US13/471,601 US10112166B2 (en) | 2011-06-03 | 2012-05-15 | Method for capturing and recycling iron catalyst used in the production of haloalkane compounds |
PCT/US2012/040070 WO2012166836A2 (en) | 2011-06-03 | 2012-05-31 | Method for capturing and recycling iron catalyst used in the production of haloalkane compounds |
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JP2017052870A Division JP2017127870A (ja) | 2011-06-03 | 2017-03-17 | ハロアルカン化合物の製造において用いた鉄触媒を捕捉及び再循環する方法 |
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JP2014527458A true JP2014527458A (ja) | 2014-10-16 |
JP6152097B2 JP6152097B2 (ja) | 2017-06-21 |
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JP2017052870A Pending JP2017127870A (ja) | 2011-06-03 | 2017-03-17 | ハロアルカン化合物の製造において用いた鉄触媒を捕捉及び再循環する方法 |
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US (1) | US10112166B2 (ja) |
EP (1) | EP2714270B1 (ja) |
JP (2) | JP6152097B2 (ja) |
KR (1) | KR102002932B1 (ja) |
CN (2) | CN109127146A (ja) |
CA (1) | CA2836077A1 (ja) |
ES (1) | ES2674283T3 (ja) |
MX (1) | MX362213B (ja) |
RU (1) | RU2606633C2 (ja) |
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US8859829B2 (en) * | 2013-03-14 | 2014-10-14 | Honeywell International Inc. | Stabilizer and inhibitor for chloropropenes, such as tetrachloropropene 1,1,2,3-tetrachloropropene (1230xa), used in the manufacture of 2,3,3,3-tetrafluoropropene (1234yf) |
US9090531B2 (en) * | 2013-03-14 | 2015-07-28 | Honeywell International Inc. | Method for mitigating HCL generation during 1,1,2,3-tetrachloropropene purification |
US10717662B2 (en) * | 2018-02-07 | 2020-07-21 | Honeywell International Inc. | Process for the removal of iron and phosphate ions from a chlorinated hydrocarbon waste stream |
EP3774703B1 (en) * | 2018-04-03 | 2022-04-27 | Blue Cube IP LLC | Method for recycling catalyst in the production of chlorinated alkanes |
CN111659322A (zh) * | 2019-03-06 | 2020-09-15 | 浙江佳汇新材料有限公司 | 一种制备1,1,1,3-四氯丙烷的装置及工艺 |
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CA2836077A1 (en) | 2012-12-06 |
JP6152097B2 (ja) | 2017-06-21 |
US20120305454A1 (en) | 2012-12-06 |
ES2674283T3 (es) | 2018-06-28 |
RU2606633C2 (ru) | 2017-01-10 |
JP2017127870A (ja) | 2017-07-27 |
CN103648640A (zh) | 2014-03-19 |
MX2013013379A (es) | 2013-12-02 |
RU2013156262A (ru) | 2015-07-20 |
KR20140037151A (ko) | 2014-03-26 |
EP2714270B1 (en) | 2018-03-21 |
EP2714270A4 (en) | 2015-03-11 |
WO2012166836A2 (en) | 2012-12-06 |
WO2012166836A3 (en) | 2013-03-21 |
KR102002932B1 (ko) | 2019-07-23 |
US10112166B2 (en) | 2018-10-30 |
MX362213B (es) | 2019-01-09 |
EP2714270A2 (en) | 2014-04-09 |
CN109127146A (zh) | 2019-01-04 |
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