JP7017555B2 - 塩素化プロパンの製造、調整、及び精製方法 - Google Patents
塩素化プロパンの製造、調整、及び精製方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims description 25
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims description 22
- 238000007670 refining Methods 0.000 title description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 60
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 52
- 239000007788 liquid Substances 0.000 claims description 52
- 239000002002 slurry Substances 0.000 claims description 38
- 239000003054 catalyst Substances 0.000 claims description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 25
- 239000005977 Ethylene Substances 0.000 claims description 25
- 150000001336 alkenes Chemical class 0.000 claims description 22
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000012018 catalyst precursor Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000011049 filling Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 description 18
- 238000004821 distillation Methods 0.000 description 17
- 229910052742 iron Inorganic materials 0.000 description 17
- 230000003068 static effect Effects 0.000 description 11
- 238000002156 mixing Methods 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 8
- 239000003446 ligand Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 239000003426 co-catalyst Substances 0.000 description 4
- 239000000047 product Substances 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
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 description 2
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 description 1
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- -1 phosphate ester Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
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- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
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- 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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- B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
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Description
上で示唆したように、本発明の方法は、一般に四塩化炭素をオレフィンと反応させて塩素化炭化水素を調製することに関する。これらの反応は、一般に当該分野で知られており、従って米国特許第6,313,360号ならびに米国公開第2004/0225166号および2009/0216055号は引用により本明細書に組み込まれる。本発明の実施形態の実施は、反応物として用いられるオレフィンにより必ずしも限定されないが、これらの反応で共通して用いられるオレフィン類にはエチレンと塩化ビニルが含まれる。当業者には自明であるが、エチレンは気体状オレフィンであり、従って、本発明の実施形態はエチレンを反応物として用いる場合に明白な利点を提供する場合がある。他の実施形態は、塩化ビニルを反応物として用いる場合に特に利点がある場合がある。いずれにせよ、以下の実施形態は、特定のオレフィン(例えば、エチレン)を参照して記載される場合があるが、当業者には自明であるように、他のオレフィン類も同様に用いることができる。また、各種触媒種を用いて四塩化炭素とオレフィンの反応を触媒してもよい。これら触媒の多くは反応媒質に不溶性または一部可溶性の種であるか、そのような種の誘導体である。一般的な触媒または触媒前駆体は鉄であり、従って、本発明の実施形態は鉄を参照して記載されることがあるが、当業者には自明であるように本発明の実施形態は、同様に他の不溶性または一部可溶性の触媒あるいは触媒前駆体まで広げることができる。また、当業者には自明であるが、これらの不溶性または一部可溶性の触媒を、触媒を補完すると考えられている共触媒または配位子と共に用いてもよい。例えば、リン酸トリブチルは、鉄触媒と共同して用いられている。従って、本発明の実施形態は、鉄と共に用いられる共触媒または配位子としてリン酸トリブチルを参照して記載される場合があるが、当業者には自明であるように本発明は他の共触媒または配位子の使用まで広げることができる。
上述のように、四塩化炭素は、鉄粉またはその誘導体などの触媒種の存在で、エチレンなどのオレフィンと反応して反応器51内で塩素化プロパンを生成する。特に、四塩化炭素はエチレンと反応して1,1,1,3-テトラクロロプロパンを生成する。これに関しては、米国公開第2004/0225166号および2009/0216055号を参照により本明細書に組み込む。
反応器51から出て行く反応器流出物63は、所望の塩素化プロパン生成物(例えば、1,1,1,3-テトラクロロプロパン)と、未反応の反応物(例えば、四塩化炭素およびエチレン)、反応副生物、触媒、および触媒残部とを含む。従って、反応器流出物63は、粗塩素化炭化水素流(例えば、1,1,1,3-テトラクロロプロパン粗生成物)と言う場合がある。次いで、この粗生成物を1つ以上の蒸留技術を用いて精製し、精製塩素化プロパン流(例えば、精製1,1,1,3-テトラクロロプロパン)を得る。
Claims (3)
- 液体反応混合物内で、不溶性または一部可溶性の触媒あるいは触媒前駆体の存在で四塩化炭素をオレフィンと反応させ塩素化プロパンを製造する方法において、前記触媒または触媒前駆体からなるスラリーを前記液体反応混合物に充填する過程の前に、前記触媒または触媒前駆体からなる前記スラリーを連続攪拌し、前記連続撹拌はスラリー閉流路を経て前記スラリーを連続して循環させることで起こることを特徴とする方法。
- 前記触媒は鉄粉であり、前記オレフィンはエチレンであり、前記スラリー内の鉄粉の濃度は約0.02~約5.0wt%である、請求項1に記載の方法。
- 前記四塩化炭素およびオレフィンを反応器内で反応させ、前記スラリー閉流路は前記反応器内の圧力よりも高い圧力で維持され、前記スラリー閉流路内のスラリーの温度は四塩化炭素の沸点よりも低い温度で維持される、請求項1に記載の方法。
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PCT/US2017/043469 WO2018022488A1 (en) | 2016-07-26 | 2017-07-24 | Methods for producing halogenated propanes |
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Country | Link |
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US (1) | US10787404B2 (ja) |
EP (2) | EP3490965B1 (ja) |
JP (3) | JP7017555B2 (ja) |
KR (2) | KR20230087618A (ja) |
CN (3) | CN118047658A (ja) |
CA (2) | CA3203916C (ja) |
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WO2020146722A1 (en) | 2019-01-10 | 2020-07-16 | Occidental Chemical Corporation | Photochlorination of partially-chlorinated chloromethanes to carbon tetrachloride |
US10994945B2 (en) * | 2019-09-18 | 2021-05-04 | Plastrac Inc. | Granular metering system |
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JP2016509001A (ja) | 2013-02-04 | 2016-03-24 | ハネウェル・インターナショナル・インコーポレーテッド | 1,1,2,3−テトラクロロプロペンの合成 |
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