JP6251286B2 - 塩素化プロペン生成のための方法 - Google Patents
塩素化プロペン生成のための方法 Download PDFInfo
- Publication number
- JP6251286B2 JP6251286B2 JP2015549592A JP2015549592A JP6251286B2 JP 6251286 B2 JP6251286 B2 JP 6251286B2 JP 2015549592 A JP2015549592 A JP 2015549592A JP 2015549592 A JP2015549592 A JP 2015549592A JP 6251286 B2 JP6251286 B2 JP 6251286B2
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- JP
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- Prior art keywords
- dehydrochlorination
- pentachloropropane
- stream
- catalyst
- reactor
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 89
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical class CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title description 18
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 66
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical class CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 claims description 55
- 239000003054 catalyst Substances 0.000 claims description 51
- 239000000047 product Substances 0.000 claims description 49
- 238000005660 chlorination reaction Methods 0.000 claims description 39
- 230000008569 process Effects 0.000 claims description 33
- 230000003197 catalytic effect Effects 0.000 claims description 25
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 239000003518 caustics Substances 0.000 claims description 17
- 239000006227 byproduct Substances 0.000 claims description 14
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 239000007791 liquid phase Substances 0.000 claims description 11
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000000926 separation method Methods 0.000 description 21
- ATKFMEGWDYLXBP-UHFFFAOYSA-N 2-(2,4,5-trichlorophenoxy)ethanol Chemical compound OCCOC1=CC(Cl)=C(Cl)C=C1Cl ATKFMEGWDYLXBP-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 239000003999 initiator Substances 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- BUQMVYQMVLAYRU-UHFFFAOYSA-N 1,1,2,3-tetrachloropropane Chemical compound ClCC(Cl)C(Cl)Cl BUQMVYQMVLAYRU-UHFFFAOYSA-N 0.000 description 8
- LIPPKMMVZOHCIF-UHFFFAOYSA-N 1,1,2-trichloroprop-1-ene Chemical compound CC(Cl)=C(Cl)Cl LIPPKMMVZOHCIF-UHFFFAOYSA-N 0.000 description 8
- -1 chloroamine-T® Chemical class 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- IYFMQUDCYNWFTL-UHFFFAOYSA-N 1,1,2,2,3-pentachloropropane Chemical compound ClCC(Cl)(Cl)C(Cl)Cl IYFMQUDCYNWFTL-UHFFFAOYSA-N 0.000 description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 7
- 238000005336 cracking Methods 0.000 description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 7
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- FEKGWIHDBVDVSM-UHFFFAOYSA-N 1,1,1,2-tetrachloropropane Chemical compound CC(Cl)C(Cl)(Cl)Cl FEKGWIHDBVDVSM-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- PQUUGVDRLWLNGR-UHFFFAOYSA-N 2,3,3,3-tetrachloroprop-1-ene Chemical compound ClC(=C)C(Cl)(Cl)Cl PQUUGVDRLWLNGR-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
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- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 description 4
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 3
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 3
- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical class ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 description 3
- PANVCEBTPSTUEL-UHFFFAOYSA-N 1,1,2,3,3-pentachloropropane Chemical compound ClC(Cl)C(Cl)C(Cl)Cl PANVCEBTPSTUEL-UHFFFAOYSA-N 0.000 description 3
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000011968 lewis acid catalyst Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
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- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
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- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HVCSXHFGNRDDQR-UHFFFAOYSA-N 1,1,2,2,3,3-hexachloropropane Chemical compound ClC(Cl)C(Cl)(Cl)C(Cl)Cl HVCSXHFGNRDDQR-UHFFFAOYSA-N 0.000 description 1
- GRSQYISVQKPZCW-UHFFFAOYSA-N 1,1,2-trichloropropane Chemical compound CC(Cl)C(Cl)Cl GRSQYISVQKPZCW-UHFFFAOYSA-N 0.000 description 1
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- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
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- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000010457 zeolite Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
以下に、本願発明に関連する発明の実施形態を例示する。
[実施形態1]
1,2−ジクロロプロパンを含む供給流からの塩素化プロペン生成のための方法であって、前記方法により生成されるペンタクロロプロパンの少なくとも一部が、塩化アルミニウム、五塩化アンチモン、四塩化チタン、またはこれらの組み合わせからなる群より選択される少なくとも1つの脱塩化水素触媒を使用して、触媒作用によって脱塩化水素化される、方法。
[実施形態2]
前記脱塩化水素触媒の全濃度が全反応混合物の5モル%より少ない、実施形態1に記載の方法。
[実施形態3]
前記ペンタクロロプロパンが1,1,1,2,2−ペンタクロロプロパンを含む、実施形態1に記載の方法。
[実施形態4]
化学塩基の存在下において実行される少なくとも1回の追加的な液相脱塩化水素化を更に含む、実施形態1に記載の方法。
[実施形態5]
前記触媒的脱塩化水素化からの前記供給流が、前記液相脱塩化水素化へ提供される、実施形態4に記載の方法。
[実施形態6]
前記触媒的脱塩化水素化が、1,1,2,3−テトラクロロプロパンおよび未反応のペンタクロロプロパンを含む流れを生成する、実施形態1、3、または5に記載の方法。
[実施形態7]
前記触媒が、前記化学塩基脱塩化水素化の生成物により反応を停止し、前記生成物流から除去される、実施形態6に記載の方法。
[実施形態8]
前記供給流が1,2,3−トリクロロプロパンを更に含む、実施形態1に記載の方法。
[実施形態9]
HClが副生成物(複数可)として生成される、実施形態1または3に記載の方法。
[実施形態10]
HClが無水HClとして回収される、実施形態9に記載の方法。
[実施形態11]
前記化学塩基が、苛性剤、水酸化カリウム、水酸化カルシウム、またはこれらの組み合わせを含む、実施形態4、5、または7に記載の方法。
[実施形態12]
前記生成物流が、前記脱塩化水素触媒を低減するために反応停止される、実施形態1または2に記載の方法。
[実施形態13]
前記反応停止された触媒が前記生成物流から除去される、実施形態12に記載の方法。
Claims (10)
- 1,2−ジクロロプロパンを含む供給流からの1,1,2,3−テトラクロロプロペン生成のための方法であって、前記1,2−ジクロロプロパンが塩素化されて1種以上のペンタクロロプロパンを生成し、前記塩素化により生成されるペンタクロロプロパンの少なくとも一部が、塩化アルミニウムを使用して、触媒作用によって脱塩化水素化され、前記ペンタクロロプロパンが1,1,1,2,2−ペンタクロロプロパンを含み、前記触媒的脱塩化水素化が1,1,2,3−テトラクロロプロペンおよび未反応のペンタクロロプロパンを含む流れを生成する、方法。
- 前記脱塩化水素触媒の全濃度が全反応混合物の5モル%より少ない、請求項1に記載の方法。
- 化学塩基の存在下において実行される少なくとも1つの追加的な液相脱塩化水素化を更に含む、請求項1に記載の方法。
- 前記触媒的脱塩化水素化からの前記供給流が、前記液相脱塩化水素化へ提供される、請求項1に記載の方法。
- 前記触媒が、前記化学塩基脱塩化水素化の生成物により反応を停止し、前記生成物流から除去される、請求項4に記載の方法。
- 前記供給流が1,2,3−トリクロロプロパンを更に含む、請求項1に記載の方法。
- HClが副生成物として生成される、請求項1に記載の方法。
- HClが無水HClとして回収される、請求項1に記載の方法。
- 前記化学塩基が、苛性剤、水酸化カリウム、水酸化カルシウム、またはこれらの組み合わせを含む、請求項3に記載の方法。
- 前記生成物流が、前記脱塩化水素触媒を低減するために反応を停止され、前記反応停止した触媒が前記生成物流から任意に除去される、請求項1または2に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201261739341P | 2012-12-19 | 2012-12-19 | |
US61/739,341 | 2012-12-19 | ||
PCT/US2013/075863 WO2014100039A1 (en) | 2012-12-19 | 2013-12-17 | Process for the production of chlorinated propenes |
Publications (2)
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JP2016503057A JP2016503057A (ja) | 2016-02-01 |
JP6251286B2 true JP6251286B2 (ja) | 2017-12-20 |
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JP2015549592A Expired - Fee Related JP6251286B2 (ja) | 2012-12-19 | 2013-12-17 | 塩素化プロペン生成のための方法 |
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US (1) | US9475740B2 (ja) |
EP (1) | EP2935166A1 (ja) |
JP (1) | JP6251286B2 (ja) |
CN (1) | CN104918904B (ja) |
CA (1) | CA2894168C (ja) |
WO (1) | WO2014100039A1 (ja) |
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CA2856545A1 (en) | 2011-12-02 | 2013-06-06 | Dow Global Technologies Llc | Process for the production of chlorinated alkanes |
CN104024187B (zh) | 2011-12-02 | 2017-04-12 | 蓝立方知识产权有限责任公司 | 生产氯化烷烃的方法 |
WO2013096706A1 (en) | 2011-12-23 | 2013-06-27 | Dow Global Technologies, Llc | Process for the production of alkenes and/or aromatic compounds |
WO2014046970A1 (en) | 2012-09-20 | 2014-03-27 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
EP2897932A1 (en) | 2012-09-20 | 2015-07-29 | Dow Global Technologies LLC | Process for the production of chlorinated propenes |
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CA2893841C (en) | 2012-12-18 | 2018-07-24 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
JP6251286B2 (ja) | 2012-12-19 | 2017-12-20 | ブルー キューブ アイピー エルエルシー | 塩素化プロペン生成のための方法 |
US8889930B2 (en) * | 2013-01-22 | 2014-11-18 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons |
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CA2894168C (en) | 2018-04-24 |
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