CN108530261A - 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 - Google Patents
氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 Download PDFInfo
- Publication number
- CN108530261A CN108530261A CN201810409549.4A CN201810409549A CN108530261A CN 108530261 A CN108530261 A CN 108530261A CN 201810409549 A CN201810409549 A CN 201810409549A CN 108530261 A CN108530261 A CN 108530261A
- Authority
- CN
- China
- Prior art keywords
- hexafluoro
- butine
- reaction
- quaternary ammonium
- ammonium salts
- 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.)
- Pending
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- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000007033 dehydrochlorination reaction Methods 0.000 title abstract description 23
- 238000005660 chlorination reaction Methods 0.000 title abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 100
- -1 alkyl quaternary ammonium salts Chemical class 0.000 claims abstract description 55
- 239000007864 aqueous solution Substances 0.000 claims abstract description 46
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 7
- 238000004064 recycling Methods 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 13
- 239000011780 sodium chloride Substances 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 150000003841 chloride salts Chemical group 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 27
- 229910052799 carbon Inorganic materials 0.000 abstract description 23
- 239000002736 nonionic surfactant Substances 0.000 abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000376 reactant Substances 0.000 abstract description 8
- CXIGIYYQHHRBJC-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane Chemical class FC(F)(F)CCC(F)(F)F CXIGIYYQHHRBJC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 238000004817 gas chromatography Methods 0.000 description 22
- 239000003444 phase transfer catalyst Substances 0.000 description 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 19
- 235000011089 carbon dioxide Nutrition 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000001450 anions Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 229940006460 bromide ion Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000370738 Chlorion Species 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 5
- PHFDTSRDEZEOHG-UHFFFAOYSA-N hydron;octan-1-amine;chloride Chemical class Cl.CCCCCCCCN PHFDTSRDEZEOHG-UHFFFAOYSA-N 0.000 description 5
- DRNMSWBRUAIIJO-UHFFFAOYSA-N 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane Chemical class FC(F)(F)C(Cl)C(Cl)C(F)(F)F DRNMSWBRUAIIJO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 229940067739 octyl sulfate Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- UZZYXUGECOQHPU-UHFFFAOYSA-N sulfuric acid monooctyl ester Natural products CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000010792 warming 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZSAIDYISADJCTG-UHFFFAOYSA-N CC(CCCCCCC)P(CCCCCCCC)CCCCCCCC Chemical compound CC(CCCCCCC)P(CCCCCCCC)CCCCCCCC ZSAIDYISADJCTG-UHFFFAOYSA-N 0.000 description 2
- RQPPQFVLBRPPHM-UHFFFAOYSA-N CCCCCCCCP(CCCCCCCC)C(C)CCCCCCC.N Chemical class CCCCCCCCP(CCCCCCCC)C(C)CCCCCCC.N RQPPQFVLBRPPHM-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- BSRRYOGYBQJAFP-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluorobutane Chemical compound CC(F)C(F)(F)C(F)(F)F BSRRYOGYBQJAFP-UHFFFAOYSA-N 0.000 description 1
- YTKRILODNOEEPX-UHFFFAOYSA-N 1-chlorobut-2-ene Chemical compound CC=CCCl YTKRILODNOEEPX-UHFFFAOYSA-N 0.000 description 1
- XDIDQEGAKCWQQP-UHFFFAOYSA-N 2,3-dichloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical class FC(F)(F)C(Cl)=C(Cl)C(F)(F)F XDIDQEGAKCWQQP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- OGAPTYCQAOFVBE-UHFFFAOYSA-N CCCC.[Cl].[F] Chemical compound CCCC.[Cl].[F] OGAPTYCQAOFVBE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FCTFGDVLBOGMPH-UHFFFAOYSA-N TOAC Chemical compound CC1(C)CC(N)(C(O)=O)CC(C)(C)N1[O] FCTFGDVLBOGMPH-UHFFFAOYSA-N 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- RIPUKAXZALFIMA-UHFFFAOYSA-N decan-1-amine;hydrobromide Chemical class [Br-].CCCCCCCCCC[NH3+] RIPUKAXZALFIMA-UHFFFAOYSA-N 0.000 description 1
- RMKNCYHVESPYFD-UHFFFAOYSA-N decan-1-amine;hydrochloride Chemical class [Cl-].CCCCCCCCCC[NH3+] RMKNCYHVESPYFD-UHFFFAOYSA-N 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical group CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 description 1
- DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261707220P | 2012-09-28 | 2012-09-28 | |
| US201261707231P | 2012-09-28 | 2012-09-28 | |
| US61/707220 | 2012-09-28 | ||
| US61/707231 | 2012-09-28 | ||
| CN201380050238.9A CN104684877A (zh) | 2012-09-28 | 2013-09-27 | 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380050238.9A Division CN104684877A (zh) | 2012-09-28 | 2013-09-27 | 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108530261A true CN108530261A (zh) | 2018-09-14 |
Family
ID=49354928
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810409549.4A Pending CN108530261A (zh) | 2012-09-28 | 2013-09-27 | 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 |
| CN201380050238.9A Pending CN104684877A (zh) | 2012-09-28 | 2013-09-27 | 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380050238.9A Pending CN104684877A (zh) | 2012-09-28 | 2013-09-27 | 氯化反应物的脱氯化氢以制备1,1,1,4,4,4-六氟-2-丁炔 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2922809A1 (https=) |
| JP (1) | JP6272877B2 (https=) |
| KR (1) | KR102147909B1 (https=) |
| CN (2) | CN108530261A (https=) |
| IN (1) | IN2015DN01199A (https=) |
| MX (1) | MX371333B (https=) |
| WO (1) | WO2014052695A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845296A (zh) * | 2019-12-12 | 2020-02-28 | 岳阳市宇恒化工有限公司 | 一种制备炔基化合物的方法 |
| CN113677650A (zh) * | 2019-04-05 | 2021-11-19 | 科慕埃弗西有限公司 | 用于制备z-1，1，1，4，4，4-六氟丁-2-烯的方法以及用于制备其的中间体 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9440896B2 (en) | 2012-09-28 | 2016-09-13 | The Chemours Company Fc, Llc | Dehydrochlorination of HCFC-336 isomers to 1,1,1,4,4,4-hexafluoro-2-butyne |
| MX394632B (es) * | 2014-02-07 | 2025-03-24 | Chemours Co Fc Llc | Proceso integrado para la produccion de z-1,1,1,4,4,4-hexafluoro-2-buteno. |
| US9328042B2 (en) | 2014-08-11 | 2016-05-03 | The Chemours Company Fc, Llc | Integrated process for the production of Z-1,1,1,4,4,4-hexafluoro-2-butene |
| CN106349007B (zh) * | 2016-08-22 | 2019-06-11 | 巨化集团技术中心 | 一种z-hfo-1336的制备方法 |
| EP3658523B1 (en) * | 2017-07-27 | 2023-04-26 | The Chemours Company FC, LLC | Process for preparing (z)-1,1,1,4,4,4-hexafluoro-2-butene |
| KR102885018B1 (ko) * | 2019-02-21 | 2025-11-17 | 다이킨 고교 가부시키가이샤 | 할로겐화알켄 화합물 및 불화알킨 화합물의 제조 방법 |
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| US12421181B2 (en) * | 2019-04-05 | 2025-09-23 | The Chemours Company Fc, Llc | Process for producing 1,1,1,4,4,4-hexafluorobut-2-ene |
| CN113939492B (zh) * | 2019-04-05 | 2024-05-17 | 科慕埃弗西有限公司 | 用于制备z-1,1,1,4,4,4-六氟丁-2-烯的方法以及用于制备其的中间体 |
| ES3009718T3 (en) * | 2019-04-05 | 2025-03-31 | Chemours Co Fc Llc | Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same |
| CN110950735B (zh) * | 2019-10-22 | 2022-08-30 | 浙江巨化技术中心有限公司 | 一种气相法制备1,1,1,4,4,4-六氟-2-丁炔的方法 |
| JP7697960B2 (ja) | 2020-03-04 | 2025-06-24 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | （ｚ）－１，１，１，４，４，４－ヘキサフルオロ－２－ブテン及び中間体を生成するためのプロセス |
| CN114409514B (zh) * | 2021-12-21 | 2023-07-18 | 西安近代化学研究所 | 一种1,1,1,4,4,4-六氟-2-丁酮的合成方法 |
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| WO2025019740A1 (en) | 2023-07-20 | 2025-01-23 | The Chemours Company Fc, Llc | Compositions comprising 1,1,1,4,4,4-hexafluoro-2-butyne |
| WO2025019738A1 (en) | 2023-07-20 | 2025-01-23 | The Chemours Company Fc, Llc | Compositions of chlorofluorinated compounds |
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- 2013-09-27 KR KR1020157007748A patent/KR102147909B1/ko active Active
- 2013-09-27 CN CN201380050238.9A patent/CN104684877A/zh active Pending
- 2013-09-27 WO PCT/US2013/062080 patent/WO2014052695A1/en not_active Ceased
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| CN101675017A (zh) * | 2007-04-17 | 2010-03-17 | 中央硝子株式会社 | 3，3，3-三氟丙炔的制造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113677650A (zh) * | 2019-04-05 | 2021-11-19 | 科慕埃弗西有限公司 | 用于制备z-1，1，1，4，4，4-六氟丁-2-烯的方法以及用于制备其的中间体 |
| CN113677650B (zh) * | 2019-04-05 | 2024-04-12 | 科慕埃弗西有限公司 | 用于制备z-1，1，1，4，4，4-六氟丁-2-烯的方法以及用于制备其的中间体 |
| CN110845296A (zh) * | 2019-12-12 | 2020-02-28 | 岳阳市宇恒化工有限公司 | 一种制备炔基化合物的方法 |
Also Published As
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|---|---|
| IN2015DN01199A (https=) | 2015-06-26 |
| MX371333B (es) | 2020-01-27 |
| JP6272877B2 (ja) | 2018-01-31 |
| KR102147909B1 (ko) | 2020-08-25 |
| KR20150061638A (ko) | 2015-06-04 |
| CN104684877A (zh) | 2015-06-03 |
| JP2015530417A (ja) | 2015-10-15 |
| MX2015003797A (es) | 2015-07-14 |
| EP2922809A1 (en) | 2015-09-30 |
| WO2014052695A1 (en) | 2014-04-03 |
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