JP2011507873A - 2,3−ジクロロブタジエン−1,3を製造するための方法 - Google Patents
2,3−ジクロロブタジエン−1,3を製造するための方法 Download PDFInfo
- Publication number
- JP2011507873A JP2011507873A JP2010539737A JP2010539737A JP2011507873A JP 2011507873 A JP2011507873 A JP 2011507873A JP 2010539737 A JP2010539737 A JP 2010539737A JP 2010539737 A JP2010539737 A JP 2010539737A JP 2011507873 A JP2011507873 A JP 2011507873A
- Authority
- JP
- Japan
- Prior art keywords
- dichlorobutadiene
- phase
- composition
- chlorinated
- mixture
- 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.)
- Granted
Links
- LIFLRQVHKGGNSG-UHFFFAOYSA-N 2,3-dichlorobuta-1,3-diene Chemical compound ClC(=C)C(Cl)=C LIFLRQVHKGGNSG-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 86
- IXZVKECRTHXEEW-UHFFFAOYSA-N 1,2,3,4-tetrachlorobutane Chemical compound ClCC(Cl)C(Cl)CCl IXZVKECRTHXEEW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 21
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 239000006227 byproduct Substances 0.000 claims description 40
- 239000012071 phase Substances 0.000 claims description 40
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 239000008346 aqueous phase Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 16
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 16
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000007033 dehydrochlorination reaction Methods 0.000 abstract description 23
- 238000005660 chlorination reaction Methods 0.000 abstract description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000047 product Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000376 reactant Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 9
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- -1 alkane compounds Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- WZUZDBPJFHQVJC-UHFFFAOYSA-N 2,3,4-trichlorobut-1-ene Chemical compound ClCC(Cl)C(Cl)=C WZUZDBPJFHQVJC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000012018 catalyst precursor Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- SXCATGXBSQWDDJ-UHFFFAOYSA-N 1,2,4-trichlorobut-2-ene Chemical compound ClCC=C(Cl)CCl SXCATGXBSQWDDJ-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 229920001084 poly(chloroprene) Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 3
- PDKAXHLOFWCWIH-UHFFFAOYSA-N 1,1-dichlorobuta-1,3-diene Chemical compound ClC(Cl)=CC=C PDKAXHLOFWCWIH-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RCBKHVTUYAGMLB-UHFFFAOYSA-N 1,1,2,3-tetrachlorobuta-1,3-diene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C RCBKHVTUYAGMLB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- VDJQAAJIRSFMIX-UHFFFAOYSA-M 2-bromoethyl(triethyl)phosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CCBr VDJQAAJIRSFMIX-UHFFFAOYSA-M 0.000 description 1
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HGOVVCKGNSKEKR-UHFFFAOYSA-M [Cl-].CCCCCCCCCCCCCCCCC=C[P+](C)(C)C Chemical compound [Cl-].CCCCCCCCCCCCCCCCC=C[P+](C)(C)C HGOVVCKGNSKEKR-UHFFFAOYSA-M 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BMDRYIFEJILWIP-UHFFFAOYSA-M butyl(triethyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CC)(CC)CC BMDRYIFEJILWIP-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical group ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- JQOKKSBSQLTLFJ-UHFFFAOYSA-M cyclohexyl(dimethyl)sulfanium;chloride Chemical compound [Cl-].C[S+](C)C1CCCCC1 JQOKKSBSQLTLFJ-UHFFFAOYSA-M 0.000 description 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- FZCCKDYTOZQJJR-UHFFFAOYSA-M hexyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCC[N+](C)(C)C FZCCKDYTOZQJJR-UHFFFAOYSA-M 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- VPQFMXKHSQXZRW-UHFFFAOYSA-M methyl(dioctadecyl)sulfanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[S+](C)CCCCCCCCCCCCCCCCCC VPQFMXKHSQXZRW-UHFFFAOYSA-M 0.000 description 1
- HMWWZNGANFYVPX-UHFFFAOYSA-M methyl(trioctyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](C)(CCCCCCCC)CCCCCCCC HMWWZNGANFYVPX-UHFFFAOYSA-M 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- GYLDXXLJMRTVSS-UHFFFAOYSA-N n-butylacetamide Chemical compound CCCCNC(C)=O GYLDXXLJMRTVSS-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- DMBRSBVPQSDXHK-UHFFFAOYSA-M triethyl(pentyl)azanium;chloride Chemical compound [Cl-].CCCCC[N+](CC)(CC)CC DMBRSBVPQSDXHK-UHFFFAOYSA-M 0.000 description 1
- OWUGVJBQKGQQKJ-UHFFFAOYSA-M trimethylsulfanium;chloride Chemical compound [Cl-].C[S+](C)C OWUGVJBQKGQQKJ-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- C07C21/19—Halogenated dienes
- C07C21/20—Halogenated butadienes
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
A.1,2,3,4−テトラクロロブタンを含む組成物を、少なくとも10-9のKbを有する塩基を含む水性混合物と、前記1,2,3,4−テトラクロロブタンを脱塩化水素するのに十分な温度で接触させ、それにより、1)a)2,3−ジクロロブタジエン−1,3とb)2,3−ジクロロブタジエン−1,3以外の塩素化ブテンを含む塩素化副生物との混合物を含む第1の相および2)水相を含む第2の相の少なくとも2つの相を有する第1の反応生成物を生成する工程と;
B.前記第1の相を前記水相から分離する工程と;
C.前記第1の相を、前記水相から分離した後、前記塩素化副生物をさらに塩素化するには十分ではあるが、前記第1の相に含まれる2,3−ジクロロブタジエン−1,3の20%超をより高度に塩素化された化学種に転化させるには不十分な量の塩素と接触させて、それにより、第2の反応生成物を生成する工程と;
D.前記第2の反応生成物から2,3−ジクロロブタジエン−1,3を含む組成物を単離する工程であって、前記組成物の総重量を基準にして前記組成物の少なくとも90重量%が2,3−ジクロロブタジエン−1,3である、工程と
を含む、方法に関する。
A.1,2,3,4−テトラクロロブタンを含む組成物を少なくとも10-9のKbを有する塩基を含む水性混合物と、前記1,2,3,4−テトラクロロブタンを脱塩化水素するのに十分な温度で接触させ、それにより、1)a)2,3−ジクロロブタジエン−1,3とb)2,3−ジクロロブタジエン−1,3以外の塩素化ブテンを含む塩素化副生物との混合物を含む第1の相および2)水相を含む第2の相の少なくとも2つの相を有する第1の反応生成物を生成する工程と;
B.前記第1の相を前記水相から分離する工程と;
C.前記第1の相を、前記水相から分離した後、前記塩素化副生物をさらに塩素化するには十分ではあるが、前記第1の相に含まれる2,3−ジクロロブタジエン−1,3の20%超をより高度に塩素化された化学種に転化させるには不十分な量の塩素と接触させ、それにより、第2の反応生成物を生成する工程と;
D.前記第2の反応生成物から2,3−ジクロロブタジエン−1,3を含む組成物を単離する工程であって、前記組成物の総重量を基準にして前記組成物の少なくとも90重量%が2,3−ジクロロブタジエン−1,3である、工程と
を含む方法によって調製される、組成物に関する。
圧搾空気式攪拌機を備えた反応器に、100モル部のメソ−1,2,3,4−テトラクロロブタン、ビス(β−ヒドロキシプロピル)ココ−ベンジルアミン塩化物相間移動触媒および水中フェノチアジンの水性混合物を加えた。この混合物中の相間移動触媒の量は、総有機物供給量を基準にして1重量%であり、混合物中のフェノチアジンの量は、総有機物供給量を基準にして2000重量百万分率であった。混合物の温度を80℃に調節し、次いで、この有機混合物に、220モル部の水溶液中水酸化ナトリウム(18重量%水酸化ナトリウム)を約10分間かけて添加した。反応器の温度を生成物のエバポレート除去により、60℃と80℃の間に制御した。水酸化ナトリウム溶液の添加を開始してから約30分後に反応が止まるまで、蒸気を塔頂から取り出し、凝縮した。塔頂凝縮液をデカントして、水相から有機液相を分離した。有機相は72.4モル%の2,3−ジクロロブタジエン−1,3、2.5モル%の1,2,4−トリクロロ−2−ブテン、0.9モル%の2,3,4−トリクロロブテン−1、1.0モル%の未反応のメソ−テトラクロロブタン、20.9モル%の他のジクロロブタジエン異性体および2.3モル%の未同定の化合物を含んでいた。
Claims (11)
- 2,3−ジクロロブタジエン−1,3を含む組成物を製造するための方法であって、
A.1,2,3,4−テトラクロロブタンを含む組成物を少なくとも10-9のKbを有する塩基を含む水性混合物と、前記1,2,3,4−テトラクロロブタンを脱塩化水素するのに十分な温度で接触させ、それにより、1)a)2,3−ジクロロブタジエン−1,3とb)2,3−ジクロロブタジエン−1,3以外の塩素化ブテンを含む塩素化副生物との混合物を含む第1の相および2)水相を含む第2の相の少なくとも2つの相を有する第1の反応生成物を生成する工程と;
B.前記第1の相を前記水相から分離する工程と;
C.前記水相から分離した後に、前記第1の相を、前記塩素化副生物をさらに塩素化するには十分ではあるが、前記第1の相に含まれる前記2,3−ジクロロブタジエン−1,3の20%超をより高度に塩素化された化学種に転化させるには不十分な量の塩素と接触させて、それにより、第2の反応生成物を生成する工程と;
D.前記第2の反応生成物から2,3−ジクロロブタジエン−1,3を含む組成物を単離する工程であって、前記組成物の総重量を基準にして前記組成物の少なくとも90重量%が2,3−ジクロロブタジエン−1,3である、工程と
を含む、方法。 - 工程Aを相間移動触媒の存在下で行う、請求項1に記載の方法。
- 工程Cをイオン性触媒の存在下で行う、請求項1に記載の方法。
- 工程Aを気泡反応器中で行う、請求項1に記載の方法。
- 2,3−ジクロロブタジエン−1,3;塩素化副生物;未反応の1,2,3,4−テトラクロロブタン;中間体;および水を含む混合物が工程Aにおいて生成され、前記混合物は蒸発して単一の気相を形成し、前記気相は凝縮させると水相および有機相を形成する、請求項4に記載の方法。
- 2,3−ジクロロブタジエン−1,3を含む組成物であって、
A.1,2,3,4−テトラクロロブタンを含む組成物を少なくとも10-9のKbを有する塩基を含む水性混合物と、前記1,2,3,4−テトラクロロブタンを脱塩化水素するのに十分な温度で接触させ、それにより、1)a)2,3−ジクロロブタジエン−1,3とb)2,3−ジクロロブタジエン−1,3以外の塩素化ブテンを含む塩素化副生物との混合物を含む第1の相および2)水相を含む第2の相の少なくとも2つの相を有する第1の反応生成物を生成する工程と;
B.前記第1の相を前記水相から分離する工程と;
C.前記水相から分離した後に、前記第1の相を、前記塩素化副生物をさらに塩素化するには十分ではあるが、前記第1の相に含まれる前記2,3−ジクロロブタジエン−1,3の20%超をより高度に塩素化された化学種に転化させるには不十分な量の塩素と接触させ、それにより、第2の反応生成物を生成する工程と;
D.前記第2の反応生成物から2,3−ジクロロブタジエン−1,3を含む組成物を単離する工程であって、前記組成物の総重量を基準にして前記組成物の少なくとも90重量%が2,3−ジクロロブタジエン−1,3である、工程と
を含む方法によって調製される、組成物。 - 工程Aが相間移動触媒の存在下で行われる、請求項6に記載の組成物。
- 工程Cがイオン性触媒の存在下で行われる方法によって調製される、請求項6に記載の組成物。
- 工程Aが気泡反応器中で行われる方法によって調製される、請求項6に記載の組成物。
- 2,3−ジクロロブタジエン−1,3を含む組成物を製造するための方法であって、
A.1,2,3,4−テトラクロロブタンを含む組成物を少なくとも10-9のKbを有する塩基を含む水性混合物と、前記1,2,3,4−テトラクロロブタンを脱塩化水素するのに十分な温度で接触させ、それにより、1)a)2,3−ジクロロブタジエン−1,3とb)2,3−ジクロロブタジエン−1,3以外の塩素化ブテンを含む塩素化副生物との混合物を含む第1の相、および2)水相を含む第2の相の少なくとも2つの相を有する第1の反応生成物を生成する工程と;
B.前記第1の反応生成物を、前記塩素化副生物をさらに塩素化するには十分であるが、前記第1の相に含まれる前記2,3−ジクロロブタジエン−1,3の20%超をより高度に塩素化された化学種に転化させるには不十分な量の塩素と接触させ、それにより、第2の反応生成物を生成する工程と;
C.前記第2の反応生成物から2,3−ジクロロブタジエン−1,3を含む組成物を単離する工程であって、前記組成物の総重量を基準にして前記組成物の少なくとも90重量%が2,3−ジクロロブタジエン−1,3である、工程と
を含む、方法。 - 前記塩素が少なくとも96%の純度を有する、請求項1、6または10に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US816007P | 2007-12-19 | 2007-12-19 | |
US61/008,160 | 2007-12-19 | ||
US12/335,598 | 2008-12-16 | ||
US12/335,598 US8030531B2 (en) | 2007-12-19 | 2008-12-16 | Process for production of 2,3-dichlorobutadiene-1,3 |
PCT/US2008/087186 WO2009085837A2 (en) | 2007-12-19 | 2008-12-17 | Process for production of 2,3-dichlorobutadiene-1,3 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2011507873A true JP2011507873A (ja) | 2011-03-10 |
JP2011507873A5 JP2011507873A5 (ja) | 2011-11-17 |
JP5571569B2 JP5571569B2 (ja) | 2014-08-13 |
Family
ID=40789424
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010539737A Active JP5571569B2 (ja) | 2007-12-19 | 2008-12-17 | 2,3−ジクロロブタジエン−1,3を製造するための方法 |
Country Status (5)
Country | Link |
---|---|
US (2) | US8030531B2 (ja) |
EP (1) | EP2231567B1 (ja) |
JP (1) | JP5571569B2 (ja) |
CN (1) | CN101903314B (ja) |
WO (1) | WO2009085837A2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011058575A1 (en) * | 2009-11-10 | 2011-05-19 | Pidilite Industries Ltd | An improved process for the preparation of 2,3,-dichloro 1,3,butadiene from 1,3 butadiene |
CN103483144B (zh) * | 2013-09-26 | 2015-03-25 | 中国成达工程有限公司 | 二氯丁烯制二氯丁二烯的制备方法及其制备装置 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2626964A (en) * | 1948-12-22 | 1953-01-27 | Firestone Tire & Rubber Co | Preparation of 2, 3-dichloro-1, 3-butadiene by dehydrochlorination of 1, 2, 3, 4-tetrachlorobutane |
JPS4824365B1 (ja) * | 1969-11-26 | 1973-07-20 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1213396B (de) * | 1964-02-26 | 1966-03-31 | British Cellophane Ltd | Verfahren zur Herstellung von 2, 3-Dichlorbutadien |
GB1084742A (en) * | 1964-07-08 | 1967-09-27 | British Cellophane Ltd | Improvements in or relating to the manufacture of 2,3-dichloro-1,3-butadiene |
US3981937A (en) * | 1966-06-03 | 1976-09-21 | E. I. Du Pont De Nemours And Company | Dehydrohalogenation of 3,4-dichloro-1-butene |
CS137453B5 (ja) * | 1967-10-27 | 1970-07-15 | ||
US3876716A (en) * | 1968-02-28 | 1975-04-08 | Du Pont | Dehydrochlorination of chlorinated compounds |
US3639493A (en) * | 1968-02-28 | 1972-02-01 | Du Pont | Dehydrohalogenation of halogenated compounds |
DE2204708C3 (de) * | 1972-02-01 | 1975-10-16 | Wsesojusnyj Nautschno-Issledowatelskij I Projektnyj Institut Polimernych Produktow, Eriwan (Sowjetunion) | Verfahren zur Herstellung von 2,3-Dichlorbutadien-(1,3) |
DE2533429C3 (de) * | 1975-07-25 | 1979-07-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Chlorbutadien-U3) |
US4215078A (en) * | 1979-04-02 | 1980-07-29 | E. I. Du Pont De Nemours And Company | Process for manufacturing chloroprene and 2,3-dichlorobutadiene-1,3 |
JPS5791931A (en) * | 1980-11-27 | 1982-06-08 | Denki Kagaku Kogyo Kk | Preparation of 2,3-dichlorobutadiene-1,3 |
DE3208796A1 (de) * | 1982-03-11 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,3-dichlorbutadien- (1,3) |
US6380446B1 (en) * | 2000-08-17 | 2002-04-30 | Dupont Dow Elastomers, L.L.C. | Process for dehydrohalogenation of halogenated compounds |
-
2008
- 2008-12-16 US US12/335,598 patent/US8030531B2/en active Active
- 2008-12-17 EP EP08867913.9A patent/EP2231567B1/en active Active
- 2008-12-17 CN CN200880121445.8A patent/CN101903314B/zh active Active
- 2008-12-17 JP JP2010539737A patent/JP5571569B2/ja active Active
- 2008-12-17 WO PCT/US2008/087186 patent/WO2009085837A2/en active Application Filing
-
2011
- 2011-08-30 US US13/220,754 patent/US20110313216A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2626964A (en) * | 1948-12-22 | 1953-01-27 | Firestone Tire & Rubber Co | Preparation of 2, 3-dichloro-1, 3-butadiene by dehydrochlorination of 1, 2, 3, 4-tetrachlorobutane |
JPS4824365B1 (ja) * | 1969-11-26 | 1973-07-20 |
Also Published As
Publication number | Publication date |
---|---|
CN101903314A (zh) | 2010-12-01 |
US8030531B2 (en) | 2011-10-04 |
WO2009085837A3 (en) | 2009-10-01 |
JP5571569B2 (ja) | 2014-08-13 |
EP2231567B1 (en) | 2013-10-23 |
US20110313216A1 (en) | 2011-12-22 |
CN101903314B (zh) | 2014-05-28 |
EP2231567A2 (en) | 2010-09-29 |
WO2009085837A2 (en) | 2009-07-09 |
US20090163745A1 (en) | 2009-06-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2837292C (en) | Process for the production of chlorinated propenes | |
CA2894168C (en) | Process for the production of chlorinated propenes | |
JP2016509001A (ja) | 1,1,2,3−テトラクロロプロペンの合成 | |
CA2844319A1 (en) | Process for the production of chlorinated propenes | |
CA2858836A1 (en) | Sulfuryl chloride as chlorinating agent | |
EP1309530B1 (en) | Process for dehydrohalogenation of halogenated compounds | |
JP2018533607A (ja) | 2,3,3,3−テトラフルオロプロペン及び/又はフッ化ビニリデンを製造する方法 | |
JP5571569B2 (ja) | 2,3−ジクロロブタジエン−1,3を製造するための方法 | |
CA2844322A1 (en) | Process for the production of chlorinated propenes | |
JP2012140397A (ja) | ポリクロロプロパンの製造方法 | |
JP5571570B2 (ja) | 塩素化アルケンを精製するための方法 | |
JP5858830B2 (ja) | ポリクロロプロパンの製造方法 | |
JP2004168753A (ja) | ジヨードパーフルオロアルカンの製造方法 | |
CN116194430A (zh) | 用于由二氯丙烯制备五氯丙烷和四氯丙烯的方法 | |
RU2533421C1 (ru) | Способ жидкофазного хлорирования 1,3-бутадиена | |
US20050113606A1 (en) | Continuous production of chlorodifluoroacetyl fluoride via chlorotrifluoroethylene oxidation | |
JPH07101887A (ja) | ハイドロフルオロカーボンの製造方法 | |
CN105339330A (zh) | 三氟乙烯的制造方法 | |
CA2966337A1 (en) | Process for the production of hydrogen chloride, ethylene and vinyl chloride from ethane | |
JPH0133457B2 (ja) | ||
JPH09136854A (ja) | 含フッ素ビニルエーテルの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110930 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110930 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20120411 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130606 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130611 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130906 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130913 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131211 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140128 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140428 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140527 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140626 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5571569 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |