JP2008545642A - 耐腐食性装置内でのクロロヒドリンの調製方法 - Google Patents
耐腐食性装置内でのクロロヒドリンの調製方法 Download PDFInfo
- Publication number
- JP2008545642A JP2008545642A JP2008511720A JP2008511720A JP2008545642A JP 2008545642 A JP2008545642 A JP 2008545642A JP 2008511720 A JP2008511720 A JP 2008511720A JP 2008511720 A JP2008511720 A JP 2008511720A JP 2008545642 A JP2008545642 A JP 2008545642A
- Authority
- JP
- Japan
- Prior art keywords
- polyhydroxylated aliphatic
- aliphatic hydrocarbon
- chlorohydrin
- chlorinating agent
- 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
- 238000000034 method Methods 0.000 title claims abstract description 132
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 title claims abstract description 118
- 238000005260 corrosion Methods 0.000 title claims description 7
- 230000007797 corrosion Effects 0.000 title claims description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 162
- 239000000203 mixture Chemical class 0.000 claims abstract description 97
- 239000012320 chlorinating reagent Substances 0.000 claims abstract description 70
- 150000002148 esters Chemical class 0.000 claims abstract description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 33
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 95
- 238000004519 manufacturing process Methods 0.000 claims description 50
- 235000011187 glycerol Nutrition 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 coatings Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 27
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 20
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 229910002804 graphite Inorganic materials 0.000 claims description 12
- 239000010439 graphite Substances 0.000 claims description 12
- 239000007769 metal material Substances 0.000 claims description 12
- 238000003860 storage Methods 0.000 claims description 12
- 239000003822 epoxy resin Substances 0.000 claims description 10
- 229920000647 polyepoxide Polymers 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 9
- 210000003298 dental enamel Anatomy 0.000 claims description 9
- 229910000831 Steel Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 229920001568 phenolic resin Polymers 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000010959 steel Substances 0.000 claims description 8
- 238000012546 transfer Methods 0.000 claims description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000004568 cement Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 229920002313 fluoropolymer Polymers 0.000 claims description 7
- 239000004811 fluoropolymer Substances 0.000 claims description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229920001169 thermoplastic Polymers 0.000 claims description 7
- 239000004416 thermosoftening plastic Substances 0.000 claims description 7
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 6
- 229910001182 Mo alloy Inorganic materials 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910052715 tantalum Inorganic materials 0.000 claims description 6
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 6
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- 229910001362 Ta alloys Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001903 high density polyethylene Polymers 0.000 claims description 4
- 239000004700 high-density polyethylene Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229920002492 poly(sulfone) Polymers 0.000 claims description 4
- 229920001225 polyester resin Polymers 0.000 claims description 4
- 239000004645 polyester resin Substances 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 229910010293 ceramic material Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 239000000806 elastomer Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000005011 phenolic resin Substances 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000010453 quartz Substances 0.000 claims description 3
- 239000011819 refractory material Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 229910001316 Ag alloy Inorganic materials 0.000 claims description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 2
- 229910000906 Bronze Inorganic materials 0.000 claims description 2
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 229910001257 Nb alloy Inorganic materials 0.000 claims description 2
- 229910000990 Ni alloy Inorganic materials 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002033 PVDF binder Substances 0.000 claims description 2
- 229910001252 Pd alloy Inorganic materials 0.000 claims description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 2
- 229920000491 Polyphenylsulfone Polymers 0.000 claims description 2
- 229910001260 Pt alloy Inorganic materials 0.000 claims description 2
- 239000006004 Quartz sand Substances 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910001245 Sb alloy Inorganic materials 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001069 Ti alloy Inorganic materials 0.000 claims description 2
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910001093 Zr alloy Inorganic materials 0.000 claims description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011473 acid brick Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002140 antimony alloy Substances 0.000 claims description 2
- GVFOJDIFWSDNOY-UHFFFAOYSA-N antimony tin Chemical compound [Sn].[Sb] GVFOJDIFWSDNOY-UHFFFAOYSA-N 0.000 claims description 2
- 239000010974 bronze Substances 0.000 claims description 2
- OGSYQYXYGXIQFH-UHFFFAOYSA-N chromium molybdenum nickel Chemical compound [Cr].[Ni].[Mo] OGSYQYXYGXIQFH-UHFFFAOYSA-N 0.000 claims description 2
- IIQVQTNFAKVVCM-UHFFFAOYSA-N copper niobium Chemical compound [Cu][Nb][Nb] IIQVQTNFAKVVCM-UHFFFAOYSA-N 0.000 claims description 2
- CIYRLONPFMPRLH-UHFFFAOYSA-N copper tantalum Chemical compound [Cu].[Ta] CIYRLONPFMPRLH-UHFFFAOYSA-N 0.000 claims description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000010431 corundum Substances 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 229910052571 earthenware Inorganic materials 0.000 claims description 2
- 229920006241 epoxy vinyl ester resin Polymers 0.000 claims description 2
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 claims description 2
- 229920001973 fluoroelastomer Polymers 0.000 claims description 2
- HDNHWROHHSBKJG-UHFFFAOYSA-N formaldehyde;furan-2-ylmethanol Chemical compound O=C.OCC1=CC=CO1 HDNHWROHHSBKJG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007849 furan resin Substances 0.000 claims description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 2
- JUWSSMXCCAMYGX-UHFFFAOYSA-N gold platinum Chemical compound [Pt].[Au] JUWSSMXCCAMYGX-UHFFFAOYSA-N 0.000 claims description 2
- PQTCMBYFWMFIGM-UHFFFAOYSA-N gold silver Chemical compound [Ag].[Au] PQTCMBYFWMFIGM-UHFFFAOYSA-N 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- WHJFNYXPKGDKBB-UHFFFAOYSA-N hafnium;methane Chemical compound C.[Hf] WHJFNYXPKGDKBB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- CLDVQCMGOSGNIW-UHFFFAOYSA-N nickel tin Chemical compound [Ni].[Sn] CLDVQCMGOSGNIW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- RHDUVDHGVHBHCL-UHFFFAOYSA-N niobium tantalum Chemical compound [Nb].[Ta] RHDUVDHGVHBHCL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229920011301 perfluoro alkoxyl alkane Polymers 0.000 claims description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 2
- 229910052573 porcelain Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 229910052851 sillimanite Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
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- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 2
- PEVRKKOYEFPFMN-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoroprop-1-ene;1,1,2,2-tetrafluoroethene Chemical group FC(F)=C(F)F.FC(F)=C(F)C(F)(F)F PEVRKKOYEFPFMN-UHFFFAOYSA-N 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 description 25
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- 150000002924 oxiranes Chemical class 0.000 description 18
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- 238000005660 chlorination reaction Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
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- 239000000376 reactant Substances 0.000 description 11
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- 150000003839 salts Chemical class 0.000 description 10
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 239000007806 chemical reaction intermediate Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
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- 229910052749 magnesium Inorganic materials 0.000 description 4
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- 238000005809 transesterification reaction Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 3
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 3
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 description 3
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Abstract
Description
SOLVAY SAのWO2005/054167出願には、グリセリンを、触媒としてのアジピン酸などの酸の存在下で、塩化水素と反応させることによるジクロロプロパノールの調製方法が記載されている。
(a) ポリヒドロキシル化された脂肪族炭化水素、ポリヒドロキシル化された脂肪族炭化水素のエステル、またはこれらの混合物を、塩化水素を含有する塩素化剤と反応させる工程と、
(b) この工程を行うために適切な条件下で、塩素化剤に耐性がある材料で作成されているかあるいは被覆されている装置内で行う少なくとも1つの別の工程と、
を含む、クロロヒドリンの調製方法を提供する。
本発明の方法では、以下の利点が実現される。
(a) 装置の寿命が延びる。
(b) プロセスにおける蒸気の取扱が単純化される。
(c) プロセスの全費用が低減される。
(d) クロロヒドリンの調製のためのプロセスの下流のプロセス、例えば、低い金属含量を必要とする高温酸化によるパージ処理などに問題が生じない。
(e) ポリヒドロキシル化された脂肪族炭化水素の塩素化プロセスから得られ、クロロヒドリンと水の混合物として供給される、エポキシドの製造からの水性廃液の質が、金属含量が異常に高いことによって悪影響を受けず、この結果、金属含量を低減させる目的で、この水性排出液に特別な精製処理を施す必要がない。
(a) ポリヒドロキシル化された脂肪族炭化水素、ポリヒドロキシル化された脂肪族炭化水素のエステル、またはこれらの混合物を、塩化水素を含有する塩素化剤と反応させる部分と、
(b)塩素化剤に耐性がある材料で作られたかあるいは前記材料で被覆された装置内に作られた少なくとも1つの別の部分と、
を含むプラントを提供する。
ヒドロキシル官能基(OH)を有するポリヒドロキシル化された脂肪族炭化水素のそれぞれの炭素は、2つ以上のOH基を有することはできず、sp3混成を有していなければならない。OH基を有する炭素原子は、第一級、第二級または第三級であれってよい。本発明において使用するポリヒドロキシル化された脂肪族炭化水素は、1つのOH基を持つsp3混成炭素原子を少なくとも2つ含有していなければならない。ポリヒドロキシル化された脂肪族炭化水素には、隣接ジオール(1,2-ジオール)または隣接トリオール(1,2,3-トリオール)を含有する任意の炭化水素が、これらの反復単位がより多く、隣接し、連続しているものを含めて含まれる。ポリヒドロキシル化された脂肪族炭化水素の定義には、例えば、1,3-、1,4-、1,5-および1,6-ジオール官能基の1つまたは複数も含まれる。ポリヒドロキシル化された脂肪族炭化水素は、ポリビニルアルコールなどのポリマーであってもよい。例えば、ジェミナルジオールは、この種類のポリヒドロキシル化された脂肪族炭化水素からは除外される。
アルカリ金属、アルカリ土類金属、鉄、ニッケル、銅、鉛、ヒ素、コバルト、チタン、カドミウム、アンチモン、水銀、亜鉛、セレン、アルミニウム、ビスマス、およびこれらの混合物から選択される金属を特に挙げる。
本発明による方法において、クロロヒドリンがジクロロプロパノールである場合には、これは一般的に異性体1,3-ジクロロプロパン-2-オールおよび2,3-ジクロロプロパン-1-オールを含む混合化合物の形態で使用される。この混合物は、一般的に1重量%を超える、好ましくは5重量%を超える、特に50%を超える2つの異性体を含有する。この混合物は、一般的に99.9重量%未満、好ましくは95重量%未満、とりわけ90重量%未満の2つの異性体を含有する。この混合物の他の成分は、ジクロロプロパノールの調製方法に由来する化合物、残留反応物質、反応副生成物、溶媒、および特に水などであり得る。
装置に関する要因は、例えば、形状、大きさ、複雑さ、および保護されるべき装置の表面に手が届くかどうかである。
SOLVAY SAの出願WO 2005/054167の6ページ3行目〜23行目の記載により開示されている材料が特に好ましい。
適切な材料としては、例えば、金属材料および非金属材料を挙げる。
これらの材料は、大部分において使用されているか、被覆加工の形態で使用されるか、あるいは任意のコーティング法により使用されていてよい。
「白金」族の金属として、ロジウム、イリジウム、ルテニウム、パラジウム、およびオスミウムを挙げる。
金属材料として、金およびタンタルが好ましい。
金属および合金は、大部分において使用されているか、被覆加工の形態で使用されるか、あるいは任意のコーティング法により使用されていてよい。
Ti Gr 26およびMonel 400でできた腐食試験片を、120℃で90日間、液状のグリセリン塩化水素処理反応混合物中に置いた。この液状のグリセリン塩化水素処理反応混合物は、20%のジクロロプロパノール、18%のグリセロールモノクロロヒドリン、2%のグリセリン、6%のモノ-およびポリ塩素化グリセリンオリゴマー、6%の水、0.8%のHClからなり、残りは、触媒として働くカルボン酸およびそのエステルからなる。試験片はこの反応混合物に完全に溶解した。
反応混合物中に液相状態で浸漬された場合に、グリセリンの塩化水素処理のための反応器からのエナメル鋼の構成要素、熱交換器からのグラファイトでできた構成要素、および蒸留カラムからのPTFEでできた構成要素は、腐食の兆候を示さなかった。
Claims (26)
- (a) ポリヒドロキシル化された脂肪族炭化水素、ポリヒドロキシル化された脂肪族炭化水素のエステル、またはこれらの混合物を、塩化水素を含有する塩素化剤と反応させる工程と、
(b) 前記工程を行うために適切な条件下で、塩素化剤に耐性がある材料で作成されているかあるいは被覆されている装置内で行う少なくとも1つの別の工程と、
を含むクロロヒドリンの調製方法。 - ポリヒドロキシル化された脂肪族炭化水素、ポリヒドロキシル化された脂肪族炭化水素のエステル、またはこれらの混合物を再生可能な原料から出発して得る、請求項1に記載の方法。
- 前記塩素水素が、気体塩化水素および塩化水素の水溶液の組合せ、または塩化水素の水溶液である、請求項1または2に記載の方法。
- 前記別の工程が、前記クロロヒドリンの調製方法において用いる化合物もしくは前記方法の生成物の、貯蔵、供給、引き抜き、移送、化学的処理もしくは物理的処理工程である、請求項1から3のいずれか一項に記載の方法。
- 前記装置が、化合物が貯蔵される容器、化学反応が行われる容器、および/または物理的操作が行われる容器、これらの容器を連結する配管およびコネクタ、ラインの漏れ止めを確実にする要素、容器間の化合物の移送に必要な器具、ならびに、貯蔵の監視のため、化合物の移送のため、ならびに化学反応および物理的操作の実施のために必要なさまざまなパラメータを測定するための器具および機器から選択される、請求項1から4のいずれか一項に記載の方法。
- 前記装置が、0℃以上200℃以下の温度および0.01の絶対bar以上50 bar以下の圧力に維持される、請求項1から5のいずれか一項に記載の方法。
- 塩素化剤に耐性がある前記材料が、金属材料、ならびに、エラストマー、熱可塑性プラスチック、ガラス/樹脂積層体、セラミック、金属セラミック材料、耐火材料、コーティング、耐酸性セメント、自己硬化性耐酸性セメント、含浸グラファイト、カーボン、ガラス、石英、エナメル、磁器、陶器、および耐酸煉瓦をベースにした非金属材料から選択される、請求項1から6のいずれか一項に記載の方法。
- 塩素化剤に耐性がある前記材料が、大部分において使用されているか、被覆加工の形態で使用されるか、あるいは任意のコーティング法により使用されている、請求項1から7のいずれか一項に記載の方法。
- 前記金属材料が、タンタルおよびタンタル合金、ジルコニウムおよびジルコニウム合金、チタニウムおよびチタン合金、白金および「白金」族の金属、銀および金を少なくとも30%含む銀−金−パラジウム合金、金および金−銀合金および金−白金合金、モリブデンおよびモリブデン合金、ニッケル−モリブデン合金、ニッケル−クロム−モリブデン合金、銅合金(ケイ素青銅)、銅−タンタルおよび銅−ニオブ合金、5%のアンチモンを含有するスズ−アンチモン合金、スズ−ニッケル合金、ニオブおよびニオブ−タンタル合金から選択される、請求項8または9に記載の方法。
- 前記金属材料が、金およびタンタルから選択される、請求項9に記載の方法。
- 前記「白金」族の金属が、ロジウム、イリジウム、ルテニウム、パラジウム、およびオスミウムから選択される、請求項9に記載の方法。
- 前記非金属材料が、エナメル;高密度ポリエチレン;フルオロエラストマーをベースにしたエラストマー;ポリプロピレン、フルオロポリマー、アクリロニトリル−ブタジエン−スチレンコポリマー、アクリロニトリル(40%)−ビニルクロリド(60%)コポリマー、ポリスルホン、ポリフェニレンサルファイド、およびポリフェニルスルホンをベースにした熱可塑性プラスチック;ポリエステル樹脂、フェノール樹脂、フラン樹脂、エポキシ樹脂、およびビニルエステル樹脂をベースにしたガラス/樹脂積層体;アルミナおよびコランダムをベースにしたセラミック;炭化ハフニウムおよび窒化チタンをベースにした金属セラミック材料;炭化ケイ素、シリカ、高シリカ含量ケイ酸アルミニウム、ケイ酸ジルコニウム、酸化ジルコニウム、およびシリマナイト(Al2O3-SiO2)をベースにした耐火材料;エポキシ樹脂、Sakaphen、フェノール−ホルムアルデヒド樹脂に基づくBrauthite、およびisolemailに基づくBrauthiteをベースにしたコーティング;珪酸塩、フェノール−ホルムアルデヒド樹脂、および石英砂と混合した硫化物をベースにした耐酸性セメント;グラファイトを混合したフェノール−ホルムアルデヒド樹脂をベースにした自己硬化性耐酸性セメント;グラファイトを混合したフルフリルアルコール樹脂;カーボンと混合したエポキシ樹脂;および石英と混合したポリエステル樹脂、から選択される、請求項7または8に記載の方法
- 前記非金属材料が、エナメル、高密度ポリエチレン、ポリプロピレン、フルオロポリマーをベースにした熱可塑性プラスチック、ポリスルホンおよびポリサルファイド、グラファイト、および含浸グラファイトから選択される、請求項12に記載の方法。
- 前記フルオロポリマーをベースにした熱可塑性プラスチックが、ポリビニリデンフルオリド、ポリテトラフルオロエチレン、ペルフルオロアルコキシアルカン、エチレン−テトラフルオロエチレンコポリマー、テトラフルオロエチレン−ペルフルオロメチルビニルエーテルコポリマー、およびテトラフルオロエチレン−ヘキサフルオロプロピレンコポリマーから選択される、請求項13に記載の方法。
- エナメルがスチール被覆材料として用いられ、塩素化剤に耐性がある前記材料が、エナメル鋼である、請求項13に記載の方法。
- 前記ポリヒドロキシル化された脂肪族炭化水素が、エチレングリコール、プロピレングリコール、クロロプロパンジオール、グリセリン、およびこれらの少なくとも2つの混合物から選択される、請求項1から15のいずれか一項に記載の方法。
- 前記クロロヒドリンが、クロロエタノール、クロロプロパノール、クロロプロパンジオール、ジクロロプロパノール、およびこれらの少なくとも2つの混合物から選択される、請求項1から16のいずれか一項に記載の方法。
- 前記ポリヒドロキシル化された脂肪族炭化水素がグリセリンであり、前記クロロヒドリンがジクロロプロパノールである、請求項16または17に記載の方法。
- 続いてジクロロプロパノールの脱塩化水素によるエピクロロヒドリンの調製を行う、請求項18に記載の方法。
- 前記エピクロロヒドリンが、エポキシ樹脂の製造に使用される、請求項19に記載の方法。
- ポリヒドロキシル化された脂肪族炭化水素、ポリヒドロキシル化された脂肪族炭化水素のエステル、またはこれらの混合物を、塩化水素を含有する塩素化剤と反応させる工程を含むクロロヒドリンの調製方法の、前記反応工程以外の少なくとも1つの工程における、塩素化剤に耐性がある材料で被覆されたかあるいは前記材料から作られた装置の使用。
- 水およびポリヒドロキシル化された脂肪族炭化水素の存在下で塩化水素による腐食を防ぐ、請求項20に記載の使用。
- 前記ポリヒドロキシル化された脂肪族炭化水素がグリセリンであり、前記クロロヒドリンがジクロロプロパノールである、請求項22に記載の使用。
- (a) ポリヒドロキシル化された脂肪族炭化水素、ポリヒドロキシル化された脂肪族炭化水素のエステル、またはこれらの混合物を、塩化水素を含有する塩素化剤と反応させる部分と、
(b)塩素化剤に耐性がある材料で作られたかあるいは前記材料で被覆された装置内に作られた少なくとも1つの別の部分と、
を含む、クロロヒドリンを調製するためのプラント。 - 前記ポリヒドロキシル化された脂肪族炭化水素がグリセリンであり、前記クロロヒドリンがジクロロプロパノールである、請求項24に記載のプラント。
- グリセリンを、塩化水素を含有する塩素化剤と反応させる、ジクロロプロパノールの調製方法であって、前記方法の全ての工程を、それらの工程を行う条件下で、塩素化剤に耐性がある材料で作成されたかまたは被覆された装置内で行う、方法。
Applications Claiming Priority (21)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0505120 | 2005-05-20 | ||
EP05104321.4 | 2005-05-20 | ||
EP05104321A EP1762556A1 (en) | 2005-05-20 | 2005-05-20 | Process for producing dichloropropanol from glycerol |
FR0505120A FR2885903B1 (fr) | 2005-05-20 | 2005-05-20 | Procede de fabrication d'epichlorhydrine |
US73465705P | 2005-11-08 | 2005-11-08 | |
US73465905P | 2005-11-08 | 2005-11-08 | |
US73465805P | 2005-11-08 | 2005-11-08 | |
US73462705P | 2005-11-08 | 2005-11-08 | |
US73463705P | 2005-11-08 | 2005-11-08 | |
US73463605P | 2005-11-08 | 2005-11-08 | |
US73463505P | 2005-11-08 | 2005-11-08 | |
US73463405P | 2005-11-08 | 2005-11-08 | |
US60/734,636 | 2005-11-08 | ||
US60/734,635 | 2005-11-08 | ||
US60/734,659 | 2005-11-08 | ||
US60/734,637 | 2005-11-08 | ||
US60/734,657 | 2005-11-08 | ||
US60/734,634 | 2005-11-08 | ||
US60/734,658 | 2005-11-08 | ||
US60/734,627 | 2005-11-08 | ||
PCT/EP2006/062447 WO2006100317A1 (fr) | 2005-05-20 | 2006-05-19 | Procede de fabrication d'une chlorhydrine dans des equipements resistant a la corrosion |
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Publication Number | Publication Date |
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JP2008545642A true JP2008545642A (ja) | 2008-12-18 |
JP5419446B2 JP5419446B2 (ja) | 2014-02-19 |
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