JP5040109B2 - フェノールおよび塩素の製造方法 - Google Patents
フェノールおよび塩素の製造方法 Download PDFInfo
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- JP5040109B2 JP5040109B2 JP2005361493A JP2005361493A JP5040109B2 JP 5040109 B2 JP5040109 B2 JP 5040109B2 JP 2005361493 A JP2005361493 A JP 2005361493A JP 2005361493 A JP2005361493 A JP 2005361493A JP 5040109 B2 JP5040109 B2 JP 5040109B2
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- Prior art keywords
- hydrogen chloride
- hydrochloric acid
- monochlorobenzene
- chlorine
- hydrolysis
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 48
- 229910052801 chlorine Inorganic materials 0.000 title claims description 35
- 239000000460 chlorine Substances 0.000 title claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 255
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 109
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 109
- 238000000926 separation method Methods 0.000 claims description 46
- 238000006460 hydrolysis reaction Methods 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 229910001868 water Inorganic materials 0.000 claims description 39
- 230000007062 hydrolysis Effects 0.000 claims description 36
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 35
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 33
- 238000007254 oxidation reaction Methods 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000012535 impurity Substances 0.000 claims description 11
- 238000011084 recovery Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 3
- OOOYJJANGWVIRW-UHFFFAOYSA-N chlorobenzene;phenol Chemical compound OC1=CC=CC=C1.ClC1=CC=CC=C1 OOOYJJANGWVIRW-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 28
- 239000012530 fluid Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000004821 distillation Methods 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- 150000001491 aromatic compounds Chemical class 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- -1 monocyclic aromatic compound Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003883 substance clean up Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical group CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- WBLXMRIMSGHSAC-UHFFFAOYSA-N [Cl].[Cl] Chemical compound [Cl].[Cl] WBLXMRIMSGHSAC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229930003836 cresol Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007785 strong electrolyte Substances 0.000 description 1
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Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
加水分解工程:塩素化炭化水素化合物と塩酸を接触させることにより、ヒドロキシ化合物と塩化水素を含む混合物を得る工程
塩酸分離工程:加水分解工程で得た混合物を、塩酸を主とする部分と塩素化炭化水素化合物およびヒドロキシ化合物を主とする部分に分離する工程
塩化水素分離工程:塩酸分離工程で得た塩酸を主とする部分より塩化水素を主とする部分を分離して回収し、残部を加水分解工程へリサイクルする工程
酸化工程:塩化水素分離工程で得た塩化水素を酸素と反応させて塩素と水を得る工程
塩素分離回収工程:酸化工程の反応混合物を、塩素を主とする部分、酸素を主とする部分および水と未反応塩化水素を主とする部分に分離し、酸素を主とする部分の少なくとも一部を酸化工程へリサイクルし、水と未反応塩化水素を主とする部分を加水分解工程および/または塩化水素分離工程にリサイクルする工程
ヒドロキシ化合物精製工程:塩酸分離工程で得た塩素化炭化水素化合物およびヒドロキシ化合物を主とする部分を、塩素化炭化水素化合物を主とする部分とヒドロキシ化合物を主とする部分と不純物を主とする部分に分離し、塩素化炭化水素化合物を主とする部分の少なくとも一部を加水分解工程にリサイクルする工程
塩化水素精製工程:塩化水素分離工程で得た塩化水素を主とする部分より塩素化芳香族化合物およびヒドロキシ化合物を主とする部分を分離して回収し、残りの塩化水素を酸化工程へ送る工程
<実施例1(加水分解工程 反応実施例)>
実施例1におけるモノクロルベンゼン転化率、フェノール選択率は、次の定義による。
フェノール選択率(%)=(生成したフェノールのモル数)/(反応したモノクロルベンゼンのモル数)×100
ベンゼン選択率(%)=(生成したベンゼンのモル数)/(反応したモノクロルベンゼンのモル数)×100イオン交換水40ml中に、市販の塩化銅二水和物(和光製 99.9重量%PUA)10.0gを攪拌、溶解させ塩化銅水溶液を調製した。その塩化銅水溶液中に、市販のH−ZSM−5ゼオライト(N.E.ケムキャット製 Si/Al=15 1.6mmφ押出し成型品)20.0gを添加し、スターラーにて攪拌下に8時間浸漬しイオン交換を行った。固形分をろ過、イオン交換水による水洗した後、120℃で4時間乾燥、さらに空気流通下400℃で5時間焼成し、触媒を得た。得られた触媒をアルカリ溶融/ICP−AES法にてCu含有量を測定したところ、3.0重量%であった。
B:塩酸分離工程
C:塩化水素分離工程
D:酸化工程
E:塩素分離回収工程
F:ヒドロキシ化合物精製工程
G:塩化水素精製工程
Claims (5)
- 下記の工程を含むフェノールおよび塩素の製造方法。
加水分解工程:モノクロルベンゼンと塩酸を接触させることにより、フェノールと塩化水素を含む混合物を得る工程
塩酸分離工程:加水分解工程で得た混合物を、塩酸を主とする部分とモノクロルベンゼンおよびフェノールを主とする部分に分離する工程
塩化水素分離工程:塩酸分離工程で得た塩酸を主とする部分より塩化水素を主とする部分を分離して回収し、残部を加水分解工程へリサイクルする工程
酸化工程:塩化水素分離工程で得た塩化水素を酸素と反応させて塩素と水を得る工程
塩素分離回収工程:酸化工程の反応混合物を、塩素を主とする部分、酸素を主とする部分および水と未反応塩化水素を主とする部分に分離し、酸素を主とする部分の少なくとも一部を酸化工程へリサイクルし、水と未反応塩化水素を主とする部分を加水分解工程および/または塩化水素分離工程にリサイクルする工程 - 下記の工程を含む請求項1記載の製造方法。
ヒドロキシ化合物精製工程:塩酸分離工程で得たモノクロルベンゼンおよびフェノールを主とする部分を、モノクロルベンゼンを主とする部分とフェノールを主とする部分と不純物を主とする部分に分離し、モノクロルベンゼンを主とする部分の少なくとも一部を加水分解工程にリサイクルする工程 - 下記の塩化水素精製工程を含む請求項1記載の製造方法
塩化水素精製工程:塩化水素分離工程で得た塩化水素を主とする部分よりモノクロルベンゼンおよびフェノールを主とする部分を分離して回収し、残りの塩化水素を酸化工程へ送る工程 - 塩化水素分離工程における操作圧力が0.1〜1.0MPaである請求項1記載の製造方法。
- 加水分解工程において、結晶性メタロシリケート触媒および/または金属担持結晶性メタロシリケート触媒を用いる請求項1記載の製造方法。
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JP2007161665A JP2007161665A (ja) | 2007-06-28 |
JP5040109B2 true JP5040109B2 (ja) | 2012-10-03 |
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JPS62192330A (ja) * | 1986-02-20 | 1987-08-22 | Asahi Chem Ind Co Ltd | アリ−ル水酸化物の製造法 |
JP4182608B2 (ja) * | 1999-11-10 | 2008-11-19 | 住友化学株式会社 | 塩化水素と水の分離回収方法 |
JP4011286B2 (ja) * | 1999-12-28 | 2007-11-21 | 三菱化学株式会社 | 炭酸ジアリールの製造方法 |
DE10250131A1 (de) * | 2002-10-28 | 2004-05-06 | Basf Ag | Verfahren zur Herstellung von Chlor aus Salzsäure |
JP2006131617A (ja) * | 2004-10-05 | 2006-05-25 | Sumitomo Chemical Co Ltd | ヒドロキシ化合物の製造方法 |
JP4935052B2 (ja) * | 2005-03-30 | 2012-05-23 | 住友化学株式会社 | フェノールの製造方法 |
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