JP7519398B2 - 2,2-ビス(4-ヒドロキシシクロヘキシル)プロパンの製造方法 - Google Patents
2,2-ビス(4-ヒドロキシシクロヘキシル)プロパンの製造方法 Download PDFInfo
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- JP7519398B2 JP7519398B2 JP2022062395A JP2022062395A JP7519398B2 JP 7519398 B2 JP7519398 B2 JP 7519398B2 JP 2022062395 A JP2022062395 A JP 2022062395A JP 2022062395 A JP2022062395 A JP 2022062395A JP 7519398 B2 JP7519398 B2 JP 7519398B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 43
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 title claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 85
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 77
- 239000003054 catalyst Substances 0.000 claims description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 238000005984 hydrogenation reaction Methods 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 15
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
- 239000010948 rhodium Substances 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- 229910052703 rhodium Inorganic materials 0.000 claims description 9
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005456 alcohol based solvent Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- -1 polypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
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)
- Catalysts (AREA)
Description
(実施例)
以下、本発明の実施態様を特定の具体実施例により説明するが、当業者であれば、本明細書の開示内容から本発明の利点及び効果を容易に理解できる。本発明は、他の異なる実施態様により実施又は応用することができ、本明細書における各の詳細内容も、様々な観点及び応用に基づき、本発明の開示する精神から逸脱することなく、様々な修飾や変更を付与することができる。さらに、本明細書における全ての範囲と値は、包括的で組み合わせ可能である。本明細書に列挙された範囲内の任意の数値または点、例えば、任意の整数は、サブ範囲などを導き出すための最小値または最大値として使用できる。
Claims (12)
- 2,2-ビス(4-ヒドロキシフェニル)プロパンを含む反応溶液を、85~110kg/cm2の圧力条件で、触媒を備えた反応器中で、水素ガスと水添反応を行うことにより、2,2-ビス(4-ヒドロキシシクロヘキシル)プロパンを得ることを含む、2,2-ビス(4-ヒドロキシシクロヘキシル)プロパンの製造方法であって、
前記触媒は、活性金属と、前記活性金属を担持する担体とを含み、
前記活性金属は、鉄、コバルト、ニッケル、ルテニウム、ロジウム、パラジウム、オスミウム、イリジウムおよび白金から選択される少なくとも一種であり、
前記触媒は、粉体状または顆粒状であり、
前記触媒の比表面積は、150~300m2/gであり、
前記反応溶液中の水含有量は、0.5重量%以下であり、
前記反応器は、連続反応器又はバッチ式反応器であり、
前記反応器が連続反応器である場合に、前記反応溶液を80~135℃で前記水素ガスと水添反応を行わせており、前記水素ガスの前記2,2-ビス(4-ヒドロキシフェニル)プロパンに対するモル比(前記水素ガス/前記2,2-ビス(4-ヒドロキシフェニル)プロパン)が、40~100であり、
前記反応器がバッチ式反応器である場合に、前記反応溶液を80~165℃で前記水素ガスと水添反応を行わせており、前記水素ガスの前記2,2-ビス(4-ヒドロキシフェニル)プロパンに対するモル比(前記水素ガス/前記2,2-ビス(4-ヒドロキシフェニル)プロパン)が、6~8である、製造方法。 - 前記反応溶液中の2,2-ビス(4-ヒドロキシフェニル)プロパンの含有量は2~25重量%である、請求項1に記載の製造方法。
- 前記反応溶液は、アルコール系溶媒をさらに含む、請求項1に記載の製造方法。
- 前記触媒における前記活性金属の重量比が0.1~5重量%である、請求項1に記載の製造方法。
- 前記担体が、アルミナ、シリカ及び炭素からなる群から選択される少なくとも一種である、請求項1に記載の製造方法。
- 前記触媒は顆粒状であり、また、前記触媒の粒子径は2.2~2.5mmである、請求項1に記載の製造方法。
- 前記反応器が連続反応器であり、前記連続反応器は、固定床反応器である、請求項1に記載の製造方法。
- 前記反応溶液の液空間速度は、1.12~4.48時間-1である、請求項7に記載の製造方法。
- 前記反応器がバッチ式反応器であり、前記反応溶液中の触媒の割合は1~2重量%である、請求項1に記載の製造方法。
- 前記反応器がバッチ式反応器であり、前記バッチ式反応器は、撹拌装置をさらに含み、かつ、前記撹拌装置の回転速度は一分間200~1200回転である、請求項1に記載の製造方法。
- 前記反応器がバッチ式反応器であり、前記水添反応の時間は、4~6時間である、請求項1に記載の製造方法。
- 前記水添反応の選択率は、92~99%である、請求項1に記載の製造方法。
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TW110142565A TWI841879B (zh) | 2021-11-16 | 2021-11-16 | 2,2-雙(4-羥基環己基)丙烷之製備方法 |
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JP2024021076A Pending JP2024046681A (ja) | 2021-11-16 | 2024-02-15 | 2,2-ビス(4-ヒドロキシシクロヘキシル)プロパンの製造方法 |
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Country Status (4)
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US (1) | US11905235B2 (ja) |
JP (2) | JP7519398B2 (ja) |
CN (1) | CN116135827A (ja) |
TW (1) | TWI841879B (ja) |
Citations (4)
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CN102921440A (zh) | 2012-10-26 | 2013-02-13 | 中国石油化工股份有限公司 | 一种用于制备氢化双酚a的催化剂 |
CN103706395A (zh) | 2013-12-23 | 2014-04-09 | 南京工业大学 | 一种纳米钌催化剂及应用 |
CN106563447A (zh) | 2016-10-20 | 2017-04-19 | 中国石油化工股份有限公司 | 一种用于双酚a加氢的催化剂的制备方法 |
CN112174777A (zh) | 2020-11-06 | 2021-01-05 | 本源精化环保科技有限公司 | 一种2,2’-二(4-羟基环己基)丙烷的制备方法 |
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2021
- 2021-11-16 TW TW110142565A patent/TWI841879B/zh active
- 2021-12-28 CN CN202111622107.6A patent/CN116135827A/zh active Pending
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- 2022-04-04 JP JP2022062395A patent/JP7519398B2/ja active Active
- 2022-06-14 US US17/839,762 patent/US11905235B2/en active Active
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CN102921440A (zh) | 2012-10-26 | 2013-02-13 | 中国石油化工股份有限公司 | 一种用于制备氢化双酚a的催化剂 |
CN103706395A (zh) | 2013-12-23 | 2014-04-09 | 南京工业大学 | 一种纳米钌催化剂及应用 |
CN106563447A (zh) | 2016-10-20 | 2017-04-19 | 中国石油化工股份有限公司 | 一种用于双酚a加氢的催化剂的制备方法 |
CN112174777A (zh) | 2020-11-06 | 2021-01-05 | 本源精化环保科技有限公司 | 一种2,2’-二(4-羟基环己基)丙烷的制备方法 |
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JP2023073943A (ja) | 2023-05-26 |
US11905235B2 (en) | 2024-02-20 |
TW202321188A (zh) | 2023-06-01 |
CN116135827A (zh) | 2023-05-19 |
TWI841879B (zh) | 2024-05-11 |
US20230150903A1 (en) | 2023-05-18 |
JP2024046681A (ja) | 2024-04-03 |
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