JP3930688B2 - ２，２’−メチレンビス（アルキルフェノール）類の製造方法 - Google Patents
２，２’−メチレンビス（アルキルフェノール）類の製造方法 Download PDFInfo
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- JP3930688B2 JP3930688B2 JP2001042600A JP2001042600A JP3930688B2 JP 3930688 B2 JP3930688 B2 JP 3930688B2 JP 2001042600 A JP2001042600 A JP 2001042600A JP 2001042600 A JP2001042600 A JP 2001042600A JP 3930688 B2 JP3930688 B2 JP 3930688B2
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- reaction
- methylenebis
- temperature
- alkylphenol
- range
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 10
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 title claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 40
- 239000003377 acid catalyst Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims 1
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WWVSVQGJZPSCSE-UHFFFAOYSA-N OC1=C(C)C(C)=CC(C)=C1CC1=C(C)C=C(C)C(C)=C1O Chemical compound OC1=C(C)C(C)=CC(C)=C1CC1=C(C)C=C(C)C(C)=C1O WWVSVQGJZPSCSE-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- -1 phenol compound Chemical class 0.000 description 3
- OHMOWTBZHUAFMQ-UHFFFAOYSA-N 3-ethyl-2,5-dimethylphenol Chemical compound CCC1=CC(C)=CC(O)=C1C OHMOWTBZHUAFMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- WQCKGYAPYOZTPM-UHFFFAOYSA-N 2,5-dimethyl-3-propan-2-ylphenol Chemical compound CC(C)c1cc(C)cc(O)c1C WQCKGYAPYOZTPM-UHFFFAOYSA-N 0.000 description 1
- FDJRHGOZHRZJLY-UHFFFAOYSA-N 2,5-dimethyl-3-propylphenol Chemical compound CCCc1cc(C)cc(O)c1C FDJRHGOZHRZJLY-UHFFFAOYSA-N 0.000 description 1
- ZULMMCYVCVAMIA-UHFFFAOYSA-N 2-[(2-hydroxy-3,6-dimethylphenyl)methyl]-3,6-dimethylphenol Chemical compound CC1=CC=C(C)C(CC=2C(=C(C)C=CC=2C)O)=C1O ZULMMCYVCVAMIA-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YNGDEKDDUUJFGN-UHFFFAOYSA-N 4-[(4-hydroxy-2,3,6-trimethylphenyl)methyl]-2,3,5-trimethylphenol Chemical compound CC1=CC(O)=C(C)C(C)=C1CC1=C(C)C=C(O)C(C)=C1C YNGDEKDDUUJFGN-UHFFFAOYSA-N 0.000 description 1
- MNJKRFATTCBKPH-UHFFFAOYSA-N CCC1=C(C(=C(C(=C1)C)CC2=C(C(=C(C=C2C)CC)C)O)O)C Chemical compound CCC1=C(C(=C(C(=C1)C)CC2=C(C(=C(C=C2C)CC)C)O)O)C MNJKRFATTCBKPH-UHFFFAOYSA-N 0.000 description 1
- XQEGKGPFKJQURJ-UHFFFAOYSA-N CCCC1=C(C(=C(C(=C1)C)CC2=C(C(=C(C=C2C)CCC)C)O)O)C Chemical compound CCCC1=C(C(=C(C(=C1)C)CC2=C(C(=C(C=C2C)CCC)C)O)O)C XQEGKGPFKJQURJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001042600A JP3930688B2 (ja) | 2001-02-19 | 2001-02-19 | ２，２’−メチレンビス（アルキルフェノール）類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001042600A JP3930688B2 (ja) | 2001-02-19 | 2001-02-19 | ２，２’−メチレンビス（アルキルフェノール）類の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002241331A JP2002241331A (ja) | 2002-08-28 |
| JP2002241331A5 JP2002241331A5 (enrdf_load_stackoverflow) | 2005-10-13 |
| JP3930688B2 true JP3930688B2 (ja) | 2007-06-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001042600A Expired - Fee Related JP3930688B2 (ja) | 2001-02-19 | 2001-02-19 | ２，２’−メチレンビス（アルキルフェノール）類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3930688B2 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006036685A (ja) * | 2004-07-27 | 2006-02-09 | Sumitomo Chemical Co Ltd | ビスフェノール類の製造方法 |
| JP5588130B2 (ja) * | 2009-06-29 | 2014-09-10 | 大和化成株式会社 | メチレンビス（ベンゾトリアゾリルフェノール）化合物の製造方法 |
| JP5548083B2 (ja) * | 2010-09-27 | 2014-07-16 | 昭和電工株式会社 | アリルエーテル化ノボラック型フェノール樹脂の製造方法およびその方法により得られるアリルエーテル化ノボラック型フェノール樹脂 |
| JP7167536B2 (ja) * | 2018-08-07 | 2022-11-09 | 三菱ケミカル株式会社 | ビスフェノール製造法、及びポリカーボネート樹脂の製造法 |
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2001
- 2001-02-19 JP JP2001042600A patent/JP3930688B2/ja not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| JP2002241331A (ja) | 2002-08-28 |
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