KR890014422A - 하이드록시메틸-디할로-디알킬페놀의 합성방법 - Google Patents
하이드록시메틸-디할로-디알킬페놀의 합성방법 Download PDFInfo
- Publication number
- KR890014422A KR890014422A KR1019890003421A KR890003421A KR890014422A KR 890014422 A KR890014422 A KR 890014422A KR 1019890003421 A KR1019890003421 A KR 1019890003421A KR 890003421 A KR890003421 A KR 890003421A KR 890014422 A KR890014422 A KR 890014422A
- Authority
- KR
- South Korea
- Prior art keywords
- dialkylphenol
- dihalo
- hydroxymethyl
- solvent
- halomethyl
- Prior art date
Links
- 238000001308 synthesis method Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- ADSOUAXTJFBPQK-UHFFFAOYSA-N 1,3-dibromo-2,4,6-trimethyl-5-phenylmethoxybenzene Chemical compound CC1=C(Br)C(C)=C(Br)C(C)=C1OCC1=CC=CC=C1 ADSOUAXTJFBPQK-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- OFKCMFHRODHIGA-UHFFFAOYSA-N 1-methyl-2h-pyrrol-3-one Chemical compound CN1CC(=O)C=C1 OFKCMFHRODHIGA-UHFFFAOYSA-N 0.000 claims 1
- NTEVJJKCRGENGX-UHFFFAOYSA-N 2,6-dimethyl-4-(tribromomethyl)phenol Chemical compound BrC(C=1C=C(C(=C(C1)C)O)C)(Br)Br NTEVJJKCRGENGX-UHFFFAOYSA-N 0.000 claims 1
- DEMXNIAFOAEFSU-UHFFFAOYSA-N 3,5-dibromo-2,4,6-trimethylphenol Chemical compound CC1=C(O)C(C)=C(Br)C(C)=C1Br DEMXNIAFOAEFSU-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- HNODKEWXOCAQFU-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(Br)Br Chemical compound C(C1=CC=CC=C1)OC(Br)Br HNODKEWXOCAQFU-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
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)
Abstract
내용 없음.
Description
내용없음
Claims (10)
- 할로메틸-디할로-디알킬페놀을, 하이드록시메틸-디할로-디알킬페놀이 생성되는 조건하에, 55℃ 미만의 온도에서 수-혼화성 유기 용매중의 실제적으로 과량의 물과 접촉시키는 단계를 포함하는, 하이드록시메틸-디할로-디알킬페놀의 합성 방법.
- 제1항에 있어서, 반응 혼합물이 할로메틸-디할로-디알킬페놀의 몰당 30몰 이상의 물을 함유하며, 용매의 양이 수성상 및 유기상의 분리를 방지하기에 충분한 방법.
- 제2항에 있어서, 반응 혼합물이 물의 몰당 0.35몰 이상의 용매를 함유하는 방법.
- 제3항에 있어서, 할로메틸-디할로-디알킬페놀 및 하이드록시메틸-디할로-디알킬페놀 상의 각각의 할로겐이 각기 독립적으로 염소 또는 브롬이며 반응 온도는 50℃이하인 방법.
- 제4항에 있어서, 할로메틸-디할로-디알킬페놀이 트리브로모메시톨이며 하이드록시메틸-디할로-디알킬페놀은 디브로모메시톨 벤질 알코올인 방법.
- 제5항에 있어서, 용매가 아세톤, THF, n-메틸피롤리논, 디메틸설폭사이드, 디옥산 또는 디메톡시에탄을 함유하는 방법.
- 제6항에 있어서, 용매가 아세톤인 방법.
- 제7항에 있어서, 공정 온도가 20℃ 이상인 방법.
- 제8항에 있어서, 최종 생성물이 10몰% 이하의 디브로모메시틸 벤질 에테르 및 8몰% 이하의 트리브로모메시톨의 아세틸 유도체를 함유하는 방법.
- 제9항에 있어서, 최종 생성물이 8몰% 이하의 디브로모메시틸 벤질 에테르 및 6몰% 이하의 트리브로모메시톨의 아세틸 유도체를 함유하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US170486 | 1988-03-21 | ||
| US07/170,486 US4849548A (en) | 1988-03-21 | 1988-03-21 | Hydrolysis of halo- and alkyl-substituted phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR890014422A true KR890014422A (ko) | 1989-10-23 |
Family
ID=22620040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890003421A KR890014422A (ko) | 1988-03-21 | 1989-03-20 | 하이드록시메틸-디할로-디알킬페놀의 합성방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4849548A (ko) |
| EP (1) | EP0334195B1 (ko) |
| JP (1) | JP2688437B2 (ko) |
| KR (1) | KR890014422A (ko) |
| AT (1) | ATE104942T1 (ko) |
| AU (1) | AU613159B2 (ko) |
| BR (1) | BR8901420A (ko) |
| CA (1) | CA1309110C (ko) |
| DE (1) | DE68914872T2 (ko) |
| MY (1) | MY103855A (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892925A (en) * | 1989-01-23 | 1990-01-09 | The Dow Chemical Company | Process for preparing phenolic hydroxyl-containing compounds from 2,6-dibromo-3,5-dialkyl-4-hydroxybenzyl ethers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1212867A (fr) * | 1957-09-27 | 1960-03-28 | Schenectady Varnish Company | Bromométhyl-méthylolphénols et procédé pour la préparation de ceux-ci |
| US4731423A (en) * | 1986-08-13 | 1988-03-15 | The Dow Chemical Company | Meta-halo-phenolic alkylation products and epoxy systems |
-
1988
- 1988-03-21 US US07/170,486 patent/US4849548A/en not_active Expired - Fee Related
-
1989
- 1989-03-13 CA CA000593496A patent/CA1309110C/en not_active Expired - Fee Related
- 1989-03-14 AU AU31278/89A patent/AU613159B2/en not_active Ceased
- 1989-03-15 AT AT8989104639T patent/ATE104942T1/de not_active IP Right Cessation
- 1989-03-15 EP EP89104639A patent/EP0334195B1/en not_active Expired - Lifetime
- 1989-03-15 DE DE68914872T patent/DE68914872T2/de not_active Expired - Fee Related
- 1989-03-18 MY MYPI89000342A patent/MY103855A/en unknown
- 1989-03-20 KR KR1019890003421A patent/KR890014422A/ko not_active Application Discontinuation
- 1989-03-20 BR BR898901420A patent/BR8901420A/pt not_active Application Discontinuation
- 1989-03-20 JP JP1066461A patent/JP2688437B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2688437B2 (ja) | 1997-12-10 |
| ATE104942T1 (de) | 1994-05-15 |
| DE68914872T2 (de) | 1994-08-11 |
| EP0334195A2 (en) | 1989-09-27 |
| US4849548A (en) | 1989-07-18 |
| EP0334195B1 (en) | 1994-04-27 |
| MY103855A (en) | 1993-09-30 |
| BR8901420A (pt) | 1989-11-14 |
| JPH01299242A (ja) | 1989-12-04 |
| CA1309110C (en) | 1992-10-20 |
| AU3127889A (en) | 1989-09-21 |
| EP0334195A3 (en) | 1991-06-12 |
| AU613159B2 (en) | 1991-07-25 |
| DE68914872D1 (de) | 1994-06-01 |
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Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19890320 |
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Patent event code: PA02012R01D Patent event date: 19940318 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19890320 Comment text: Patent Application |
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Comment text: Notification of reason for refusal Patent event date: 19960626 Patent event code: PE09021S01D |
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Patent event date: 19961127 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19960626 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |