JP2010533738A - ジアルキルフェノール - Google Patents
ジアルキルフェノール Download PDFInfo
- Publication number
- JP2010533738A JP2010533738A JP2010517356A JP2010517356A JP2010533738A JP 2010533738 A JP2010533738 A JP 2010533738A JP 2010517356 A JP2010517356 A JP 2010517356A JP 2010517356 A JP2010517356 A JP 2010517356A JP 2010533738 A JP2010533738 A JP 2010533738A
- Authority
- JP
- Japan
- Prior art keywords
- methylphenol
- isopropyl
- residue
- distillation
- volatile
- 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
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 claims abstract description 30
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- 229940100630 metacresol Drugs 0.000 claims abstract description 11
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000005844 Thymol Substances 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229960000790 thymol Drugs 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 abstract description 4
- 238000005804 alkylation reaction Methods 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- NNSNIMZGXLISCO-UHFFFAOYSA-N 2,4-Diisopropyl-5-methylphenol Chemical compound CC(C)C1=CC(C(C)C)=C(O)C=C1C NNSNIMZGXLISCO-UHFFFAOYSA-N 0.000 description 2
- KEGGEHPMMDYTGB-UHFFFAOYSA-N 2,6-Diisopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(C)C(C(C)C)=C1O KEGGEHPMMDYTGB-UHFFFAOYSA-N 0.000 description 2
- ZDUIHRJGDMTBEX-UHFFFAOYSA-N 3-methyl-5-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC(O)=C1 ZDUIHRJGDMTBEX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IOAISUCAQCEHTA-UHFFFAOYSA-N 5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C)C=C1O.CC(C)C1=CC=C(C)C=C1O IOAISUCAQCEHTA-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
b)工程a)から残る残留物が次に、極めて不揮発性のまたは非揮発性の物質を除去するために蒸留され、得られた留出物が、場合によっては任意選択で5重量%以下の水を添加した後に、結晶化されるか、または
c)工程a)から残る残留物が、場合によっては任意選択で5重量%以下の水を添加した後に、結晶化させられ、結晶化した残留物が極めて不揮発性のまたは非揮発性の物質から蒸留によって分離される
ことを特徴とする、メタ−クレゾールとプロペンとの反応による4−イソプロピル−3−メチルフェノールの製造方法が見いだされた。
Claims (8)
- メタ−クレゾールをプロペンと反応させることによる4−イソプロピル−3−メチルフェノールの製造方法であって、
a)チモールおよび未反応メタ−クレゾールが反応混合物から蒸留により大部分除去され、
b)工程a)から残る残留物が次に、極めて不揮発性のまたは非揮発性の物質を除去するために蒸留され、得られた留出物が、場合によっては任意選択で5重量%以下の水を添加した添加後に、結晶化されるか、または
c)工程a)から残る残留物が、場合によっては任意選択で5重量%以下の水を添加した後に、結晶化させられ、結晶化した残留物が極めて不揮発性のまたは非揮発性の物質から蒸留によって分離される、
ことを特徴とする方法。 - 工程a)およびb)の前記蒸留が同時に実施されることを特徴とする請求項1に記載の方法。
- 工程b)またはc)による前記結晶化が−50〜80℃の温度で行われることを特徴とする請求項1または2に記載の方法。
- 工程b)からの前記留出物または工程a)からの前記残留物が水と混ぜ合わせられることを特徴とする請求項1〜3のいずれか一項に記載の方法。
- 工程b)からの前記留出物または工程a)からの前記残留物が結晶の4−イソプロピル−3−メチルフェノールと混ぜ合わせられることを特徴とする請求項1〜4のいずれか一項に記載の方法。
- 前記結晶化が冷却の結果として行われることを特徴とする請求項1〜5のいずれか一項に記載の方法。
- 前記冷却が他のインターナルを用いて冷却可能な管、管束または容器中で行われ、この装置が周囲温度と比較して冷却され、得られた結晶が、他の化合物が排出された後に、他のインターナルによって冷却可能な管、管束または容器の加熱によって溶かし出されることを特徴とする請求項6に記載の方法。
- 請求項1〜7のいずれか一項記載の方法に従って製造された4−イソプロピル−3−メチルフェノールの、抗菌または殺菌組成物の成分としての使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102007035515.9 | 2007-07-28 | ||
DE102007035515A DE102007035515A1 (de) | 2007-07-28 | 2007-07-28 | Dialkylphenole |
PCT/EP2008/059217 WO2009016028A1 (de) | 2007-07-28 | 2008-07-15 | Dialkylphenole |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010533738A true JP2010533738A (ja) | 2010-10-28 |
JP5193297B2 JP5193297B2 (ja) | 2013-05-08 |
Family
ID=39876152
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010517356A Active JP5193297B2 (ja) | 2007-07-28 | 2008-07-15 | ジアルキルフェノール |
Country Status (6)
Country | Link |
---|---|
US (1) | US8519193B2 (ja) |
EP (1) | EP2183208B1 (ja) |
JP (1) | JP5193297B2 (ja) |
BR (1) | BRPI0814074A2 (ja) |
DE (1) | DE102007035515A1 (ja) |
WO (1) | WO2009016028A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014523865A (ja) * | 2011-05-20 | 2014-09-18 | ランクセス・ドイチュランド・ゲーエムベーハー | パラ−チモールを調製するための方法 |
WO2015199202A1 (ja) * | 2014-06-27 | 2015-12-30 | 大阪化成株式会社 | 4-イソプロピル-3-メチルフェノールの製造方法 |
JP2017530181A (ja) * | 2014-10-13 | 2017-10-12 | ランクセス・ドイチュランド・ゲーエムベーハー | パラ−チモールを調製するための改良された方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102132764B (zh) * | 2011-03-02 | 2013-09-04 | 广州英赛特生物技术有限公司 | 对百里香酚及其盐或酯类衍生物在制备动物促生长饲料添加剂中的应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1886311A (en) * | 1927-07-11 | 1932-11-01 | Rheinische Kampfer Fabrik Gmbh | Process for preparing thymol |
JPS4956936A (ja) * | 1972-08-30 | 1974-06-03 | ||
JPS60139636A (ja) * | 1983-12-27 | 1985-07-24 | Kansai Coke & Chem Co Ltd | チモ−ル類を製造する方法 |
JPS60139634A (ja) * | 1983-12-27 | 1985-07-24 | Kansai Coke & Chem Co Ltd | チモ−ル類の製造法 |
JPH06247887A (ja) * | 1993-02-23 | 1994-09-06 | Nippon Tansan Kk | 針状イソプロピルメチルフェノールの製造方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB285833A (en) | 1927-02-22 | 1929-05-21 | Schering Kahlbaum Ag | Process for the manufacture of thymol |
US2468670A (en) * | 1944-01-25 | 1949-04-26 | Howards & Sons Ltd | Manufacture of thymol |
US2603662A (en) | 1947-07-03 | 1952-07-15 | Gulf Research Development Co | Process for producing substituted hydroxy aromatic compounds |
DE1265756B (de) | 1963-08-13 | 1968-04-11 | Koppers Co Inc | Verfahren zur selektiven o-Alkylierung von Phenolen |
GB1227924A (ja) | 1969-12-05 | 1971-04-15 | ||
DE2139622A1 (de) | 1971-08-07 | 1973-02-15 | Union Rheinische Braunkohlen | Verfahren zur herstellung von thymol |
US3992455A (en) * | 1973-10-01 | 1976-11-16 | Koppers Company, Inc. | Preparation of 5-sec-alkyl-m-cresol |
US4086283A (en) * | 1975-06-25 | 1978-04-25 | Bayer Aktiengesellschaft | Process for preparing thymol |
DE3824284A1 (de) * | 1988-07-16 | 1990-01-18 | Bayer Ag | Verfahren zur herstellung von thymol |
-
2007
- 2007-07-28 DE DE102007035515A patent/DE102007035515A1/de not_active Withdrawn
-
2008
- 2008-07-15 EP EP08775077.4A patent/EP2183208B1/de active Active
- 2008-07-15 BR BRPI0814074-0A2A patent/BRPI0814074A2/pt not_active IP Right Cessation
- 2008-07-15 US US12/669,976 patent/US8519193B2/en active Active
- 2008-07-15 JP JP2010517356A patent/JP5193297B2/ja active Active
- 2008-07-15 WO PCT/EP2008/059217 patent/WO2009016028A1/de active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1886311A (en) * | 1927-07-11 | 1932-11-01 | Rheinische Kampfer Fabrik Gmbh | Process for preparing thymol |
JPS4956936A (ja) * | 1972-08-30 | 1974-06-03 | ||
JPS60139636A (ja) * | 1983-12-27 | 1985-07-24 | Kansai Coke & Chem Co Ltd | チモ−ル類を製造する方法 |
JPS60139634A (ja) * | 1983-12-27 | 1985-07-24 | Kansai Coke & Chem Co Ltd | チモ−ル類の製造法 |
JPH06247887A (ja) * | 1993-02-23 | 1994-09-06 | Nippon Tansan Kk | 針状イソプロピルメチルフェノールの製造方法 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014523865A (ja) * | 2011-05-20 | 2014-09-18 | ランクセス・ドイチュランド・ゲーエムベーハー | パラ−チモールを調製するための方法 |
WO2015199202A1 (ja) * | 2014-06-27 | 2015-12-30 | 大阪化成株式会社 | 4-イソプロピル-3-メチルフェノールの製造方法 |
US10252964B2 (en) | 2014-06-27 | 2019-04-09 | Osaka Kasei Co., Ltd. | Producing method for 4-isopropyl-3-methylphenol |
JP2017530181A (ja) * | 2014-10-13 | 2017-10-12 | ランクセス・ドイチュランド・ゲーエムベーハー | パラ−チモールを調製するための改良された方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2183208B1 (de) | 2017-01-25 |
US8519193B2 (en) | 2013-08-27 |
BRPI0814074A2 (pt) | 2015-02-03 |
EP2183208A1 (de) | 2010-05-12 |
JP5193297B2 (ja) | 2013-05-08 |
DE102007035515A1 (de) | 2009-01-29 |
US20100331579A1 (en) | 2010-12-30 |
WO2009016028A1 (de) | 2009-02-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5193297B2 (ja) | ジアルキルフェノール | |
KR20080049039A (ko) | 플로르페니콜에 대한 중간체로서 유용한 옥사졸리딘 보호된아미노디올 화합물의 제조방법 | |
KR101597659B1 (ko) | 디알릴비스페놀류의 일관 제조 방법 | |
KR100877849B1 (ko) | 3-히드록시테트라히드로퓨란의 효율적 제조방법 | |
BR112020005932A2 (pt) | compostos orgânicos funcionalizados com heteroalquenil e heteroalquil halogenados e métodos para preparar tais compostos | |
KR102215078B1 (ko) | 비스페놀 a의 제조 | |
US8993813B2 (en) | Method for producing parathymol | |
US9745236B2 (en) | Method for recovering di-trimethylolpropane by distillation | |
US7183442B2 (en) | Purification method of terephthal aldehyde | |
US20060173194A1 (en) | Method for crystallizing N-vinyl-2-pyrrolidone | |
BE640931A (ja) | ||
JP3674010B2 (ja) | パラフェニレンジイソシアナートの製造方法 | |
US6160160A (en) | Process for preparing benzyl carbazates | |
Nelson | GINGEROL AND PARADOL. | |
BR112020011277B1 (pt) | Processo para a produção de carbodiimidas | |
ES2967901T3 (es) | Proceso para la purificación de una mezcla que comprende sales de n-alquil-hidroxilamonio | |
KR20140032911A (ko) | 트리아세톤아민-함유 반응 혼합물의 후처리에서 형성되는 폐수 스트림의 처리 방법 | |
JPS5829925B2 (ja) | ハロゲン化フエニルグリコ−ル類製造の際に使用された回収溶媒の精製法 | |
ES2342014T3 (es) | Proceso de purificacion de compuestos de acetal. | |
JP2005132736A (ja) | 高品位キシリレンジアミンの製造方法 | |
JP5079416B2 (ja) | 5−(3−ベンジルオキシシクロブタン)ヒダントインの製造方法 | |
ES2636691B1 (es) | Forma sólida de 4-(2-metil-1H-imidazol-1-il)-2,2-difenilbutanonitrilo | |
TW201136883A (en) | Method for producing high purity aromatic methyl alcohol and high purity aromatic methyl alcohol composition having excellent preservation stability | |
JP5178179B2 (ja) | 4−[1’,2’,3’,4’,4’a,9’a−ヘキサヒドロ−6’−ヒドロキシスピロ(シクロヘキサン−1,9’−キサンテン)−4’a−イル]レゾルシノールの製造方法 | |
CN116217390A (zh) | 一种抗氧剂3052的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120904 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121115 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130108 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130201 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5193297 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20160208 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |