JPS6029366B2 - Production method of phenol - Google Patents
Production method of phenolInfo
- Publication number
- JPS6029366B2 JPS6029366B2 JP51046683A JP4668376A JPS6029366B2 JP S6029366 B2 JPS6029366 B2 JP S6029366B2 JP 51046683 A JP51046683 A JP 51046683A JP 4668376 A JP4668376 A JP 4668376A JP S6029366 B2 JPS6029366 B2 JP S6029366B2
- Authority
- JP
- Japan
- Prior art keywords
- production method
- halogen
- isophorone
- phenyl
- aliphatic compound
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 22
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000007824 aliphatic compounds Chemical group 0.000 claims description 7
- -1 allyl halide Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は１・５・５ートリメチルシクロヘキセンー３−
オン（イソホロン）からの３・５ーキシレノール製法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 1,5,5-trimethylcyclohexene-3-
This invention relates to a method for producing 3,5-xylenol from on (isophorone).
英国特許第５８４２５６号明細書の記載から、ィソホロ
ンを６６８一６７６００の温度にて加熱することによっ
て、ィソホロンを３・５ーキシレノールに変換できるこ
とが知られている。It is known from British Patent No. 584,256 that isophorone can be converted to 3,5-xylenol by heating it at a temperature of 668-67,600°C.
しかしながら生成物の収率は比較的低い（３９％）。収
率を向上させるために種々の固体触媒を用いることも既
知である。斯くの如き触媒の例としては、英国特許第５
８８０９９号明細書に記載の活性アルミナ、および英国
特許第１１９７８０３号明細書に記載の酸化クロム（ｍ
）一酸化銅（１）混合物がある。斯くの如き固体触媒は
、変換反応中に触媒上に炭素沈着物が形成されるという
欠点を有する。このことによって触媒活性が減少し、そ
して触媒を再生するために断続的に反応を停止する必要
が生ずる。今や、或種の均一な触媒を用いて良好な収率
にてィソホロンを３・５−キシレノールに変換できると
が判明した。However, the product yield is relatively low (39%). It is also known to use various solid catalysts to improve yields. Examples of such catalysts include British Patent No.
88099 and chromium oxide (m) as described in British Patent No. 1197803.
) There is a copper monoxide (1) mixture. Such solid catalysts have the disadvantage that carbon deposits are formed on the catalyst during the conversion reaction. This reduces catalyst activity and requires intermittent reaction termination to regenerate the catalyst. It has now been found that isophorone can be converted to 3,5-xylenol in good yields using certain homogeneous catalysts.
従って本発明は、３・５ーキシレノールの製法において
、ィソホロンを４５０ｏｏ−６５０ｏｏの温度に、塩素
、臭素および沃素から選ばれたハロゲン、あるいはかか
るハロゲンを含みかつ１一６個の炭素原子を有するハロ
ゲンで置換された飽和または不飽和の脂肪族化合物、あ
るいはかかるハロゲンを含むハロゲン化フェニルの存在
下で加熱することを特徴とする製法を提供する。Therefore, the present invention provides a process for producing 3,5-xylenol in which isophorone is heated to a temperature of 450 oo to 650 oo with a halogen selected from chlorine, bromine and iodine, or a halogen containing such a halogen and having 1 to 6 carbon atoms. Provided is a production method characterized by heating in the presence of a substituted saturated or unsaturated aliphatic compound or a halogenated phenyl containing such a halogen.
脂肪族化合物およびハロゲン化フェニルは塩素、臭素お
よび沃素のいずれを含んでもよいが、好適には沃素含有
化合物である。The aliphatic compound and the phenyl halide may contain any of chlorine, bromine and iodine, but are preferably iodine-containing compounds.
脂肪族化合物の例として、ハロアルカン例えば沃化メチ
ル、臭化ｎーブチルおよび四塩化炭素、並びにハロゲン
化アリル例えば臭化アリルが挙げられる。ハロゲン化フ
ェニルの例として沃化フェニルが挙げられる。触媒の量
は、ィソホロンの重量に基づいて０．０１一２０％ｗで
あってよく、好適には０．１一５．０％ｗである。処理
は好適には５５０−６５０ｑＣの温度にて実施される。Examples of aliphatic compounds include haloalkanes such as methyl iodide, n-butyl bromide and carbon tetrachloride, and allyl halides such as allyl bromide. An example of halogenated phenyl is phenyl iodide. The amount of catalyst may be from 0.01 to 20%w, preferably from 0.1 to 5.0%w, based on the weight of isophorone. The treatment is preferably carried out at a temperature of 550-650qC.
圧力は大気圧が好都合であり、但し処理は減圧または過
圧にて実施されてもよい。１つの具体例においては、処
理は、イソホロンおよび触媒を加熱チューブ反応器に通
すことによって連続的に実施される。Conveniently the pressure is atmospheric, although the treatment may be carried out at reduced or superatmospheric pressure. In one embodiment, the treatment is carried out continuously by passing isophorone and catalyst through a heated tube reactor.
ィソホロンおよび触媒はまた、処理の選択性を改良する
ためにおよび／または反応器内の熱伝導を改良するため
に、不活性ガス例えば窒素またはアルカンと混合されて
もよい。ある条件におては、反応混合物に紫外線を照射
することが得策であることもある。Isophorone and the catalyst may also be mixed with an inert gas such as nitrogen or an alkane to improve the selectivity of the process and/or to improve heat transfer within the reactor. Under certain conditions it may be advisable to irradiate the reaction mixture with ultraviolet light.
３・５−キシレノールは、反応混合物から回収されそし
て適切な方法のいずれかによって、例えば蒸留によって
精製されてよい。3,5-xylenol may be recovered from the reaction mixture and purified by any suitable method, for example by distillation.
経済的観点かり、ハロゲンまたはハロゲン含有有機化合
物のための別個の回収段階を工程中に含めることも望ま
しい。本発明を次の例にてさらに説明する。For economic reasons, it may also be desirable to include a separate recovery step for the halogen or halogen-containing organic compound in the process. The invention is further illustrated in the following example.
例 １−１２
反応器は、全長に沿って直径５側の熱電対を備えた長さ
３２０肌および直径１仇吻のステンレススチールチュー
ブからなった。Examples 1-12 The reactor consisted of a 320 mm long and 1 mm diameter stainless steel tube with 5 mm diameter thermocouples along its length.
チューブは電気加熱オーブンによって取囲まれた。触媒
はィソホロン中に溶解され、そして混合物は一定の空間
速度にて加熱されたチューブに通された。生成物はアセ
トン中に溶解されそしてＧＬＣによって分析された。種
々の実験の結果は下記の表に示す如くであった。The tube was surrounded by an electrically heated oven. The catalyst was dissolved in isophorone and the mixture was passed through a heated tube at constant space velocity. The product was dissolved in acetone and analyzed by GLC. The results of various experiments were as shown in the table below.
数多くの実験から得られた収量の生成物を組合せ（合計
５４８．６夕）、そして減圧下に蒸留した。The product yields from the numerous experiments were combined (548.6 in total) and distilled under reduced pressure.
９９％より大の純度を有した３・５ーキシレノールが、
８５．４％の収率にて得られ、１側Ｈｇにてｂ・ｐ・９
０一９５Ｑ０であった。3,5-xylenol with a purity greater than 99%,
Obtained with a yield of 85.4%, b・p・9 with 1 side Hg
It was 0195Q0.
表
＊ 反応混合物は窒素で希釈された；モル比Ｎ２：ィソ
ホロン＝１：４ｏ＊＊ ベンゼン中の溶液として使用さ
れた（１００ｍｌ ０６日６当り９．３ｇＢｒ２）。Table * The reaction mixture was diluted with nitrogen; molar ratio N2:isophorone = 1:4o** used as a solution in benzene (9.3 g Br2 per 100 ml 06 days).
Claims (1)
を４５０℃−６５０℃の温度に、塩素、臭素および沃素
から選ばれたハロゲン、あるいはかかるハロゲンを含み
かつ１−６個の炭素原子を有するハロゲンで置換された
飽和または不飽和の脂肪族化合物、あるいはかかるハロ
ゲンを含むハロゲン化フエニルの存在下で加熱すること
を特徴とする製法。 ２ 脂肪族化合物がハロアルカンまたはハロゲン化アリ
ルである、特許請求の範囲第１項記載の製法。 ３ 脂肪族化合物またはハロゲン化フエニルが沃素含有
化合物である、特許請求の範囲第１項または第２項記載
の製法。 ４ 脂肪族化合物またはハロゲン化フエニルが沃化メチ
ルまたは沃化フエニルである、特許請求の範囲第３項記
載の製法。 ５ 使用されている触媒の量がイソホロンの重量に基づ
いて０．１−５％ｗである、特許請求の範囲第１−４項
のいずれか記載の製法。 ６ 温度が５５０℃−６５０℃である、特許請求の範囲
第１−５項のいずれか記載の製法。[Claims] 1. In the method for producing 3,5-xylenol, isophorone is heated to a temperature of 450°C to 650°C and a halogen selected from chlorine, bromine and iodine, or containing such a halogen and containing 1 to 6 carbon atoms is added. A production method characterized by heating in the presence of a saturated or unsaturated aliphatic compound substituted with a halogen atom, or a halogenated phenyl containing such a halogen. 2. The production method according to claim 1, wherein the aliphatic compound is a haloalkane or an allyl halide. 3. The production method according to claim 1 or 2, wherein the aliphatic compound or phenyl halide is an iodine-containing compound. 4. The production method according to claim 3, wherein the aliphatic compound or phenyl halide is methyl iodide or phenyl iodide. 5. Process according to any of claims 1-4, wherein the amount of catalyst used is 0.1-5%w based on the weight of isophorone. 6. The manufacturing method according to any one of claims 1 to 5, wherein the temperature is 550°C to 650°C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17533/75A GB1533983A (en) | 1975-04-28 | 1975-04-28 | Process for making 3,5-xylenol |
| GB17533/1975 | 1975-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51128927A JPS51128927A (en) | 1976-11-10 |
| JPS6029366B2 true JPS6029366B2 (en) | 1985-07-10 |
Family
ID=10096853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51046683A Expired JPS6029366B2 (en) | 1975-04-28 | 1976-04-26 | Production method of phenol |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6029366B2 (en) |
| BE (1) | BE840934A (en) |
| CH (1) | CH607988A5 (en) |
| DE (1) | DE2618213C2 (en) |
| ES (1) | ES447340A1 (en) |
| FR (1) | FR2309502A1 (en) |
| GB (1) | GB1533983A (en) |
| IT (1) | IT1063222B (en) |
| NL (1) | NL7604406A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS649362U (en) * | 1987-07-07 | 1989-01-19 | ||
| DE112019006224T5 (en) | 2019-02-28 | 2021-10-14 | Hitachi High-Tech Corporation | Electrophoresis device capable of performing electrophoresis on multiple samples independently |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE835147C (en) * | 1943-03-23 | 1952-03-27 | Bataafsche Petroleum | Process for the production of phenols |
| DE1768875B1 (en) * | 1968-07-10 | 1972-02-10 | Ruetgerswerke Ag | Process for the production of 3,5-dimethylphenol |
-
1975
- 1975-04-28 GB GB17533/75A patent/GB1533983A/en not_active Expired
-
1976
- 1976-04-21 BE BE1007337A patent/BE840934A/en not_active IP Right Cessation
- 1976-04-26 FR FR7612291A patent/FR2309502A1/en active Granted
- 1976-04-26 CH CH521676A patent/CH607988A5/en not_active IP Right Cessation
- 1976-04-26 ES ES447340A patent/ES447340A1/en not_active Expired
- 1976-04-26 JP JP51046683A patent/JPS6029366B2/en not_active Expired
- 1976-04-26 DE DE2618213A patent/DE2618213C2/en not_active Expired
- 1976-04-26 NL NL7604406A patent/NL7604406A/en not_active Application Discontinuation
- 1976-04-26 IT IT22671/76A patent/IT1063222B/en active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS649362U (en) * | 1987-07-07 | 1989-01-19 | ||
| DE112019006224T5 (en) | 2019-02-28 | 2021-10-14 | Hitachi High-Tech Corporation | Electrophoresis device capable of performing electrophoresis on multiple samples independently |
| GB2594822B (en) * | 2019-02-28 | 2022-12-07 | Hitachi High Tech Corp | Electrophoresis device capable of carrying out electrophoresis on plurality of samples independently |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2618213C2 (en) | 1985-01-24 |
| GB1533983A (en) | 1978-11-29 |
| FR2309502B1 (en) | 1979-06-22 |
| JPS51128927A (en) | 1976-11-10 |
| IT1063222B (en) | 1985-02-11 |
| DE2618213A1 (en) | 1976-11-18 |
| NL7604406A (en) | 1976-11-01 |
| CH607988A5 (en) | 1978-12-15 |
| BE840934A (en) | 1976-10-21 |
| FR2309502A1 (en) | 1976-11-26 |
| ES447340A1 (en) | 1977-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2378859A (en) | Splitting-off of hydrogen halide from halogenated hydrocarbons | |
| US3670037A (en) | Catalyst system | |
| US2504919A (en) | Preparation of olefinic compounds | |
| US4086282A (en) | Process for preparation of 3,5-xylenol | |
| KR20010102579A (en) | Method for the preparation of 1,1,1,3,3-pentafluoropropene and 1,1,1,3,3-pentafluoropropane | |
| JPS6029366B2 (en) | Production method of phenol | |
| US2327174A (en) | Preparation of halogenated olefins | |
| Sonnet et al. | Olefin inversion. 2. Sodium iodide reductions of vic-bromochlorides and vic-dichlorides | |
| US2186370A (en) | Manufacture of cyclohexene | |
| US3836592A (en) | Isomerization of 1,2-dichloro-3-butene to 1,4-dichloro-2-butene | |
| US3489816A (en) | Process for preparing allyl chloride and its monomethyl-substitution products | |
| JP2797626B2 (en) | Method for producing perfluoroalkyl bromide | |
| US1993713A (en) | Chlorination of propionic acid | |
| JPS6116255B2 (en) | ||
| US3414623A (en) | Polyamine production | |
| JPH0344061B2 (en) | ||
| US3328469A (en) | Hydration of propylene to isopropanol using cupric-cuprous halide catalyst and inorganic halide solubilizer | |
| US4166075A (en) | Method of preparing xylenes chlorinated in the nucleus | |
| US1993719A (en) | Production of tertiary-butyl chloride | |
| US4393257A (en) | Process for preparing benzotrifluoride and its derivatives | |
| US1738193A (en) | Method of making alkyl halides | |
| US2460565A (en) | Vapor phase chlorination of phthalic anhydride | |
| JPS6039048B2 (en) | Process for producing benzotrifluoride or its derivatives | |
| US3364271A (en) | Preparation of halopropadienes | |
| US3709949A (en) | Isomerization of 1,2-dichloro-3-butene to 1,4-dichloro-2-butene |