KR960034152A - 치환 시클로헥사논의 제조방법 - Google Patents
치환 시클로헥사논의 제조방법 Download PDFInfo
- Publication number
- KR960034152A KR960034152A KR1019960005675A KR19960005675A KR960034152A KR 960034152 A KR960034152 A KR 960034152A KR 1019960005675 A KR1019960005675 A KR 1019960005675A KR 19960005675 A KR19960005675 A KR 19960005675A KR 960034152 A KR960034152 A KR 960034152A
- Authority
- KR
- South Korea
- Prior art keywords
- bar
- process according
- hydrogenation reaction
- alkyl
- general formula
- Prior art date
Links
- JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 title abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000654 additive Substances 0.000 claims abstract 2
- 230000000996 additive effect Effects 0.000 claims abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 2
- 150000001340 alkali metals Chemical class 0.000 claims abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 6
- 238000005984 hydrogenation reaction Methods 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229910021538 borax Inorganic materials 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000004328 sodium tetraborate Substances 0.000 claims 1
- 235000010339 sodium tetraborate Nutrition 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- -1 aluminum compound Chemical class 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/006—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenation of aromatic hydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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)
Abstract
하기 일반식(Ⅰ)의 치환 시클로헥사논은 하기 일반식(Ⅱ)의 페놀의 촉매화 수소화 반응에 의해서 얻어질 수 있다.
상기 반응식에서 R1내지 R5는 발명의 상세한 설명란에 정의되어 있다.
상기 반응은 20 내지 250℃, 1 내지 200바, 그리고 에테르 용매 중에서 수행된다. 필요하다면 알칼리성인 알칼리 금속, 알칼리토 금속 또는 알모늄 화합물이 첨가제로 사용될 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 수소화 반응이 에테르 용매로 하여, 지지체상에 도포된 것일 수도 있는 원소 주기율표(멘델레예프)의 ⅧB족 금속들 중에서 선택된 촉매의 존재하에서, 그리고 경우에 따라서는 알칼리성인 알칼리 금속, 알칼리토금속 또는 암모늄염 중에서 선택된 1종 이상의 추가 첨가제의 존재 하에서 이루어지는 것을 특징으로 하는, 하기 일반식(Ⅱ)의 치환 페놀의 불균질하게 촉매화된 수소화 반응에 의한 하기 일반식(Ⅰ)의 치환 시클로헥사논의 제조 방법.상기 식에서, R1, R2, R3, R4및 R5는 서로 독립적으로 수소, C1-C4알킬, C3-C8시클로알킬, 할로겐, 히드록시, C1-C4알콕시, C3-C8시클로알콕시, C1-C4알킬아미노, N(C1-C4알킬)2, -NH-C1-C4아실, COOH, COO-C1-C4알킬 또는 -CH2-Q(여기서, Q는 히드록시, C1-C4알콕시 또는 NH-C1-C4아실을 나타냄)이며, 수소가 아닌 치환기가 하나 이상이다.
- 제1항에 있어서, 수소화 반응이 디에틸렌 글리콜 디메틸 에테르, 에틸렌 글리콜 디메틸 에테르, 1.4-디옥산, 테트라히드로푸란 또는 이들 중 복수개의 혼합물 중에서 이루어지는 것을 특징으로 하는 방법.
- 제1항에 있어서, 출발 물질로서 히드로퀴논, 4-메톡시페놀 또는 p-아실아미노페놀이 사용되는 것을 특징으로 하는 방법.
- 제1항에 있어서, 수소화 반응이 20℃ 내지 250℃, 바람직하게는 60℃ 내지 230℃, 특히 바람직하게는 100℃ 내지 210℃의 온도 범위에서 이루어지는 것을 특징으로 하는 방법.
- 제1항에 있어서, 수소화 반응이 1바(bar) 내지 200바, 바람직하게는 2바 내지 150바, 특히 바람직하게는 3바 내지 100바의 압력 범위에서 이루어지는 것을 특징으로 하는 방법.
- 제1항에 있어서, 사용되는 촉매가 지지체, 바람직하게는 활성 탄소상에 도포된 팔라듐인 것을 특징으로 하는 방법.
- 제1항에 있어서, 사용되는 첨가제가 탄산나트륨 또는 보락스인 것을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19507752.0 | 1995-03-06 | ||
DE19507752A DE19507752A1 (de) | 1995-03-06 | 1995-03-06 | Verfahren zur Herstellung von substituierten Cyclohexanonen |
Publications (1)
Publication Number | Publication Date |
---|---|
KR960034152A true KR960034152A (ko) | 1996-10-22 |
Family
ID=7755748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960005675A KR960034152A (ko) | 1995-03-06 | 1996-03-05 | 치환 시클로헥사논의 제조방법 |
Country Status (12)
Country | Link |
---|---|
US (1) | US5886232A (ko) |
EP (1) | EP0731075B1 (ko) |
JP (1) | JPH08259492A (ko) |
KR (1) | KR960034152A (ko) |
CN (1) | CN1137513A (ko) |
AT (1) | ATE187428T1 (ko) |
CA (1) | CA2170823A1 (ko) |
CZ (1) | CZ66696A3 (ko) |
DE (2) | DE19507752A1 (ko) |
ES (1) | ES2141406T3 (ko) |
HU (1) | HUP9600550A3 (ko) |
TW (1) | TW320630B (ko) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19727710A1 (de) * | 1997-06-30 | 1999-01-07 | Bayer Ag | Verfahren zur Herstellung von Cyclohexanonen durch Hydrierung der entsprechenden Phenole (II.) |
DE19727712A1 (de) * | 1997-06-30 | 1999-01-07 | Bayer Ag | Verfahren zur Herstellung von Cyclohexanonen durch Hydrierung der entsprechenden Phenole (l.) |
DE59803057D1 (de) * | 1997-11-03 | 2002-03-21 | Merck Patent Gmbh | Verfahren zur Herstellung von Cyclohexanonen |
ATE366235T1 (de) * | 2001-04-06 | 2007-07-15 | Merck Patent Gmbh | Cycloalkanon-derivate |
EP2607344A1 (de) | 2011-12-24 | 2013-06-26 | Allessa Chemie GmbH | Verfahren zur Herstellung von cyclischen Ketonen |
CN103073401B (zh) * | 2013-01-25 | 2015-07-15 | 湖南化工研究院 | 对甲氧基环己酮的制备方法 |
US9981896B2 (en) | 2016-07-01 | 2018-05-29 | Res Usa, Llc | Conversion of methane to dimethyl ether |
US9938217B2 (en) | 2016-07-01 | 2018-04-10 | Res Usa, Llc | Fluidized bed membrane reactor |
WO2018004993A1 (en) | 2016-07-01 | 2018-01-04 | Res Usa, Llc | Reduction of greenhouse gas emission |
EP3504177B1 (en) * | 2016-08-26 | 2021-07-21 | Srf Limited | Process for the preparation of cyclic ketones |
CN108409547A (zh) * | 2018-04-28 | 2018-08-17 | 连云港市工业投资集团利海化工有限公司 | 对甲氧基环己酮的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3124614A (en) * | 1964-03-10 | Preparation of z-substituteb | ||
US2829166A (en) * | 1933-04-04 | 1958-04-01 | Allied Chem & Dye Corp | Hydrogenation of phenol |
CH189403A (de) * | 1935-05-28 | 1937-02-28 | Chem Ind Basel | Verfahren zur Darstellung eines hydroaromatischen Aminoalkohols. |
US3193584A (en) * | 1961-04-14 | 1965-07-06 | Engelhard Ind Inc | Hydrogenation of hydroxy aromatics and alkoxy aromatics with ruthenium catalyst |
US3965180A (en) * | 1971-11-01 | 1976-06-22 | The Upjohn Company | 4'-Fluoro-4-{[4-(phenyl)-4-alkoxy-cyclo-hexyl]amino}butyrophenones and the salts thereof |
CA1109855A (en) * | 1976-11-24 | 1981-09-29 | Jan F. Van Peppen | Production of cyclohexanone |
DE2909780A1 (de) * | 1979-03-13 | 1980-09-18 | Heraeus Gmbh W C | Verfahren zur hydrierung von p-tert.- amylphenol |
US4503273A (en) * | 1982-09-29 | 1985-03-05 | Phillips Petroleum Company | Hydrogenation of phenols |
EP0186087B1 (de) * | 1984-12-22 | 1989-08-23 | Dr. Karl Thomae GmbH | Tetrahydro-benzthiazole, deren Herstellung und deren Verwendung als Zwischenprodukte oder als Arnzneimittel |
-
1995
- 1995-03-06 DE DE19507752A patent/DE19507752A1/de not_active Withdrawn
-
1996
- 1996-01-31 TW TW085101161A patent/TW320630B/zh active
- 1996-02-22 DE DE59603823T patent/DE59603823D1/de not_active Expired - Fee Related
- 1996-02-22 AT AT96102652T patent/ATE187428T1/de not_active IP Right Cessation
- 1996-02-22 ES ES96102652T patent/ES2141406T3/es not_active Expired - Lifetime
- 1996-02-22 EP EP96102652A patent/EP0731075B1/de not_active Expired - Lifetime
- 1996-02-29 US US08/608,651 patent/US5886232A/en not_active Expired - Fee Related
- 1996-03-01 CA CA002170823A patent/CA2170823A1/en not_active Abandoned
- 1996-03-04 JP JP8070880A patent/JPH08259492A/ja active Pending
- 1996-03-05 HU HU9600550A patent/HUP9600550A3/hu unknown
- 1996-03-05 CZ CZ96666A patent/CZ66696A3/cs unknown
- 1996-03-05 KR KR1019960005675A patent/KR960034152A/ko not_active Application Discontinuation
- 1996-03-06 CN CN96104110A patent/CN1137513A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
DE59603823D1 (de) | 2000-01-13 |
CN1137513A (zh) | 1996-12-11 |
ATE187428T1 (de) | 1999-12-15 |
CA2170823A1 (en) | 1996-09-07 |
TW320630B (ko) | 1997-11-21 |
US5886232A (en) | 1999-03-23 |
DE19507752A1 (de) | 1996-09-12 |
EP0731075A1 (de) | 1996-09-11 |
CZ66696A3 (en) | 1996-09-11 |
HUP9600550A3 (en) | 1999-03-01 |
HUP9600550A2 (en) | 1997-05-28 |
JPH08259492A (ja) | 1996-10-08 |
ES2141406T3 (es) | 2000-03-16 |
EP0731075B1 (de) | 1999-12-08 |
HU9600550D0 (en) | 1996-04-29 |
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