SA518391065B1 - عملية لإدخال الألكيل على فينولات - Google Patents
عملية لإدخال الألكيل على فينولاتInfo
- Publication number
- SA518391065B1 SA518391065B1 SA518391065A SA518391065A SA518391065B1 SA 518391065 B1 SA518391065 B1 SA 518391065B1 SA 518391065 A SA518391065 A SA 518391065A SA 518391065 A SA518391065 A SA 518391065A SA 518391065 B1 SA518391065 B1 SA 518391065B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- phenol
- isobutylene
- mixture
- catalyst
- butene
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 230000029936 alkylation Effects 0.000 title 1
- 238000005804 alkylation reaction Methods 0.000 title 1
- 150000002989 phenols Chemical class 0.000 title 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 2
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 abstract 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 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
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0214—Aryloxylates, e.g. phenolates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- 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
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
يتعلق الاختراع الحالي بعملية لتحضير 2، 6- داي -تيرت-بيوتيل فينول 2,6-di-tert-butyl phenol عن طريق تفاعل فينول phenol مع أيزو بيوتيلين isobutylene في وجود محفز فينوكسيد ألومينيوم aluminum phenoxide catalyst، تشتمل على i) تحضير محفز فينوكسيد ألومينيوم وفينول يشتمل على خليط أ) عن طريق خلط معدن ألومينيوم aluminum metal مع فينول، وتنشيط المحفز عن طريق تسخين الخليط إلى درجة حرارة 100 إلى 180 درجة مئوية، و ii) تنفيذ تفاعل ب) عن طريق تفاعل خليط أ) مع تيار stream يشتمل على أيزو بيوتيلين يشتمل على 20 إلى 90٪ بالوزن من أيزو بيوتيلين و10 إلى 80٪ بالوزن من 1- بيوتين 1-butene و/ أو 2- بيوتين 2-butene، حيث يتم تنفيذ التفاعل تحت ضغط ويكون الضغط الأقصى هو 5 إلى 20 بار.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15184850 | 2015-09-11 | ||
PCT/EP2016/071012 WO2017042181A1 (en) | 2015-09-11 | 2016-09-07 | Process for the alkylation of phenols |
Publications (1)
Publication Number | Publication Date |
---|---|
SA518391065B1 true SA518391065B1 (ar) | 2022-03-09 |
Family
ID=54146988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SA518391065A SA518391065B1 (ar) | 2015-09-11 | 2018-03-05 | عملية لإدخال الألكيل على فينولات |
Country Status (10)
Country | Link |
---|---|
US (1) | US10196334B2 (ar) |
EP (1) | EP3347336B1 (ar) |
JP (1) | JP7527757B2 (ar) |
KR (1) | KR20180053301A (ar) |
CN (1) | CN108026010A (ar) |
BR (1) | BR112018004647B1 (ar) |
SA (1) | SA518391065B1 (ar) |
TW (1) | TWI722018B (ar) |
WO (1) | WO2017042181A1 (ar) |
ZA (1) | ZA201802180B (ar) |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2353282A (en) | 1941-10-15 | 1944-07-11 | Bakelite Corp | Preparation of substituted phenols |
GB1062298A (en) | 1965-02-19 | 1967-03-22 | Ici Ltd | Process for the alkylation of phenol |
DE2039062A1 (de) | 1970-08-06 | 1972-02-10 | Hoechst Ag | Verfahren zur Herstellung von 2,6-Ditert.-butylphenol |
US3751509A (en) | 1972-07-17 | 1973-08-07 | A Liakumovich | Process for isolating isobutylene from butane-butylene fraction |
US3970708A (en) | 1974-12-26 | 1976-07-20 | Chevron Research Company | Process for removing aluminum phenoxide catalyst from phenol alkylation products |
SU783297A1 (ru) * | 1976-08-11 | 1980-11-30 | Стерлитамакский опытно-промышленный нефтехимический завод | Способ получени 2,6-ди-третбутилфенола |
US4260833A (en) | 1979-11-30 | 1981-04-07 | Uop Inc. | Preparation of alkylphenols |
JPS6052732B2 (ja) * | 1980-12-05 | 1985-11-21 | 三井化学株式会社 | 2,6−ジ−t−ブチルフエノ−ルの製造方法 |
JPS60255742A (ja) | 1984-06-01 | 1985-12-17 | Mitsui Petrochem Ind Ltd | 2、4−ジ−tert−ブチルフェノ−ルの製造方法 |
JPS6136A (ja) * | 1984-06-09 | 1986-01-06 | Maruzen Sekiyu Kagaku Kk | 2.6−ジ−tert−ブチルフエノ−ルの製造方法 |
JPS61200934A (ja) * | 1985-03-02 | 1986-09-05 | Maruzen Sekiyu Kagaku Kk | tert―ブチルフエノール類の製造方法 |
JPH0725714B2 (ja) | 1986-12-26 | 1995-03-22 | 三井石油化学工業株式会社 | 2,4―ジ―t―ブチルフェノールの製造方法 |
US4870215A (en) * | 1988-06-24 | 1989-09-26 | Ethyl Corporation | Phenol alkylation process |
CS276820B6 (cs) | 1990-05-28 | 1992-08-12 | Slovenska Technicke Univerzita | Sposob alkylácie a/alebo arylalkylácie fenolu a/alebo jeho derivátov |
JPH0812611A (ja) * | 1994-06-30 | 1996-01-16 | Dainippon Ink & Chem Inc | 2,6−ジ−アルキルフェノールの製造方法 |
CN1193007A (zh) * | 1998-01-22 | 1998-09-16 | 义县精细化工总厂 | 混合型叔丁基苯酚的合成方法 |
CN1844071A (zh) * | 2006-03-24 | 2006-10-11 | 北京极易化工有限公司 | 一种高转化率高选择性的苯酚邻位烷基化方法 |
CN1935764A (zh) * | 2006-10-20 | 2007-03-28 | 上海金海雅宝精细化工有限公司 | 一种2.6-二叔丁基苯酚烷化液的制备方法 |
CN1935763A (zh) | 2006-10-20 | 2007-03-28 | 上海金海雅宝精细化工有限公司 | 一种2.4-二叔丁基苯酚烷化液的制备方法 |
TWI570102B (zh) * | 2009-12-04 | 2017-02-11 | Si集團股份有限公司 | 從c萃餘物之物流製造三級丁基酚之方法 |
CN102976901A (zh) * | 2012-12-06 | 2013-03-20 | 锦州惠发天合化学有限公司 | 混合型叔丁基苯酚的合成方法 |
-
2016
- 2016-09-07 BR BR112018004647-7A patent/BR112018004647B1/pt active IP Right Grant
- 2016-09-07 CN CN201680052276.1A patent/CN108026010A/zh active Pending
- 2016-09-07 EP EP16766880.5A patent/EP3347336B1/en active Active
- 2016-09-07 JP JP2018513373A patent/JP7527757B2/ja active Active
- 2016-09-07 WO PCT/EP2016/071012 patent/WO2017042181A1/en active Application Filing
- 2016-09-07 US US15/758,010 patent/US10196334B2/en active Active
- 2016-09-07 KR KR1020187006572A patent/KR20180053301A/ko not_active Application Discontinuation
- 2016-09-10 TW TW105129476A patent/TWI722018B/zh active
-
2018
- 2018-03-05 SA SA518391065A patent/SA518391065B1/ar unknown
- 2018-04-04 ZA ZA2018/02180A patent/ZA201802180B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CN108026010A (zh) | 2018-05-11 |
BR112018004647A2 (pt) | 2018-09-25 |
BR112018004647B1 (pt) | 2020-12-08 |
EP3347336B1 (en) | 2019-06-12 |
JP2018526425A (ja) | 2018-09-13 |
US10196334B2 (en) | 2019-02-05 |
EP3347336A1 (en) | 2018-07-18 |
TW201718449A (zh) | 2017-06-01 |
KR20180053301A (ko) | 2018-05-21 |
TWI722018B (zh) | 2021-03-21 |
JP7527757B2 (ja) | 2024-08-05 |
US20180244595A1 (en) | 2018-08-30 |
WO2017042181A1 (en) | 2017-03-16 |
ZA201802180B (en) | 2019-06-26 |
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