GB1451118A - Process for the production of hydroxyalkylphenyl derivatives - Google Patents
Process for the production of hydroxyalkylphenyl derivativesInfo
- Publication number
- GB1451118A GB1451118A GB5976973A GB5976973A GB1451118A GB 1451118 A GB1451118 A GB 1451118A GB 5976973 A GB5976973 A GB 5976973A GB 5976973 A GB5976973 A GB 5976973A GB 1451118 A GB1451118 A GB 1451118A
- Authority
- GB
- United Kingdom
- Prior art keywords
- value
- inclusively
- formula
- alkali metal
- carbon atoms
- 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- -1 piperazino ring Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 239000003054 catalyst Substances 0.000 abstract 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 abstract 1
- 150000008046 alkali metal hydrides Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000006866 deterioration Effects 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000011368 organic material Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1451118 Preparation of alkylphenol derivatives CIBA-GEIGY AG 27 Dec 1973 [27 Dec 1972] 59769/73 Heading C2C Compounds of the formulµ wherein R 1 and R 2 independently of each other represent an alkyl group having from 1 to 6 carbon atoms, B 1 represents -O-(C x H 2x )-H or wherein x has a value from 6 to 30, inclusively, Y 1 represents an alkyl group having from 1 to 18 carbon atoms or a cycloalkyl group having from 3 to 12 carbon atoms and Y 2 represents hydrogen, an alkyl group having from 1 to 18 carbon atoms, or a cycloalkyl group of 5 to 12 carbon atoms, or Y 1 and Y 2 together with the nitrogen atom to which they are linked form a piperidino or piperazino ring, B 2 each represent -O- or -NH- and y has a value from 2 to 18, inclusively, and B 3 represents -O-CH 2 - and B 4 represents or wherein R 1 and R 2 are as defined above, and n is 0 to 6, or B 3 represents -NH-(CH 2 ) m -, wherein m has a value from 2 to 6, inclusively, and B 4 represents wherein p and q have values from 2 to 6, inclusively, and R 1 and R 2 are as defined above, or B 3 represents -NH-(CH 2 ) s -, wherein s has a value from 1 to 6, inclusively, and B 4 represents wherein r has a value from 1 to 6 and R 1 and R 2 are as defined above and each of z and z<SP>1</SP> have a value from 2 to 12, inclusively, are obtained by gradually adding methyl acrylate to a phenol compound of the formula wherein R 1 and R 2 are as defined above, said addition being carried out at a constant slow rate throughout the reaction, so that the overall molar ratio of methyl acrylate and the phenol is at least 1 : 1; in the presence of from 0.001 to 10 mole per cent, based on the phenol compound of Formula V, of an alkaline catalyst, an alkaline catalyst selected from alkali metal hydrides, alkali metal alkoxides of the formula wherein M is an alkali metal, and X 1 , X 2 and X 3 are H, alkyl, aryl or aralkyl groups having up to 12 C atoms, and alkali metal amides of the formula wherein X 4 and X 5 are H alkyl or aryl having up to 12 C atoms and, immediately after completion of the reaction, adding to the resultant reaction mixture a compound selected from (a) a monohydric alcohol or a monoamine of the formulµ (b) a dihydric alcohol or a diamine of the formulµ (c) a tri- or tetrahydric alcohol or a polyamine of the formulµ and (d) a thioether compound of the formula wherein Y 1 , Y 2 , x, y, z and z<SP>1</SP> are as defined above and B 3 represents -O-CH 2 - and B 4 <SP>1</SP> represents or B 3 represents -NH-(CH 2 ) m -, wherein m has the value from 2 to 6, inclusively, and B 4 <SP>11</SP> represents or or B 3 represents -NH-(CH 2 ) s -, wherein s has the value from 1 to 6 and B 4 <SP>11</SP> represents and n, o, p and v are defined as above the second reaction being carried out at 130‹ to 160‹ C. in the presence of from 0.001 to 10 mole per cent based on the phenol compound of Formula V of a second alkaline catalyst selected from the alkaline catalysts specified above, but which is different from the catalyst employed in the first step, or alkali metal hydroxides. The products may be used for the stabilization of organic materials normally subject to oxidative deterioration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31880172A | 1972-12-27 | 1972-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1451118A true GB1451118A (en) | 1976-09-29 |
Family
ID=23239623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5976973A Expired GB1451118A (en) | 1972-12-27 | 1973-12-27 | Process for the production of hydroxyalkylphenyl derivatives |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4994644A (en) |
| CA (1) | CA1005456A (en) |
| CH (1) | CH585178A5 (en) |
| DE (1) | DE2364126A1 (en) |
| FR (1) | FR2212323B1 (en) |
| GB (1) | GB1451118A (en) |
| NL (1) | NL7317619A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2231523C1 (en) * | 2002-11-28 | 2004-06-27 | ЗАО Стерлитамакский нефтехимический завод | Method for preparing pentaerythryl-tetrakis-[3-(3,5-di-tertiary-butyl-4-oxyphenyl)-propionate] |
| RU2231522C2 (en) * | 2002-07-03 | 2004-06-27 | Институт биохимической физики им. Н.М. Эмануэля РАН | Method for preparing 3-(4-hydroxy-3,5-di-tertiary-butylphenyl)-propionic acid methyl ester |
| RU2239627C2 (en) * | 2003-01-08 | 2004-11-10 | ЗАО Стерлитамакский нефтехимический завод | Method for preparing beta-(4-hydroxy-3,5-di-tertiary-butylphenyl)-propionic acid methyl ester |
| RU2257375C1 (en) * | 2004-03-23 | 2005-07-27 | Государственное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" (ГОУ ВПО УГНТУ) | METHOD FOR PREPARING β-(4-HYDROXY-3.5-DI-TERTIARY-BUTYLPHENYL)-PROPIONIC ACID ESTERS |
| RU2259995C1 (en) * | 2004-04-02 | 2005-09-10 | Государственное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" (ГОУ ВПО УГНТУ) | Method for preparing $$$-(4-hydroxy-3,5-di-tertiary-butylphenyl)propionic acid esters |
| RU2263104C1 (en) * | 2004-04-19 | 2005-10-27 | Государственное образовательное учреждение высшего профессионального образования Уфимский государственный нефтяной технический университет (ГОУ ВПО УГНТУ) | Method for preparing beta-(4-hydroxy-3,5-di-tertiary-butylphenyl)propionic acid methyl ester |
| CN111556864A (en) * | 2017-11-17 | 2020-08-18 | 弗劳恩霍弗应用研究促进协会 | Compound with stabilizing effect, preparation method of compound, composition containing stabilizing compound, method for stabilizing organic component and application of stabilizing compound |
| CN113735711A (en) * | 2021-10-12 | 2021-12-03 | 山东省临沂市三丰化工有限公司 | Novel hindered phenol antioxidant and preparation method thereof |
| CN117263821A (en) * | 2023-09-21 | 2023-12-22 | 西华大学 | A kind of monoalicyclic diamide hindered phenolic antioxidant and preparation method thereof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57197245A (en) * | 1981-05-28 | 1982-12-03 | Mitsui Petrochem Ind Ltd | Tetrakis(3-(3,5-dibutyl-4-hydroxyphenyl) propionyloxymethyl)methane |
| DE3423443A1 (en) * | 1984-06-26 | 1986-01-02 | Röhm GmbH, 6100 Darmstadt | METHOD FOR THE PRODUCTION OF ESTERS OF ACRYLIC AND METHACRYLIC ACID BY TRANSESTERATION |
| DE3639400A1 (en) * | 1986-11-18 | 1988-05-26 | Huels Chemische Werke Ag | Esters of 3-tert-butyl- or 3-tert-butyl-5-alkyl-4-hydroxyphenyl(alkane)carboxylic acids with ethoxylates of monofunctional thiophenols and thiols, process for their preparation and their use as stabilisers |
| US5206414A (en) * | 1990-01-11 | 1993-04-27 | Ciba-Geigy Corporation | Process for the preparation of hydroxyphenylpropionic acid esters |
| JP2804234B2 (en) * | 1994-11-18 | 1998-09-24 | ボン電気株式会社 | Sheet detecting device and sheet sorting device using the same |
| DE10032582A1 (en) | 2000-07-05 | 2002-01-17 | Basf Ag | Stabilizers, especially for thermoplastic polyurethanes |
| DE102005044250A1 (en) * | 2005-09-15 | 2007-03-29 | Röhm Gmbh | Process for the preparation of methacrylates with reactive double bonds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3247240A (en) * | 1962-01-05 | 1966-04-19 | Geigy Ag J R | Process for the preparation of carbonyl compounds containing a hindered phenol group |
| CH454171A (en) * | 1964-06-02 | 1968-04-15 | Geigy Ag J R | Process for the production of organic esters |
-
1973
- 1973-12-21 NL NL7317619A patent/NL7317619A/xx unknown
- 1973-12-21 FR FR7345972A patent/FR2212323B1/fr not_active Expired
- 1973-12-21 CH CH1804573A patent/CH585178A5/xx not_active IP Right Cessation
- 1973-12-21 DE DE19732364126 patent/DE2364126A1/en active Pending
- 1973-12-24 CA CA188,860A patent/CA1005456A/en not_active Expired
- 1973-12-27 GB GB5976973A patent/GB1451118A/en not_active Expired
- 1973-12-27 JP JP49004738A patent/JPS4994644A/ja active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2231522C2 (en) * | 2002-07-03 | 2004-06-27 | Институт биохимической физики им. Н.М. Эмануэля РАН | Method for preparing 3-(4-hydroxy-3,5-di-tertiary-butylphenyl)-propionic acid methyl ester |
| RU2231523C1 (en) * | 2002-11-28 | 2004-06-27 | ЗАО Стерлитамакский нефтехимический завод | Method for preparing pentaerythryl-tetrakis-[3-(3,5-di-tertiary-butyl-4-oxyphenyl)-propionate] |
| RU2239627C2 (en) * | 2003-01-08 | 2004-11-10 | ЗАО Стерлитамакский нефтехимический завод | Method for preparing beta-(4-hydroxy-3,5-di-tertiary-butylphenyl)-propionic acid methyl ester |
| RU2257375C1 (en) * | 2004-03-23 | 2005-07-27 | Государственное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" (ГОУ ВПО УГНТУ) | METHOD FOR PREPARING β-(4-HYDROXY-3.5-DI-TERTIARY-BUTYLPHENYL)-PROPIONIC ACID ESTERS |
| RU2259995C1 (en) * | 2004-04-02 | 2005-09-10 | Государственное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" (ГОУ ВПО УГНТУ) | Method for preparing $$$-(4-hydroxy-3,5-di-tertiary-butylphenyl)propionic acid esters |
| RU2263104C1 (en) * | 2004-04-19 | 2005-10-27 | Государственное образовательное учреждение высшего профессионального образования Уфимский государственный нефтяной технический университет (ГОУ ВПО УГНТУ) | Method for preparing beta-(4-hydroxy-3,5-di-tertiary-butylphenyl)propionic acid methyl ester |
| CN111556864A (en) * | 2017-11-17 | 2020-08-18 | 弗劳恩霍弗应用研究促进协会 | Compound with stabilizing effect, preparation method of compound, composition containing stabilizing compound, method for stabilizing organic component and application of stabilizing compound |
| CN111556864B (en) * | 2017-11-17 | 2022-07-08 | 弗劳恩霍弗应用研究促进协会 | Compounds with stabilizing effect, preparation method and use thereof, compositions containing same and method for stabilizing organic components |
| US11407720B2 (en) * | 2017-11-17 | 2022-08-09 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Compounds having a stabilizing effect, method for producing said compounds, composition containing said stabilizing compounds, and uses of the compounds |
| CN113735711A (en) * | 2021-10-12 | 2021-12-03 | 山东省临沂市三丰化工有限公司 | Novel hindered phenol antioxidant and preparation method thereof |
| CN117263821A (en) * | 2023-09-21 | 2023-12-22 | 西华大学 | A kind of monoalicyclic diamide hindered phenolic antioxidant and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4994644A (en) | 1974-09-09 |
| DE2364126A1 (en) | 1974-07-11 |
| NL7317619A (en) | 1974-07-01 |
| CH585178A5 (en) | 1977-02-28 |
| CA1005456A (en) | 1977-02-15 |
| FR2212323A1 (en) | 1974-07-26 |
| FR2212323B1 (en) | 1977-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |