WO1985002401A1 - PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID - Google Patents

PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID Download PDF

Info

Publication number
WO1985002401A1
WO1985002401A1 PCT/SU1983/000045 SU8300045W WO8502401A1 WO 1985002401 A1 WO1985002401 A1 WO 1985002401A1 SU 8300045 W SU8300045 W SU 8300045W WO 8502401 A1 WO8502401 A1 WO 8502401A1
Authority
WO
WIPO (PCT)
Prior art keywords
tert
butylphenol
butylphenolate
mol
τρеτ
Prior art date
Application number
PCT/SU1983/000045
Other languages
English (en)
French (fr)
Russian (ru)
Inventor
Vladimir Vladimirovich Ershov
Boris Nikolaevich Gorbunov
Alexandr Alexandrovich Volodkin
Vladimir Ivanovich Paramonov
Felix Mikhailovich Egidis
Leonid Konstantinovich Popov
Boris Iosifovich Rubinshtein
Taisia Vasilievna Pankova
Original Assignee
Institut Khimicheskoi Fiziki Akademii Nauk Sssr
Nauchno-Issledovatelsky Institut Khimikatov Dlya P
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Institut Khimicheskoi Fiziki Akademii Nauk Sssr, Nauchno-Issledovatelsky Institut Khimikatov Dlya P filed Critical Institut Khimicheskoi Fiziki Akademii Nauk Sssr
Priority to JP84502854A priority Critical patent/JPS61500548A/ja
Priority to NL8320436A priority patent/NL8320436A/nl
Priority to DE19833390557 priority patent/DE3390557C2/de
Priority to GB08516865A priority patent/GB2161162B/en
Priority to CH3302/85A priority patent/CH670634A5/de
Priority to PCT/SU1983/000045 priority patent/WO1985002401A1/ru
Priority to FI852961A priority patent/FI852961A0/fi
Publication of WO1985002401A1 publication Critical patent/WO1985002401A1/ru

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids

Definitions

  • the area of technology 5 Invention is related to organic synthesis, and moreover, to the method of emitting alkylenes ⁇ - (4- ⁇ ksy-3,5-di-pyrolithium).
  • Butylphenol with alkylakrilatom bring about a temperature of -70 -50 ° C. Below 70 ° C, the process is not recommended, since the temperature is below 70 ° C, a decrease in the speed of the reaction takes place. Above -50 ° C, there is no practical process due to the formation of side products.
  • the best option for the invention of the invention is that of the index of the image generated by the above-described image, number 2, ⁇ -da- ⁇ et.bu-typhyla-phyla-laryn.
  • the reaction can be carried out both in the current system, as well as in the closed system (autoclave).
  • autoclave In the case of the introduction of the process of interaction of 2,6-di-tré g buti-enol with an alkylacrylate in the same system (atmo- spherical pressure), a good -The reaction runs in the temperature range of 70 -50 ° C, but it is desirable to run the process because of the boiling point of the active mass.
  • the target product is distinguished by solidification in a vacuum, solidification of concrete. The space is in the technical and apparatusuric format.
  • Pteimer I 5 ⁇ ⁇ lbe equipped with a ⁇ réelletshm ⁇ ldalnik ⁇ m, a throttle body for ⁇ tb ⁇ water and an inlet for other gas, it is used in atm. -mol) hydroxide, every 250 ml of water and water temperature (88 -40 ° C) minute ⁇ and ⁇ 50 ° ⁇ . They receive a certificate of composition: hydroxide of the oxide - 0.5 wt.h. , 2, ⁇ -da- ⁇ réelle ⁇ .butylphenolate - 99 parts by weight, 2, ⁇ -di- ⁇ etg 15 butylphenol - 0.5 parts by weight. (see table).
  • ⁇ 0.43 g of the indicated composition is 9.95 g (0.048 g-mol) 2, ⁇ -di- ⁇ ret. Butylphaeol and 5 ml (0.05 ⁇ g.
  • the reaction mixture takes 2 hours, and this temperature rises from 70 to -50 ° C, 20 ° C cool to 70 ° C, neutralizes 5% sulfuric acid (3.5% sulfuric acid) butylphenyl) -pro- pyonic acid otfil'trovayut in the amount of 14, 5g (98 ot theoretical), t .pl. 64- ⁇ 5 ° C.
  • Example 2 25 ⁇ nalogichno ⁇ ime ⁇ êt I of 45g (0.2 g-mol) 4-methyl-
  • 25 atazat ⁇ which is indicated in the table, is used under the conditions of dimension I with the only difference that it heats up 2 ⁇ , 2g (0.1 g-mol) 2.4, ⁇ il- ⁇ and , 7 ⁇ g (0, 069 g-mol) of sodium hydroxide in 250 ml of xyl and after the end of the reaction, the dispenser
  • the catalyst uses an analogous model I with the only difference that after the filter it heats up to -50 ° C in a vacuum (20 mm. Further, in a ⁇ réelle ⁇ g ⁇ ly ⁇ lb they load 39.14 g (0.16 g-mol) 2,6-di- ⁇ réelle ⁇ .butshi ⁇ eya ⁇ la, 2.44 g (0.01 g-mol) of catalyst / see table / and 23 , 5 ml (0.26 g-mol) methylakrlata. The mixture heats up and withstands ⁇ and ⁇ 20 ° ⁇ for 1 hour and ⁇ and ⁇ 30 ° ⁇ for 1 hour.
  • Za ⁇ em 0 ⁇ ea ⁇ tsi ⁇ nnuyu weight ⁇ lazhdayu ⁇ d ⁇ 80 ° C and 50 ml ⁇ azbavlyayu ⁇ beyazina, benzin ⁇ vy ⁇ as ⁇ v ⁇ ⁇ b ⁇ aba ⁇ yvayu ⁇ 48 ml 3 -ya ⁇ y s ⁇ lyan ⁇ y ⁇ isl ⁇ y, ⁇ myvayu ⁇ v ⁇ d ⁇ y d ⁇ yaey ⁇ alya ⁇ y ⁇ ea ⁇ - tion, and ⁇ delyayu ⁇ u ⁇ a ⁇ ivayu ⁇ ⁇ ganichee ⁇ y sl ⁇ y, ⁇ s ⁇ a ⁇ ⁇ dve ⁇ gayu ⁇ va ⁇ uum- ⁇ e ⁇ eg ⁇ ya ⁇ e ⁇ i 20 mm ⁇ . st. with a target factor of 5, ⁇ .p. 200-204 ° C. Receives 52.9 g
  • the catalyst is similar to that of I, with the only difference that it weighs 42 g (0.02 ⁇ n ⁇ l) 2,6-di- ⁇ et. - ⁇ réelle ⁇ and ⁇ 50 ° ⁇ in a vacuum ⁇ and 20 mm ⁇ .st.
  • Example 10 (comparative). ⁇ a mixture of 9.95 g (0.048 g-mol) of 2,6-di- ⁇ et.butyl-phenol and 0.2 g of 0.0036 g-mol) of the catalyst - the hydrate ⁇ si calciferous, add 5 ml (0.056 g-mol) of methyl - ⁇ a and after the reaction in the conditions of experience I with ⁇ - the next ⁇ van ⁇ em in the vacuum will give 1.77 g (12 $ ⁇ theoret ⁇ chestogo) met ⁇ lo ⁇ - ⁇ ⁇ nic acid, litis. ⁇ pub. 64-65 ° ⁇ . - nine -
  • SHOSTAV KATALIZATORA ⁇ number - ⁇ * kata - ⁇ ⁇ ⁇ ⁇ ⁇ more range 2, 6 ⁇ 6-di- ⁇ niyu ⁇ 2.6-s click- ⁇ et. bu- - ⁇ réelle ⁇ .— -di- ⁇ réelle .- another methyl- butyl- butyl- butyl- phin. weight h l ⁇ chn ⁇ g ⁇ weight.h. metal, parts by weight
  • al- ilic acid ⁇ efir ⁇ - (4-oxy-3,5-di-toret.butylphenyl) -propo- ionic acid produces the whole yield n ⁇ g ⁇ ⁇ e ⁇ aniya ⁇ ea ⁇ tsii, snizi ⁇ ⁇ as ⁇ d ⁇ a ⁇ aliza ⁇ a 2.5 ⁇ aza, s ⁇ a ⁇ i ⁇ v ⁇ emya ⁇ ea ⁇ tsii 1.5-4 ⁇ aza, ch ⁇ ⁇ zv ⁇ lyae ⁇ in ⁇ ensi ⁇ itsi ⁇ va ⁇ ⁇ tsess and umenydi ⁇ nezhe- la ⁇ elnuyu ⁇ lime ⁇ izatsiyu al ⁇ ila ⁇ ila ⁇ a, u ⁇ s ⁇ i ⁇ ⁇ e ⁇ - n ⁇ l ⁇ giches ⁇ y ⁇ tsess on account v ⁇ zm ⁇ zhn ⁇ s ⁇ i is ⁇ lyucheniya ⁇ as ⁇ -
  • the proposed range causes the emission of alkaline ephi U - (4-oxy-Z, 5-di-toret.butylphenyl) -propionic acid, an - 10 - in the case of polymer materials and in the synthesis of thermo-stabilizers of polylephins, polyamides and other polymers.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
PCT/SU1983/000045 1983-12-01 1983-12-01 PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID WO1985002401A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP84502854A JPS61500548A (ja) 1983-12-01 1983-12-01 β−(4−ヒドロキシ−3,5−ジ−第三級ブチルフェニル)プロピオン酸アルキルエステルの製法
NL8320436A NL8320436A (nl) 1983-12-01 1983-12-01 Werkwijze voor de bereiding van beta -(4-hydroxy 3,5-di-tert.butylfenyl) propionzure alkylesters.
DE19833390557 DE3390557C2 (de) 1983-12-01 1983-12-01 Verfahren zur Herstellung von beta-(4-Hydroxy-3,5-di-tert.-butylphenyl)-propions{urealkylestern
GB08516865A GB2161162B (en) 1983-12-01 1983-12-01 Process for obtaining alkyl ethers of b-(4-oxy-3 5-di-tert butylphenyl)-propionic acid
CH3302/85A CH670634A5 (enrdf_load_stackoverflow) 1983-12-01 1983-12-01
PCT/SU1983/000045 WO1985002401A1 (en) 1983-12-01 1983-12-01 PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID
FI852961A FI852961A0 (fi) 1983-12-01 1983-12-01 Foerfarande foer framstaellning av alkylestrar av -(4-hydroxi-3,5-di-tert.butylfenyl)-propionsyra.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/SU1983/000045 WO1985002401A1 (en) 1983-12-01 1983-12-01 PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID

Publications (1)

Publication Number Publication Date
WO1985002401A1 true WO1985002401A1 (en) 1985-06-06

Family

ID=21616822

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1983/000045 WO1985002401A1 (en) 1983-12-01 1983-12-01 PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID

Country Status (7)

Country Link
JP (1) JPS61500548A (enrdf_load_stackoverflow)
CH (1) CH670634A5 (enrdf_load_stackoverflow)
DE (1) DE3390557C2 (enrdf_load_stackoverflow)
FI (1) FI852961A0 (enrdf_load_stackoverflow)
GB (1) GB2161162B (enrdf_load_stackoverflow)
NL (1) NL8320436A (enrdf_load_stackoverflow)
WO (1) WO1985002401A1 (enrdf_load_stackoverflow)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR910016673A (ko) * 1990-03-30 1991-11-05 베르너 발데크 히드록시페닐프로피오네이트의 제조방법
US5264612A (en) * 1992-09-28 1993-11-23 Himont Incorporated Process for the preparation of aryl-substituted propionic acid esters
US7667066B2 (en) 2004-02-27 2010-02-23 Albemarle Corporation Preparation of sterically hindered hydroxyphenylcarboxylic acid esters
CN102060705A (zh) * 2010-11-24 2011-05-18 上海华谊(集团)公司 一种β-(3,5-叔丁基-4-羟基)丙酸甲酯的合成方法
CN104387274A (zh) * 2014-11-21 2015-03-04 黄峰 一种β-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的生产工艺
CN107459443A (zh) * 2017-09-25 2017-12-12 甘肃省化工研究院 一种2,6‑二叔丁基酚盐的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2745882A (en) * 1953-02-05 1956-05-15 Exxon Research Engineering Co Dehydrative distillation for preparation of alkali metal salts of 2, 4, 6-trialkylphenols
US3330859A (en) * 1961-10-30 1967-07-11 Geigy Chem Corp Alkyl esters of carboxylic acids containing an alkylhydroxyphenyl group
US3364250A (en) * 1965-10-22 1968-01-16 Geigy Chem Corp Methyl beta-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate
JPS56161350A (en) * 1980-05-16 1981-12-11 Sumitomo Chem Co Ltd Preparation of phenol

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2745882A (en) * 1953-02-05 1956-05-15 Exxon Research Engineering Co Dehydrative distillation for preparation of alkali metal salts of 2, 4, 6-trialkylphenols
US3330859A (en) * 1961-10-30 1967-07-11 Geigy Chem Corp Alkyl esters of carboxylic acids containing an alkylhydroxyphenyl group
US3364250A (en) * 1965-10-22 1968-01-16 Geigy Chem Corp Methyl beta-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate
JPS56161350A (en) * 1980-05-16 1981-12-11 Sumitomo Chem Co Ltd Preparation of phenol

Also Published As

Publication number Publication date
FI852961L (fi) 1985-07-31
DE3390557T1 (de) 1985-11-14
FI852961A7 (fi) 1985-07-31
CH670634A5 (enrdf_load_stackoverflow) 1989-06-30
GB2161162B (en) 1987-12-31
DE3390557C2 (de) 1989-02-16
NL8320436A (nl) 1985-10-01
GB8516865D0 (en) 1985-08-07
JPS61500548A (ja) 1986-03-27
GB2161162A (en) 1986-01-08
FI852961A0 (fi) 1985-07-31

Similar Documents

Publication Publication Date Title
JPH08502960A (ja) 不飽和樹脂酸類とそのエステル類の酸化開裂によるカルボン酸類とそのエステル類の製造法
Savoia et al. Potassium-graphite as a metalation reagent. Synthesis of aldehydes and ketones by alkylation of imines and dihydro-1, 3-oxazine
WO1985002401A1 (en) PROCESS FOR OBTAINING ALKYL ETHERS OF alpha-(4-OXY-3,5-DI-TERT. BUTYLPHENYL)-PROPIONIC ACID
NO300321B1 (no) Fremgangsmåte for fremstilling av karboksylsyrer eller estere av disse ved oksidativ spaltning av umettede fettsyrer eller fettsyreestere
JP2664393B2 (ja) コハク酸tert―アルキルエステルの製造方法
US4055721A (en) Method of producing unsaturated carbonyl compounds
Bly et al. π-Electron Participation in the Acetolysis of β-(syn-7-Norbornenyl) ethyl p-Bromobenzenesulfonate
Rosenthal et al. Carboxylation of propargyl alcohol
US4645858A (en) Pentanedioic acid derivatives
SU1225480A3 (ru) Способ получени этилидендиацетата
US2816921A (en) Production of alpha-alkoxy alkanoic acids
US5502226A (en) Process of preparing ω-hydroxy acids
JPH0739368B2 (ja) 20,20,20−トリフルオロアラキドン酸誘導体およびその製造法
US3666838A (en) Propenyl and propadienylphosphonic acids 2-propadienyl-4-oxo-1,3-dioxa-2-phosphanaphthalene-2-oxide
JPS6319496B2 (enrdf_load_stackoverflow)
US3644502A (en) Prostaglandin synthesis
US3749744A (en) Oxo-substituted alpha,beta-unsaturated alkylated fatty acids and esters
Reed et al. The Mercury (II) Catalyzed, One-Pot Oxidation of Terminal Alkynes by Sodium Perborate in Acetic Acid
EP0301112B1 (en) Method for producing a 5-bromo-1-pentanal compound or an acetal derivative thereof
US3238237A (en) Method of producing trialkoxy aluminum compounds
US3989744A (en) 11-Substitute d-11-desoxy-pge analogues
US5569780A (en) Dialkyl 2-haloethyl malonates
Ravid et al. Synthesis in Jasmone Series. IV. Preparation of Methyl‐2‐Oxo‐5‐Pentylcyclopentyl‐1‐Acetate and its 4‐Pentyl Analogue
US2840612A (en) Method of preparing 3-ethoxy-4-hexenal
CA1249268A (en) Pentanedioic acid derivatives

Legal Events

Date Code Title Description
AK Designated states

Designated state(s): CH DE FI GB JP NL

WWE Wipo information: entry into national phase

Ref document number: 852961

Country of ref document: FI

RET De translation (de og part 6b)

Ref document number: 3390557

Country of ref document: DE

Date of ref document: 19851114

WWE Wipo information: entry into national phase

Ref document number: 3390557

Country of ref document: DE