GB761613A - Preparation of tertiary-butyl-hydroquinone - Google Patents

Preparation of tertiary-butyl-hydroquinone

Info

Publication number
GB761613A
GB761613A GB2101454A GB2101454A GB761613A GB 761613 A GB761613 A GB 761613A GB 2101454 A GB2101454 A GB 2101454A GB 2101454 A GB2101454 A GB 2101454A GB 761613 A GB761613 A GB 761613A
Authority
GB
United Kingdom
Prior art keywords
hydroquinone
tert
butyl
toluene
phosphoric acid
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
Application number
GB2101454A
Inventor
Dewalt Secrist Young
George Farris Rodgers
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to GB2101454A priority Critical patent/GB761613A/en
Publication of GB761613A publication Critical patent/GB761613A/en
Expired legal-status Critical Current

Links

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
    • 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
    • C07C37/16—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 condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Tert.-butyl-hydroquinone is prepared by reacting hydroquinone with isobutylene or tert-butyl alcohol in the presence of an aromatic hydrocarbon containing 6-8 carbon atoms and phosphoric acid at an elevated temperature with agitation. The amount of phosphoric acid used is preferably from about 1 to about 6 times the weight of hydroquinone employed. The hydroquinone and tert.-butyl alcohol or isobutylene are preferably used in approximately equimolecular amounts. The aromatic hydrocarbon, usually toluene or xylene, serves to remove the mono-tert.-butyl derivative from the hydroquinone-catalyst phase and thus protect it from further alkylation. The reaction is generally conducted at reflux temperature and the water formed in the reaction when tert.-butyl alcohol is used is removed by azeotropic distillation. Tert.-butyl-hydroquinone is used for the stabilization of oils and fats. In examples, the process of the invention is carried out batchwise, in successive batches or continuously. In the batchwise process: (1) hydroquinone, toluene or xylene and phosphoric acid are mixed and heated while tert.-butyl-alcohol is added slowly, the aromatic hydrocarbon layer is separated from the acid layer (which may be re-used) and the tert.-butyl-hydroquinone obtained therefrom; (2) as in (1) but using isobutylene and xylene. In the successive batch process hydroquinone, phosphoric acid and toluene, are mixed and refluxed, tert.-butyl alcohol is added slowly (further hydroquinone being added at intervals during this addition), the toluene and acid layers are separated, the toluene layer is cooled to crystallize tert.-butyl hydroquinone and then filtered, the filtrate and the phosphoric acid being used in successive batches. In the continuous process, equal volumes of toluene and phosphoric acid are heated to boiling point in a cylindrical reactor and well stirred at the bottom (i.e. the acid layer) only, a mixture of tert.-butyl alcohol, toluene and hydroquinone is fed in at the bottom of the reactor, the toluene solution of the product being drawn off at the top of the reactor, the tert.-butyl hydroquinone separated and the toluene recycled.
GB2101454A 1954-07-19 1954-07-19 Preparation of tertiary-butyl-hydroquinone Expired GB761613A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2101454A GB761613A (en) 1954-07-19 1954-07-19 Preparation of tertiary-butyl-hydroquinone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2101454A GB761613A (en) 1954-07-19 1954-07-19 Preparation of tertiary-butyl-hydroquinone

Publications (1)

Publication Number Publication Date
GB761613A true GB761613A (en) 1956-11-14

Family

ID=10155731

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2101454A Expired GB761613A (en) 1954-07-19 1954-07-19 Preparation of tertiary-butyl-hydroquinone

Country Status (1)

Country Link
GB (1) GB761613A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2822822A1 (en) * 2001-03-30 2002-10-04 Council Scient Ind Res PROCESS FOR PREPARING DIHYDROXYBENZENE ALKYL
CN103553880A (en) * 2013-11-15 2014-02-05 天津瑞泰精细化工有限公司 Synthetic method of para-tert-butylcatechol

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2822822A1 (en) * 2001-03-30 2002-10-04 Council Scient Ind Res PROCESS FOR PREPARING DIHYDROXYBENZENE ALKYL
WO2002079130A1 (en) * 2001-03-30 2002-10-10 Council Of Scientific And Industrial Research A process for preparing alkylated dihydroxybenzene
GB2378441A (en) * 2001-03-30 2003-02-12 Council Scient Ind Res A process for preparing alkylated dihydroxybenzene
GB2378441B (en) * 2001-03-30 2004-09-22 Council Scient Ind Res A process for preparing alkylated dihydroxybenzene
US7112705B2 (en) 2001-03-30 2006-09-26 Council Of Scientific And Industrial Research Process for preparing alkylated dihydroxybenzene
CN103553880A (en) * 2013-11-15 2014-02-05 天津瑞泰精细化工有限公司 Synthetic method of para-tert-butylcatechol
CN103553880B (en) * 2013-11-15 2015-07-22 天津瑞泰精细化工有限公司 Synthetic method of para-tert-butylcatechol

Similar Documents

Publication Publication Date Title
US2212895A (en) Process for the preparation of acyl sulphides and products resulting therefrom
US2773881A (en) Glycol carbonates
US2135641A (en) Esters of c-dialkylglycines
GB761613A (en) Preparation of tertiary-butyl-hydroquinone
US2476052A (en) Ester exchange reaction
US2471274A (en) Nitroalkyl sulfites and process for preparing them
IL23259A (en) Process for preparing dihydrocarbyl antimony carboxylates and mercaptides
US2520093A (en) Manufacture of 3-dialkylamino-2-hydroxy-propyl amines
US2870192A (en) Tricresylphosphate process
US2778862A (en) Process for ethylating toluene
US3313843A (en) Preparation of cinnamate esters
US2572566A (en) Process for production of 3, 4-dihydroxytetrahydrofuran
US4323713A (en) Preparation of mono-tertiary butylhydroquinone
US2462221A (en) Process for the production of acetarylamides
US4504363A (en) Preparation of cis-2,6-dimethylmorpholine
US2585723A (en) Production of aliphatic acids
US2504732A (en) Preparation of meta-dioxanes
US3102905A (en) Process for preparing tertiary butyl acetate
US3642843A (en) Method of producing unsaturated nitrile and ester compounds
US1954433A (en) Method of preparing acid amides
US3417129A (en) Process for the manufacture of acetoacetic acid methyl ester and acetoacetic acid ethyl ester
US2277833A (en) Higher alkyl substituted phenothioxins
US2782220A (en) Condensation of di-alkyl succinates
US2005371A (en) Process for the manufacture of tripropionin
US2991311A (en) Method of alkylating amines