GB1093737A - Improvements in and relating to the manufacture of sulpholenes and sulpholanes - Google Patents

Improvements in and relating to the manufacture of sulpholenes and sulpholanes

Info

Publication number
GB1093737A
GB1093737A GB2746365A GB2746365A GB1093737A GB 1093737 A GB1093737 A GB 1093737A GB 2746365 A GB2746365 A GB 2746365A GB 2746365 A GB2746365 A GB 2746365A GB 1093737 A GB1093737 A GB 1093737A
Authority
GB
United Kingdom
Prior art keywords
sulpholene
alkadiene
sulphur dioxide
stripping
solvent
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
GB2746365A
Inventor
John Rodriguez Blanco
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB2746365A priority Critical patent/GB1093737A/en
Priority to FR67021A priority patent/FR1484580A/en
Priority to DE19661543860 priority patent/DE1543860C3/en
Priority to NL6608892A priority patent/NL155257B/en
Priority to JP4145966A priority patent/JPS511715B1/ja
Priority to BE683203D priority patent/BE683203A/xx
Publication of GB1093737A publication Critical patent/GB1093737A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms

Landscapes

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

Abstract

Preparation of a sulpholene by reacting a 1,3-alkadiene, e.g an alkadiene containing 4 to 6 carbon atoms, with sulphur dioxide in a liquid reaction medium comprising a solvent for sulphur dioxide and the 1,3-alkadiene wherein the amount of unreacted 1,3-alkadiene and/or sulphur dioxide in the sulpholene-containing product is reduced by stripping the reaction product with the said solvent in vapour form, and the vapours resulting from the stripping are condensed and returned as a liquid condensate to the liquid reaction medium. If desired the sulpholene-containing reaction product may be subjected to conditions of pressure and elevated temperature such that a proportion of the unreacted 1,3-alkadiene and/or sulphur dioxide contained in said reaction product is flashed off as vapour therefrom prior to the above stripping step. The flashed-off vapour may be combined with the vapours resulting from the stripping. The process may be carried out in continuous or batchwise manner by reacting the sulphur dioxide and butadiene under pressure at a temperature in the range 70-120 DEG C., optionally in the presence of an anti-oxidant, using an aliphatic alcohol, preferably iso-propanol, as solvent. The reaction product is preferably stripped, with or without prior flashing off of vapour therefrom, at a temperature between 80 DEG and 90 DEG C. under slightly elevated pressure by downward passage through a vertical column having internal packing or baffles wherein vaporized solvent is supplied to the base of the column and the vapours from the head of the column together with those from the optional prior flash evaporation step are condensed for re-use. The resulting sulpholene may be catalytically hydrogenated, after an optional treatment thereof with a minor proportion of hydrogen peroxide and alkali, to give the corresponding sulpholane using, for example, Raney nickel catalyst which is added to the alcoholic solution of the sulpholene at or below the hydrogenation temperature. The preparation of 3-sulpholene and sulpholane is described.
GB2746365A 1965-06-29 1965-06-29 Improvements in and relating to the manufacture of sulpholenes and sulpholanes Expired GB1093737A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB2746365A GB1093737A (en) 1965-06-29 1965-06-29 Improvements in and relating to the manufacture of sulpholenes and sulpholanes
FR67021A FR1484580A (en) 1965-06-29 1966-06-27 Improvements in the production of sulfolenes and sulfolanes
DE19661543860 DE1543860C3 (en) 1965-06-29 1966-06-27 Process for the work-up and purification of reaction mixtures containing i-thiacyclopentene-1,1-dioxides
NL6608892A NL155257B (en) 1965-06-29 1966-06-27 PROCEDURE FOR THE REMOVAL OF UNREVERTED 1,3-ALKADIES AND / OR SULFUR DIOXIDE FROM A REACTION MIXTURE OBTAINED FROM THE PREPARATION OF SULPHOLEN.
JP4145966A JPS511715B1 (en) 1965-06-29 1966-06-27
BE683203D BE683203A (en) 1965-06-29 1966-06-27

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2746365A GB1093737A (en) 1965-06-29 1965-06-29 Improvements in and relating to the manufacture of sulpholenes and sulpholanes
GB2746366 1966-05-12

Publications (1)

Publication Number Publication Date
GB1093737A true GB1093737A (en) 1967-12-06

Family

ID=26258836

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2746365A Expired GB1093737A (en) 1965-06-29 1965-06-29 Improvements in and relating to the manufacture of sulpholenes and sulpholanes

Country Status (5)

Country Link
JP (1) JPS511715B1 (en)
BE (1) BE683203A (en)
DE (1) DE1543860C3 (en)
GB (1) GB1093737A (en)
NL (1) NL155257B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109232522A (en) * 2018-09-30 2019-01-18 辽阳辽东精细化工有限公司 Sulfolane continuous process system and technique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63121482A (en) * 1986-11-10 1988-05-25 Secoh Giken Inc Control circuit for normal and reverse rotation as well as overload stopping of motor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US30479A (en) * 1860-10-23 Carriage-wheel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109232522A (en) * 2018-09-30 2019-01-18 辽阳辽东精细化工有限公司 Sulfolane continuous process system and technique
CN109232522B (en) * 2018-09-30 2023-09-26 辽阳辽东精细化工有限公司 Sulfolane continuous production system and process

Also Published As

Publication number Publication date
JPS511715B1 (en) 1976-01-20
NL155257B (en) 1977-12-15
NL6608892A (en) 1966-12-30
DE1543860C3 (en) 1975-05-22
DE1543860A1 (en) 1970-01-02
DE1543860B2 (en) 1974-09-26
BE683203A (en) 1966-12-27

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