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POST TREATMENT STEP FOR REMOVAL AND REDUCTION OF EXCESS PEROXIDE AND ACID FROM PROCESSED SULFOLANE

IP.com Disclosure Number: IPCOM000027863D
Original Publication Date: 2001-Jun-30
Included in the Prior Art Database: 2004-Apr-09
Document File: 6 page(s) / 252K

Publishing Venue

Xerox Disclosure Journal

Abstract

Disclosed is a method for the removal and reduction of hydrogen peroxide and residual acid from processed sulfolane (tetramethylene sulfone) sources. Sulfolane is a high boiling, stable, highly polar and water-soluble compound, which is an excellent co-solvent for thermal ink jet inks. Its structure is depicted in Example 1.

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XEROX DISCLOSURE JOURNAL

POST TREATMENT STEP FOR REMOVAL AND REDUCTION OF EXCESS PEROXIDE AND ACID FROM PROCESSED SULFOLANE Maura A. Sweeney
Daniel A. Foucher
Robert A. Gill
Richard L. Colt
Hiep Ly
Wiltold J. Lawrynowicz
John Gaupp
Gary R. Fague
Garland J. Nichols
Richard A. Burt
Kurt B. Gundlach
Elizabeth A. Kneisel
James L. Berryhill
Jennifer L. Thomas
Susan Deeb
Trevor Honness

Proposed Classification
U. S. C1. 106/031 Int. C1. C09d 11/02

Disclosed is a method for the removal and reduction of hydrogen peroxide and residual acid from processed sulfolane (tetramethylene sulfone) sources. Sulfolane is a high boiling, stable, highly polar and water-soluble compound, which is an excellent co- solvent for thermal ink jet inks. Its structure is depicted in Example 1.

Example 1. Sulfolane

S Sulfolene 2. Example S 0 "o n \\ 0

Processes for making sulfolane are noted in early patents by Shell Development Company and Phillips Petroleum Company. Said processes propose that sulfur dioxide and unsaturated organic compound such as 1,3-butadiene will react to produce the sulfolene

Xerox Disclosure Journal - Vol. 25, No. 3 May/June 2001 101

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POST TREATMENT STEP FOR REMOVAL AND REDUCTION OF EXCESS PEROXIDE AND ACID FROM PROCESSED SULFOLANE (Cont'd)

compound (Example 2) which may be prepared in either the presence or absence of a suitable ~olvent.~

Unprocessed sulfolane may contain discoloring and odor causing materials that can affect its quality and function.

Sulfur dioxide (SOz), one of the reactants used in the production of sulfolane, is odor causing and can act as an oxidizing or reducing agent. If incompletely removed from the reaction mixture, sulfurous acid, bisulfite and sulfite ions may result when it reacts with water. It may also induce metal corrosion when used in applications where there is contact with a metal surface.

Sulfur trioxide (SO3) may be present if the sulfur dioxide was not completely removed and the hydrogenation catalyst (such as platinum metal, vanadium pentoxide, sulfates of nickel and cobalt, the oxides of iron, tungsten, molybdenum and chromium) reacted with it. Sulfur trioxide reacts violently with water to form sulfuric acid.'

Dibutyldisulfide ([CH3(CH&]&) contributes a considerable amount of stench to the sulfolane and has been quantified in unclean and cleaned sulfolane samples.

Thiophene (Example 3) [Also known as thiofuran, thiole, thiotetrole and divinylene sulfide] has a slight aromatic odor resembling that of benzene. It is insoluble in water and miscible with most organic solvents. It can be heated .to 850T without decomposition.'

Example 3. Thiophene Example 4. Tetrahydrothiophene

S S '0 0

Tetrahydrothiophene (Example 4) [also known as tetramethylene sulfide, thia- cyclopentane and THT], is a colorless and odoriferous compound commonly used as a sensing agent in natural gas. Addition of oxidizing agents such as hydrogen peroxide will conv...