US3856882A
Expired / Lapsed
US
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Process for producing 2,5-dimethyl 2,4-hexadiene
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1972-09-05
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Granted: 1974-12-24
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Expires: 1992-09-05
Abstract
Abstract Process for producing 2,5-dimethyl-2,4-hexadiene by reacting isobutylene, tertiary butanol or a mixture thereof with isobutyl aldehyde in liquid phase under pressure at 110*-200*C in the presence of a catalyst, for example, a mineral acid.
Inventors
- 👤 K Takagi
- 👤 M Murakami
- 👤 K Manabe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 16:04
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07C; C07C1/00; C07C1/20; C07C1/207; C07C1/2072; C07C2/00; C07C2/86; C07C2/862; C07C2/867; C07D307/00; C07D307/02; C07D307/04; C07D307/06; C07C2527/00; C07C2527/02; C07C2527/053; C07C2527/054; C07C2527/06; C07C2527/08; C07C2527/10; C07C2527/11; C07C2527/125; C07C2527/126; C07C2527/128; C07C2527/132; C07C2527/14; C07C2527/16; C07C2527/167; C07C2531/00; C07C2531/02; C07C2531/025; Y; Y10; Y10S; Y10S585/00; Y10S585/929; Y10S585/93; Y10S585/934
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
139 words
A PROCESS FOR PRODUCING 2,5-DIMETHYL-2,4-HEXADIENE WHICH COMPRISES REACTING AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF ISOBUTYLENE AND TERTIARY BUTANOL WITH ISOBUTYL ALDEHYDE UNDER PRESSURE IN A LIQUID PHASE AT A TEMPER ATURE OF 130-180*C IN THE PRESENCE OF AT LEAST ONE CATALYST SELECTED FROM THE GROUP CONSISTING OF MINERAL ACIDS, SULFINIC ACIDS, HETEROPOLY ACIDS AND CHLORIDES, SULFATES AND PHOSPHATES OF METALS AND AMMONIA, AT A MOLAR RATIO OF ISOBUTYLENE, TERTIARY BUTANOL OR MIXTURE THEREOF TO ISOBUTYL ALDEHYDE OF 1-10, COOLING THE REACTION PRODUCT, SEPARATING THE OIL LAYER WHICH HAS FORMED AND SUCCESSIVELY DISTILLING THE OIL LAYER TO OBTAIN 2,2,5,5-TETRAMETHYL TETRAHYDROFURAN AND 2,5-DIMETHYL-2,4HEXADIENE AS SEPARATE FRACTIONS OF THE DISTILLATION, AND INCORPORATING THE FRACTION OF 2,2,5,5-TETRAMETHYL TETRAHYDROFURAN INTO THE MIXTURE OF ISOBUTYL ALDEHYDE AND AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF ISOBUTYLENE AND TERTIARY BUTANOL.
Claim 2
Dependent Claim
139 words
A PROCESS FOR PRODUCING 2,5-DIMETHYL-2,4-HEXADIENE WHICH COMPRISES REACTING AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF ISOBUTYLENE AND TERTIARY BUTANOL WITH ISOBUTYL ALDEHYDE UNDER PRESSURE IN A LIQUID PHASE AT A TEMPER ATURE OF 130-180*C IN THE PRESENCE OF AT LEAST ONE CATALYST SELECTED FROM THE GROUP CONSISTING OF MINERAL ACIDS, SULFINIC ACIDS, HETEROPOLY ACIDS AND CHLORIDES, SULFATES AND PHOSPHATES OF METALS AND AMMONIA, AT A MOLAR RATIO OF ISOBUTYLENE, TERTIARY BUTANOL OR MIXTURE THEREOF TO ISOBUTYL ALDEHYDE OF 1-10, COOLING THE REACTION PRODUCT, SEPARATING THE OIL LAYER WHICH HAS FORMED AND SUCCESSIVELY DISTILLING THE OIL LAYER TO OBTAIN 2,2,5,5-TETRAMETHYL TETRAHYDROFURAN AND 2,5-DIMETHYL-2,4HEXADIENE AS SEPARATE FRACTIONS OF THE DISTILLATION, AND INCORPORATING THE FRACTION OF 2,2,5,5-TETRAMETHYL TETRAHYDROFURAN INTO THE MIXTURE OF ISOBUTYL ALDEHYDE AND AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF ISOBUTYLENE AND TERTIARY BUTANOL.
Claim 3
Dependent Claim
34 words
A process for producing 2,5-dimethyl-2,4-hexadiene according to claim 1, wherein said catalyst is sulfuric acid, hydrochloric acid, toluenesulfonic acid, or a chloride or a sulfate or aluminum, iron, chromium, tin, antimony, bismuth or cerium.
Claim 4
Dependent Claim
52 words
A process for producing 2,5-dimethyl-2,4-hexadiene according to claim 1, wherein the heavy bottom residue remaining as a component of a boiling point higher than of 2,5-dimethyl-2,4-hexadiene after the distillation of the oil layer is decomposed in a gaseous phase at a temperature of 250* to 500*C. in the presence of dehydrating catalyst.
Claim 5
Dependent Claim
38 words
A process according to claim 1, wherein the said dehydrating catalyst is silica gel, active alumina, titanium oxide, silica alumina, synthetic zeolite, silica magnesia, silicate zirconia, titanium phosphate, zirconia phosphate, cerium phosphate or a phosphate on a carrier.
Claim 6
Dependent Claim
74 words
A process for producing 2,5-dimethyl-2,4-hexadiene according to claim 1, wherein the heavy residue obtained as a component of a boiling point higher than of 2,5-dimethyl-2,4-hexadiene after the distillation of the oil layer is decomposed in a gaseous phase at 250* to 500*C. as such or in the presence of a small amount of at least one catalyst selected from organic sulfonic acids, chlorosulfonic acid, thionyl chloride, sulfur dioxide, sulfur trioxide and boron trifluoride complexes.
Claim 7
Dependent Claim
22 words
A process according to claim 5, wherein the said catalyst is employed in an amount of from 0.01 to 5.0% by weight.
Claim 8
Dependent Claim
67 words
A process for producing 2,5-dimethyl-2,4-hexadiene according to claim 1, wherein the heavy residue obtained as a component of a boiling point higher than of 2,5-dimethyl-2,4-hexadiene after the distillation of the oil layer is decomposed in a liquid phase at 150* to 250*C. in the presence of at least one catalyst selected from mineral acids, organic sulfonic acids, boron trifluoride complexes, metallic sulfates, metallic chlorides and heteropoly acids.
Claim 9
Dependent Claim
19 words
A process according to claim 7, wherein the concentration of the said catalyst is 0.05 to 5.0% by weight.
Claim 10
Dependent Claim
16 words
A process according to claim 7, wherein an inert gas is blown into the reaction medium.
Claim 11
Dependent Claim
21 words
A process according to claim 1, wherein the reaction is carried out in a reactor made of lead or its alloy.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-23 | 1978-06-24 | 1978-12-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-23 | 1982-06-24 | 1982-12-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-23 | 1986-06-24 | 1986-12-24 | $7700.00 | Window Closed / Lapsed |