GB1289571A - - Google Patents
Info
- Publication number
- GB1289571A GB1289571A GB1289571DA GB1289571A GB 1289571 A GB1289571 A GB 1289571A GB 1289571D A GB1289571D A GB 1289571DA GB 1289571 A GB1289571 A GB 1289571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydrofurans
- tetrahydrofuran
- acetylenic
- cycloaliphatic
- cycloalkyl
- 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
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- BBLDTXFLAHKYFJ-UHFFFAOYSA-N 2,2,5,5-tetramethyloxolane Chemical compound CC1(C)CCC(C)(C)O1 BBLDTXFLAHKYFJ-UHFFFAOYSA-N 0.000 abstract 2
- -1 2,5 - disubstituted tetrahydrofurans Chemical class 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000002334 glycols Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- RFXANBCHJVECKJ-UHFFFAOYSA-N [C-]#[C-].[Bi+3].[Cu+2] Chemical compound [C-]#[C-].[Bi+3].[Cu+2] RFXANBCHJVECKJ-UHFFFAOYSA-N 0.000 abstract 1
- NPKGQBIUYHHPOT-UHFFFAOYSA-N [Cu+2].[C-]#[C-] Chemical compound [Cu+2].[C-]#[C-] NPKGQBIUYHHPOT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 150000008365 aromatic ketones Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1289571 Tetrahydrofurans ; acetylenic glycols GAF CORP 16 June 1970 [18 June 1969] 29203/70 Heading C2C Acetylenic-1,4-glycols of the formula or formula in which R is hydrogen, C 1 -C 13 alkyl, C 3 -C 8 cycloalkyl, aryl or aralkyl and R 1 and R 2 are C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, phenyl or benzyl are converted to tetrahydrofurans or the corresponding 2,5 - disubstituted tetrahydrofurans by heating a solution of the glycol with hydrogen in the presence of a hydrogenating- dehydrating catalyst consisting of palladium, ruthenium, rhodium, cobalt or nickel impregnated on a carrier having a surface area of at least 150 square metres per gram at a temperature of from 175‹ to 400‹ C. and a pressure of at least 100 p.s.i.g. Suitable solvents for the starting glycol are, for example, tetrahydrofuran, 2,5-disubstituted tetrahydrofurans, alcohols and water. Examples are given of the preparation of tetrahydrofuran and 2,2,5,5- tetramethyl-tetrahydrofuran. The acetylenic glycols used as starting materials may be prepared by reacting acetylene with (a) an excess of an aliphatic, cycloaliphatic or aromatic aldehyde in the presence of a solvent and a copper acetylide or copper-bismuth acetylide or (b) with an aliphatic, cycloaliphatic or aromatic ketone in the presence of an alkaline catalyst. Lists of suitable ketones and aldehydes are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83452969A | 1969-06-18 | 1969-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1289571A true GB1289571A (en) | 1972-09-20 |
Family
ID=25267137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1289571D Expired GB1289571A (en) | 1969-06-18 | 1970-06-16 |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE752104A (en) |
| DE (1) | DE2029557A1 (en) |
| FR (1) | FR2052648A5 (en) |
| GB (1) | GB1289571A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE31104E (en) | 1973-01-31 | 1982-12-14 | Alloy Surfaces Company, Inc. | Catalytic structure |
| FR2936803A1 (en) * | 2008-10-06 | 2010-04-09 | Arkema France | BLOCK COPOLYMER DERIVED FROM RENEWABLE MATERIALS AND METHOD FOR MANUFACTURING SUCH A BLOCK COPOLYMER. |
| WO2012095709A1 (en) * | 2011-01-12 | 2012-07-19 | Basf Se | Process for the hydrogenation of 1,4-butynediol to tetrahydrofuran in the gas phase |
| JP2019532094A (en) * | 2016-08-19 | 2019-11-07 | ニットー ベルジャム エヌヴイ | Production of TMTHF |
| CN113173894A (en) * | 2021-06-04 | 2021-07-27 | 青岛化赫医药科技有限公司 | Method for continuously synthesizing tetrahydrofuran-3-ketone |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007047018B4 (en) | 2007-10-01 | 2009-05-20 | Elmech Service Gmbh | Device for moving and transporting |
| WO2012095375A1 (en) | 2011-01-12 | 2012-07-19 | Basf Se | METHOD FOR THE HYDROGENATION OF 1,4-BUTYNEDIOL IN THE GASEOUS PHASE TO FORM MIXTURES THAT CONTAIN TETRAHYDROFURANE, 1,4-BUTANEDIOL AND γ-BUTYROLACTONE |
-
1970
- 1970-06-16 DE DE19702029557 patent/DE2029557A1/de active Pending
- 1970-06-16 FR FR7022078A patent/FR2052648A5/fr not_active Expired
- 1970-06-16 GB GB1289571D patent/GB1289571A/en not_active Expired
- 1970-06-17 BE BE752104D patent/BE752104A/en unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE31104E (en) | 1973-01-31 | 1982-12-14 | Alloy Surfaces Company, Inc. | Catalytic structure |
| FR2936803A1 (en) * | 2008-10-06 | 2010-04-09 | Arkema France | BLOCK COPOLYMER DERIVED FROM RENEWABLE MATERIALS AND METHOD FOR MANUFACTURING SUCH A BLOCK COPOLYMER. |
| WO2010040944A3 (en) * | 2008-10-06 | 2010-06-10 | Arkema France | Block copolymer derived from renewable materials and method for making such a block copolymer |
| US8231950B2 (en) | 2008-10-06 | 2012-07-31 | Arkema France | Block copolymer derived from renewable materials and method for making such block copolymer |
| EP3196226A1 (en) * | 2008-10-06 | 2017-07-26 | Arkema France | Block copolymer obtained from renewable materials and method for manufacturing such a block copolymer |
| EP3660076A1 (en) * | 2008-10-06 | 2020-06-03 | Arkema France | Block copolymer obtained from renewable materials and method for manufacturing such a block copolymer |
| WO2012095709A1 (en) * | 2011-01-12 | 2012-07-19 | Basf Se | Process for the hydrogenation of 1,4-butynediol to tetrahydrofuran in the gas phase |
| JP2019532094A (en) * | 2016-08-19 | 2019-11-07 | ニットー ベルジャム エヌヴイ | Production of TMTHF |
| US10738021B2 (en) | 2016-08-19 | 2020-08-11 | Nitto Belgium B.V. | Preparation of TMTHF |
| CN113173894A (en) * | 2021-06-04 | 2021-07-27 | 青岛化赫医药科技有限公司 | Method for continuously synthesizing tetrahydrofuran-3-ketone |
| CN113173894B (en) * | 2021-06-04 | 2022-08-02 | 上海巽田科技股份有限公司 | Method for continuously synthesizing tetrahydrofuran-3-ketone |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2029557A1 (en) | 1970-12-23 |
| FR2052648A5 (en) | 1971-04-09 |
| BE752104A (en) | 1970-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |