IT1022545B - Ethynyl carbinol prepn. from unsatd. ketones - pref. methyl vinyl ketone, by ethynylation with magnesium acetylene complex in liq. ammonia - Google Patents
Ethynyl carbinol prepn. from unsatd. ketones - pref. methyl vinyl ketone, by ethynylation with magnesium acetylene complex in liq. ammoniaInfo
- Publication number
- IT1022545B IT1022545B IT2798174A IT2798174A IT1022545B IT 1022545 B IT1022545 B IT 1022545B IT 2798174 A IT2798174 A IT 2798174A IT 2798174 A IT2798174 A IT 2798174A IT 1022545 B IT1022545 B IT 1022545B
- Authority
- IT
- Italy
- Prior art keywords
- pref
- liq
- acetylide
- ethynylation
- prepn
- Prior art date
Links
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 title 2
- ABIBCFTYJDONHE-UHFFFAOYSA-N [Mg].C#C Chemical group [Mg].C#C ABIBCFTYJDONHE-UHFFFAOYSA-N 0.000 title 1
- 229910021529 ammonia Inorganic materials 0.000 title 1
- 150000002576 ketones Chemical class 0.000 title 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 abstract 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Prepn. of ethynyl carbinols of formula R1R2C=CR-C(OH)-(-C=CH)R3 (I) (where R,R1 and R3 are H, lower alkyl or lower alkenyl, R2 is H or 1-18C hydrocarbyl, or R1 and R2 together with the C atom, to which they are attached, denote cyclo-lower alkyl or cyclo-lower alkenyl) take place by reacting a cpd. R1R2C=CR-CR3O (II) pref. Me vinyl ketone in liq. NH3 with an Mg acetylene complex (III) as ethynylation reagent pref. used as a mixt. contg. >5 (5-95) esp. 10-80 wt. % (III) and Na acetylide. (I) are obtd. in high yields, e.g. 70 wt. % (compared with 30% when using Na acetylide as ethynylation reagent) and improved purity e.g. 94%. Ethynylation reagent is pref. prepd. by mixing Na acetylide with MgSO4, MgCl2, MgF2 or an organo Mg halide esp, EtMgBr, in liq. NH3, under anhydrous conditions. Pref. mixt. contains 10-95 wt. % Na acetylide w.r.t. Mg cpd. + Na acetylide. (IIIe be prepd. by reacting C2H2 with Mg in liq. NH3 in presence of Na amide or Na metal at -100 to +100 degrees C under 15-1000 psia.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40254473A | 1973-10-01 | 1973-10-01 | |
| US05/460,847 US3950446A (en) | 1974-04-15 | 1974-04-15 | Process for producing ethynylating agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IT1022545B true IT1022545B (en) | 1978-04-20 |
Family
ID=27017923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT2798174A IT1022545B (en) | 1973-10-01 | 1974-10-01 | Ethynyl carbinol prepn. from unsatd. ketones - pref. methyl vinyl ketone, by ethynylation with magnesium acetylene complex in liq. ammonia |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT340884B (en) |
| IT (1) | IT1022545B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027269A1 (en) * | 1980-07-18 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | 3,6-DIMETHYL-3-HYDROXY-1-OCTINE AND -1-OCTENE AND DERIVATIVES THEREOF AND THEIR USE AS A FRAGRANCE AND METHOD FOR THE PRODUCTION OF 3,6-DIMETHYL-3-HYDROXY OCTANE |
| GB8317850D0 (en) * | 1983-06-30 | 1983-08-03 | Roecar Holdings Nv | Rooperol and its derivatives |
-
1974
- 1974-10-01 IT IT2798174A patent/IT1022545B/en active
- 1974-10-01 AT AT789574A patent/AT340884B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| ATA789574A (en) | 1977-05-15 |
| AT340884B (en) | 1978-01-10 |
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