CH368152A - Verfahren zur Herstellung von Acetylenderivaten - Google Patents

Verfahren zur Herstellung von Acetylenderivaten

Info

Publication number: CH368152A
Authority: CH; Switzerland
Prior art keywords: methyl; acid; pentene; alkoxy; hydroxy
Prior art date: 1958-02-13

Application number

CH5580958A

Other languages

German (de)

English (en)

Inventor

Herbert Dr Lindlar

Marc Dr Montavon

Gabriel Dr Saucy

Original Assignee

Hoffmann La Roche

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.)

1958-02-13

Filing date

1958-02-13

Publication date

1963-03-31

1958-02-13 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1958-02-13 Priority to CH5580958A priority Critical patent/CH368152A/de

1959-01-13 Priority to BE574702A priority patent/BE574702A/fr

1959-01-28 Priority to DK32459A priority patent/DK104935C/da

1963-03-31 Publication of CH368152A publication Critical patent/CH368152A/de

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 5
150000000475 acetylene derivatives Chemical class 0.000 title claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 4
XTYLJMKJLMHFJK-UHFFFAOYSA-N 1,1,3,3-tetraethoxy-2-methylpropane Chemical compound CCOC(OCC)C(C)C(OCC)OCC XTYLJMKJLMHFJK-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 claims description 3
238000010653 organometallic reaction Methods 0.000 claims description 3
-1 1-ethoxy Chemical group 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
230000003197 catalytic effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
238000009835 boiling Methods 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
IHCLUFSKPOJGDC-UHFFFAOYSA-N 1-ethoxy-2-methylprop-1-ene Chemical compound CCOC=C(C)C IHCLUFSKPOJGDC-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229940072033 potash Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical compound C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 1
XDHOEHJVXXTEDV-HWKANZROSA-N (e)-1-ethoxyprop-1-ene Chemical compound CCO\C=C\C XDHOEHJVXXTEDV-HWKANZROSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
JLATWWIHMHDXCO-UHFFFAOYSA-N C(C)(C)OC(C(C(OC(C)C)OC(C)C)C)OC(C)C Chemical compound C(C)(C)OC(C(C(OC(C)C)OC(C)C)C)OC(C)C JLATWWIHMHDXCO-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000021466 carotenoid Nutrition 0.000 description 1
150000001747 carotenoids Chemical class 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
- C07C33/042—Acyclic alcohols with carbon-to-carbon triple bonds with only one triple bond

Landscapes

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

CH5580958A 1958-02-13 1958-02-13 Verfahren zur Herstellung von Acetylenderivaten CH368152A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH5580958A CH368152A (de)	1958-02-13	1958-02-13	Verfahren zur Herstellung von Acetylenderivaten
BE574702A BE574702A (fr)	1958-02-13	1959-01-13	Procédé pour la préparation de composés acétyléniques
DK32459A DK104935C (da)	1958-02-13	1959-01-28	Fremgangsmåde til fremstilling af 1-alkoxy-2-methyl-3-hydroxy-penten-(1)-yner-(4) eller acetaler deraf.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH5580958A CH368152A (de)	1958-02-13	1958-02-13	Verfahren zur Herstellung von Acetylenderivaten

Publications (1)

Publication Number	Publication Date
CH368152A true CH368152A (de)	1963-03-31

Family

ID=4520105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5580958A CH368152A (de)	1958-02-13	1958-02-13	Verfahren zur Herstellung von Acetylenderivaten

Country Status (3)

Country	Link
BE (1)	BE574702A (fr)
CH (1)	CH368152A (fr)
DK (1)	DK104935C (fr)

1958
- 1958-02-13 CH CH5580958A patent/CH368152A/de unknown
1959
- 1959-01-13 BE BE574702A patent/BE574702A/fr unknown
- 1959-01-28 DK DK32459A patent/DK104935C/da active

Also Published As

Publication number	Publication date
DK104935C (da)	1966-07-25
BE574702A (fr)	1959-07-13

Publication	Publication Date	Title
CH368152A (de)	1963-03-31	Verfahren zur Herstellung von Acetylenderivaten
DE830050C (de)	1952-01-31	Verfahren zur Herstellung von in 5-Stellung substituierten Furan-2-carbonsaeureestern
DE870856C (de)	1953-03-16	Verfahren zur Herstellung von Formamiden bzw. Aminen
DE951811C (de)	1956-11-08	Verfahren zur Herstellung von Propiolsaeure
DE1112730B (de)	1961-08-17	Verfahren zur Herstellung von Acetylenverbindungen
AT210574B (de)	1960-08-10	Verfahren zur Herstellung von 1,18-Di-[2', 6', 6'-trimethylcyclohexen-(1')-yl]-3, 7, 12, 16-tetramethyl-8, 11-dioxy-octadecahexaen-(2, 4, 6, 12, 14, 16)-in-(9)
DE875804C (de)	1953-05-07	Verfahren zur Herstellung von Umwandlungsprodukten des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters
DE892893C (de)	1953-10-12	Verfahren zur Herstellung von Carbonsaeureestern
DE1081898B (de)	1960-05-19	Verfahren zur Herstellung von ª‡-(2-Propyl-4, 5-methylendioxy-phenyl)-aethyl-acetalen
CH321106A (de)	1957-04-30	Verfahren zur Herstellung eines Polyendialdehyds
AT216484B (de)	1961-07-25	Verfahren zur Herstellung von 2-Alkylnitraten
DE744081C (de)	1944-01-11	Verfahren zur Herstellung von 2-Methyl-butin-(3)-ol-2
AT276340B (de)	1969-11-25	Verfahren zur Herstellung von neuen, gegebenenfalls verätherten Mono- und Dimethylolfluoralkanamiden
DE958022C (de)	1957-02-14	Verfahren zur Herstellung von Trichloralkylphosphaten
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DE864397C (de)	1953-01-26	Verfahren zur Herstellung von 1-substituierten 6-Alkoxy-2-ketotetrahydronaphthalinen
AT203475B (de)	1959-05-25	Verfahren zur Herstellung von ungesättigten Ketonen
DE1618861C3 (de)	1977-06-02	Verfahren zur Herstellung von ungesättigten Esteralkoholen
AT228182B (de)	1963-07-10	Verfahren zur Herstellung von Triolen
AT211817B (de)	1960-11-10	Verfahren zur Herstellung von β-Lactonen
DE2912052A1 (de)	1980-03-20	Verfahren zur herstellung von 2eckige klammer auf 4-(thienylcarbonyl)phenyl eckige klammer zu -propionsaeure
DE2819798A1 (de)	1979-11-08	Verfahren zur herstellung von 3-phenyl-pyridazon-(6)
CH269655A (de)	1950-07-15	Verfahren zur Herstellung von 5-Äthoxyäthyl-5-allylbarbitursäure.
CH242609A (de)	1946-05-31	Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates.
DE3029270A1 (de)	1982-03-18	Verfahren zur herstellung von 3,5-dimethyl-4-pentensaeure