CH422759A - Verfahren zur Herstellung von p-Vinyl-glycidäthern - Google Patents

Verfahren zur Herstellung von p-Vinyl-glycidäthern

Info

Publication number: CH422759A
Authority: CH; Switzerland
Prior art keywords: sep; vinyl; phenol; mol; solution
Prior art date: 1960-11-24

Application number

CH1274261A

Other languages

German (de)

English (en)

Inventor

Heinrich Dr Krimm

Helmut Dr Mylenbusch

Hermann Dr Schnell

Original Assignee

Bayer Ag

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.)

1960-11-24

Filing date

1961-11-02

Publication date

1966-10-31

1961-11-02 Application filed by Bayer Ag filed Critical Bayer Ag

1966-10-31 Publication of CH422759A publication Critical patent/CH422759A/de

Links

238000000034 method Methods 0.000 title claims description 11
229920002554 vinyl polymer Polymers 0.000 title description 16
238000002360 preparation method Methods 0.000 title description 3
230000008569 process Effects 0.000 title description 3
-1 halohydrin ethers Chemical class 0.000 claims description 15
239000003513 alkali Substances 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 4
230000009471 action Effects 0.000 claims description 3
239000012433 hydrogen halide Substances 0.000 claims description 3
229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical class OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
AAUXVPAKDMCMMN-UHFFFAOYSA-N 2-[(4-ethenylphenoxy)methyl]oxirane Chemical class C1=CC(C=C)=CC=C1OCC1OC1 AAUXVPAKDMCMMN-UHFFFAOYSA-N 0.000 claims 1
150000002085 enols Chemical class 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical class OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 12
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
PWYQHEGKOCEHME-UHFFFAOYSA-N 4-(2-methylprop-1-enyl)phenol Chemical compound CC(C)=CC1=CC=C(O)C=C1 PWYQHEGKOCEHME-UHFFFAOYSA-N 0.000 description 3
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical class C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
VIPGIILSRLAVSF-UHFFFAOYSA-N 2-[[4-(cyclohexen-1-yl)phenoxy]methyl]oxirane Chemical compound C(C1CO1)OC1=CC=C(C=C1)C1=CCCCC1 VIPGIILSRLAVSF-UHFFFAOYSA-N 0.000 description 1
MLMWCIMZUZNDND-UHFFFAOYSA-N 4-(3-methylbut-1-en-2-yl)phenol Chemical compound CC(C)C(=C)C1=CC=C(O)C=C1 MLMWCIMZUZNDND-UHFFFAOYSA-N 0.000 description 1
GXYXTXDETQMQQZ-UHFFFAOYSA-N 4-(3-methylbut-1-enyl)phenol Chemical compound CC(C)C=CC1=CC=C(O)C=C1 GXYXTXDETQMQQZ-UHFFFAOYSA-N 0.000 description 1
YGEZIEXHMBTZMT-UHFFFAOYSA-N 4-(cyclohexen-1-yl)phenol Chemical compound C1=CC(O)=CC=C1C1=CCCCC1 YGEZIEXHMBTZMT-UHFFFAOYSA-N 0.000 description 1
WOQDNINLMDXWRC-UHFFFAOYSA-N 4-pent-1-enylphenol Chemical compound CCCC=CC1=CC=C(O)C=C1 WOQDNINLMDXWRC-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GFAPPHBARXJLBZ-UHFFFAOYSA-N CC(C)=CC(C=C1)=CC=C1OCC1OC1 Chemical compound CC(C)=CC(C=C1)=CC=C1OCC1OC1 GFAPPHBARXJLBZ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000188250 Idas Species 0.000 description 1
101150057104 MCIDAS gene Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000004992 fission Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229930015698 phenylpropene Natural products 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Epoxy Compounds (AREA)

CH1274261A 1960-11-24 1961-11-02 Verfahren zur Herstellung von p-Vinyl-glycidäthern CH422759A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0032612		1960-11-24

Publications (1)

Publication Number	Publication Date
CH422759A true CH422759A (de)	1966-10-31

Family

ID=7094706

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1274261A CH422759A (de)	1960-11-24	1961-11-02	Verfahren zur Herstellung von p-Vinyl-glycidäthern

Country Status (2)

Country	Link
BE (1)	BE609968A (fr)
CH (1)	CH422759A (fr)

1961
- 1961-11-02 CH CH1274261A patent/CH422759A/de unknown
- 1961-11-06 BE BE609968A patent/BE609968A/fr unknown

Also Published As

Publication number	Publication date
BE609968A (fr)	1962-03-01

Publication	Publication Date	Title
DE3042121C2 (fr)	1989-03-16
EP0184731B1 (fr)	1988-05-25	Procédé de préparation de 2-(1-hydroxyméthyl)-acrylonitrile et -acrylates
CH422759A (de)	1966-10-31	Verfahren zur Herstellung von p-Vinyl-glycidäthern
DE2032170C3 (de)	1980-06-19	Verfahren zur Herstellung von Isobornylphenolen
DE2501899B1 (de)	1976-07-08	Verfahren zur herstellung von 2- nitro-4,6-dichlor-5-methylphenol
AT227682B (de)	1963-06-10	Verfahren zur Herstellung neuer p-Vinylphenyl-glycidäther
DE2441030C2 (de)	1984-11-08	Verfahren zur Herstellung von Gemischen der 4- und 5-Stellungsisomeren von &Delta;&uarr;3&uarr;-Cyclohexencarbaldehyden
CH631146A5 (de)	1982-07-30	Verfahren zur herstellung von 2,6-dimethoxy-4-(quaternaeren-alkyl)phenolen.
DE2237750C2 (de)	1974-06-12	Verfahren zur Herstellung von Brenzcatechin
EP0066246A2 (fr)	1982-12-08	Procédé pour la préparation de phénylacétonitriles basiquement substitués
CH627429A5 (de)	1982-01-15	Verfahren zur herstellung von aldehyden.
DE2418973C2 (de)	1976-05-06	Verfahren zur Herstellung von 2-Alkoxy-4-propen- (1) -yl-phenolen
US2079758A (en)	1937-05-11	Unsaturated ethers and process for producing same
US1823127A (en)	1931-09-15	Manufacture of artificial resins
US1816248A (en)	1931-07-28	Manufacture of aromatic hydroxy aldehydes
DE2827935C2 (de)	1983-10-13	Verfahren zur Herstellung von 7,3',4'-Tri-O-&beta;-hydroxyäthyl-rutosid
DE669805C (de)	1939-01-04	Verfahren zur Herstellung von Ringacetalen
DE3210061A1 (de)	1983-09-22	Verfahren zur herstellung von propafenon
DE1028130B (de)	1958-04-17	Verfahren zur Herstellung von Oxyalkylarylaethern
DE953794C (de)	1956-12-06	Verfahren zur Herstellung von AEthern des ª-Oxyadipinsaeuredinitrils
DE2044160A1 (fr)	1972-03-09
DE1593717C (de)	1973-04-05	Verfahren zur Herstellung von 4,4' Dihydroxy stilbenen
DE2621832A1 (de)	1976-11-25	Verfahren zur herstellung organischer saeuren
DE743749C (de)	1944-01-06	Verfahren zur Herstellung eines lactonartigen Derivates des 9,10-Dihydroanthracens
DE1593717A1 (de)	1970-10-22	Verfahren zur Herstellung von 4,4'-Dihydroxy-stilbenen