PL425232A1 - New liquid-crystalline thiophen-3-yl 3,4,5-tri(4-(n-alkyl-1-yloxy)benzyl)benzoate esters and method for obtaining them - Google Patents
New liquid-crystalline thiophen-3-yl 3,4,5-tri(4-(n-alkyl-1-yloxy)benzyl)benzoate esters and method for obtaining themInfo
- Publication number
- PL425232A1 PL425232A1 PL425232A PL42523218A PL425232A1 PL 425232 A1 PL425232 A1 PL 425232A1 PL 425232 A PL425232 A PL 425232A PL 42523218 A PL42523218 A PL 42523218A PL 425232 A1 PL425232 A1 PL 425232A1
- Authority
- PL
- Poland
- Prior art keywords
- alkyl
- yloxy
- tri
- benzyl
- chain
- Prior art date
Links
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 title 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004973 liquid crystal related substance Substances 0.000 abstract 2
- -1 thiophene-3-yl Chemical group 0.000 abstract 2
- QUBJDMPBDURTJT-UHFFFAOYSA-N 3-chlorothiophene Chemical compound ClC=1C=CSC=1 QUBJDMPBDURTJT-UHFFFAOYSA-N 0.000 abstract 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052786 argon Inorganic materials 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000005457 ice water Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 230000016507 interphase Effects 0.000 abstract 1
- 229910001416 lithium ion Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000003586 protic polar solvent Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Liquid Crystal Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem zgłoszenia są nowe ciekłokrystaliczne estry 3,4,5-tri(4-(n-alkilo-1-yloksy)benzylo)benzoesanu tiofeno-3-ylu o wzorze 1, w którym R oznacza grupę alkilową o liczbie węgli w łańcuchu od 8 do 16, znajdujące zastosowanie przy produkcji baterii litowo-jonowych. Zgłoszenie obejmuje też sposób otrzymywania nowych ciekłokrystalicznych estrów 3,4,5-tri(4-(n-alkilo-1-yloksy)benzylo)benzoesanu tiofeno-3-ylu o wzorze 1, w którym R oznacza grupę alkilową o liczbie węgli w łańcuchu od 8 do 16. Przedmiotowy sposób polega na tym, że w atmosferze inertnego gazu, korzystnie azotu lub argonu, dodaje się związek o wzorze ogólnym 2, w którym R oznacza grupę alkilową o liczbie węgli w łańcuchu od 8 do 16 i katalizator przeniesienia międzyfazowego, korzystnie czwartorzędowej soli amonowej fluorowców, do 3-chlorotiofenu rozpuszczonego w rozpuszczalniku aprotycznym, korzystnie suchym i prowadzi się reakcję w przedziale temperatur (55 ÷ 65)°C w okresie od 4 dni do 12 dni, następnie otrzymaną mieszaninę wlewa się do wody z lodem, w stosunku objętościowym od 5:1 do 1:2, a otrzymany surowy produkt oczyszcza się wykorzystując protyczny i polarny rozpuszczalnik, korzystnie woda lub metanol.The subject of the application are new liquid crystal thiophene-3-yl 3,4,5-tri (4- (n-alkyl-1-yloxy) benzyl) benzoate esters of the formula I, in which R is an alkyl group with a carbon number in the chain from 8 to 16, used in the production of lithium-ion batteries. The application also covers the preparation of new thiophene-3-yl 3,4,5-tri (4- (n-alkyl-1-yloxy) benzyl) benzoate liquid crystal esters of the formula I, in which R is an alkyl group with the number of carbon in the chain 8 to 16. The present method consists in adding a compound of general formula II in which R is an alkyl group with a carbon number in the chain from 8 to 16 and an interphase transfer catalyst under an atmosphere of an inert gas, preferably nitrogen or argon, preferably quaternary ammonium salt of halogens, to 3-chlorothiophene dissolved in an aprotic, preferably dry solvent, and the reaction is carried out in the temperature range (55 ÷ 65) ° C for a period from 4 days to 12 days, then the obtained mixture is poured into ice water, in a volume ratio of 5: 1 to 1: 2, and the obtained crude product is purified using a protic and polar solvent, preferably water or methanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL425232A PL238397B1 (en) | 2018-04-16 | 2018-04-16 | New liquid-crystalline thiophen-3-yl 3,4,5-tri(4-(n-alkyl-1-yloxy)benzyl)benzoate esters and method for obtaining them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL425232A PL238397B1 (en) | 2018-04-16 | 2018-04-16 | New liquid-crystalline thiophen-3-yl 3,4,5-tri(4-(n-alkyl-1-yloxy)benzyl)benzoate esters and method for obtaining them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL425232A1 true PL425232A1 (en) | 2019-10-21 |
| PL238397B1 PL238397B1 (en) | 2021-08-16 |
Family
ID=68238715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL425232A PL238397B1 (en) | 2018-04-16 | 2018-04-16 | New liquid-crystalline thiophen-3-yl 3,4,5-tri(4-(n-alkyl-1-yloxy)benzyl)benzoate esters and method for obtaining them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238397B1 (en) |
-
2018
- 2018-04-16 PL PL425232A patent/PL238397B1/en unknown
Non-Patent Citations (2)
| Title |
|---|
| J. CHEM, SOC. CHEM. COMMUN, 1 March 1990 (1990-03-01) * |
| TETRAHEDRON. LETT., TETRAHEDRON. LETT., 20 August 1999 (1999-08-20) * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL238397B1 (en) | 2021-08-16 |
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