SU206577A1 - METHOD FOR OBTAINING THE UNDERTAINABLE 1 ACRYLIC ACID ESTERS - Google Patents
METHOD FOR OBTAINING THE UNDERTAINABLE 1 ACRYLIC ACID ESTERSInfo
- Publication number
- SU206577A1 SU206577A1 SU1139361A SU1139361A SU206577A1 SU 206577 A1 SU206577 A1 SU 206577A1 SU 1139361 A SU1139361 A SU 1139361A SU 1139361 A SU1139361 A SU 1139361A SU 206577 A1 SU206577 A1 SU 206577A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acrylic acid
- obtaining
- undertainable
- acid esters
- acid
- Prior art date
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N ethoxyethane;trifluoroborane Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- -1 allyl ester Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N silicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N Boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- CUSSMMZGYVNARC-UHFFFAOYSA-N C(C=C)(=O)O[Si](O)(O)O Chemical compound C(C=C)(=O)O[Si](O)(O)O CUSSMMZGYVNARC-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N Silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- WPBNLDNIZUGLJL-UHFFFAOYSA-N prop-2-ynyl prop-2-enoate Chemical compound C=CC(=O)OCC#C WPBNLDNIZUGLJL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Description
Пзобретение относитс к способам получени непредельных эфиров акриловой кислоты, которые могут найти широкое использование в органическом синтезе благодар наличию кратных св зей в кислотном и спиртовом остатках.The invention relates to methods for producing unsaturated acrylic acid esters, which can be widely used in organic synthesis due to the presence of multiple bonds in acid and alcohol residues.
Пзвестный способ получени аллилового эфира акриловой кислоты состоит в дегалоидировании аллилового эфира а,р-дибромпропионовой кислоты цинком и серной кислотой в среде аллилового спирга. Однако выход продукта при этом невысок.The well-known method of producing acrylic acid allyl ester is to dehalogenize the a, p-dibromopropionic acid allyl ester with zinc and sulfuric acid in an allyl alcohol. However, the product yield is not high.
Предлагаемый способ заключаетс в том, что кремнеангидрид акриловой кислоты подвергают взаимодействию с непредельным спиртом при 40-50°С в присутствии в качестве катализатора эфирата трехфтористого бора и ингибитора полимеризации.The proposed method consists in that acrylic acid silicic anhydride is reacted with unsaturated alcohol at 40-50 ° C in the presence of boron trifluoride etherate and a polymerization inhibitor as a catalyst.
Выход продукта составл ет 70-74% от теории.The product yield is 70-74% of theory.
Пример 1. Получение аллилового эфира акриловой кислоты.Example 1. Obtaining allyl ester of acrylic acid.
В трехгорлую колбу с мешалкой, термометром и обратным холодильником с хлоркальциевой трубкой помещают 19 г (0,06 моль) свежеприготовленного кремнеангидрида акриловой кислоты, 0.,5 г гидрохинона и 0,4 г эфирата трехфтористого бора и при 15-16°С прикапывают туда же 27,6 г (0,11 моль) аллилового спирта. Реакционную смесь нагревают до 40-50°С и выдерживают при этой температуре 4-5 час. При этом выпадает гель ортокремневой кислоты. Далее к смеси прибавл ют 50 мл воды дл разрушени борфторидного комплекса, органическую часть экстрагируют эфиром, объединенные эфирные выт жки сушат сульфатом натри , эфир упаривают , а остаток подвергают фракционированной разгонке. Получают 17,5 г (70% отIn a three-necked flask with a stirrer, thermometer and reflux condenser with a calcium chloride tube, 19 g (0.06 mol) of freshly prepared acrylic acid silicate, 0. 5 g of hydroquinone and 0.4 g of boron trifluoride etherate are added and dropping there at 15-16 ° C the same 27.6 g (0.11 mol) of allyl alcohol. The reaction mixture is heated to 40-50 ° C and maintained at this temperature for 4-5 hours. This results in an orthosilicic acid gel. Next, 50 ml of water was added to the mixture to destroy the boron fluoride complex, the organic portion was extracted with ether, the combined ether extracts were dried with sodium sulfate, the ether was evaporated, and the residue was subjected to fractional distillation. Get 17.5 g (70% of
теории) аллилового эфира акриловой кислотыtheory) allyl ester of acrylic acid
с т. кип. 120-122°С, df 0,9631, пц 1,4210 и MR 30,49, найд. 30,74.with t. kip. 120-122 ° C, df 0.9631, pc 1.4210 and MR 30.49, found. 30.74.
СоПдОа.CoPD
Пайдено, %: С 64,19; П 7,06.Paydeno,%: C 64.19; P 7.06.
Вычислено, %: С 64,28; П 7,14.Calculated,%: C 64.28; P 7.14.
Пример 2. Получение Example 2. Getting
пропаргилового эфира акриловой кислоты.propargyl ester of acrylic acid.
Пропаргиловый эфир акриловой кислоты получают в услови х предыдущего опыта взаимодействием 19 г (0,06 моль} кремнеангидрида акриловой кислоты с 28,5 г (0,118 моль) проиаргилового спирта в присутствии 0,4 г эфирата трехфтористого бора и 0,5 г гидрохинона. Получают 19,9 г (74% от теории) пропаргилового эфира с т. кип. 52- 54°С/20 мм, По 1,4345, df 0,9899 и MR найд. 28,96, выч. 29,08. 34Acrylic acid propargyl ester is obtained, under the conditions of the previous experiment, by the reaction of 19 g (0.06 mol) of acrylic acid silicate with 28.5 g (0.118 mol) of pro-argyl alcohol in the presence of 0.4 g of boron trifluoride etherate and 0.5 g of hydroquinone. 19.9 g (74% of theory) of propargyl ether with a bale of 52-54 ° C / 20 mm, 1.4345, df 0.9899 and MR found 28.96, calcd 29.08 34
Найдено, %: С 65,27; Н 5,31.с целью упрощени процесса и повышени Found,%: C 65.27; H 5.31. With the aim of simplifying the process and increasing
Вычислено, %: С 65,45; Н 5,45.выхода продукта, кремнеангидрид акриловойCalculated,%: C 65.45; H 5,45. Product outlet, acrylic silicate
Предмет изобретени предельным спиртом при 40-50°С в присутСпособ получени непредельных эфировтрехфтористого бора в качестве катализаакриловой кислоты, отличающийс тем, что,тора.The subject matter of the invention is a limit alcohol at 40-50 ° C in the presence of a method for producing unsaturated boron trifluoride ethers as catalysacrylic acid, characterized in that it is a torus.
206577 206577
кислоты подвергают взаимодействию с не5ствии ингибитора полимеризации и эфиратаacids are reacted with inhibition of polymerization inhibitor and etherate
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU206577A1 true SU206577A1 (en) |
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