SU1174435A1 - Method of producing tin di-(carbetoxymethyl) dibromide - Google Patents
Method of producing tin di-(carbetoxymethyl) dibromide Download PDFInfo
- Publication number
- SU1174435A1 SU1174435A1 SU843744826A SU3744826A SU1174435A1 SU 1174435 A1 SU1174435 A1 SU 1174435A1 SU 843744826 A SU843744826 A SU 843744826A SU 3744826 A SU3744826 A SU 3744826A SU 1174435 A1 SU1174435 A1 SU 1174435A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- minutes
- crown
- boiling
- carbetoxymethyl
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title claims abstract description 5
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000009835 boiling Methods 0.000 claims abstract 4
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- 150000003983 crown ethers Chemical class 0.000 claims abstract 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- -1 carbethoxymethyl Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- GSDRMAHJAKQAOZ-UHFFFAOYSA-N diethyl 3-phenylpentanedioate Chemical compound CCOC(=O)CC(CC(=O)OCC)C1=CC=CC=C1 GSDRMAHJAKQAOZ-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
СПОСОБ ПОЛУЧЕНИЯ ДВУБРОМИСТОГО ДИ-(КАРБЭТОКСИМЕТИЛ Ч)ЛОВА взаимодействием порошка олова и этилового эфира бромуксусной кислоты при мол рном соотношении I;2 и с использованием кип чени , отличающийс тем, что, с целью интенсификации процесса и увеличени выхода целевого продукта, процесс ведут в присутствии каталитического количества краун-эфира 15-краун-5 в две стадии - нагреванием реакционной массы при 60-70 С в течение 1015 мин, а затем кип чением в течение ,5-15 мин.METHOD FOR OBTAINING BILOMBIDE DI- (CARBETOXIMETHYL C) LOVA by the interaction of tin powder and ethyl bromoacetic acid ether at a molar ratio of I; 2 and using boiling, characterized in that, in order to intensify the process and increase the yield of the target product, the process is conducted in the presence the catalytic amount of crown ether 15-crown-5 in two stages — by heating the reaction mass at 60–70 ° C for 1015 minutes and then boiling for 5–15 minutes.
Description
чh
. NU. NU
00 СП Изобретение относитс к элементор ганической химии, а именно к улуч шейному способу получени двубромис того ди(карбэтокснметил)-одова формулы (НуС200ССН j,),jf5nBr2 , используемо го в органическом синтезе как полупродукт дл получени стабилизаторов полимеров типа поливинилхлорида. Цель изобретени интенсификаци процесса и увеличение выхода целево го продукта. Пример. 11,86 г (0,1 г-ато порошка олова, 33,4 г (0,2 моль этилового эфира бромуксусной кислоты и 2 г (0,0091 моль-) 15-краун--5 чисто ты не менее 95% (ГЖХ ) нагревают при интенсивном перемешивании в течение 15 мин при , после чего реакцион ную смесь довод т до кипени , кип т т 10 мин и охлаждают. Реакционна смесь кристаллизуетс в виде массы светло-коричневого цвета, частично содержащей белые игольчатые кристаллы . Содержимое колбы промывают эфиром и перекристаплизовывают из бен- зола. Выход двубромистого ди-(карб- этоксиметил)-олова 23,0 г (51%), Т.пл, 139-140®С. По литературным данвдм т.пл, , ,йдено, %: С 21,33; Н 3,15; Sn 6,30. вычислено, %: С 21,22; Н 3,12; Sn 26,22. Выделено .также 10,14 г не идентифицированного твердого остатка, не плав щегос при . П р и м е р 2. Получают двубромистый ди-(карбэтоксиметил)-олова соглас но примеру 1, но при в течение 5мин. Выход целевого продукта 22,77 г (50,5%). Т.ип. 139С, Найдено, %: С 21;35; Н 3,14; Sn 26,28. Вычислено, %: С 21,22; Н 3,12; Sn 26,22.П ри м е р 3. Осуществл лось по лучение двубромистого ди-(карбэтоксн. метил)- олова согласно примеру I, но при в течение 15 мин. Выход целевого продукта 23,45 г (52%). Т.пл. 139С. Найдено, %: С 21,30; Н 3,16; Sn 26,31. 1Вычислено, % С 21,22; Н 3,12; Sn 26,22. Приме р 4. 11,86 г (0,1 г-атом) порошка олова, 33,4 г (0,2 моль| этилового эфира бромуксусной кислоты и 2г (0,0091 моль) 15-краун-5 чистоты не менее 95% (ШХ) нагревают при интенсивном перемешивании в течение 15 мин при 60С, после чего реакционную смесь довод т до , выдерживают в течение 15 мин и охлаждают. Содержимое колбы фильтруют, осадок промывают эфиром и перекристаллизовы- вают из бензола. Выход двубромистого ди-(карбэтоксиметил)-олова 8,9 г (19,6%). Т.пл. 139-142 С. По литературным данным т.пл. 139°С. Найдено, % С 21,42; Н 3,21; Sn 26,49. Вычислено, %: С 21,22; Н 3,12; Sn 26,22. Снижение выхода целевого продукта обусловлено тем, что на второй стадии нагревани реакционную смесь не кип т т , а довод т до 100°С и выдерживают при этой температуре 15 мин.00 SP The invention relates to elemental chemistry, in particular, to an improved method for the preparation of dibromide di (carbethoxmethyl) one formula (NuC200CCH j,), jf5nBr2, used in organic synthesis as an intermediate product for the preparation of polyvinyl chloride type polymer stabilizers. The purpose of the invention is to intensify the process and increase the yield of the target product. Example. 11.86 g (0.1 g-atom of tin powder, 33.4 g (0.2 mol of bromoacetic acid ethyl ester and 2 g (0.0091 mol)) 15-crown - 5 purely not less than 95% ( GLC is heated with vigorous stirring for 15 minutes, after which the reaction mixture is brought to a boil, boiled for 10 minutes and cooled. The reaction mixture crystallizes as a mass of light brown color, partially containing white needles. ether and recrystallized from benzene. The yield of dibromic di- (carbethoxymethyl) -toluene is 23.0 g (51%), Tpl, 139-140® C. According to the literature m danvdm m.p.,,,,%: C 21.33; H 3.15; Sn 6.30. Calculated,%: C 21.22; H 3.12; Sn 26.22. Selected .Also 10 , 14 g of an unidentified solid residue, not melting at. EXAMPLE 2 A di- (carbethoxymethyl) -tromide bromide is obtained according to Example 1, but at 5 minutes. The yield of the desired product is 22.77 g (50 , 5%). T.ip. 139C, Found,%: C 21; 35; H 3.14; Sn 26.28. Calculated,%: C 21.22; H 3.12; Sn 26.22P Example 3. The production of di-bromide di- (carbethox. methyl) - tin according to example I, but for 15 minutes The yield of the target product is 23.45 g (52%). M.p. 139C. Found,%: C 21.30; H 3.16; Sn 26.31. 1Calculated,% С 21,22; H 3.12; Sn 26.22. Example 4: 11.86 g (0.1 g atom) of tin powder, 33.4 g (0.2 mol | bromoacetic acid ethyl ester and 2 g (0.0091 mol) of 15-crown-5 with a purity of at least 95 % (SH) was heated with vigorous stirring for 15 minutes at 60 ° C, after which the reaction mixture was made up, allowed to stand for 15 minutes, and cooled. The contents of the flask were filtered, the precipitate was washed with ether, and recrystallized from benzene. carbethoxymethyl) -tin 8.9 g (19.6%). mp 139-142 C. According to literature data, mp 139 ° C. Found,% C 21.42; H 3.21; Sn 26 , 49. Calculated,%: C 21.22; H 3.12; Sn 26.22. Decrease in yield Spruce product due to the fact that the second heating step, the reaction mixture is heated under reflux, and adjusted to 100 ° C and kept at this temperature for 15 minutes.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU843744826A SU1174435A1 (en) | 1984-03-11 | 1984-03-11 | Method of producing tin di-(carbetoxymethyl) dibromide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU843744826A SU1174435A1 (en) | 1984-03-11 | 1984-03-11 | Method of producing tin di-(carbetoxymethyl) dibromide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1174435A1 true SU1174435A1 (en) | 1985-08-23 |
Family
ID=21120598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843744826A SU1174435A1 (en) | 1984-03-11 | 1984-03-11 | Method of producing tin di-(carbetoxymethyl) dibromide |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1174435A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068374A (en) * | 1990-02-17 | 1991-11-26 | T. Goldschmidt Ag | Method for the preparation of anhydrous tin-dicarboxylate-dihalides |
-
1984
- 1984-03-11 SU SU843744826A patent/SU1174435A1/en active
Non-Patent Citations (1)
| Title |
|---|
| J,Org.Chem., 1951, 16 р,466475, * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068374A (en) * | 1990-02-17 | 1991-11-26 | T. Goldschmidt Ag | Method for the preparation of anhydrous tin-dicarboxylate-dihalides |
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