WO1986004055A1 - Procede d'obtention de 2-alkyl- ou 2,2-dialkyl-1,3-propanediols - Google Patents
Procede d'obtention de 2-alkyl- ou 2,2-dialkyl-1,3-propanediols Download PDFInfo
- Publication number
- WO1986004055A1 WO1986004055A1 PCT/SU1984/000075 SU8400075W WO8604055A1 WO 1986004055 A1 WO1986004055 A1 WO 1986004055A1 SU 8400075 W SU8400075 W SU 8400075W WO 8604055 A1 WO8604055 A1 WO 8604055A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- dialkyl
- mixture
- metal halide
- aluminum
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 7
- 150000005309 metal halides Chemical class 0.000 claims abstract description 7
- 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 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 150000002170 ethers Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 14
- 239000011541 reaction mixture Substances 0.000 abstract description 6
- 238000009835 boiling Methods 0.000 abstract description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010277 boron hydride Inorganic materials 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 2-hexyl- Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000013348 organic food Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
Definitions
- the area of availability of the missing product is related to the chemical industry, and, more specifically, the method of radiation is 2-alkalis, or 2-odds,
- the indicated method is not intended for the use of multi-substituted 1,3-pandiands.
- ⁇ n ⁇ a ⁇ a ⁇ e ⁇ izue ⁇ sya used ⁇ lz ⁇ vaniem ⁇ udn ⁇ d ⁇ s ⁇ u ⁇ n ⁇ g ⁇ sy ⁇ ya (2 al ⁇ ilaldegzhd ⁇ v) leg ⁇ le ⁇ ucheg ⁇ ⁇ maldegida, ⁇ blada ⁇ tseg ⁇ ⁇ azd ⁇ azhayuschim deys ⁇ viem on slizis ⁇ ye ⁇ b ⁇ l ⁇ ch ⁇ i and ⁇ zi ⁇ nn ⁇ -a ⁇ ivn ⁇ g ⁇ ⁇ eagen ⁇ a - 505_-n ⁇ y gid ⁇ isi na ⁇ iya, ⁇ ebuyuschey s ⁇ etszhal- n ⁇ y a ⁇ a ⁇ a ⁇ u ⁇ y. .
- the proposed method allows you to do differently 15 mono- and dialkyl substituted 1,3-industrial and to improve the technology of their emission.
- Metal hydride is mixed with metal halide, 20 as a part of which can be used with any suitable metal halide, but the metal ⁇ réelle None
- the resulting mixture adds a diluent - a simple solution, which can be consumed in water, for example, test-25, reagent, we can mix a mixture of diglyme and diethyl.
- Then add the alkyl- or dialkylalmal ether.
- the process is carried out at the boiling point of the boiling mixture of the reacting mixture at the time of stirring. At the end of the reaction, they separate the oily layer, the one layer extrudes 30 EHILIs. The essentials connect with the oil layer, wash and discard the air. Drop off the vacuum transfer and receive the target product.
- the cost of the target product is up to 92 weight (it’s not expensive). 35
- the proposed method is compared to a known method that allows the use of easy-to-use raw materials (alkyl and dialkyl-substituted small ones) - 3 - excludes the use of an active reagent and maldehyde, which causes irritation of the SLUISE compound.
- the proposed method is not known to result in not only dialkyl substituting 1,3- ⁇ andi-5, but not substituted.
- reaction mixture is heated while stirring at 70 ° ⁇ for 20 hours, it is allowed to cool and the mixture is stirred, and the mixture is stirred for 10 minutes. Separate the external organic layer, and wash the external layer 3 times for 30 ml of ethyl ether.
- Example 6 The process is similar to that described in Example 3. There are 40.4 g of methyl-ethyl ether. It takes a fraction of 90-98 ° C / 5 mm, while it is trapped in colorless crystals with a pressure of 40-4 ° C. The yield of 2-methyl-2-ethyl- ⁇ , 3-pandiopanadio 17.3 g (74, b%% theoretical). Example 6.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH3255/86A CH666478A5 (de) | 1984-12-28 | 1984-12-28 | Verfahren zur herstellung von 2-alkyl- bzw. 2,2-dialkyl-1,3-propandiolen. |
JP85500679A JPS62501354A (ja) | 1984-12-28 | 1984-12-28 | 2−アルキルまたは2,2−ジアルキル−1,3−プロパンジオ−ルの製造法 |
DE19843490802 DE3490802T1 (enrdf_load_stackoverflow) | 1984-12-28 | 1984-12-28 | |
FI863483A FI863483L (fi) | 1984-12-28 | 1984-12-28 | Foerfarande foer framstaellning av 2-alkyl- eller 2,2-dialkyl-1,3-propandioler. |
GB08619901A GB2179937B (en) | 1984-12-28 | 1984-12-28 | Method for preparing 2-alkyl-or 2,2-dialkyl-1,3-propanediols |
PCT/SU1984/000075 WO1986004055A1 (fr) | 1984-12-28 | 1984-12-28 | Procede d'obtention de 2-alkyl- ou 2,2-dialkyl-1,3-propanediols |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/SU1984/000075 WO1986004055A1 (fr) | 1984-12-28 | 1984-12-28 | Procede d'obtention de 2-alkyl- ou 2,2-dialkyl-1,3-propanediols |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1986004055A1 true WO1986004055A1 (fr) | 1986-07-17 |
Family
ID=21616880
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SU1984/000075 WO1986004055A1 (fr) | 1984-12-28 | 1984-12-28 | Procede d'obtention de 2-alkyl- ou 2,2-dialkyl-1,3-propanediols |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS62501354A (enrdf_load_stackoverflow) |
CH (1) | CH666478A5 (enrdf_load_stackoverflow) |
DE (1) | DE3490802T1 (enrdf_load_stackoverflow) |
FI (1) | FI863483L (enrdf_load_stackoverflow) |
GB (1) | GB2179937B (enrdf_load_stackoverflow) |
WO (1) | WO1986004055A1 (enrdf_load_stackoverflow) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2479252A1 (fr) * | 1980-03-28 | 1981-10-02 | Timex Corp | Composes a cristaux liquides du type cyclohexyl-dioxanne et dispositif electro-optique du type receveur-recu utilisant de tels composes |
FR2479824A1 (fr) * | 1980-04-03 | 1981-10-09 | Timex Corp | Nouveaux 2-(4-cyanophenyl)-1,3-dioxannes 5-substitues et leur application comme cristaux liquides dans les dispositifs a affichage electro-optique |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4335012A (en) * | 1980-04-03 | 1982-06-15 | Timex Corporation | 5-Substituted-2-(4-cyanophenyl)-1,3-dioxanes |
-
1984
- 1984-12-28 JP JP85500679A patent/JPS62501354A/ja active Pending
- 1984-12-28 GB GB08619901A patent/GB2179937B/en not_active Expired
- 1984-12-28 WO PCT/SU1984/000075 patent/WO1986004055A1/ru active Application Filing
- 1984-12-28 FI FI863483A patent/FI863483L/fi not_active Application Discontinuation
- 1984-12-28 CH CH3255/86A patent/CH666478A5/de not_active IP Right Cessation
- 1984-12-28 DE DE19843490802 patent/DE3490802T1/de not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2479252A1 (fr) * | 1980-03-28 | 1981-10-02 | Timex Corp | Composes a cristaux liquides du type cyclohexyl-dioxanne et dispositif electro-optique du type receveur-recu utilisant de tels composes |
FR2479824A1 (fr) * | 1980-04-03 | 1981-10-09 | Timex Corp | Nouveaux 2-(4-cyanophenyl)-1,3-dioxannes 5-substitues et leur application comme cristaux liquides dans les dispositifs a affichage electro-optique |
Non-Patent Citations (1)
Title |
---|
Journal of the American Chemical Society, Vol. 78, No. 11, June 1956, (American Chemical Society, Washington), Herbert C. Brown et al: "A New Powerful Reducing Agent-Sodium Borohydride in Presence of Aluminium Chloride and Other Polyvalent Metal Halides", pages 2582-2588 * |
Also Published As
Publication number | Publication date |
---|---|
CH666478A5 (de) | 1988-07-29 |
JPS62501354A (ja) | 1987-06-04 |
GB2179937A (en) | 1987-03-18 |
DE3490802T1 (enrdf_load_stackoverflow) | 1987-02-19 |
FI863483A7 (fi) | 1986-08-27 |
GB2179937B (en) | 1988-08-10 |
FI863483A0 (fi) | 1986-08-27 |
FI863483L (fi) | 1986-08-27 |
GB8619901D0 (en) | 1986-09-24 |
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