SU303321A1 - Method of producing xylitane phosphonites - Google Patents
Method of producing xylitane phosphonitesInfo
- Publication number
- SU303321A1 SU303321A1 SU1405110A SU1405110A SU303321A1 SU 303321 A1 SU303321 A1 SU 303321A1 SU 1405110 A SU1405110 A SU 1405110A SU 1405110 A SU1405110 A SU 1405110A SU 303321 A1 SU303321 A1 SU 303321A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- xylitane
- phosphonites
- producing
- reaction
- mro
- Prior art date
Links
- LROMFDHROPKFSO-UHFFFAOYSA-N dioxidophosphane Chemical class [O-]P[O-] LROMFDHROPKFSO-UHFFFAOYSA-N 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HEBKCHPVOIAQTA-SCDXWVJYSA-N Xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 4
- 229960002675 Xylitol Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000010447 xylitol Nutrition 0.000 description 4
- 239000000811 xylitol Substances 0.000 description 4
- VOEUGNICNCPEPW-UHFFFAOYSA-N C(CCCCC)P([O-])[O-] Chemical compound C(CCCCC)P([O-])[O-] VOEUGNICNCPEPW-UHFFFAOYSA-N 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- OLGGYSFJQGDOFX-UHFFFAOYSA-N nonylphosphonic acid Chemical compound CCCCCCCCCP(O)(O)=O OLGGYSFJQGDOFX-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940022860 xylitan Drugs 0.000 description 2
- ACOGNPJCAUNYKJ-ORFYIMQMSA-N (2S,3S)-2-[4-[(1R)-1-amino-2-hydroxyethyl]triazol-1-yl]-1-[4-[4-[4-[(2S,3S)-2-[4-[(1R)-1-amino-2-hydroxyethyl]triazol-1-yl]-3-methylpentanoyl]piperazin-1-yl]-6-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethylamino]-1,3,5-triazin-2-yl]piperazin-1-yl]-3-methylpenta Chemical compound Cl.N1([C@@H]([C@@H](C)CC)C(=O)N2CCN(CC2)C=2N=C(NCCOCCOCCOCC#C)N=C(N=2)N2CCN(CC2)C(=O)[C@H]([C@@H](C)CC)N2N=NC(=C2)[C@@H](N)CO)C=C([C@@H](N)CO)N=N1 ACOGNPJCAUNYKJ-ORFYIMQMSA-N 0.000 description 1
- HGSGRPUUUSRMLX-UHFFFAOYSA-N CCCCCCCCCP([O-])[O-] Chemical compound CCCCCCCCCP([O-])[O-] HGSGRPUUUSRMLX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- KXHIPQLQJZDXKF-UHFFFAOYSA-N nonyl phosphite Chemical compound CCCCCCCCCOP([O-])[O-] KXHIPQLQJZDXKF-UHFFFAOYSA-N 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- -1 polyol compound Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Description
Изобретение относитс к области получени новых соединений, которые представл ют ннтерес в качестве веществ, вли ющих на углеводный обмен, и детергентов. Способ получени фосфонитов ксилитана общей формулы I I .СИ-СИ. СК-СНгО-Р-Н I где R - алкил, основан на известной реакции между фосфонистой кислотой и полиольным соединением и заключаетс в том, что ксилит или ксилитан обрабатывают фосфонистой кислотой в среде органического растворител прн нагревании, желательно до кипени реакционной смеси, с азеотропной отгонкой воды и последующим выделением целевого продукта известными приемами. Пример 1. В реакционную колбу загружают 13,4 г (0,1 моль ксилитана, 19,2 г (0,1 моль} нонилфосфонистой кислоты и р-ксилол в качестве растворител . Реакционную смесь нагревают при температуре кипени растворител до полного прекращени выделени воды. Контроль реакции осуществл етс методом бумажной хроматографии или тонкослойной хроматографии на пластинах «силуфол. По окончании реакции растворитель отгон ют, а продукт реакции - в зкое прозрачное масло промывают эфиром. Выход 30,8 г (100%). Дл полученного продукта, идентифицированного как нонилфосфонит ксилитана, ng 1,4800; tff 1,1130. Вычислено, %: С 54,5; Н 9,42; MRn 78,592. CnHagOsP. Найдено, %: 54,7; Н 9,58; MRn 78,590. Дл нонилфосфонита ксилитана, полученного нереэтерификацией, Пц° 1,4790; df 1,1120. Вычислено MRo 78,592. Найдено MRo 78,523. Пример 2. Синтез гексилфосфонита ксилитана ведут в услови х, описанных в примере 1, при отношении исходных компонентов ксилитан : гексилфосфонпста кислота равном 1:1. Выход количественный (100%). Продукт идентифицирован как гексилфосфонит ксилитана, п 1,4779; d 1,1675. Найдено MRo 64,51. Вычислено MRo 64,738. Пример 3. В реакционную колбу загружают 15,2 г (0,1 моль) ксилита, 19,2 г (0,1 моль) нонилфосфонистой кислоты и растворитель р-ксилол и провод т реакцию, как в примере 1. Продукт реакции - в зкое прозрачное масло . Выход количественный (100% или 30,6 г). Полученный продукт идентифицирован как нонилфосфопит ксилитана, п 1,4801; d 1,1137. Вычислено, %: С 54,5; Н 9,42; Р 10,00; MRo 78,592. CuHsgOsP. Найдено, %: П 9,36; Р 10,52; MRo 78,571. Пример 4. Синтез гексилфосфонита ксилитана ведут в услови х, аналогичных примеру 3, при отношении ксилит : гексилфосфониста кислота равном 1 : 1. Выход 99-100%. Полученный продукт идентифицирован ксилитана, 1,4850; как гексилфосфонит df 1,1759. Вычислено, %: С 49,62; Н 8,65; Р 11,65; MRD 64,733. СпНазОзР. 4 Найдено, С 49,61; Н 8,22; Р 11,59; MRD 64,745. Предмет изобретени Способ получени фосфонитов ксилитана общей формулы сн-сн II . сы-сн,о-р-н где R - алкил, отличающийс тем, что ксилит или ксилитан обрабатывают фосфонистой кислотой в среде органического растворител при нагревании с азеотропной отгонкой воды и поледующим выделением целевого продукта известными приемами.The invention relates to the field of producing new compounds that are of interest as substances affecting carbohydrate metabolism and detergents. The method of producing xylitan phosphonites of the general formula I I .SI-SI. CK-CHGO-P-H I, where R is alkyl, is based on a known reaction between a phosphonous acid and a polyol compound and consists in that xylitol or xylitane is treated with phosphonous acid in an organic solvent prn heated, preferably to boil the reaction mixture, with azeotropic distillation of water and the subsequent isolation of the target product by known methods. Example 1. To the reaction flask was charged 13.4 g (0.1 mol xylitane, 19.2 g (0.1 mol) nonylphosphonic acid, and p-xylene as the solvent. The reaction mixture was heated at the boiling point of the solvent until all the water was released) The reaction was monitored by paper chromatography or thin layer chromatography on plates "Silufol. After the completion of the reaction, the solvent was distilled off and the reaction product was washed with clear oil with ether. Yield 30.8 g (100%). For the resulting product, identified as nonilfo xylitane phonite, ng 1.4800; tff 1.1130. Calculated,%: C 54.5; H, 9.42; MRn 78.592. CnHagOsP. Found,%: 54.7; H, 9.58; MRn 78.590. For nonylphosphonite xylitane obtained by non-esterification, PC ° 1.4790; df 1.1120. Calculated MRo 78.592. Found MRo 78.523. : 1. The yield is quantitative (100%). The product is identified as xylitane hexylphosphonite, n 1.4779; d 1.1675. Found MRo 64.51. Calculated MRo 64,738. Example 3. To the reaction flask was charged 15.2 g (0.1 mol) of xylitol, 19.2 g (0.1 mol) of nonylphosphonic acid and p-xylene solvent, and the reaction was carried out as in Example 1. The reaction product was in Zek transparent oil. The yield is quantitative (100% or 30.6 g). The resulting product was identified as nonylphosphite xylitane, p 1.4801; d 1,1137. Calculated,%: C 54.5; H 9.42; R 10.00; MRo 78,592. CuHsgOsP. Found,%: P 9.36; P 10.52; MRo 78,571. Example 4. Synthesis of xylitane hexylphosphonite is carried out under conditions analogous to Example 3, with a xylitol: hexylphosphonist acid ratio of 1: 1. A yield of 99-100%. The resulting product is identified by xylitane, 1.4850; as hexylphosphonite df 1,1759. Calculated,%: C 49.62; H 8.65; R 11.65; MRD 64,733. SpNazOZR. 4 Found, C 49.61; H 8.22; R 11.59; MRD 64,745. The subject of the invention. A process for the production of xylitan phosphonites of the general formula of CH 2 II. where R is alkyl, characterized in that xylitol or xylitane is treated with phosphonous acid in an organic solvent medium when heated with azeotropic distillation of water and subsequent extraction of the target product by known techniques.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU303321A1 true SU303321A1 (en) |
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