JPS6159635B2 - - Google Patents
Info
- Publication number
- JPS6159635B2 JPS6159635B2 JP56147140A JP14714081A JPS6159635B2 JP S6159635 B2 JPS6159635 B2 JP S6159635B2 JP 56147140 A JP56147140 A JP 56147140A JP 14714081 A JP14714081 A JP 14714081A JP S6159635 B2 JPS6159635 B2 JP S6159635B2
- Authority
- JP
- Japan
- Prior art keywords
- pentanediol
- trimethyl
- phosgene
- compound
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 4
- UHKHSJAFYFTMSC-UHFFFAOYSA-N 5,5-dimethyl-4-propan-2-yl-1,3-dioxan-2-one Chemical compound CC(C)C1OC(=O)OCC1(C)C UHKHSJAFYFTMSC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- -1 but not limited to Substances 0.000 description 1
- HHDBUIKGCQHELR-UHFFFAOYSA-N carbonic acid;2,2,4-trimethylpentane-1,3-diol Chemical compound OC(O)=O.CC(C)C(O)C(C)(C)CO HHDBUIKGCQHELR-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005486 organic electrolyte Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Ink Jet (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
【発明の詳細な説明】
本発明は１−イソプロピル−２，２−ジメチル
−１，３−プロピレンカーボネートの製法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for producing 1-isopropyl-2,2-dimethyl-1,3-propylene carbonate.
１−イソプロピル−２，２−ジメチル−１，３
−プロピレンカーボネートは以下の化学式：
で示される化合物であり、凝固点が低く、沸点が
高く、広い温度範囲で高い流動性（低粘性）を保
持し得る安定な液状物質であり、かつ、高誘電率
であると共に水に不溶性であり、有機電解質、イ
ンキ媒体、特に高速記録インキジエツト等の特殊
インキ用添加剤、反応溶媒、分散系の溶媒等種々
の分野に使用できる。 1-isopropyl-2,2-dimethyl-1,3
-Propylene carbonate has the following chemical formula: It is a stable liquid substance that has a low freezing point, a high boiling point, can maintain high fluidity (low viscosity) over a wide temperature range, and has a high dielectric constant and is insoluble in water. It can be used in various fields such as organic electrolytes, ink media, especially additives for special inks such as high-speed recording ink jets, reaction solvents, and dispersion solvents.
本発明化合物は２，２，４−トリメチル−１，
３−ペンタンジオールを原料とし、これを発生す
る塩酸ガスを系外に除去しながらホスゲンと脱塩
酸反応させることにより、高収率で得ることがで
きる。 The compound of the present invention is 2,2,4-trimethyl-1,
It can be obtained in high yield by using 3-pentanediol as a raw material and subjecting it to a dehydrochloric acid reaction with phosgene while removing the generated hydrochloric acid gas from the system.
原料となる２，２，４−トリメチル−１，３−
ペンタンジオールは、立体構造的にみて二つの水
酸基が環状カーボネートを形成するのに適した位
置にあり、本発明化合物を高収率で得ることがで
き、かつ、この構造上の特徴から生成した環状カ
ーボネートは特徴的なヒンダード構造を六員環に
もたらすため、安定な化合物が得られるものと考
えられる。 2,2,4-trimethyl-1,3- as a raw material
In pentanediol, two hydroxyl groups are located in suitable positions to form a cyclic carbonate from a steric structure, and the compound of the present invention can be obtained in high yield. It is thought that carbonate provides a characteristic hindered structure in the six-membered ring, resulting in a stable compound.
本発明化合物を製造する別の方法はホスゲンを
用いて直接２，２，４−トリメチル−１，３−ペ
ンタンジオールをカーボネート化する方法であ
る。この方法では冷却した不活性溶媒中にホスゲ
ンを溶解し、これに所定量の２，２，４−トリメ
チル−１，３−ペンタンジオールを直接または不
活性溶媒に溶解して添加する。好ましい不活性溶
媒はベンゾール、トルオール、キシロール等の芳
香族溶媒であるがこれに限定されるものではな
い。 Another method for producing the compounds of the invention is to directly carbonate 2,2,4-trimethyl-1,3-pentanediol using phosgene. In this method, phosgene is dissolved in a cooled inert solvent, and a predetermined amount of 2,2,4-trimethyl-1,3-pentanediol is added thereto either directly or dissolved in the inert solvent. Preferred inert solvents are aromatic solvents such as, but not limited to, benzene, toluol, and xylol.
２，２，４−トリメチル−１，３−ペンタンジ
オールをホスゲンと反応させる方法において、発
生する塩酸を除去する手段としては系中に脱塩酸
剤を共存させる方法が最も一般的な方法と考えら
れるが、この方法では、収率が低く満足すべき結
果は得られない。本発明では発生する塩酸はガス
状で系外に排出せしめ、系内からできるだけ早く
塩酸を除去するか、できるだけ低濃度に維持す
る。これによつて収率は著しく向上する。 In the method of reacting 2,2,4-trimethyl-1,3-pentanediol with phosgene, the most common method for removing generated hydrochloric acid is to coexist a dehydrochloric agent in the system. However, with this method, the yield is low and satisfactory results cannot be obtained. In the present invention, the generated hydrochloric acid is discharged out of the system in gaseous form, and the hydrochloric acid is removed from the system as quickly as possible, or the concentration is maintained as low as possible. This significantly improves the yield.
この方法の利点は常温で反応させることがで
き、しかも反応がほぼ定量的に進行する点であ
る。 The advantage of this method is that the reaction can be carried out at room temperature and that the reaction proceeds almost quantitatively.
上記の方法で得られた１−イソプロピル−２，
２−ジメチル−１，３−プロピレンカーボネート
は蒸留により容易に単離できる。化合物の物理的
化学的諸特性は以下の通りである。 1-isopropyl-2 obtained by the above method,
2-dimethyl-1,3-propylene carbonate can be easily isolated by distillation. The physical and chemical properties of the compound are as follows.
外 観：無色の液体
屈折率：1.4582nD15
比 重：1.061（20℃）
凝固点：−42℃
沸 点：127℃（2.5mmHg）
粘 度：11.58cst（40℃）
2.62cst（100℃）
引火点：170℃
体積抵抗率：２×207Ωcm（20℃）
誘電率：81（1KHz，20℃）
本発明化合物のI.R.分析チヤートを第１図に示
す。 Appearance: Colorless liquid Refractive index: 1.4582nD Specific gravity: 1.061 (20℃) Freezing point: -42℃ Boiling point: 127℃ (2.5mmHg) Viscosity: 11.58cst (40℃) 2.62cst (100℃) Flammability Point: 170°C Volume resistivity: 2×20 7 Ωcm (20°C) Dielectric constant: 81 (1 KHz, 20°C) The IR analysis chart of the compound of the present invention is shown in FIG.
また、本発明化合物のN.M.Rのチヤートを第２
図に示す（レフアレンス：TMS、溶剤：CCl4、
濃度15％）。 In addition, the NMR chart of the compound of the present invention was
As shown in the figure (reference: TMS, solvent: CCl4 ,
concentration 15%).
以下、実施例をあげて本発明を説明する。 The present invention will be explained below with reference to Examples.
実施例 １
トルエン1000mlを10℃以下に保持し、これにホ
スゲン約１モル（100ｇ）を溶解させる。このホ
スゲン溶液を撹拌しながら２，２，４−トリメチ
ル−１，３−ペンタンジオール１モル（146.2
ｇ）を約１時間を要して加え、発生する塩化水素
ガスを系外におい出す。塩化水素ガスが発生しな
くなるまで反応をさらに続ける。反応物を2.5mm
Hgで減圧蒸留し生成物約170ｇ（収率99％）を得
た。Example 1 About 1 mole (100 g) of phosgene is dissolved in 1000 ml of toluene, which is kept at 10° C. or lower. While stirring this phosgene solution, 1 mol of 2,2,4-trimethyl-1,3-pentanediol (146.2
g) is added over a period of about 1 hour, and the generated hydrogen chloride gas is vented out of the system. The reaction is further continued until no hydrogen chloride gas is generated. 2.5mm of reactant
The product was distilled under reduced pressure with Hg to obtain about 170 g of product (yield 99%).
生成物を以下の条件でガスクロマトグラフイー
にかけ、第３図に示すごとき単一のピークが検出
された。生成物の屈折率は1.4582nD15、比重
1.061（20℃）、凝固点−42℃である。I.Rおよび
NMRのチヤートは第１図および第２図に示す。 The product was subjected to gas chromatography under the following conditions, and a single peak as shown in FIG. 3 was detected. The refractive index of the product is 1.4582nD 15 and the specific gravity
1.061 (20℃), freezing point -42℃. IR and
NMR charts are shown in Figures 1 and 2.
ガスクロマトグラフイーの条件： 検出器：FID カラム（ステンレス製）：長さ：１ｍ 充填剤：SE30 キヤリヤーガス：窒素ガス 0.8Kg／cm2 インジエクシヨン温度：211℃ 展開温度 ：160℃ チヤート送り速度 ：５mm／分 Gas chromatography conditions: Detector: FID Column (stainless steel): Length: 1m Packing material: SE30 Carrier gas: Nitrogen gas 0.8Kg/cm 2 Injection temperature: 211℃ Development temperature: 160℃ Chart feed rate: 5mm/min
第１図は１−イソプロピル−２，２−ジメチル
−１，３−プロピレンカーボネートのIRチヤー
ト、第２図は同化合物のNMRチヤート、第３図
は実施例１で得られた生成物のガスクロマトグラ
ムを示す。
Figure 1 is an IR chart of 1-isopropyl-2,2-dimethyl-1,3-propylene carbonate, Figure 2 is an NMR chart of the same compound, and Figure 3 is a gas chromatogram of the product obtained in Example 1. shows.
Claims (1)
ジオールとホスゲンとを、発生する塩酸ガスを系
外に除去しながら脱塩酸反応せしめることによる
1.イソプロピル−２，２−ジメチル−１，３−プ
ロピレンカーボネートの製法。1 By subjecting 2,2,4-trimethyl-1,3-pentanediol and phosgene to a dehydrochloric acid reaction while removing the generated hydrochloric acid gas from the system.
1. Process for producing isopropyl-2,2-dimethyl-1,3-propylene carbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14714081A JPS5849377A (en) | 1981-09-17 | 1981-09-17 | 1-isopropyl-2,2-dimethyl-1,3-propylene carbonate and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14714081A JPS5849377A (en) | 1981-09-17 | 1981-09-17 | 1-isopropyl-2,2-dimethyl-1,3-propylene carbonate and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5849377A JPS5849377A (en) | 1983-03-23 |
| JPS6159635B2 true JPS6159635B2 (en) | 1986-12-17 |
Family
ID=15423476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14714081A Granted JPS5849377A (en) | 1981-09-17 | 1981-09-17 | 1-isopropyl-2,2-dimethyl-1,3-propylene carbonate and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5849377A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT202100031757A1 (en) | 2021-12-20 | 2023-06-20 | Innovativa Srls | MOBILE LIGHTING SYSTEM |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07100702B2 (en) * | 1987-07-22 | 1995-11-01 | 三井石油化学工業株式会社 | Method for producing annular carbonate |
| US5006585A (en) | 1989-09-05 | 1991-04-09 | Huls America Inc. | Stain-resistant plasticizer compositions and method of making same |
-
1981
- 1981-09-17 JP JP14714081A patent/JPS5849377A/en active Granted
Non-Patent Citations (2)
| Title |
|---|
| JOURNAL OF CHEMICAL SOCIETY FARADAY TRANSACTIONS=1971 * |
| JOURNAL OF ORGANIC CHEMISTRY=1959 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT202100031757A1 (en) | 2021-12-20 | 2023-06-20 | Innovativa Srls | MOBILE LIGHTING SYSTEM |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5849377A (en) | 1983-03-23 |
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