JPH01165582A - Production of glycerolcarbonate - Google Patents
Production of glycerolcarbonateInfo
- Publication number
- JPH01165582A JPH01165582A JP62322807A JP32280787A JPH01165582A JP H01165582 A JPH01165582 A JP H01165582A JP 62322807 A JP62322807 A JP 62322807A JP 32280787 A JP32280787 A JP 32280787A JP H01165582 A JPH01165582 A JP H01165582A
- Authority
- JP
- Japan
- Prior art keywords
- epichlorohydrin
- carbonate
- reaction
- mol
- basic catalyst
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- AOBOXSNTOBSLGL-UHFFFAOYSA-N 2,3-dihydroxypropyl hydrogen carbonate Chemical compound OCC(O)COC(O)=O AOBOXSNTOBSLGL-UHFFFAOYSA-N 0.000 title 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 235000015497 potassium bicarbonate Nutrition 0.000 claims abstract description 9
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims abstract description 9
- 239000011736 potassium bicarbonate Substances 0.000 claims abstract description 9
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims abstract description 9
- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims abstract description 7
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 3
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 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 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- -1 alkali metal bicarbonate salt Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000006757 chemical reactions by type Methods 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical compound CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、エピクロルヒドリンと炭酸水素ナトリウムま
たは炭酸水素カリウムからグリセロールカーボネートを
製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing glycerol carbonate from epichlorohydrin and sodium bicarbonate or potassium bicarbonate.
本発明で見られるグリセロールカーボネートは、ジイソ
シアネートあるいはインシアネート末端プレポリマーと
反応させて環状カーボネート末端プレポリマーとし該プ
レポリマーとポリアミン化合物の２液反応型として、塗
料、接着剤、各種バインダー、各種成型品など極めて広
い応用分野かある。The glycerol carbonate seen in the present invention is reacted with a diisocyanate- or incyanate-terminated prepolymer to form a cyclic carbonate-terminated prepolymer.As a two-component reaction type of the prepolymer and a polyamine compound, it can be used in paints, adhesives, various binders, and various molded products. There are extremely wide application fields such as
従来のグリセロールカーボネートの製造法は、グリセリ
ンとジアルキルカーボネートあるいは、アルキレフカー
ボネートの反応によるものでめった。グリセリンとジア
ルキルカーボネートによる反応は、グリセロールカーボ
ネートの収率が低く、また副生成物としてジグリ七ロー
ルカーボネートのような多量体が出来ること、反応生成
物に未反応のグリセリンや副生成物があるため、これら
の蒸留による除去が困難であることなどの欠点があった
。The conventional method for producing glycerol carbonate was based on the reaction of glycerin and dialkyl carbonate or alkylev carbonate, which was unsuccessful. The reaction between glycerin and dialkyl carbonate has a low yield of glycerol carbonate, and a multimer such as digly7ol carbonate is produced as a by-product, and the reaction product contains unreacted glycerin and by-products. There were drawbacks such as difficulty in removing these by distillation.
また、グリセリンとアルキレフカーボネートによる反応
でも同様な問題点がある。グリセロールカーボネートは
１８０℃以上で脱炭酸によシグリシドールに変化するの
で、反応生成物系を蒸留によりグリセロールカーボネー
トを留出させて分離することは収率の大幅低下をもたら
し好ましくないなどの欠点がめった。Similar problems also arise in the reaction between glycerin and alkylev carbonate. Glycerol carbonate changes to siglycidol by decarboxylation at temperatures above 180°C, so separating the reaction product system by distilling the glycerol carbonate rarely results in a significant drop in yield and is undesirable. .
本発明者は、生成物の分離法が簡単で、副反応のすくな
い、収率の高いグリセロールカーボネートの製造方法に
ついて鋭意研究した結果、エピクロルヒドリンと炭酸水
素アルカリ金属塩を使用することによシ解決できること
を見出し本発明に至った。As a result of intensive research into a method for producing glycerol carbonate with a simple product separation method, fewer side reactions, and a high yield, the present inventor found that the problem can be solved by using epichlorohydrin and an alkali metal bicarbonate salt. This discovery led to the present invention.
即ち、本発明は、エピクロルヒドリン１．０モルと炭酸
水素ナトリウムまたは炭酸水素カリウム０３８〜２．０
モルを塩基性触媒の存在下で反応せしめることを特徴と
するグリセロールカーボネートの製造方法である。That is, the present invention provides 1.0 mol of epichlorohydrin and 0.38 to 2.0 mol of sodium bicarbonate or potassium bicarbonate.
This is a method for producing glycerol carbonate, which is characterized by reacting mol of glycerol carbonate in the presence of a basic catalyst.
本発明による反応生成物系にはグリセロールカーボネー
トのほかに未反応のエピクロルヒドリンと塩化ナトリウ
ムまたは塩化カリウムが存在するので、反応後、ろ過に
より塩化物を除去し、さらにエピクロルヒドリンをロー
タリーエバポレーターで７０℃ １０〜２０ｍ１１Ｈｆ
の条件で留去した。この簡単な分離法により収率８５％
以上、純度９０％以上のグリセロールカーボネートをう
ろことが出来る。Since the reaction product system according to the present invention contains unreacted epichlorohydrin and sodium chloride or potassium chloride in addition to glycerol carbonate, after the reaction, the chloride is removed by filtration, and the epichlorohydrin is heated in a rotary evaporator at 70° C. 20m11Hf
It was distilled off under the following conditions. This simple separation method yields 85%
As described above, it is possible to produce glycerol carbonate with a purity of 90% or more.
本発明の反応は、下式（１）のような経路をとるものと
思われる。（但し式中のＭｅはＮａ ｉたはＫ）Ｍｅ
−） ＣＨ，ＣＨＣＨ，ＯＨ＋ ＭｅＣｌ、、、、、−
・・−・−・（１）本発明で用いる原料のエピクロルヒ
ドリン、炭酸水素ナトリウム、炭酸水素カリウムなどは
、−般に商業的に使われているものでよい。The reaction of the present invention seems to take a route as shown in the following formula (1). (However, Me in the formula is Na i or K)Me −) CH, CHCH, OH+ MeCl, ,,, −
(1) The raw materials such as epichlorohydrin, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. used in the present invention may be those commonly used commercially.
本発明で用いる塩基性触媒は、すべての塩基性触媒が使
用出来るが、特にトリエチルアミン、ジエチルシクロヘ
キシルアミンのような３級アルキル、アミンで低沸点の
化合物が好ましい。塩基性触媒の添加蓋は触媒の塩基性
により異なるが、エピクロルヒドリンに対して０．１〜
１０重量％が好ましい。As the basic catalyst used in the present invention, any basic catalyst can be used, but tertiary alkyl or amine compounds having a low boiling point such as triethylamine and diethylcyclohexylamine are particularly preferred. The addition cap for the basic catalyst varies depending on the basicity of the catalyst, but it is 0.1 to 0.1 for epichlorohydrin.
10% by weight is preferred.
本発明で用いるエピクロルヒドリンと炭酸水素ナトリウ
ムまたはカリウムの仕込比は、エピクロルヒドリン１．
０モルに対して炭酸水素ナトリウムまたはカリウムを０
．８〜２．０モルの範囲で仕込むのが好ましい。０．８
モル未満の場合は、反応生成物系に未反応のエピクロル
ヒドリンが多く含まれグリセロールカーボネートの収率
を低下させるので好ましくない。また、２．０モルを超
える場合は未反応の炭酸水素ナトリウムまたはカリウム
が反応生成物系に残り経済的に好ましくない。The charging ratio of epichlorohydrin and sodium or potassium hydrogen carbonate used in the present invention is 1.
0 mol of sodium bicarbonate or potassium
．． It is preferable to charge in a range of 8 to 2.0 moles. 0.8
If it is less than mol, the reaction product system will contain a large amount of unreacted epichlorohydrin, which will reduce the yield of glycerol carbonate, which is not preferable. Moreover, if it exceeds 2.0 mol, unreacted sodium or potassium hydrogen carbonate remains in the reaction product system, which is economically unfavorable.
本発明の反応は、常圧で５０〜１００’Ｃの条件で行う
ことができる。反応終了はＩＲを用い、エピクロルヒド
リンの吸収帯の一つである１２７０Ｃｍ−１の吸光度の
減少速度から判断することが出来る。反応終了後は、副
生成物である塩化ナトリウムまたはカリウムおよび未反
応の炭酸水素ナトリウムまたはカリウムを吸引ろ過によ
り除去し、次いでろ過液を５０〜７０°Ｃ１１５〜４０
ｍＮ Ｈｆの真空蒸留により未反応のエピクロルヒド
リンおよび塩基性触媒を除去し、グリセロールカーボネ
ートを得る。The reaction of the present invention can be carried out under conditions of normal pressure and 50 to 100'C. The completion of the reaction can be determined using IR from the rate of decrease in absorbance at 1270 Cm-1, which is one of the absorption bands of epichlorohydrin. After the reaction is complete, by-products sodium or potassium chloride and unreacted sodium or potassium hydrogen carbonate are removed by suction filtration, and the filtrate is heated at 50 to 70°C at 115 to 40°C.
Unreacted epichlorohydrin and basic catalyst are removed by vacuum distillation of mN Hf to obtain glycerol carbonate.
さらに、高純度のグリセロールカーボネートを必要とす
る場合は、見られたグリセロールカーボネートを１２０
〜１３０℃、１〜３ＮＮＨｆｌの真空蒸留により留出さ
せてうろことが出来る。Additionally, if you require high purity glycerol carbonate, you can convert the found glycerol carbonate to 120
It can be distilled off by vacuum distillation at ~130°C and 1-3 NNHfl.
本発明で見られるグリセロールカーボネートは、ジイソ
シアネートするいはインシアネート末端プレポリマーと
反応させて環状カーボネート末端プレポリマーとし、ポ
リアミン化合物で硬化させてヒドロキシウレタンポリマ
ーを生成させることが出来る。The glycerol carbonate found in this invention can be reacted with a diisocyanate or inocyanate terminated prepolymer to form a cyclic carbonate terminated prepolymer and cured with a polyamine compound to form a hydroxyurethane polymer.
この環状カーボネート末端プレポリマーとポリアミンに
よるウレタンポリマーは、通常のポリイソシアネートと
ポリオールによる反応にくらべ、湿気とか水分の影響を
全く受けず、従って見られたポリマーは気泡を含まない
という特徴を有している。また、環状カーボネートとア
ミンの反応は、エボキ７化合物とアミンの反応に似てい
るので、プリプレグを経由した樹脂化が可能であるとい
う特徴がある。This urethane polymer made from a cyclic carbonate-terminated prepolymer and a polyamine is completely unaffected by moisture or moisture compared to the reaction made from a normal polyisocyanate and a polyol, and therefore the observed polymer has the characteristic of not containing air bubbles. There is. Furthermore, since the reaction between a cyclic carbonate and an amine is similar to the reaction between an EBOKI 7 compound and an amine, it is characterized in that it can be converted into a resin via a prepreg.
環状カーボネート末端プレポリマーとポリアミン化合物
の２液反応型として、塗料、接着剤、各種バインダー、
各椙成型品など極めて広い応用分野がある。As a two-component reaction type of cyclic carbonate-terminated prepolymer and polyamine compound, it can be used for paints, adhesives, various binders,
It has a wide range of applications, including molded products.
次に本発明について実施例を挙げて説明する。 Next, the present invention will be explained by giving examples.
実施例１゜
５００ｍ１の四つロセバラプルフラスコに攪拌機、冷却
塔、温度計を付け、エピクロルヒドリン（試薬） １８
５．９ （、２，０モル）、炭酸水素す） ＩＪウム（
試薬）１６８９ （２，０モル）、およびトリエチルア
ミン（試薬）５．４ｇを仕込んで攪拌する。オイルバス
により７０℃に加温し、１６時間反応させ、ＩＲで１２
７０ｃｍ ”のエピクロルヒドリンの吸収帯がこれ以上
減少しないことを確認して反応を終了させた、反応液を
真空ろ過によりろ過し１次いでろ液をロータリーエバポ
レーターによシフ０℃、１５１１１Ｈｐで未反応のエピ
クロルヒドリンとトリエチルアミンを除去し、りＩＪセ
ロールカーボネート２０５ｇをえた。この収率はエピク
ロルヒドリンをベースにして８６．９％であった。生成
物の塩基分を測定すると２．７％であった。塩基分はα
モノクロルヒドリンに由来すると仮定するとこのグリセ
ロールカーボネートの純度は９２チであった。Example 1 A 500 ml four rosette flask was equipped with a stirrer, a cooling tower and a thermometer, and epichlorohydrin (reagent) 18
5.9 (2,0 mol), hydrogen carbonate)
Reagent) 1689 (2.0 mol) and triethylamine (reagent) 5.4g were charged and stirred. Heated to 70℃ in an oil bath, reacted for 16 hours, and
The reaction was terminated after confirming that the epichlorohydrin absorption band at 70 cm" did not decrease any further. The reaction solution was filtered by vacuum filtration, and the filtrate was then transferred to a rotary evaporator to remove unreacted epichlorohydrin at 0°C and 15111 HP. and triethylamine were removed to obtain 205 g of ReIJ cerol carbonate.The yield was 86.9% based on epichlorohydrin.The base content of the product was determined to be 2.7%.Base content is α
Assuming that it was derived from monochlorohydrin, the purity of this glycerol carbonate was 92%.
実施例２゜
実施例１と同様の装置にエピクロルヒドリン（試薬）１
８５ｇ（２，０モル）、炭酸水素カリウム（試薬）２５
０ｇ（２，５モル）およびトリエチルアミン（試薬）５
．４．９を仕込んで実施例１と同じ条件で反応させた。Example 2゜In the same apparatus as in Example 1, 1 part of epichlorohydrin (reagent) was added.
85 g (2.0 mol), potassium hydrogen carbonate (reagent) 25
0 g (2,5 mol) and triethylamine (reagent) 5
．． 4.9 was charged and reacted under the same conditions as in Example 1.
反応液の処理を実施例１と同じ様にしてグリセロールカ
ーボネート２１２ｇをえた。収率はエピクロルヒドリン
をベースにして８９．８％、塩基分から出した純度は９
１チであった。The reaction solution was treated in the same manner as in Example 1 to obtain 212 g of glycerol carbonate. The yield is 89.8% based on epichlorohydrin, and the purity from the base is 9.
It was 1ch.
比較較１゜
５００ ｍｌの四つロセパラブルフラスコに攪拌機、温
度計、留出塔を付け、グリセリン（試薬）１３６ｇ（１
，５モル）、ジエチルカーボネート（試薬）２６２ｇ（
２，２モル）、炭酸ソーダ１．９ｇを仕込み、オイルバ
スで９０−１００’ＣＩ４時間反応させた。この間副生
成物のエタノールを留出塔から留去した。系を減圧にし
、未反応のジエチルカーボネートを留去し、反応生成物
１６２ｇをえた。これには未反応のグリセリンが含まれ
ているので、酢酸エチル１００−で３回抽出し、酢酸エ
チル溶液から酢酸エチルを留去シてグリセロールカーボ
ネー）１１０．ｊｉ＋をえた。Comparison 1. A 500 ml four-piece removable flask was equipped with a stirrer, a thermometer, and a distillation column, and 136 g of glycerin (reagent) (1
, 5 mol), diethyl carbonate (reagent) 262 g (
2.2 mol) and 1.9 g of soda carbonate were added and reacted in an oil bath for 4 hours at 90-100'CI. During this time, the by-product ethanol was distilled off from the distillation column. The pressure of the system was reduced and unreacted diethyl carbonate was distilled off to obtain 162 g of a reaction product. Since this contains unreacted glycerin, it was extracted three times with 100% ethyl acetate, and the ethyl acetate was distilled off from the ethyl acetate solution (110% glycerol carbonate). I got ji+.
これはグリセリンをベースにして６３％の収率であった
。This was a 63% yield based on glycerin.
本発明の製造方法によれば、簡単な製造方法で、収率よ
く、高純度品を安価に得ることができる。According to the production method of the present invention, a highly purified product can be obtained in good yield and at low cost using a simple production method.
Claims (1)
たは炭酸水素カリウム０．８〜２．０モルを塩基性触媒
の存在下で反応せしめることを特徴とするグリセロール
カーボネートの製造方法。A method for producing glycerol carbonate, which comprises reacting 1.0 mol of epichlorohydrin with 0.8 to 2.0 mol of sodium hydrogen carbonate or potassium hydrogen carbonate in the presence of a basic catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62322807A JPH064620B2 (en) | 1987-12-22 | 1987-12-22 | Method for producing glycerol carbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62322807A JPH064620B2 (en) | 1987-12-22 | 1987-12-22 | Method for producing glycerol carbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01165582A true JPH01165582A (en) | 1989-06-29 |
| JPH064620B2 JPH064620B2 (en) | 1994-01-19 |
Family
ID=18147844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62322807A Expired - Lifetime JPH064620B2 (en) | 1987-12-22 | 1987-12-22 | Method for producing glycerol carbonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH064620B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5203715A (en) * | 1991-03-13 | 1993-04-20 | Yazaki Corporation | Connector |
| US5279507A (en) * | 1991-09-26 | 1994-01-18 | Yazaki Corporation | Connector for use in vehicles |
| US5507666A (en) * | 1993-12-28 | 1996-04-16 | Yazaki Corporation | Lock securing mechanism for connectors |
| US5554044A (en) * | 1994-07-13 | 1996-09-10 | Sumitomo Wiring Systems, Ltd. | Connector |
| US6309242B1 (en) | 1998-06-22 | 2001-10-30 | Yazaki Corporation | Electrical connector with a coupling state indicating mechanism |
| KR100777009B1 (en) * | 2005-12-30 | 2007-11-28 | 주식회사 케이씨씨 | Polysiloxane having good water-absorption ability and process for preparing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62175477A (en) * | 1986-01-11 | 1987-08-01 | ヘキスト アクチェンゲゼルシャフト | Production of 2-oxo-1, 3-dioxorane |
-
1987
- 1987-12-22 JP JP62322807A patent/JPH064620B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62175477A (en) * | 1986-01-11 | 1987-08-01 | ヘキスト アクチェンゲゼルシャフト | Production of 2-oxo-1, 3-dioxorane |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5203715A (en) * | 1991-03-13 | 1993-04-20 | Yazaki Corporation | Connector |
| US5279507A (en) * | 1991-09-26 | 1994-01-18 | Yazaki Corporation | Connector for use in vehicles |
| US5507666A (en) * | 1993-12-28 | 1996-04-16 | Yazaki Corporation | Lock securing mechanism for connectors |
| US5554044A (en) * | 1994-07-13 | 1996-09-10 | Sumitomo Wiring Systems, Ltd. | Connector |
| US6309242B1 (en) | 1998-06-22 | 2001-10-30 | Yazaki Corporation | Electrical connector with a coupling state indicating mechanism |
| KR100777009B1 (en) * | 2005-12-30 | 2007-11-28 | 주식회사 케이씨씨 | Polysiloxane having good water-absorption ability and process for preparing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH064620B2 (en) | 1994-01-19 |
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