JPH02202845A - Production of straight-chain diglycerol - Google Patents
Production of straight-chain diglycerolInfo
- Publication number
- JPH02202845A JPH02202845A JP1023480A JP2348089A JPH02202845A JP H02202845 A JPH02202845 A JP H02202845A JP 1023480 A JP1023480 A JP 1023480A JP 2348089 A JP2348089 A JP 2348089A JP H02202845 A JPH02202845 A JP H02202845A
- Authority
- JP
- Japan
- Prior art keywords
- diglycerol
- compound
- diglycerin
- reaction
- acid
- 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.)
- Pending
Links
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 229940105990 diglycerin Drugs 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 26
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 230000002378 acidificating effect Effects 0.000 abstract description 6
- 238000010992 reflux Methods 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- -1 acetal derivative of diglycerol Chemical class 0.000 abstract description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001728 carbonyl compounds Chemical class 0.000 abstract description 4
- 125000004122 cyclic group Chemical group 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 229920000223 polyglycerol Polymers 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000011187 glycerol Nutrition 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CQBPOPVKDNHISM-UHFFFAOYSA-N propane-1,2,3-triol;propan-2-one Chemical compound CC(C)=O.OCC(O)CO CQBPOPVKDNHISM-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は直鎖状ジグリセリンの製法に関するものである
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing linear diglycerin.
ジグリセリンは、多価アルコールのひとつとして化粧品
の保湿剤、増粘剤などに、また、各種の誘導体、なかで
も界面活性剤の原料として多く使われている。Diglycerin is a polyhydric alcohol that is widely used as a moisturizing agent and thickener in cosmetics, and as a raw material for various derivatives, especially surfactants.
［従来の技術と問題点］ 従来、ジグリセリンはグリセリンの蒸留残分。[Conventional technology and problems] Traditionally, diglycerin is the distillation residue of glycerin.
アルカリ触媒下に高温でグリセリンを縮合させた反応物
、エピハロヒドリンを水酸化ナトリウムで重合させた反
応物などの、ジグリセリンの含有率が２０〜３０％の組
成物を蒸留することによって純度約８０％のものを得て
おり、ジグリセリンの生産量と同量あるいはそれ以上に
副生物であるポリグリセリンが発生するなど、効率の悪
い製造法である。Purity of approximately 80% can be obtained by distilling a composition containing 20 to 30% diglycerin, such as a reaction product in which glycerin is condensed at high temperature under an alkali catalyst or a reaction product in which epihalohydrin is polymerized with sodium hydroxide. This is an inefficient manufacturing method, as the by-product polyglycerin is produced in an amount equal to or greater than the amount of diglycerin produced.
また、上記のいずれの組成物中のジグリセリンも、その
組成物ができる過程における熱重合、エビハロヒドリン
の反応性の強さなどの理由から環状物またはポリグリセ
リンを多く含んだものである。Furthermore, the diglycerin in any of the above compositions contains a large amount of cyclic substances or polyglycerin due to thermal polymerization during the process of making the composition, high reactivity of shrimp halohydrin, etc.
ジグリセリンを、例えば、脂肪酸エステルなどの界面活
性剤の原料として使用する場合には、直鎖状ジグリセリ
ンの含有率が高いほど界面活性能が強いことが知られて
おり、環状物またはポリグリセリンのより少ないものが
求められている。When using diglycerin as a raw material for surfactants such as fatty acid esters, it is known that the higher the content of linear diglycerin, the stronger the surfactant ability. There is a need for fewer of these.
［問題点の解決手段］
本発明者らは、上記の問題点を解決すべく鋭意検討を重
ねた結果、グリセリンを出発原料とした場合の縮合反応
は逐次的に進むため、−度生成されたジグリセリンとグ
リセリンの反応が起こり、ジグリセリンのみを効率良く
合成することは不可能であることを解明し、グリセリン
のもつ３個の水酸基のうち１．２位の水酸基を保護して
化合物（Ａ’）とし、これを酸またはアルカリ触媒下で
縮合させ、引き続いてこれを酸加水分解することにより
、ジグリセリンを得ることに成功し、本発明を完成した
。[Means for Solving the Problems] As a result of intensive studies to solve the above problems, the present inventors found that since the condensation reaction when glycerin is used as a starting material proceeds sequentially, - It was discovered that a reaction between diglycerin and glycerin occurs, and that it is impossible to efficiently synthesize diglycerin alone. '), condensed this under an acid or alkali catalyst, and then acid-hydrolyzed it, thereby successfully obtaining diglycerin and completing the present invention.
本発明の製法を具体的に説明すると、公知の方法により
、酸性触媒下でグリセリンと各種のカルボニル化合物を
反応させて化合物（Ａ）をつくり、化合物（Ａ）に触媒
をｏ、ｏｏｉ％〜５．０重量％、好ましくは０．５〜１
．０重量％添加して、化合物（Ａ）の沸点近くの温度で
加熱、還流させながら、生成水のみを留去しつつ反応さ
せて、ジグリセリンのアセタール誘導体とする。生成水
の留出が止まった時点で、反応系を減圧にして未反応の
化合物（Ａ）を留出させる。この回収した化合物（Ａ）
は再使用できる。反応終了後、冷却し、これを酸性水溶
液中に入れて加熱し、アセタール結合を開裂させてジグ
リセリンとする。次に、このものをアルカリで中和した
後、−船釣に行われるような活性炭処理、およびイオン
交換樹脂処理にて精製し、脱水濃縮して高品質のジグリ
セリンを得る。To specifically explain the production method of the present invention, compound (A) is prepared by reacting glycerin with various carbonyl compounds under an acidic catalyst, and a catalyst is added to compound (A) at o, ooi% to 5%. .0% by weight, preferably 0.5-1
．． 0% by weight is added, and while heating and refluxing at a temperature near the boiling point of compound (A), the reaction is carried out while distilling off only the produced water to obtain an acetal derivative of diglycerin. When distillation of the produced water stops, the reaction system is reduced in pressure to distill off unreacted compound (A). This recovered compound (A)
can be reused. After the reaction is completed, the mixture is cooled, placed in an acidic aqueous solution, and heated to cleave the acetal bond to produce diglycerin. Next, this product is neutralized with an alkali, and then purified by activated carbon treatment and ion exchange resin treatment similar to those used in boat fishing, followed by dehydration and concentration to obtain high-quality diglycerin.
こうして得られたジグリセリンは、極少量の未反応グリ
セリンを含むが、環状および分岐状ジグリセリンおよび
ポリグリセリンの量は痕跡程度かまたは全く含まないも
のである。The diglycerol thus obtained contains very small amounts of unreacted glycerin, but only traces or no amounts of cyclic and branched diglycerols and polyglycerols.
本発明に用いる化合物（Ａ）は、公知の方法により、酸
性触媒下でグリセリンと各種のカルボニル化合物からつ
くられるが、使用されるカルポール化合物は、アルデヒ
ド類としては、ホルムアルデヒド、アセトアルデヒド、
シクロヘキシルアルデヒド、ベンゾアルデヒド、ナフチ
ルアルデヒドなどがあり、ケトン類としてはアセトン、
メチルエチルケトン、メチルイソブチルケトン、シクロ
ヘキサノン、アセトフェノン、ベンゾフェノンなどが挙
げられる。Compound (A) used in the present invention is produced from glycerin and various carbonyl compounds under an acidic catalyst by a known method, and the carpol compounds used include formaldehyde, acetaldehyde,
Examples of ketones include cyclohexylaldehyde, benzaldehyde, naphthylaldehyde, and acetone.
Examples include methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, acetophenone, and benzophenone.
本発明の製法での触媒としては、酸触媒またはアルカリ
触媒のいずれでもよい。、アルカリ触媒としては、水酸
化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸
カリウムなどがよい。酸触媒としては、塩化アルミラム
、四塩化スズ、ｐ−トルエンスルホン酸などがよい。The catalyst used in the production method of the present invention may be either an acid catalyst or an alkali catalyst. As the alkali catalyst, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. are preferable. Preferred acid catalysts include aluminum chloride, tin tetrachloride, and p-toluenesulfonic acid.
本発明の縮合反応温度は、化合物（Ａ）の沸点によって
異なるが、１５０〜２００℃の範囲である。The condensation reaction temperature of the present invention varies depending on the boiling point of compound (A), but is in the range of 150 to 200°C.
［発明の効果］
本発明の製法では、環状および分岐状のジグリセリンお
よびポリグリセリンをほとんど含まないジグリセリンが
得られ、脂肪酸エステルなどの界面活性剤原料として使
用すれば界面活性能の優れたものを造ることができる。[Effects of the Invention] The production method of the present invention yields diglycerin containing almost no cyclic or branched diglycerin or polyglycerin, which has excellent surfactant properties when used as a raw material for surfactants such as fatty acid esters. can be built.
以下に実施例をあげて説明するが、本発明はこれに限定
されるものではない。Examples will be described below, but the present invention is not limited thereto.
［実施例］
実施例１
攪はん機、温度計、還流冷却器を備えた反応容器にアセ
トングリセリン９２４’ｇ（７モル）、水酸化ナトリウ
ム５ｇを仕込み、１９０℃に昇温し、同温度で１０時間
反応させた後、ｌｏｏｍｍＨｇの減圧にして未反応アセ
トングリセリンを留出させた。留出量は３５ｇであった
。[Example] Example 1 924'g (7 mol) of acetone glycerin and 5g of sodium hydroxide were placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux condenser, and the temperature was raised to 190°C. After reacting for 10 hours, the pressure was reduced to room Hg to distill off unreacted acetone glycerin. The distilled amount was 35g.
攪はん機、温度計、還流冷却器を備えた反応容器に、こ
の反応物８８８ｇと０．１重量％の硫酸水溶液１５００
ｇを入れて８０〜９０℃に加温し。888 g of this reactant and 1500 g of a 0.1% by weight aqueous sulfuric acid solution were placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux condenser.
Add g and warm to 80-90℃.
４時間攪はんした。終了後、１０％水酸化ナトリウム水
溶液でｐ Ｈ６に調整したのち、温度８０〜９０℃、真
空度６０ ｍ ｍ Ｈｇにて、５００ｇのアセトンまた
は水を留去した。It was stirred for 4 hours. After the completion of the reaction, the pH was adjusted to 6 with a 10% aqueous sodium hydroxide solution, and then 500 g of acetone or water was distilled off at a temperature of 80 to 90° C. and a degree of vacuum of 60 mm Hg.
このものを５０〜６０℃に冷却して粉末活性炭５ｇを添
加し、同温度で３０分間攪はん後、ろ過した。このろ液
を■１型強酸性イオン交換樹脂とＯＨ型塩基性イオン交
換樹脂が容量比で１＝２である混床塔に空間速度２で通
液した。処理液は温度１−００℃、真空度５ ｍ ｒｎ
Ｈｇの条件で脱水して。This product was cooled to 50 to 60°C, 5 g of powdered activated carbon was added, stirred at the same temperature for 30 minutes, and then filtered. This filtrate was passed at a space velocity of 2 through a mixed bed column (1) containing a 1-type strongly acidic ion exchange resin and an OH-type basic ion exchange resin in a volume ratio of 1=2. The processing liquid has a temperature of 1-00℃ and a vacuum level of 5 mrn.
Dehydrated under Hg conditions.
ジグリセリン８４５ｇを得た。その結果を第１表に示す
。845 g of diglycerin was obtained. The results are shown in Table 1.
比較例１
攪はん機、温度計、還流冷却器を備えた反応容器にアセ
トングリセリン５２８ｇ （４モル）、グリセリン３６
８ｇ （４モル）、水酸化ナトリウム５ｇを仕込み、以
下、実施例１と同様に操作してジグリセリンを得た。そ
の結果を第１表に示す。Comparative Example 1 In a reaction vessel equipped with a stirrer, a thermometer, and a reflux condenser, 528 g (4 moles) of acetone glycerin and 36 g glycerin were added.
8 g (4 moles) and 5 g of sodium hydroxide were charged, and the following procedure was carried out in the same manner as in Example 1 to obtain diglycerin. The results are shown in Table 1.
比較例２
攪はん機、温度計、窒素ガス吹き込み管、還流冷却器を
備えた反応容器に、グリセリン９２０ｇ（１０モル）、
水酸化ナトリウム５ｇを仕込み、２５０℃に昇温しで、
同温度で加熱し、グリセリンがジグリセリンとなる理論
値から求めた理論生成水９０ｇ（５モル）が留出した時
点を終点とした。以下、実施例１の精製法と同様に操作
してジグリセリンを得た。その結果を第１表に示す。Comparative Example 2 In a reaction vessel equipped with a stirrer, a thermometer, a nitrogen gas blowing tube, and a reflux condenser, 920 g (10 moles) of glycerin,
Add 5g of sodium hydroxide and raise the temperature to 250℃.
The end point was determined by heating at the same temperature and distilling 90 g (5 mol) of theoretically produced water, which was determined from the theoretical value at which glycerin turned into diglycerin. Thereafter, the same purification method as in Example 1 was performed to obtain diglycerin. The results are shown in Table 1.
１」Ｌ−
（注１）トリメチルシリル化したもののガスクロマトグ
ラフィー分析による組成。1"L- (Note 1) Composition of trimethylsilylated product as determined by gas chromatography analysis.
Claims (1)
縮合させることを特徴とする直鎖状ジグリセリンの製法
。 ▲数式、化学式、表等があります▼（Ａ） （Ｒ＿１、Ｒ＿２は水素または炭素数１〜１２のアルキ
ル基、アリール基またはアラルキル基である。）[Scope of Claims] A method for producing linear diglycerin, which comprises condensing a compound represented by the following general formula (A) under an acid or alkali catalyst. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(A) (R_1 and R_2 are hydrogen or an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1023480A JPH02202845A (en) | 1989-01-31 | 1989-01-31 | Production of straight-chain diglycerol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1023480A JPH02202845A (en) | 1989-01-31 | 1989-01-31 | Production of straight-chain diglycerol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02202845A true JPH02202845A (en) | 1990-08-10 |
Family
ID=12111692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1023480A Pending JPH02202845A (en) | 1989-01-31 | 1989-01-31 | Production of straight-chain diglycerol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02202845A (en) |
-
1989
- 1989-01-31 JP JP1023480A patent/JPH02202845A/en active Pending
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