JPH045256A - Production of succinylsuccinic acid diester - Google Patents
Production of succinylsuccinic acid diesterInfo
- Publication number
- JPH045256A JPH045256A JP10775590A JP10775590A JPH045256A JP H045256 A JPH045256 A JP H045256A JP 10775590 A JP10775590 A JP 10775590A JP 10775590 A JP10775590 A JP 10775590A JP H045256 A JPH045256 A JP H045256A
- Authority
- JP
- Japan
- Prior art keywords
- acid diester
- succinic acid
- sulfoxide
- reaction
- solvent
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 7
- 150000005690 diesters Chemical class 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- -1 succinic acid diester Chemical class 0.000 claims abstract description 27
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000001384 succinic acid Substances 0.000 claims abstract description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052751 metal Inorganic materials 0.000 abstract description 8
- 239000002184 metal Substances 0.000 abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007787 solid Substances 0.000 abstract description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012044 organic layer Substances 0.000 abstract description 3
- 239000000049 pigment Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 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 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- WIWJFWANKMRGGS-UHFFFAOYSA-N 3,4-dimethyl-1,6-dioxecane-2,5,7,10-tetrone Chemical compound C1(CCC(=O)OC(C(C(C(=O)O1)C)C)=O)=O WIWJFWANKMRGGS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 1
- BQCCJWMQESHLIT-UHFFFAOYSA-N 1-propylsulfinylpropane Chemical compound CCCS(=O)CCC BQCCJWMQESHLIT-UHFFFAOYSA-N 0.000 description 1
- WFJXYIUAMJAURQ-UHFFFAOYSA-N 2-propan-2-ylsulfinylpropane Chemical compound CC(C)S(=O)C(C)C WFJXYIUAMJAURQ-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- SZHZCPHKDJWHNG-UHFFFAOYSA-N dipropyl butanedioate Chemical compound CCCOC(=O)CCC(=O)OCCC SZHZCPHKDJWHNG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、キナクリドン顔料の中間体として有用なサク
シニルコハク酸ジエステルの製造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 succinyl succinic acid diester useful as an intermediate for quinacridone pigments.
（従来の技術）
サクシニルコハク酸ジエステルの製造法に関しては、古
くから各種の製造法が知られており、例えば特開昭６２
−１０６０６２号公報には、金属アルコラードとともに
、リン酸アミド、リン酸エステルまたは環状Ｎ−アルキ
ルアミド類を添加することによって、目的物のサクシニ
ルコハク酸ジエステル類の収率が向上することが示され
ている。(Prior Art) Regarding the production method of succinyl succinic acid diester, various production methods have been known for a long time, such as JP-A-62
Publication No. 106062 discloses that the yield of the target product, succinyl succinic diesters, is improved by adding phosphoric acid amide, phosphoric ester, or cyclic N-alkylamides together with the metal alcoholade. There is.
（発明が解決しようとする課題）
しかしながら、特開昭６２−１０６０６２号公報に記載
されている方法では、添加剤としてヘキサメチルリン酸
トリアミドが使用されており、比較的良い収率でサクシ
ニルコハク酸ジメチルエステルを得ているが、ヘキサメ
チルリン酸トリアミドは、発ガン性を有していることが
知られており、その使用は不可能である。その他の添加
剤としては、１，３−ジメチル−２−イミダゾリジノン
等の環状Ｎ−アルキルアミド、リン酸アミドおよびリン
酸エステル等が挙げられているが、これらは高価で、し
かも収率が低いため、工業的使用には適していない。(Problems to be Solved by the Invention) However, in the method described in JP-A-62-106062, hexamethylphosphoric acid triamide is used as an additive, and succinyl succinic acid can be obtained in a relatively good yield. Although dimethyl ester has been obtained, hexamethylphosphoric triamide is known to be carcinogenic and its use is impossible. Other additives include cyclic N-alkylamides such as 1,3-dimethyl-2-imidazolidinone, phosphoric acid amides, and phosphoric esters, but these are expensive and have low yields. Due to its low value, it is not suitable for industrial use.
（課題を解決するための手段）
本発明者らは、上記事情に鑑みて、鋭意検討した結果、
塩基とスルホキシド類の存在下、溶媒中においてコハク
酸ジエステルを縮合させると、収率が高く、かつ工業的
に安価にサクシニルコハク酸ジエステルが得られること
を見い出し、本発明を完成するにいたった。(Means for Solving the Problems) In view of the above circumstances, the inventors of the present invention have conducted extensive studies and found that
It was discovered that succinyl succinic acid diester can be obtained in high yield and industrially at low cost by condensing succinic acid diester in a solvent in the presence of a base and sulfoxides, leading to the completion of the present invention.
すなわち本発明は、コハク酸ジエステルを溶媒中におい
て塩基を用いて縮合させるサクシニルコハク酸ジエステ
ルの製造法において、コハク酸ジエステルの縮合をスル
ホキシド類の存在下で行つことを特徴とするサクシニル
コハク酸ジエステルの製造法を提供するものである。That is, the present invention provides a method for producing succinyl succinic acid diester in which a succinic acid diester is condensed using a base in a solvent, which is characterized in that the condensation of the succinic acid diester is carried out in the presence of a sulfoxide. The present invention provides a method for manufacturing.
以下、本発明のサクシニルコハク酸ジエステルの製法に
ついて詳しく説明する。Hereinafter, the method for producing succinyl succinic acid diester of the present invention will be explained in detail.
一般に、原料として用いるコハク酸ジエステルからそれ
ぞれに対応するサクシニルコハク酸ジエステルが得られ
るが、ここで用いるコハク酸ジエステルとしては、例え
ばコハク酸ジメチルエステル、コハク酸ジエチルエステ
ル、コハク酸ジプロピルエステル等のコハク酸ジアルキ
ルエステルが好ましく、キナクリドン顔料の原料として
は、特にコハク酸ジメチルエステルが安価であるため、
工業的には有利である。Generally, the corresponding succinylsuccinic acid diesters are obtained from the succinic diesters used as raw materials, but the succinic diesters used here include, for example, succinic acid diesters such as succinic acid dimethyl ester, succinic acid diethyl ester, and succinic acid dipropyl ester. Acid dialkyl esters are preferred, and dimethyl succinate is particularly inexpensive as a raw material for quinacridone pigments.
It is industrially advantageous.
塩基としては、通常水酸化ナトリウム、水酸化カリウム
等の金属水酸化物、金属ナトリウム、金属カリウム、ナ
トリウムアルコラ−１・、カリウムアルコラード等が用
いられるが、反応の収率が高く、かつ安価である点から
なかでもナトリウムアルコラードが好ましい。As the base, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal sodium, metal potassium, sodium alcohola-1, potassium alcoholade, etc. are usually used, but they have a high reaction yield and are inexpensive. From this point of view, sodium alcoholade is particularly preferred.
塩基として、金属アルコラードを用いる場合、粉末を反
応系に添加する方法、あるいは金属とアルコールを反応
させて調製したものを用いる方法のいずれの方法を用い
ても良い。When a metal alcoholade is used as a base, either a method of adding a powder to the reaction system or a method of using a product prepared by reacting a metal with an alcohol may be used.
塩基の使用量は、原料のコハク酸ジエステル１．０モル
に対して、通常１．０〜２．０モル、好ましくは１．０
〜１． ３モルの範囲内で用いられる。１．０モル未満
では収率が低く、２．０モルより多く用いても収率が向
上することはないので不経済である。The amount of the base used is usually 1.0 to 2.0 mol, preferably 1.0 mol, per 1.0 mol of the raw material succinic acid diester.
~1. It is used within a range of 3 moles. If it is less than 1.0 mol, the yield will be low, and if it is used in excess of 2.0 mol, the yield will not improve, which is uneconomical.
本発明に用いられるスルホキシド類としては、例えばジ
メチルスルホキシド、ジエチルスルホキシド、ジ−ｎ−
プロピルスルホキシド、ジ−イソプロピルスルホキシド
、ジ−ｎ−ブチルスルホキシド等のアルキルスルホキシ
ド類が好ましく、なかでも入手が容易であり、安価とい
う点からジメチルスルホキシドが最も好適である。Examples of the sulfoxides used in the present invention include dimethyl sulfoxide, diethyl sulfoxide, di-n-
Alkyl sulfoxides such as propyl sulfoxide, di-isopropylsulfoxide, and di-n-butyl sulfoxide are preferred, and among them, dimethyl sulfoxide is most preferred because it is easily available and inexpensive.
これらのスルホキシド類の添加量は、原料のコハク酸ジ
エステル１００重量部に対して、通常１０〜１００重量
部、好ましくは１０〜３０重量部の範囲である。The amount of these sulfoxides added is usually 10 to 100 parts by weight, preferably 10 to 30 parts by weight, based on 100 parts by weight of the raw material diester succinate.
反応に用いられる溶媒としては、８０〜１８０°Ｃの沸
点を有し、反応によって生成するアルコールと共沸しな
いものが良い。例えばベンゼン、トルエン、キシレン、
キュメン、メシチレン等の芳香族炭化水素が好ましく、
キシレンが特に好ましい。The solvent used in the reaction is preferably one that has a boiling point of 80 to 180°C and does not azeotrope with the alcohol produced by the reaction. For example, benzene, toluene, xylene,
Aromatic hydrocarbons such as cumene and mesitylene are preferred;
Particularly preferred is xylene.
反応は通常８０〜１８０°Ｃ１好ましくは１００〜１５
０℃の温度で生成するアルコールを留去しながら実施さ
れる。反応終了後、析出したサクシニルコハク酸ジエス
テルの金属塩を希硫酸等の酸を用いて中和し、析出する
固体をを口過、水洗、乾燥して、サクシニルコハク酸ジ
エステルを得ることができる。さらに、四肢から有機層
を分液して溶媒を留去し、析出する固体を乾燥すること
で効率よくサクシニルコハク酸ジエステルが回収できる
。The reaction is usually carried out at 80 to 180°C, preferably 100 to 15°C.
It is carried out at a temperature of 0° C. while distilling off the alcohol formed. After completion of the reaction, the precipitated metal salt of succinyl succinic acid diester is neutralized using an acid such as dilute sulfuric acid, and the precipitated solid is filtered, washed with water, and dried to obtain succinyl succinic acid diester. Furthermore, the succinyl succinic acid diester can be efficiently recovered by separating the organic layer from the limbs, distilling off the solvent, and drying the precipitated solid.
（実施例）
以下、本発明のサクシニルコハク酸ジエステルの製造法
について、実施例および比較例を示して具体的に説明す
るが、以下の実施例は本発明の方法を限定するものでは
ない。(Examples) Hereinafter, the method for producing succinyl succinic acid diester of the present invention will be specifically explained by showing Examples and Comparative Examples, but the following Examples do not limit the method of the present invention.
なお、収率は使用されたコハク酸ジエステルに対する収
率（モル％）を示す。また、その他の％は特に断りのな
い限り重量％を示す。Note that the yield indicates the yield (mol %) based on the succinic acid diester used. In addition, other percentages indicate weight percentages unless otherwise specified.
実施例１
５００ｍｌの４つロフラスコにナトリウムメチラートの
２８％メタノール溶液７８．１ｇ（０，４１モル）、ジ
メチルスルホキシド１０．０ｇおよびキシレン２００ｇ
を入れた。この混合物を１２０°Ｃに加熱し、コハク酸
ジメチルエステル５４．８ｇ （０，３８モル）を３０
分かけて滴下した後、１２０°Ｃに１時間加熱して反応
させた。反応終了後、反応液の温度を３０°Ｃ以下に保
ちながら３０％希硫酸水溶液６６．３ｇを徐々に滴下し
て中和を行った。析出した固体をろ過、水洗さらに乾燥
して、サクシニルコハク酸ジメチルエステル３３．４ｇ
を得た。さらに、口演を分液し、有機層から溶媒を留去
して、サクシニルコハク酸ジメチルエステル４．８ｇを
得た。得られたサクシニルコハク酸ジメチルエステルの
合計量は、３８．２ｇ（収率８９．５モル％）であった
。Example 1 78.1 g (0.41 mol) of a 28% methanol solution of sodium methylate, 10.0 g dimethyl sulfoxide and 200 g xylene are placed in a 500 ml four-loaf flask.
I put it in. The mixture was heated to 120 °C and 54.8 g (0.38 mol) of dimethyl succinate was added to 30
After the mixture was added dropwise over several minutes, the mixture was heated to 120°C for 1 hour to react. After the reaction was completed, 66.3 g of a 30% dilute sulfuric acid aqueous solution was gradually added dropwise to the reaction solution while keeping the temperature of the reaction solution below 30° C. for neutralization. The precipitated solid was filtered, washed with water, and dried to obtain 33.4 g of dimethyl succinyl succinate.
I got it. Furthermore, the liquid was separated and the solvent was distilled off from the organic layer to obtain 4.8 g of dimethyl succinyl succinate. The total amount of succinyl succinic acid dimethyl ester obtained was 38.2 g (yield: 89.5 mol%).
実施例２
ナトリウムメチラートの２８％メタノール溶液７８．１
ｇ （０，４１モル）の代わりに粉末ナトリウムメチ
ラート１８．７ｇ（０，４１モル）を用いり以外は実施
例１と同様にして、サクシニルコハク酸ジメチルエステ
ルを得た。収率は８９．３モル％であった。Example 2 28% methanol solution of sodium methylate 78.1
Dimethyl succinyl succinate was obtained in the same manner as in Example 1, except that 18.7 g (0.41 mol) of powdered sodium methylate was used instead of 18.7 g (0.41 mol) of powdered sodium methylate. The yield was 89.3 mol%.
実施例３〜５
添加剤として用いたジメチルスルホキシドの量を第１表
に示す量に変更した以外は実施例１と同様にして、サク
シニルコハク酸ジメチルエステルを得た。収率を第１表
に示す。Examples 3 to 5 Succinyl succinic acid dimethyl ester was obtained in the same manner as in Example 1, except that the amount of dimethyl sulfoxide used as an additive was changed to the amount shown in Table 1. The yields are shown in Table 1.
第 １ 表
比較例１
キシレン２５０ｇおよび金属ナトリウム１２．１ｇを１
０５°Ｃに加熱し、Ｎ２気流下金属ナトリウムを分散さ
せメチルアルコール２７．２ｇを徐々に滴下し、さらに
１０５°Ｃに１時間加熱してナトリウムを溶解させた。Table 1 Comparative Example 1 250 g of xylene and 12.1 g of metallic sodium were added to 1
The mixture was heated to 05°C, metal sodium was dispersed under a N2 stream, 27.2g of methyl alcohol was gradually added dropwise, and the mixture was further heated to 105°C for 1 hour to dissolve the sodium.
次に、１，３−ジメチル−２−イミダゾリジノン２０ｇ
を添加し、次にコノλり酸ジメチルエステル７３ｇを加
え１２０°Ｃで４時間加熱した。Next, 20 g of 1,3-dimethyl-2-imidazolidinone
was added, and then 73 g of cono-lambda phosphoric acid dimethyl ester was added and heated at 120°C for 4 hours.
以下、実施例１と同様に後処理を実施して、サクシニル
コハク酸ジメチルエステル９５．３ｇ（収率７８．５モ
ル％）を得た。Thereafter, post-treatment was performed in the same manner as in Example 1 to obtain 95.3 g (yield: 78.5 mol%) of dimethyl succinyl succinate.
（発明の効果）
本発明の製造方法は、収率が高く、かつ工業的に安価に
サクシニルコハク酸ジエステルが得られるという利点が
ある。(Effects of the Invention) The production method of the present invention has the advantage that the yield is high and succinyl succinic acid diester can be obtained industrially at low cost.
Claims (1)
縮合させるサクシニルコハク酸ジエステルの製造法にお
いて、コハク酸ジエステルの縮合をスルホキシド類の存
在下で行うことを特徴とするサクシニルコハク酸ジエス
テル類の製造法。 ２、スルホキシド類が、アルキルスルホキシド類である
請求項１記載の製造法。 ３、スルホキシド類が、ジメチルスルホキシドである請
求項１記載の製造法。[Claims] 1. A method for producing succinyl succinic acid diester in which succinic acid diester is condensed using a base in a solvent, characterized in that the condensation of succinic acid diester is carried out in the presence of sulfoxides. Method for producing acid diesters. 2. The manufacturing method according to claim 1, wherein the sulfoxide is an alkyl sulfoxide. 3. The manufacturing method according to claim 1, wherein the sulfoxide is dimethyl sulfoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10775590A JPH045256A (en) | 1990-04-24 | 1990-04-24 | Production of succinylsuccinic acid diester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10775590A JPH045256A (en) | 1990-04-24 | 1990-04-24 | Production of succinylsuccinic acid diester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH045256A true JPH045256A (en) | 1992-01-09 |
Family
ID=14467159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10775590A Pending JPH045256A (en) | 1990-04-24 | 1990-04-24 | Production of succinylsuccinic acid diester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH045256A (en) |
-
1990
- 1990-04-24 JP JP10775590A patent/JPH045256A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009529025A (en) | Branched carboxylic acid diester | |
| FI63927C (en) | FOERFARANDE FOER FRAMSTAELLNING AV DI-N-PROPYL-AETTIKSSYRA OCHDESS SALTER | |
| US20100312015A1 (en) | Curcumin synthesis | |
| JP5390800B2 (en) | Method for producing toluidine compound | |
| JPH0258272B2 (en) | ||
| JPH045256A (en) | Production of succinylsuccinic acid diester | |
| JPH0647568B2 (en) | Method for producing 2,4-dichloro-5-fluorobenzoic acid | |
| KR20000029594A (en) | Process for preparing substituted valine amide derivatives | |
| CA1042896A (en) | Process for the manufacture of 5-sulfamoyl-anthranilic acids | |
| JP2927880B2 (en) | Method for producing 4,4'-dihydroxy-3,3 ', 5,5'-tetramethyldiphenylmethane | |
| JP2747519B2 (en) | Fluorinated aromatic dicarboxylic acid | |
| JP7263350B2 (en) | Process for preparing acylated amphetamine derivatives | |
| JP2002155058A (en) | Method for producing 1-substituted hydratoin compound | |
| JPH04210660A (en) | Production of dibenzoyl methane | |
| JPH0147475B2 (en) | ||
| JPH0321538B2 (en) | ||
| JPS5819665B2 (en) | Succinyl succinate diester | |
| HU195758B (en) | Process for production of 2,3,4,5-tetrafluor-benzoilacetates | |
| JP3876933B2 (en) | Method for producing hydrogen sulfate ester | |
| JP4329325B2 (en) | Process for producing monoalkali metal salt of diallyl cyanurate | |
| JPS59225147A (en) | Preparation of o-substituted-hydroxylamine | |
| JP2846688B2 (en) | Method for producing low-colored sulfonated α, β unsaturated carboxylic anhydride | |
| GB1583363A (en) | Amphoteric fluorinated sulphonamides | |
| JP2759087B2 (en) | Purification method of 1,4-dihydroxy-2-naphthoic acid aryl ester | |
| KR800000746B1 (en) | Process for the preparation of 5-sulfamoyl-anthranilic acids |