JPS5849530B2 - Method for producing halogenated alcohols and halogenated esters from esters - Google Patents
Method for producing halogenated alcohols and halogenated esters from estersInfo
- Publication number
- JPS5849530B2 JPS5849530B2 JP54100575A JP10057579A JPS5849530B2 JP S5849530 B2 JPS5849530 B2 JP S5849530B2 JP 54100575 A JP54100575 A JP 54100575A JP 10057579 A JP10057579 A JP 10057579A JP S5849530 B2 JPS5849530 B2 JP S5849530B2
- Authority
- JP
- Japan
- Prior art keywords
- halogenated
- esters
- yield
- trichloro
- mol
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は炭素三重結合を有する脂肪族アルコールおよび
そのエステルの原料として重要である、ハロゲン化不飽
和アルコールおよびハロゲン化不飽和エステルの製造方
法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing halogenated unsaturated alcohols and halogenated unsaturated esters, which are important as raw materials for aliphatic alcohols having a carbon triple bond and their esters.
一般に、脂肪族モノカルボン酸のエステルは芳香を有し
、有用な香料であるが、これらのエステルにさらに不飽
和三重結合を付加することによって、これらの芳香の改
質を行うことができる。In general, esters of aliphatic monocarboxylic acids have aromas and are useful fragrances, but these aromas can be modified by further adding unsaturated triple bonds to these esters.
ハロケン化不飽和アルコールは、エステル化により容易
に・・ロゲン化不飽和エステルを得られる。A halogenated unsaturated alcohol can easily be esterified to obtain a halogenated unsaturated ester.
本発明に従うと、
一般式
（式中のＲ１、Ｒ２およびＲ３は水素原子またはアルキ
ル基である）で表わされる脂肪族モノカルボン酸エステ
ルと、
一般式
（式中のＸ１、Ｘ２、Ｘ３およびＸ４はハロゲン原子で
ある）で表わされるハロゲン化エチレンとを反応させて
、
一般式
で表わされるハロゲン化不飽和アルコールと、一般式
（各式中のＲ１、Ｒ２、Ｒ３、Ｘ１、Ｘ２およびＸ３は
前記と同じ意味をもつ）で表わされる混合物を製造する
ものである。According to the present invention, an aliphatic monocarboxylic acid ester represented by the general formula (wherein R1, R2, and R3 are hydrogen atoms or alkyl groups); A halogenated ethylene represented by a halogen atom) is reacted with a halogenated unsaturated alcohol represented by the general formula and the general formula (R1, R2, R3, X1, (having the same meaning) is produced.
本発明の方法は、脂肪族モノカルボン酸エステルとハロ
ゲン化エチレンの混合物に、有機過酸化物を添加して加
熱反応させるか、あるいは常温で光照射することによっ
て、容易にハロゲン化不飽和アルコールとハロゲン化不
飽和エステルの混合物を製造することができる。In the method of the present invention, an organic peroxide is added to a mixture of an aliphatic monocarboxylic acid ester and a halogenated ethylene, and the mixture is reacted with heat, or by irradiation with light at room temperature. Mixtures of halogenated unsaturated esters can be produced.
本発明方法において原料として用いられる脂肪族カルボ
ン酸のエステルは、カルボン酸の酸性水素原子を置換し
たアルキル基のα位置に少なくとも１個の水素原子を有
するエステルで、このアルキル基は炭素数１〜１０まで
のものであれば、直鎖状、枝分れ状のいずれでもよい。The ester of aliphatic carboxylic acid used as a raw material in the method of the present invention is an ester having at least one hydrogen atom at the α-position of an alkyl group that has replaced the acidic hydrogen atom of the carboxylic acid, and this alkyl group has 1 to 1 carbon atoms. As long as the number is up to 10, it may be either linear or branched.
またエステルを構成する脂肪族モノカルボン酸のアルキ
ル基も、置換したアルキル基と同様に、炭素数１〜１０
までが好適で、直鎖状、枝分れ状のいずれでもよい。Also, the alkyl group of the aliphatic monocarboxylic acid constituting the ester has 1 to 10 carbon atoms, similar to the substituted alkyl group.
It is preferable to have a straight chain or a branched chain.
本発明において原料として用いられるハロゲン化エチレ
ンは、たとえばテトラフルオロエチレンテトラクロロエ
チレン、テトラブロモエチレン、ジクロロジブロモエチ
レンなどであり、置換されているハロゲン原子は必ずし
も同一である必要はない。The halogenated ethylene used as a raw material in the present invention is, for example, tetrafluoroethylene, tetrachloroethylene, tetrabromoethylene, dichlorodibromoethylene, etc., and the substituted halogen atoms do not necessarily have to be the same.
本発明の第１の実施態様に従えば、脂肪族モノカルボン
酸のエステル１モル当り、ハロゲン化エチレン０．０１
〜１００モルを加え、さらに反応開始剤として有機過酸
化物を添加し、加熱反応させる。According to a first embodiment of the invention, 0.01 halogenated ethylene per mole of ester of aliphatic monocarboxylic acid
~100 mol is added, an organic peroxide is further added as a reaction initiator, and the reaction is carried out by heating.
使用される有機過酸化物の例としては、ペンゾイルペル
オキシド、２・４−ジニトロベンゾイルペルオキシド、
ジー第三ブチルペルオキシド、ラウロイルペルオキシド
、ジイソプロピルペルオキシドジカーボネート、クメン
ヒドロペルオキシドなどである。Examples of organic peroxides used include penzoyl peroxide, 2,4-dinitrobenzoyl peroxide,
These include di-tert-butyl peroxide, lauroyl peroxide, diisopropyl peroxide dicarbonate, and cumene hydroperoxide.
有機過酸化物の添加量は、脂肪族モノカルボン酸エステ
ルに対して１〜２０モル％範囲内が適当である。The amount of organic peroxide added is suitably within the range of 1 to 20 mol % based on the aliphatic monocarboxylic acid ester.
反応温度は、添加する有機過酸化物によって異なる。The reaction temperature varies depending on the organic peroxide added.
反応温度が高げればハロゲン化不飽和アルコールの生成
割合が増加し、逆に低げればハロゲン化不飽和エステル
の生成割合が増加する。If the reaction temperature is raised, the proportion of halogenated unsaturated alcohol produced increases, and conversely, if the reaction temperature is lowered, the proportion of halogenated unsaturated ester produced increases.
この場合の反応温度は、２５〜２００℃の範囲が適当で
ある。The reaction temperature in this case is suitably in the range of 25 to 200°C.
本反応はまた、本発明の第２の実施態様に従えば、不活
性ガス雰囲気中または減圧下で、光照射することにより
室温で行うことができる。This reaction can also be carried out at room temperature by light irradiation in an inert gas atmosphere or under reduced pressure, according to the second embodiment of the invention.
光照射の光源には、高圧または低圧水銀灯が用いられる
。A high pressure or low pressure mercury lamp is used as a light source for light irradiation.
照射時間は添加する有機過酸化物によって異なるが、通
常１０〜２００時間が適当である。The irradiation time varies depending on the organic peroxide added, but 10 to 200 hours is usually appropriate.
次に実施例により本発明をさらに詳細に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
酢酸メチル８８．８’ｌ７（１．２モル）とテトクロロ
エチレン４１．７５？（０．２５モル）の混合液に、ジ
ー第三ブチルペルオキシド１ ４．０ ３ Ｐ（０．０
９６モル）を添加し、空気を排除した封管中に封じ、温
度１２０℃で１７時間反応させた。Example 1 Methyl acetate 88.8'l7 (1.2 mol) and tetrachloroethylene 41.75? (0.25 mol), di-tert-butyl peroxide 1 4.0 3 P (0.0
96 mol) was added thereto, sealed in a sealed tube from which air was excluded, and reacted at a temperature of 120° C. for 17 hours.
反応後未反応原料を留去し、残油２３．４７Ｐを得た。After the reaction, unreacted raw materials were distilled off to obtain a residual oil of 23.47P.
残油を蒸留してｂｐ４７．ｏ〜１２８．０℃／７關Ｈｇ
の留分１４．９ＩＰを得た。The residual oil was distilled to bp47. o~128.0℃/7℃Hg
A fraction of 14.9 IP was obtained.
この留分を分留して、２・３・３−トリクロロ−２−フ
ロペンー１−オール７．０７′？（収率１４．５％）お
よびｂｐ７４．５〜７６．０℃／８ｍｍＨｇ （ ｎ背
１．４ ８ ７ ３ ） １−アセトキシ−２・３・３
−トリクロロー２−プロペン４．９１’（収率８．１％
）を得た。This fraction was fractionated to give 2,3,3-trichloro-2-flopen-1-ol 7.07'? (yield 14.5%) and bp74.5-76.0℃/8mmHg (n height 1.4873) 1-acetoxy-2.3.3
-Trichloro-2-propene 4.91' (yield 8.1%
) was obtained.
実施例 ２
酢酸エチル１０５．７Ｓ’（１．２モル）とテトラクロ
ロエチレン４９．７５？（０．３モル）の混合液に、ジ
ー第三ブチルペルオキシド１０．３５Ｐ（０．０７モル
）を添加し、空気を排除した封管中に封じ、１２０℃で
１７時間反応させた。Example 2 Ethyl acetate 105.7S' (1.2 mol) and tetrachlorethylene 49.75? (0.3 mol) was added with 10.35 P (0.07 mol) of di-tert-butyl peroxide, sealed in a sealed tube from which air was removed, and reacted at 120° C. for 17 hours.
反応後未反応原料を留去し、残油４０．８０？を得た。After the reaction, unreacted raw materials were distilled off, leaving a residual oil of 40.80? I got it.
残油を蒸留してｂｐ ６ ０．０ 〜９ １．０℃／
７ｍｍＨｇの留分３２．１７Ｐを得た。Distill the residual oil to bp 6 0.0 ~ 9 1.0℃/
A fraction 32.17P of 7 mmHg was obtained.
この留分を分留して、３・４・４−トリクロロ−３−プ
テンー２−オール１３．７ ７ｔ（収率２６．１％）お
よびｂｐ７１．０〜７２．０℃／８ｍｍＨｇ （ ｎ君
１． ４ ７ ８ ４ ）の２−アセトキシ３・４・４
−トリクロロー３−ブテン１４．６５Ｐ（収率２２．４
％）を得た。This fraction was fractionated to obtain 13.77 t (yield 26.1%) of 3,4,4-trichloro-3-puten-2-ol and bp 71.0-72.0°C/8 mmHg (n-kun 1 .4 7 8 4) 2-acetoxy 3, 4, 4
-Trichloro-3-butene 14.65P (yield 22.4
%) was obtained.
実施例 ３
実施例２と同様の割合の原料混合物を１１０’Ｃで１７
時間反応させた。Example 3 A raw material mixture in the same proportions as in Example 2 was heated at 110'C for 17
Allowed time to react.
反応後未反応原料を留去し、粗油３４．７７？を得た。After the reaction, unreacted raw materials were distilled off to obtain a crude oil of 34.77? I got it.
粗油を蒸留してｂｐ６０．０ 〜９０．５℃／７ｍｍＨ
ｇの留分２７．８６−Ｐを得た。Distill the crude oil to bp60.0 ~90.5℃/7mmH
g of fraction 27.86-P was obtained.
この留分を分留して、３・４・４−トリクロロー３−ブ
Ｔンー２ −，ｔ ＃ １ ２、ｏｏｙ（収率２２．
８％）および２−アセトキシ−３・４・４トリクロロー
３−ブテン１２．７９Ｐ（収率１９．６％）を得た。This fraction was fractionated to obtain 3,4,4-trichloro-3-but-2-,t #12, ooy (yield 22.
8%) and 2-acetoxy-3,4,4-trichloro-3-butene 12.79P (yield 19.6%) were obtained.
実施例 ４
酢酸プロピル１２２．！ｌ（１．２モル）とテトラクロ
ロエチレン４９．７！ｌ（０．３モル）の混合液に、ジ
−第三ブチルペルオキシド１０．３５Ｐ（０．０７モル
）を添加し、空気を排除した封管中に封じ、１２０℃で
１７時間反応させた。Example 4 Propyl acetate 122. ! l (1.2 mol) and tetrachloroethylene 49.7! 1 (0.3 mol) of di-tert-butyl peroxide was added to the mixed solution, and the mixture was sealed in a sealed tube from which air was excluded, and reacted at 120° C. for 17 hours.
反応後未反応原料を留去して、残油３７．４（ｌを得た
。After the reaction, unreacted raw materials were distilled off to obtain 37.4 (l) of residual oil.
残油を蒸留してｂｐ ６ ６．０ 〜９ ６．０℃／
８ ｍｉＨｇの留分２７．６（ｌを得た。Distill the residual oil to bp 6 6.0 ~ 9 6.0℃/
A fraction of 27.6 (l) of 8 miHg was obtained.
この留分を分留して、４・５・５−トリクロロー４−ペ
ンテン−３−オール９．８５１（収率１７．３％）およ
びｂｐ７９．０〜８３．０℃／８ｍｍＨｇ （ ｎ官１
．４ ７ ８ ５ ）の３アセトキシー４・５・５トリ
クロロー４−ペンテ７８，３６？Ｃ収率１２．Ｏ％）を
得た。This fraction was fractionated to give 4,5,5-trichloro-4-penten-3-ol 9.851 (yield 17.3%) and bp 79.0 to 83.0°C/8 mmHg (n
．． 4 7 8 5) 3 acetoxy 4.5.5 trichloro 4-pente 78,36? C yield 12. 0%) was obtained.
実施例 ５
酢酸イソプロピル１２２．Ｅｌ（１．２モル）とテトラ
クロロエチレン４９．７Ｅｌ（０．３モル）の混合液に
、ジー第三プチルペルオキシド１０．３５Ｐ（０．０７
モル）を添加し、空気を排除した封管中に封じ、１２０
℃で１７時間反応させた。Example 5 Isopropyl acetate 122. Di-tertiary butyl peroxide 10.35P (0.07
mol), sealed in a sealed tube from which air was removed, and 120
The reaction was carried out at ℃ for 17 hours.
反応後未反応原料を留去して、残油２１．８２？を得た
。After the reaction, unreacted raw materials were distilled off to leave a residual oil of 21.82? I got it.
残油を蒸留してｂｐ ４ ３．５ 〜８ ６．０℃／
８ ｍｉＨｇの留分１４．７（ｌを得た。Distill the residual oil to bp 4 3.5 ~ 8 6.0℃/
A fraction of 14.7 (l) of 8 miHg was obtained.
この留分を分留して、２−メチル−３・４・４−トリク
ロ口−３−プテンー２−オール４．２８Ｐ（収率１０．
８％）およびｂｐ ６ ６．０ 〜６ ７．０℃／ ９
ｍｍＨｇ （ ｎ賃１．５０５４）の２−アセトキシー
２−メチル−３・４・４−トリクロロ−３−ブテ７７．
９４Ｐ（収率１１，４％）を得た。This fraction was fractionated to yield 4.28 P of 2-methyl-3,4,4-trichloro-3-buten-2-ol (yield: 10.
8%) and bp 6 6.0 to 6 7.0°C/9
2-acetoxy-2-methyl-3,4,4-trichloro-3-bute in mmHg (n 1.5054) 77.
94P (yield 11.4%) was obtained.
実施例 ６
酢酸ブチル１３９．．ｌ’（１．２モル）とテトラクロ
ロエチレン４９．７５Ｐ（０．３モル）の混合液ニ、ジ
ー第三ブチルペルオキシド１０．３！１１（０．０７モ
ル）を添加し、空気を排除した封管中に封じ、１２０℃
で１７時間反応させた。Example 6 Butyl acetate 139. ．． 10.3!11 (0.07 mol) of di-tert-butyl peroxide was added to a mixed solution of l' (1.2 mol) and tetrachlorethylene 49.75P (0.3 mol), and a sealed tube was prepared from which air was excluded. Seal inside, 120℃
The reaction was carried out for 17 hours.
反応後、未反応原料を留去して残油３６．１３ｆを得た
。After the reaction, unreacted raw materials were distilled off to obtain residual oil 36.13f.
残油を蒸留してｂｐ ７ ６．０ 〜１ １ ３．５
℃／８ｍｍＨｇの留分２８．３８Ｐを得た。Distill the residual oil to bp 7 6.0 ~ 1 1 3.5
A fraction 28.38P of °C/8 mmHg was obtained.
この留分を分留し、５・６・６−トリクロロ−５−ヘキ
セン−４−オール６．８１Ｐ（収率１１．１％）および
ｂｐ９６．５〜９８．５℃７７ｍｍＨｇの（ ｎ ”Ｄ
１． ４ ８ ３ ６ ） ４−アセトキシー５・６
・６−トリクロロー５−ヘキセン１２．５９？（収率１
７．０％）を得た。This fraction was fractionated to produce 5,6,6-trichloro-5-hexen-4-ol 6.81P (yield 11.1%) and (n ”D
1. 4 8 3 6) 4-acetoxy 5, 6
・6-Trichloro-5-hexene 12.59? (yield 1
7.0%).
実施例 ７
酢酸エチル８．８１Ｐ（０．１０モル）とテトラクロ口
エチレン４．１４ｚ（０．０２５モル）の混合液に、ジ
ー第三ブチルペルオキシド０．８６Ｐ（０．００６モル
）を添加し、空気を排除したパイレツクス製の封管中に
封じ、室温（２２．０〜２２．８℃）で２４時間１００
Ｗの高圧水銀灯を照射した。Example 7 Di-tert-butyl peroxide 0.86P (0.006 mol) was added to a mixture of ethyl acetate 8.81P (0.10 mol) and tetrachlorethylene 4.14z (0.025 mol), Seal in a sealed Pyrex tube from which air is excluded, and incubate at room temperature (22.0-22.8°C) for 24 hours at 100°C.
It was irradiated with a W high pressure mercury lamp.
封管を開封し、未反応原料を回収して残油１．１６Ｐを
得た。The sealed tube was opened and unreacted raw materials were collected to obtain 1.16 P of residual oil.
これより３・４・４−トリクロロー３−ブテンー２−オ
ール０．３２Ｐ（収率（７３％）および２−アセトキシ
ー３・４・４トリクロロー３−ブテン０，５１グ（収率
１１．７％）を得た。From this, 3,4,4-trichloro-3-buten-2-ol 0.32P (yield (73%)) and 2-acetoxy 3,4,4-trichloro-3-butene 0.51g (yield 11.7%) I got it.
実施例 ８
酢酸プロビル１０．２１ｆ（０．１０モル）とテトラク
ロロエチレン４．１４Ｐ（０．０２５モル）の混合液に
、ジ−第三ブチルペルオキシド０．８６Ｐ（０．００６
モル）を添加し、空気を排除したパイレツクス製の封管
中に封じ、室温（２２．８〜２３．０℃）で２４時間１
０ ０Ｗの高圧水銀灯を照射した。Example 8 Di-tert-butyl peroxide 0.86P (0.006
mol), sealed in a sealed Pyrex tube from which air was removed, and incubated at room temperature (22.8 to 23.0°C) for 24 hours.
Irradiation was performed with a 00W high-pressure mercury lamp.
封管を開封し、未反応原料を回収して残油１．６５′？
を得た。Open the sealed tube, collect the unreacted raw materials, and leave a residual oil of 1.65'?
I got it.
この油分から、４・５・５トリクロロ−４−ペンテン−
３−オール０．３２１（収率６．８％）および３−アセ
トキシー４・５５−トリクロロー４−ペンテン０．６７
Ｐ（収率１１、５％）を得た。From this oil, 4,5,5-trichloro-4-pentene-
3-ol 0.321 (yield 6.8%) and 3-acetoxy-4,55-trichloro-4-pentene 0.67
P (yield 11, 5%) was obtained.
実施例 ９
酢酸ブｆル１１．６ １ ？ （ ０．１ ０モ／１／
） トテトラクロ口エチレン４．１ ４ｆ （ ０．０
２ ５モル）ノ混合液に、ジー第三ブチルペルオキシ
ド０．８６ｙ′（０．００６モル）を添加し、実施例８
と同様に処理して封管中に封じ、同様な条件で光照射し
た。Example 9 Bufl acetate 11.6 1? (0.1 0mo/1/
) Totetrachlorethylene 4.1 4f ( 0.0
Example 8
It was treated in the same manner as above, sealed in a sealed tube, and irradiated with light under the same conditions.
照射後未反応原料を回収して油分２．６２？を得た。After irradiation, unreacted raw materials were recovered and the oil content was 2.62? I got it.
これより５・６・６−トリクロロ−５−ヘキセン４−オ
ール０． ３ ８Ｐ （収率７．５％）および４一アセ
トキシー５・６・６−トリクロロー５−ヘキセン１．４
３ｆ（収率２３．３％）を得た。From this, 5,6,6-trichloro-5-hexen-4-ol 0. 3 8P (yield 7.5%) and 4-acetoxy 5,6,6-trichloro-5-hexene 1.4
3f (yield 23.3%) was obtained.
Claims (1)
ある）で表わされるハロゲン化エチレンを反応温度は２
５℃〜２００℃まで、圧力は常圧から２ ０ ｋｇ／ｃ
ｎｔまでの圧力の範囲内で反応させて、一般式 （各式中のＲ１、Ｒ２、Ｒ３、Ｘ１、Ｘ２およびＸ３は
前記と同じ意味をもつ）で表わされるハロゲン化不飽和
エステルとの混合物の製法。 ２ 不活性ガス、または脱気した系中で允照射して反応
を行わせる特許請求範囲第１項記載の方法。[Scope of Claims] 1 An aliphatic monocarboxylic acid ester (which is a hydrogen atom or an alkyl group of the general formula) and a fatty acid represented by the general formula (X1, X2, X3 and X4 are halogen atoms) The reaction temperature for the halogenated ethylene is 2
From 5℃ to 200℃, pressure from normal pressure to 20 kg/c
of a mixture with a halogenated unsaturated ester represented by the general formula (R1, R2, R3, X1, X2 and X3 in each formula have the same meanings as above) by reacting within a pressure range of up to Manufacturing method. 2. The method according to claim 1, in which the reaction is carried out by irradiation with an inert gas or in a degassed system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54100575A JPS5849530B2 (en) | 1979-08-07 | 1979-08-07 | Method for producing halogenated alcohols and halogenated esters from esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54100575A JPS5849530B2 (en) | 1979-08-07 | 1979-08-07 | Method for producing halogenated alcohols and halogenated esters from esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5625120A JPS5625120A (en) | 1981-03-10 |
| JPS5849530B2 true JPS5849530B2 (en) | 1983-11-05 |
Family
ID=14277686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54100575A Expired JPS5849530B2 (en) | 1979-08-07 | 1979-08-07 | Method for producing halogenated alcohols and halogenated esters from esters |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5849530B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12035645B2 (en) | 2020-02-24 | 2024-07-16 | Seedmaster Manufacturing Ltd. | Implement support apparatus with adjustable width |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6078594A (en) * | 1983-10-05 | 1985-05-04 | Yamasa Shoyu Co Ltd | Preparation of s-adenosyl-l-methionine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5321111A (en) * | 1976-08-07 | 1978-02-27 | Agency Of Ind Science & Technol | Preparation of halogenated alcohols |
-
1979
- 1979-08-07 JP JP54100575A patent/JPS5849530B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12035645B2 (en) | 2020-02-24 | 2024-07-16 | Seedmaster Manufacturing Ltd. | Implement support apparatus with adjustable width |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5625120A (en) | 1981-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2664393B2 (en) | Method for producing tert-alkyl succinate | |
| JPS5849530B2 (en) | Method for producing halogenated alcohols and halogenated esters from esters | |
| US2794826A (en) | Process of manufacturing linalyl | |
| JPS61171453A (en) | Lower alkyl ester of racemic 2,2-disubstituted cis or trans-3-formylcyclopropane-1-carboxylic acid | |
| JP2002179619A (en) | Method for producing methylcyclohexyl(meth)acrylate | |
| SE8100102L (en) | SET FOR PREPARATION OF 2- (AMYLBENZOYL) BENZOIC ACID | |
| US2514172A (en) | Esters of dihydro-and tetrahydropyran carboxylic acids, and polymers of the same | |
| US2584527A (en) | Unsaturated dicarboxylic acids and esters and their preparation | |
| US2376067A (en) | Unsaturated carboxylic acids | |
| GB1517865A (en) | Production of organic phosphorus compounds containing carboxylic groups | |
| US3649676A (en) | Process for the manufacture of unsaturated alcohol-esters | |
| US2476668A (en) | Production of derivatives of bromo aliphatic acids | |
| US3238239A (en) | Production of acrylic acid esters and amides | |
| JPS5925799B2 (en) | Method for producing hydroxyalkyl phosphine oxides and sulfides | |
| US2335652A (en) | Vinyl esters | |
| JPS5949236B2 (en) | 2-Hydroxyethylphosphine | |
| JPH0454177A (en) | Production of gamma-alkyl-gamma-lactone | |
| US3182077A (en) | Dehydration of hydroxy esters | |
| SU583740A3 (en) | Method of preparing dipropyleneglycoldi-benzoate | |
| US3261862A (en) | Esterification of sterically hindered alkanoic acids in the presence of stoichiometric amounts of a boron fluoride compound | |
| JPS62226947A (en) | Monoglyceride of highly unsaturated higher fatty acid and production thereof | |
| JPS5940817B2 (en) | Dicarboxylic acid ester and its manufacturing method | |
| JPH03240754A (en) | Production of unsaturated carboxylic acid diester | |
| JPH05502447A (en) | Oxidation method of 2-hydroxy-ethylphosphonic acid dialkyl ester | |
| US3267133A (en) | Process for preparing 2, 2-dimethylalkyl acrylates and methacrylates |