JPS643179B2 - - Google Patents
Info
- Publication number
- JPS643179B2 JPS643179B2 JP55035391A JP3539180A JPS643179B2 JP S643179 B2 JPS643179 B2 JP S643179B2 JP 55035391 A JP55035391 A JP 55035391A JP 3539180 A JP3539180 A JP 3539180A JP S643179 B2 JPS643179 B2 JP S643179B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- oxymethylene
- carbon monoxide
- aliphatic carboxylic
- 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
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003729 cation exchange resin Substances 0.000 claims description 7
- 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 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- -1 alkanoyl acetic acid Chemical compound 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 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
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、特定の酸触媒の存在下にオキシメチ
レンジアルカノエート類を一酸化炭素および水ま
たは脂肪族カルボン酸と反応させてアルカノイル
オキシ酢酸を製造する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 alkanoyloxyacetic acids by reacting oxymethylene dialkanoates with carbon monoxide and water or aliphatic carboxylic acids in the presence of a specific acid catalyst. be.
アルカノイルオキシ酢酸は、加水分解すればグ
リコール酸が得られ、水素添加すればエチレング
リコールモノエステルが得られるので重要な合成
中間体である。 Alkanoyloxyacetic acid is an important synthetic intermediate because glycolic acid can be obtained by hydrolysis and ethylene glycol monoester can be obtained by hydrogenation.
アルカノイルオキシ酢酸の製造法としては、鉱
酸触媒、固体酸触媒あるいは第８族金属−沃素系
触媒の存在下にホルムアルデヒド、一酸化炭素お
よび脂肪族カルボン酸を反応させる方法が知られ
ているが、本発明のようにオキシメチレンジアル
カノエート類を一酸化炭素および水または脂肪族
カルボン酸と反応させてアルカノイルオキシ酢酸
を製造する方法は知られていない。 As a method for producing alkanoyloxyacetic acid, a method is known in which formaldehyde, carbon monoxide, and aliphatic carboxylic acid are reacted in the presence of a mineral acid catalyst, a solid acid catalyst, or a Group 8 metal-iodine catalyst. There is no known method for producing alkanoyloxyacetic acid by reacting oxymethylene dialkanoates with carbon monoxide and water or aliphatic carboxylic acids as in the present invention.
本発明において原料として使用されるオキシメ
チレンジアルカノエート類はトリオキサンあるい
はパラホルムアルデヒドを、硫酸、過塩素酸など
の鉱酸、陽イオン交換樹脂、粘土鉱物、複合酸化
物などの固体酸の存在下に脂肪族カルボン酸ある
いはその無水物と反応させることにより製造する
ことができる。 The oxymethylene dialkanoates used as raw materials in the present invention are prepared by processing trioxane or paraformaldehyde in the presence of mineral acids such as sulfuric acid and perchloric acid, solid acids such as cation exchange resins, clay minerals, and composite oxides. It can be produced by reacting with an aliphatic carboxylic acid or its anhydride.
本発明方法においては、上記の方法で得られる
一般式
（式中、ＲおよびR′は炭素原子数１〜９のア
ルキル基を表わし、ｎは１，２または３である。）
で示されるオキシメチレンジアルカノエート類
を、酸触媒である強酸性カチオン交換樹脂の存在
下に一酸化炭素および水または脂肪族カルボン酸
と反応させることによりアルカノイルオキシ酢酸
が製造される。 In the method of the present invention, the general formula obtained by the above method is (In the formula, R and R' represent an alkyl group having 1 to 9 carbon atoms, and n is 1, 2 or 3.)
Alkanoyloxyacetic acid is produced by reacting the oxymethylene dialkanoates represented by with carbon monoxide and water or an aliphatic carboxylic acid in the presence of a strongly acidic cation exchange resin as an acid catalyst.
本発明方法においては、酸触媒として酸強度が
pKa値として2.0以下である酸点の酸性度が
0.1meq.／ｇ以上である固体酸である、強酸性カ
チオン交換樹脂が使用されている。強酸性カチオ
ン交換樹脂としては、具体的にはスルホン酸官能
基を有するスチレン−ジビニルベンゼン共重合体
またはテトラフルオロエチレン重合体が挙げら
れ。 In the method of the present invention, the acid strength of the acid catalyst is
The acidity of acid sites whose pKa value is 2.0 or less is
A strongly acidic cation exchange resin, which is a solid acid with a concentration of 0.1 meq./g or more, is used. Specific examples of the strongly acidic cation exchange resin include a styrene-divinylbenzene copolymer or a tetrafluoroethylene polymer having a sulfonic acid functional group.
酸触媒の使用量はオキシメチレンジアルカノエ
ート類１モルに対して、通常、0.1〜1000meq.で
ある。 The amount of acid catalyst used is usually 0.1 to 1000 meq. per mole of oxymethylene dialkanoate.
一酸化炭素は純粋なもののほか、窒素、ヘリウ
ム、アルゴン、水素などの反応に不活性なガスに
より希釈して用いることもできる。反応系におけ
る一酸化炭素の分圧は通常0.5〜250気圧、好まし
くは10〜150気圧に調整される。 In addition to pure carbon monoxide, carbon monoxide can also be used diluted with a gas inert to the reaction, such as nitrogen, helium, argon, or hydrogen. The partial pressure of carbon monoxide in the reaction system is usually adjusted to 0.5 to 250 atm, preferably 10 to 150 atm.
水の使用量については特に制限されるわけでは
ないが、多量に使用すると反応速度が低下するの
で、効果的に反応を行なうためにはオキシメチレ
ンジアルカノエート類に対して等モル以上、オキ
シメチレンジアルカノエート類のオキシメチレン
基１個に対して10分子以下、好ましくは５分子以
下、更に好ましくは２分子以下の水が使用され
る。 There is no particular restriction on the amount of water used, but since the reaction rate will decrease if a large amount is used, in order to carry out the reaction effectively, it is necessary to use at least an equimolar amount of oxymethylene to the oxymethylene dialkanoate. Up to 10 molecules of water, preferably up to 5 molecules, more preferably up to 2 molecules of water are used per oxymethylene group of the dialkanoates.
脂肪族カルボン酸としては炭素原子数１〜６の
ものが好ましく、通常は酢酸が使用される。脂肪
族カルボン酸はオキシメチレンジアルカノエート
類に対して等モル以上使用するのが好ましく、大
過剰に使用して反応溶媒を兼ねることもできる。 The aliphatic carboxylic acid preferably has 1 to 6 carbon atoms, and acetic acid is usually used. It is preferable to use the aliphatic carboxylic acid in an amount equal to or more than the same mole relative to the oxymethylene dialkanoate, and it can also be used in large excess to serve as a reaction solvent.
反応溶媒は特に使用する必要はないが、場合に
より反応を円滑に進行させるために適当な有機溶
媒を使用することができる。このような有機溶媒
としては、たとえば、ジエチルエーテル、ジフエ
ニルエーテル、エチレングリコールジメチルエー
テル、ジオキサン、テトラヒドロフラン等のエー
テル類、アセトン、エチルメチルケトン、ジブチ
ルケトン、アセトフエノン等のケトン類、酢酸メ
チル、酢酸エチル、酢酸ブチル、プロピオン酸メ
チル等のエステル類、ベンゼン、トルエン、ｐ−
キシレン、エチルベンゼン等の芳香族炭化水素、
ペンタン、ヘキサン、オクタン等の脂肪族飽和炭
化水素、ヘキセン−１、オクテン−２等の脂肪族
不飽和炭化水素、エチレンカーボネート、プロピ
レンカーボネート等の炭酸エステル類などが挙げ
られる。 Although it is not necessary to use a particular reaction solvent, an appropriate organic solvent may be used in order to allow the reaction to proceed smoothly in some cases. Examples of such organic solvents include ethers such as diethyl ether, diphenyl ether, ethylene glycol dimethyl ether, dioxane, and tetrahydrofuran, ketones such as acetone, ethyl methyl ketone, dibutyl ketone, and acetophenone, methyl acetate, ethyl acetate, Esters such as butyl acetate and methyl propionate, benzene, toluene, p-
Aromatic hydrocarbons such as xylene and ethylbenzene,
Examples include aliphatic saturated hydrocarbons such as pentane, hexane, and octane, aliphatic unsaturated hydrocarbons such as hexene-1 and octene-2, and carbonic acid esters such as ethylene carbonate and propylene carbonate.
反応は０〜300℃、好ましくは50〜200℃の温度
範囲で回分反応または固定床もしくは懸濁床にお
ける連続反応として行なうことができる。 The reaction can be carried out in a temperature range from 0 to 300°C, preferably from 50 to 200°C, as a batch reaction or as a continuous reaction in a fixed or suspended bed.
反応終了後、反応生成液中に触媒が懸濁してい
る場合には過、遠心分離などの方法により触媒
を分離したのち、蒸留を行なうことによりアルカ
ノイル酢酸を分離取得することができる。 After the reaction is completed, if the catalyst is suspended in the reaction product solution, the catalyst is separated by filtration, centrifugation or the like, and then the alkanoyl acetic acid can be separated and obtained by distillation.
次に本発明を実施例により更に具体的に説明す
る。 Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
300ml容の電磁誘導回転撹拌式チタン製オート
クレーブに、ジオキシメチレンジアセテート（強
酸性カチオン交換樹脂（ダイヤイオン
SK−
112）を触媒としてトリオキサンと酢酸とを反応
させたのち蒸留分散した。）4.86ｇ（30mmole）、
強酸性カチオン交換樹脂（ダイヤイオン
SK−
112）3.0ｇ（7meq.の交換容量に相当する）およ
び酢酸30mlを仕込み、一酸化炭素を60Kg／cm2まで
圧入した。オートクレーブを110℃の昇温し、撹
拌しながら３時間反応を行なつたのち、冷却し、
オートクレーブ内を放圧して反応液をガスクロマ
トグラフイーで分析した。その結果、アセトキシ
酢酸が4.37ｇ（37mmole）生成していた。Example 1 Dioxymethylene diacetate (strongly acidic cation exchange resin (Diaion SK-
112) as a catalyst, trioxane and acetic acid were reacted and then distilled and dispersed. )4.86g (30mmole),
Strongly acidic cation exchange resin (Diaion SK-
112) 3.0 g (corresponding to an exchange capacity of 7 meq.) and 30 ml of acetic acid were charged, and carbon monoxide was pressurized to 60 Kg/cm 2 . The temperature of the autoclave was raised to 110°C, the reaction was carried out for 3 hours with stirring, and then cooled.
The pressure inside the autoclave was released and the reaction solution was analyzed by gas chromatography. As a result, 4.37g (37mmole) of acetoxyacetic acid was produced.
実施例 ２
水0.54ｇ（30mmole）を添加したこと以外は実
施例１と同様に反応を行なつた。その結果、アセ
トキシ酢酸の生成量は4.2ｇ（35.6mmole）であ
つた。Example 2 The reaction was carried out in the same manner as in Example 1 except that 0.54 g (30 mmole) of water was added. As a result, the amount of acetoxyacetic acid produced was 4.2 g (35.6 mmole).
実施例 ３
酢酸のかわりにジオキサン30mlを使用したこと
以外は実施例２と同様に反応を行なつた。その結
果、アセトキシ酢酸の生成量は1.0ｇ
（8.5mmole）であつた。Example 3 The reaction was carried out in the same manner as in Example 2 except that 30 ml of dioxane was used instead of acetic acid. As a result, the amount of acetoxyacetic acid produced was 1.0g.
(8.5 mmole).
Claims (1)
ルキル基を表わし、ｎは１，２または３である。）
で示されるオキシメチレンジアルカノエート類を
一酸化炭素および水または脂肪族カルボン酸と反
応させることを特徴とするアルカノイルオキシ酢
酸の製造法。[Claims] 1. In the presence of a strongly acidic cation exchange resin, the general formula (In the formula, R and R' represent an alkyl group having 1 to 9 carbon atoms, and n is 1, 2 or 3.)
A method for producing alkanoyloxyacetic acid, which comprises reacting an oxymethylene dialkanoate represented by the formula with carbon monoxide and water or an aliphatic carboxylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3539180A JPS56131546A (en) | 1980-03-19 | 1980-03-19 | Preparation of alkanoyloxyacetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3539180A JPS56131546A (en) | 1980-03-19 | 1980-03-19 | Preparation of alkanoyloxyacetic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56131546A JPS56131546A (en) | 1981-10-15 |
| JPS643179B2 true JPS643179B2 (en) | 1989-01-19 |
Family
ID=12440607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3539180A Granted JPS56131546A (en) | 1980-03-19 | 1980-03-19 | Preparation of alkanoyloxyacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56131546A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8829248B2 (en) | 2010-08-18 | 2014-09-09 | Eastman Chemical Company | Method for recovery and recycle of ruthenium homogeneous catalysts |
| US9227896B2 (en) | 2010-08-18 | 2016-01-05 | Eastman Chemical Company | Process for the separation and purification of a mixed diol stream |
| US8466328B2 (en) | 2010-08-18 | 2013-06-18 | Eastman Chemical Company | Method for recovery and recycle of ruthenium homogeneous catalysts |
| US8709376B2 (en) | 2010-09-23 | 2014-04-29 | Eastman Chemical Company | Process for recovering and recycling an acid catalyst |
| US8785686B2 (en) | 2010-09-23 | 2014-07-22 | Eastman Chemical Company | Process for recovering and recycling an acid catalyst |
| US8765999B2 (en) | 2012-03-27 | 2014-07-01 | Eastman Chemical Company | Hydrocarboxylation of formaldehyde in the presence of a higher order carboxylic acid and a homogeneous catalyst |
| US8703999B2 (en) | 2012-03-27 | 2014-04-22 | Eastman Chemical Company | Hydrocarboxylation of methylene dipropionate in the presence of propionic acid and a heterogeneous catalyst |
| US8829234B2 (en) | 2012-03-27 | 2014-09-09 | Eastman Chemical Company | Hydrocarboxylation of formaldehyde in the presence of a higher order carboxylic acid and heterogeneous catalyst |
| US8927766B2 (en) * | 2012-03-27 | 2015-01-06 | Eastman Chemical Company | Hydrocarboxylation of methylene dipropionate in the presence of a propionic acid and a homogeneous catalyst |
| US9040748B2 (en) | 2012-06-08 | 2015-05-26 | Eastman Chemical Company | Hydrocarboxylation of aqueous formaldehyde using a dehydrating recycle stream to decrease water concentration |
-
1980
- 1980-03-19 JP JP3539180A patent/JPS56131546A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56131546A (en) | 1981-10-15 |
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