JPH02152970A - Production of uracil - Google Patents
Production of uracilInfo
- Publication number
- JPH02152970A JPH02152970A JP63305682A JP30568288A JPH02152970A JP H02152970 A JPH02152970 A JP H02152970A JP 63305682 A JP63305682 A JP 63305682A JP 30568288 A JP30568288 A JP 30568288A JP H02152970 A JPH02152970 A JP H02152970A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- uracil
- acid
- orotic acid
- water
- 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
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 229940035893 uracil Drugs 0.000 title claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229960005010 orotic acid Drugs 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- 239000000243 solution Substances 0.000 abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 12
- 239000007864 aqueous solution Substances 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 5
- 239000013078 crystal Substances 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 229910021529 ammonia Inorganic materials 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003139 buffering effect Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012062 aqueous buffer Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000000911 decarboxylating effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BUCIWTBCUUHRHZ-UHFFFAOYSA-K potassium;disodium;dihydrogen phosphate;hydrogen phosphate Chemical compound [Na+].[Na+].[K+].OP(O)([O-])=O.OP([O-])([O-])=O BUCIWTBCUUHRHZ-UHFFFAOYSA-K 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- YXUZGLGRBBHYFZ-UHFFFAOYSA-N 2,4-dioxo-1h-pyrimidine-6-carboxylic acid;hydrate Chemical compound O.OC(=O)C1=CC(=O)NC(=O)N1 YXUZGLGRBBHYFZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- PQVHMOLNSYFXIJ-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]pyrazole-3-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(N1CC2=C(CC1)NN=N2)=O)C(=O)O PQVHMOLNSYFXIJ-UHFFFAOYSA-N 0.000 description 1
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 1
- RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- SKFFTSBCHLPDDR-UHFFFAOYSA-L [OH-].[Na+].[Cl-].[K+].OB(O)O Chemical compound [OH-].[Na+].[Cl-].[K+].OB(O)O SKFFTSBCHLPDDR-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- ZRBROGSAUIUIJE-UHFFFAOYSA-N azanium;azane;chloride Chemical compound N.[NH4+].[Cl-] ZRBROGSAUIUIJE-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KKEZAVVOJGHSFU-UHFFFAOYSA-N diazanium dihydrogen phosphate Chemical compound [NH4+].[NH4+].OP(O)([O-])=O.OP(O)([O-])=O KKEZAVVOJGHSFU-UHFFFAOYSA-N 0.000 description 1
- HDFXRQJQZBPDLF-UHFFFAOYSA-L disodium hydrogen carbonate Chemical compound [Na+].[Na+].OC([O-])=O.OC([O-])=O HDFXRQJQZBPDLF-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229960004707 orotic acid monohydrate Drugs 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- IOEGHCULCGKCNQ-UHFFFAOYSA-L potassium sodium boric acid hydrogen carbonate chloride Chemical compound [Na+].[Cl-].[K+].OB(O)O.OC([O-])=O IOEGHCULCGKCNQ-UHFFFAOYSA-L 0.000 description 1
- XKMYEGSKUFKYQL-UHFFFAOYSA-L potassium sodium dihydrogen phosphate hydrogen carbonate Chemical compound [Na+].[K+].OC(O)=O.OP([O-])([O-])=O XKMYEGSKUFKYQL-UHFFFAOYSA-L 0.000 description 1
- KVMLCRQYXDYXDX-UHFFFAOYSA-M potassium;chloride;hydrochloride Chemical compound Cl.[Cl-].[K+] KVMLCRQYXDYXDX-UHFFFAOYSA-M 0.000 description 1
- LJSOLTRJEQZSHV-UHFFFAOYSA-L potassium;sodium;hydron;hydroxide;phosphate Chemical compound [OH-].[Na+].[K+].OP(O)([O-])=O LJSOLTRJEQZSHV-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- VRYGRLBNIVQXMY-UHFFFAOYSA-M sodium;acetic acid;chloride Chemical compound [Na+].[Cl-].CC(O)=O VRYGRLBNIVQXMY-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】 イ）産業上の利用分野 ウラシルは医薬品中間体として重要な化合物である。[Detailed description of the invention] b) Industrial application field Uracil is an important compound as a pharmaceutical intermediate.
口）従来の技術
従来、ウラシルは尿素とアクリル酸との反応でヒドロウ
ラシルを得た後、臭素置換体を経由して■■■■■製造
している。Conventionally, uracil has been produced by reacting urea and acrylic acid to obtain hydrouracil and then converting it to a bromine substituted product.
この方法は多工程の反応からなり、工業的製造法には適
していない。This method involves multiple reaction steps and is not suitable for industrial production.
又、ジャーナル、オプ、オルガニック、ケミストリイ（
Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓ
ｔｒｙ）、４４巻、２１３３頁、１９７９年ではオロチ
ン酸を光照射下、脱炭酸してウラシルを製造している。Also, journal, op, organic, chemistry (
Journal of Organic Chemistry
Try), Volume 44, Page 2133, 1979, uracil is produced by decarboxylating orotic acid under light irradiation.
この方法は反応時間が長く、収率も３０％以下である。This method requires a long reaction time and a yield of less than 30%.
ケミカル、アフ゛ストラクト（Ｃｈｃｖ ｉｃａ Ｉへ
ｂｓｔｒａ、、ｔ）、５２巻、１２８５０真、１９５９
年、同５５巻、１１４２７頁、１９６１年では５−エチ
ルオロチン酸を銅粉存在下、キノリン溶媒中で脱炭酸し
て５−エチルウラシルを製造している。Chemical, Africa, Volume 52, 12850, 1959
In 1961, Vol. 55, p. 11427, 5-ethyluracil was produced by decarboxylating 5-ethyl orotic acid in a quinoline solvent in the presence of copper powder.
この方法は生成ウラシルと副生物及び金属銅粉の分離が
困難であり、収率も悪い。In this method, it is difficult to separate the produced uracil from by-products and metallic copper powder, and the yield is also poor.
更に、特開昭５８−１７２３７７号公報では５−アルキ
ルオロチン酸を硫酸中で脱炭酸して５−アルキルウラシ
ルを製造している。Further, in JP-A-58-172377, 5-alkyl orotic acid is decarboxylated in sulfuric acid to produce 5-alkyluracil.
この方法は収率は高いが、危険な濃硫酸を使用する必要
がある。Although this method provides high yields, it requires the use of hazardous concentrated sulfuric acid.
ハ）問題点を解決するための手段
本発明者等は、オロチン酸の脱炭酸反応は溶媒を使用し
ないと３００℃以上に加熱しても脱炭酸反応が進行せず
オロチン酸が分解することを見出し、水溶媒に注目し鋭
意検討した結果本発明を完成するに至った。C) Means for solving the problem The present inventors have discovered that if a solvent is not used in the decarboxylation reaction of orotic acid, the decarboxylation reaction will not proceed even if heated to 300°C or higher and the orotic acid will decompose. The present invention was completed as a result of intensive studies focusing on the water solvent.
即ち、本発明は、オロチン酸を、水溶媒中で加熱するこ
とを特徴とするウラシルの製造方法に関するものである
。That is, the present invention relates to a method for producing uracil, which comprises heating orotic acid in an aqueous solvent.
本発明の出発原料となるオロチン酸は通常の方法で容易
に得ることができる。Orotic acid, which is the starting material of the present invention, can be easily obtained by a conventional method.
例えば、ナトリウムエトキシドの存在下、チオ尿素とＴ
、γ−ジアセトキシ酢酸より２−チオウラシル−４−ア
ルデヒドを得た後、酸化することにより製造することが
できる。For example, in the presence of sodium ethoxide, thiourea and T
, 2-thiouracil-4-aldehyde is obtained from γ-diacetoxyacetic acid and then oxidized.
オロチン酸の脱炭酸反応の反応温度は、通常１５０〜２
８０℃の範囲、好ましくは２００〜２６０°Ｃの範囲が
よい。The reaction temperature for the decarboxylation reaction of orotic acid is usually 150 to 2
The temperature is preferably in the range of 80°C, preferably in the range of 200 to 260°C.
反応圧力は、常圧でも加圧でもよい。The reaction pressure may be normal pressure or increased pressure.
オロチン酸の脱炭酸で生成する炭酸ガスを反応系外へ除
去すれば、反応圧力は低下することができる。The reaction pressure can be lowered by removing carbon dioxide gas generated by decarboxylation of orotic acid to the outside of the reaction system.
反応時間は、通常１〜１５時間が適当である。The appropriate reaction time is usually 1 to 15 hours.
溶媒としての水の使用量は、通常オロチン酸１重量部に
対して１〜１００重量部が使用される。The amount of water used as a solvent is usually 1 to 100 parts by weight per 1 part by weight of orotic acid.
又、反応開始前の系はＰＨ１〜１０の範囲、好ましくは
Ｐ Ｈ２〜５の範囲に設定することが望ましい。Further, it is desirable that the pH of the system before the start of the reaction is set in the range of 1 to 10, preferably in the range of 2 to 5.
上記反応開始前の系のＰＩ（ｇＪＩ節剤としては、アン
モニア、塩酸、硫酸、燐酸及び各種緩衝水溶液が挙げら
れる。Examples of moderating agents for PI (gJI) in the system before the start of the reaction include ammonia, hydrochloric acid, sulfuric acid, phosphoric acid, and various buffer aqueous solutions.
緩衝水溶液としては、燐酸水素２アンモニウム−燐酸、
燐酸２水素カリウム−水酸化ナトリウム、燐酸２水素カ
リウム−燐酸水素２ナトリウム、燐酸２水素カリウム−
炭酸水素ナトリウム、燐酸２水素カリウム−硼砂、燐酸
２水素カリウム−燐酸水素２ナトリウム、硼酸−塩化カ
リウムー水酸化ナトリウム、硼酸−塩化カリウムー炭酸
ナトリウム、硼砂−塩酸、硼砂−水酸化ナトリウム、硼
砂−炭酸ナトリウム、硼砂−塩化ナトリウム、塩化カリ
ウム−塩酸、塩化アンモニウム−アンモニア、炭酸ナト
リウム−炭酸水素ナトリウム、酢酸ナトリウム−塩酸、
酢酸−酢酸ナトリウム、２，４゜６−トリメチルピリジ
ン−塩酸系緩衝水溶液等が使用される。As the buffer aqueous solution, diammonium hydrogen phosphate-phosphoric acid,
Potassium dihydrogen phosphate - sodium hydroxide, potassium dihydrogen phosphate - disodium hydrogen phosphate, potassium dihydrogen phosphate -
Sodium hydrogen carbonate, potassium dihydrogen phosphate-borax, potassium dihydrogen phosphate-disodium hydrogen phosphate, boric acid-potassium chloride-sodium hydroxide, boric acid-potassium chloride-sodium carbonate, borax-hydrochloric acid, borax-sodium hydroxide, borax-sodium carbonate , borax - sodium chloride, potassium chloride - hydrochloric acid, ammonium chloride - ammonia, sodium carbonate - sodium bicarbonate, sodium acetate - hydrochloric acid,
Acetic acid-sodium acetate, 2,4°6-trimethylpyridine-hydrochloric acid buffer solutions, etc. are used.
反応終了後、反応液を冷却すると生成したウラシルは結
晶として沈殿してくる。After the reaction is completed, when the reaction solution is cooled, the produced uracil precipitates as crystals.
この結晶を濾別することにより粗ウラシルを得ることが
でき、必要に応じて粗ウラシルを精製することができる
。Crude uracil can be obtained by filtering the crystals, and the crude uracil can be purified if necessary.
例えば、粗ウラシルを水、アンモニア水等のアルカリ水
溶液、塩酸又は硫酸水溶液等の酸水溶液に溶解後、活性
炭、活性白土、珪藻土等で処理し、結晶化させることに
より白色の高純度ウラシルを得ることができる。For example, after dissolving crude uracil in water, an alkaline aqueous solution such as ammonia water, or an acid aqueous solution such as hydrochloric acid or sulfuric acid aqueous solution, it is treated with activated carbon, activated clay, diatomaceous earth, etc., and crystallized to obtain white high-purity uracil. Can be done.
特に、アンモニア水の濃度は、通常５〜２８重量％のア
ンモニア水が使用される。In particular, ammonia water having a concentration of usually 5 to 28% by weight is used.
水、アルカリ水溶液、酸水溶液は、通常粗ウラシル１重
量部に対して１〜１００重量部使用される。Water, alkali aqueous solution, and acid aqueous solution are usually used in an amount of 1 to 100 parts by weight per 1 part by weight of crude uracil.
活性炭、活性白土、珪藻土は、通常粗ウラシル１重量部
に対して０．０５〜０．２重量部使用される。Activated carbon, activated clay, and diatomaceous earth are usually used in an amount of 0.05 to 0.2 parts by weight per 1 part by weight of crude uracil.
活性炭、活性白土、珪藻土等による処理温度は、通常３
０〜８０°Ｃが採用される。The treatment temperature with activated carbon, activated clay, diatomaceous earth, etc. is usually 3
0-80°C is adopted.
二）発明の効果
オロチン酸を、水溶媒中で加熱することにより高収率で
ウラシルを製造することができる。2) Effects of the invention Uracil can be produced in high yield by heating orotic acid in an aqueous solvent.
ホ）実施例
以下、本発明について実施例を挙げ更に詳細に説明する
が、本発明はこれらに限定されるものではない。E) Examples Hereinafter, the present invention will be explained in more detail by way of Examples, but the present invention is not limited thereto.
実施例１
ハステロイ−２７６製オートクレーブにオロチン酸１水
和物６．９６ｇと水３０ｍＰ、を加えた後、攪拌及び昇
温を開始した。Example 1 After adding 6.96 g of orotic acid monohydrate and 30 mP of water to a Hastelloy-276 autoclave, stirring and temperature elevation were started.
反応温度２２０ ’Ｃで７時間反応を行なった。反応圧
力は７時間後には４８ ｋｇ ／ ｃＩＡに上昇した。The reaction was carried out at a reaction temperature of 220'C for 7 hours. The reaction pressure increased to 48 kg/cIA after 7 hours.
オートクレーブを冷却したところ、反応液はスラリー状
であった。When the autoclave was cooled, the reaction solution was in the form of a slurry.
反応液を濾過し、生成ウラシルをメタノール洗浄、乾燥
して３．０７ｇのウラシルを得た。The reaction solution was filtered, and the produced uracil was washed with methanol and dried to obtain 3.07 g of uracil.
高速液体クロマトグラフィで分析を行ったところ、オロ
チン酸の転化率は８６％、ウラシルの収率は６８．５％
であった。Analysis by high performance liquid chromatography showed that the conversion rate of orotic acid was 86% and the yield of uracil was 68.5%.
Met.
実施例２
反応時間を１２時間にした他は、実施例工と同様に反応
及び後処理を行い、２．５３ｇのウラシルを得た。Example 2 The reaction and post-treatment were carried out in the same manner as in Example except that the reaction time was changed to 12 hours, and 2.53 g of uracil was obtained.
オロチン酸の転化率は９６．７％、ウラシルの収率は５
６．５％であった。The conversion rate of orotic acid was 96.7%, and the yield of uracil was 5
It was 6.5%.
実施例３
反応温度を２１０°Ｃにした他は、実施例１と同様に反
応及び後処理を行い、２．９１ｇのウラシルを得た。Example 3 The reaction and post-treatment were carried out in the same manner as in Example 1, except that the reaction temperature was changed to 210°C, and 2.91 g of uracil was obtained.
反応圧力は７時間後には３４ｋｇ／ｃ艷に上昇した。The reaction pressure rose to 34 kg/c after 7 hours.
オロチン酸の転化率は８０％、ウラシルの収率は６４％
であった。Conversion rate of orotic acid is 80%, yield of uracil is 64%
Met.
実施例４
反応温度を２３５°Ｃ１反応時間を３．５時間にした他
は、実施例１と同様に反応及び後処理を行い、１．９５
ｇのウラシルを得た。Example 4 The reaction and post-treatment were carried out in the same manner as in Example 1, except that the reaction temperature was 235°C and the reaction time was 3.5 hours.
g of uracil was obtained.
反応圧力は３．５時間後には４３ｋｇ／ｃ−に上昇した
。The reaction pressure rose to 43 kg/c- after 3.5 hours.
オロチン酸の転化率は９９．３％、ウラシルの収率は４
３．５％であった。The conversion rate of orotic acid was 99.3%, and the yield of uracil was 4
It was 3.5%.
実施例５
水の代わりに６．８重量％のアンモニア水を使用した（
反応開始前の系のＰ Ｈは１０であった。）他は、実施
例１と同様に反応及び後処理を行い、２．１ｇのウラシ
ルを得た。Example 5 6.8% by weight ammonia water was used instead of water (
The pH of the system before the start of the reaction was 10. ) Other than that, the reaction and post-treatment were carried out in the same manner as in Example 1 to obtain 2.1 g of uracil.
反応圧力は７時間後には５０ｋｇ／ｃＪに上昇した。The reaction pressure rose to 50 kg/cJ after 7 hours.
オロチン酸の転化率は９４．４％、ウラシルの収率は５
５．４％であった。The conversion rate of orotic acid was 94.4%, and the yield of uracil was 5.
It was 5.4%.
実施例６
水の代わりに１重世％硫酸水溶液を使用した（反応開始
前の系のＰＨはｌであった。）他は、実施例１と同様に
反応及び後処理を行い、３．７ｇのウラシルを得た。Example 6 The reaction and post-treatment were carried out in the same manner as in Example 1, except that a 1% sulfuric acid aqueous solution was used instead of water (the pH of the system before the start of the reaction was 1), and 3.7 g of uracil was obtained.
反応圧力は７時間後には５０ｋｇ／ｃＪに上昇した。The reaction pressure rose to 50 kg/cJ after 7 hours.
オロチン酸の転化率は９７．２％、ウラシルの収率は４
２，２％であった。The conversion rate of orotic acid was 97.2%, and the yield of uracil was 4
It was 2.2%.
実施例７
水の代わりに燐酸第２水素アンモニウム０．６６ｇ、燐
酸１．９９ｇ及び水５０ｍｆｆ１よりなる緩衝水溶液を
使用した（反応開始前の系のＰ Ｈは２．５であった。Example 7 Instead of water, an aqueous buffer solution consisting of 0.66 g of dihydrogen phosphate, 1.99 g of phosphoric acid, and 50 mff1 of water was used (the pH of the system before the start of the reaction was 2.5).
）他は、実施例１と同様に反応及び後処理を行い、３．
４５ｇのウラシルを得た。) Other than that, the reaction and post-treatment were carried out in the same manner as in Example 1, and 3.
45 g of uracil was obtained.
反応圧力は７時間後には４４ｋｇ／ｃｄに上昇した。The reaction pressure rose to 44 kg/cd after 7 hours.
オロチン酸の転化率は９０％、ウラシルの収率は７７％
であった。Conversion rate of orotic acid is 90%, yield of uracil is 77%
Met.
実施例日
水の代わりに燐酸第２水素アンモニウム０．６６ｇ、燐
酸２０ｇ及び水５０ｍ１よりなる緩衝水溶液を使用した
（反応開始前の系のＰＨは１．５であった。）他は、実
施例１と同様に反応及び後処理を行い、３．１ｇのウラ
シルを得た。Example Day: Instead of water, an aqueous buffer solution consisting of 0.66 g of dihydrogen phosphate, 20 g of phosphoric acid, and 50 ml of water was used (the pH of the system before the start of the reaction was 1.5). The reaction and post-treatment were carried out in the same manner as in 1 to obtain 3.1 g of uracil.
反応圧力は７時間後には５０ｋｇ／ｃｏ（に上昇した。The reaction pressure rose to 50 kg/co (7 hours later).
オロチン酸の転化率は９０．５％、ウラシルの収率は６
９．４％であった。Conversion rate of orotic acid is 90.5%, yield of uracil is 6
It was 9.4%.
実施例９
水の代わりに燐酸第２水素アンモニウム０．６６ｇ、燐
酸０．１ｇ及び水５０ｍｆｆ１よりなる緩衝水溶液を使
用した（反応開始前の系のＰ Ｈは３．５であった。）
他は、実施例１と同様に反応及び後処理を行い、３．３
８ｇのウラシルを得た。Example 9 Instead of water, an aqueous buffer solution consisting of 0.66 g of dihydrogen phosphate, 0.1 g of phosphoric acid, and 50 mff1 of water was used (PH of the system before the start of the reaction was 3.5).
Other than that, the reaction and post-treatment were carried out in the same manner as in Example 1, and 3.3
8 g of uracil was obtained.
反応圧力は７時間後には５０ｋｇ／ｃｏ！に上昇した。The reaction pressure was 50 kg/co after 7 hours! rose to
オロチン酸の転化率は９４．７％、ウラシルの収率は７
５．５％であった。The conversion rate of orotic acid was 94.7%, and the yield of uracil was 7.
It was 5.5%.
実施例１０
実施例１と同様に反応して得られた粗ウラシル１５ｇを
１８重量％アンモニア水２００ｇに５０°Ｃで溶解させ
た。Example 10 15 g of crude uracil obtained by the same reaction as in Example 1 was dissolved in 200 g of 18% by weight aqueous ammonia at 50°C.
この溶液に、活性炭１．５ｇを加え、５０°Ｃで３０分
間攪拌後、溶液を濾過し、ウラシルを結晶化させた。1.5 g of activated carbon was added to this solution, and after stirring at 50°C for 30 minutes, the solution was filtered to crystallize uracil.
この結晶を４宛別、水洗、乾燥して、Ｉ３．５ｇの白色
のウラシルを得た。The crystals were separated into 4 portions, washed with water, and dried to obtain 3.5 g of white uracil I.
ウラシルの純度は９９．９％以上であった。The purity of uracil was 99.9% or more.
実施例１１
実施例１と同様に反応して得られた粗ウラシル１５ｇを
水７５０ｇに８０°Ｃで溶解させた。Example 11 15 g of crude uracil obtained by the same reaction as in Example 1 was dissolved in 750 g of water at 80°C.
この溶液を塩酸水溶液によりＰ Ｈ４〜５に調整し活性
炭１．５ｇを加え、６０°Ｃで３０分間攪拌後、溶液を
濾過し、ウラシルを結晶化させた。The pH of this solution was adjusted to 4 to 5 with an aqueous hydrochloric acid solution, 1.5 g of activated carbon was added, and after stirring at 60°C for 30 minutes, the solution was filtered to crystallize uracil.
この結晶を濾別、水洗、乾燥して、１０．５ｇの白色の
ウラシルを得た。The crystals were separated by filtration, washed with water, and dried to obtain 10.5 g of white uracil.
ウラシルの純度は９９．９％以上であった。The purity of uracil was 99.9% or more.
Claims (1)
ラシルの製造方法。A method for producing uracil, which comprises heating orotic acid in an aqueous solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63305682A JPH02152970A (en) | 1988-12-02 | 1988-12-02 | Production of uracil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63305682A JPH02152970A (en) | 1988-12-02 | 1988-12-02 | Production of uracil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02152970A true JPH02152970A (en) | 1990-06-12 |
Family
ID=17948090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63305682A Pending JPH02152970A (en) | 1988-12-02 | 1988-12-02 | Production of uracil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02152970A (en) |
-
1988
- 1988-12-02 JP JP63305682A patent/JPH02152970A/en active Pending
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