JPS6363536B2 - - Google Patents
Info
- Publication number
- JPS6363536B2 JPS6363536B2 JP13744284A JP13744284A JPS6363536B2 JP S6363536 B2 JPS6363536 B2 JP S6363536B2 JP 13744284 A JP13744284 A JP 13744284A JP 13744284 A JP13744284 A JP 13744284A JP S6363536 B2 JPS6363536 B2 JP S6363536B2
- Authority
- JP
- Japan
- Prior art keywords
- sorbic acid
- petroleum
- solution
- reaction
- crude
- 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
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 20
- 229940075582 sorbic acid Drugs 0.000 claims description 20
- 235000010199 sorbic acid Nutrition 0.000 claims description 20
- 239000004334 sorbic acid Substances 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 4
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 3
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 3
- 238000007664 blowing Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、ソルビン酸を蒸留精製するに当り粗
ソルビン酸を石油中に溶解し、減圧下で瞬間蒸発
させる方法の改良に関する。
クロトンアルデヒドとケテンの反応によつて得
られたポリエステルを分解してソルビン酸を合成
するには塩酸分解法、アルカリ分解法、熱分解法
等があるが、この中、塩酸分解法は異性体の生成
を伴うことなく、分解成績上も収率的に、かつ品
質的に最も有利であることが知られている。しか
し、いずれの場合に於ても反応中に副生したター
ル分がポリエステル残渣と共に不純物として存在
するため、特別の精製工程を必要とする問題があ
る。又、比較的優位な塩酸分解法に於ても、この
課題が残り、ポリエステルを分解した後、冷却
過して得られる粗ソルビン酸はタール分を含有し
ている。このとき、脱塩酸を行なう必要もある。
該ソルビン酸の精製法の一つとして蒸留精製法
があるが、ソルビン酸は構造上、熱に不安定であ
り、溶融状態では直ちに重合し始め、さらにそれ
が不純であるほどはなはだしい。そのため、ソル
ビン酸単独で蒸留精製することは工業的には不可
能に近い。しかるに、これを改善し、かつ他法に
優れた共蒸留去が提案されているが（ドイツ特許
第1044803号、特公昭44−4091等）、ソルビル酸の
樹脂化などの点から必ずしも満足すべきものでは
ない。そこに塩酸分解工程を経た粗ソルビン酸中
に含有されている塩酸が蒸留精製工程に於てソル
ビン酸と共に留去し、精製ソルビン酸結晶中に含
有されることである。
而して、本発明者らは共蒸留去に関し、従来法
の欠点を考慮した上で鋭意検討を重ねた結果、こ
れと比べて簡単な処理手段を採用することにより
設備面でも収率面でも経済的に有利で、かつ品質
の良好な（特に、塩酸含有量が低い）ソルビン酸
を得ることに成功した。即ち、本発明はクロトン
アルデヒドとケテンとの反応で得られたポリエス
テルを塩酸分解し、反応液から分離した粗ソルビ
ン酸を精製せしめるソルビン酸の精造法において
(a) 粗ソルビン酸を温度範囲100〜140℃で石油に
連続溶解すると共に該石油溶解液中の残存水を
蒸発せしめ
(b) 次いで該石油溶液を分離塔を付備した薄膜蒸
発機を利用して減圧下（圧力範囲20〜60mmHg）
連続瞬間蒸発させ、一方、蒸発機の底部からタ
ール分を含む蒸発残渣を取去せしめ
(c) さらに蒸発したソルビン酸と石油とのガス流
に対して分離塔の頂部から石油を供給すると共
に系内へ不活性ガスを吹込ましめることを特徴
とするソルビン酸の製造法。
である。
ところで、本発明における技術的思想の根幹は
塩素分の生い立ちとその挙動を解明した点にあ
る。即ち、本発明者らが該製造工程全般に亘り、
これら課題について検討を進める中、理論上充分
ではないが、○
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an improvement in a method for distilling and purifying sorbic acid by dissolving crude sorbic acid in petroleum and flash-evaporating it under reduced pressure. There are hydrochloric acid decomposition methods, alkaline decomposition methods, thermal decomposition methods, etc. to synthesize sorbic acid by decomposing polyester obtained by the reaction of crotonaldehyde and ketene. It is known that it is the most advantageous in terms of yield and quality in terms of decomposition results without any production. However, in any case, there is a problem in that a special purification step is required because tar by-produced during the reaction exists as an impurity together with the polyester residue. Furthermore, even with the comparatively superior hydrochloric acid decomposition method, this problem remains, and the crude sorbic acid obtained by cooling and cooling the polyester after decomposing it contains tar. At this time, it is also necessary to perform dehydrochlorination. One of the methods for purifying sorbic acid is a distillation purification method, but sorbic acid is unstable to heat due to its structure and immediately begins to polymerize in a molten state, and the more impure the more rapid it becomes. Therefore, it is almost impossible industrially to purify sorbic acid alone by distillation. However, although co-distillation has been proposed that improves this and is superior to other methods (German Patent No. 1044803, Japanese Patent Publication No. 44-4091, etc.), it is not necessarily satisfactory from the viewpoint of converting sorbic acid into a resin. isn't it. The hydrochloric acid contained in the crude sorbic acid that has undergone the hydrochloric acid decomposition step is distilled off together with the sorbic acid in the distillation purification step, and is contained in the purified sorbic acid crystals. The inventors of the present invention have conducted extensive studies regarding co-distillation, taking into account the shortcomings of conventional methods, and have found that by adopting a simpler treatment method compared to the conventional method, improvements can be made in terms of equipment and yield. We succeeded in obtaining economically advantageous sorbic acid of good quality (particularly low hydrochloric acid content). That is, the present invention provides a method for purifying sorbic acid in which a polyester obtained by the reaction of crotonaldehyde and ketene is decomposed with hydrochloric acid and crude sorbic acid separated from the reaction solution is purified. Continuously dissolve in petroleum at ~140°C and evaporate residual water in the petroleum solution (b) Then, the petroleum solution is dissolved under reduced pressure (pressure range 20 to 60 mmHg) using a thin film evaporator equipped with a separation column. )
Continuous flash evaporation is performed, while the evaporation residue containing tar is removed from the bottom of the evaporator. A method for producing sorbic acid characterized by blowing an inert gas into the sorbic acid. It is. Incidentally, the basis of the technical idea of the present invention lies in the elucidation of the origin of chlorine content and its behavior. That is, the present inventors throughout the manufacturing process,
While considering these issues, although it is not theoretically sufficient,...
Claims (1)
れたポリエステルを塩酸分解し、反応液から分離
した粗ソルビン酸を精製せしめるソルビン酸の製
造法において (a) 粗ソルビン酸を温度範囲100〜140℃で石油に
連続溶解すると共に、該石油溶解液中の残存水
を蒸発せしめ (b) 次いで該石油溶液を分離塔を付備した薄膜蒸
発機を利用して減圧下（圧力範囲20〜60mmHg）
連続瞬間蒸発させ、一方、蒸発機の底部からタ
ール分を含む蒸発残渣を取去せしめ (c) さらに蒸発したソルビン酸と石油とのガス流
に対して分離塔の頂部から石油を供給すると共
に、系内へ不活性ガスを吹込ましめることを特
徴とするソルビン酸の製造法。[Claims] 1. A method for producing sorbic acid in which a polyester obtained by the reaction of crotonaldehyde and ketene is decomposed with hydrochloric acid and crude sorbic acid separated from the reaction solution is purified: (a) Crude sorbic acid is heated within a temperature range. Continuously dissolve in petroleum at 100 to 140°C and evaporate residual water in the petroleum solution (b) Then, the petroleum solution is heated under reduced pressure (pressure range 20°C) using a thin film evaporator equipped with a separation column. ~60mmHg)
continuous flash evaporation, while removing the evaporation residue containing tar from the bottom of the evaporator; A method for producing sorbic acid characterized by blowing an inert gas into the system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13744284A JPS6117535A (en) | 1984-07-03 | 1984-07-03 | Preparation of sorbic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13744284A JPS6117535A (en) | 1984-07-03 | 1984-07-03 | Preparation of sorbic acid |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23531885A Division JPH0629215B2 (en) | 1985-10-23 | 1985-10-23 | Method for producing sorbic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6117535A JPS6117535A (en) | 1986-01-25 |
| JPS6363536B2 true JPS6363536B2 (en) | 1988-12-07 |
Family
ID=15198716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13744284A Granted JPS6117535A (en) | 1984-07-03 | 1984-07-03 | Preparation of sorbic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6117535A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262134A (en) * | 2014-08-27 | 2015-01-07 | 江苏天成生化制品有限公司 | Sorbic acid continuous desolventizing method |
-
1984
- 1984-07-03 JP JP13744284A patent/JPS6117535A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6117535A (en) | 1986-01-25 |
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