JPH0688915B2 - Hydrocarbon recovery method - Google Patents
Hydrocarbon recovery methodInfo
- Publication number
- JPH0688915B2 JPH0688915B2 JP13639485A JP13639485A JPH0688915B2 JP H0688915 B2 JPH0688915 B2 JP H0688915B2 JP 13639485 A JP13639485 A JP 13639485A JP 13639485 A JP13639485 A JP 13639485A JP H0688915 B2 JPH0688915 B2 JP H0688915B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon
- water
- alcohol
- distillation
- reaction mixture
- 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 - Lifetime
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims description 44
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 40
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 18
- 238000011084 recovery Methods 0.000 title claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 150000007524 organic acids Chemical class 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 230000000887 hydrating effect Effects 0.000 claims description 2
- 238000006703 hydration reaction Methods 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- -1 C 4 hydrocarbons Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000010685 alcohol synthesis reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
発明の目的 Purpose of the invention
本発明は、不飽和炭化水素の水和反応によるアルコール
の製造工程において、水和反応によって得られる反応混
合物から炭化水素を回収する方法に関する。The present invention relates to a method for recovering hydrocarbons from a reaction mixture obtained by a hydration reaction in an alcohol production step by a hydration reaction of an unsaturated hydrocarbon.
不飽和炭化水素の水との水和反応によってアルコールを
製造する工程においては、炭化水素、水、溶媒として使
用した有機酸類、および反応生成物であるアルコールを
含む反応混合物が得られる。この反応混合物から蒸留に
よって炭化水素を回収し、回収した炭化水素をエーテル
類や炭化水素異性体の製造に使用することが言われる。
このように、炭化水素、水、アルコールおよび有機酸か
らなる反応混合物を蒸留すると、、炭化水素はアルコー
ルおよび有機酸の一部とともに、蒸留塔の塔頂部に留出
する。しかし、回収した炭化水素を、エーテル類や炭化
水素異性体の製造に使用する場合、アルコールの含有量
が高いと、製品として得られるエーテル類や炭化水素異
性体の純度を低下させることになり、製品純度を高める
ためには、さらに蒸留設備を設ける必要が生じる。ま
た、炭化水素中に有機酸が残存していると、貯留する容
器や装置の腐食の原因となる。 蒸留において、回収される炭化水素の純度を高めるに
は、還流比を大きくして、アルコールおよび有機物の含
有率を低下させればよいが、これはいうまでもなく多大
なエネルギーを消費するので、工業的な実施には不利で
ある。 留出してくる炭化水素中の不純物が有機酸だけであれ
ば、塔頂に少量の水を供給することにより、有機酸を除
去できる。しかし、アルコールを合成した後の混合物を
蒸留すると、塔頂には、炭化水素とともに、有機酸より
も、むしろアルコールが多量に留出してくる。この場合
には、少量の水を供給しただけでは、アルコールの除去
はできない。In the step of producing alcohol by hydration reaction of unsaturated hydrocarbon with water, a reaction mixture containing hydrocarbon, water, organic acids used as a solvent, and alcohol as a reaction product is obtained. It is said that hydrocarbons are recovered from this reaction mixture by distillation and the recovered hydrocarbons are used for the production of ethers and hydrocarbon isomers.
When the reaction mixture consisting of hydrocarbon, water, alcohol and organic acid is thus distilled, the hydrocarbon distills to the top of the distillation column together with a part of the alcohol and organic acid. However, when the recovered hydrocarbon is used for the production of ethers or hydrocarbon isomers, a high alcohol content will reduce the purity of the ethers or hydrocarbon isomers obtained as a product, In order to improve the product purity, it is necessary to further install a distillation facility. Further, if the organic acid remains in the hydrocarbon, it may cause corrosion of the container or device for storing it. In the distillation, in order to increase the purity of the recovered hydrocarbon, the reflux ratio may be increased to reduce the content ratio of alcohol and organic matter, but needless to say, this consumes a large amount of energy, It is disadvantageous for industrial implementation. If the hydrocarbons distilled out contain only organic acids as impurities, the organic acids can be removed by supplying a small amount of water to the top of the column. However, when the mixture after synthesizing the alcohol is distilled, a large amount of the alcohol is distilled out at the top of the column together with the hydrocarbon, rather than the organic acid. In this case, the alcohol cannot be removed only by supplying a small amount of water.
本発明の目的は、このような問題を解決し、不飽和炭化
水素の水和反応によりアルコールを合成した後の反応混
合物から、アルコールおよび有機酸の含有率の極めて低
い炭化水素を、過大な還流を伴わない蒸留によって回収
する方法を提供することにある。An object of the present invention is to solve such a problem, and to remove excessive hydrocarbons having a very low content of alcohol and organic acid from a reaction mixture obtained by synthesizing an alcohol by hydration of unsaturated hydrocarbons. The object of the present invention is to provide a method for recovering by distillation without using.
本発明の炭化水素の回収方法は、炭素原子数４の炭化水
素と水とを、酢酸を溶媒として水和反応させて得られ
る、炭素原子数４のアルコール、炭素原子数４の炭化水
素、水、および酢酸を含む反応混合物から、蒸留によっ
て炭素原子数４の炭化水素を留出液として回収する方法
であって、前記反応混合物を蒸留塔に供給し、反応混合
物に含有されている炭素原子数４のアルコールの同モル
数の水の量と、および反応混合物中に含有されているア
ルコールが水と共沸物を形成する場合には、アルコール
の共沸に要する水の量との合計量に対する割合として1/
3以上1.0以下の量の水を供給して、反応混合物を蒸留す
る炭化水素の回収方法である。 水は、蒸留塔の濃縮部である中段以上に供給して行う
と、好ましい。The hydrocarbon recovery method of the present invention is obtained by hydrating a hydrocarbon having 4 carbon atoms and water using acetic acid as a solvent, an alcohol having 4 carbon atoms, a hydrocarbon having 4 carbon atoms, and water. A method for recovering a hydrocarbon having a carbon number of 4 as a distillate from a reaction mixture containing, and acetic acid by supplying the reaction mixture to a distillation column, the number of carbon atoms contained in the reaction mixture. The amount of water having the same number of moles of the alcohol of 4 and the amount of water required for azeotroping the alcohol when the alcohol contained in the reaction mixture forms an azeotrope with water. 1 / as a ratio
This is a hydrocarbon recovery method in which the reaction mixture is distilled by supplying water in an amount of 3 or more and 1.0 or less. Water is preferably supplied to the middle stage or higher, which is the concentration section of the distillation column.
上記の量の水を蒸留塔に供給することにより、炭化水素
とともに塔頂に留出するアルコールおよび有機酸の量を
低減することができるとともに、還流比（還流量／留出
液抜出流量）を大幅に低減させることができる。水の供
給が十分であれば還流比を低い値に、たとえば1.0以
下、さらには0.5以下にして実施することができ、回収
した炭化水素中のアルコールの濃度を2.000wt.ppm以
下、有機酸の濃度を10wt.ppm以下にすることもできる。By supplying the above-mentioned amount of water to the distillation column, the amount of alcohol and organic acid distilled at the top of the column together with the hydrocarbon can be reduced, and the reflux ratio (reflux amount / distillate withdrawal flow rate) can be reduced. Can be significantly reduced. If the supply of water is sufficient, the reflux ratio can be set to a low value, for example, 1.0 or less, and further 0.5 or less, and the concentration of alcohol in the recovered hydrocarbon can be 2.000 wt.ppm or less, the organic acid The concentration can be 10 wt.ppm or less.
蒸留塔１は、圧力２〜12kg/cm2G、好ましくは２〜5kg/c
m2G、温度150℃以下、好ましくは100℃以下の操作条件
で運転される。 本発明の方法は、不飽和炭化水素と水を、有機酸を溶媒
として水和反応によってアルコールを製造する工程にお
いて、水和反応によって得られる反応混合物中から炭化
水素を回収する方法であり、特に、炭素原子数２〜５の
炭化水素、炭素原子数１〜５のアルコール、および炭素
原子数１〜５の有機酸を含む反応混合物に適用して、炭
化水素を回収することができる。 以下、C4炭化水素を原料とし、水和反応によってtert.
−ブチルアルコール（以下「TBA」とする）を合成して
得られる反応混合物中から、C4炭化水素を回収する場合
を例にとって述べる。The distillation column 1 has a pressure of 2 to 12 kg / cm 2 G, preferably 2 to 5 kg / c.
It is operated under operating conditions of m 2 G and temperature of 150 ° C. or lower, preferably 100 ° C. or lower. The method of the present invention is a method of recovering hydrocarbons from a reaction mixture obtained by a hydration reaction in a step of producing an alcohol by a hydration reaction using an unsaturated hydrocarbon and water and an organic acid as a solvent. Can be applied to a reaction mixture containing a hydrocarbon having 2 to 5 carbon atoms, an alcohol having 1 to 5 carbon atoms, and an organic acid having 1 to 5 carbon atoms to recover the hydrocarbon. Hereinafter, the C 4 hydrocarbons as a raw material, tert by hydration reaction.
The case of recovering C 4 hydrocarbons from a reaction mixture obtained by synthesizing butyl alcohol (hereinafter referred to as “TBA”) will be described as an example.
イソブテンを主とし、ブテン−１その他を含むC4炭化水
素混合物から、水和反応によってTBAを合成して、溶媒
として使用した酢酸を含む下記の組成の反応混合物を
得、これを第１図に示す装置に供給して蒸留した。蒸留
塔１は濃縮部のトレイ段数35、回収部のトレイ段数15で
ある。２はコンデンサ、３はアキュムレータである。 ブテン−１ 15重量％ その他のC4炭化水素 20 〃 TBA 30 〃 水 10 〃 酢酸 25 〃 原料供給量は100部/Hrで、そのうちTBAは30部/Hrを占め
る。蒸留塔に供給すべき水の標準量は、つぎのとおりで
ある。 TBAと同モル数の水の量： 30×18/74＝7.3（部/Hr） TBAとの共沸に必要な水の量： 30×13/87＝4.5（部/Hr） 合計 11.8 部/Hr 留出液抜出量を30部/Hrと一定にし、蒸留塔に供給する
水の供給量と還流比を変化させて、留出液中の不純物す
なわちTBAおよび酢酸の含有量をしらべた。その結果
を、蒸留塔の操作条件とともに表１に示す。 No.1〜４は、水の供給量を標準量に近づけて行くと、還
流比を小さくしても、留出液中の不純物濃度を、TBA450
wt.ppm、酢酸は1wt.ppm未満に維持できることを示して
いる。 No.5は、水の供給量が標準量に達していても、還流をゼ
ロにすると留出液中のTBA濃度が930wt.ppmに増大し、酢
酸も1wt.ppm検出されるから、若干の還流は必要である
ことを示している。 No.6、７および９からは、水の供給量が標準の1/2以下
の場合、還流比を高くとらないと留出液中の不純物含有
量を所定の値（No.1〜４の成績）に維持できないことが
わかる。 また、No.8もNo.5と同様、水の供給量が望ましい量に達
していても、還流比が小さ過ぎては、留出液中不純物の
濃度を所望のレベル以下に保てないことを物語ってい
る。 発明の効果 本発明の回収方法により、アルコール合成反応後の混合
物から、アルコールおよび有機酸の含有量がきわめて低
い炭化水素を回収することができる。回収した不純物の
少ない炭化水素は、メチル−tert.−ブチルエーテルや
エチル−tert.−ブチルエーテルの合成、あるいはブテ
ン−１製造の原料とすて使用するのに適している。本発
明の方法は蒸留操作の還流比を低くできるから、小型の
装置でも能率よく、かつ少ないエネルギー消費で実施で
きる。TBA was synthesized from a C 4 hydrocarbon mixture containing isobutene as a main component and butene-1 and the like by a hydration reaction to obtain a reaction mixture having the following composition containing acetic acid used as a solvent. It was fed to the apparatus shown and distilled. The distillation column 1 has 35 tray stages in the concentration section and 15 tray stages in the recovery section. 2 is a capacitor and 3 is an accumulator. Butene-1 15 wt% of other C 4 hydrocarbons 20 〃 TBA 30 〃 water 10 〃 acetate 25 〃 material supply amount is 100 parts / Hr, of which TBA occupies 30 parts / Hr. The standard amount of water to be supplied to the distillation column is as follows. Amount of water with the same number of moles as TBA: 30 × 18/74 = 7.3 (parts / Hr) Amount of water required for azeotropic distillation with TBA: 30 × 13/87 = 4.5 (parts / Hr) Total 11.8 parts / The amount of Hr distillate withdrawn was kept constant at 30 parts / Hr, the amounts of water supplied to the distillation column and the reflux ratio were changed, and the contents of impurities, ie, TBA and acetic acid, in the distillate were examined. The results are shown in Table 1 together with the operating conditions of the distillation column. In Nos. 1 to 4, when the amount of water supplied was brought closer to the standard amount, the concentration of impurities in the distillate was reduced to TBA450 even if the reflux ratio was reduced.
It shows that wt.ppm and acetic acid can be maintained below 1 wt.ppm. No. 5, even if the amount of water supplied has reached the standard amount, when the reflux is set to zero, the TBA concentration in the distillate increases to 930 wt.ppm, and acetic acid is also detected at 1 wt.ppm. Reflux indicates that it is necessary. From Nos. 6, 7 and 9, when the amount of water supplied is 1/2 or less of the standard, the content of impurities in the distillate should be a predetermined value (No. 1 to 4) unless the reflux ratio is set high. You can see that you cannot maintain your grades. Similarly to No.5, even if the amount of water supplied reaches the desired amount, the concentration of impurities in the distillate cannot be kept below the desired level if the reflux ratio is too small. Tells. EFFECTS OF THE INVENTION According to the recovery method of the present invention, hydrocarbons having extremely low alcohol and organic acid contents can be recovered from the mixture after the alcohol synthesis reaction. The recovered hydrocarbon with a small amount of impurities is suitable for use as a raw material for the synthesis of methyl tert.-butyl ether or ethyl tert.-butyl ether, or for the production of butene-1. Since the reflux ratio of the distillation operation can be lowered in the method of the present invention, it can be carried out efficiently even with a small apparatus and with low energy consumption.
第１図は、本発明の炭化水素の回収方法を説明するフロ
ーチャートである。 １……蒸留塔 ２……コンデンサ ３……アキュムレータFIG. 1 is a flow chart for explaining the hydrocarbon recovery method of the present invention. 1 ... Distillation tower 2 ... Condenser 3 ... Accumulator
Claims (5)
溶媒として水和反応させて得られる、炭素原子数４のア
ルコール、炭素原子数４の炭化水素、水、および酢酸を
含む反応混合物から、蒸留によって炭素原子数４の炭化
水素を留出液として回収する方法であって、前記反応混
合物を蒸留塔に供給し、反応混合物に含有されている炭
素原子数４のアルコールの同モル数の水の量と、および
反応混合物中に含有されているアルコールが水と共沸物
を形成する場合には、アルコールの共沸に要する水の量
との合計量に対する割合として1/3以上1.0以下の量の水
を供給して、反応混合物を蒸留する炭化水素の回収方
法。1. A hydrocarbon having 4 carbon atoms, a hydrocarbon having 4 carbon atoms, water, and acetic acid obtained by hydrating a hydrocarbon having 4 carbon atoms and water with acetic acid as a solvent. A method of recovering a hydrocarbon having a carbon number of 4 as a distillate from a reaction mixture by distillation, which comprises supplying the reaction mixture to a distillation column to obtain the same amount of alcohol having a carbon number of 4 contained in the reaction mixture. When the amount of water in moles and the alcohol contained in the reaction mixture form an azeotrope with water, 1/3 as a ratio to the total amount of water required for azeotropic distillation of alcohol. A method for recovering hydrocarbons by distilling the reaction mixture by supplying water in an amount of 1.0 or more.
下で蒸留を行う特許請求の範囲第１項に記載の炭化水素
の回収方法。2. The method for recovering hydrocarbon according to claim 1, wherein the distillation is carried out at a distillation column pressure of 2 to 10 kg / cm 2 G and a temperature of 150 ° C. or less.
蒸留を行う特許請求の範囲第１項に記載の炭化水素の回
収方法。3. The method for recovering hydrocarbon according to claim 1, wherein the distillation is carried out by supplying water to the middle or higher stage of the concentration section of the distillation column.
量）1.0以下で蒸留を実施する特許請求の範囲第１項に
記載の炭化水素の回収方法。4. The method for recovering hydrocarbon according to claim 1, wherein the distillation is carried out at a hydrocarbon recovery ratio (reflux amount / distillate withdrawal flow rate) of 1.0 or less.
が2,000wt.ppm以下、かつ有機酸の濃度が10wt.ppm以下
である特許請求の範囲第１項ないし第４項のいずれかに
記載の炭化水素の回収方法。5. The method according to any one of claims 1 to 4, wherein the recovered hydrocarbon has an alcohol concentration of 2,000 wt.ppm or less and an organic acid concentration of 10 wt.ppm or less. Hydrocarbon recovery method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13639485A JPH0688915B2 (en) | 1985-06-22 | 1985-06-22 | Hydrocarbon recovery method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13639485A JPH0688915B2 (en) | 1985-06-22 | 1985-06-22 | Hydrocarbon recovery method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61293934A JPS61293934A (en) | 1986-12-24 |
| JPH0688915B2 true JPH0688915B2 (en) | 1994-11-09 |
Family
ID=15174131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13639485A Expired - Lifetime JPH0688915B2 (en) | 1985-06-22 | 1985-06-22 | Hydrocarbon recovery method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0688915B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2470001C1 (en) * | 2011-10-05 | 2012-12-20 | Открытое акционерное общество "Научно-исследовательский и проектный институт по переработке газа" (ОАО "НИПИгазпереработка") | Apparatus for drying and cleaning hydrocarbon fraction from methanol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1095819C (en) * | 1999-09-29 | 2002-12-11 | 中国石油化工集团公司 | Process for continuously preparing low-carbon alcohol |
| RU2470002C1 (en) * | 2011-10-05 | 2012-12-20 | Открытое акционерное общество "Научно-исследовательский и проектный институт по переработке газа" (ОАО "НИПИгазпереработка") | Method of cleaning and drying propane fraction from methanol |
-
1985
- 1985-06-22 JP JP13639485A patent/JPH0688915B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2470001C1 (en) * | 2011-10-05 | 2012-12-20 | Открытое акционерное общество "Научно-исследовательский и проектный институт по переработке газа" (ОАО "НИПИгазпереработка") | Apparatus for drying and cleaning hydrocarbon fraction from methanol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61293934A (en) | 1986-12-24 |
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