WO2016047957A1 - 고효율의 네오펜틸 글리콜의 제조방법 및 이의 제조장치 - Google Patents
고효율의 네오펜틸 글리콜의 제조방법 및 이의 제조장치 Download PDFInfo
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- WO2016047957A1 WO2016047957A1 PCT/KR2015/009661 KR2015009661W WO2016047957A1 WO 2016047957 A1 WO2016047957 A1 WO 2016047957A1 KR 2015009661 W KR2015009661 W KR 2015009661W WO 2016047957 A1 WO2016047957 A1 WO 2016047957A1
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- neopentyl glycol
- hydrogenation reactor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
Definitions
- the present disclosure relates to a method for manufacturing high efficiency neopentyl glycol and a manufacturing apparatus thereof, and more specifically, unlike the prior art, energy need not be separately heated from a feed vessel to a hydrogenation reactor inlet.
- the present invention relates to a method for manufacturing neopentyl glycol and a method for manufacturing the same, wherein the high boiling by-products are not generated in the above section, thereby preventing poisoning of the hydrogenation catalyst in the reactor by the high boiling by-products, and further improving the yield of the hydrogenation reaction.
- Neopentyl glycol is a white crystalline material with a melting point of 130 ° C or higher. It is used as an important intermediate for various synthetic resins. It is also used as a raw material for various plastic powder coatings, synthetic lubricants, plasticizers, surfactants, and textile processing agents. It is widely used.
- Such NPG is generally prepared by aldol condensation reaction of isobutyraldehyde with formaldehyde to form hydroxypivaldehyde (HPA), and then reacting the HPA with hydrogen under a catalyst.
- HPA hydroxypivaldehyde
- the reaction must be heated to a high temperature in order to maintain the liquid state of the HPA feedstock from the feed vessel to the inlet of the hydrogenation reactor, so that the HPNE feedstock, already a high-boiling by-product, before being introduced into the hydrogenation reactor
- By-products such as, etc. are generated to reduce the HPA content from the hydrogenation reactor inlet, eventually reducing the content of NPG generated after the hydrogenation reaction, and the content of by-products such as neopentylglycol hydroxy pivalate (HPNE) is rather increased.
- the by-products are known to be temperature sensitive so far that the higher the temperature, the greater the rate and amount of the produced product. However, if the temperature is lowered, the complete liquefaction of the HPA raw material is impossible, so that the reactivity decreases. On the contrary, if the temperature of the HPA raw material is increased to increase the reactivity, a by-product increases significantly.
- an object of the present disclosure is to provide a method for producing high efficiency neopentyl glycol having low by-products without decreasing reactivity and a manufacturing apparatus thereof.
- the present invention is a method for preparing neopentyl glycol by adding a hydroxy fibaldehyde solution and hydrogen to a hydrogenation reactor including a hydrogenation catalyst, the hydroxy fibaldehyde solution is a hydroxy It provides a method for preparing neopentyl glycol, which comprises 6 to 30% by weight of cifialdehyde, 35 to 70% by weight of neopentyl glycol, 10 to 30% by weight of alcohol and 10 to 30% by weight of water.
- the present invention includes a feed vessel in which the hydroxyfibaldehyde solution is stored; A raw material supply pipe for supplying a hydroxyfibaldehyde solution to the hydrogenation reactor in the feed basin; A hydrogen supply pipe for supplying hydrogen to the hydrogenation reactor; A hydrogenation reactor having a hydrogenation catalyst fixed therein; Discharge piping for discharging the neopentyl glycol product generated from the hydrogenation reactor; A neopentyl glycol recovery pipe for supplying some neopentyl glycol product from the discharge pipe to the feed basin; A recycle pipe for recycling some neopentyl glycol product from the discharge pipe to the hydrogenation reactor; It provides a neopentyl glycol manufacturing apparatus comprising a; and a heating device for heating the hydroxy fibaldehyde solution supplied to the hydrogenation reactor through the raw material supply pipe just before being introduced into the hydrogenation reactor.
- 1 is a process diagram schematically showing a manufacturing process of neopentyl glycol of the present disclosure.
- the method for preparing neopentyl glycol according to the present invention is a method for preparing neopentyl glycol by adding a hydroxyfibaldehyde solution and hydrogen to a hydrogenation reactor including a hydrogenation catalyst, wherein the hydroxyfibaldehyde solution is hydroxypi 6 to 30% by weight of brothide, 35 to 70% by weight of neopentyl glycol, 10 to 30% by weight of alcohol and 10 to 30% by weight of water.
- the feed basin is not particularly limited in the case of a means capable of supplying the raw material to the raw material supply pipe by storing the raw material, and may be, for example, a raw material storage tank, a raw material supply tank, or a feeding tank.
- the feed basin may further include agitation means capable of mixing the raw materials, for example.
- the hydroxyfibaldehyde solution may include, for example, 8 to 20% by weight of hydroxyfibaldehyde, 40 to 52% by weight of neopentyl glycol, 15 to 25% by weight of alcohol and 10 to 27% by weight of water. In this case, the by-products are less effective without lowering the reactivity.
- the weight ratio of hydroxyfibaldehyde and neopentyl glycol is, for example, 1: 1.5 to 1: 8, or 1: 2 to 1: 6.5, and the heat is well within this range, so that the reaction is good and there are few by-products. There is.
- the alcohol may be, for example, octanol, i-butanol or methanol, and preferably octanol.
- the water may be 10 to 30% by weight, for example 10 to 27% by weight or 12 to 30% by weight, the reactivity, HPA conversion and NPG yield within this range is excellent effect.
- the neopentyl glycol may be, for example, a part of the neopentyl glycol discharged from the hydrogenation reactor, and in this case, since the same material as the reaction product is used, a separate separation step is not required in the post-treatment process, so it is economical and has good process efficiency. It works.
- the hydroxyfibaldehyde solution is maintained at 40 to 100 ° C., or 60 to 75 ° C., from a feed vessel, for example, and is supplied to a hydrogenation reactor.
- the temperature is low, the raw material solution is solidified to cause problems in transport.
- by-products are generated and the temperature is maintained at a high temperature, by-products are made in the feed basin, thereby maintaining an appropriate temperature in the above range has the effect of increasing the reaction yield while suppressing the by-product generation.
- the maintenance of the temperature of the feed basin can be achieved smoothly by incorporating the hot NPG product discharged from the hydrogenation reactor into the feed basin (mixed with hydroxyfibaldehyde) at a constant rate.
- the hydroxyfibaldehyde solution may be dispersed and added by a distributor when it is introduced into the hydrogenation reactor, for example, and the reaction yield, HPA conversion and NPG selectivity are excellent in this case.
- the temperature inside the hydrogenation reactor that is, the reaction temperature or the reactor inlet temperature is, for example, 100 to 250 ° C, 130 to 200 ° C, or 140 to 195 ° C.
- the pressure inside the hydrogenation reactor ie the reaction pressure, is, for example, 10 to 250 bar, 20 to 120 bar, or 25 to 50 bar.
- the hydrogenation catalyst may be, for example, a copper-based catalyst.
- the copper-based catalyst is, for example, a CuO / BaO catalyst.
- the catalyst has an excellent performance and a long lifespan.
- the CuO / BaO catalyst is preferably a CuO / BaO catalyst containing 60 to 99 wt% of CuO and 1 to 40 wt% of BaO, more preferably 80 to 95 wt% of CuO and BaO CuO / BaO catalyst containing 5 to 20% by weight, most preferably CuO / BaO catalyst containing 85 to 90% by weight of CuO and 10 to 15% by weight of BaO, within the range of Excellent performance and long life.
- the CuO / BaO catalyst may measure metal and metal oxide contents through ICP analysis.
- the copper-based catalyst may include, for example, a silicon oxide or aluminum oxide support.
- the performance and physical properties of the catalyst may be good, and the activity of the catalyst may be maintained for a long time.
- the copper catalyst may be preferably a CuO / BaO / SiO catalyst.
- the sum of x and y is preferably 20 to 50 (% by weight), or 30 to 50 (% by weight) based on the sum of x, y and z (100% by weight), and the performance of the catalyst within this range. This is an excellent and long life effect.
- the hydrogenation reactor is, for example, a fixed bed reactor, and in this case, the catalyst and the reaction product are easily separated, the catalyst replacement is easy, and the reactor size can be reduced, thereby making an economic process.
- the hydroxyfibaldehyde solution is preferably prepared in a feed vessel (feed vessel) is supplied to the hydrogenation reactor, for example, in this case the entire manufacturing process can be operated stably, there is an effect that the operation is easy.
- the hydroxyfibaldehyde solution is prepared in the feed basin does not mean that the hydroxyfibaldehyde solution of the desired composition is made during the feed of the raw material in the raw material supply pipe, but the hydroxyfibaldehyde of the desired composition in the feed basin. After making the solution, it is supplied to the hydrogenation reactor through the raw material supply pipe.
- the neopentyl glycol solution discharged from the hydrogenation reactor may include, for example, 6 wt% or less, or 5.5 wt% or less of a high boiling point component having a higher boiling point than NPG.
- the purification equipment is simple and the purification cost is low. It works.
- the high boiling point component may be, for example, hydroxyfibaldehyde dimer, that is, HPNE.
- the hydroxyfibaldehyde solution may be mixed with hydrogen gas, for example, before being supplied to the hydrogenation reactor, and in this case, the dispersion efficiency of the gas and liquid raw materials introduced into the reactor may be increased, thereby increasing the HPA conversion rate and NPG yield. There is.
- the method for producing neopentyl glycol is, for example, a portion of the neopentyl glycol solution discharged from the hydrogenation reactor may be recycled to the hydrogenation reactor, in this case, in combination with the heat exchanger has the effect of easily controlling the heat generated in the hydrogenation reaction have.
- the hydroxyfibaldehyde solution may be heated to near the hydrogenation reaction temperature by heating means or a heating device, for example, just before being introduced into the hydrogenation reactor, in which case the HPA conversion rate and the hydrogenation reaction yield are excellent.
- the heating means or heating device is usually not particularly limited as long as it is a heating means or heating device that can be applied to a hydrogenation reaction device of a hydroxyfibaldehyde solution.
- Just before being introduced into the hydrogenation reactor may mean between the hydrogenation reactor from the point where the hydroxyfibaldehyde solution and the recycled neopentyl glycol solution meet, or between the hydrogenation reactor at the connection site of the raw material supply pipe and the recycling pipe. .
- Near the hydrogenation reaction temperature may be, for example, 50 to 200 °C, 60 to 180 °C, or 80 to 145 °C.
- the method for producing neopentyl glycol may be, for example, not separately heated from a feed vessel to a hydrogenation reactor inlet, in which case the production of by-products in the process of feeding the reactor is suppressed while preventing the solidification of the reaction raw materials. It is effective.
- the neopentyl glycol manufacturing apparatus of the present disclosure includes a feed vessel in which a hydroxyfibaldehyde solution is stored; A raw material supply pipe for supplying a hydroxyfibaldehyde solution to the hydrogenation reactor in the feed basin; A hydrogen supply pipe for supplying hydrogen to the hydrogenation reactor; A hydrogenation reactor having a hydrogenation catalyst fixed therein; Discharge piping for discharging the neopentyl glycol product generated from the hydrogenation reactor; A neopentyl glycol recovery pipe for supplying some neopentyl glycol product from the discharge pipe to the feed basin; A recycle pipe for recycling some neopentyl glycol product from the discharge pipe to the hydrogenation reactor; And a heating device for heating the hydroxyfibaldehyde solution supplied to the hydrogenation reactor through the raw material supply pipe just before being introduced into the hydrogenation reactor.
- a distributor may be installed at a point connected to the upper hydrogen supply pipe, and in this case, reaction yield, HPA conversion rate, and NPG selectivity may be improved.
- the feed basin may be connected to the HPA manufacturing apparatus as an example.
- FIG. 1 is a process diagram schematically showing an example of the NPG manufacturing process of the present invention, when using the hydroxyfibaldehyde solution (HPA solution) according to the present invention does not require a separate heating (heating) to save energy
- HPA solution hydroxyfibaldehyde solution
- By-products are not produced in the sections 1 to 2, and thus, poisoning of the hydrogenation catalyst by the by-products, in particular, high-boiling by-products such as HPNE, is prevented, and eventually, the NPG content of the product at the reactor outlet 3 is greatly increased. have.
- the neopentyl glycol product produced from the hydrogenation reactor was obtained from an outlet tube connected to the bottom of the hydrogenation reactor, and the composition of the neopentyl glycol product thus obtained was measured by gas chromatography (HP-1, Agilent, Conditions: 70 ° C./3 min-10 ° C./min-280° C./35 min ° C.).
- HPA Hydroxyfibaldehyde solution
- HPA Hydroxyfibaldehyde solution
- HPA Hydroxyfibaldehyde solution
- High boiling point component components with higher boiling point than NPG, containing 3 to 3.5% by weight of HPNE, and remaining components correspond to unknown substances having higher boiling point than NPG
- the preparation method of neopentyl glycol of the present invention is excellent in the HPA conversion and NPG reaction yield, in particular the neopentyl glycol product obtained through this by-product (new addition It was confirmed that there was almost no high boiling point component).
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Abstract
Description
구분 | 실시예1 | 실시예2 | 실시예3 | 비교예1 | 비교예2 | |
HPA용액조성 | NPG | 48 | 40 | 52 | 55 | 34.5 |
HPA | 12 | 20 | 8 | 5 | 25.5 | |
2-EH+H2O | 35.1 | 34.8 | 34.9 | 35.2 | 35 | |
고비점성분 | 4.9 | 5.2 | 5.1 | 4.8 | 5 | |
NPG용액조성 | NPG | 59.8 | 59.5 | 59.7 | 57 | 56 |
HPA | 0.1 | 0.04 | 0.08 | 0.3 | 1 | |
2-EH+H2O | 35 | 35 | 35 | 35 | 35 | |
고비점성분 | 5.1 | 5.46 | 5.22 | 7.7 | 8 | |
HPA 전환율(%) | 99.2 | 99.8 | 99.0 | 94.0 | 96.1 | |
NPG 수율(%) | 99.7 | 99.2 | 99.5 | 95.0 | 93.3 |
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Claims (17)
- 수소화 촉매를 포함하는 수소화 반응기에 히드록시피브알데히드 용액과 수소를 투입하여 네오펜틸 글리콜을 제조하는 방법에 있어서, 상기 히드록시피브알데히드 용액은 히드록시피브알데히드 6 내지 30 중량%, 네오펜틸 글리콜 35 내지 70 중량%, 알코올 10 내지 30 중량% 및 물 10 내지 30 중량%를 포함하는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 히드록시피브알데히드 용액는 피드 배슬(feed vessel)에서 준비되어 수소화 반응기로 공급되는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 히드록시피브알데히드와 네오펜틸 글리콜의 중량비는 1:1.5 내지 1:8인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 3항에 있어서,상기 히드록시피브알데히드와 네오펜틸 글리콜의 중량비는 1:2 내지 1:6.5인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 네오펜틸 글리콜은 상기 수소화 반응기에서 배출된 네오펜틸 글리콜의 일부인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 히드록시피발알데이드 용액은 40 내지 100 ℃로 유지되어 수소화 반응기에 공급되는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 수소화 반응기 내부의 온도는 100 내지 250 ℃인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 수소화 촉매는 구리계 촉매인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 8항에 있어서,상기 구리계 촉매는 CuO/BaO 촉매인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제8항에 있어서,상기 구리계 촉매는 지지체로 규소산화물 또는 알루미늄산화물을 포함하는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 수소화 반응기는 고정층 반응기(fixed bed reactor)인 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 수소화 반응기에서 배출되는 네오펜틸 글리콜 용액은 네오펜틸글리콜 하이드록시피발레이트(HPNE)가 6.0 중량% 이하로 포함되는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 히드록시피브알데히드 용액은 수소화 반응기에 공급되기 전에 수소 가스와 혼합되는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 네오펜틸 글리콜의 제조방법은 상기 수소화 반응기에서 배출되는 네오펜틸 글리콜 용액의 일부가 수소화 반응기로 재순환되는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 히드록시피브알데히드 용액은 수소화 반응기에 투입되기 직전에 수소화 반응 온도까지 가열되는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 제 1항에 있어서,상기 네오펜틸 글리콜의 제조방법은 피드 배슬(feed vessel)에서 수소화 반응기 입구까지 별도로 가열하지 않는 것을 특징으로 하는네오펜틸 글리콜의 제조방법.
- 히드록시피브알데히드 용액이 저장된 피드 배슬(feed vessel); 상기 피드 배슬에서 히드록시피브알데히드 용액을 수소화 반응기로 공급하는 원료공급배관; 수소를 상기 수소화 반응기에 공급하는 수소공급배관; 내부에 수소화 촉매가 고정된 수소화 반응기; 수소화 반응기로부터 생성된 네오펜틸 글리콜 생성물을 배출시키는 배출배관; 상기 배출배관으로부터 일부 네오펜틸 글리콜 생성물을 상기 피드 배슬에 공급하는 네오펜틸 글리콜 회수배관; 상기 배출배관으로부터 일부 네오펜틸 글리콜 생성물을 상기 수소화 반응기로 재순환 시키는 재순환 배관; 및 상기 원료공급배관을 통해 수소화 반응기로 공급되는 히드록시피브알데히드 용액을 수소화 반응기로 투입되기 직전에 가열시키는 가열장치;를 포함하는 것을 특징으로 하는네오펜틸 글리콜의 제조장치.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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US14/906,155 US9914682B2 (en) | 2014-09-25 | 2015-09-15 | Highly efficient neopentyl glycol preparation method and device therefor |
EP15820424.8A EP3187481B1 (en) | 2014-09-25 | 2015-09-15 | Method for preparing neopentyl glycol at high efficiency and apparatus for preparing same |
CN201580001734.4A CN105658609B (zh) | 2014-09-25 | 2015-09-15 | 高效的新戊二醇制备方法及用于该方法的装置 |
JP2016550448A JP6280654B2 (ja) | 2014-09-25 | 2015-09-15 | 高効率のネオペンチルグリコールの製造方法及びその製造装置 |
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KR1020150129657A KR101757053B1 (ko) | 2014-09-25 | 2015-09-14 | 고효율의 네오펜틸 글리콜의 제조방법 및 이의 제조장치 |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0484800B1 (en) * | 1990-11-06 | 1995-09-27 | Mitsubishi Gas Chemical Company, Inc. | Process for producing neopentyl glycol |
KR20010033761A (ko) * | 1997-12-30 | 2001-04-25 | 코르피 크리스티나 | 네오펜틸 글리콜의 제조 방법 |
KR20060073044A (ko) | 2004-12-24 | 2006-06-28 | 주식회사 엘지화학 | 네오펜틸글리콜의 제조방법 |
US20110098515A1 (en) * | 2008-07-02 | 2011-04-28 | Kurt Schalapski | Method of producing neopentyl glycol |
US20110184212A1 (en) * | 2008-07-15 | 2011-07-28 | Oxea Gmbh | Process for preparing neopentyl glycol by cracking high boilers occuring in the production process |
-
2015
- 2015-09-15 WO PCT/KR2015/009661 patent/WO2016047957A1/ko active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0484800B1 (en) * | 1990-11-06 | 1995-09-27 | Mitsubishi Gas Chemical Company, Inc. | Process for producing neopentyl glycol |
KR20010033761A (ko) * | 1997-12-30 | 2001-04-25 | 코르피 크리스티나 | 네오펜틸 글리콜의 제조 방법 |
KR20060073044A (ko) | 2004-12-24 | 2006-06-28 | 주식회사 엘지화학 | 네오펜틸글리콜의 제조방법 |
US20110098515A1 (en) * | 2008-07-02 | 2011-04-28 | Kurt Schalapski | Method of producing neopentyl glycol |
US20110184212A1 (en) * | 2008-07-15 | 2011-07-28 | Oxea Gmbh | Process for preparing neopentyl glycol by cracking high boilers occuring in the production process |
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