KR101948440B1 - Treating method of dearomatized hydrocarbon for the production of n-hexane, iso-hexane and heptane mixture - Google Patents
Treating method of dearomatized hydrocarbon for the production of n-hexane, iso-hexane and heptane mixture Download PDFInfo
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- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
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Abstract
Description
본 발명은 방향족 처리공정 (이하, " 방향족 공정" 이라고 함) 에서 부산물로 생성되는 탈방향족된 유분 (이하, "탈방향족 유분" 이라고도 함)을 원료로 활용하여 증류 공정 및 의사 이동층 공정을 조합하여, 다양한 순도의 노말 헥산과 95% 순도의 이소 헥산 및 헵탄 혼합물을 제조하는 방법에 관한 것이다.The present invention relates to a process for producing a dearomatized oil fraction (hereinafter also referred to as "dearomatic oil fraction") produced as a by-product in an aromatic treatment process (hereinafter referred to as an "aromatic process" To prepare a mixture of isohexane and heptane of various purity of normal hexane and 95% purity.
방향족 화합물 처리공정(이하, "방향족 공정"이라고도 함)은 원료인 나프타(naphtha)를 처리하여 파라-자일렌(para-xylene, PX)과 벤젠 (benzene, BZ)을 제조하는 공정이다. 종래의 방향족 공정에 있어서, 주요 제품 중 하나인 파라-자일렌(PX)이 포함되는 혼합 자일렌이 만들어지는 근원 공정은, 리포머(reformer) 공정, 자일렌 이성질화 공정 및 탄소수 7개의 방향족 화합물과 탄소수 9개의 방향족 화합물의 트랜스알킬화 및 불균등화 공정의 3가지 공정을 포함하고 있다. 도 1에 전형적인 방향족 화합물 처리공정에 대한 개략도를 나타내었다. An aromatic compound treatment process (hereinafter also referred to as "aromatic process") is a process for producing par-xylene (PX) and benzene (BZ) by treating naphtha as a raw material. In a conventional aromatic process, a source process for producing a mixed xylene containing para-xylene (PX), which is one of main products, is a reformer process, a xylene isomerization process, And transalkylation and disproportionation of aromatic compounds having 9 carbon atoms. Figure 1 shows a schematic diagram of a typical aromatics treatment process.
방향족 공정의 주제품인 벤젠과 자일렌은 방향족 화합물이기 때문에 이들을 이와 같은 방향족 공정에 있어서 설포란 (Sulfolane) 공정에서 방향족 화합물이 제거된 유분인 탈방향족 유분이 부산물로 배출되는데 이는 단순히 납사분해센터 (Naphtha Cracking Center) 원료로만 사용 되어서 고부가화되지 못해 왔다.Since benzene and xylene, which are main products of aromatic process, are aromatic compounds, in aromatic processes such as these, aromatic products are removed from aromatics in the sulfolane process as byproducts, which are simply naphtha cracking centers (Naphtha Cracking Center) has been used only as a raw material and has not been high-priced.
본 발명은 상기한 바와 같은 단순히 납사분해센터(Naphtha Cracking Center) 원료로만 사용 되던 탈방향족 유분을 고부가화 하기 위해 안출된 발명으로, 본 발명의 목적은 방향족 공정 부산물로 배출되는 탈방향족 유분을 원료로 하여 63%, 99% 순도의 노말 헥산과 95% 순도의 이소 헥산 및 헵탄 혼합물을 제조함으로써, 전체적으로 수익성이 현저히 개선된 탈방향족 유분 처리방법을 제공하는 것이다. The object of the present invention is to provide a dearomatic oil fraction discharged as an aromatic process by-product, as a raw material, and to provide a dearomatic oil fraction which is used only as a raw material of a naphtha cracking center, To provide a mixture of isohexane and heptane of normal purity of 63% and 99% purity of normal hexane and 95% purity, thereby providing a method of treating a dearomatic oilseed which is remarkably improved in profitability as a whole.
방향족 공정의 부산물로 제조되는 탈방향족된 유분을 1차 증류탑에 투입하여 탄소수 5개 이하의 가벼운 성분을 제거한 후 이를 2차 증류탑에 투입하여 탄소수 6개인 흐름과 7개 이상인 흐름으로 분리한 후, 이를 수첨 반응기에 투입하여 올레핀을 제거한 후 3차 증류탑으로 투입하면 증류탑 하부에서는 63% n-hexane을 얻을 수 있다. 99% 순도의 노말 헥산은 2차 증류탑 상부 흐름과 4차 증류탑 하부 흐름을 건조기를 통과시켜 수분을 제거하고 이를 의사 이동층으로 주입하여 이로부터 배출되는 흐름 중 extract 흐름을 증류탑으로 주입하여 증류탑 상부로는 탈착제를 회수하고 하부로는 99% 이상의 고순도 노말 헥산을 제조하고, 95% 순도의 이소 헥산은 (a) 3차 증류탑 상부 흐름을 4차 증류탑으로 투입하여 4차 증류탑의 상부로부터 95% 이소 헥산을 제조하거나, 또는 (b) 의사 이동층에서 나오는 raffinate 흐름을 증류탑으로 주입하여 증류탑 상부로는 탈착제를 회수하고 하부로는 95% 순도의 이소 헥산을 제조하게 된다. 의사 이동층에서는 hexane 보다 끓는점이 낮은 n-paraffin인 프로판, 부탄, 펜탄 중에서 선택된 1종을 탈착제로 사용하여 이후 증류탑에서 쉽게 분리하여 재사용할 수 있도록 한다. 의사 이동층 장치에 대해서는 한국 특허공개공보 제10-2007-0067926호(2007. 06. 29), 한국 특허공개공보 제10-2007-0067925호(2007. 06. 29) 등에 상세히 소개되어 있으므로 여기에서는 따로 언급하지 않는다.The dearomatized oil produced as a byproduct of the aromatic process is introduced into the first distillation column to remove light components of less than 5 carbon atoms and then introduced into the second distillation column to separate into a flow of 6 carbon atoms and a flow of 7 or more When the olefin is removed by adding it to the hydrogenation reactor and then introduced into the third distillation column, 63% n-hexane can be obtained at the bottom of the distillation column. Native hexane of 99% purity is passed through the drier to remove the water from the upper stream of the second distillation tower and the bottom stream of the fourth distillation tower. The extract stream is injected into the distillation column, Isohexane having a purity of 95% is prepared by: (a) feeding the upper stream of the tertiary distillation column to the fourth distillation column and recovering 95% isohexane from the upper part of the fourth distillation column; Hexane, or (b) raffinate stream from the pseudo-mobile layer is injected into the distillation column to recover the desorbent at the top of the distillation column and to produce isohexane at 95% purity as the bottom. In the simulated moving bed, one selected from n-paraffin, propane, butane and pentane, which has a lower boiling point than hexane, is used as a desorbent and can be easily separated from the distillation column for reuse. The pseudo moving bed apparatus is disclosed in detail in Korean Patent Laid-Open Publication No. 10-2007-0067926 (2007. 06. 29) and Korean Patent Laid-Open Publication No. 10-2007-0067925 (2007. 06. 29) It is not mentioned separately.
한편 2차 증류탑의 하부로 나오는 탄소수 7개 이상의 흐름을 추가 증류탑을 거쳐 탄소수 8개 이상의 무거운 성분을 제거한 후 수첨반응기를 거치게 되면 탄소수 7개로만 구성된 헵탄 혼합물 (mixed heptane)을 얻게 된다.On the other hand, if the heavier components of more than 8 carbon atoms are removed from the bottom of the second distillation tower through the additional distillation column, the heptane mixture consisting of only 7 carbon atoms is obtained.
본 발명의 탈방향족 유분 처리공정에 따르면, 방향족 공정에서 부산물로 배출되는 탈방향족 유분을 활용하여 다양한 순도의 노말 헥산과 이소 헥산 및 헵탄 혼합물을 제조할 수 있으므로 종래의 탈방향족 유분을 단순히 납사분해센터 (Naphtha Cracking Center)원료로만 활용하는 경우에 비하여, 부산물의 효과적인 재활용에 의해 수익성을 현저히 향상시킬 수 있다. According to the dearomatic oil treatment process of the present invention, it is possible to produce a mixture of n-hexane, isohexane and heptane of various purity using a dearomatic oil fraction discharged as a by-product in an aromatic process. Therefore, (Naphtha Cracking Center) As compared with the case where only the raw material is used, the profitability can be remarkably improved by effectively recycling by-products.
도 1은 일반적인 파라자일렌 생산을 위한 방향족 공정의 공정 개략도이다.
도 2는 탈방향족된 유분으로부터 노말 헥산, 이소 헥산 및 헵탄 혼합물을 생산하기 위한 공정 개략도이다.BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a schematic process diagram of an aromatic process for producing para-xylene in general.
Figure 2 is a schematic diagram of a process for producing a mixture of n-hexane, isohexane and heptane from de-aromatics.
이하, 실시예 및 비교예를 통하여 본 발명을 보다 상세히 설명하나, 이들 실시예 및 비교예에 의하여 본 발명의 범위가 제한되는 것은 아니다.Hereinafter, the present invention will be described in more detail by way of examples and comparative examples, but the scope of the present invention is not limited by these examples and comparative examples.
비교예Comparative Example
도 1에 나타낸 바와 같은 구성을 갖는 방향족 화합물 처리 공정에 있어서, 부산물로 제조되는 탈방향족 유분을 단순히 납사분해센터 원료로 사용하면 그 유분의 가치는 납사와 동일하다고 할 수 있다.In the aromatic compound treatment process having the constitution as shown in Fig. 1, when the dearomatic oil fraction produced as a by-product is simply used as a raw material for naphtha cracking center, the value of the oil fraction can be said to be the same as that of naphtha.
실시예Example
방향족 화합물 처리 공정에 있어서, 부산물로 제조되는 탈방향족 유분을 도 2에 제시한 공정으로 처리하여 63%, 99% 순도의 노말 헥산 95% 순도의 이소 헥산 및 헵탄 혼합물을 제조함으로써, 전체적으로 수익성을 향상시킬 수 있다. 본 실시 예에 따른, 도 2에 나타난 각 흐름 별 물질수지 및 수익성 개선 효과는 다음 표 1과 같다.In the aromatic compound treatment process, the dearomatic oil fraction produced as a by-product is treated with the process shown in FIG. 2 to produce an isohexane / heptane mixture having a purity of normal purity of n-hexane of 63% and 99% . The effect of improving the mass balance and profitability of each flow shown in FIG. 2 according to this embodiment is shown in Table 1 below.
A6: 탄소수 6개의 방향족
A7: 탄소수 7개의 방향족
A8: 탄소수 8개의 방향족
A9: 탄소수 9개의 방향족
A8's: 탄소수 8개의 방향족들
A10+: 탄소수 10개 이상의 방향족
Col 1: 증류탑 1
Col 2: 증류탑 2
Col 3: 증류탑 3
Col 4: 증류탑 4
RX 1: 수첨 반응기 1
RX 2: 수첨 반응기 2
SMB: 의사 이동층 분리 장치
C5~C6: 탄소수 5~6 의 유분
C7+: 탄소수 7이상의 유분
C7s: 탄소수 7개의 유분들
C8s: 탄소수 8개의 유분들A6: aromatic group having 6 carbon atoms
A7: aromatic group having 7 carbon atoms
A8: 8-carbon aromatic
A9: 9-carbon aromatic
A8's: 8 carbons
A10 < + >: aromatic having 10 or more carbon atoms
Col 1:
Col 2:
Col 3:
Col 4:
RX 1:
RX 2:
SMB: Pseudo moving bed separation device
C5 to C6: C5 to C6
C7 +: C 7 +
C7s: 7 carbon atoms
C8s: 8 carbon atoms
Claims (5)
(i) 상기 63% 순도의 노말 헥산으로는, 상기 탈방향족된 유분을 증류탑(1)에 투입하여 탄소수 5개 이하의 가벼운 성분을 제거하고, 탄소수 5개 이하의 가벼운 성분이 제거된 탈방향족된 유분을 증류탑(2)에 투입하여, 탄소수 6개인 흐름과 탄소수 7개 이상인 흐름으로 분리한 뒤, 분리된 상기 탄소수 6개인 흐름을 수소첨가 반응기(1)에 투입하여 올레핀을 제거한 후, 증류탑(3)에 투입하여 증류탑(3) 하부에서 63% 의 노말 헥산을 제조하는 것이고,
(ii) 상기 99% 순도의 노말 헥산으로는, 증류탑(2) 상부 흐름과 증류탑(4) 하부 흐름을 건조기를 통과시켜 수분을 제거하고, 상기 수분이 제거된 증류탑(2) 상부 흐름과 증류탑(4) 하부 흐름을 의사 이동층으로 주입하여 이로부터 배출되는 흐름 중 익스트렉트(extract) 흐름을 증류탑으로 주입하여 증류탑 상부로는 탈착제를 회수하고 하부로는 99% 이상의 고순도 노말 헥산을 제조하고,
(iii) 95% 순도의 이소 헥산으로는, (a) 증류탑(3) 상부 흐름을 증류탑(4)로 투입하여 증류탑(4)의 상부로부터 95% 이소 헥산을 제조하거나, 또는 (b) 의사 이동층에서 나오는 라피네이트(raffinate) 흐름을 증류탑으로 주입하여 증류탑 상부로는 탈착제를 회수하고 하부로는 95% 순도의 이소 헥산을 제조하는 것이고,
(iv) 상기 헵탄 혼합물로는, 증류탑(2)의 하부에서 나오는 탄소수 7개 이상의 흐름을 증류탑(5)로 주입하여 탄소수 8개의 유분을 증류탑 하부로 제거한 후, 상부로부터 나오는 흐름을 수소첨가 반응기(2)를 거쳐 탄소수 7개의 헵탄 혼합물을 제조하는 것을 특징으로 하는 탈방향족 유분 처리 방법.A method for treating dearomatic oils, characterized in that de-aromatics are treated to obtain a mixture of n-hexane of 63% and 99% purity and of isohexane and heptane of 95% purity,
(i) The n-hexane having the 63% purity can be obtained by introducing the dearomatic oil fraction into the distillation column 1 to remove the light component having 5 or less carbon atoms and removing the dearomatic The oil was introduced into the distillation column 2 and separated into a stream having six carbon atoms and a stream having seven or more carbon atoms. The separated stream of six carbon atoms was fed to the hydrogenation reactor 1 to remove the olefin, ) To produce 63% of normal hexane in the lower portion of the distillation column 3,
(ii) The n-hexane having a purity of 99% is prepared by passing the upper stream of the distillation column 2 and the lower stream of the distillation column 4 through a drier to remove water and then removing the moisture from the distillation column 2, 4) The lower stream is injected into the pseudo-mobile layer, and the extract stream is injected into the distillation column from the stream discharged therefrom. The desorbent is recovered to the upper part of the distillation column, and 99% or more of high purity normal hexane is produced ,
(iii) isohexane of 95% purity can be prepared by (a) introducing the stream above the distillation column 3 into the distillation column 4 to produce 95% isohexane from the top of the distillation column 4, or (b) The raffinate stream from the bed is injected into the distillation column to recover the desorbent to the top of the distillation column and to produce isohexane of 95% purity as the bottom.
(iv) As the heptane mixture, a stream having 7 or more carbon atoms derived from the lower part of the distillation column 2 is introduced into the distillation column 5 to remove the oil having 8 carbon atoms below the distillation column. 2) to produce a heptane mixture having 7 carbon atoms.
The method according to claim 1, wherein at least one selected from n-propane, n-butane and n-pentane is used as the desorbing agent for the pseudo-mobile layer.
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CN112225633A (en) * | 2020-10-29 | 2021-01-15 | 洛阳金达石化有限责任公司 | Production method of normal hexane containing heptane raw material |
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CN112225633A (en) * | 2020-10-29 | 2021-01-15 | 洛阳金达石化有限责任公司 | Production method of normal hexane containing heptane raw material |
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