CA2020406C - Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det - Google Patents

Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det

Info

Publication number: CA2020406C
Authority: CA; Canada
Prior art keywords: det; isomer; desorbent; adsorbent; feed
Prior art date: 1990-07-04
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 - Fee Related

Application number

CA 2020406

Other languages

English (en)

Other versions

CA2020406A1 (fr

Inventor

Hermann A. Zinnen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Honeywell UOP LLC

Original Assignee

UOP LLC

Priority date (The priority date 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 date listed.)

1990-07-04

Filing date

1990-07-04

Publication date

1999-07-06

1990-07-04 Application filed by UOP LLC filed Critical UOP LLC

1990-07-04 Priority to CA 2020406 priority Critical patent/CA2020406C/fr

1992-01-05 Publication of CA2020406A1 publication Critical patent/CA2020406A1/fr

1999-07-06 Application granted granted Critical

1999-07-06 Publication of CA2020406C publication Critical patent/CA2020406C/fr

2010-07-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 51
238000000034 method Methods 0.000 title claims description 53
238000013375 chromatographic separation Methods 0.000 title description 5
239000003463 adsorbent Substances 0.000 claims abstract description 89
239000010457 zeolite Substances 0.000 claims abstract description 63
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 47
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 47
229910052788 barium Inorganic materials 0.000 claims abstract description 24
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 23
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 19
229910052708 sodium Inorganic materials 0.000 claims abstract description 19
239000011734 sodium Substances 0.000 claims abstract description 19
238000003795 desorption Methods 0.000 claims abstract description 13
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052700 potassium Inorganic materials 0.000 claims abstract description 11
239000011591 potassium Substances 0.000 claims abstract description 11
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052802 copper Inorganic materials 0.000 claims abstract description 10
239000010949 copper Substances 0.000 claims abstract description 10
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052791 calcium Inorganic materials 0.000 claims abstract description 9
239000011575 calcium Substances 0.000 claims abstract description 9
238000001179 sorption measurement Methods 0.000 claims abstract description 9
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052744 lithium Inorganic materials 0.000 claims abstract description 5
XZZNTLNFQVAKFD-UHFFFAOYSA-N 1,3-diethyl-2-methylbenzene Chemical compound CCC1=CC=CC(CC)=C1C XZZNTLNFQVAKFD-UHFFFAOYSA-N 0.000 claims abstract description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims abstract description 3
DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 claims description 34
AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 claims description 26
239000000463 material Substances 0.000 claims description 25
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 12
239000007791 liquid phase Substances 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
150000002170 ethers Chemical class 0.000 claims description 5
150000008282 halocarbons Chemical class 0.000 claims description 5
HILAULICMJUOLK-UHFFFAOYSA-N 1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1 HILAULICMJUOLK-UHFFFAOYSA-N 0.000 abstract description 11
238000012360 testing method Methods 0.000 description 43
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 36
238000000926 separation method Methods 0.000 description 30
239000000700 radioactive tracer Substances 0.000 description 29
239000000047 product Substances 0.000 description 27
150000001768 cations Chemical group 0.000 description 20
239000000243 solution Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
230000000274 adsorptive effect Effects 0.000 description 7
PBWHJRFXUPLZDS-UHFFFAOYSA-N (1-Ethylpropyl)benzene Chemical compound CCC(CC)C1=CC=CC=C1 PBWHJRFXUPLZDS-UHFFFAOYSA-N 0.000 description 6
239000004927 clay Substances 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
239000011800 void material Substances 0.000 description 6
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 5
PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical class CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
-1 diethyltoluene diamines Chemical class 0.000 description 5
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 5
238000006317 isomerization reaction Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
229910000323 aluminium silicate Inorganic materials 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000012013 faujasite Substances 0.000 description 4
239000012535 impurity Substances 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910001422 barium ion Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
239000013078 crystal Substances 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
IOTUOULZCAHGBG-UHFFFAOYSA-N 2,4-diisocyanato-1-pentan-3-ylbenzene Chemical compound CCC(CC)C1=CC=C(N=C=O)C=C1N=C=O IOTUOULZCAHGBG-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920002396 Polyurea Polymers 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
229930007927 cymene Natural products 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910001416 lithium ion Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940094933 n-dodecane Drugs 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
150000002932 p-cymene derivatives Chemical class 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CA 2020406 1990-07-04 1990-07-04 Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det Expired - Fee Related CA2020406C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2020406 CA2020406C (fr)	1990-07-04	1990-07-04	Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2020406 CA2020406C (fr)	1990-07-04	1990-07-04	Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det

Publications (2)

Publication Number	Publication Date
CA2020406A1 CA2020406A1 (fr)	1992-01-05
CA2020406C true CA2020406C (fr)	1999-07-06

Family

ID=4145406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2020406 Expired - Fee Related CA2020406C (fr)	1990-07-04	1990-07-04	Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det

Country Status (1)

Country	Link
CA (1)	CA2020406C (fr)

1990
- 1990-07-04 CA CA 2020406 patent/CA2020406C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2020406A1 (fr)	1992-01-05

Legal Events

Date	Code	Title	Description
1994-09-08	EEER	Examination request
2003-07-04	MKLA	Lapsed

Publication	Publication Date	Title
US4886930A (en)	1989-12-12	Zeolitic para-xylene separation with tetralin heavy desorbent
EP0464277B1 (fr)	1995-11-22	Procédé pour la séparation par adsorption de 2,6- ou 3,5-diéthyltoluène à partir d'un mélange de celui-ci avec un autre isomère de diéthyltoluène
US5057643A (en)	1991-10-15	Zeolitic para-xylene separation with tetralin derivatives as heavy desorbent
EP0683148B1 (fr)	1997-12-03	Procédé pour la séparation d'éthylbenzène par adsorption sur de la zéolite X échangée au césium
US5849981A (en)	1998-12-15	Adsorptive separation of para-xylene using isopropylbenzene desorbent
US5012038A (en)	1991-04-30	Zeolitic para-xylene separation with diethyltoluene heavy desorbent
US4529828A (en)	1985-07-16	Separation of ortho-xylene
US4886929A (en)	1989-12-12	Separation of para-xylene
US5495061A (en)	1996-02-27	Adsorptive separation of para-xylene with high boiling desorbents
US5107062A (en)	1992-04-21	Zeolitic para-xylene separation with tetralin derivatives as heavy desorbent
US5159131A (en)	1992-10-27	Zeolitic para-xylene separation with indan and indan derivatives as heavy desorbent
US4482777A (en)	1984-11-13	Separation of ortho bi-alkyl substituted monocyclic aromatic isomers
HU205058B (en)	1992-03-30	Process for adsorption separation of paraxylol by using tetraline desorbent
US4876390A (en)	1989-10-24	Process for separating dichlorodiphenylsulfone isomers
US4956522A (en)	1990-09-11	Zeolitic para-ethyltoluene separation with tetralin heavy desorbent
CA2020406C (fr)	1999-07-06	Procede de separation chromatographique pour la recuperation du 2,6-det ou du 3,5-det d'un melange des deux avec un autre isomere det
US5019271A (en)	1991-05-28	Extractive chromatographic separation process for recovering 3,5-diethyltoluene
US5177300A (en)	1993-01-05	Process for separating naphthalene from substituted benzene hydrocarbons
US5223589A (en)	1993-06-29	Process for separating durene from substituted benzene hydrocarbons
KR930003210B1 (ko)	1993-04-23	다른 det 이성질체와의 혼합물로부터 2,6-det 또는 3.5-det를 크로마토그래피에 의하여 분리 및 회수하는 방법
AU636849B2 (en)	1993-05-13	Sharps destruction and disposal apparatus
US4992621A (en)	1991-02-12	Separation of coumarone from indene
JPH08143485A (ja)	1996-06-04	芳香族炭化水素からメタキシレンの吸着分離法
KR910009123B1 (ko)	1991-10-31	디에틸톨루엔 탈착제를 사용한 파라-크실렌의 흡착 분리공정
KR920002056B1 (ko)	1992-03-10	테트랄린 탈착제를 이용한 파라-크실렌의 흡수분리