ZA200401196B - Process for the production of acetic acid C4-esters. - Google Patents

Process for the production of acetic acid C4-esters. Download PDF

Info

Publication number: ZA200401196B
Authority: ZA; South Africa
Prior art keywords: stream; butene; acetate; addition; butadiene
Prior art date: 2001-08-30

Application number

ZA200401196A

Other languages

English (en)

Inventor

Patrick Benjamin Gracey

Nicholas John Hazel

Original Assignee

Univ Southern Mississipi Res F

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.)

2001-08-30

Filing date

2004-02-13

Publication date

2004-10-22

2004-02-13 Application filed by Univ Southern Mississipi Res F filed Critical Univ Southern Mississipi Res F

2004-10-22 Publication of ZA200401196B publication Critical patent/ZA200401196B/en

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 93
238000000034 method Methods 0.000 title claims description 37
238000004519 manufacturing process Methods 0.000 title description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 57
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 52
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 29
NLAMRLZPVVKXTK-UHFFFAOYSA-N but-1-enyl acetate Chemical compound CCC=COC(C)=O NLAMRLZPVVKXTK-UHFFFAOYSA-N 0.000 claims description 18
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 16
BVCLXNHIJBDDTH-UHFFFAOYSA-N but-1-en-2-yl acetate Chemical compound CCC(=C)OC(C)=O BVCLXNHIJBDDTH-UHFFFAOYSA-N 0.000 claims description 15
238000007259 addition reaction Methods 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 10
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 10
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 8
KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 6
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 6
238000004230 steam cracking Methods 0.000 claims description 5
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
239000002638 heterogeneous catalyst Substances 0.000 claims description 4
239000003112 inhibitor Substances 0.000 claims description 4
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 3
LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims description 3
239000001273 butane Substances 0.000 claims description 3
WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 claims description 3
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims description 3
125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 3
239000003456 ion exchange resin Substances 0.000 claims description 3
229920003303 ion-exchange polymer Polymers 0.000 claims description 3
239000001282 iso-butane Substances 0.000 claims description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 3
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
238000006356 dehydrogenation reaction Methods 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
239000010457 zeolite Substances 0.000 claims description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
229910021536 Zeolite Inorganic materials 0.000 claims 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 36
239000000203 mixture Substances 0.000 description 22
-1 1 - 2 %v/v) Chemical compound 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 14
239000003054 catalyst Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
239000006227 byproduct Substances 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
150000001242 acetic acid derivatives Chemical class 0.000 description 5
238000000926 separation method Methods 0.000 description 5
229920002367 Polyisobutene Polymers 0.000 description 4
150000001336 alkenes Chemical class 0.000 description 4
235000013844 butane Nutrition 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NLAMRLZPVVKXTK-SNAWJCMRSA-N [(e)-but-1-enyl] acetate Chemical group CC\C=C\OC(C)=O NLAMRLZPVVKXTK-SNAWJCMRSA-N 0.000 description 2
WNHXJHGRIHUOTG-ONEGZZNKSA-N [(e)-but-2-enyl] acetate Chemical group C\C=C\COC(C)=O WNHXJHGRIHUOTG-ONEGZZNKSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005336 cracking Methods 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000002816 fuel additive Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000004064 recycling Methods 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000003068 static effect Effects 0.000 description 2
239000011269 tar Substances 0.000 description 2
239000013638 trimer Substances 0.000 description 2
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical group [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
OAIYNRAQCIOEBD-UHFFFAOYSA-N butyl acetate;hydrate Chemical compound O.CCCCOC(C)=O OAIYNRAQCIOEBD-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
QTYUSOHYEPOHLV-UHFFFAOYSA-N octadiene group Chemical group C=CC=CCCCC QTYUSOHYEPOHLV-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000005496 phosphonium group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200401196A 2001-08-30 2004-02-13 Process for the production of acetic acid C4-esters. ZA200401196B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0120989.9A GB0120989D0 (en)	2001-08-30	2001-08-30	Process for treating a mixed c4 stream comprising iso-butene and 1,3-butadiene

Publications (1)

Publication Number	Publication Date
ZA200401196B true ZA200401196B (en)	2004-10-22

Family

ID=9921198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200401196A ZA200401196B (en)	2001-08-30	2004-02-13	Process for the production of acetic acid C4-esters.

Country Status (13)

Country	Link
US (1)	US6949671B2 (de)
EP (1)	EP1421053B1 (de)
JP (1)	JP2005518341A (de)
KR (1)	KR20040029044A (de)
CN (1)	CN1237044C (de)
AT (1)	ATE356793T1 (de)
BR (1)	BR0212162A (de)
DE (1)	DE60218868D1 (de)
GB (1)	GB0120989D0 (de)
PL (1)	PL367725A1 (de)
RU (1)	RU2004109816A (de)
WO (1)	WO2003020681A1 (de)
ZA (1)	ZA200401196B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20060021358A (ko) *	2003-06-16	2006-03-07	더 유니버시티 오브 서던 미시시피 리서치 파운데이션	부타디엔 첨가 산물 유도체의 통합적 제조 방법
CN100463897C (zh) *	2007-02-02	2009-02-25	胡先念	一种从乙酸与混合c4反应后的混合物中分离乙酸仲丁酯的方法
KR101107621B1 (ko) *	2009-04-27	2012-01-30	어코드 주식회사	원통형 열교환기를 갖는 국솥
CN102234230A (zh) *	2010-05-05	2011-11-09	北京石油化工学院	用c4馏分合成醋酸仲丁酯的工艺方法
CN102372628A (zh) *	2010-08-13	2012-03-14	中国石油化工股份有限公司	一种制备乙酸叔丁酯的方法
WO2026131321A1 (en)	2024-12-18	2026-06-25	Basf Se	Process for manufacturing polyisobutene with a higher efficiency

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3105399A1 (de) *	1981-02-14	1982-10-21	EC Erdölchemie GmbH, 5000 Köln	Verfahren zur herstellung von carbonsaeureestern
GB9823853D0 (en)	1998-10-30	1998-12-23	Bp Chem Int Ltd	A process for making n-butyl esters from butadiene

2001
- 2001-08-30 GB GBGB0120989.9A patent/GB0120989D0/en not_active Ceased
2002
- 2002-08-28 KR KR10-2004-7002807A patent/KR20040029044A/ko not_active Withdrawn
- 2002-08-28 BR BR0212162-0A patent/BR0212162A/pt not_active Application Discontinuation
- 2002-08-28 RU RU2004109816/04A patent/RU2004109816A/ru not_active Application Discontinuation
- 2002-08-28 CN CNB028169794A patent/CN1237044C/zh not_active Expired - Fee Related
- 2002-08-28 DE DE60218868T patent/DE60218868D1/de not_active Expired - Lifetime
- 2002-08-28 PL PL02367725A patent/PL367725A1/xx not_active IP Right Cessation
- 2002-08-28 US US10/487,450 patent/US6949671B2/en not_active Expired - Fee Related
- 2002-08-28 WO PCT/GB2002/003930 patent/WO2003020681A1/en not_active Ceased
- 2002-08-28 AT AT02755255T patent/ATE356793T1/de not_active IP Right Cessation
- 2002-08-28 JP JP2003524953A patent/JP2005518341A/ja not_active Ceased
- 2002-08-28 EP EP02755255A patent/EP1421053B1/de not_active Expired - Lifetime
2004
- 2004-02-13 ZA ZA200401196A patent/ZA200401196B/en unknown

Also Published As

Publication number	Publication date
US6949671B2 (en)	2005-09-27
CN1237044C (zh)	2006-01-18
PL367725A1 (en)	2005-03-07
DE60218868D1 (de)	2007-04-26
BR0212162A (pt)	2004-07-13
EP1421053A1 (de)	2004-05-26
KR20040029044A (ko)	2004-04-03
CN1549806A (zh)	2004-11-24
EP1421053B1 (de)	2007-03-14
JP2005518341A (ja)	2005-06-23
WO2003020681A1 (en)	2003-03-13
GB0120989D0 (en)	2001-10-24
RU2004109816A (ru)	2005-10-20
ATE356793T1 (de)	2007-04-15
US20040249192A1 (en)	2004-12-09

Publication	Publication Date	Title
US5382707A (en)	1995-01-17	Integrated MTBE process
JPS6228933B2 (de)	1987-06-23
KR19980033193A (ko)	1998-07-25	4개의 탄소 원자를 포함하는 탄화수소 분급물로부터 이소부텐및 프로필렌을 제조하는 신규한 방법
JPH01213248A (ja)	1989-08-28	エーテルの製造方法
CA2959446A1 (en)	2016-03-17	Method and apparatus for producing hydrocarbons
KR100513915B1 (ko)	2005-09-13	3급-부틸 알콜의 제조방법
KR101331553B1 (ko)	2013-11-20	글리콜에테르를 이용한 고순도 이소부텐의 제조 방법
KR100681223B1 (ko)	2007-02-09	부타디엔으로부터 ｎ-부틸 에스테르를 제조하는 방법
EP1421053B1 (de)	2007-03-14	Verfahren zur herstellung von essigsäure-c4-estern
JP2691223B2 (ja)	1997-12-17	イソアミレン中の２‐メチル‐２‐ブテン濃度の増加
CN110172013B (zh)	2023-06-16	一种基于催化蒸馏溶剂法合成叔戊醇的工艺
JP2612194B2 (ja)	1997-05-21	線状オレフインの直接水加法
GB2121407A (en)	1983-12-21	Process for producing t-butyl alkyl ethers
EP3606900B1 (de)	2025-11-05	Systeme und verfahren zur herstellung von methyltertiärem butylether und propylen
EP0196037A2 (de)	1986-10-01	Verfahren zur Herstellung von tert.-Butanol und gegebenenfalls Methyl tert.-butylether und/oder Ethyl-tert.-butylether
US6403839B1 (en)	2002-06-11	Process for making butyraldehyde from butadiene
CN114456029B (zh)	2024-07-23	从碳四烃制备1-丁烯的方法和装置
JPS6358811B2 (de)	1988-11-17
GB1589457A (en)	1981-05-13	Method for purifying methyl tert butyl ether
JPS6115849B2 (de)	1986-04-26
WO1991015454A1 (en)	1991-10-17	Method for preparing 1,4-diacyloxy-2-butenes
RO121848B1 (ro)	2008-06-30	Procedeu şi instalaţie de obţinere a dimerilorşi codimerilor de butene