CA2476034C - Procede pour la recuperation d'un produit de carbonylation - Google Patents

Procede pour la recuperation d'un produit de carbonylation Download PDF

Info

Publication number: CA2476034C
Authority: CA; Canada
Prior art keywords: carbonylation; liquid; iridium; weight; concentration
Prior art date: 1993-03-26
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

Application number

CA002476034A

Other languages

English (en)

Other versions

CA2476034A1 (fr

Inventor

Kirsten Everald Clode

Derrick John Watson

Carl Jozef Elsa Vercauteren

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.)

BP Chemicals Ltd

Original Assignee

BP Chemicals Ltd

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.)

1993-03-26

Filing date

1994-03-22

Publication date

2008-07-29

1993-03-26 Priority claimed from GB939306409A external-priority patent/GB9306409D0/en

1994-03-22 Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd

1994-09-27 Publication of CA2476034A1 publication Critical patent/CA2476034A1/fr

2008-07-29 Application granted granted Critical

2008-07-29 Publication of CA2476034C publication Critical patent/CA2476034C/fr

2014-03-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000005810 carbonylation reaction Methods 0.000 title claims abstract description 140
230000006315 carbonylation Effects 0.000 title claims abstract description 91
238000000034 method Methods 0.000 title claims abstract description 42
238000011084 recovery Methods 0.000 title description 12
239000007788 liquid Substances 0.000 claims abstract description 81
239000000203 mixture Substances 0.000 claims abstract description 61
150000002148 esters Chemical class 0.000 claims abstract description 51
239000000376 reactant Substances 0.000 claims abstract description 51
239000003054 catalyst Substances 0.000 claims abstract description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
229910001868 water Inorganic materials 0.000 claims abstract description 45
229910052741 iridium Inorganic materials 0.000 claims abstract description 44
-1 hydrocarbyl halide Chemical class 0.000 claims abstract description 30
238000006243 chemical reaction Methods 0.000 claims abstract description 21
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 16
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 13
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 29
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 21
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 20
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims 1
FPHQLDRCDMDGQW-UHFFFAOYSA-N iridium Chemical compound [Ir].[Ir] FPHQLDRCDMDGQW-UHFFFAOYSA-N 0.000 description 46
239000000047 product Substances 0.000 description 44
238000009834 vaporization Methods 0.000 description 28
238000004821 distillation Methods 0.000 description 24
150000004820 halides Chemical class 0.000 description 21
238000012360 testing method Methods 0.000 description 15
239000000243 solution Substances 0.000 description 12
238000000926 separation method Methods 0.000 description 10
238000009835 boiling Methods 0.000 description 7
238000013112 stability test Methods 0.000 description 7
238000004508 fractional distillation Methods 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
239000007791 liquid phase Substances 0.000 description 5
239000011550 stock solution Substances 0.000 description 5
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
238000009616 inductively coupled plasma Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000036961 partial effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000010586 diagram Methods 0.000 description 2
210000003918 fraction a Anatomy 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 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 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
150000001983 dialkylethers Chemical group 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
KZLHPYLCKHJIMM-UHFFFAOYSA-K iridium(3+);triacetate Chemical compound [Ir+3].CC([O-])=O.CC([O-])=O.CC([O-])=O KZLHPYLCKHJIMM-UHFFFAOYSA-K 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
150000002835 noble gases Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA002476034A 1993-03-26 1994-03-22 Procede pour la recuperation d'un produit de carbonylation Expired - Lifetime CA2476034C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB9306409.5		1993-03-26
GB939306409A GB9306409D0 (en)	1993-03-26	1993-03-26	Process
CA002119609A CA2119609C (fr)	1993-03-26	1994-03-22	Procede pour la recuperation d'un produit de carbonylation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002119609A Division CA2119609C (fr)	1993-03-26	1994-03-22	Procede pour la recuperation d'un produit de carbonylation

Publications (2)

Publication Number	Publication Date
CA2476034A1 CA2476034A1 (fr)	1994-09-27
CA2476034C true CA2476034C (fr)	2008-07-29

Family

ID=32991572

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002476034A Expired - Lifetime CA2476034C (fr)	1993-03-26	1994-03-22	Procede pour la recuperation d'un produit de carbonylation

Country Status (1)

Country	Link
CA (1)	CA2476034C (fr)

1994
- 1994-03-22 CA CA002476034A patent/CA2476034C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2476034A1 (fr)	1994-09-27

Legal Events

Date	Code	Title	Description
2004-08-26	EEER	Examination request
2014-05-26	MKEX	Expiry	Effective date: 20140324

Publication	Publication Date	Title
CA2119609C (fr)	2005-05-17	Procede pour la recuperation d'un produit de carbonylation
KR100591051B1 (ko)	2006-06-19	아세트산 제조를 위한 무수 카르보닐화 방법
CA2154028C (fr)	2006-07-11	Procede de purification d'un acide carboxylique
KR100192733B1 (ko)	1999-06-15	카보닐화 스트림으로부터 카보닐 불순물을 제거하는 방법
KR100408144B1 (ko)	2004-03-30	카보닐화공정동안형성된희석수성스트림으로부터아세트산을회수하는방법
AU647314B2 (en)	1994-03-17	Process for the purification of carboxylic acids and/or their anhydrides
US5883295A (en)	1999-03-16	Iridium catalyzed carbonylation process for the production of acetic acid
EP2220022B1 (fr)	2015-10-28	Procédé et appareil de fabrication d'acide acétique ayant une productivité améliorée
JPH0532581A (ja)	1993-02-09	カルボニル化方法
US5364822A (en)	1994-11-15	Process for the recovery of group VIII noble metals
EP0665210B1 (fr)	1998-11-04	Procede pour produire de l'anhydride acetique seul ou en combinaison avec de l'acide acetique
JPWO1995005356A1 (ja)	1995-09-07	無水酢酸又は無水酢酸及び酢酸の製造方法
EP0321054B1 (fr)	1996-03-06	Procédé de production d'esters de l'acide propionique
CA2476034C (fr)	2008-07-29	Procede pour la recuperation d'un produit de carbonylation
US5990347A (en)	1999-11-23	Process for preparing a carboxylic acid
NZ280089A (en)	1996-11-26	Preparation of carboxylic acids by carbonylation of alcohols having one less carbon atom in the presence of an iridium carbonylation catalyst