CA1127139A - Production de cyclohexanone - Google Patents

Production de cyclohexanone

Info

Publication number: CA1127139A
Authority: CA; Canada
Prior art keywords: catalyst; palladium; phenol; hydrogenation; cyclohexanone
Prior art date: 1976-11-24
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

Application number

CA380,469A

Other languages

English (en)

Inventor

Jan F. Vanpeppen

William B. Fisher

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 International Inc

Original Assignee

Allied Corp

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.)

1976-11-24

Filing date

1981-06-23

Publication date

1982-07-06

1977-09-16 Priority claimed from CA286,935A external-priority patent/CA1109855A/fr

1981-06-23 Application filed by Allied Corp filed Critical Allied Corp

1981-06-23 Priority to CA380,469A priority Critical patent/CA1127139A/fr

1982-07-06 Application granted granted Critical

1982-07-06 Publication of CA1127139A publication Critical patent/CA1127139A/fr

Status Expired legal-status Critical Current

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 68
238000004519 manufacturing process Methods 0.000 title claims abstract description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 93
239000003054 catalyst Substances 0.000 claims abstract description 81
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 44
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 34
229910052763 palladium Inorganic materials 0.000 claims description 34
239000002245 particle Substances 0.000 claims description 27
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 description 16
239000011734 sodium Substances 0.000 claims description 16
229910052708 sodium Inorganic materials 0.000 claims description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 18
239000011541 reaction mixture Substances 0.000 abstract description 16
229910000029 sodium carbonate Inorganic materials 0.000 abstract description 12
238000011065 in-situ storage Methods 0.000 abstract description 6
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 abstract description 6
238000009835 boiling Methods 0.000 abstract description 4
230000003993 interaction Effects 0.000 abstract description 3
239000007791 liquid phase Substances 0.000 abstract 1
230000001737 promoting effect Effects 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 10
239000012535 impurity Substances 0.000 description 10
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
229910052717 sulfur Inorganic materials 0.000 description 8
239000011593 sulfur Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000003610 charcoal Substances 0.000 description 4
238000009826 distribution Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910017464 nitrogen compound Inorganic materials 0.000 description 4
150000002830 nitrogen compounds Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000002939 deleterious effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
-1 phenates Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000003057 platinum Chemical class 0.000 description 2
238000004064 recycling Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds 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
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000000135 prohibitive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA380,469A 1976-11-24 1981-06-23 Production de cyclohexanone Expired CA1127139A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA380,469A CA1127139A (fr)	1976-11-24	1981-06-23	Production de cyclohexanone

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US74453876A	1976-11-24	1976-11-24
US744,538		1976-11-24
US81539777A	1977-07-13	1977-07-13
US815,397		1977-07-13
CA286,935A CA1109855A (fr)	1976-11-24	1977-09-16	Production de cyclohexanone
CA380,469A CA1127139A (fr)	1976-11-24	1981-06-23	Production de cyclohexanone

Publications (1)

Publication Number	Publication Date
CA1127139A true CA1127139A (fr)	1982-07-06

Family

ID=27426028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA380,469A Expired CA1127139A (fr)	1976-11-24	1981-06-23	Production de cyclohexanone

Country Status (1)

Country	Link
CA (1)	CA1127139A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN118287099A (zh) *	2024-03-29	2024-07-05	南京工业大学	一种钯铁基催化剂及其制备方法和应用
CN118773625A (zh) *	2024-07-30	2024-10-15	江苏馨瑞香料有限公司	一种对叔丁基环己酮或其衍生物的制备方法、加氢催化剂及其制备方法

1981
- 1981-06-23 CA CA380,469A patent/CA1127139A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN118287099A (zh) *	2024-03-29	2024-07-05	南京工业大学	一种钯铁基催化剂及其制备方法和应用
CN118773625A (zh) *	2024-07-30	2024-10-15	江苏馨瑞香料有限公司	一种对叔丁基环己酮或其衍生物的制备方法、加氢催化剂及其制备方法

Legal Events

Date	Code	Title	Description
1999-07-06	MKEX	Expiry

Publication	Publication Date	Title
US4200553A (en)	1980-04-29	Process for producing cyclohexanone
CA2059719C (fr)	2002-10-08	Procede d'obtention d'acide terephtalique
EP0003858B1 (fr)	1981-07-15	Procédé pour éliminer sélectivement des petites quantités de bêta-chloroacroléine et de 5,6-époxyhexène-1 de l'épichlorohydrine
US4162267A (en)	1979-07-24	Production of cyclohexanone
JP2801381B2 (ja)	1998-09-21	高純度アニリンの製造法
JP2801358B2 (ja)	1998-09-21	高純度アニリンの製造方法
CA1127185A (fr)	1982-07-06	Toluene-diamine a partir de dinitrotoluene non lave
JPH04283531A (ja)	1992-10-08	ビスフェノールの製造方法
JP2002523483A (ja)	2002-07-30	改良されたヘキサメチレンジアミンの製造方法
EP0255389A1 (fr)	1988-02-03	Procédé de récupération de métaux
US4092360A (en)	1978-05-30	Production of cyclohexanone
CA1109855A (fr)	1981-09-29	Production de cyclohexanone
EP0221136B1 (fr)	1989-07-26	Procede de recuperation de catalyseur
CA1188325A (fr)	1985-06-04	Preparation de methyl-phenol
EP0168358B1 (fr)	1988-08-10	Procédé pour la pyrolyse de goudron phénolique
US5041682A (en)	1991-08-20	Working up reaction mixtures containing cyclohexanol cyclohexanone and cyclohexyl hydroperoxide
JPS637818B2 (fr)	1988-02-18
JPS62739B2 (fr)	1987-01-09
US3551511A (en)	1970-12-29	Method of purifying cumene in cumene phenol process
US4650615A (en)	1987-03-17	Purification of carboxylic acid anhydrides contaminated with halogen or halides
JPH0473423B2 (fr)	1992-11-20
US20060142615A1 (en)	2006-06-29	Process for preparing ethanolamine with improved colour
US3560560A (en)	1971-02-02	Purification of acetic acid
US4656279A (en)	1987-04-07	Process for production of decahydroisoquinoline
EP0337246B1 (fr)	1992-07-08	Procédé pour la fabrication de pyruvate

CA1127139A - Production de cyclohexanone - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (6)

Publications (1)

Family

ID=27426028

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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