CA1060876A - Preparation de la malachite - Google Patents

Preparation de la malachite

Info

Publication number: CA1060876A
Authority: CA; Canada
Prior art keywords: bismuth; copper; amount; catalyst; complex
Prior art date: 1974-02-25
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

CA303,138A

Other languages

English (en)

Inventor

Joseph M. Fremont

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1974-02-25

Filing date

1978-05-11

Publication date

1979-08-21

1975-02-24 Priority claimed from CA220,936A external-priority patent/CA1051610A/fr

1978-05-11 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1978-05-11 Priority to CA303,138A priority Critical patent/CA1060876A/fr

1979-08-21 Application granted granted Critical

1979-08-21 Publication of CA1060876A publication Critical patent/CA1060876A/fr

Status Expired legal-status Critical Current

Links

241000907663 Siproeta stelenes Species 0.000 title abstract description 39
238000002360 preparation method Methods 0.000 title description 4
239000003054 catalyst Substances 0.000 claims abstract description 59
229910052797 bismuth Inorganic materials 0.000 claims abstract description 56
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 54
239000002245 particle Substances 0.000 claims abstract description 39
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 claims abstract description 17
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 34
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 31
229940116318 copper carbonate Drugs 0.000 claims description 27
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 27
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 26
239000010949 copper Substances 0.000 claims description 26
229910052802 copper Inorganic materials 0.000 claims description 24
238000000034 method Methods 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 17
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
235000019256 formaldehyde Nutrition 0.000 claims description 13
230000008569 process Effects 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
239000002002 slurry Substances 0.000 claims description 6
239000012736 aqueous medium Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000001621 bismuth Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
230000000977 initiatory effect Effects 0.000 claims description 3
239000002243 precursor Substances 0.000 claims description 3
230000009471 action Effects 0.000 claims description 2
DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
230000006872 improvement Effects 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims 3
230000001376 precipitating effect Effects 0.000 claims 2
238000010899 nucleation Methods 0.000 abstract description 15
230000006911 nucleation Effects 0.000 abstract description 15
239000013078 crystal Substances 0.000 abstract description 10
238000009826 distribution Methods 0.000 abstract description 4
239000000243 solution Substances 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 18
239000000047 product Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
229960004279 formaldehyde Drugs 0.000 description 7
238000001556 precipitation Methods 0.000 description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
238000007792 addition Methods 0.000 description 5
239000000376 reactant Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
KBZSNAZVDVIXKL-UHFFFAOYSA-L bismuth copper carbonate Chemical compound [Cu+2].[Bi+3].[O-]C([O-])=O KBZSNAZVDVIXKL-UHFFFAOYSA-L 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
229910000014 Bismuth subcarbonate Inorganic materials 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229910000416 bismuth oxide Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 2
FWIZHMQARNODNX-UHFFFAOYSA-L dibismuth;oxygen(2-);carbonate Chemical compound [O-2].[O-2].[Bi+3].[Bi+3].[O-]C([O-])=O FWIZHMQARNODNX-UHFFFAOYSA-L 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
CBACFHTXHGHTMH-UHFFFAOYSA-N 2-piperidin-1-ylethyl 2-phenyl-2-piperidin-1-ylacetate;dihydrochloride Chemical compound Cl.Cl.C1CCCCN1C(C=1C=CC=CC=1)C(=O)OCCN1CCCCC1 CBACFHTXHGHTMH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
NPKGQBIUYHHPOT-UHFFFAOYSA-N [Cu+2].[C-]#[C-] Chemical compound [Cu+2].[C-]#[C-] NPKGQBIUYHHPOT-UHFFFAOYSA-N 0.000 description 1
150000000476 acetylides Chemical class 0.000 description 1
239000000159 acid neutralizing agent Substances 0.000 description 1
229940036358 bismuth subcarbonate Drugs 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000012018 catalyst precursor Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
DMRJVKOYZFHZJH-UHFFFAOYSA-L copper;hydrogen carbonate;hydroxide Chemical compound [OH-].[Cu+2].OC([O-])=O DMRJVKOYZFHZJH-UHFFFAOYSA-L 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
ZMMDPCMYTCRWFF-UHFFFAOYSA-J dicopper;carbonate;dihydroxide Chemical compound [OH-].[OH-].[Cu+2].[Cu+2].[O-]C([O-])=O ZMMDPCMYTCRWFF-UHFFFAOYSA-J 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
230000001788 irregular Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Landscapes

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

CA303,138A 1974-02-25 1978-05-11 Preparation de la malachite Expired CA1060876A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA303,138A CA1060876A (fr)	1974-02-25	1978-05-11	Preparation de la malachite

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US44547674A	1974-02-25	1974-02-25
CA220,936A CA1051610A (fr)	1974-02-25	1975-02-24	Preparation de malachite
CA303,138A CA1060876A (fr)	1974-02-25	1978-05-11	Preparation de la malachite

Publications (1)

Publication Number	Publication Date
CA1060876A true CA1060876A (fr)	1979-08-21

Family

ID=27163830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,138A Expired CA1060876A (fr)	1974-02-25	1978-05-11	Preparation de la malachite

Country Status (1)

Country	Link
CA (1)	CA1060876A (fr)

1978
- 1978-05-11 CA CA303,138A patent/CA1060876A/fr not_active Expired

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