NL8103758A - Werkwijze voor het selectief bereiden van polyalkyleenpolyamines. - Google Patents

Werkwijze voor het selectief bereiden van polyalkyleenpolyamines. Download PDF

Info

Publication number: NL8103758A
Authority: NL; Netherlands
Prior art keywords: compound; alkanolamine; cyclic; phosphorus; polyalkylene
Prior art date: 1980-08-28

Application number

NL8103758A

Other languages

English (en)

Dutch (nl)

Original Assignee

Texaco Development 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.)

1980-08-28

Filing date

1981-08-11

Publication date

1982-03-16

1981-08-11 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1982-03-16 Publication of NL8103758A publication Critical patent/NL8103758A/nl

Links

238000000034 method Methods 0.000 title claims description 45
229920000768 polyamine Polymers 0.000 title claims description 37
229920001281 polyalkylene Polymers 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title description 7
-1 alkylene amine compound Chemical class 0.000 claims description 28
125000004122 cyclic group Chemical group 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 14
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
229910052698 phosphorus Inorganic materials 0.000 claims description 13
239000011574 phosphorus Substances 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
150000001768 cations Chemical class 0.000 claims description 8
239000007791 liquid phase Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
239000003729 cation exchange resin Substances 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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 description 3
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 2
229940005657 pyrophosphoric acid Drugs 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 23
239000000047 product Substances 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 9
239000004698 Polyethylene Substances 0.000 description 9
229920000573 polyethylene Polymers 0.000 description 9
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000000376 reactant Substances 0.000 description 8
229920002125 Sokalan® Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
238000006386 neutralization reaction Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
150000004885 piperazines Chemical class 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229960001124 trientine Drugs 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 2
238000010923 batch production Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
125000004970 halomethyl group Chemical group 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
238000007281 aminoalkylation reaction Methods 0.000 description 1
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
238000007265 chloromethylation reaction Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229910003460 diamond Inorganic materials 0.000 description 1
239000010432 diamond Substances 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
YQDHCCVUYCIGSW-LBPRGKRZSA-N ethyl (2s)-2-benzamido-5-(diaminomethylideneamino)pentanoate Chemical compound NC(=N)NCCC[C@@H](C(=O)OCC)NC(=O)C1=CC=CC=C1 YQDHCCVUYCIGSW-LBPRGKRZSA-N 0.000 description 1
125000003916 ethylene diamine group Chemical group 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/64—Preparation of compounds containing amino groups bound to a carbon skeleton by disproportionation
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8103758A 1980-08-28 1981-08-11 Werkwijze voor het selectief bereiden van polyalkyleenpolyamines. NL8103758A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/182,206 US4324917A (en)	1980-08-28	1980-08-28	Preparation of polyalkylene polyamines
US18220680		1980-08-28

Publications (1)

Publication Number	Publication Date
NL8103758A true NL8103758A (nl)	1982-03-16

Family

ID=22667468

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8103758A NL8103758A (nl)	1980-08-28	1981-08-11	Werkwijze voor het selectief bereiden van polyalkyleenpolyamines.

Country Status (8)

Country	Link
US (1)	US4324917A (fr)
JP (1)	JPS59496B2 (fr)
BE (1)	BE890094A (fr)
DE (1)	DE3127105A1 (fr)
ES (1)	ES505006A0 (fr)
GB (1)	GB2083021B (fr)
NL (1)	NL8103758A (fr)
SE (1)	SE8105080L (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4394524A (en) *	1981-08-31	1983-07-19	Air Products And Chemicals, Inc.	Preparation of polyalkylene polyamines from ammonia, alkyleneamine, and alkanolamine
US4503250A (en) *	1981-09-30	1985-03-05	Union Carbide Corporation	Preparation of polyalkylene polyamines
CA1224896A (fr) *	1982-04-30	1987-07-28	Union Carbide Corporation	Preparation de polyalcoylene-polyamines en presence d'un amide phosphore comme catalyseur
US4463193A (en) *	1983-07-19	1984-07-31	Air Products And Chemicals, Inc.	Production of noncyclic polyalkylene polyamines
US4578517A (en) *	1983-09-16	1986-03-25	Air Products And Chemicals, Inc.	Polyalkylene polyamines from alkanolamine and ammonia or amines using group IIIB metal acid phosphate catalysts
JPS6078945A (ja) *	1983-10-06	1985-05-04	Mitsui Toatsu Chem Inc	ジエチレントリアミンの製造法
US4605770A (en) *	1983-12-22	1986-08-12	Air Products And Chemicals, Inc.	Noncyclic polyalkylene polyamines by the reaction of an alkanolamine compound and an alkyleneamine compound in the presence of a Group IIA or Group IIIB metal acid phosphate catalyst
US4503253A (en) *	1984-03-08	1985-03-05	Air Products And Chemicals, Inc.	Production of noncyclic polyalkyene polyamines
US4550209A (en) *	1984-07-26	1985-10-29	Texaco Inc.	Process for the preparation of linear polyethylenepolyamines by reacting monoethanolamine with ethylenediamine in the presence of an intercalatively active catalyst
US4617418A (en) *	1984-11-26	1986-10-14	Air Products And Chemicals, Inc.	Polyalkylene polyamines via vapor phase reaction
IN172191B (fr) *	1985-03-14	1993-05-01	Lubrizol Corp
US5011999A (en) *	1989-02-23	1991-04-30	The Dow Chemical Company	Process of preparing non-cyclic polyalkylenepolyamines employing group VB metal catalysts
US5210306A (en) *	1989-08-08	1993-05-11	Union Carbide Chemicals & Plastics Technology Corporation	Promoted amines catalysis
US5202492A (en) *	1989-08-08	1993-04-13	Union Carbide Chemicals & Plastics Technology Corporation	Amines catalysis using metallic phosphate condensation catalysts having a cyclic structure
US5225600A (en) *	1989-08-08	1993-07-06	Union Carbide Chemicals & Plastics Technology Corporation	Amines catalysis using group VIB metal-containing condensation catalysts
US5101074A (en) *	1989-08-08	1992-03-31	Union Carbide Chemicals & Plastics Technology Corporation	Vicinal di(hetro) alkylene organometalates and processes for the production of amines therewith
US4983736A (en) *	1989-08-08	1991-01-08	Union Carbide Chemicals And Plastic Company Inc.	Amines catalysis using metallic polyphosphate condensation catalysts having a condensed structure
US5225598A (en) *	1990-03-30	1993-07-06	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of linear pentaethylenehexamine and hydroxyethyldiethylenetriamine
US5166415A (en) *	1990-03-30	1992-11-24	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of diethylenetriamine and aminoethylethanolamine
US5231230A (en) *	1990-03-30	1993-07-27	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of diethylenetriamine
US5214215A (en) *	1990-03-30	1993-05-25	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of aminoethylethanolamine
US5220071A (en) *	1990-03-30	1993-06-15	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of pentaethylenehexamine and hydroxyethyltriethylenetetramine
US5214213A (en) *	1990-03-30	1993-05-25	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of linear tetraethylenepentamine and hydroxyethyldiethylenetriamine
US5225599A (en) *	1990-03-30	1993-07-06	Union Carbide Chemicals & Plastics Technology Corporation	Selective production of linear triethylenetetramine and aminoethylethanolamine
US5019653A (en) *	1990-05-14	1991-05-28	Texaco Chemical Company	Purification of polyamines derived from polyhydroxyl compounds
US5214155A (en) *	1992-04-29	1993-05-25	Texaco Chemical Company	Method for 1,2-substituted imidazoline compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB726925A (en) *	1952-05-20	1955-03-23	Permutit Co Ltd	Improvements in cation-exchange resins
US4036881A (en) *	1975-06-02	1977-07-19	Texaco Development Corporation	Preparation of polyalkylene polyamines
US4044053A (en) *	1975-06-02	1977-08-23	Texaco Development Corporation	Preparation of polyalkylene polyamines

1980
- 1980-08-28 US US06/182,206 patent/US4324917A/en not_active Expired - Lifetime
1981
- 1981-07-09 DE DE19813127105 patent/DE3127105A1/de not_active Withdrawn
- 1981-07-21 GB GB8122363A patent/GB2083021B/en not_active Expired
- 1981-08-11 NL NL8103758A patent/NL8103758A/nl not_active Application Discontinuation
- 1981-08-26 ES ES505006A patent/ES505006A0/es active Granted
- 1981-08-26 BE BE0/205772A patent/BE890094A/fr not_active IP Right Cessation
- 1981-08-27 SE SE8105080A patent/SE8105080L/ not_active Application Discontinuation
- 1981-08-28 JP JP56134374A patent/JPS59496B2/ja not_active Expired

Also Published As

Publication number	Publication date
ES8206583A1 (es)	1982-08-16
GB2083021A (en)	1982-03-17
JPS5774331A (en)	1982-05-10
JPS59496B2 (ja)	1984-01-07
ES505006A0 (es)	1982-08-16
SE8105080L (sv)	1982-03-01
BE890094A (fr)	1982-02-26
GB2083021B (en)	1984-07-25
US4324917A (en)	1982-04-13
DE3127105A1 (de)	1982-04-15

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-04-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8103758A (nl)	1982-03-16	Werkwijze voor het selectief bereiden van polyalkyleenpolyamines.
CA1068304A (fr)	1979-12-18	Preparation de polyalkylene polyamines
US4044053A (en)	1977-08-23	Preparation of polyalkylene polyamines
US4578517A (en)	1986-03-25	Polyalkylene polyamines from alkanolamine and ammonia or amines using group IIIB metal acid phosphate catalysts
EP0049463B1 (fr)	1985-01-23	Préparation de polyalkylène polyamines linéaires
JPS6041641A (ja)	1985-03-05	非環状ポリアルキレンポリアミンの製法
US4605770A (en)	1986-08-12	Noncyclic polyalkylene polyamines by the reaction of an alkanolamine compound and an alkyleneamine compound in the presence of a Group IIA or Group IIIB metal acid phosphate catalyst
US4503253A (en)	1985-03-05	Production of noncyclic polyalkyene polyamines
US20200165187A1 (en)	2020-05-28	Multi-step process for converting cyclic alkyleneureas into their corresponding alkyleneamines
US4582904A (en)	1986-04-15	Amine production via condensation reactions using rare earth metal hydrogen phosphates as catalysts
JPH10513456A (ja)	1998-12-22	アミノエチルエタノールアミンおよび／またはヒドロキシエチルピペラジンを製造するための方法
EP0197612A2 (fr)	1986-10-15	Schéma d'un procédé interchangeable
CA1070309A (fr)	1980-01-22	Preparation de la n-(aminoalkyl) piperazine
CN110997640B (zh)	2023-07-28	将亚乙基胺化合物的环状单脲转化为亚乙基胺化合物的方法
JP2922553B2 (ja)	1999-07-26	直鎖ポリエチレンポリアミン類の接触合成
CA1078382A (fr)	1980-05-27	Production de composes bis-(n,n-amino disubstitue)
JPS6341897B2 (fr)	1988-08-19
US5371290A (en)	1994-12-06	Preparation of N,N-dialkarylamines
JPH0788333B2 (ja)	1995-09-27	レゾルシノールからのｍ−アミノフェノールの製造方法
JPH0625137A (ja)	1994-02-01	カルバメ−トの製造法
JPS58135841A (ja)	1983-08-12	ジエチレントリアミンの製造方法
JPS5955858A (ja)	1984-03-31	ビス〔β−（Ｎ，Ｎ−ジメチルアミノ）アルキル〕エ−テルの製造方法
BE842465A (fr)	1976-12-01	Procede de preparation de polyalkylenepolyamines non cycliques