Organic membranes for H2 separation

doi:10.11949/0438-1157.20230652

Abstract

Abstract:

H₂ is important chemical and energy carrier. The separation and purification processes play a crucial role on the economics of H₂. Organic polymer membranes have the advantages of low cost, strong processability, diverse structures, and stable performance, and have become the most widely used membrane materials in the field of H₂ separation. In this paper, the separation mechanism is introduced, followed by discussions of membrane materials, preparation methods and performance. Afterwards, the applications of organic membranes in H₂ separation are reviewed, and future works are prospected.

Key words: hydrogen, polymer, membrane, separation

摘要：

氢气是重要的化工原料和燃料，其分离纯化的效果将直接影响使用成本。有机聚合物膜具有成本低、可加工性强、结构多样、性能稳定等优点，已成为H₂分离领域应用最多的膜材料。介绍了H₂分离有机膜的分离机理，讨论了H₂分离有机膜的种类、制备方法和性能，综述了其应用现状，并对未来的发展前景进行了展望。

关键词: 氢气, 聚合物, 膜, 分离

CLC Number:

TQ 028.8

Jiao ZHU, Liping LUAN, Shenzhen CONG, Xinlei LIU. Organic membranes for H₂ separation[J]. CIESC Journal, 2024, 75(1): 138-158.

朱娇, 栾丽萍, 从深震, 刘新磊. 氢气分离有机膜[J]. 化工学报, 2024, 75(1): 138-158.

Figures/Tables 13

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118	Abdul Nasir N, Ling J H, Junaidi M U M, et al. 1, 3-propane diamine/1, 4-butane diamine cross-linking modification of polyimide membrane for hydrogen selective separation: effect of diamine mixture ratio[J]. Asia-Pacific Journal of Chemical Engineering, 2020, 15(3): e2411.
119	Kai T, Taniguchi I, Duan S H, et al. Molecular gate membrane: poly(amidoamine) dendrimer/polymer hybrid membrane modules for CO₂ capture[J]. Energy Procedia, 2013, 37: 961-968.
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公司	膜材料	膜组件
Permea（Air Products）	聚砜，聚酰亚胺	中空纤维式
Medal（Air Liquide）	聚酰亚胺，聚芳酰胺	中空纤维式
Ube	聚酰亚胺	中空纤维式
Monsanto	聚砜-硅橡胶	中空纤维式
Separex	醋酸纤维素	螺旋卷式
大连化学物理研究所（天邦）	聚砜，聚酰亚胺	中空纤维式/卷式

公司	膜材料	膜组件
Permea（Air Products）	聚砜，聚酰亚胺	中空纤维式
Medal（Air Liquide）	聚酰亚胺，聚芳酰胺	中空纤维式
Ube	聚酰亚胺	中空纤维式
Monsanto	聚砜-硅橡胶	中空纤维式
Separex	醋酸纤维素	螺旋卷式
大连化学物理研究所（天邦）	聚砜，聚酰亚胺	中空纤维式/卷式

聚合物	生产厂家	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				文献
聚合物	生产厂家	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	文献
Matrimid^®5218	Vantico Inc. (Luxemburg)	35	3.5^①	27.16	3.88	97.00	129.33		[12]
CA 320S		35	1	12	2.53	80	80	14.63	[13]
CA 398-30		35	1	6.05	3.29	106.14	116.35	18.91	[13]
CA 435-75		35	1	15.5	2.36	67.39	77.5	10.62	[13]
Victrex 600P	ICI	90							[14]
UDEL 3500	Union Carbide	90							[14]
SU341025	Goodfellow & Co.	35	20	14.5		58	58	10.14	[15]
Radel^® A PES	Solvay Advanced Polymers L.L.C., GA, USA	35	3.5	8.96	2.65	69.5	80	11.59	[16]
乙基纤维素		30		87	3.28				[17]
聚砜		30		14	2.50				[17]
聚醚酰亚胺		30		7.8	5.91				[17]
聚甲基戊烯		30		125	1.48				[17]
聚苯醚		30		113	1.49				[17]
PPO				61	1	14.19	14.88	3.63	[18]
Lenzing P84									[18]
聚酰胺酰亚胺									[18]
聚砜-硅橡胶	Monsanto					39	24		[18]
聚酰亚胺	Ube					35.4			[18]
醋酸纤维素	Separex					33	26		[18]
聚二甲基硅氧烷									[19]

聚合物	生产厂家	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				文献
聚合物	生产厂家	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	文献
Matrimid^®5218	Vantico Inc. (Luxemburg)	35	3.5^①	27.16	3.88	97.00	129.33		[12]
CA 320S		35	1	12	2.53	80	80	14.63	[13]
CA 398-30		35	1	6.05	3.29	106.14	116.35	18.91	[13]
CA 435-75		35	1	15.5	2.36	67.39	77.5	10.62	[13]
Victrex 600P	ICI	90							[14]
UDEL 3500	Union Carbide	90							[14]
SU341025	Goodfellow & Co.	35	20	14.5		58	58	10.14	[15]
Radel^® A PES	Solvay Advanced Polymers L.L.C., GA, USA	35	3.5	8.96	2.65	69.5	80	11.59	[16]
乙基纤维素		30		87	3.28				[17]
聚砜		30		14	2.50				[17]
聚醚酰亚胺		30		7.8	5.91				[17]
聚甲基戊烯		30		125	1.48				[17]
聚苯醚		30		113	1.49				[17]
PPO				61	1	14.19	14.88	3.63	[18]
Lenzing P84									[18]
聚酰胺酰亚胺									[18]
聚砜-硅橡胶	Monsanto					39	24		[18]
聚酰亚胺	Ube					35.4			[18]
醋酸纤维素	Separex					33	26		[18]
聚二甲基硅氧烷									[19]

工业应用	分离组分	文献
合成气比例调整	H₂/CO	[18]
合成氨弛放气中回收氢气	H₂/N₂	[18]
电解水制氢中纯化氢气	H₂/O₂	[2]
光催化制氢中分离氢气	H₂/O₂	[2]
炼厂气中回收氢气	H₂/轻烃	[18]
甲醇裂解制氢中纯化氢气	H₂/CO₂、CO、CH₄	[2]
生物质制氢中纯化氢气	H₂/O₂、CO₂、H₂O	[2]
煤制甲醇中回收氢气	H₂/CO、CO₂、N₂、H₂O、Ar	[18]

Organic membranes for H₂ separation

氢气分离有机膜

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References 126

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膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				气体组成	文献
膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	气体组成	文献
PDMA-MA PI	350	2	63.45	18.7				混合气	[31]
Ac-CoPI-TB-2	200	10	1848	3.7				混合气	[35]
PI-TB-N	200	10	2255	3.45				混合气	[35]
BCBr4-SBIDA	35	2	274	1.99	52	55	8.78	纯气体	[34]
6FDA-SBIDA	35	2	181	1.52	33	53	7.61	纯气体	[34]
CpODA-DAT	35	1	608	2.31	30.7	34.2	6.89	纯气体	[36]
CpODA-DAPI	35	1	166	3.06	47.5	57.3	7.98	纯气体	[36]
6FDA-IPD PHI	35	4	39.3	9.4				纯气体	[37]
BPDA-IPD PHI	35	4	4.9	24.5				纯气体	[37]
PIP-TMC-KRO	23	1	6.73	10.1	312	311.67	39.85	纯气体	[38]
PPD-TMC-KRO	23	1	5.87	10.8	296	362.22	49.3	纯气体	[38]
EDA-PI	35	3.5	32.6	102				纯气体	[39]
EDA-PI	35	3.5^①	19.4	16.6				混合气	[39]
TB-MSBC	35	3.5	310.6	1.9	27.4	31.9			[40]
6FDA-mPD	35	10	40.2	4.4	89.9	252		纯气体	[41]
6FDA-6HpDA	35	1	65	1.8	45.1	77.4		纯气体	[42]
6FDA-2,6-DATr	35	6.8	106.6	2.5		115		混合气	[43]
6FDA-terphenyl	35	3.5	45.64	2.12	44.75	61.1		纯气体	[44]
6FDA-biphenylb	35	3.5	34.28	2.64	55.65	95.7		纯气体	[44]
BAPB-10	36	6	32.2	1.22	68.51	69.3		纯气体	[45]
T-PI		1	518	0.64	9.25	15.7		纯气体	[46]
P84-PDMS-3A	35	1	20.85	5.72	98.77	231.92		纯气体	[28]
300s-3L-PEI	30	2	10.4	2.08	308			纯气体	[47]
PEI-HF	25	8	107.52^②	5.6				混合气	[48]
DA0-MAT	35	2	13.9	5	152	186	15.44	纯气体	[49]
FDA1-MAT	35	2	47	3.36	98	119	15.16	纯气体	[49]
BCDA-ODA	30		41.41	3.7	57.51	121.79	15.45	纯气体	[50]
DOCDA-ODA	30		9.84	4.33	175.71	258.95	20.5	纯气体	[50]
HAB-6FDA	37	2.7	73.7	3.2	29.0	54.6	15.04	纯气体	[51]
GEN7	300	10	391.5	7.6				混合气	[27]
[HF-PEI₁₀/PAA₄]₂₀	TR	1	58.68	>200	>2000			混合气	[52]
[f-HF-PEI₁₀/PAA₄]₅	TR	1	179.55	>200	61.6			混合气	[52]
XLP84-6h	100	1	47	14				纯气体	[33]
PEI	30	5	6.9	4.42	133	238	18.16	纯气体	[53]
6FDA-PPDA(CH₃)	35	10	100	1.82	41.67	50	8.33	纯气体	[54]
6FDA-1,4-trip_CF₃	35	8.85	59.4	3				纯气体	[55]
Matrimid^®5218	35	3.5^③	27.16	3.88		129.33		纯气体	[13]
6FDA-FB	35	6.8	73	2.12	60.83	104.29		纯气体	[56]

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膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				气体组成	文献
膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	气体组成	文献
TPBI-（H₃PO₄)_0.98	150	7	46.7	16				混合气	[59]
PBI-250	300	5	45	44	286			纯气体	[62]
PBI-BuI	35	20	10.7	5.6	176	208	25.48	纯气体	[70]
XLPBI-6H	200	11	39	23				纯气体	[58]
PBI	200	11	45	15				纯气体	[58]
TADPS-TPA	190	3	31	18	155	258.33		纯气体	[71]
TADPS-IPA	190	3	30.1	24.6	177.06	358.3		纯气体	[71]
TADPS-OBA	190	3	38	9.7	92.68	123.78		纯气体	[71]
m-PBI	190	3	22.1	23.3	184.17	221		纯气体	[71]
Celazole^®	35	10	4	29				纯气体	[65]
6F-PBI	250	3.4	997.2	5.174	18.72			纯气体	[63]
BTBP-PBI	250	3.4	710.4	7.111	23.43			纯气体	[63]
Phenylindane-PBI	250	3.4	480.6	6.522	26.32			纯气体	[63]
PFCB-PBI	250	3.4	323.1	6.604	23.45			纯气体	[63]
m-PBI	250	3.4	76.81	23.03	98.32			纯气体	[63]
PBDI	150	1	72.3	23				混合气	[72]
TBB-PBI	150	14	9.6	24				混合气	[73]
PBI-(H₃PO₄)_0.16	150	14	12	34				混合气	[64]
PBI w/40%(mass) PMF（250℃）	250	2	56.8	12.9		82.32		混合气	[74]
PBI-HFA	24	7.74	121.3	2.4				纯气体	[75]
[DMABPBI][I]	35	20	1.58	12.2				纯气体	[76]
[DMABPBI][BF₄]	35	20	2.53	6				纯气体	[76]
PBI-HFA	400	5~8	24.2	26.19				纯气体	[77]
m-PBI	250	3.4	88	47.6		233.6		混合气	[78]
Celazole^®+1-IM	35	10	3.4	30.91			75.56	纯气体	[60]
20/80 PI/PBI+1-IM	35	10	3.6	41.86			87.80	纯气体	[60]
Matrimid/PBI（1∶3）	35	3.5^①	5.47	9.43	260.48	563.92		纯气体	[12]
fMatrimid/PBI（1∶3）-p-xylene diamine 10 days	35	3.5^①	3.6	26.09	272.73	1161.29		纯气体	[12]
HFM-2	250	1.36	77.55	25.7				纯气体	[79]
T-C-BILP	200	1	6.35	56.3				混合气	[22]
T-C-BILP	250	1	21.95	28.5				混合气	[22]
BILP-5	TR	1	362	16	14.1^②			混合气	[69]
BILP-101x	150	2	9.68	39.5				混合气	[67]

膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				气体组成	文献
膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	气体组成	文献
TPBI-（H₃PO₄)_0.98	150	7	46.7	16				混合气	[59]
PBI-250	300	5	45	44	286			纯气体	[62]
PBI-BuI	35	20	10.7	5.6	176	208	25.48	纯气体	[70]
XLPBI-6H	200	11	39	23				纯气体	[58]
PBI	200	11	45	15				纯气体	[58]
TADPS-TPA	190	3	31	18	155	258.33		纯气体	[71]
TADPS-IPA	190	3	30.1	24.6	177.06	358.3		纯气体	[71]
TADPS-OBA	190	3	38	9.7	92.68	123.78		纯气体	[71]
m-PBI	190	3	22.1	23.3	184.17	221		纯气体	[71]
Celazole^®	35	10	4	29				纯气体	[65]
6F-PBI	250	3.4	997.2	5.174	18.72			纯气体	[63]
BTBP-PBI	250	3.4	710.4	7.111	23.43			纯气体	[63]
Phenylindane-PBI	250	3.4	480.6	6.522	26.32			纯气体	[63]
PFCB-PBI	250	3.4	323.1	6.604	23.45			纯气体	[63]
m-PBI	250	3.4	76.81	23.03	98.32			纯气体	[63]
PBDI	150	1	72.3	23				混合气	[72]
TBB-PBI	150	14	9.6	24				混合气	[73]
PBI-(H₃PO₄)_0.16	150	14	12	34				混合气	[64]
PBI w/40%(mass) PMF（250℃）	250	2	56.8	12.9		82.32		混合气	[74]
PBI-HFA	24	7.74	121.3	2.4				纯气体	[75]
[DMABPBI][I]	35	20	1.58	12.2				纯气体	[76]
[DMABPBI][BF₄]	35	20	2.53	6				纯气体	[76]
PBI-HFA	400	5~8	24.2	26.19				纯气体	[77]
m-PBI	250	3.4	88	47.6		233.6		混合气	[78]
Celazole^®+1-IM	35	10	3.4	30.91			75.56	纯气体	[60]
20/80 PI/PBI+1-IM	35	10	3.6	41.86			87.80	纯气体	[60]
Matrimid/PBI（1∶3）	35	3.5^①	5.47	9.43	260.48	563.92		纯气体	[12]
fMatrimid/PBI（1∶3）-p-xylene diamine 10 days	35	3.5^①	3.6	26.09	272.73	1161.29		纯气体	[12]
HFM-2	250	1.36	77.55	25.7				纯气体	[79]
T-C-BILP	200	1	6.35	56.3				混合气	[22]
T-C-BILP	250	1	21.95	28.5				混合气	[22]
BILP-5	TR	1	362	16	14.1^②			混合气	[69]
BILP-101x	150	2	9.68	39.5				混合气	[67]

膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				气体组成	文献
膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	气体组成	文献
BTA-CANAL-2	35	1	1685		15	14	4.23	纯气体	[81]
PMDA-CANAL-2	35	1	1113		14	12	4.05	纯气体	[81]
CBDA-CANAL-2	35	1	747		13	12	4.32	纯气体	[81]
BTA-CANAL-4	35	1	656		25	22	5.70	纯气体	[81]
BTA-CANAL-3	35	1	266	1.16	28	25	6.65	纯气体	[81]
6FDA-Durene	35	1	932		10.1	10.3	3.44	纯气体	[84]
6FDA-DMNDA	35	1	1055		11.0	10.7	3.58	纯气体	[84]
SBIDA-DMNDA	35	1	1372		13.7	9.7	3.89	纯气体	[84]
BTA-6FDA-DMNDA	35	1	1073		16.0	15.2	4.63	纯气体	[84]
CpODA-6FDA-DMNDA	35	1	727		16.0	14.4	4.66	纯气体	[84]
PIM-1	35	2	3250		13.0	10.3		纯气体	[85]
O₃-PIM-300	35	2	683	4.85	142	182		纯气体	[85]
PIM-1-300	30	0.2^①	1078		18.27	7.54	2.64	纯气体	[86]
PIM-B	30	1.08	110.41	1.57	38	57	7.61	纯气体	[87]
PEI/PIM-B（80/20）	35	5	14.11	8.66	159	271	14.55	纯气体	[52]
PIM-UV-4hr	35	3.5	452	7.3	166	173.9	27.39	纯气体	[82]
PIM-PI-1	30	1	530		11.3	6.9	3.53	纯气体	[86]
PIM-PI-2	30	1	220	1.05	24.4	24.4	5.64	纯气体	[86]
PIM-1/Matrimid^®	35	3.5	395	9.6	91.9	116.2	12.34	纯气体	[88]
TPIM-1			1105		156	152	18.11	纯气体	[89]
KAUST-PI-1			3431		39	41	6.33	纯气体	[89]
PIM-TRIP-TB			4740		25	22	4.42	纯气体	[89]
PIM-EA-TB			4442		24	20	4.76	纯气体	[89]
PIM-1(P4.5)	25^②		1028	6.5	109.4	127.1		纯气体	[90]
PIM-1(M4.5)	25^②		1535	4.1	86.2	93.5		纯气体	[90]
PIM-F-60	22^③		457^④	16.9	515	1115		纯气体	[91]
PIM-1	-30		1557	1.13	91.59	9.79	74.14	纯气体	[92]
PIM-t-BOC	35	1	130	1.3	36	26	6.8	纯气体	[93]
SPIM-1-4	35	2	2957	1.4	47	50.1	7.7	纯气体	[94]
PIM-EA(Me₂)-TB 75%			26^⑤		86.67	86.67	20	纯气体	[95]

膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	选择性				气体组成	文献
膜名称	温度/℃	压力/atm	H₂渗透系数/Barrer	H₂/CO₂	H₂/N₂	H₂/CH₄	H₂/O₂	气体组成	文献
BTA-CANAL-2	35	1	1685		15	14	4.23	纯气体	[81]
PMDA-CANAL-2	35	1	1113		14	12	4.05	纯气体	[81]
CBDA-CANAL-2	35	1	747		13	12	4.32	纯气体	[81]
BTA-CANAL-4	35	1	656		25	22	5.70	纯气体	[81]
BTA-CANAL-3	35	1	266	1.16	28	25	6.65	纯气体	[81]
6FDA-Durene	35	1	932		10.1	10.3	3.44	纯气体	[84]
6FDA-DMNDA	35	1	1055		11.0	10.7	3.58	纯气体	[84]
SBIDA-DMNDA	35	1	1372		13.7	9.7	3.89	纯气体	[84]
BTA-6FDA-DMNDA	35	1	1073		16.0	15.2	4.63	纯气体	[84]
CpODA-6FDA-DMNDA	35	1	727		16.0	14.4	4.66	纯气体	[84]
PIM-1	35	2	3250		13.0	10.3		纯气体	[85]
O₃-PIM-300	35	2	683	4.85	142	182		纯气体	[85]
PIM-1-300	30	0.2^①	1078		18.27	7.54	2.64	纯气体	[86]
PIM-B	30	1.08	110.41	1.57	38	57	7.61	纯气体	[87]
PEI/PIM-B（80/20）	35	5	14.11	8.66	159	271	14.55	纯气体	[52]
PIM-UV-4hr	35	3.5	452	7.3	166	173.9	27.39	纯气体	[82]
PIM-PI-1	30	1	530		11.3	6.9	3.53	纯气体	[86]
PIM-PI-2	30	1	220	1.05	24.4	24.4	5.64	纯气体	[86]
PIM-1/Matrimid^®	35	3.5	395	9.6	91.9	116.2	12.34	纯气体	[88]
TPIM-1			1105		156	152	18.11	纯气体	[89]
KAUST-PI-1			3431		39	41	6.33	纯气体	[89]
PIM-TRIP-TB			4740		25	22	4.42	纯气体	[89]
PIM-EA-TB			4442		24	20	4.76	纯气体	[89]
PIM-1(P4.5)	25^②		1028	6.5	109.4	127.1		纯气体	[90]
PIM-1(M4.5)	25^②		1535	4.1	86.2	93.5		纯气体	[90]
PIM-F-60	22^③		457^④	16.9	515	1115		纯气体	[91]
PIM-1	-30		1557	1.13	91.59	9.79	74.14	纯气体	[92]
PIM-t-BOC	35	1	130	1.3	36	26	6.8	纯气体	[93]
SPIM-1-4	35	2	2957	1.4	47	50.1	7.7	纯气体	[94]
PIM-EA(Me₂)-TB 75%			26^⑤		86.67	86.67	20	纯气体	[95]